EP1506336B1 - Softening silicone formulations for textile finishing - Google Patents
Softening silicone formulations for textile finishing Download PDFInfo
- Publication number
- EP1506336B1 EP1506336B1 EP20030749889 EP03749889A EP1506336B1 EP 1506336 B1 EP1506336 B1 EP 1506336B1 EP 20030749889 EP20030749889 EP 20030749889 EP 03749889 A EP03749889 A EP 03749889A EP 1506336 B1 EP1506336 B1 EP 1506336B1
- Authority
- EP
- European Patent Office
- Prior art keywords
- alkyl
- mono
- chain
- sum
- independently
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 238000009472 formulation Methods 0.000 title claims abstract description 45
- 229920001296 polysiloxane Polymers 0.000 title description 26
- 238000009988 textile finishing Methods 0.000 title 1
- 150000001875 compounds Chemical class 0.000 claims abstract description 38
- 239000004753 textile Substances 0.000 claims abstract description 27
- 238000000034 method Methods 0.000 claims abstract description 10
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 60
- 125000000229 (C1-C4)alkoxy group Chemical group 0.000 claims description 32
- 229920006395 saturated elastomer Polymers 0.000 claims description 27
- -1 R11 Chemical compound 0.000 claims description 25
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 25
- 125000000217 alkyl group Chemical group 0.000 claims description 24
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical group C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 18
- 125000004433 nitrogen atom Chemical group N* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 18
- 239000001301 oxygen Substances 0.000 claims description 18
- 125000004178 (C1-C4) alkyl group Chemical group 0.000 claims description 17
- 125000000041 C6-C10 aryl group Chemical group 0.000 claims description 16
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 150000002191 fatty alcohols Chemical class 0.000 claims description 10
- 229920000742 Cotton Polymers 0.000 claims description 9
- 125000006702 (C1-C18) alkyl group Chemical group 0.000 claims description 8
- 239000000654 additive Substances 0.000 claims description 8
- 239000001257 hydrogen Substances 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical group CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 claims description 6
- 239000004215 Carbon black (E152) Substances 0.000 claims description 5
- 239000004952 Polyamide Substances 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 5
- 239000000835 fiber Substances 0.000 claims description 5
- 229930195733 hydrocarbon Natural products 0.000 claims description 5
- 229920002647 polyamide Polymers 0.000 claims description 5
- 229920000728 polyester Polymers 0.000 claims description 5
- 210000002268 wool Anatomy 0.000 claims description 5
- 239000002253 acid Substances 0.000 claims description 4
- 150000007513 acids Chemical class 0.000 claims description 4
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 4
- 229930195729 fatty acid Natural products 0.000 claims description 4
- 239000000194 fatty acid Substances 0.000 claims description 4
- 150000004665 fatty acids Chemical class 0.000 claims description 4
- 235000021355 Stearic acid Nutrition 0.000 claims description 3
- 125000000129 anionic group Chemical group 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 229920001577 copolymer Polymers 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 claims description 3
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 claims description 3
- 229920002239 polyacrylonitrile Polymers 0.000 claims description 3
- 239000008117 stearic acid Substances 0.000 claims description 3
- 229920002994 synthetic fiber Polymers 0.000 claims description 3
- 239000012209 synthetic fiber Substances 0.000 claims description 3
- JNYAEWCLZODPBN-JGWLITMVSA-N (2r,3r,4s)-2-[(1r)-1,2-dihydroxyethyl]oxolane-3,4-diol Chemical class OC[C@@H](O)[C@H]1OC[C@H](O)[C@H]1O JNYAEWCLZODPBN-JGWLITMVSA-N 0.000 claims description 2
- 102000011782 Keratins Human genes 0.000 claims description 2
- 108010076876 Keratins Proteins 0.000 claims description 2
- 239000004743 Polypropylene Substances 0.000 claims description 2
- 150000001298 alcohols Chemical class 0.000 claims description 2
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 2
- 150000001449 anionic compounds Chemical class 0.000 claims description 2
- 125000004122 cyclic group Chemical group 0.000 claims description 2
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 claims description 2
- 125000005456 glyceride group Chemical group 0.000 claims description 2
- 238000009981 jet dyeing Methods 0.000 claims description 2
- 150000002891 organic anions Chemical class 0.000 claims description 2
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 2
- 229920001155 polypropylene Polymers 0.000 claims description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims 4
- 238000004519 manufacturing process Methods 0.000 claims 1
- 239000004094 surface-active agent Substances 0.000 abstract description 9
- 150000003839 salts Chemical class 0.000 abstract description 4
- 239000002270 dispersing agent Substances 0.000 abstract 1
- 239000002184 metal Substances 0.000 abstract 1
- 150000007522 mineralic acids Chemical class 0.000 abstract 1
- 238000010008 shearing Methods 0.000 abstract 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 239000004530 micro-emulsion Substances 0.000 description 9
- 238000001556 precipitation Methods 0.000 description 8
- 239000000839 emulsion Substances 0.000 description 7
- PUAQLLVFLMYYJJ-UHFFFAOYSA-N 2-aminopropiophenone Chemical compound CC(N)C(=O)C1=CC=CC=C1 PUAQLLVFLMYYJJ-UHFFFAOYSA-N 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- 238000002474 experimental method Methods 0.000 description 6
- 239000004744 fabric Substances 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PXBRQCKWGAHEHS-UHFFFAOYSA-N dichlorodifluoromethane Chemical compound FC(F)(Cl)Cl PXBRQCKWGAHEHS-UHFFFAOYSA-N 0.000 description 5
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- 150000002431 hydrogen Chemical class 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 229940087291 tridecyl alcohol Drugs 0.000 description 4
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 3
- 125000002947 alkylene group Chemical group 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 239000012141 concentrate Substances 0.000 description 3
- 239000003921 oil Substances 0.000 description 3
- 229920000570 polyether Polymers 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- 239000001632 sodium acetate Substances 0.000 description 3
- 235000017281 sodium acetate Nutrition 0.000 description 3
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 description 3
- 0 C*(C)N(*)NN(*)**(C)(*)* Chemical compound C*(C)N(*)NN(*)**(C)(*)* 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000000872 buffer Substances 0.000 description 2
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000004043 dyeing Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 230000032050 esterification Effects 0.000 description 2
- 238000005886 esterification reaction Methods 0.000 description 2
- 239000002979 fabric softener Substances 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000002244 precipitate Substances 0.000 description 2
- NAWXUBYGYWOOIX-SFHVURJKSA-N (2s)-2-[[4-[2-(2,4-diaminoquinazolin-6-yl)ethyl]benzoyl]amino]-4-methylidenepentanedioic acid Chemical compound C1=CC2=NC(N)=NC(N)=C2C=C1CCC1=CC=C(C(=O)N[C@@H](CC(=C)C(O)=O)C(O)=O)C=C1 NAWXUBYGYWOOIX-SFHVURJKSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-N Propionic acid Chemical class CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- ZUQAPLKKNAQJAU-UHFFFAOYSA-N acetylenediol Chemical class OC#CO ZUQAPLKKNAQJAU-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005370 alkoxysilyl group Chemical group 0.000 description 1
- 150000008051 alkyl sulfates Chemical class 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 238000006254 arylation reaction Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 238000010924 continuous production Methods 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 238000005187 foaming Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 150000008282 halocarbons Chemical class 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- TXXWBTOATXBWDR-UHFFFAOYSA-N n,n,n',n'-tetramethylhexane-1,6-diamine Chemical compound CN(C)CCCCCCN(C)C TXXWBTOATXBWDR-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- 150000003961 organosilicon compounds Chemical class 0.000 description 1
- 239000012188 paraffin wax Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 229920000136 polysorbate Polymers 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003223 protective agent Substances 0.000 description 1
- 230000005588 protonation Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 230000006641 stabilisation Effects 0.000 description 1
- 238000011105 stabilization Methods 0.000 description 1
- 238000010186 staining Methods 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- 238000010023 transfer printing Methods 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01B—PERMANENT WAY; PERMANENT-WAY TOOLS; MACHINES FOR MAKING RAILWAYS OF ALL KINDS
- E01B37/00—Making, maintaining, renewing, or taking-up the ballastway or the track, not provided for in a single one of groups E01B27/00 - E01B35/00
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/155—Halides of elements of Groups 2 or 12 of the Periodic Table
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/07—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof
- D06M11/11—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with halogens; with halogen acids or salts thereof; with oxides or oxyacids of halogens or salts thereof with halogen acids or salts thereof
- D06M11/17—Halides of elements of Groups 3 or 13 of the Periodic Table
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- D—TEXTILES; PAPER
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/51—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof
- D06M11/55—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with sulfur, selenium, tellurium, polonium or compounds thereof with sulfur trioxide; with sulfuric acid or thiosulfuric acid or their salts
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M11/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising
- D06M11/68—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof
- D06M11/70—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with inorganic substances or complexes thereof; Such treatment combined with mechanical treatment, e.g. mercerising with phosphorus or compounds thereof, e.g. with chlorophosphonic acid or salts thereof with oxides of phosphorus; with hypophosphorous, phosphorous or phosphoric acids or their salts
- D06M11/71—Salts of phosphoric acids
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- D—TEXTILES; PAPER
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- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/01—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with natural macromolecular compounds or derivatives thereof
- D06M15/03—Polysaccharides or derivatives thereof
- D06M15/05—Cellulose or derivatives thereof
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino groups
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- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/647—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing polyether sequences
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
- E01C19/00—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving
- E01C19/12—Machines, tools or auxiliary devices for preparing or distributing paving materials, for working the placed materials, or for forming, consolidating, or finishing the paving for distributing granular or liquid materials
- E01C19/18—Devices for distributing road-metals mixed with binders, e.g. cement, bitumen, without consolidating or ironing effect
- E01C19/185—Devices for distributing road-metals mixed with binders, e.g. cement, bitumen, without consolidating or ironing effect for both depositing and spreading-out or striking-off the deposited mixture
-
- E—FIXED CONSTRUCTIONS
- E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
- E01B—PERMANENT WAY; PERMANENT-WAY TOOLS; MACHINES FOR MAKING RAILWAYS OF ALL KINDS
- E01B21/00—Track superstructure adapted for tramways in paved streets
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31652—Of asbestos
- Y10T428/31663—As siloxane, silicone or silane
Definitions
- the invention relates to novel formulations based on quaternized aminoalkyl silicones or siloxanes, processes for the preparation of these formulations and their use as textile auxiliaries for finishing textile materials.
- Silicone softeners are widely used for finishing textile materials. Requirements such as storage stability, temperature stability, resistance to whiteners and other anionic textile auxiliaries, resistance to changes in pH and salt addition and against the action of mechanical energy are of central importance for the practical use of the silicone softener emulsions. In particular, the stability against the action of mechanical energy, the shear stability or jet stability, often causes great difficulties for silicone softener emulsions under practical conditions (see R. Zyschka, Melliand Textilberichte 6/2001, 497).
- Microemulsions basically offer the advantage of thermodynamic stability.
- the equilibrium phase behavior has been treated depending on the structure of the oil to be emulsified and the surfactant (s).
- the addition of inorganic salts has also been studied systematically (cf. M. Kahlweit et al., Langmuir 11 [1995], 3382 ; M. Kahlweit et al., Langmuir 11 [1995 ]).
- the equilibrium phase behavior of microemulsions of low molecular weight silicones has also been investigated ( EP-A 774482 ; H. von Berlepsch et al., Progr. Colloid Polymer Science 111 [1998], 107 ).
- aminoalkylsiloxane oils are increasingly being replaced by polyether-modified aminoalkylsiloxane oils (cf. EP-A 578144 ).
- Finely divided microemulsions of aminoalkylsiloxanes are to be accessible in a two-stage process by preparing a concentrate of aminoalkylsiloxane, silicone-insoluble surfactant and a small amount of water, followed by rapid stirring in water ( US-A 4620878 ).
- aminosiloxane emulsions are to be mechanically stable by the use of water-soluble nonionic emulsifiers.
- water-soluble nonionic emulsifiers For extreme shear loads, as achieved on modern jet plants, it was found that the in DE-A 3723697 disclosed inventions are not sufficient to prevent precipitation in the jet equipment and on the textiles to be treated.
- WO 02/10501 should amino-functional organosilicon compounds without using water-soluble nonionic emulsifiers in jet dyeing machines mechanically stable. It was found that the in WO 02/10501 also be insufficient to reliably prevent precipitation on differently pretreated textiles.
- salts of strong acids for example Al 2 (SO 4 ) 3 ⁇ 18 H 2 O, secure the protonation of cationic dyes in thermal transfer printing pastes, but at the same time impair their stability (cf. US-A 5925701 ).
- Preferred hydrophilic, non-ionic surface-active compounds (a) are substances which lower the surface tension of water below 45 mN / m.
- These are ethylene / propylene oxide (EO / PO) modified compounds, optionally unsaturated and / or branched, from the group of fatty alcohols, fatty acids, alcohols, acids, alkylaryl derivatives, fatty amines, glycerides and sorbitan esters in which the number of EO / PO Is between 15 and 150, with the ratio of PO units to EO units being 0.25 or less than 0.25, and where the number of ethylene oxide (EO) units is greater than or equal to the number of carbon atoms in the non-electronic EO is part, and to alkyl polyglycosides, ethylene oxide / propylene oxide copolymers and polyether siloxanes.
- EO / PO ethylene / propylene oxide
- formulations according to the invention which contain, as compound (a), the ester of stearic acid and 40 mol of EO.
- the formulations according to the invention contain at least one nitrogen-quaternized aminoalkylsiloxane compound (silicone quat).
- Such compounds and their preparation are known, for example from WO 02/10 256 . WO 02/10257 . WO 02/10 259 .
- DE-A 100 36 522 and DE-A 102 12 470
- the formulations according to the invention also comprise any desired mixtures of the abovementioned quaternized aminoalkylsiloxane compounds with the corresponding nonquaternized compounds.
- these non-quaternized compounds in the formula (10), in each case, one of the radicals R 11 or R 12 or R 13 or R 14 is missing from the nitrogen atoms in the main chain
- inventively preferred quaternized aminoalkylsiloxane compounds are the subject of WO 02/10 259 and there described in general and specific.
- the addition of the described additives a) can be done in two ways. It is possible, on the one hand, for the additives according to the invention to be introduced directly into the formulations. On the other hand, it may be preferred under practical conditions to first dilute the formulations to application concentration and then to add the additives according to the invention to the prepared liquor.
- the formulations according to the invention may contain, in addition to the components (a), further surface-active components (f) which permit emulsification or microemulsification.
- components (f) are customary formulation agents known to the person skilled in the art for the preparation of the silicone (micro) emulsions, which however are not stable against high energy input alone.
- Preferred such components are f1) to f6): (f1) oxalkylation products obtainable by alkoxylation with ethylene oxide or propylene oxide of condensation products of phenolic OH group-containing aromatics with formaldehyde and NH-functional groups.
- nonionic or ionically modified compounds from the group of the alkoxylates, alkylolamides, esters, amine oxides and alkyl polyglycosides, in particular reaction products of alkylene oxides with alkylatable compounds, such as fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, carboxylic acid amides and resin acids.
- ethylene oxide from the class of reaction products of ethylene oxide with saturated and / or unsaturated fatty alcohols having 6 to 25 carbon atoms (commercially available, for example in the form of Renex® Produlct Zoo) or alkylphenols having 4 to 12 carbon atoms in the alkyl radical or saturated and / or unsaturated fatty amines having 14 to 20 carbon atoms or saturated and / or unsaturated fatty acids having 14 to 22 carbon atoms or esterification and / or arylation products prepared from natural or modified, optionally hydrogenated castor oil, optionally by esterification with Dicarboxylic acids are linked to recurring structural units.
- ionic or nonionic compounds from the group of the reaction products of alkylene oxide with sorbitan ester [Tween, ICI], alkoxylated acetylenediols and glycol, alkoxylated phenols, in particular phenol / styrene-polyglycol ethers.
- ionic or nonionic polymeric surfactants from the group of homopolymers and copolymers, graft copolymers and graft copolymers, and also random and linear block copolymers.
- anionic surfactants such as alkyl sulfates, ether sulfates, ether carboxylates, phosphate esters, sulfosuccinate amides, paraffin sulfonates, olefin sulfonates, sarcosinates, isothionates and taurates f6) amphoteric surfactants such as betaines and ampholytes, especially glycinates, propionates and imidazolines.
- Particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols and fatty acids having 4 to 14 alkoxy units, very particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols having 6 to 12 alkoxy units, especially formulations containing the ether of tridecyl alcohol with 12 mol EO containing tridecyl alcohol ether with 6 moles of EO.
- the formulation ingredients are generally added in conventional amounts of the formulation of the invention.
- the components (f) are preferably added in amounts of 1 to 200% by weight, preferably 10 to 80% by weight, particularly preferably 10 to 50% by weight, based on the quaternized aminoalkylsiloxane.
- the formulations may also contain further auxiliaries in the amounts customary for these auxiliaries.
- Usual aids within the meaning of the invention include leveling agents, wetting agents, gloss finishes, fiber-protecting agents, slip-resistance agents and other auxiliaries according to the prior art.
- leveling agents wetting agents, gloss finishes, fiber-protecting agents, slip-resistance agents and other auxiliaries according to the prior art.
- buffer systems can be incorporated to set an optimum pH during the equipment.
- the quaternized aminoalkylsiloxane compounds can be mixed with the components (a), if appropriate with the addition of further abovementioned constituents, preferably in the temperature range from 20 to 90.degree. C., more preferably from 25 to 70.degree more preferably at 30 to 60 ° C.
- the quaternized aminoalkylsiloxanes are preferably added to the compound (a); the quaternized aminoalkylsiloxane (silicone quat) is particularly preferably initially introduced, and the emulsion formation is completed by addition of the compound (a) and optionally further additives.
- the formulations according to the invention are outstandingly suitable as fabric softeners in the finishing of textile fabrics, in particular those of cotton, keratin fibers, preferably wool, silk or synthetic fibers or For example, very good for the equipment of textile fabrics made of blends of cotton with polyester, polyamide, polyacrylonitrile, wool or silk. Excellent results are equally obtained in the finishing of textile fabrics of synthetic fibers, in particular of polyester, polyamide, polypropylene or mixtures thereof
- Textile fabrics are preferably understood to mean woven fabrics, knitted fabrics, knitted fabrics and nonwovens.
- the equipment is generally carried out by the continuous process (pad-type or lisseuse process) or by the exhaustion process (jet process).
- the formulations according to the invention by one of these finishing processes, it has proven to be advantageous to comply with the following technological parameters:
- Formulation 1 Formulation 2
- Formulation 3 Formulation 3
- 430g SQ 430g SQ 430g SQ 258g Renex® 36 125g Renex® 36 125g Renex® 36 44.5g Renex® 30
- 44.5g Renex® 30 44.5g Renex® 30 10g of acetic acid 10g of acetic acid 10g of acetic acid 7.5g sodium acetate 7.5g sodium acetate 7.5g sodium acetate 245g dist. water 245g dist. water 245g dist. water 79.5g 2-propanol 79.5g 2-propanol 87.5g Crodet S40 59g Crodet® S40
- Experiment 1 describes the unacceptable result of a non-inventive experiment according to the prior art. A doubling of the amount of surfactant of both Renex types does not lead to a prevention of precipitation (Experiment 2, not according to the invention).
- Experiment 3 shows that by incorporating hydrophilic surface-active compounds directly into the formulation according to the invention precipitation is reliably prevented. This also applies to a partial subsequent addition according to the invention (Experiment 4) or complete addition according to the invention (Experiment 5) to this hydrophilic surface-active compound.
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Abstract
Description
Die Erfindung betrifft neue Formulierungen auf Basis von quaternierten Aminoalkylsiliconen bzw. -siloxanen, Verfahren zur Herstellung dieser Formulierungen und deren Verwendung als Textilhilfsmittel zur Ausrüstung von Textilmaterialien.The invention relates to novel formulations based on quaternized aminoalkyl silicones or siloxanes, processes for the preparation of these formulations and their use as textile auxiliaries for finishing textile materials.
Silikonweichmacher werden vielfältig zur Ausrüstung von Textilmaterialien eiligesetzt. Für den praktischen Einsatz der Silikonweichnacheremulsionen sind Anforderungen wie Lagerstabilität, Temperaturstabilität, Resistenz gegenüber Weißtönern und anderen anionischen Textilhilfsmitteln, Resistenz gegen pH-Wert Änderungen und Salzzusatz und gegen die Einwirkung mechanischer Energie von zentraler Bedeutung. Besonders die Stabilität gegen die Einwirkung mechanischer Energie, die Scherstabilität oder Jetstabilität, bereitet Silikonweichmacheremulsionen unter Praxisbedingungen oftmals große Schwierigkeiten (vgl. R. Zyschka, Melliand Textilberichte 6/2001, 497).Silicone softeners are widely used for finishing textile materials. Requirements such as storage stability, temperature stability, resistance to whiteners and other anionic textile auxiliaries, resistance to changes in pH and salt addition and against the action of mechanical energy are of central importance for the practical use of the silicone softener emulsions. In particular, the stability against the action of mechanical energy, the shear stability or jet stability, often causes great difficulties for silicone softener emulsions under practical conditions (see R. Zyschka, Melliand Textilberichte 6/2001, 497).
Microemulsionen bieten grundsätzlich den Vorteil der thermodynamischen Stabilität. In einer Vielzahl von Veröffentlichungen ist das Gleichgewichtsphasenverhalten in Abhängigkeit von der Struktur des zu emulgierenden Öls und der/des Tenside/s behandelt worden. Systematisch ist ebenfalls der Zusatz von anorganischen Salzen studiert worden (vgl.
Hinsichtlich der weichmachenden Komponenten sind Kombinationen von kohlenwasserstoffbasierten Quats mit Silikonquats (
Zur Verbesserung der Hydrophilie werden die weithin benutzten Aminoalkylsiloxanöle zunehmend durch polyethermodifizierte Aminoalkylsiloxanöle ersetzt (vgl.
Eine zusätzliche Einführung von Alkoxysilylstrukturen in polyether- und aminosubstituierte Silikone ist ebenfalls vorgeschlagen worden (
Echte permanent-hydrophile Textilweichmacher auf Silikonquatbasis sind schließlich in
Feinteilige Microemulsionen von Aminoalkylsiloxanen sollen in einem Zweistufenprozess durch Herstellung eines Konzentrates aus Aminoalkylsiloxan, silikonunlöslichem Tensid und wenig Wasser mit anschließendem schnellen Einrühren in Wasser zugänglich sein (
Gemäß
Gemäß
Mechanische Stabilität von Aminosiloxanmicroemulsionen soll auch durch Anwendung von Betainen ggf. in Kombination mit nichtionogenen Tensiden des HLB Bereiches 5 bis 16 erreicht werden können (vgl.
In der Färbetechnik ist bekannt, komplexe Mischungen, die sulfonierte Alkylnaphthylderivate und halogenierte Kohlenwasserstoffe enthalten, als jetstabile Anfärbebeschleunigerformulierungen zu benutzen (
Derartige sulfonierte Naphthylderivate in Kombination mit Fettalkoholethoxylaten sind ebenfalls zur Stabilisierung von tintenstrahltauglichen Formulierungen vorgeschlagen worden (
Schließlich ist noch bekannt, dass Salze starker Säuren, z.B. Al2(SO4)3 x 18 H2O, die Protonierung kationischer Farbstoffe in Thermotransferdruckpasten sichern, gleichzeitig aber deren Stabilität beeinträchtigen (vgl.
Weiterhin sind aus derFurthermore, from the
Allen zitierten Vorschlägen ist gemein, dass sie keine Hinweise auf Maßnahmen enthalten, wie Emulsionen bzw. Mikroemulsionen von silikonbasierten Textilweichmachern, vorzugsweise Aminosiloxanen und quaternierten Aminoalkylsiloxanen (Silikonquats), gegen die Einwirkung von hohem mechanischem Energieeintrag der modernen Jetsysteme in Kombination mit stark schwankenden Flottenverhältnissen und den Einfluss variierender Vorbehandlungspräparationen der Fasern sicher stabilisiert werden können. Weiterhin sind aus dem Stand der Technik keine Maßnahmen bekannt, wie die gleichzeitig auftretende hohe Schaumneigung (zieht Fleckenbildung nach sich) von Textilweichmacher-Formulierungen bei hohem mechanischem Energieeintrag begrenzt werden kann.All quoted proposals have in common that they contain no evidence of measures, such as emulsions or microemulsions of silicone-based fabric softeners, preferably aminosiloxanes and quaternized aminoalkylsiloxanes (Silikonquats), against the effect of high mechanical energy input of modern jet systems in combination with highly fluctuating liquor ratios and the Influence of varying pretreatment preparations of the fibers can be safely stabilized. Furthermore, no measures are known from the state of the art, as the simultaneously occurring high foam tendency (attracts staining) by textile softener formulations can be limited at high mechanical energy input.
Es war somit Aufgabe der vorliegenden Erfindung, Maßnahmen zu beschreiben, wie Emulsionen bzw. Microemulsionen von silikonbasierten Textilweichmachern, vorzugsweise quaternierten Aminoalkylsiloxanen (Silikonquats), bei Einwirkung von hohem Energieeintrag (extrem hoher Scherkräfte bei modernen Jetsystemen) in Kombination mit stark schwankenden Flottenverhältnissen und dem Einfluss variierender Vorbehandlungspräparationen sicher stabilisiert werden können und gleichzeitig die Schaumneigung begrenzt werden kann.It was therefore an object of the present invention to describe measures such as emulsions or microemulsions of silicone-based textile softeners, preferably quaternized aminoalkylsiloxanes (silicone quats), when exposed to high energy input (extremely high shear forces in modern jet systems) in combination with highly fluctuating liquor ratios and the influence varying pretreatment preparations can be safely stabilized and at the same time the foaming tendency can be limited.
Es wurde überraschend gefunden, dass durch die Kombination von quaternierten Aminoalkylsiloxanen mit stark hydrophilen nichtionogenen grenzflächenaktiven Verbindungen (Tensiden) diese Aufgabe gelöst werden kann.It has surprisingly been found that this object can be achieved by the combination of quaternized aminoalkylsiloxanes with strongly hydrophilic nonionic surface-active compounds (surfactants).
Die vorliegende Erfindung begriff daher Formulierungen wie in den Ansprüchen 1 bis 9 definiert, deren Verwendung sowie Verfahren zur ihrer Herstellung.The present invention therefore understood formulations as defined in claims 1 to 9, their use and processes for their preparation.
Bevorzugte hydrophile, nichtionogenen grenzflächenaktive Verbindungen (a) im Sinne der Erfindung sind Substanzen, die die Oberflächenspannung von Wasser auf unter 45 mN/m absenken. Es handelt sich um Ethylen/Propylenoxid (EO/PO) modifizierte Verbindungen, gegebenenfalls ungesättigt und/oder verzweigt, aus der Gruppe der Fettalkohole, Fettsäuren, Alkohole, Säuren, Alkylarylderivate, Fettamine, Glyceride und Sorbitanester, bei denen die Anzahl der EO/PO Einheiten zwischen 15 und 150 liegt, wobei das Verhältnis von PO Einheiten zu EO-Einheiten bei 0,25 oder unter 0,25 liegt, und bei denen die Anzahl der Ethylenoxideinheiten (EO-Teil) größer oder gleich der Anzahl der Kohlenstoffatome im Nicht-EO Teil ist, und um Alkylpolyglykoside, Ethylenoxid/Propylenoxid Copolymere und Polyethersiloxane.Preferred hydrophilic, non-ionic surface-active compounds (a) according to the invention are substances which lower the surface tension of water below 45 mN / m. These are ethylene / propylene oxide (EO / PO) modified compounds, optionally unsaturated and / or branched, from the group of fatty alcohols, fatty acids, alcohols, acids, alkylaryl derivatives, fatty amines, glycerides and sorbitan esters in which the number of EO / PO Is between 15 and 150, with the ratio of PO units to EO units being 0.25 or less than 0.25, and where the number of ethylene oxide (EO) units is greater than or equal to the number of carbon atoms in the non-electronic EO is part, and to alkyl polyglycosides, ethylene oxide / propylene oxide copolymers and polyether siloxanes.
Speziell handelt es sich bei den Verbindungen (a) um solche der Formeln
R1-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E (1),
R2-NH-[CH2CH(CH3)O]r-[CH2CH2O]q-E (3),
R2-NH-CH(CH3)CH2-[OCH2CH(CH3)]m-[OCH2CH2]q-O-E (6),
R2-NH-CH(CH3)CH2-[OCH2CH(CH3)]m7-[OCH2CH2]q-[OCH2CH(CH3)]m8-NH-R2 (7),
E-O-[CH2CH2O]s-[CH2CH(CH3)O]t-E (8),
oder ein Polyethersiloxan (9)
- E
- für einen Rest R1, Wasserstoff, geradkettiges oder verzweigtes, gesättigtes oder ein- oder mehrfach ungesättigtes C1-C18-Alkyl, welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist, oder für C5-C10-Cycloalkyl steht, welches gegebenenfalls ein- oder mehrfach durch C1-C4-Akyl, -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R1
- für geradkettiges oder verzweigtes, gesättigtes oder ungesättigtes C8-C40- Alkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebe- nenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Allcoxycarb- onyl oder Carbonyl, Amino, mono- oder di- C1-C4-AlKylamino substituiert ist, oder für C5-C10-Cycloalkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebenenfalls ein- oder mehrfach durch C1-C4-Alkyl, -OH, C1- C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl, Amino, mono- oder di-C1- C4-Alkylamino substituiert ist,
- R2
- für geradkettiges oder verzweigtes, gesättigtes oder ein- bis mehrfach unge- sättigtes C8-C40-Alkyl steht, welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R3
- für geradkettiges oder verzweigtes C1-C26 Alkyl oder C6-C10-Aryl steht, -CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E ,
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
-CH2CH2CH2-O-CH2CHOHCH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
-Z-[CH2CH2O]q-[CH2CH(CH3)O]r-E
wobei - Z
- ein geradkettiger oder verzweigter Alkyl- oder Cycloalkylrest ist, der jeweils durch -O- und /oder -CO- unterbrochen und gegebenenfalls durch mindestens eine OH-Gruppe substituiert sein kann
- q
- für 15 bis 150 steht,
wobei die Summe von q1 + q2 = q ist,
q3, q4, q5 und q6 unabhängig voneinander für 0 bis 150 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist,
- r
- für 0 bis 50 steht,
wobei die Summe von r1 + r2 = r ist,
r3, r4, r5 und r6 unabhängig voneinander für 0 bis 50 stehen,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist,
- m
- für 1 bis 50 steht,
wobei 2 ≤ m7+m8, und die Summe von m7 + m8 = m+1 ist, und
das Verhältnis von q : m ≥ 4 ist,
- s
- für 5 bis 150 steht,
- t
- für 5 bis 150 steht,
0 ≤ z1 ≤ 2000
mindestens ein R4 ≠ R3, und
0,01 ≤ Σ Alkylreste R3 : Σ q+r ≤ 1.Specifically, the compounds (a) are those of the formulas
R 1 is -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E (1)
R 2 -NH- [CH 2 CH (CH 3 ) O] r - [CH 2 CH 2 O] q -E (3)
R 2 -NH-CH (CH 3 ) CH 2 - [OCH 2 CH (CH 3 )] m - [OCH 2 CH 2 ] q -OE (6)
R 2 -NH-CH (CH 3) CH 2 - [OCH 2 CH (CH 3)] m7 - [OCH 2 CH 2] q - [OCH 2 CH (CH 3)] m8 -NH-R 2 (7) .
EO- [CH 2 CH 2 O] s - [CH 2 CH (CH 3 ) O] t -E (8),
or a polyether siloxane (9)
- e
- for a radical R 1 , hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C 1 -C 18 -alkyl, which may be mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 Alkoxycarbonyl or carbonyl, or represents C 5 -C 10 -cycloalkyl which is optionally mono- or polysubstituted by C 1 -C 4 -alkyl, -OH, C 1 -C 4 -alkoxy, C 1 -C 4 - Alkoxycarbonyl or carbonyl is substituted,
- R 1
- is straight-chain or branched, saturated or unsaturated C 8 -C 40 -alkyl whose alkyl chain is optionally interrupted one or more times by oxygen and / or nitrogen atoms and which, if appropriate, mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, amino, mono- or di-C 1 -C 4 -alkylamino, or represents C 5 -C 10 -cycloalkyl, the alkyl chain of which may be on or is interrupted several times by oxygen and / or nitrogen atoms and which optionally mono- or polysubstituted by C 1 -C 4 alkyl, -OH, C 1 - C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or carbonyl, amino, mono - or di-C 1 - C 4 alkylamino is substituted,
- R 2
- is straight-chain or branched, saturated or mono- to polyunsaturated C 8 -C 40 -alkyl which is optionally mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl is substituted,
- R 3
- represents straight-chain or branched C 1 -C 26 -alkyl or C 6 -C 10 -aryl, -CH 2 CH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E,
-CH 2 CH 2 CH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E
-CH 2 CH 2 CH 2 -O-CH 2 CHOHCH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E
-Z- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E
in which - Z
- a straight-chain or branched alkyl or cycloalkyl radical which may each be interrupted by -O- and / or -CO- and may optionally be substituted by at least one OH group
- q
- stands for 15 to 150,
where the sum of q1 + q2 = q,
q3, q4, q5 and q6 independently represent 0 to 150,
where the sum of q3 + q4 + q5 + q6 = q,
- r
- stands for 0 to 50,
where the sum of r1 + r2 = r,
r3, r4, r5 and r6 independently represent 0 to 50,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25,
- m
- stands for 1 to 50,
where 2 ≤ m7 + m8, and the sum of m7 + m8 = m + 1, and
the ratio of q: m ≥ 4,
- s
- stands for 5 to 150,
- t
- stands for 5 to 150,
0 ≤ z1 ≤ 2000
at least one R4 ≠ R3, and
0.01 ≤ Σ alkyl radicals R 3 : Σ q + r ≤ 1.
Speziell handelt es sich bei den Verbindungen (a) auch um solche der Formeln (1') bis (9')
die in den Formeln (1')-(8') dargestellten Klammerausdrücke "{" und "}" bedeuten, das die innerhalb dieser Klammerausdrücke stehenden Ethylenoxid- bzw. Propylenoxid-Einheiten entweder wie dargestellt blockweise angeordnet sein können oder aber auch beliebig statistisch angeordnet sein können,
- E
- für einen Rest R1, Wasserstoff, geradkettiges oder verzweigtes, gesättigtes oder ein- oder mehrfach ungesättigtes C1-C18-Alkyl welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist, oder für C5-C10-Cycloalkyl steht, welches jeweils gegebenenfalls ein- oder mehrfach durch C1-C4-Alkyl, -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R1
- für geradkettiges oder verzweigtes, gesättigtes oder ungesättigtes C8-C40- Alkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebe- nenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarb- onyl oder Carbonyl, Amino, mono- oder di- C1-C4-Alkylamino substituiert ist, oder für C5-C10-Cycloalkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebenenfalls ein- oder mehrfach durch C1-C4-Alkyl, -OH, C1- C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl, Amino, mono- oder di-C1- C4-Alkylamino substituiert ist, oder für C6-C10 Aryl steht, welches gegebenfalls substituiert, insbesondere durch C3-C15-Alkyl substituiert ist.
- R2
- für geradkettiges oder verzweigtes, gesättigtes oder ein- bis mehrfach unge- sättigtes C8-C40-Alkyl steht, welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R3
- für geradkettiges oder verzweigtes C1-C26 Alkyl oder C6-C10-Aryl steht,
- R4 für R3
- oder für einen Rest der Formeln
Z ein geradkettiger oder verzweigter Alkyl- oder Cycloalklyrest ist, der jeweils durch -O- und /oder -CO- unterbrochen und gegebenenfalls durch mindestens eine OH-Gruppe subsituiert
wobei die in den vorgenannten Formeln dargestellten Klammerausdrücke "{" " und "}" wiederum bedeuten, dass die innerhalb dieser Klammerausdrücke stehenden Ethylenoxid- bzw. Propylenoxid-Einheiten entweder wie dargestellt blockweise angeordnet sein können oder aber auch beliebig statistisch angeordnet sein können,
- q
- für 15 bis 150 steht,
wobei die Summe von q1 + q2 = q ist,
q3, q4, q5 und q6 unabhängig voneinander für 0 bis 150 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist,
- r
- für 0 bis 50 steht,
wobei die Summe von r1 + r2 = r ist,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist,
- m
- für 1 bis 50 steht,
wobei 2 ≤ m7+m8, und
das Verhältnis von q : m ≥ 4 ist,
- s
- für 5 bis 150, bevorzugt 15-150 steht,
- t
- für 0 bis 150, bevorzugt 5 bis 150 und insbesondere 5 bis 20 steht,
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
mindestens ein R4 ≠ R3, und für Formel (9') gilt:
0,01 ≤ Σ Alkylreste R3 : Σq ≤ 1.Specifically, the compounds (a) are also those of the formulas (1 ') to (9')
the parentheses "{" and "}" in formulas (1 ') - (8') mean that the ethylene oxide or propylene oxide units within these parentheses can either be arranged blockwise as shown, or randomly arranged as desired could be,
- e
- a radical R 1 , hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C 1 -C 18 -alkyl which may be mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 - Alkoxycarbonyl or carbonyl is substituted, or is C 5 -C 10 -cycloalkyl, each of which is optionally mono- or polysubstituted by C 1 -C 4 -alkyl, -OH, C 1 -C 4 -alkoxy, C 1 -C 4 - Alkoxycarbonyl or carbonyl is substituted,
- R 1
- is straight-chain or branched, saturated or unsaturated C 8 -C 40 -alkyl whose alkyl chain is optionally interrupted one or more times by oxygen and / or nitrogen atoms and which is optionally mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, amino, mono- or di-C 1 -C 4 -alkylamino, or for C 5 C 10 -cycloalkyl whose alkyl chain is optionally interrupted one or more times by oxygen and / or nitrogen atoms and which is optionally mono- or polysubstituted by C 1 -C 4 -alkyl, -OH, C 1 - C 4 -alkoxy, C 1 -C 4 alkoxycarbonyl or carbonyl, amino, mono- or di-C 1 - C 4 alkylamino, or is C 6 -C 10 aryl which optionally substituted, in particular by C 3 -C 15 alkyl is substituted.
- R 2
- is straight-chain or branched, saturated or mono- to polyunsaturated C 8 -C 40 -alkyl which is optionally mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl is substituted,
- R 3
- represents straight-chain or branched C 1 -C 26 -alkyl or C 6 -C 10 -aryl,
- R 4 for R 3
- or for a remainder of the formulas
Z is a straight-chain or branched alkyl or cycloalkyl radical which is interrupted in each case by -O- and / or -CO- and optionally substituted by at least one OH group
the parentheses "{""and"}"shown in the above formulas again mean that the ethylene oxide or propylene oxide units within these parentheses can either be arranged blockwise as shown or else arranged randomly as desired,
- q
- stands for 15 to 150,
where the sum of q1 + q2 = q,
q3, q4, q5 and q6 independently represent 0 to 150,
where the sum of q3 + q4 + q5 + q6 = q,
- r
- stands for 0 to 50,
where the sum of r1 + r2 = r,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25,
- m
- stands for 1 to 50,
where 2 ≤ m7 + m8, and
the ratio of q: m ≥ 4,
- s
- is from 5 to 150, preferably 15-150,
- t
- is 0 to 150, preferably 5 to 150 and in particular 5 to 20,
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
at least one R4 ≠ R3, and for formula (9 '):
0.01 ≤ Σ alkyl radicals R 3 : Σq ≤ 1.
Insbesondere handelt es sich bei den Verbindungen (a) um solche der Formeln (1) bis (9), worin
- E
- für Wasserstoff, geradkettiges oder verzweigtes, gesättigtes oder ein- oder mehrfach ungesättigtes C1-C4-Alkyl welches gegebenenfalls 1 bis zweifach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist, oder für C5-C6 -Cycloalkyl steht, welches jeweils gegebenenfalls ein- bis mehrfach durch C1-C4-Alkyl, -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R1
- für geradkettiges oder verzweigtes, gesättigtes oder ungesättigtes C10-C36- Alkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebe- nenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarb- onyl oder Carbonyl, Amino, mono- oder di- C1-C4-Alkylamino substituiert ist, oder für C5-C6-Cycloalkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebenenfalls ein- oder mehrfach durch C1-C4-Alkyl, -OH, C1- C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl, Amino, mono- oder di-C1- C4-Alkylamino substituiert ist,
- R2
- für geradkettiges oder verzweigtes, gesättigtes oder ein- bis mehrfach unge- sättigtes C10-C36-Alkyl steht, welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R3
- für geradkettiges oder verzweigtes C1-C18 -Alkyl oder C6-C10-Aryl steht,
- R4
- für einen Rest R3 oder für einen Rest der Formeln
oder
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
steht,
q für 20 bis 100 steht, q1 und q2 unabhängig voneinander für 20 bis 100 stehen,
wobei die Summe von q1 + q2 = q ist,
q3, und q6 unabhängig voneinander für 20 bis 100 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist,
r für 0 bis 20 steht, r1 und r2 unabhängig voneinander für 0 bis 20 stehen,
wobei die Summe von r1 + r2 = r ist,
r3, r4, r5 und r6 unabhängig voneinander für 0 bis 20 stehen,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist,
m für 1 bis 7 steht. m7 und m8 unabhängig voneinander für1 bis 7 stehen,
wobei 2 ≤ m7+m8, und die Summe von m7 + m8 = m +1 ist, und
das Verhältnis von q : m ≥ 4 ist,
s für 5 bis 100 steht,
t für 5 bis 100 steht, wobei 0.05 ≤ s : t ≤ 20,
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
mindestens ein R4 ≠ R3,
und
0,01 ≤ Σ Alkylreste R3: Σ q+r ≤ 0,5.
- e
- is hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C 1 -C 4 -alkyl which is optionally substituted once to twice by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, or is C 5 -C 6 -cycloalkyl, which is in each case optionally mono- to polysubstituted by C 1 -C 4 -alkyl, -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl,
- R 1
- is straight-chain or branched, saturated or unsaturated C 10 -C 36 -alkyl whose alkyl chain is optionally interrupted one or more times by oxygen and / or nitrogen atoms and which optionally one or more times by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, amino, mono- or di-C 1 -C 4 -alkylamino, or represents C 5 -C 6 -cycloalkyl, the alkyl chain of which may be on or is interrupted several times by oxygen and / or nitrogen atoms and which optionally mono- or polysubstituted by C 1 -C 4 alkyl, -OH, C 1 - C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or carbonyl, amino, mono - or di-C 1 - C 4 alkylamino is substituted,
- R 2
- is straight-chain or branched, saturated or mono- to polyunsaturated C 10 -C 36 -alkyl which is optionally mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl is substituted,
- R 3
- represents straight-chain or branched C 1 -C 18 -alkyl or C 6 -C 10 -aryl,
- R 4
- for a radical R 3 or for a radical of the formulas
or
-CH 2 CH 2 CH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E
stands,
q is from 20 to 100, q1 and q2 are each independently from 20 to 100,
where the sum of q1 + q2 = q,
q3, and q6 are independently from 20 to 100,
where the sum of q3 + q4 + q5 + q6 = q,
r is 0 to 20, r1 and r2 independently represent 0 to 20,
where the sum of r1 + r2 = r,
r3, r4, r5 and r6 independently represent 0 to 20,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25,
m stands for 1 to 7. m7 and m8 independently represent 1 to 7,
where 2 ≤ m7 + m8, and the sum of m7 + m8 = m + 1, and
the ratio of q: m ≥ 4,
s stands for 5 to 100,
t is 5 to 100, where 0.05 ≤ s: t ≤ 20,
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
at least one R4 ≠ R3,
and
0.01 ≤ Σ alkyl radicals R 3 : Σ q + r ≤ 0.5.
Insbesondere handelt es sich bei den Verbindungen (a) auch um solche der Formeln (1') bis (9'), worin
- E
- für Wasserstoff, geradkettiges oder verzweigtes, gesättigtes oder ein- oder mehrfach ungesättigtes C1-C4-Alkyl welches gegebenenfalls 1 bis zweifach durch -OH, C1-C4-Alkoxy, C1-C4-Akoxycarbonyl oder Carbonyl substituiert ist, oder für C5-C6 -Cycloalkyl steht, welches jeweils gegebenenfalls ein- bis mehrfach durch C1-C4-Alkyl, -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R1
- für geradkettiges oder verzweigtes, gesättigtes oder ungesättigtes C10-C36- Alkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebe- nenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarb- onyl oder Carbonyl, Amino, mono- oder di- C1-C4-Alkylamino substituiert ist, oder für C5-C6-Cycloalkyl steht, dessen Alkylkette gegebenenfalls ein- oder mehrfach durch Sauerstoff- und/oder Stickstoffatome unterbrochen ist und welches gegebenenfalls ein- oder mehrfach durch C1-C4-Alkyl, -OH, C1- C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl, Amino, mono- oder di-C1- C4-Alkylamino substituiert ist, oder für C6-C10 Aryl steht, welches gegebenfalls substituiert, insbesondere durch C3-C15-Alkyl substituiert ist.
- R2
- für geradkettiges oder verzweigtes, gesättigtes oder ein- bis mehrfach unge- sättigtes C10-C36-Alkyl steht, welches gegebenenfalls ein- oder mehrfach durch -OH, C1-C4-Alkoxy, C1-C4-Alkoxycarbonyl oder Carbonyl substituiert ist,
- R3
- für geradkettiges oder verzweigtes C1-C18 -Alkyl oder C6-C10-Aryl steht,
- R4
- für einen Rest R3 oder für einen Rest der Formeln
- q
- für 20 bis 100 steht,
q1 und q2 unabhängig voneinander für 20 bis 100 stehen,
wobei die Summe von q1 + q2 = q ist,
q3, q4, q5 und q6 unabhängig voneinander für 20 bis 100 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist,
r für 0 bis 20 steht, r1 und r2 unabhängig voneinander für 0 bis 20 stehen,
wobei die Summe von r1 + r2 = r ist,
r3, r4, r5 und r6 unabhängig voneinander für 0 bis 20 stehen,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist,
m für 1 bis 7 steht, m7 und m8 unabhängig voneinander für1 bis 7 stehen,
wobei 2 ≤ m7+m8, und
das Verhältnis von q : m ≥ 4 ist,
s für 5 bis 100, bevorzugt 15 bis 100 steht,
t für 5 bis 100, bevorzugt 5 bis 20 steht, wobei t: s ≤ 0,25
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
mindestens ein R4 ≠ R3,
und für die Formel (9') gilt:
0,01 ≤ Σ Alkykeste R3: Σ q ≤ 0,5.
- e
- is hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C 1 -C 4 -alkyl which is optionally substituted once to twice by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, or is C 5 -C 6 -cycloalkyl, which in each case optionally one to is monosubstituted by C 1 -C 4 -alkyl, -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl,
- R 1
- is straight-chain or branched, saturated or unsaturated C 10 -C 36 -alkyl whose alkyl chain is optionally interrupted one or more times by oxygen and / or nitrogen atoms and which optionally one or more times by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl, amino, mono- or di-C 1 -C 4 -alkylamino, or represents C 5 -C 6 -cycloalkyl, the alkyl chain of which may be on or is interrupted several times by oxygen and / or nitrogen atoms and which optionally mono- or polysubstituted by C 1 -C 4 alkyl, -OH, C 1 - C 4 alkoxy, C 1 -C 4 alkoxycarbonyl or carbonyl, amino, mono - or di-C 1 - C 4 alkylamino substituted, or is C 6 -C 10 aryl, which is optionally substituted, in particular substituted by C 3 -C 15 alkyl.
- R 2
- is straight-chain or branched, saturated or mono- to polyunsaturated C 10 -C 36 -alkyl which is optionally mono- or polysubstituted by -OH, C 1 -C 4 -alkoxy, C 1 -C 4 -alkoxycarbonyl or carbonyl is substituted,
- R 3
- represents straight-chain or branched C 1 -C 18 -alkyl or C 6 -C 10 -aryl,
- R 4
- for a radical R 3 or for a radical of the formulas
- q
- stands for 20 to 100,
q1 and q2 are independently from 20 to 100,
where the sum of q1 + q2 = q,
q3, q4, q5 and q6 are independently from 20 to 100,
where the sum of q3 + q4 + q5 + q6 = q,
r is 0 to 20, r1 and r2 independently represent 0 to 20,
where the sum of r1 + r2 = r,
r3, r4, r5 and r6 independently represent 0 to 20,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25,
m is 1 to 7, m7 and m8 are independently from 1 to 7,
where 2 ≤ m7 + m8, and
the ratio of q: m ≥ 4,
s is from 5 to 100, preferably from 15 to 100,
t is 5 to 100, preferably 5 to 20, where t: s ≤ 0.25
0 ≤ z1 ≤ 2000
0 ≤ z2 ≤ 2000
at least one R4 ≠ R3,
and for the formula (9 '):
0.01 ≤ Σ alkyl radicals R 3 : Σ q ≤ 0.5.
Besonders bevorzugt handelt es sich bei den Verbindungen (a) um solche der Formeln (1) bis (9), worin
- E
- für H-, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2- oder CH3C(O)-
- R1
- für einen Rest der Formeln
CH3(CH2)n1-
CH3(CH2)7CH=CH(CH2)8-
mit
n1 = 9 bis 23,
n2 = 3 bis 23,
n3 = 0 bis 18,
n4 = 7 bis 23,
n5 = 3 bis 15,
steht, - R2
- für einen Rest der Formeln
n6 = 8 bis bis 28,
steht, - R3
- für C1-C18 -Alkyl oder C6-C10-Aryl steht,
- R4
- für einen Rest R3 oder für einen Rest der Formeln
-CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E,
oder
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
steht, - q
- für 25 bis 60 steht,
q1 und q2 unabhängig voneinander für 25 bis 60 stehen,
q3, q4, q5 und q6 unabhängig voneinander für 25 bis 60 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist, - r
- für 0 bis 10 steht,
r1 und r2 unabhängig voneinander für 0 bis 10 stehen,
wobei die Summe von r1 + r2 = r ist,
r3, r4, r5 und r6 unabhängig voneinander für 0 bis 10 stehen,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist, und
0,01 ≤ Σ Alkylreste R3 : Σ q+r ≤ 0,1
- e
- for H, CH 3 -, CH 3 CH 2 -, CH 3 CH 2 CH 2 -, (CH 3 ) 2 CH-, CH 3 CH 2 CH 2 CH 2 - or CH 3 C (O) -
- R 1
- for a rest of the formulas
CH 3 (CH 2) n1 -
CH 3 (CH 2 ) 7 CH = CH (CH 2 ) 8 -
With
n1 = 9 to 23,
n2 = 3 to 23,
n3 = 0 to 18,
n4 = 7 to 23,
n5 = 3 to 15,
stands, - R 2
- for a rest of the formulas
n6 = 8 to 28,
stands, - R 3
- is C 1 -C 18 -alkyl or C 6 -C 10 -aryl,
- R 4
- for a radical R 3 or for a radical of the formulas
-CH 2 CH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E,
or
-CH 2 CH 2 CH 2 -O- [CH 2 CH 2 O] q - [CH 2 CH (CH 3 ) O] r -E
stands, - q
- stands for 25 to 60,
q1 and q2 independently represent 25 to 60,
q3, q4, q5 and q6 independently of one another represent 25 to 60,
where the sum of q3 + q4 + q5 + q6 = q, - r
- stands for 0 to 10,
r1 and r2 independently represent 0 to 10,
where the sum of r1 + r2 = r,
r3, r4, r5 and r6 independently represent 0 to 10,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25, and
0.01 ≤ Σ alkyl radicals R 3 : Σ q + r ≤ 0.1
Besonders bevorzugt handelt es sich bei den Verbindungen (a) auch um solche der Formeln (1') bis (9'), worin
- E
- für H-, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2- oder CH3C(O)-
steht, - R1
- für einen Rest der Formeln
CH3(CH2)n1-
CH3(CH2)7CH=CH(CH2)8-
mit
n1 = 9 bis 23,
n2 = 3 bis 23, bevorzugt 6 bis 23
n3 = 0 bis 18, wobei bevorzugt n2+ n3 ≤ 31 ist,
n4 = 7 bis 23,
n5 = 3 bis bis 15,
steht, - R2
- für einen Rest der Formeln
n6 = 8 bis bis 28,
steht, - R3
- für C1-C18 -Alkyl oder C6-C10-Aryl steht,
- R4
- für einen Rest R3 oder für einen Rest der Formeln
- q
- für 25 bis 60 steht,
q1 und q2 unabhängig voneinander für 25bis 60 stehen,
q3, q4, q5 und q6 unabhängig voneinander für 25 bis 60 stehen,
wobei die Summe von q3 + q4 + q5 + q6 = q ist, - r
- für 0 bis 10 steht,
wobei die Summe von r1 + r2 = r ist,
r3, r4, r5 und r6 unabhängig voneinander für 0 bis 10 stehen,
wobei die Summe von r3 + r4 + r5 + r6 = r ist, und
das Verhältnis von r : q ≤ 0.25 ist, und
für die Formel (9') gilt:
- e
- for H, CH 3 -, CH 3 CH 2 -, CH 3 CH 2 CH 2 -, (CH 3 ) 2 CH-, CH 3 CH 2 CH 2 CH 2 - or CH 3 C (O) -
stands, - R 1
- for a rest of the formulas
CH 3 (CH 2) n1 -
CH 3 (CH 2 ) 7 CH = CH (CH 2 ) 8 -
With
n1 = 9 to 23,
n 2 = 3 to 23, preferably 6 to 23
n3 = 0 to 18, where preferably n2 + n3 ≤ 31,
n4 = 7 to 23,
n5 = 3 to 15,
stands, - R 2
- for a rest of the formulas
n6 = 8 to 28,
stands, - R 3
- is C 1 -C 18 -alkyl or C 6 -C 10 -aryl,
- R 4
- for a radical R 3 or for a radical of the formulas
- q
- stands for 25 to 60,
q1 and q2 independently represent 25 to 60,
q3, q4, q5 and q6 independently of one another represent 25 to 60,
where the sum of q3 + q4 + q5 + q6 = q, - r
- stands for 0 to 10,
where the sum of r1 + r2 = r,
r3, r4, r5 and r6 independently represent 0 to 10,
where the sum of r3 + r4 + r5 + r6 = r, and
the ratio of r: q ≤ 0.25, and
for the formula (9 '):
Ganz besonders bevorzugt sind erfindungsgemäße Formulierungen, die als Verbindung (a) den Ester aus Stearinsäure und 40 mol EO enthalten.Very particular preference is given to formulations according to the invention which contain, as compound (a), the ester of stearic acid and 40 mol of EO.
Die erfindungsgemäßen Formulierungen enthalten mindestens eine am Stickstoff quaternierte Aminoalkylsiloxan-Verbindung (Silikonquat). Derartige Verbindungen und deren Herstellung sind bekannt, z.B. aus
Die in den erfindungsgemäßen Formulierungen enthaltenen quaternierten Aminoalkylsiloxan-Verbindungen sind linear oder cyclisch Polysiloxanpolymere der 
- X
- ein zweiwertiger Kohlenwasserstoffrest mit mindestens 4 Kohlenstoffatomen ist, der eine Hydroxylgruppe aufweisen kann und bevorzugt eine Hydroxylgruppe aufweist und der durch ein Sauerstoffatom unterbrochen sein kann, und die Gruppen X in den Wiederholungseinheiten gleich oder verschieden sein können,
- Y
- ein zweiwertiger Kohlenwasserststoffrest mit mindestens 2 Kohlenstoffatom- men ist, der eine Hydroxylgruppe aufweisen und der durch ein oder mehrere Sauerstoff- oder Stickstoffatome unterbrochen sein kann,
- R11, R12, R13 und R14
- gleich oder verschieden sind und Alkylreste mit 1 bis 4 Koh- lenstoffatomen oder Benzylreste bedeuten oder jeweils die Reste R11 und R13 oder R12 und R14 Bestandteile eines verbrückenden Alkylenrestes sein können,
- R16
- H oder ein Alkylrest mit 1 bis 20 Kohlenstoffatomen ist, der sauerstoffsub- stituiert sein kann,
- M
- die Struktur -B-O-(EOx)v(POx)w-B-, worin EOx eine Ethylenoxideinheit und POx eine Propylenoxideinheit ist,
- B
- gradkettiges oder verzweigtes C2 bis C6 Alkylen,
- v
- 0 bis 200,
- w
- 0 bis 200,
- v+w ≥
- 1 entspricht,
- n
- 2 bis 1000, worin die n in den Wiederholungseinheiten gleich oder verschieden sein können, und
- A-
- ein anorganisches oder organisches Anion bedeutet.
- X
- is a divalent hydrocarbon radical having at least 4 carbon atoms, which may have a hydroxyl group and preferably has a hydroxyl group and which may be interrupted by an oxygen atom, and the groups X may be the same or different in the repeating units,
- Y
- is a divalent hydrocarbon radical having at least 2 carbon atoms, which has a hydroxyl group and which may be interrupted by one or more oxygen or nitrogen atoms,
- R 11 , R 12 , R 13 and R 14
- are identical or different and are alkyl radicals having 1 to 4 carbon atoms or benzyl radicals or in each case the radicals R 11 and R 13 or R 12 and R 14 may be constituents of a bridging alkylene radical,
- R 16
- Is H or an alkyl radical of 1 to 20 carbon atoms which may be oxygen-substituted,
- M
- the structure -BO- (EOx) v (POx) w -B-, wherein EOx is an ethylene oxide unit and POx is a propylene oxide unit,
- B
- straight-chain or branched C 2 to C 6 alkylene,
- v
- 0 to 200,
- w
- 0 to 200,
- v + w ≥
- 1 corresponds to
- n
- 2 to 1000, wherein the n in the repeating units may be the same or different, and
- A-
- an inorganic or organic anion.
Die erfindungsgemäßen Formulierungen enthalten gegebenenfalls auch beliebige Mischungen der oben bezeichneten quaternierten Aminoalkylsiloxan-Verbindungen mit den entsprechenden nicht quaternierten Verbindungen. Bei diesen nicht quaternierten Verbindungen fehlt somit in der Formel (10) an den Stickstoffatomen in der Hauptkette jeweils einer der Reste R11 oder R12 bzw. R13 oder R14 If appropriate, the formulations according to the invention also comprise any desired mixtures of the abovementioned quaternized aminoalkylsiloxane compounds with the corresponding nonquaternized compounds. In the case of these non-quaternized compounds, in the formula (10), in each case, one of the radicals R 11 or R 12 or R 13 or R 14 is missing from the nitrogen atoms in the main chain
Die erfindungsgemäß bevorzugten quaternierten Aminoalkylsiloxan-Verbindungen sind Gegenstand der
Die erfindungsgemäßen Formulierungen können neben den Komponenten (a) noch weitere grenzflächenaktive Komponenten (f), die eine Emulgierung bzw. Microemulgierung ermöglichen, enthalten.The formulations according to the invention may contain, in addition to the components (a), further surface-active components (f) which permit emulsification or microemulsification.
Bei diesen Komponenten (f) handelt es sich um übliche, dem Fachmann bekannte Formulierungsagentien zur Herstellung der Silikon(mikro)emulsionen, die jedoch allein nicht gegen hohen Energieeintrag stabil sind. Als solche bevorzugten Komponenten sind f1) bis f6) zu nennen: (f1) Oxalkylierungsprodukte, die durch Alkoxylierung mit Ethylenoxid oder Propylenoxid von Kondensationsprodukten phenolischer OH-gruppenhaltiger Aromaten mit Formaldehyd und NH-funktionellen Gruppen erhältlich sind. f2) nicht-ionische oder ionisch modifizierte Verbindungen aus der Gruppe der Alkoxylate, Alkylolamide, Ester, Aminoxide und Alkylpolyglykoside, insbesondere Umsetzungsprodukte von Alkylenoxiden mit alkylierbaren Verbindungen, wie z.B. Fettalkoholen, Fettaminen, Fettsäuren, Phenolen, Alkylphenolen, Carbonsäureamiden und Harzsäuren. Hierbei handelt es sich z.B. um Ethylenoxidether aus der Klasse der Umsetzungsprodukte von Ethylenoxid mit gesättigten und/oder ungesättigten Fettalkoholen mit 6 bis 25 C-Atomen (kommerziell erhältlich beispielsweise in Form der Produlctreihe Renex®) oder Alkylphenolen mit 4 bis 12 C-Atomen im Alkylrest oder gesättigten und/oder ungesättigten Fettaminen mit 14 bis 20 C-Atomen oder gesättigten und/oder ungesättigten Fettsäuren mit 14 bis 22 C-Atomen oder aus natürlichen oder modifizierten, gegebenenfalls hydrierten Rizinusölfettkörper hergestellte Veresterungs- und/oder Arylierungsprodukte, die gegebenenfalls durch Veresterung mit Dicarbonsäuren zu wiederkehrenden Struktureinheiten verknüpft sind. f3) ionische oder nicht-ionische Verbindungen aus der Gruppe der Umsetzungsprodukte von Alkylenoxid mit Sorbitanester [Tween, ICI], oxalkylierte Acetylendiole und glykole, oxalkylierte Phenole, insbesondere Phenol/Styrol-Polyglylcolether. f4) ionische oder nichtionische polymere oberflächenaktive Mittel aus der Gruppe der Homo- und Copolymerisate, Pfropf- und Pfropfcopolymerisate sowie statistische und lineare Blockcopolymerisate. f5) anionische oberflächenaktive Mittel wie beispielsweise Alkylsulfate, Ethersulfate, Ethercarboxylate, Phosphatester, Sulfosuccinatamide, Paraffinsulfonate, Olefinsulfonate, Sarcosinate, Isothionate und Taurate f6) amphotere oberflächenaktive Mittel wie Betaine und Ampholyte, insbesondere Glycinate, Propionate und Imidazoline.These components (f) are customary formulation agents known to the person skilled in the art for the preparation of the silicone (micro) emulsions, which however are not stable against high energy input alone. Preferred such components are f1) to f6): (f1) oxalkylation products obtainable by alkoxylation with ethylene oxide or propylene oxide of condensation products of phenolic OH group-containing aromatics with formaldehyde and NH-functional groups. f2) nonionic or ionically modified compounds from the group of the alkoxylates, alkylolamides, esters, amine oxides and alkyl polyglycosides, in particular reaction products of alkylene oxides with alkylatable compounds, such as fatty alcohols, fatty amines, fatty acids, phenols, alkylphenols, carboxylic acid amides and resin acids. These are, for example, ethylene oxide from the class of reaction products of ethylene oxide with saturated and / or unsaturated fatty alcohols having 6 to 25 carbon atoms (commercially available, for example in the form of Renex® Produlctreihe) or alkylphenols having 4 to 12 carbon atoms in the alkyl radical or saturated and / or unsaturated fatty amines having 14 to 20 carbon atoms or saturated and / or unsaturated fatty acids having 14 to 22 carbon atoms or esterification and / or arylation products prepared from natural or modified, optionally hydrogenated castor oil, optionally by esterification with Dicarboxylic acids are linked to recurring structural units. f3) ionic or nonionic compounds from the group of the reaction products of alkylene oxide with sorbitan ester [Tween, ICI], alkoxylated acetylenediols and glycol, alkoxylated phenols, in particular phenol / styrene-polyglycol ethers. f4) ionic or nonionic polymeric surfactants from the group of homopolymers and copolymers, graft copolymers and graft copolymers, and also random and linear block copolymers. f5) anionic surfactants such as alkyl sulfates, ether sulfates, ether carboxylates, phosphate esters, sulfosuccinate amides, paraffin sulfonates, olefin sulfonates, sarcosinates, isothionates and taurates f6) amphoteric surfactants such as betaines and ampholytes, especially glycinates, propionates and imidazolines.
Besonders bevorzugte Formulierungsbestandteile (f) sind alkoxylierte Fettalkohole, verzweigte Fettalkohole und Fettsäuren mit 4 bis 14 Alkoxydeinheiten, ganz besonders bevorzugte Formulierungsbestandteile (f) sind alkoxylierte Fettalkohole, verzweigte Fettalkohole mit 6 bis 12 Alkoxydeinheiten, speziell Formulierungen, die den Ether von Tridecylalkohol mit 12 mol EO, den Ether von Tridecylalkohol mit 6 mol EO enthalten.Particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols and fatty acids having 4 to 14 alkoxy units, very particularly preferred formulation components (f) are alkoxylated fatty alcohols, branched fatty alcohols having 6 to 12 alkoxy units, especially formulations containing the ether of tridecyl alcohol with 12 mol EO containing tridecyl alcohol ether with 6 moles of EO.
Die Formulierungsbestandteile werden im allgemeinen in üblichen Mengen der erfindungsgemäßen Formulierung zugesetzt. Bevorzugt werden die Komponenten (f) in Mengen von 1 bis 200 Gew.%, bevorzugt 10 bis 80 Gew.%, besonders bevorzugt 10-50 Gew.-% bezogen auf das quaternierte Aminoalkylsiloxan zugesetzt.The formulation ingredients are generally added in conventional amounts of the formulation of the invention. The components (f) are preferably added in amounts of 1 to 200% by weight, preferably 10 to 80% by weight, particularly preferably 10 to 50% by weight, based on the quaternized aminoalkylsiloxane.
Die Formulierungen können neben der Komponente (a) und den Zusätzen (f) auch noch weitere Hilfsmittel in den für diese Hilfsmittel üblichen Mengen enthalten.In addition to the component (a) and the additives (f), the formulations may also contain further auxiliaries in the amounts customary for these auxiliaries.
Übliche Hilfsmittel im Sinne der Erfindung sind u.a. Egalisiermittel, Netzmittel, Glanzausrüstungsmittel, Faserschutzmittel, Schiebefestmittel und weitere Hilfsmittel nach Stand der Technik. Eine gute Übersicht der erfindungsgemäßen Hilfsmittel findet sich in
Zur Herstellung der erfindungsgemäßen Formulierungen können die quaternierten Aminoalkylsiloxan-Verbindungen mit den Komponenten (a), gegebenenfalls unter Zusatz weiterer, oben genannter Bestandteile, gemischt werden, bevorzugt im Temperaturbereich von 20 bis 90°C, besonders bevorzugt bei 25 bis 70°C, ganz besonders bevorzugt bei 30 bis 60°C.To prepare the formulations according to the invention, the quaternized aminoalkylsiloxane compounds can be mixed with the components (a), if appropriate with the addition of further abovementioned constituents, preferably in the temperature range from 20 to 90.degree. C., more preferably from 25 to 70.degree more preferably at 30 to 60 ° C.
Die quaternierten Aminoalkylsiloxane werden dabei bevorzugt zu der Verbindung (a) gegeben; besonders bevorzugt wird das quaternierte Aminoalkylsiloxan (Silikonquat) vorgelegt und die Emulsionsbildung durch Zugabe der Verbindung (a) und gegebenenfalls weiterer Zusätze vervollständigt.The quaternized aminoalkylsiloxanes are preferably added to the compound (a); the quaternized aminoalkylsiloxane (silicone quat) is particularly preferably initially introduced, and the emulsion formation is completed by addition of the compound (a) and optionally further additives.
Die erfindungsgemäßen Formulierungen eignen sich hervorragend als Textilweichmacher bei der Ausrüstung von textilen Flächengebilden, insbesondere solchen aus Baumwolle, Keratinfasern, bevorzugt Wolle, Seide oder Synthesefasern oder spielsweise sehr gut für die Ausrüstung von textilen Flächengebilden aus Mischungen von Baumwolle mit Polyester, Polyamid, Polyacrylnitril, Wolle oder Seide einsetzen. Exzellente Ergebnisse werden gleichermaßen bei der Ausrüstung textiler Flächengebilde aus Synthesefasern, insbesondere aus Polyester, Polyamid, Polypropylen oder Mischungen daraus erzieltThe formulations according to the invention are outstandingly suitable as fabric softeners in the finishing of textile fabrics, in particular those of cotton, keratin fibers, preferably wool, silk or synthetic fibers or For example, very good for the equipment of textile fabrics made of blends of cotton with polyester, polyamide, polyacrylonitrile, wool or silk. Excellent results are equally obtained in the finishing of textile fabrics of synthetic fibers, in particular of polyester, polyamide, polypropylene or mixtures thereof
Unter textilen Flächengebilden sind bevorzugt Gewebe, Gewirke, Maschenware und Vliese zu verstehen.Textile fabrics are preferably understood to mean woven fabrics, knitted fabrics, knitted fabrics and nonwovens.
Als besonders vorteilhaft hat sich die Verwendung der erfindungsgemäßen Formulierungen für die Ausrüstung von Baumwolle oder baumwollhaltigen Textilien, die mit anionischen Weißtönern vorbehandelt wurden, nach dem Jet-Verfahren erwiesen.The use of the formulations according to the invention for finishing cotton or cotton-containing textiles which have been pretreated with anionic whiteners has proven particularly advantageous according to the jet process.
Beim Einsatz der erfindungsgemäßen Formulierungen können nicht nur hervorragende Weichmacher-Ergebnisse erreicht werden, vielmehr werden auch andere Eigenschaften des Textils, wie die Vernähbarkeit, verbessert oder der Glanz erhöht.When using the formulations according to the invention not only excellent plasticizer results can be achieved, but also other properties of the textile, such as the sewability, improved or increased the gloss.
Die Ausrüsung erfolgt im allgemeinen nach dem Kontinue-Verfahren (Foulard- oder Lisseuse- Verfahren) oder nach dem Ausziehverfahren (Jet-Verfahren). Bei Anwendung der erfindungsgemäßen Formulierungen nach einem dieser Ausrüstungsverfahrenen hat es sich als vorteilhaft erwiesen, die folgenden technologischen Parameter einzuhalten:The equipment is generally carried out by the continuous process (pad-type or lisseuse process) or by the exhaustion process (jet process). When applying the formulations according to the invention by one of these finishing processes, it has proven to be advantageous to comply with the following technological parameters:
In den nachstehenden Formulierungen wurde ein gemäß
1a) In einem 1 Liter Dreihalskolben wurden 24 g Wasser und 4,18 g (0,048 mol tertiäre Aminogruppen) N,N,N',N'-Tetramethyl-1,6-hexandiamin und 3,8 g (0,012 mol primäre Aminogruppen) eines unter dem Handelsnamen Jeffamin® ED 600 erhältlichen Alkylenoxidderivates der Struktur
H2NCH(CH3)CH2[OCH2CH(CH3)]a(OCH2CH2)9[OCH2CH(CH3)]bNH2
mit a+b = 3,6
bei Raumtemperatur vorgelegt. Innerhalb von 5 Minuten wurden 12,0 g (0,03 mol) Dodecansäure in Form einer 50 %igen Lösung in 2-Propanol und 1,8 g (0,03 mol) Essigsäure zugesetzt. Nach Erwärmung des Ansatzes auf 50°C wurden innerhalb von 30 Minuten 194,1 g (0,06 mol Epoxygruppen) eines Epoxysiloxans der durchschnittlichen Zusammensetzung
1a) In a 1 liter three-necked flask, 24 g of water and 4.18 g (0.048 mol tertiary amino groups) of N, N, N ', N'-tetramethyl-1,6-hexanediamine and 3.8 g (0.012 mol primary amino groups) an alkylene oxide derivative available under the trade name Jeffamine ® ED 600 of the structure
H 2 NCH (CH 3 ) CH 2 [OCH 2 CH (CH 3 )] a (OCH 2 CH 2 ) 9 [OCH 2 CH (CH 3 )] b NH 2
with a + b = 3.6
submitted at room temperature. Within 5 minutes, 12.0 g (0.03 mol) of dodecanoic acid in the form of a 50% solution in 2-propanol and 1.8 g (0.03 mol) of acetic acid were added. After heating the batch to 50 ° C., 194.1 g (0.06 mol of epoxy groups) of an epoxysiloxane of average composition were added over 30 minutes
Ausgehend von diesem Silikonmaterial wurden drei Microemulsionskonzentrate folgender Zusammensetzung hergestellt:
Diese drei Microemulsionskonzentrate (etwa 40 %ig bezüglich SQ) werden mit Wasser einheitlich auf jeweils 11 % Silikonquatgehalt verdünnt. Von diesen 11 %igen transparenten Microemulsionen werden jeweils 6 g (absolute Silikonquatmenge 0.66 g) abgenommen, mit 6000 ml Wasser und ggf. Zusätzen intensiv vermischt und unter folgenden Randbedingungen zur Jetausrüstung benutzt:
- Jettyp: Mathis Labor-Jumbo-Jet
- Jetpumpe: Stufe 6 (höchstmögliche Scherung)
- Wassermenge im Jet: 6000 ml
- Ausrüstung: 15 Minuten bei 40°C
- Trocknung: 80°C
- Textil: 300g gebleichtes und mit optischem Aufheller (z.B. Blankophor® BA behandeltes Baumwolljersey).
- Jettyp: Mathis lab jumbo jet
- Jet pump: level 6 (highest possible shear)
- Amount of water in the jet: 6000 ml
- Equipment: 15 minutes at 40 ° C
- Drying: 80 ° C
- Textile: 300g bleached and with optical brightener (eg Blankophor® BA treated cotton jersey).
In der nachfolgenden Tabelle sind die Ergebnisse der Ausrüstversuche zusammengefasst.
0.06g Renex ®30
** silikonartig weich mit Volumengewinn
*** Tropfeneinsinkzeit ≤ 3 Sekunden
Renex® 36 Handelsname der ICI Surfactants; Tridecylalkohol-(EO)12-OH
Renex® 30 Handelsname der ICI Surfactants; Tridecylalkohol-(EO)6-OH
Crodet® S40 Handelsname der Croda GmbH; Stearinsäure-(EO)40-OH
0.06g Renex®30
** soft silicone with volume gain
*** Drop in time ≤ 3 seconds
Renex® 36 trade name of ICI Surfactants; Tridecyl alcohol (EO) 12 -OH
Renex® 30 trade name of ICI Surfactants; Tridecyl alcohol (EO) 6 -OH
Crodet® S40 trade name of Croda GmbH; Stearic acid (EO) 40 -OH
Versuch 1 beschreibt das inakzeptable Ergebnis eines nicht erfindungsgemäßen Versuchs gemäß dem Stand der Technik. Eine Verdoppelung der Tensidmenge beider Renex-Typen führt nicht zu einer Verhinderung der Ausfällung (Versuch 2, nicht erfindungsgemäß).Experiment 1 describes the unacceptable result of a non-inventive experiment according to the prior art. A doubling of the amount of surfactant of both Renex types does not lead to a prevention of precipitation (Experiment 2, not according to the invention).
Versuch 3 zeigt, dass durch einen erfindungsgemäßen Einbau von hydrophilen grenzflächenaktiven Verbindungen direkt in die Formulierung eine Ausfällung zuverlässig verhindert wird. Dies trifft auch auf eine ebenfalls erfindungsgemäße partielle nachträgliche Hinzufügung (Versuch 4) oder erfindungsgemäße vollständige Hinzufügung (Versuch 5) dieser hydrophilen grenzflächenaktiven Verbindung zu.Experiment 3 shows that by incorporating hydrophilic surface-active compounds directly into the formulation according to the invention precipitation is reliably prevented. This also applies to a partial subsequent addition according to the invention (Experiment 4) or complete addition according to the invention (Experiment 5) to this hydrophilic surface-active compound.
Claims (15)
- A formulation comprising at least one quaternized aminoalkylsiloxane and at least one compound from the group ofa) hydrophilic, nonionogenic interface-active compounds, characterized in that the hydrophilic, nonionogenic interface-active compounds (a) are compounds modified with ethylene/propylene oxide (EO/PO), optionally unsaturated and/or branched, from the group of the fatty alcohols, fatty acids, alcohols, acids, alkylaryl derivatives, fatty amines, glycerides and sorbitan esters, wherein the number of EO/PO units is between 15 and 150, wherein the ratio of PO units to EO units is equal to or lower than 0.25, and in which the number of ethylene oxide units (EO fraction) is greater than or equal to the number of carbon atoms in the non-EO fraction, and are alkylpolyglycosides, ethylene oxide/propylene oxide copolymers and polyethersiloxanes, and further characterized in that the quaternized aminoalkylsiloxane is a straight-chain or cyclic polysiloxanepolymer having repeating structural units of the formulae (10) and (11)
X is a divalent hydrocarbon radical having at least 4 carbon atoms which may have a hydroxyl group, preferably has a hydroxyl group, and which may be interrupted by an oxygen atom, and the X groups in the repeating units may be the same or different,Y is a divalent hydrocarbon radical having at least 2 carbon atoms which may have a hydroxyl group and which may be interrupted by one or more oxygen or nitrogen atoms,R11, R12, R13 and R14 are the same or different and are alkyl radicals having from 1 to 4 carbon atoms or benzyl radicals, or the R1 and R3 or R2 and R4 radicals may in each case be constituents of a bridging alkylene radical,R16 is H or an alkyl radical having from 1 to 20 carbon atoms which may be oxygen-substituted,M is the structure -B-O-(EOx)v(POx)w-B-, wherein EOx is an ethylene oxide unit and POx is a propylene oxide unit,B is straight-chain or branched C2-C6-alkylene,v is from 0 to 200,w is from 0 to 200,v+w ≥ 1,n is from 2 to 1000, wherein the n in the repeating units may be the same or different,A is an inorganic or organic anion. - The formulation according to claim 1, characterized in that compound (a) is a compound of the formulae (1) to (9)
R1-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E (1),
R2-NH-[CH2CH(CH3)O]r-[CH2CH2O]q-E (3),
R2-NH-CH(CH3)CH2-[OCH2CH(CH3)]mr-[OCH2CH2]q-[OCH2CH(CH3)]ma-NH-R2 (7).
E-O-[CH2CH2O]s-[CH2CH(CH3)O]r-E (8),
or
E is a radical R1, hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C1-C18-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, or is C5-C10-cycloakyl which is optionally mono- or polysubstituted by C1-C4- alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R1 is straight-chain or branched, saturated or unsaturated C8-C40-alkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di-C1- C4-alkylamino, or is C5-C10-cycloalkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and which is optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di- C1-C4-alkyl-amino,R2 is straight-chain or branched, saturated or mono- to polyunsaturated C8- C40-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4- alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R3 is straight-chain or branched C1-C26-alkyl or C6-C10-aryl,R4 is R3 or a radical of the formulae
-CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E,
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
-CH2CH2CH2-O-CH2CHOHCH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
-Z-[CH2CH2O]q-[CH2CH(CH3)O]r-E
whereinZ is a straight-chain or branched alkyl or cycloalkyl radical which is in each case interrupted by -0- and/or -CO- and may optionally be substituted by at least one OH group,
or
q is from 15 to 150,
q1 and q2 are each independently from 0 to 150, where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 0 to 150, where the sum of q3+q4+q5+q6=q,r is from 0 to 50,
r1 and r2 are each independently from 0 to 50, where the sum of r1 +r2=r,
r3, r4, r5 and r6 are each independently from 0 to 50,
where the sum of r3+r4+r5+r6=r, and
the ratio of r:q≤0.25,m is from 1 to 50,
m7 and m8 are each independently from 1 to 50, where 2≤m7+m8 and the sum of m7+m8=m+1, and
the ratio of q:m≥4,
s is from 5 to 150,
t is from 5 to 150,
where 0.05≤s:t≤20,
0≤z1 ≤2000,
0≤z2≤2000,
at least one R4≠R3, and
- The formulation according to claim 2, whereinE is hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C1-C4-alkyl which is optionally mono- to disubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, or is C5-C6-cycloalkyl which is in each case optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R1 is straight-chain or branched, saturated or unsaturated C10-C36-alkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di-C1-C4-alkylamino, or is C5-C6-cycloalkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di-C1-C4-alkylamino,R2 is straight-chain or branched, saturated or mono- to polyunsaturated C10- C36-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4- alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R3 is straight-chain or branched C1-C18-alkyl or C6-C10-aryl,R4 is a R3 radical or is a radical of the formulae
-CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E,
or
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
q is from 20 to 100,
q1 and q2 are each independently from 20 to 100 where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 20 to 100, where the sum of q3+q4+q5+q6=q,r is from 0 to 20,
r1 and r2 are each independently from 0 to 20, where the sum of r1 +r2=r, r,
r3, r4, r5 and r6 are each independently from 0 to 20, where the sum of r3+r4+r5+r6=r, and
the ratio of r:q≤0.25,m is from 1 to 7,
m7 and m8 are each independently from 1 to 7, where 2≤m7+m8 and the sum of m7+m8=m, and
the ratio of q:m≥4,s is from 5 to 100,t is from 5 to 100,where 0,05≤s:t≤20,
0≤z1≤2000,
0≤z2≤2000,
at least one R4≠R3, and
- The formulation according to at least one of claims 1 to 3, characterized in that compound (a) is a compound of the formulae (1') to (9')
the terms in the brackets "{" and "}" shown in formulae (1')-(8') mean that the ethylene oxide or propylene oxide units may either be arranged blockwise as shown or else be in any random distribution,E is a radical R1, hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C1-C18-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, or is C1-C10-cycloalkyl which is optionally mono- or polysubstituted by C1-C4- alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R1 is straight-chain or branched, saturated or unsaturated C8-C40-alkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di- C1- C4-alkylamino, or is C5-C10-cycloalkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di- C1-C4-alkylamino, or is C6-C10-aryl which is optionally substituted, especially by C3-C15-alkyl,R2 is straight-chain or branched, saturated or mono- to polyunsaturated C8- C40-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4- alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R3 is straight-chain or branched C1-C26-acyl or C6-C10-aryl,R4 is R3 or is a radical of the formulae
Z is a straight-chain or branched alkyl or cycloalkyl radical which is in each case interrupted by -0- and /or -CO- and may optionally be substituted by at least one OH group
or
q is from 15 to 150,
q1 and q2 are each independently from 0 to 150, where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 0 to 150, where the sum of q3+q4+q5+q6=q,r is from 0 to 50,
r1 and r2 are each independently from 0 to 50, where the sum of r1 +r2=r, r,
r3, r4, r5 and r6 are each independently from 0 to 50, where the sum of r3+r4+r5+r6=r, and
the ratio of r:q≤0.25,m is from 1 to 50,
m7 and m8 are each independently from 1 to 50, where 2≤m7+m8, and
the ratio of q:m≥4,s is from 5 to 150, preferably 15-150,t is from 5 to 150, preferably from 5 to 150 and in particular from 5 to 20, wheret:s≤0.25
0≤z1≤2000,
0≤z2≤2000,
at least one R4≠R3, and
for formula (9'):
- The formulation according to claim 4, whereinE is hydrogen, straight-chain or branched, saturated or mono- or polyunsaturated C1-C4-alkyl which is optionally mono- to disubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, or is C5-C6-cycloalkyl which is in each case optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R1 is straight-chain or branched, saturated or unsaturated C10-C36-alkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di-C1-C4-alkylamino, or is C5-C6-cycloalkyl whose alkyl chain is optionally interrupted singly or multiply by oxygen and/or nitrogen atoms and which is optionally mono- or polysubstituted by C1-C4-alkyl, -OH, C1-C4-alkoxy, C1-C4-alkoxycarbonyl or carbonyl, amino, mono- or di-C1-C4-alkylamino, or is C6-C10-aryl which is optionally substituted, especially by C3-C15-alkyl,R2 is straight-chain or branched, saturated or mono- to polyunsaturated C10- C36-alkyl which is optionally mono- or polysubstituted by -OH, C1-C4- alkoxy, C1-C4-alkoxycarbonyl or carbonyl,R3 is straight-chain or branched C1-C18-alkyl or C6-C10-aryl,R4 is a R3 radical or is a radical of the formulae
q is from 20 to 100,
q1 and q2 are each independently from 20 to 100 where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 20 to 100, where the sum of q3+q4+q5+q6=q,r is from 0 to 20,
r1 and r2 are each independently from 0 to 20, where the sum of r1 +r2=r,
r3, r4, r5 and r6 are each independently from 0 to 20, where the sum of r3+r4+r5+r6=r, and
the ratio of r:q≤0.25,m is from 1 to 7,
m7 and m8 are each independently from 1 to 7, where 2≤m7+m8 and the sum of m7+m8=m, and
the ratio of q:m≥4,s is from 5 to 100, preferably from 15 to 100,t is from 5 to 100, preferably from 5 to 20, where t:s≤0.25,
0≤z1≤2000,
0≤z2≤2000,
at least one R4≠R3, and
for formula (9'):
- The formulation according to at least one of claims 2 to 3, whereinE is H, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2- or CH3C(O)-R1 a radical of the formulae
CH3(CH2)n1-
CH3(CH2)7CH=CH(CH2)8-
wherein
n1=from 9 to 23,
n2=from 3 to 23,
n3=from 0 to 18,
n4=from 7 to 23,
n5=from 3 to 15,R2 is a radical of the formulae
n6=8 to 28,R3 is C1-C18-alkyl or C6-C10-aryl,R4 is a radical R3 or is a radical of the formulae
-CH2CH2CH2-O-[CH2CH2O]q-[CH2CH(CH3)O]r-E
q is from 25 to 60,
q1 and q2 are each independently from 25 to 60, where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 25 to 60, where the sum of q3+q4+q5+q6=q,r is from 0 to 10,r1 and r2 are each independently from 0 to 10, where the sum of r1 +r2=r, r,
r3, r4, r5 and r6 are each independently from 0 to 10, where the sum of r3+r4+r5+r6=r, and
the ratio r:q≤0.25, and
for formula (9):
- The formulation according to at least one of claims 4 and 5, whereinE is H, CH3-, CH3CH2-, CH3CH2CH2-, (CH3)2CH-, CH3CH2CH2CH2- or CH3C(O)-R1 a radical of the formulae
CH3(CH2)n1-
CH3(CH2)7CH=CH(CH2)8-
wherein
n1=from 9 to 23,
n2=from 3 to 23, preferably from 6 to23 n3=from 0 to 18, wherein preferably n2+n3≤31, n4=from 7 to 23,
n5=from 3 to 15,R2 is a radical of the formulae
n6=8 to 28,R3 is C1-C18-alkyl or C6-C10-aryl,R4 is a radical R3 or is a radical of the formulae
q is from 25 to 60,
q1 and q2 are each independently from 25 to 60, where the sum of q1 +q2=q,
q3, q4, q5 and q6 are each independently from 25 to 60, where the sum of q3+q4+q5+q6=q,r is from 0 to 10,r1 and r2 are each independently from 0 to 10, where the sum of r1+r2=r,
r3, r4, r5 and r6 are each independently from 0 to 10, where the sum of r3+r4+r5+r6=r, and
the ratio r:q≤0.25, and
for formula (9'):
- The formulation according to at least one of claims 1 to 7, characterized in that the compound (a) present is the ester of stearic acid and 40 mol of EO.
- The formulation according to at least one of claims 1 to 8, characterized in that the amounts of hydrophilic, nonionogenic, interface-active compounds (a) to the amounts of quaternized aminoalkylsiloxane compounds are in a ratio Ω of Ω=0,05 to 10.
- The formulation according to at least one of claims 1 to 9 as a textile softener in the finishing of textile structures by the continuous or exhaust process.
- The use according to claim 10 for the finishing of textile structures made of cotton, keratin fibers, preferably wool, silk, synthetic fibers or mixtures of the aforementioned types.
- The use according to claim 10 for the finishing of textile structures made of mixtures of cotton with polyester, polyamide, polyacrylonitrile, wool or silk.
- The use according to claim 10 for the finishing of textile structures made of polyester, polyamide, polypropylene or mixtures thereof.
- The use according to at least one of claims 11 to 12, characterized in that textile structures made of cotton or of mixtures of cotton with polyester, polyamide, polyacrylonitrile, wool or silk, said textile structures having been pre-treated with anionic whiteners, are finished in a jet dyeing apparatus.
- A process for preparing the formulations according to at least one of claims 1 to 14, characterized in that at least one quaternized aminoalkylsiloxane, as defined in claim 1, is mixed with at least one hydrophilic, nonionogenic, interface-active compound, as defined in claim 1, and optionally further assistants and/or additives in the temperature range of preferably from 20 to 90° C.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2002121521 DE10221521A1 (en) | 2002-05-14 | 2002-05-14 | Formulations of silicone softeners for textile finishing |
| DE10221521 | 2002-05-14 | ||
| PCT/EP2003/004965 WO2003095735A2 (en) | 2002-05-14 | 2003-05-13 | Softening silicone formulations for textile finishing |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| EP1506336A2 EP1506336A2 (en) | 2005-02-16 |
| EP1506336B1 true EP1506336B1 (en) | 2011-05-04 |
Family
ID=29413825
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| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP20030749889 Expired - Lifetime EP1506336B1 (en) | 2002-05-14 | 2003-05-13 | Softening silicone formulations for textile finishing |
Country Status (10)
| Country | Link |
|---|---|
| US (1) | US7718268B2 (en) |
| EP (1) | EP1506336B1 (en) |
| JP (1) | JP4381299B2 (en) |
| KR (1) | KR101032177B1 (en) |
| CN (1) | CN100368467C (en) |
| AT (1) | ATE508222T1 (en) |
| AU (1) | AU2003232759A1 (en) |
| DE (2) | DE10221521A1 (en) |
| MX (1) | MXPA04011207A (en) |
| WO (1) | WO2003095735A2 (en) |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP4171022B2 (en) | 2002-12-19 | 2008-10-22 | ワッカー ケミー アクチエンゲゼルシャフト | Hydrophilic siloxane copolymers and methods for their production |
| WO2005063855A1 (en) * | 2003-12-23 | 2005-07-14 | Ge Bayer Silicones Gmbh & Co. Kg | Alkoxy- and hydroxyl group-free amino and/or ammonium polysiloxane |
| DE102004027003A1 (en) | 2004-06-03 | 2005-12-22 | Wacker-Chemie Gmbh | Hydrophilic siloxane copolymers and process for their preparation |
| DE102008014761A1 (en) * | 2008-03-18 | 2009-12-10 | Momentive Performance Materials Gmbh | Use of polyamino and / or polyammonium-polysiloxane copolymer compounds |
| CN101633781B (en) * | 2008-07-22 | 2012-11-14 | 道康宁（上海）有限公司 | Emulsion composition, method for softening fiber structure and fiber containing base material |
| EP2700448A1 (en) * | 2012-08-21 | 2014-02-26 | Evonik Industries AG | Branched fatty acids as liquid cation exchangers |
| EP2945993A1 (en) | 2013-01-18 | 2015-11-25 | DWI an der RWTH Aachen e.V. | Treatment of crystalline cellulose-containing substrates |
| CN103601890B (en) * | 2013-11-11 | 2015-09-30 | 齐齐哈尔大学 | A kind of synthetic method of pectination polysiloxane flax soft finishing agent |
| DE102015209627A1 (en) | 2015-05-26 | 2016-12-01 | Rudolf Gmbh | Polyurethane organopolysiloxanes |
| CN105220506B (en) * | 2015-11-03 | 2018-01-19 | 杭州传化精细化工有限公司 | A kind of block polyether eiastomeric silicone softening agent and its preparation method and application |
| KR102423517B1 (en) | 2018-11-20 | 2022-07-20 | 와커 헤미 아게 | Block-modified polysiloxanes and compositions formed therefrom |
| CN110117904A (en) * | 2019-05-23 | 2019-08-13 | 绍兴一扬化工助剂有限公司 | A kind of soft finishing agent and its technique for applying |
| US11732409B2 (en) * | 2020-10-01 | 2023-08-22 | Xerox Corporation | Textiles custom printed with antimicrobial nanoparticles |
| CN118185061B (en) * | 2024-05-16 | 2024-08-02 | 奥斯佳新材料技术研究(江苏)有限公司 | Multifunctional emulsifier for emulsifying organosilicon polymer and application thereof |
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| DE2506466C3 (en) | 1975-02-15 | 1979-07-19 | Hoechst Ag, 6000 Frankfurt | Emulsifier for dye accelerators based on alkyl naphthalenes |
| DE2912485A1 (en) | 1979-03-29 | 1980-10-09 | Henkel Kgaa | NEW QUARTAERE POLYSILOXAN DERIVATIVES, THEIR USE IN HAIR COSMETICS, AND THEIR WASHING AND TREATMENT PRODUCTS CONTAINING THEM |
| DE3705121A1 (en) | 1987-02-18 | 1988-09-01 | Goldschmidt Ag Th | POLYQUATERIAL POLYSILOXANE POLYMERS, THEIR PRODUCTION AND USE IN COSMETIC PREPARATIONS |
| GB8704002D0 (en) * | 1987-02-20 | 1987-03-25 | Unilever Plc | Conditioning fabrics & compositions |
| DE3802622A1 (en) * | 1988-01-29 | 1989-08-10 | Goldschmidt Ag Th | MEANS FOR CUTTING TEXTILE FIBER OR TEXTILE FIBER PRODUCTS |
| JPH02112483A (en) * | 1989-08-04 | 1990-04-25 | Toyobo Co Ltd | Production of antimicrobial fibrous product having improvds susceptibility to discoloration |
| US5173201A (en) * | 1990-07-23 | 1992-12-22 | The Proctor & Gamble Company | Microemulsified amine functional silicone in liquid fabric softeners for reducing fiber-fiber and yarn-yarn friction in fabrics |
| US5098979A (en) * | 1991-03-25 | 1992-03-24 | Siltech Inc. | Novel silicone quaternary compounds |
| US5602224A (en) * | 1996-03-19 | 1997-02-11 | Siltech Inc. | Silicone alkyl quats |
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| US5925701A (en) | 1997-12-22 | 1999-07-20 | Eastman Kodak Company | Stable aqueous polymeric dispersions containing hydrated metal salts of strong acids |
| DE59905052D1 (en) * | 1998-11-14 | 2003-05-22 | Goldschmidt Ag Th | Polyetherquat functional polysiloxanes |
| US6528576B1 (en) | 1999-03-29 | 2003-03-04 | Bayer Aktiengesellschaft | Treatment agents for textiles, method of producing same and their use |
| DE19960107A1 (en) | 1999-12-14 | 2001-06-21 | Bayer Ag | Textile treatment agent, useful for the finishing of natural and synthetic fibers, comprises a polyisocyanate prepolymer having isocyanate groups blocked by bisulfite |
| EP1116813A1 (en) | 2000-01-10 | 2001-07-18 | Dow Corning Corporation | Hydrophilic softener for textiles comprising epoxy glycol siloxane polymers and amine funtional materials |
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| DE10036694A1 (en) * | 2000-07-27 | 2002-02-14 | Wacker Chemie Gmbh | Process for the treatment of organic fibers with amino-functional organosilicon compounds |
| DE50102804D1 (en) | 2000-07-27 | 2004-08-12 | Ge Bayer Silicones Gmbh & Co | POLYAMMONIUM-POLYSILOXANE COMPOUNDS, METHOD FOR THE PRODUCTION THEREOF AND THEIR USE |
| WO2002010256A1 (en) | 2000-07-27 | 2002-02-07 | Ge Bayer Silicones Gmbh & Co. Kg | Mono- or poly-quaternary polysiloxanes |
| DE10036522A1 (en) | 2000-07-27 | 2002-02-21 | Ge Bayer Silicones Gmbh & Co | Novel linear aminoacid modified polyquaternary polysiloxanes are useful in cosmetic formulations for skin and hair care, in polishes and as softeners |
| DE10036532A1 (en) | 2000-07-27 | 2002-02-21 | Ge Bayer Silicones Gmbh & Co | Novel approximatelya,approximatelyc-aminofunctionalized polysiloxanes are useful in cosmetic formulations for skin and hair care, in polishes and as softeners. |
| US7041767B2 (en) | 2000-07-27 | 2006-05-09 | Ge Bayer Silicones Gmbh & Co. Kg | Polysiloxane polymers, method for their production and the use thereof |
| US6903061B2 (en) * | 2000-08-28 | 2005-06-07 | The Procter & Gamble Company | Fabric care and perfume compositions and systems comprising cationic silicones and methods employing same |
| US6649692B2 (en) * | 2001-02-20 | 2003-11-18 | Crompton Corporation | Organopolysiloxane composition, emulsion-forming concentrates and aqueous emulsions formed therefrom and use of the emulsions in the treatment of textiles |
-
2002
- 2002-05-14 DE DE2002121521 patent/DE10221521A1/en not_active Withdrawn
-
2003
- 2003-05-13 AU AU2003232759A patent/AU2003232759A1/en not_active Abandoned
- 2003-05-13 MX MXPA04011207A patent/MXPA04011207A/en not_active Application Discontinuation
- 2003-05-13 CN CNB038150603A patent/CN100368467C/en not_active Expired - Fee Related
- 2003-05-13 AT AT03749889T patent/ATE508222T1/en active
- 2003-05-13 JP JP2004503716A patent/JP4381299B2/en not_active Expired - Fee Related
- 2003-05-13 DE DE50313668T patent/DE50313668D1/en not_active Expired - Lifetime
- 2003-05-13 WO PCT/EP2003/004965 patent/WO2003095735A2/en not_active Ceased
- 2003-05-13 US US10/514,931 patent/US7718268B2/en not_active Expired - Fee Related
- 2003-05-13 KR KR1020047018308A patent/KR101032177B1/en not_active Expired - Fee Related
- 2003-05-13 EP EP20030749889 patent/EP1506336B1/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| DE10221521A1 (en) | 2003-12-04 |
| WO2003095735A2 (en) | 2003-11-20 |
| JP2005533934A (en) | 2005-11-10 |
| DE50313668D1 (en) | 2011-06-16 |
| MXPA04011207A (en) | 2005-02-14 |
| US7718268B2 (en) | 2010-05-18 |
| AU2003232759A1 (en) | 2003-11-11 |
| CN100368467C (en) | 2008-02-13 |
| US20060100396A1 (en) | 2006-05-11 |
| AU2003232759A8 (en) | 2003-11-11 |
| KR20040111607A (en) | 2004-12-31 |
| CN1665981A (en) | 2005-09-07 |
| ATE508222T1 (en) | 2011-05-15 |
| EP1506336A2 (en) | 2005-02-16 |
| WO2003095735A3 (en) | 2004-04-08 |
| JP4381299B2 (en) | 2009-12-09 |
| KR101032177B1 (en) | 2011-05-02 |
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