CA1048039A - Compounds containing aziridine radicals, and their use for reducing shrinkage and felting of goods containing, or consisting of, protein fibers - Google Patents

Compounds containing aziridine radicals, and their use for reducing shrinkage and felting of goods containing, or consisting of, protein fibers

Info

Publication number: CA1048039A
Authority: CA; Canada
Prior art keywords: goods; radicals; aziridine; compound; protein
Prior art date: 1973-07-07
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

Application number

CA204,186A

Other languages

English (en)

French (fr)

Other versions

CA204186S (en

Inventor

Heinz Bille

Felix Miksovsky

Toni Simenc

Rainer Thomas

Rolf Fikentscher

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

BASF SE

Original Assignee

BASF SE

Priority date (The priority date 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 date listed.)

1973-07-07

Filing date

1974-07-05

Publication date

1979-02-06

1973-07-07 Priority claimed from DE19732334655 external-priority patent/DE2334655C3/de

1974-07-05 Application filed by BASF SE filed Critical BASF SE

1979-02-06 Application granted granted Critical

1979-02-06 Publication of CA1048039A publication Critical patent/CA1048039A/en

Status Expired legal-status Critical Current

Links

150000001875 compounds Chemical class 0.000 title claims abstract description 42
108090000623 proteins and genes Proteins 0.000 title claims abstract description 22
102000004169 proteins and genes Human genes 0.000 title claims abstract description 22
239000000835 fiber Substances 0.000 title claims abstract description 15
238000009950 felting Methods 0.000 title claims abstract description 13
238000000034 method Methods 0.000 claims abstract description 21
230000008569 process Effects 0.000 claims abstract description 16
238000006243 chemical reaction Methods 0.000 claims abstract description 14
150000003839 salts Chemical class 0.000 claims description 21
239000000839 emulsion Substances 0.000 claims description 20
210000002268 wool Anatomy 0.000 claims description 13
239000003054 catalyst Substances 0.000 claims description 12
239000001257 hydrogen Substances 0.000 claims description 11
229910052739 hydrogen Inorganic materials 0.000 claims description 11
239000006185 dispersion Substances 0.000 claims description 10
239000004721 Polyphenylene oxide Substances 0.000 claims description 8
229920000570 polyether Polymers 0.000 claims description 8
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 7
LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 claims description 7
238000006359 acetalization reaction Methods 0.000 claims description 5
125000004106 butoxy group Chemical group [*]OC([H])([H])C([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
125000002572 propoxy group Chemical group [*]OC([H])([H])C(C([H])([H])[H])([H])[H] 0.000 claims description 5
125000001301 ethoxy group Chemical group [H]C([H])([H])C([H])([H])O* 0.000 claims description 4
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 3
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 3
238000005470 impregnation Methods 0.000 claims description 3
229920006222 acrylic ester polymer Polymers 0.000 claims description 2
239000012875 nonionic emulsifier Substances 0.000 claims 1
239000000047 product Substances 0.000 description 25
150000002148 esters Chemical class 0.000 description 18
239000002253 acid Substances 0.000 description 15
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
125000000217 alkyl group Chemical group 0.000 description 14
238000005406 washing Methods 0.000 description 9
239000000080 wetting agent Substances 0.000 description 9
NOWKCMXCCJGMRR-UHFFFAOYSA-N Aziridine Chemical compound C1CN1 NOWKCMXCCJGMRR-UHFFFAOYSA-N 0.000 description 8
150000001541 aziridines Chemical class 0.000 description 8
229910052757 nitrogen Inorganic materials 0.000 description 8
239000012190 activator Substances 0.000 description 7
239000000243 solution Substances 0.000 description 7
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
239000003795 chemical substances by application Substances 0.000 description 6
239000000463 material Substances 0.000 description 6
239000000203 mixture Substances 0.000 description 6
229920000642 polymer Polymers 0.000 description 6
IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 5
125000004849 alkoxymethyl group Chemical group 0.000 description 5
125000002947 alkylene group Chemical group 0.000 description 5
-1 aziri-dine compound Chemical class 0.000 description 5
238000004043 dyeing Methods 0.000 description 5
230000000694 effects Effects 0.000 description 5
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
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QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 4
102000011782 Keratins Human genes 0.000 description 4
108010076876 Keratins Proteins 0.000 description 4
239000007864 aqueous solution Substances 0.000 description 4
239000003599 detergent Substances 0.000 description 4
238000001035 drying Methods 0.000 description 4
OKKJLVBELUTLKV-UHFFFAOYSA-N methanol Natural products OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
238000002203 pretreatment Methods 0.000 description 4
238000003756 stirring Methods 0.000 description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 3
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239000002202 Polyethylene glycol Substances 0.000 description 3
DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
125000003545 alkoxy group Chemical group 0.000 description 3
QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
238000007796 conventional method Methods 0.000 description 3
MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
IJGRMHOSHXDMSA-UHFFFAOYSA-N nitrogen Substances N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 3
239000001301 oxygen Substances 0.000 description 3
229910052760 oxygen Inorganic materials 0.000 description 3
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239000011734 sodium Substances 0.000 description 3
239000003760 tallow Substances 0.000 description 3
PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 2
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HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
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SJEYSFABYSGQBG-UHFFFAOYSA-M Patent blue Chemical compound [Na+].C1=CC(N(CC)CC)=CC=C1C(C=1C(=CC(=CC=1)S([O-])(=O)=O)S([O-])(=O)=O)=C1C=CC(=[N+](CC)CC)C=C1 SJEYSFABYSGQBG-UHFFFAOYSA-M 0.000 description 2
GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
239000000980 acid dye Substances 0.000 description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
125000001931 aliphatic group Chemical group 0.000 description 2
VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 2
229920003180 amino resin Polymers 0.000 description 2
CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 2
229910052799 carbon Inorganic materials 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 2
239000007788 liquid Substances 0.000 description 2
229910052749 magnesium Inorganic materials 0.000 description 2
239000011777 magnesium Substances 0.000 description 2
229910052751 metal Inorganic materials 0.000 description 2
239000002184 metal Substances 0.000 description 2
235000011837 pasties Nutrition 0.000 description 2
238000006116 polymerization reaction Methods 0.000 description 2
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150000003077 polyols Chemical class 0.000 description 2
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235000013824 polyphenols Nutrition 0.000 description 2
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102000004196 processed proteins & peptides Human genes 0.000 description 2
239000000985 reactive dye Substances 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 2
241000894007 species Species 0.000 description 2
JFALSRSLKYAFGM-UHFFFAOYSA-N uranium(0) Chemical compound [U] JFALSRSLKYAFGM-UHFFFAOYSA-N 0.000 description 2
238000005303 weighing Methods 0.000 description 2
ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 2
OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
NQPJDJVGBDHCAD-UHFFFAOYSA-N 1,3-diazinan-2-one Chemical compound OC1=NCCCN1 NQPJDJVGBDHCAD-UHFFFAOYSA-N 0.000 description 1
SFFKWPDJEDLBDZ-UHFFFAOYSA-N 1-(dibutoxymethyl)-1-methylurea Chemical compound C(CCC)OC(OCCCC)N(C(=O)N)C SFFKWPDJEDLBDZ-UHFFFAOYSA-N 0.000 description 1
SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
NNTWKXKLHMTGBU-UHFFFAOYSA-N 4,5-dihydroxyimidazolidin-2-one Chemical compound OC1NC(=O)NC1O NNTWKXKLHMTGBU-UHFFFAOYSA-N 0.000 description 1
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 description 1
HGINCPLSRVDWNT-UHFFFAOYSA-N Acrolein Chemical compound C=CC=O HGINCPLSRVDWNT-UHFFFAOYSA-N 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
YSKUZVBSHIWEFK-UHFFFAOYSA-N ammelide Chemical compound NC1=NC(O)=NC(O)=N1 YSKUZVBSHIWEFK-UHFFFAOYSA-N 0.000 description 1
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238000007747 plating Methods 0.000 description 1
229920002239 polyacrylonitrile Polymers 0.000 description 1
229920001281 polyalkylene Polymers 0.000 description 1
229920000139 polyethylene terephthalate Polymers 0.000 description 1
239000005020 polyethylene terephthalate Substances 0.000 description 1
150000008442 polyphenolic compounds Polymers 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
WQGWDDDVZFFDIG-UHFFFAOYSA-N pyrogallol Chemical compound OC1=CC=CC(O)=C1O WQGWDDDVZFFDIG-UHFFFAOYSA-N 0.000 description 1
230000009257 reactivity Effects 0.000 description 1
238000005096 rolling process Methods 0.000 description 1
229920006395 saturated elastomer Polymers 0.000 description 1
230000007017 scission Effects 0.000 description 1
DCKVNWZUADLDEH-UHFFFAOYSA-N sec-butyl acetate Chemical compound CCC(C)OC(C)=O DCKVNWZUADLDEH-UHFFFAOYSA-N 0.000 description 1
235000015424 sodium Nutrition 0.000 description 1
229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
235000010265 sodium sulphite Nutrition 0.000 description 1
239000007787 solid Substances 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000000126 substance Substances 0.000 description 1
239000000758 substrate Substances 0.000 description 1
150000005846 sugar alcohols Polymers 0.000 description 1
229920002994 synthetic fiber Polymers 0.000 description 1
239000012209 synthetic fiber Substances 0.000 description 1
239000011975 tartaric acid Substances 0.000 description 1
235000002906 tartaric acid Nutrition 0.000 description 1
239000004753 textile Substances 0.000 description 1
VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
QQOWHRYOXYEMTL-UHFFFAOYSA-N triazin-4-amine Chemical class N=C1C=CN=NN1 QQOWHRYOXYEMTL-UHFFFAOYSA-N 0.000 description 1
YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 1
GSEJCLTVZPLZKY-UHFFFAOYSA-O triethanolammonium Chemical compound OCC[NH+](CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-O 0.000 description 1
150000004072 triols Chemical class 0.000 description 1
229940116269 uric acid Drugs 0.000 description 1
239000011701 zinc Substances 0.000 description 1
229910052725 zinc Inorganic materials 0.000 description 1
NWONKYPBYAMBJT-UHFFFAOYSA-L zinc sulfate Chemical compound [Zn+2].[O-]S([O-])(=O)=O NWONKYPBYAMBJT-UHFFFAOYSA-L 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D203/00—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom
- C07D203/04—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings
- C07D203/06—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members
- C07D203/08—Heterocyclic compounds containing three-membered rings with one nitrogen atom as the only ring hetero atom not condensed with other rings having no double bonds between ring members or between ring members and non-ring members with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to the ring nitrogen atom
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/26—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds
- C08G65/2603—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen
- C08G65/2606—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring from cyclic ethers and other compounds the other compounds containing oxygen containing hydroxyl groups
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G65/00—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule
- C08G65/02—Macromolecular compounds obtained by reactions forming an ether link in the main chain of the macromolecule from cyclic ethers by opening of the heterocyclic ring
- C08G65/32—Polymers modified by chemical after-treatment
- C08G65/329—Polymers modified by chemical after-treatment with organic compounds
- C08G65/333—Polymers modified by chemical after-treatment with organic compounds containing nitrogen
- C08G65/33396—Polymers modified by chemical after-treatment with organic compounds containing nitrogen having oxygen in addition to nitrogen
- 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
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/48—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen containing the ethylene imine ring

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
General Chemical & Material Sciences (AREA)
Engineering & Computer Science (AREA)
Textile Engineering (AREA)
Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Artificial Filaments (AREA)

CA204,186A 1973-07-07 1974-07-05 Compounds containing aziridine radicals, and their use for reducing shrinkage and felting of goods containing, or consisting of, protein fibers Expired CA1048039A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
DE19732334655 DE2334655C3 (de)		1973-07-07	Aziridinreste enthaltende Verbindung und ihre Verwendung zur Verminderung des Einlaufens und Verfilzens von Proteinfasern enthaltendem oder daraus bestehendem Gut

Publications (1)

Publication Number	Publication Date
CA1048039A true CA1048039A (en)	1979-02-06

Family

ID=5886256

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA204,186A Expired CA1048039A (en)	1973-07-07	1974-07-05	Compounds containing aziridine radicals, and their use for reducing shrinkage and felting of goods containing, or consisting of, protein fibers

Country Status (8)

Country	Link
AT (1)	AT337649B (de)
BE (1)	BE817373A (de)
CA (1)	CA1048039A (de)
CH (2)	CH927274A4 (de)
FR (1)	FR2235962B1 (de)
GB (1)	GB1470243A (de)
IT (1)	IT1016322B (de)
ZA (1)	ZA744339B (de)

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
DE2824469C3 (de)	1978-06-03	1981-04-16	Basf Ag, 6700 Ludwigshafen	Verfahren zur Zubereitung von Aziridinreste enthaltenden Verbindungen

1974
- 1974-07-05 CH CH927274D patent/CH927274A4/xx unknown
- 1974-07-05 CH CH927274A patent/CH574004B5/xx not_active IP Right Cessation
- 1974-07-05 FR FR7423488A patent/FR2235962B1/fr not_active Expired
- 1974-07-05 GB GB2987974A patent/GB1470243A/en not_active Expired
- 1974-07-05 AT AT556974A patent/AT337649B/de not_active IP Right Cessation
- 1974-07-05 CA CA204,186A patent/CA1048039A/en not_active Expired
- 1974-07-05 IT IT51945/74A patent/IT1016322B/it active
- 1974-07-05 ZA ZA00744339A patent/ZA744339B/xx unknown
- 1974-07-08 BE BE146327A patent/BE817373A/xx unknown

Also Published As

Publication number	Publication date
BE817373A (fr)	1975-01-08
GB1470243A (en)	1977-04-14
ATA556974A (de)	1976-11-15
DE2334655B2 (de)	1976-10-14
CH574004B5 (de)	1976-03-31
AT337649B (de)	1977-07-11
FR2235962B1 (de)	1978-11-24
CH927274A4 (de)	1975-09-30
FR2235962A1 (de)	1975-01-31
AU7094974A (en)	1976-01-08
ZA744339B (en)	1975-08-27
DE2334655A1 (de)	1975-02-06
IT1016322B (it)	1977-05-30

Publication	Publication Date	Title
US5438116A (en)	1995-08-01	Polymers and prepolymers and their use in a method for the treatment of wool
US3220869A (en)	1965-11-30	Process for improving textile fabrics
CA1146304A (en)	1983-05-17	Process for the production of formaldehyde-free finishing agents for cellulosic textiles and the use of such agents
US4436524A (en)	1984-03-13	After treating composition for direct or reactive dyeings on cellulose
US3827994A (en)	1974-08-06	Composition for producing wrinkle-free permanently pressed cellulosic textile materials
US3528964A (en)	1970-09-15	Process for the chemical modification of cellulosic polymers and products produced thereby
US4295847A (en)	1981-10-20	Finishing process for textiles
US3983269A (en)	1976-09-28	Durable press composition and process
US3920390A (en)	1975-11-18	Manufacture of finishing agents for cellulosic textiles
US3518043A (en)	1970-06-30	Hexahydropyrimidone derivatives and a method of finishing textile material
US3038776A (en)	1962-06-12	Wrinkle resistant cellulose textiles and processes for producing same
US3984367A (en)	1976-10-05	Durable press composition and process
US4484927A (en)	1984-11-27	Polymers useful for improving the fastness of dyes and optical brighteners on hydroxy group-containing substrates
US4284410A (en)	1981-08-18	Process for the pretreatment of cellulose fibers to be printed according to the thermotransfer printing method
Reid et al.	1958	Durable Creasing of Wrinkle Resistant Cotton1
US2973239A (en)	1961-02-28	Color fixing agents
Franklin et al.	1972	Recurable Durable-Press Fabrics: Part I: Polycarboxylic Acids as Coreactant Curing Catalysts with N-Methylol Reagents
US3523750A (en)	1970-08-11	Process for treatment of proteinaceous materials
US3150000A (en)	1964-09-22	Method and means for treating textiles
US3987231A (en)	1976-10-19	Method of antistatically treating fibrous materials
CA1164163A (en)	1984-03-27	Textile finish and processes for its preparation and use
Lewis et al.	2004	Synthesis of triethanolamine trisulphate and its application to cellulosic fabrics
CA1051614A (en)	1979-04-03	Process for dyeing materials which contain synthetic fibres
Andrews	1992	Safe, Comfortable, Durable Press Cottons: A Natural Progression for a Natural Fiber.
CA1061959A (en)	1979-09-11	Manufacture of easy-care finishing agents for cellulosic textiles