CN106589386A - Quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof - Google Patents
Quaternary ammonium type hydrophilic amino-modified silicone oil emulsion and preparation method thereof Download PDFInfo
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- CN106589386A CN106589386A CN201710008275.3A CN201710008275A CN106589386A CN 106589386 A CN106589386 A CN 106589386A CN 201710008275 A CN201710008275 A CN 201710008275A CN 106589386 A CN106589386 A CN 106589386A
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- silicon oil
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- 238000002360 preparation method Methods 0.000 title claims abstract description 45
- 239000000839 emulsion Substances 0.000 title claims abstract description 44
- 125000001453 quaternary ammonium group Chemical group 0.000 title claims abstract description 30
- 229920002545 silicone oil Polymers 0.000 title claims abstract description 11
- 238000004945 emulsification Methods 0.000 title claims description 11
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 11
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 11
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 11
- QABLOFMHHSOFRJ-UHFFFAOYSA-N methyl 2-chloroacetate Chemical compound COC(=O)CCl QABLOFMHHSOFRJ-UHFFFAOYSA-N 0.000 claims abstract description 8
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims abstract description 8
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 claims abstract description 4
- 239000003054 catalyst Substances 0.000 claims abstract description 4
- 239000007822 coupling agent Substances 0.000 claims abstract description 4
- 239000003921 oil Substances 0.000 claims description 94
- 229910052710 silicon Inorganic materials 0.000 claims description 65
- 239000010703 silicon Substances 0.000 claims description 65
- -1 amido silicon Chemical compound 0.000 claims description 50
- OBFQBDOLCADBTP-UHFFFAOYSA-N aminosilicon Chemical compound [Si]N OBFQBDOLCADBTP-UHFFFAOYSA-N 0.000 claims description 37
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims description 27
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 claims description 24
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 claims description 23
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 11
- 239000002253 acid Substances 0.000 claims description 10
- 239000007864 aqueous solution Substances 0.000 claims description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 8
- 125000003368 amide group Chemical group 0.000 claims description 8
- 239000008367 deionised water Substances 0.000 claims description 8
- 229910021641 deionized water Inorganic materials 0.000 claims description 8
- 239000002904 solvent Substances 0.000 claims description 8
- 229920013822 aminosilicone Polymers 0.000 claims description 7
- QMMBZOSZCYBCDC-UHFFFAOYSA-N NCCNCCC[SiH](OC(OCC)(OCC)OCC)OC Chemical compound NCCNCCC[SiH](OC(OCC)(OCC)OCC)OC QMMBZOSZCYBCDC-UHFFFAOYSA-N 0.000 claims description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims description 6
- UQEAIHBTYFGYIE-UHFFFAOYSA-N hexamethyldisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)C UQEAIHBTYFGYIE-UHFFFAOYSA-N 0.000 claims description 5
- 229940073561 hexamethyldisiloxane Drugs 0.000 claims description 5
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 4
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 4
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 4
- CTLDFURRFMJGON-UHFFFAOYSA-N dimethoxy-methyl-(3-piperazin-1-ylpropyl)silane Chemical compound CO[Si](C)(OC)CCCN1CCNCC1 CTLDFURRFMJGON-UHFFFAOYSA-N 0.000 claims description 3
- 239000007788 liquid Substances 0.000 claims description 3
- 125000001302 tertiary amino group Chemical group 0.000 claims description 3
- IDQBJILTOGBZCR-UHFFFAOYSA-N 1-butoxypropan-1-ol Chemical compound CCCCOC(O)CC IDQBJILTOGBZCR-UHFFFAOYSA-N 0.000 claims description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical class N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 2
- 239000005639 Lauric acid Substances 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 2
- YFCGDEUVHLPRCZ-UHFFFAOYSA-N [dimethyl(trimethylsilyloxy)silyl]oxy-dimethyl-trimethylsilyloxysilane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C YFCGDEUVHLPRCZ-UHFFFAOYSA-N 0.000 claims description 2
- 210000000481 breast Anatomy 0.000 claims description 2
- 229910052757 nitrogen Inorganic materials 0.000 claims description 2
- VIKNJXKGJWUCNN-XGXHKTLJSA-N norethisterone Chemical compound O=C1CC[C@@H]2[C@H]3CC[C@](C)([C@](CC4)(O)C#C)[C@@H]4[C@@H]3CCC2=C1 VIKNJXKGJWUCNN-XGXHKTLJSA-N 0.000 claims description 2
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 claims description 2
- 238000010792 warming Methods 0.000 claims description 2
- POAOYUHQDCAZBD-UHFFFAOYSA-N 2-butoxyethanol Chemical compound CCCCOCCO POAOYUHQDCAZBD-UHFFFAOYSA-N 0.000 claims 1
- CXQXSVUQTKDNFP-UHFFFAOYSA-N octamethyltrisiloxane Chemical compound C[Si](C)(C)O[Si](C)(C)O[Si](C)(C)C CXQXSVUQTKDNFP-UHFFFAOYSA-N 0.000 claims 1
- 239000004744 fabric Substances 0.000 abstract description 20
- 230000004075 alteration Effects 0.000 abstract 1
- 235000013870 dimethyl polysiloxane Nutrition 0.000 abstract 1
- 238000005956 quaternization reaction Methods 0.000 abstract 1
- 238000007789 sealing Methods 0.000 abstract 1
- 238000004383 yellowing Methods 0.000 abstract 1
- 239000002585 base Substances 0.000 description 13
- 229920000570 polyether Polymers 0.000 description 11
- 239000004721 Polyphenylene oxide Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 8
- 238000006243 chemical reaction Methods 0.000 description 8
- 235000011121 sodium hydroxide Nutrition 0.000 description 8
- 239000004902 Softening Agent Substances 0.000 description 7
- UUYQSLQNSVVXCC-UHFFFAOYSA-N CN.C(C=C)(=O)OCCN(C)C Chemical compound CN.C(C=C)(=O)OCCN(C)C UUYQSLQNSVVXCC-UHFFFAOYSA-N 0.000 description 6
- 125000004494 ethyl ester group Chemical group 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- 230000000052 comparative effect Effects 0.000 description 5
- 230000000694 effects Effects 0.000 description 5
- 238000000034 method Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 150000001335 aliphatic alkanes Chemical class 0.000 description 4
- 239000000377 silicon dioxide Substances 0.000 description 4
- FDRCDNZGSXJAFP-UHFFFAOYSA-M sodium chloroacetate Chemical compound [Na+].[O-]C(=O)CCl FDRCDNZGSXJAFP-UHFFFAOYSA-M 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 230000001804 emulsifying effect Effects 0.000 description 3
- 229920001296 polysiloxane Polymers 0.000 description 3
- 125000000022 2-aminoethyl group Chemical group [H]C([*])([H])C([H])([H])N([H])[H] 0.000 description 2
- LRWZZZWJMFNZIK-UHFFFAOYSA-N 2-chloro-3-methyloxirane Chemical compound CC1OC1Cl LRWZZZWJMFNZIK-UHFFFAOYSA-N 0.000 description 2
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 2
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 2
- 238000004140 cleaning Methods 0.000 description 2
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 238000005516 engineering process Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 2
- 150000004702 methyl esters Chemical class 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 238000006116 polymerization reaction Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000004753 textile Substances 0.000 description 2
- XFRVVPUIAFSTFO-UHFFFAOYSA-N 1-Tridecanol Chemical compound CCCCCCCCCCCCCO XFRVVPUIAFSTFO-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- 241000322338 Loeseliastrum Species 0.000 description 1
- VAYOSLLFUXYJDT-RDTXWAMCSA-N Lysergic acid diethylamide Chemical compound C1=CC(C=2[C@H](N(C)C[C@@H](C=2)C(=O)N(CC)CC)C2)=C3C2=CNC3=C1 VAYOSLLFUXYJDT-RDTXWAMCSA-N 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 230000018044 dehydration Effects 0.000 description 1
- 238000006297 dehydration reaction Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical compound C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 description 1
- YQGOWXYZDLJBFL-UHFFFAOYSA-N dimethoxysilane Chemical compound CO[SiH2]OC YQGOWXYZDLJBFL-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000007667 floating Methods 0.000 description 1
- 238000002386 leaching Methods 0.000 description 1
- 229920002521 macromolecule Polymers 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- YWFWDNVOPHGWMX-UHFFFAOYSA-N n,n-dimethyldodecan-1-amine Chemical compound CCCCCCCCCCCCN(C)C YWFWDNVOPHGWMX-UHFFFAOYSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000000643 oven drying Methods 0.000 description 1
- 229910021420 polycrystalline silicon Inorganic materials 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 229920002635 polyurethane Polymers 0.000 description 1
- 239000004814 polyurethane Substances 0.000 description 1
- 230000008569 process Effects 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
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000009467 reduction Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
- 239000002689 soil Substances 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
Classifications
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/385—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing halogens
-
- 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
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
- C08G77/382—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon
- C08G77/388—Polysiloxanes modified by chemical after-treatment containing atoms other than carbon, hydrogen, oxygen or silicon containing nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen and oxygen
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2383/00—Characterised by the use of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen, or carbon only; Derivatives of such polymers
- C08J2383/04—Polysiloxanes
- C08J2383/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/54—Aqueous solutions or dispersions
-
- 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
- D06M2200/00—Functionality of the treatment composition and/or properties imparted to the textile material
- D06M2200/50—Modified hand or grip properties; Softening compositions
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Abstract
The invention discloses a preparation method of a quaternary ammonium type hydrophilic amino-modified silicone oil emulsion. The preparation method includes the following preparation steps that firstly, amino-modified silicone oil is prepared from alpha,omega-hydroxy polydimethyl siloxane (linear organosilicon), an amino coupling agent, a sealing agent and a basic catalyst, then the amino-modified silicone oil and dimethylaminoethyl methacrylate react, acrylate-modified amino-modified silicone oil is obtained, and finally quaternization is carried out through methyl chloroacetate. The quaternary ammonium type hydrophilic amino-modified silicone oil emulsion is simple in preparation process, has self-emulsifying performance, and is used for after-finishing of fabrics, and the fabrics are made to have excellent soft and slip hand feeling, and are low in yellowing, small in color alteration and good in hydrophilicity.
Description
Technical field
The present invention relates to a kind of quaternary ammonium type hydrophile amino silicon oil emulsion and preparation method thereof.
Background technology
Silicone softening agent has good flexibility, slipping, is widely used in the Final finishing of various textiles.Molecule end
End be connected with or main chain in block have the polysiloxanes of Polyethylene oxide, polyoxypropylene or polyoxyethylene poly-oxygen propylene aether group（Letter
Claim polyether silicones）, for the Final finishing of fabric, the good flexibility of fabric, preferable hygroscopicity, antistatic behaviour can be provided with
And soil release performance energy, thus will have a good application prospect in terms of chemical ＆ blended fabric, the natural emulation arrangement of blend fabric.
Organic silicon modified by polyether softening agent by Michael's addition, contracts with allyl-terminated polyether and containing hydrogen silicone oil as raw material
The chemical reactions such as poly-, copolymerization are grafted polyethers chain link or block is on organosilicon macromolecule chain link, in additional emulsifying agent or
Self emulsifying prepares organic silicon emulsion.Its preparation method mainly has following two：
First, polyether-containing aminopolysiloxane is reacted using hydrophilic epoxidized polyether with amido silicon oil.Polyethers parent prepared by the method
Water modified amino silicon oil finishing agent reaction temperature is high, and the time is long, and consumption of organic solvent is big, is additionally, since polyethers chain link to poly- silicon
The partly shielding effect effect of oxygen alkane chain link so that the hydrophilic of softening agent and soft skating sense are difficult to get both.
Second, the modified ternary polymerization softening agent of block polyether, i.e., using containing hydrogen silicone oil, pi-allyl active polyether or allyl
Base glycidyl ether, polyetheramine etc. prepare hydrophilic softening agent.The hydrophilic softening agent response time prepared by the method is long, solvent
Consumption is big, and high cost, production technology easily fluctuates.
It is soft that Chinese patent CN103487307A prepares a kind of quaternary ammonium cation polyurethane-base polyether block organosilicon
Soft dose, due to the introducing of polyurethane chain link, the flexibility of many feels has affected.Simultaneously Chinese patent CN101914206A is utilized
Epoxychloropropane and the reaction of dimethyl lauryl amine solution obtain a kind of quaternized modified amino silicone oil softener, due to dodecyl
The introducing of long-chain so that quaternary ammonium salt hydrophilic group hydrophobization, affects hydrophilicity, while the introducing of dodecyl long-chain also affects
Feel.Chinese patent CN105837823A obtains one kind certainly using dimethylaminoethyl methacrylate and epichlorohydrin reaction
The quaternary ammonium type organic silicon emulsion of emulsifying.But the introducing of epoxychloropropane can cause cross-linking reaction (《Daily chemical industry》2016
The 3rd phase of volume 31,27-30 page), so as to affect the soft feel and product stability of final products.United States Patent (USP)
In US20090274643A1, tertiary amino ternary polymerization silicone oil is obtained using epoxy silicon oil and diethyl amino propylamine reaction, then
Recycle methyl chloroacetate to carry out quaterisation, obtain a kind of extraordinary softening agent of hydrophilic, with fabulous alkali resistance,
But soft skating sense is poor.
The content of the invention
Present invention aim at using the quaternized acrylate modified amido silicon oil of methyl chloroacetate, there is provided a kind of quaternary ammonium type
Hydrophile amino silicon oil emulsion preparation method, preparation process is simple, with automatic emulsifying performance, the Final finishing for textile has pole
Good soft skating sense, xanthochromia is low, and complexion changed is little, good hydrophilic property.
The technical scheme is that：
A kind of quaternary ammonium type hydrophile amino silicon oil emulsion, it is characterised in that：Structural formula is as follows：
Or
Wherein, m=0～100；
N=0～50.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, comprises the following steps：
A. the preparation of amido silicon oil：Prepare mixture by following mass percent first：
α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）70 ~ 96%,
Amino coupling agent 0.1 ~ 5%,
Closure agent 0.1 ~ 10%,
Base catalyst 0.01 ~ 0.6%,
Then, in nitrogen N2Protection under mixture is warming up to into 70～100 DEG C, vacuum be reaction 2 under 70～300mbar～
5 hours, prepare amido silicon oil;
B. the preparation of dimethylaminoethyl methacrylate modified amino silicon oil：By the amido silicon oil and methacrylic acid two
Methylamino ethyl ester is placed in solvent, is reacted 10～20 hours in 30～60 DEG C, obtains methacrylate modified amido silicon oil, its
In, the primary amino radical or secondary amino group in the amido silicon oil is 1 with the mol ratio of dimethylaminoethyl methacrylate:1～1:
1.2；
C. the preparation of quaternized amino silicone oil：By the methacrylate modified amido silicon oil and methyl chloroacetate in solvent
In react 8～15 hours in 60～90 DEG C, obtain quaternized amido silicon oil, wherein, methyl chloroacetate and described modified ammonia
The mol ratio of the tertiary amino of base silicone oil is 1:1～1:3；
D. the preparation of quaternary ammonium type hydrophile amino silicon oil emulsion：By the quaternized amido silicon oil, at 15～30 DEG C, with acid
PH to 4～6, substep Deca deionized water are adjusted, rp-emulsification obtains organic silicon emulsion, i.e. quaternary ammonium type hydrophile amino silicon oil breast
Liquid.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, the α, ω-hydroxyl polydimethylsiloxane,
Average viscosity is 10 to 1000 milli pascal seconds at 25 DEG C.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, the amino coupling agent is γ-piperazinopropyl first
One or more in base dimethoxysilane, N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, the closure agent is hexamethyl disiloxane or eight first
Base trisiloxanes or decamethyl tetrasiloxane.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, the base catalyst is 20～50% aqueous solutions
One kind in potassium hydroxide, sodium hydroxide, tetramethyl oxyammonia.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, the solvent is ethanol, isopropanol, ethylene glycol only son
One kind in ether, propandiol butyl ether.
The preparation method of above-mentioned quaternary ammonium type hydrophile amino silicon oil emulsion, described acid is in acetic acid, lauric acid, malonic acid
It is a kind of.
The invention has the beneficial effects as follows：Organic silicon emulsion provided by the present invention, for deep-colour fabric, increases deep effect and shows
Write, for white fabrics, complexion changed is little, and xanthochromia is low, while the finishing agent can give fabric splendid soft, smooth feel, and
And with excellent hydrophilic, preparation method is simple.
Specific embodiment
With reference to specific embodiment, the present invention is further elucidated.It should be understood that these embodiments are merely to illustrate the present invention
And do not limit the present invention.In addition, it is to be understood that after part invention has been read, those skilled in the art can make various changing to the present invention
Dynamic or modification, these equivalent form of values equally fall within the application appended claims limited range.
Embodiment one：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 20 grams
N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, the silica of hexamethyl two
5 grams of alkane, at 95 DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) preparation of modified amino silicon oil：By described 685 grams of amido silicon oils and 15.6 grams of dimethylaminoethyl acrylate methyl
Amino ethyl ester is added to mix homogeneously in 210 grams of aqueous isopropanol, reacts 10 hours at 30 DEG C, obtains dimethylaminoethyl acrylate methyl
The modified amido silicon oil of amino ethyl ester.
(3) quaterisation：By monoxone of the aqueous isopropanol gram of described modified amino silicon oil 910 with 10.8 grams
Methyl ester mix homogeneously, reacts 8 hours in 80 DEG C, obtains quaternized amino silicone oil.
(4) rp-emulsification：11.6 grams of acid is added in 920.8 grams of quaternized amido silicon oil, under stirring condition
In 25 DEG C, the deionized water that 1250 grams of Deca is stirred 1.5 hours, obtains organic silicon emulsion E1.
Embodiment two：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 25 grams
γ-piperazinopropyl methyl dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, 5 grams of hexamethyl disiloxane, 95
DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) preparation of modified amino silicon oil：By described 685 grams of amido silicon oils and 17 grams of dimethylaminoethyl acrylate methyl ammonia
Base ethyl ester is added to mix homogeneously in 210 grams of aqueous isopropanol, reacts 10 hours at 30 DEG C, obtains dimethylaminoethyl acrylate methyl ammonia
The ethyl ester modified amido silicon oil of base.
(3) quaterisation：By the aqueous isopropanol and 23.5 grams of monoxone of 912 grams described of modified amino silicon oil
Methyl ester mix homogeneously, reacts 8 hours in 80 DEG C, obtains quaternized amino silicone oil.
(4) rp-emulsification：13 grams of acid is added in 935.5 grams of quaternized amido silicon oil, under stirring condition in
25 DEG C, the deionized water that 1250 grams of Deca is stirred 1.5 hours, obtains organic silicon emulsion E2.
Embodiment three：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 30 grams
N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, the silica of hexamethyl two
5 grams of alkane, at 95 DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) preparation of modified amino silicon oil：By described 695 grams of amido silicon oils and 23 grams of dimethylaminoethyl acrylate methyl ammonia
Base ethyl ester is added to mix homogeneously in 210 grams of aqueous isopropanol, reacts 10 hours at 30 DEG C, obtains dimethylaminoethyl acrylate methyl ammonia
The ethyl ester modified amido silicon oil of base.
(3) quaterisation：By the aqueous isopropanol and 16 grams of monoxone first of 928 grams described of modified amino silicon oil
Ester mix homogeneously, reacts 8 hours in 80 DEG C, obtains quaternized amino silicone oil.
(4) rp-emulsification：17.5 grams of acid is added in 944 grams of quaternized amido silicon oil, under stirring condition in
25 DEG C, the deionized water that 1250 grams of Deca is stirred 1.5 hours, obtains organic silicon emulsion E3.
Example IV：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 35 grams
γ-piperazinopropyl methyl dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, 5 grams of hexamethyl disiloxane, 95
DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) preparation of modified amino silicon oil：By described 700 grams of amido silicon oils and 24 grams of dimethylaminoethyl acrylate methyl ammonia
Base ethyl ester is added to mix homogeneously in 210 grams of aqueous isopropanol, reacts 10 hours at 30 DEG C, obtains dimethylaminoethyl acrylate methyl ammonia
The ethyl ester modified amido silicon oil of base.
(3) quaterisation：By the aqueous isopropanol and 33 grams of monoxone first of 934 grams described of modified amino silicon oil
Ester mix homogeneously, reacts 8 hours in 80 DEG C, obtains quaternized amino silicone oil.
(4) rp-emulsification：18.1 grams of acid is added in 967 grams of quaternized amido silicon oil, under stirring condition in
25 DEG C, the deionized water that 1250 grams of Deca is stirred 1.5 hours, obtains organic silicon emulsion E4.
Embodiment five：
Embodiment five is essentially identical with embodiment one, except that the amount of hexamethyl disiloxane be 30 grams, other parts with
Embodiment one is identical, obtains organic silicon emulsion E5.
Embodiment six：
Embodiment six is essentially identical with embodiment one, except that the amount of 30% sodium hydrate aqueous solution is 0.6 gram, other
Part is identical with embodiment one, obtains organic silicon emulsion E6.
Embodiment seven：
Embodiment seven is essentially identical with embodiment one, except that reaction temperature is 60 DEG C in the preparation of modified amino silicon oil,
Other parts are identical with embodiment one, obtain organic silicon emulsion E7.
Embodiment eight：
Embodiment eight is essentially identical with embodiment one, except that solvent is ethanol in modified amino silicon oil quaterisation,
Other parts are identical with embodiment one, obtain organic silicon emulsion E8.
Embodiment nine：
Embodiment nine is essentially identical with embodiment one, except that the time of quaterisation be 15 be hour, other parts
It is identical with embodiment one, obtain organic silicon emulsion E9.
Embodiment ten：
Embodiment ten is essentially identical with embodiment two, except that the amount of methyl chloroacetate be 35 grams, other parts with implement
Example two is identical, obtains organic silicon emulsion E10.
Comparative example one：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 20 grams
N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, the silica of hexamethyl two
5 grams of alkane, at 95 DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) rp-emulsification：11.6 grams of acid is added in 685 grams of amido silicon oils and 210 grams of aqueous isopropanols, then is added
Enter the emulsifying agent of 220 grams of isomerous tridecanols, in 25 DEG C under stirring condition, the deionized water that 1513 grams of Deca is stirred 1.5 hours,
Obtain organic silicon emulsion C1.
Comparative example two：
(1) preparation of amido silicon oil：By 660 grams of α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）With 20 grams
N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane, 0.2 gram of 30% sodium hydrate aqueous solution, the silica of hexamethyl two
5 grams of alkane, at 95 DEG C, vacuum is to react 3 hours under 100mbar, in acetic acid and obtains amido silicon oil.
(2) preparation of modified amino silicon oil：By described 685 grams of amido silicon oils and 15.6 grams of dimethylaminoethyl acrylate methyl
Amino ethyl ester is added to mix homogeneously in 210 grams of aqueous isopropanol, reacts 10 hours at 30 DEG C, obtains dimethylaminoethyl acrylate methyl
The modified amido silicon oil of amino ethyl ester.
(3) rp-emulsification：11.6 grams of acid is added in 910.6 grams of quaternized amido silicon oil, 220 are added
The emulsifying agent of gram isomerous tridecanol, in 25 DEG C under stirring condition, the deionized water that 1532 grams of Deca is stirred 1.5 hours, is had
Machine silicon emulsion C2.
Embodiment is contrasted
Quaternary ammonium type hydrophile amino silicon oil emulsion prepared by method described above is configured to into the dressing liquid of 80 g/L, using a leaching one
Prick, dry at 100 DEG C, the process conditions shaped 90 seconds at 170 DEG C, respectively with the product obtained by embodiment and comparative example to treasured
Blue cotton tries to stop people from fighting each other facecloth and the extra white cotton is tried to stop people from fighting each other, and facecloth carries out soft finish.
Evaluation methodology：The feel mainly integrated survey in terms of flexibility and flatness, is touched by several experts are blind, and 5 grades for most
Good, 1 grade is worst.
The hydrophilic of fabric is by with the second（s）One is determined for unit drip the timing definition that water is absorbed completely by fabric.
The durability of fabric：The cleaning mixture of uniform temperature will be in advance heated to（1g/L neutral detergent's aqueous solutions）Addition is washed
In clothing machine, test fabric is added when temperature is down to 40 DEG C, bath raio is 1：50.10 min are washed, cleaning mixture is then released, 40 are used
DEG C clear water washing 5min, dehydration.Operate more than repeating, wash 5 times altogether.Finally by fabric clear water rinsed clean, shakeout, dry
(or oven drying at low temperature).Its washability is differentiated according to the reduction degree of its feel.5 grades is best, and 1 grade is worst.
The increasing depth of fabric：Royalblue cotton is tried to stop people from fighting each other after facecloth arrangement, is surveyed in HunterLab ultrascan VIS (1307)
Examination complexion changed value, value is bigger, increases deep effect better.
The whiteness of fabric：The extra white cotton is tried to stop people from fighting each other after facecloth arrangement, in HunterLab ultrascan VIS (1307) tests
Whiteness value, value is bigger, and whiteness is better.
Stability of emulsion：In baking oven, 50 DEG C store 15 days, without floating oil or layering.
The properties of sample of table 1. compares
| Sample | Feel | Hydrophilic (s) | Durability | Increase deep | Whiteness value | Stability |
| Embodiment E1 | 4.5 | 3 | 3 | 2.8 | 161.2 | It is good |
| Embodiment E2 | 4 | 3.5 | 3 | 2.5 | 165.6 | It is good |
| Embodiment E3 | 5 | 2 | 2 | 2.9 | 161.8 | It is good |
| Embodiment E4 | 4.5 | 2.3 | 2 | 2.7 | 165.2 | It is good |
| Embodiment E5 | 4 | 3.8 | 3 | 2.0 | 159.7 | It is good |
| Embodiment E6 | 4.5 | 3.9 | 3 | 2.5 | 160.8 | It is good |
| Embodiment E7 | 4.5 | 4.2 | 4 | 2.4 | 160.5 | It is good |
| Embodiment E8 | 4 | 4.5 | 4 | 2.1 | 159.1 | It is good |
| Embodiment E9 | 4.5 | 1.8 | 2 | 2.6 | 159.8 | It is good |
| Embodiment E10 | 4 | 1.9 | 2 | 2.2 | 164.9 | It is good |
| Comparative example C1 | 4.5 | 38 | 5 | 2.3 | 158 | It is good |
| Comparative example C2 | 4 | 35 | 4.5 | 2.1 | 159.1 | It is good |
| Blank blue cloth | 1 | 50 | 5 | 0.15 | / | / |
| Blank calico | 1 | 48 | 5 | / | 168.3 | / |
Feel test result can be seen that the quaternary ammonium type hydrophile amino silicon oil emulsion prepared by the present invention from table, for dark color
Fabric, the deep effect of increasing is good, and for white fabrics, complexion changed is little, and xanthochromia is low, while the finishing agent can give fabric splendid soft cunning
Feel, is a kind of high-grade hand feel finishing agent with broad mass market prospect.
Claims (8)
1. a kind of quaternary ammonium type hydrophile amino silicon oil emulsion, it is characterised in that：Structural formula is as follows：
Or
Wherein, m=0～100；
N=0～50.
2. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 1, it is characterised in that including following step
Suddenly：
A. the preparation of amido silicon oil：Prepare mixture by following mass percent first：
α, ω-hydroxyl polydimethylsiloxane（Organosilicon linear body）70 ~ 96%,
Amino coupling agent 0.1 ~ 5%,
Closure agent 0.1 ~ 10%,
Base catalyst 0.01 ~ 0.6%,
Then, in nitrogen N2Protection under mixture is warming up to into 70～100 DEG C, vacuum is that 2～5 are reacted under 70～300mbar
Hour, prepare amido silicon oil;
B. the preparation of dimethylaminoethyl methacrylate modified amino silicon oil：By the amido silicon oil and methacrylic acid two
Methylamino ethyl ester is placed in solvent, is reacted 10～20 hours in 30～60 DEG C, obtains methacrylate modified amido silicon oil, its
In, the primary amino radical or secondary amino group in the amido silicon oil is 1 with the mol ratio of dimethylaminoethyl methacrylate:1～1:
1.2；
C. the preparation of quaternized amino silicone oil：By the methacrylate modified amido silicon oil and methyl chloroacetate in solvent
In react 8～15 hours in 60～90 DEG C, obtain quaternized amido silicon oil, wherein, methyl chloroacetate and described modified ammonia
The mol ratio of the tertiary amino of base silicone oil is 1:1～1:3；
D. the preparation of quaternary ammonium type hydrophile amino silicon oil emulsion：By the quaternized amido silicon oil, at 15～30 DEG C, with acid
PH to 4～6, substep Deca deionized water are adjusted, rp-emulsification obtains organic silicon emulsion, i.e. quaternary ammonium type hydrophile amino silicon oil breast
Liquid.
3. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：The α, ω-
Hydroxyl polydimethylsiloxane, average viscosity is 10 to 1000 milli pascal seconds at 25 DEG C.
4. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：The amino idol
Connection agent is in γ-piperazinopropyl methyl dimethoxysilane, N- (β-aminoethyl)-γ-aminopropyltriethoxy dimethoxysilane
One or more.
5. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：The closure agent
For hexamethyl disiloxane or octamethyltrisiloxane or decamethyl tetrasiloxane.
6. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：The alkalescence is urged
Agent is the one kind in potassium hydroxide, sodium hydroxide, the tetramethyl oxyammonia of 20～50% aqueous solutions.
7. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：The solvent is
One kind in ethanol, isopropanol, ethylene glycol monobutyl ether, propandiol butyl ether.
8. the preparation method of quaternary ammonium type hydrophile amino silicon oil emulsion according to claim 2, it is characterised in that：Described acid is
One kind in acetic acid, lauric acid, malonic acid.
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| CN111410751A (en) * | 2019-01-08 | 2020-07-14 | 上海氟达化学有限公司 | Preparation method of amphoteric organic silicon polymer emulsion |
| US11872301B2 (en) | 2019-08-15 | 2024-01-16 | Kimberly-Clark Worldwide, Inc. | Wetting composition including silicone polymer softening agent and wet wipes including the same |
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| CN111389305B (en) * | 2020-04-26 | 2021-09-07 | 杨凌单色生物科技有限公司 | Amphoteric ion organic silicon surfactant and preparation method thereof |
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