CN117480297A - 用于纺织品的基于聚硅氧烷的防水剂 - Google Patents
用于纺织品的基于聚硅氧烷的防水剂 Download PDFInfo
- Publication number
- CN117480297A CN117480297A CN202280042468.XA CN202280042468A CN117480297A CN 117480297 A CN117480297 A CN 117480297A CN 202280042468 A CN202280042468 A CN 202280042468A CN 117480297 A CN117480297 A CN 117480297A
- Authority
- CN
- China
- Prior art keywords
- emulsion
- weight
- polyorganosiloxane
- amino
- oil phase
- 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.)
- Pending
Links
- -1 Polysiloxane Polymers 0.000 title description 66
- 229920001296 polysiloxane Polymers 0.000 title description 17
- 239000004753 textile Substances 0.000 title description 14
- 238000004078 waterproofing Methods 0.000 title description 2
- 239000000839 emulsion Substances 0.000 claims abstract description 58
- 239000012948 isocyanate Substances 0.000 claims abstract description 25
- 150000002513 isocyanates Chemical class 0.000 claims abstract description 20
- 125000003277 amino group Chemical group 0.000 claims abstract description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 13
- 125000000217 alkyl group Chemical group 0.000 claims description 11
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 7
- 239000004615 ingredient Substances 0.000 claims description 7
- 125000005372 silanol group Chemical group 0.000 claims description 6
- 229910052697 platinum Inorganic materials 0.000 claims description 4
- 239000011368 organic material Substances 0.000 claims description 2
- 239000012260 resinous material Substances 0.000 claims description 2
- 239000000203 mixture Substances 0.000 description 35
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 32
- 239000004744 fabric Substances 0.000 description 15
- 229920000642 polymer Polymers 0.000 description 14
- 229920013822 aminosilicone Polymers 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 239000000463 material Substances 0.000 description 12
- 239000012071 phase Substances 0.000 description 12
- 239000011248 coating agent Substances 0.000 description 11
- 238000000034 method Methods 0.000 description 11
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 11
- 239000004094 surface-active agent Substances 0.000 description 11
- 125000001183 hydrocarbyl group Chemical group 0.000 description 10
- 238000012360 testing method Methods 0.000 description 10
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 9
- 238000002156 mixing Methods 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 235000014113 dietary fatty acids Nutrition 0.000 description 7
- 239000000194 fatty acid Substances 0.000 description 7
- 229930195729 fatty acid Natural products 0.000 description 7
- 239000002736 nonionic surfactant Substances 0.000 description 7
- FVEFRICMTUKAML-UHFFFAOYSA-M sodium tetradecyl sulfate Chemical compound [Na+].CCCCC(CC)CCC(CC(C)C)OS([O-])(=O)=O FVEFRICMTUKAML-UHFFFAOYSA-M 0.000 description 7
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- 229910020175 SiOH Inorganic materials 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000002245 particle Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- 239000000523 sample Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- 239000013523 DOWSIL™ Substances 0.000 description 4
- 229920013731 Dowsil Polymers 0.000 description 4
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 125000005907 alkyl ester group Chemical group 0.000 description 4
- 239000003945 anionic surfactant Substances 0.000 description 4
- 239000003093 cationic surfactant Substances 0.000 description 4
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical class OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 4
- 239000000835 fiber Substances 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 238000006459 hydrosilylation reaction Methods 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- MWRSABPHNREIIX-UHFFFAOYSA-N 9,9-dimethyldecan-1-ol Chemical class CC(C)(C)CCCCCCCCO MWRSABPHNREIIX-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- 229910019142 PO4 Inorganic materials 0.000 description 3
- 229920000538 Poly[(phenyl isocyanate)-co-formaldehyde] Polymers 0.000 description 3
- 238000010521 absorption reaction Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000002280 amphoteric surfactant Substances 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 235000013870 dimethyl polysiloxane Nutrition 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- 150000002170 ethers Chemical class 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000012530 fluid Substances 0.000 description 3
- 235000021317 phosphate Nutrition 0.000 description 3
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 description 3
- 230000008569 process Effects 0.000 description 3
- 229920005989 resin Polymers 0.000 description 3
- 239000011347 resin Substances 0.000 description 3
- SCPYDCQAZCOKTP-UHFFFAOYSA-N silanol Chemical compound [SiH3]O SCPYDCQAZCOKTP-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- CMCBDXRRFKYBDG-UHFFFAOYSA-N 1-dodecoxydodecane Chemical compound CCCCCCCCCCCCOCCCCCCCCCCCC CMCBDXRRFKYBDG-UHFFFAOYSA-N 0.000 description 2
- 125000000094 2-phenylethyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])C([H])([H])* 0.000 description 2
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 description 2
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- XCYBUFDUSFUSPF-UHFFFAOYSA-N N=C=O.C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 Chemical compound N=C=O.C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 XCYBUFDUSFUSPF-UHFFFAOYSA-N 0.000 description 2
- 229920001214 Polysorbate 60 Polymers 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- ULUAUXLGCMPNKK-UHFFFAOYSA-N Sulfobutanedioic acid Chemical class OC(=O)CC(C(O)=O)S(O)(=O)=O ULUAUXLGCMPNKK-UHFFFAOYSA-N 0.000 description 2
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 2
- 150000001242 acetic acid derivatives Chemical class 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000005215 alkyl ethers Chemical class 0.000 description 2
- 239000008346 aqueous phase Substances 0.000 description 2
- 125000003710 aryl alkyl group Chemical group 0.000 description 2
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 2
- 239000002981 blocking agent Substances 0.000 description 2
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000007795 chemical reaction product Substances 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 239000004205 dimethyl polysiloxane Substances 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000002191 fatty alcohols Chemical class 0.000 description 2
- 229920002313 fluoropolymer Polymers 0.000 description 2
- 239000004811 fluoropolymer Substances 0.000 description 2
- 238000005227 gel permeation chromatography Methods 0.000 description 2
- 125000005456 glyceride group Chemical group 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 229910052751 metal Inorganic materials 0.000 description 2
- 239000002184 metal Substances 0.000 description 2
- 125000001624 naphthyl group Chemical group 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- 150000002923 oximes Chemical class 0.000 description 2
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 2
- 150000003013 phosphoric acid derivatives Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 229920000259 polyoxyethylene lauryl ether Polymers 0.000 description 2
- 239000000244 polyoxyethylene sorbitan monooleate Substances 0.000 description 2
- 235000010482 polyoxyethylene sorbitan monooleate Nutrition 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 229920000053 polysorbate 80 Polymers 0.000 description 2
- 150000003141 primary amines Chemical class 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000005871 repellent Substances 0.000 description 2
- 150000003839 salts Chemical class 0.000 description 2
- 150000003333 secondary alcohols Chemical class 0.000 description 2
- 150000003335 secondary amines Chemical group 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000600 sorbitol Substances 0.000 description 2
- 125000001273 sulfonato group Chemical class [O-]S(*)(=O)=O 0.000 description 2
- 125000003944 tolyl group Chemical group 0.000 description 2
- GPRLSGONYQIRFK-MNYXATJNSA-N triton Chemical compound [3H+] GPRLSGONYQIRFK-MNYXATJNSA-N 0.000 description 2
- 125000005023 xylyl group Chemical group 0.000 description 2
- LFSYUSUFCBOHGU-UHFFFAOYSA-N 1-isocyanato-2-[(4-isocyanatophenyl)methyl]benzene Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=CC=C1N=C=O LFSYUSUFCBOHGU-UHFFFAOYSA-N 0.000 description 1
- RFVNOJDQRGSOEL-UHFFFAOYSA-N 2-hydroxyethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCO RFVNOJDQRGSOEL-UHFFFAOYSA-N 0.000 description 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 description 1
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002799 BoPET Polymers 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 235000012766 Cannabis sativa ssp. sativa var. sativa Nutrition 0.000 description 1
- 235000012765 Cannabis sativa ssp. sativa var. spontanea Nutrition 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 241000219146 Gossypium Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 241000208202 Linaceae Species 0.000 description 1
- 235000004431 Linum usitatissimum Nutrition 0.000 description 1
- PRASGDAUCLBKQB-UHFFFAOYSA-N N=C=O.OC1=CC=CC=C1CC1=CC=CC=C1O Chemical class N=C=O.OC1=CC=CC=C1CC1=CC=CC=C1O PRASGDAUCLBKQB-UHFFFAOYSA-N 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920000265 Polyparaphenylene Polymers 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- 229920002396 Polyurea Polymers 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920002334 Spandex Polymers 0.000 description 1
- CZMRCDWAGMRECN-UGDNZRGBSA-N Sucrose Chemical compound O[C@H]1[C@H](O)[C@@H](CO)O[C@@]1(CO)O[C@@H]1[C@H](O)[C@@H](O)[C@H](O)[C@@H](CO)O1 CZMRCDWAGMRECN-UGDNZRGBSA-N 0.000 description 1
- 229930006000 Sucrose Natural products 0.000 description 1
- ISRLGZXSKRDKID-JXBDSQKUSA-N [3-bis[3-[dimethyl-[3-[[(9z,12z)-octadeca-9,12-dienoyl]amino]propyl]azaniumyl]-2-hydroxypropoxy]phosphoryloxy-2-hydroxypropyl]-dimethyl-[3-[[(9z,12z)-octadeca-9,12-dienoyl]amino]propyl]azanium;trichloride Chemical compound [Cl-].[Cl-].[Cl-].CCCCC\C=C/C\C=C/CCCCCCCC(=O)NCCC[N+](C)(C)CC(O)COP(=O)(OCC(O)C[N+](C)(C)CCCNC(=O)CCCCCCC\C=C/C\C=C/CCCCC)OCC(O)C[N+](C)(C)CCCNC(=O)CCCCCCC\C=C/C\C=C/CCCCC ISRLGZXSKRDKID-JXBDSQKUSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 238000002479 acid--base titration Methods 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 229910052783 alkali metal Inorganic materials 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 125000003282 alkyl amino group Chemical group 0.000 description 1
- 150000008055 alkyl aryl sulfonates Chemical class 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000003862 amino acid derivatives Chemical class 0.000 description 1
- 150000003863 ammonium salts Chemical class 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 150000001491 aromatic compounds Chemical class 0.000 description 1
- 150000001504 aryl thiols Chemical class 0.000 description 1
- JPNZKPRONVOMLL-UHFFFAOYSA-N azane;octadecanoic acid Chemical class [NH4+].CCCCCCCCCCCCCCCCCC([O-])=O JPNZKPRONVOMLL-UHFFFAOYSA-N 0.000 description 1
- OGBUMNBNEWYMNJ-UHFFFAOYSA-N batilol Chemical class CCCCCCCCCCCCCCCCCCOCC(O)CO OGBUMNBNEWYMNJ-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 229920001400 block copolymer Polymers 0.000 description 1
- QMNOIORHZMRPLS-UHFFFAOYSA-N butan-1-ol;ethane-1,2-diol;propane-1,2-diol Chemical compound OCCO.CCCCO.CC(O)CO QMNOIORHZMRPLS-UHFFFAOYSA-N 0.000 description 1
- 235000009120 camo Nutrition 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- WOWHHFRSBJGXCM-UHFFFAOYSA-M cetyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCC[N+](C)(C)C WOWHHFRSBJGXCM-UHFFFAOYSA-M 0.000 description 1
- 235000005607 chanvre indien Nutrition 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 239000000084 colloidal system Substances 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 230000001143 conditioned effect Effects 0.000 description 1
- 238000009945 crocheting Methods 0.000 description 1
- 238000007766 curtain coating Methods 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 229940008099 dimethicone Drugs 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- POULHZVOKOAJMA-UHFFFAOYSA-M dodecanoate Chemical compound CCCCCCCCCCCC([O-])=O POULHZVOKOAJMA-UHFFFAOYSA-M 0.000 description 1
- GVGUFUZHNYFZLC-UHFFFAOYSA-N dodecyl benzenesulfonate;sodium Chemical compound [Na].CCCCCCCCCCCCOS(=O)(=O)C1=CC=CC=C1 GVGUFUZHNYFZLC-UHFFFAOYSA-N 0.000 description 1
- 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 1
- 238000005108 dry cleaning Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 238000001914 filtration Methods 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 229930195712 glutamate Natural products 0.000 description 1
- 229940074046 glyceryl laurate Drugs 0.000 description 1
- 150000002332 glycine derivatives Chemical class 0.000 description 1
- 229930182470 glycoside Natural products 0.000 description 1
- 150000002338 glycosides Chemical class 0.000 description 1
- 230000036541 health Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 239000011487 hemp Substances 0.000 description 1
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical class CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 1
- 238000000265 homogenisation Methods 0.000 description 1
- 238000007602 hot air drying Methods 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 150000002483 hydrogen compounds Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 150000002443 hydroxylamines Chemical class 0.000 description 1
- 150000002462 imidazolines Chemical class 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical class OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 238000009940 knitting Methods 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 229940070765 laurate Drugs 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 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 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 150000004714 phosphonium salts Chemical class 0.000 description 1
- 238000004987 plasma desorption mass spectroscopy Methods 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000002574 poison Substances 0.000 description 1
- 231100000614 poison Toxicity 0.000 description 1
- 229920001983 poloxamer Polymers 0.000 description 1
- 229920001987 poloxamine Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- 229920001184 polypeptide Polymers 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 229920005749 polyurethane resin Polymers 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 150000003138 primary alcohols Chemical class 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- ARIWANIATODDMH-UHFFFAOYSA-N rac-1-monolauroylglycerol Chemical compound CCCCCCCCCCCC(=O)OCC(O)CO ARIWANIATODDMH-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 238000001223 reverse osmosis Methods 0.000 description 1
- 229940071089 sarcosinate Drugs 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 238000009958 sewing Methods 0.000 description 1
- FZHAPNGMFPVSLP-UHFFFAOYSA-N silanamine Chemical compound [SiH3]N FZHAPNGMFPVSLP-UHFFFAOYSA-N 0.000 description 1
- 229920002545 silicone oil Polymers 0.000 description 1
- 229920002050 silicone resin Polymers 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229940080264 sodium dodecylbenzenesulfonate Drugs 0.000 description 1
- 239000004289 sodium hydrogen sulphite Substances 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004759 spandex Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 230000007480 spreading Effects 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([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])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 150000003445 sucroses Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 229920000428 triblock copolymer Polymers 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 230000000007 visual effect Effects 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 239000002759 woven fabric Substances 0.000 description 1
- 239000002888 zwitterionic surfactant 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
- 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
- D06M13/395—Isocyanates
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/02—Emulsion paints including aerosols
- C09D5/022—Emulsions, e.g. oil in water
-
- 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
-
- 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
-
- 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
- D06M15/653—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/52—Aqueous emulsion or latex, e.g. containing polymers of a glass transition temperature (Tg) below 20°C
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2205/00—Polymer mixtures characterised by other features
- C08L2205/02—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group
- C08L2205/025—Polymer mixtures characterised by other features containing two or more polymers of the same C08L -group containing two or more polymers of the same hierarchy C08L, and differing only in parameters such as density, comonomer content, molecular weight, structure
-
- 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
- D06M2200/10—Repellency against liquids
- D06M2200/12—Hydrophobic properties
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Textile Engineering (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- Materials Engineering (AREA)
- Health & Medical Sciences (AREA)
- Polymers & Plastics (AREA)
- Medicinal Chemistry (AREA)
- Dispersion Chemistry (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
Abstract
本发明公开了一种包含不连续油相的含水乳液,所述不连续油相包含:a)聚有机氢硅氧烷,b)包含至少一个位于末端位置处的氨基基团的氨基改性的聚有机硅氧烷和c)封端异氰酸酯。
Description
相关申请的交叉引用:本申请根据35U.S.C.§119(e)要求于2021年6月15日提交的美国临时专利申请序列号63/210517的权益。美国临时专利申请序列号63/210517据此以引用方式并入。
技术领域:
本发明涉及可用于处理纺织品的基于聚硅氧烷的组合物。本发明的组合物和相关处理方法可用于处理服装中使用的织物以改善它们的拒水性。
背景技术:
通常对纺织品(诸如用于衣服的织物)进行处理以改善拒水性。虽然含氟聚合物在历史上已被用于此类处理中,但由于对环境和健康的关注,已减少其使用。一种已知的替代方法使用基于聚硅氧烷的涂料组合物。适用的组合物包含一种或多种类型的聚硅氧烷,包括树脂(例如MQ树脂)、聚二有机硅氧烷(例如聚二甲基硅氧烷)、聚有机烯基硅氧烷(例如,包含一个或多个烯基基团的聚有机硅氧烷)和氨基改性的聚有机硅氧烷。例如,US8329255描述了包含烷氧基取代的聚有机硅氧烷(其还可包含氨基官能团)以及封端异氰酸酯交联剂的组合物。US2019/0375897描述了包含有机硅树脂、氨基改性的聚硅氧烷和封端异氰酸酯的组合物。US9777105和US10040891描述了氨基改性或烷氧基聚有机硅氧烷以及封端异氰酸酯和催化剂的用途。
另一类已知的组合物包含聚有机氢硅氧烷,即包含一个或多个-SiH基团的聚有机硅氧烷。例如,US3247281描述了一种组合物,其包含具有至少5重量%的SiH基团的聚有机氢硅氧烷以及催化量的水溶性氨基硅烷。US5409620描述了基于硅氢加成的体系,其包含聚有机氢硅氧烷、不饱和乙酸酯、有机硅(诸如聚有机烯基硅氧烷)和金属催化剂。如本领域已知的,含氨基成分使铂催化剂中毒,因此,氨基改性的聚硅氧烷被排除在这种基于硅氢加成的体系之外。
虽然不针对拒水性,但还已知聚有机硅氧烷用于处理纺织品以改善其它性能,诸如柔软性、润滑性、耐久性、纤维收缩性。例如,US4177176描述了一种用于防止纤维收缩的组合物,其包含氨基改性的、羟基或烷氧基封端的聚有机硅氧烷和聚有机氢硅氧烷。JP2002/146680描述了一种用于改善纤维素纤维布的耐洗涤性和柔软性同时消除与使用硅树脂相关的“粘滑”的组合物。所述组合物包含氨基改性的聚有机硅氧烷和聚有机氢硅氧烷以及氨基甲酸酯预聚物和封端异氰酸酯。所述氨基改性的聚有机硅氧烷包含相对于聚硅氧烷位于侧链位置的氨基基团。
另一类组合物包含聚有机烯基硅氧烷和聚有机氢硅氧烷以及铂催化剂,当将该组合物施加于基底时,其经历硅氢加成反应以形成交联的反应产物。这些基于硅氢加成的体系已被描述用于制备纸和PET膜的防粘和防水涂层(例如参见US2005/0053793)以及用于改善织物和气囊之间的粘附性(例如参见US7534499和WO2019/001901)。
本行业仍在寻求改进的防水组合物和相关的纺织品处理。
发明内容:
本发明的发明人发现与使用基于聚有机氢硅氧烷、氨基硅氧烷和封端异氰酸酯的处理组合物相关的拒水性的出乎意料的改进。更具体地说,本发明人发现,与使用相应的侧链种类相比,在这种组合物中使用末端氨基硅氧烷提供了优异得多的拒水性。本发明包括此类组合物以及它们的制备和在处理纺织品中的用途以及所得的纺织品。本文描述了许多实施方案。
在一个方面,本发明包括一种含水乳液,其包含含水连续相和不连续油相,其中所述不连续油相包含以下成分:a)50重量%至95%重量%的聚有机氢硅氧烷;b)0.1重量%至45重量%的氨基改性的聚有机硅氧烷,其包含至少一个位于末端位置处的氨基基团;以及c)5重量%至30重量%的封端异氰酸酯。在另一个方面,本发明包括前述乳液,其中所述不连续油相包含以下中的至少一者:i)0.5至1.5H重量%和ii)0.004至0.2N重量%。在本发明的又一方面,前述乳液还包含成分d):0.1重量%至10重量%的包含至少一个硅烷醇基团的聚有机硅氧烷。
附图说明
图1是一个洗涤循环后邦迪斯门(Bundesmann)吸水率随表2a中提供的实施例涂料乳液1-6中使用的末端氨基硅氧烷的胺浓度(N重量%)变化的曲线图。
具体实施方式:
如本文所用,术语“纺织品”是指由天然或合成纤维的网络构成的柔性材料。代表性纤维包括棉、亚麻、大麻、丝绸、羊毛、人造丝、纤维素、亚麻布、尼龙、聚丙烯、聚醚-聚脲共聚物(例如“氨纶”)和聚酯。“纺织品”具体地包括通过织造、针织、铺展、毡合、缝合、钩编或粘结此类纤维制成的非织造和织造织物。在本发明的所选实施方案中,感兴趣的织物是用于制造衣物(例如服装)的织物,其中期望在重复清洁(洗涤、干洗等)之后的柔软性、抗水性和耐久性。
本发明组合物优选以包含连续水相的乳液形式提供。用于制备乳液的水可以来自任何来源,并且可任选地例如通过过滤、蒸馏、反渗透技术等进行纯化。如将更充分地描述,该乳液还包含表面活性剂。表面活性剂(或者称为“乳化剂”)用于乳化含水连续相内的不连续聚硅氧烷(油)相。乳液的不连续油相优选占乳液(即包含水、表面活性剂以及任何其它添加剂、溶剂等)总重量的1重量%至10重量%,并且更优选2重量%至5重量%。如下所述,本发明的乳液可在使用前通过将先前制备的不同聚硅氧烷组合物的乳液混合来制备。
乳液的不连续油相包含:a)聚有机氢硅氧烷(“SiH聚合物”),b)包含至少一个位于聚有机硅氧烷的末端位置处的“氨基”基团的氨基改性的聚有机硅氧烷(“末端氨基硅氧烷”)和c)封端异氰酸酯。该非连续油相可任选地包含:d)包含至少一个硅烷醇基团(-SiOH)的聚有机硅氧烷。在一类选定的实施方案中,本发明的乳液包含以下重量百分比的每种前述成分(其中成分a+b+c+d=100%):
a)50重量%至95重量%,优选地60重量%至95重量%,并且更优选地60重量%至90重量%的聚有机氢硅氧烷;
b)0.1重量%至45重量%,优选地1重量%至20重量%的末端氨基硅氧烷;
c)5重量%至30重量%,优选地10重量%至25重量%的封端异氰酸酯;和任选的
d)0.1重量%至10重量%,优选地0.5重量%至5重量%的包含至少一个硅烷醇基团的聚有机硅氧烷。在实施方案的亚类中,本发明的乳液还包含至少一种且优选两种下述物质:
i)通过FTIR测定的0.5至1.5H重量%(作为-SiH)和
ii)通过酸-碱滴定测定的0.004至0.2N重量%,并且更优选地0.005至0.15(作为“氨基”)。
a)聚有机氢硅氧烷(“SiH聚合物”)
指定为成分a)的适用的聚有机氢硅氧烷的种类不受特别限制,并且包括宽范围的常规和可商购获得的材料。这种材料包括环状、直链和支链聚有机氢硅氧烷,优选直链聚合物。适用的聚合物优选地具有500AMU至6000AMU(道尔顿),并且更优选地1000AMU至4500AMU(道尔顿)的重均分子量(Mw)。适用的聚合物可具有根据ASTM D2196-05在25℃下测量的5cSt至50cSt,更优选地10cSt至35cSt的粘度。可以组合使用不同的聚有机氢硅氧烷,例如具有不同化学结构、分子量和/或粘度的那些。本发明的聚有机氢硅氧烷包含至少一个,优选地至少两个,并且更优选地至少三个-SiH基团,其可位于聚硅氧烷主链的末端(端部)和/或中间(侧链)位置上。在优选的实施方案中,-SiH基团主要位于侧链位置处,即如通过29SiNMR测定,大于90重量%,并且更优选地大于95重量%,并且还更优选地大于99重量%的所有-SiH基团位于沿着聚硅氧烷链的侧链位置处。代表性聚有机氢硅氧烷包括具有以下通式的那些:
R3SiO(RRSiO)m(RHSiO)nSiR3
其中m+n=10至100,优选10至60,n优选地为至少3,m优选地为至少7,n/(n+m)优选地大于0.375,并且“R”可以相同或不同并且选自具有1至18个碳原子并且更优选地1至8个碳原子的取代或未取代的一价烃基基团。代表性烃基团包括:a)烷基基团,诸如:甲基、乙基、丙基、丁基、戊基、己基、环己基和庚基;b)芳基基团,诸如苯基、甲苯基、二甲苯基和萘基;以及c)芳烷基基团,诸如苄基和苯乙基;然而,优选甲基和苯基基团,最优选甲基。适用的可商购获得的聚有机氢硅氧烷包括:XIAMETERTMMEM-0075、DOWSILTMMH 1107FLUID、XIAMETERTMOFX-5084、SYL-OFFTM7672和SYL-OFFTM7678,均购自陶氏化学公司(The DowChemical Company)。
b)氨基改性的聚有机硅氧烷(“末端氨基硅氧烷”)
指定为成分b)的适用的氨基改性的聚有机硅氧烷的种类不受特别限制并且包括宽范围的常规和可商购获得的材料,只要至少一个氨基基团位于聚有机硅氧烷的末端(链端)位置处即可。如以下实施例中所证实的,当与成分a)和c)组合使用时,包含位于聚有机硅氧烷链的末端位置处的氨基基团的聚有机硅氧烷物质的表现远优于具有仅位于侧链(中间)位置处的氨基基团的那些。虽然本发明的氨基硅氧烷可包含位于末端和侧链两个位置处的氨基基团,但在一类优选的实施方案中,该氨基基团主要位于末端位置处,即如通过29Si NMR测定,大于90重量%,并且更优选地大于95重量%,并且还更优选地大于99重量%的氨基基团位于末端位置处。这种聚合物包括直链和支链结构,优选直链聚合物。适用的聚合物优选地具有200AMU至10,000AMU(道尔顿),并且更优选地400AMU至8000AMU(道尔顿)的重均分子量(Mw)。适用的聚合物优选地具有如根据ASTM D2196-05在25℃下测量的2cSt至200cSt,更优选地5cSt至150cSt的粘度。可以组合使用不同的氨基改性的聚有机硅氧烷,例如具有不同化学结构、分子量和/或粘度的那些。代表性的氨基改性的聚有机硅氧烷包括具有以下通式的那些:
XR2SiO(RRSiO)qSiR2X
其中q为2至200,优选地25至100,R如上文所定义,并且X为包含一个或多个(优选地一至三个)含1至6个碳原子的伯胺或仲胺基团的氨基基团。代表性的氨基基团包括具有以下通式的那些:
-R’NR’R”’
其中R’是具有2至6个碳原子的二价烃基团(例如亚烷基基团),并且R”是相同或不同的并且选自H(氢)或具有1至6个碳原子的一价烃基团(例如烷基基团),其可以是未取代的或被一个或多个烃基团取代(使得这种经取代的一价烃基团中的总碳原子是1至6个),伯胺基团和仲胺基团包括具有1至6个碳原子的一价烃基团(例如烷基基团)。代表性示例包括:-(CH2)3NH2、-(CH2)3NHCH2CH2NH2、-(CH2)4NHCH2CH2NH2、-CH2CH(CH3)CH2NHCH2CH2NH2、-(CH2)3NHCH2CH2NHCH2CH2NH2和-(CH2)3NH(CH2)2CH(CH2CH2NH2)(CH2)3NH2。最优选的结构包括:-(CH2)3NH2和-CH2CHR”’CH2NHR”’,其中R”’是H或具有1至6个碳原子的烷基基团。适用的物质进一步描述于US9777105中。适用的可商购获得的氨基改性的聚有机硅氧烷包括:购自盖尔斯公司(Gelest)的DMS-A15、DMS-A21和DMS-A31。
c)封端异氰酸酯
指定为成分c)的适用的封端异氰酸酯的种类没有特别限制并且包括宽范围的常规和可商购获得的材料。如本文所用的术语“封端异氰酸酯”是指异氰酸酯和封端剂的反应产物,其中封端剂在热条件(即,在处理纺织品时通常使用的那些条件)下可从异氰酸酯中去除。常规的封端剂包括芳基醇、烷酮肟、芳基硫醇、有机活性氢化合物、亚硫酸氢钠和羟胺。优选的封端剂包括烷酮肟(酮肟),其可以在相对低的温度处解封端,诸如在典型的纺织品处理过程中使用的温度。出于本发明的目的,“芳族”封端聚异氰酸酯是优选的。在该上下文中,术语“芳族”意指具有至少一个芳族基团的异氰酸酯化合物,诸如基于甲苯二异氰酸酯、二苯基甲烷4,4’二异氰酸酯、二苯基甲烷2,4’二异氰酸酯、聚亚甲基-聚苯基异氰酸酯、4,4’亚甲基双酚异氰酸酯以及它们的衍生物的物质。用于制备该封端异氰酸酯的合适的异氰酸酯A(CNO)z是其中A为芳族化合物并且z为1、2、3或4的那些。这些包括异氰酸酯或衍生物,诸如甲苯二异氰酸酯、聚亚甲基聚苯基异氰酸酯和4,4’亚甲基双酚异氰酸酯,并且包括为此目的市售的那些芳族异氰酸酯。典型的商业产品包括以下产品:诸如甲苯二异氰酸酯和三羟甲基丙烷(1,1,1三羟甲基丙烷)的加合物DESMODUR CB-75(购自科思创公司(Covestro));基于异氰酸的聚亚甲基聚亚苯基酯的芳族异氰酸酯,诸如MONDUR MR-100(购自科思创公司),以及基于包含4,4’亚甲基双酚异氰酸酯的聚亚甲基聚苯基异氰酸酯的芳族异氰酸酯(购自陶氏化学公司)。可商购获得的还有现成的封端芳族异氰酸酯,诸如HYDROPHOBOL DL、PHOBOL XAN Extender(购自亨斯迈公司(Huntsman))、DM-6400、MEIKANATE FM-1、MEIKANATE ST、MEIKANATE PRO、MEIKANATE TP-10、MEIKANATE WEB、MEIKANATE ST(购自Meisei Chemical Works,Ltd.)。关于此类异氰酸酯的更多背景信息提供于US2019/0375897、US839255和US6451717中。
d)包含至少一个硅烷醇基团(-SiOH)的聚有机硅氧烷。
指定为组分d)的包含至少一个硅烷醇基团的适用的聚有机硅氧烷的种类不受特别限制并且包括宽范围的常规和可商购获得的材料。这种材料包括环状、直链和支链结构,优选直链聚合物。适用的聚合物优选地具有200AMU至5500AMU(道尔顿)的重均分子量(Mw)。适用的聚合物可具有根据ASTM D2196-05在25℃下测量的30cSt至100cSt的粘度。可以组合使用不同的聚有机硅氧烷,例如具有不同化学结构、分子量和/或粘度的那些。本发明的聚有机硅氧烷包含至少一个,优选地至少两个,并且更优选地至少三个硅烷醇(-SiOH)基团,其可位于聚硅氧烷主链的末端(端部)和/或中间(侧链)位置。在优选的实施方案中,-SiOH基团主要位于侧链位置处,即如通过29Si NMR测定,大于90重量%,并且更优选地大于95重量%,并且还更优选地大于99重量%的所有-SiOH基团位于沿着聚硅氧烷链的侧链位置处。本发明的聚有机硅氧烷优选地具有如通过FTIR测定的1重量%至10重量%的硅烷醇含量。代表性的聚有机硅氧烷包括具有以下通式的那些:
Y2RSiO(YRSiO)tSiRY2
其中t是2至50的数,Y可以相同或不同并且选自具有1至18个碳原子且更优选地1至8个碳原子的取代或未取代的一价烃基团和羟基基团(即满足上述标准的足够数目的羟基),并且R可以相同或不同并且选自具有1至18个碳原子且更优选地1至8个碳原子的取代或未取代的一价烃基团。代表性烃基团包括:a)烷基基团,诸如:甲基、乙基、丙基、丁基、戊基、己基、环己基和庚基;b)芳基基团,诸如苯基、甲苯基、二甲苯基和萘基;以及c)芳烷基基团,诸如苄基和苯乙基;然而,
优选甲基和苯基基团,最优选甲基。适用的可商购获得的产品包括:DOWSILTMQ1-3563流体和XIAMETERTMPMX-0930硅烷醇流体,均购自陶氏化学公司。
表面活性剂(乳化剂)
用于制备本发明乳液的适用的表面活性剂的种类没有特别限制,并且包括宽范围的常规和可商购获得的材料。表面活性剂可以是阴离子表面活性剂、阳离子表面活性剂、非离子表面活性剂、两性表面活性剂或它们的混合物,优选阳离子表面活性剂和非离子表面活性剂。
适用的阴离子表面活性剂的示例包括但不限于:高级脂肪酸的碱金属盐、胺盐或铵盐;烷芳基磺酸盐,诸如十二烷基苯磺酸钠、长链脂肪醇硫酸盐、烯烃硫酸盐和烯烃磺酸盐、硫酸化单酸甘油酯、硫酸化酯、磺化乙氧基化醇、磺基琥珀酸盐、烷磺酸盐、磷酸酯、烷基羟乙磺酸盐、烷基牛磺酸盐;烷基肌氨酸盐以及它们的混合物。适用的阴离子表面活性剂的另外的示例包括羧酸盐(2-(2-羟基烷氧基)乙酸钠)、氨基酸衍生物(N-酰基谷氨酸盐、N-酰基甘氨酸盐或酰基肌氨酸盐)、烷基硫酸盐、烷基醚硫酸盐及其氧乙烯化衍生物、磺酸盐、羟乙基磺酸盐和N-酰基羟乙基磺酸盐、牛磺酸盐(taurates)和N-酰基N-甲基牛磺酸盐、磺基琥珀酸盐、烷基磺基乙酸盐、磷酸盐和烷基磷酸盐、多肽、烷基聚葡萄糖苷的阴离子衍生物(酰基-D-半乳糖苷糖醛酸盐)和脂肪酸皂以及它们的混合物。适用的阴离子表面活性剂的商业示例包括:WA-100、SLS、A-16、B-11、B-19、TRITONTMQS-15、TRITONTMXN-45S和DOWFAXTM2A1。
适用的阳离子表面活性剂的示例包括但不限于烷基胺盐、季铵盐、锍盐和鏻盐。阳离子表面活性剂的适用的商业示例包括:16-29、18-50、ARLASILK EFA。ATLAS G-265、SYNPROLAM 35X15、PATC和BT-85。
适用的两性表面活性剂的示例包括但不限于咪唑啉化合物、烷基氨基酸盐、甜菜碱以及它们的混合物。
适用的非离子表面活性剂的示例包括但不限于:环氧乙烷与长链脂肪醇或脂肪酸(诸如C12-16醇)的缩合物、环氧乙烷与胺或酰胺的缩合物、环氧乙烷与环氧丙烷的缩合产物、甘油的酯、蔗糖、山梨糖醇、脂肪酸烷基醇酰胺、蔗糖酯、氟表面活性剂、脂肪胺氧化物以及它们的混合物。非离子表面活性剂的另外的示例包括:聚氧乙烯脂肪醇,诸如聚氧乙烯(23)月桂基醚、聚氧乙烯(4)月桂基醚;乙氧基化醇,诸如乙氧基化三甲基壬醇、C12-C14仲醇乙氧基化物、乙氧基化C10-Guerbet醇、乙氧基化异-C13醇;聚(氧乙烯)-聚(氧丙烯)-聚(氧乙烯)三嵌段共聚物(也称为泊洛沙姆);衍生自环氧丙烷和环氧乙烷向乙二胺的顺序加成的四官能聚醚聚(氧乙烯)-聚(氧丙烯)嵌段共聚物(也称为泊洛沙胺)、有机硅聚醚、聚氧乙烯烷基醚、聚氧乙烯烷基酚醚、聚氧乙烯月桂基醚、聚氧乙烯脱水山梨糖醇单油酸酯、聚氧乙烯烷基酯、聚氧乙烯脱水山梨糖醇烷基酯、聚乙二醇、聚丙二醇、二甘醇、乙氧基化三甲基壬醇和聚亚氧烷基二醇改性的聚硅氧烷表面活性剂,以及它们的组合。适用的非离子表面活性剂的另外的示例包括聚氧乙烯烷基醚、聚氧乙烯烷基酚醚、聚氧乙烯月桂基醚、直链伯醇烷氧基化物、直链仲醇烷氧基化物、烷基酚烷氧基化物、烯烃烷氧基化物、支链烷氧基化物、聚氧乙烯脱水山梨糖醇单油酸酯、聚氧乙烯烷基酯、聚氧乙烯脱水山梨糖醇烷基酯、聚乙二醇、聚丙二醇、二甘醇、乙氧基化三甲基壬醇、聚氧化烯取代的有机硅(耙形或ABn型)、有机硅烷醇酰胺、有机硅酯、有机硅糖苷以及它们的混合物。适用的非离子表面活性剂的另外的示例包括聚二甲基硅氧烷共聚多元醇、多元醇的脂肪酸酯(例如一-、二-、三-或倍半油酸山梨酯或甘油酯或一-、二-、三-或倍半硬脂酸山梨酯或甘油酯、月桂酸甘油酯或月桂酸聚乙二醇酯);聚乙二醇的脂肪酸酯(聚乙二醇单硬脂酸酯或单月桂酸酯);山梨醇的聚氧乙烯化的脂肪酸酯(硬脂酸酯或油酸酯);聚氧乙烯化的烷基(月桂基、十六烷基、硬脂基或辛基)醚。适用的商业非离子表面活性剂的示例包括:TERGITOLTM15-S-3、TERGITOLTM15-S-5、TERGITOLTM15-S-7、TERGITOLTM15-S-9、TERGITOLTM15-S-12、TERGITOLTM15-S-15、TERGITOLTM15-S-15、TERGITOLTM15-S-20、BRIJTML23、BRIJTML4、TO3、TO5、TO7、TO10、TO12、TO15、TO20、XP30、XP100和XP140。
适用的两性和两性离子表面活性剂的另外的示例包括甜菜碱、N-烷基酰氨基甜菜碱及其衍生物、蛋白质及其衍生物、甘氨酸衍生物、磺基甜菜碱、烷基聚氨基羧酸酯和烷基两性基乙酸酯,以及它们的混合物。
可以向水相中添加附加的水溶性成分,包括增稠剂和防腐剂。
在选定的实施方案中,本发明的乳液基本上不含以下成分中的一种或多种(包括这些成分的所有可能组合):
i)含氟聚合物;
ii)包含烯键式不饱和基团的有机材料(例如不饱和乙酸酯、烯丙基酯、乙烯基酯);
iii)包含烯键式不饱和基团(例如乙烯基)的聚有机硅氧烷;
iv)含铂催化剂;
v)树脂材料(例如聚硅氧烷树脂和聚氨酯树脂)和
vi)全金属催化剂。
在该上下文中,术语“基本上不含”意指基于不连续油相的总重量,小于1重量%,优选地小于0.5重量%,并且更优选地小于0.1重量%,并且还更优选地小于0.01重量%。
本发明的乳液可通过将上述成分a)、b)、c)和任选的d)与一种或多种表面活性剂在搅拌下在水中混合来制备。可使用任何已知技术进行混合。代表性混合装置包括均质器、声谱显示仪、转子-定子涡轮、胶体磨、微射流机、超声波仪、叶片、螺旋以及它们的组合。代表性方法描述于US6013682、US8877293和US2015/0010711中。在一个优选的实施方案中,将成分a)和任选的成分d)与表面活性剂在水中组合并混合以形成第一乳液,将成分b)与表面活性剂在水中组合并混合以形成第二乳液,将成分c)与表面活性剂在水中组合并混合以形成第三乳液。可使用均质器或声波探针来获得所需的粒度。可以储存第一、第二和第三乳液并随后在使用前合并。另选地,成分c)和/或d)可被包含在第一乳液(含有成分a))、第二乳液(含有组分b))或第三乳液中。
不连续油相的颗粒优选地具有如使用Malvern 3000并根据ISO 13320(2009)经由激光衍射测定的100nm至5000nm,并且更优选地100nm至2000nm的平均体积粒度“Dv(0.5)”。如本文所用,术语“颗粒”是指油相液滴。
用主题乳液处理纺织品的适用方法没有特别限制,并且包括通过浸渍、浸轧(例如经由辊轧机)、幕涂、刷涂、辊涂和喷涂方法如空气雾化喷涂、空气辅助喷涂、无空气喷涂、高体积低压喷涂和空气辅助无空气喷涂将乳液施加到纺织品上。然后将所得涂层在80℃至180℃的升高温度下干燥(固化)1至3分钟。干燥步骤的示例包括室温处的空气干燥、热空气干燥和红外加热。典型的涂层覆盖度在0.5至15克干重/平方米(g/m2)的范围内。
已经描述了本发明的许多实施方案,并且在一些情况下,某些实施方案、选择、范围、成分或其他特征已被表征为“优选的”。这种“优选”特征的名称绝不应被解释为本发明的必要或关键方面。表达的范围特别包括指定的终点。如本文所用,术语“分子量”和“Mw”是指如通过凝胶渗透色谱法(GPC)测量的重均分子量。
实施例:
除非另有说明,否则所有制备和测试在室温(RT)和标准压力(1atm或760mm Hg)下进行。以下材料用于制备和测试含水乳液:
表1:实施例中使用的材料的描述
根据以下方法制备样品乳液:
末端氨基1和末端氨基4的乳液:
通过在牙杯中组合相应的氨基硅氧烷(4.00g)、BRIJ L23(0.07g)、BRIJ L4(0.04g)和水(35.88g)并在Flak-Tek快速混合器(型号150.1FZV)上以3500rpm混合1分钟来制备氨基硅氧烷乳液。然后使用声波探针(Fisherbrand Model 705)在50%功率下30秒来减小乳液粒度。
末端氨基2的乳液:
通过在牙杯中组合末端氨基2(20.00g)、BRIJ L23(1.12g)、BRIJ L4(0.7g)、乙酸(10重量%水溶液,0.5g)和水(27.68g)并在Flak-Tek快速混合器(型号150.1FZV)上以3500rpm混合30秒来制备氨基硅氧烷乳液。将水(27.68g)加入混合物中,使过混合物在15000psi下两次通过1级均质器(APV Systems SPX 2000)。均化后,将乙酸(10重量%,2.65g)加入到135.95g乳液中。
侧链氨基1、2和3以及末端氨基3的乳液:
通过在牙杯中组合相应的氨基硅氧烷(4.00g)、BRIJ L23(0.07g)、BRIJ L4(0.05g)和水(35.88g),然后使用声波探针(Fisherbrand Model 705)在50%功率下均化1分钟来制备氨基硅氧烷乳液。
含有机氢硅氧烷的乳液:
向混合物中加入XIAMETERTMOFX-5084(60.51g)、BRIJ L23(1.12g)、BRIJ L4(0.61g)和水(4.5g),并在Flak-Tek快速混合器(150.1FZV型)上以3500rpm混合30秒。然后将乳液用水(33.26g)稀释,并在15000psi下两次通过1级均质器(APV Systems SPX 2000)。使用相同的程序制备含有DOWSILTMMH 1107FLUID(60.51g)的乳液。
1107/PDMS共混物乳液:
50cSt 200流体和DOWSILTMMH 1107流体的溶液通过以1∶1比例混合各组分直至均匀和澄清来制备。在塑料杯中向该溶液(27.99g)加入ARQUAD 16-29(2.16g)和水(4.04g),并在Flak-Tek快速混合器(型号150.1FZV)上以3500rpm混合30秒。用水(10.93g)稀释该乳液,并通过高速混合器以3500rpm混合30秒。
通过将上述乳液与表2a、2b、2c和2d中所示的任何附加成分(其中所有量以克计)混合来制备涂料乳液。然后通过浸轧将所得涂料乳液施加到来自伯灵顿的标准聚酯(PESStyle Number 4774 075)织物上,随后在Mathis烘箱(LTF 81782)中在160℃下固化3分钟。将所有经涂覆的织物样品在测试前在室温下调理至少24小时。然后使经涂覆的织物样品在室温/湿度下平衡约12小时。之后,使用ISO 9865“纺织品-通过邦迪斯门雨淋测试测定织物的拒水性”评价拒水性,其中将样品固定到样品架中并用水淋洒10分钟。由该测试可以确定三个参数:水通过织物的渗透、织物的吸水率和视觉外观(5=最好,1=最差/织物表面被水完全饱和)。吸水率通过:(最终织物重量-初始织物重量)/初始织物重量来计算。耐久性通过在多次洗涤/干燥循环后使用标准住宅洗涤器和干燥器使用Free洗涤剂进行邦迪斯门测试来测量。将洗涤循环设定为90℃,然后冷水漂洗。将干燥循环设定在高温处并自动感测关闭。
表2a.涂料乳液制剂和测试结果的总结:
表2b.涂料乳液制剂和测试结果的总结:
表2c.涂料乳液制剂和测试结果的总结:
表2d.涂料乳液制剂和测试结果的总结:
Claims (9)
1.一种含水乳液,其包含含水连续相和不连续油相,其中所述不连续油相包含以下成分:
a)50重量%至95重量%的聚有机氢硅氧烷;
b)0.1重量%至45重量%的氨基改性的聚有机硅氧烷,其包含至少一个位于末端位置处的氨基基团;和
c)5重量%至30重量%的封端异氰酸酯。
2.根据权利要求1所述的乳液,其中所述不连续油相包含:
i)0.5至1.5H重量%和
ii)0.004至0.2N重量%。
3.根据任一前述权利要求所述的乳液,其中所述不连续油相还包含成分d):0.1重量%至10重量%的包含至少一个硅烷醇基团的聚有机硅氧烷。
4.根据任一前述权利要求所述的乳液,其中成分a)具有500AMU至6000AMU的重均分子量(Mw),并且成分b)具有200AMU至10,000AMU的重均分子量(Mw)。
5.根据任一前述权利要求所述的乳液,其中成分b)由下式中的至少一者表示:i)(CH2)3NH2和ii)CH2CHR”’CH2NHR”’,其中R”’是H或具有1至6个碳原子的烷基基团。
6.根据任一前述权利要求所述的乳液,其中所述不连续油相包含以下成分:
a)60重量%至90重量%的聚有机氢硅氧烷;
b)1重量%至20重量%的氨基改性的聚有机硅氧烷,其包含至少一个位于末端位置处的氨基基团;和
c)10重量%至25重量%的封端异氰酸酯。
7.根据任一前述权利要求所述的乳液,其特征还在于基本上不含包含烯键式不饱和基团的有机材料。
8.根据任一前述权利要求所述的乳液,其特征还在于基本上不含含铂催化剂。
9.根据任一前述权利要求所述的乳液,其特征还在于基本上不含树脂材料。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US202163210517P | 2021-06-15 | 2021-06-15 | |
US63/210517 | 2021-06-15 | ||
PCT/US2022/072147 WO2022266566A1 (en) | 2021-06-15 | 2022-05-06 | Polysiloxane-based water repellants for textiles |
Publications (1)
Publication Number | Publication Date |
---|---|
CN117480297A true CN117480297A (zh) | 2024-01-30 |
Family
ID=82403623
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN202280042468.XA Pending CN117480297A (zh) | 2021-06-15 | 2022-05-06 | 用于纺织品的基于聚硅氧烷的防水剂 |
Country Status (5)
Country | Link |
---|---|
US (1) | US11976414B2 (zh) |
EP (1) | EP4355944A1 (zh) |
JP (1) | JP2024522600A (zh) |
CN (1) | CN117480297A (zh) |
WO (1) | WO2022266566A1 (zh) |
Family Cites Families (35)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US839255A (en) | 1905-05-05 | 1906-12-25 | Simplex Electric Heating Co | Circuit-opening device for electric heaters. |
US3247281A (en) | 1961-09-27 | 1966-04-19 | Union Carbide Corp | Water repellent compositions containing water soluble aminosilanes and aminosilicones as curing catalysts and process for treating substrates therewith |
US3436251A (en) | 1964-08-04 | 1969-04-01 | Midland Silicones Ltd | Process for rendering paper abrasion resistant,adhesive and water-repellent employing siloxane composition |
GB1543157A (en) | 1975-05-17 | 1979-03-28 | Dow Corning Ltd | Treatment of fibres |
GB1570983A (en) | 1976-06-26 | 1980-07-09 | Dow Corning Ltd | Process for treating fibres |
JPS5947628U (ja) | 1982-09-21 | 1984-03-29 | 森安 四郎 | ヘルメツト用帽子 |
JP2935879B2 (ja) * | 1990-09-05 | 1999-08-16 | 東レ・ダウコーニング・シリコーン株式会社 | 繊維処理剤組成物 |
US5409620A (en) | 1993-12-30 | 1995-04-25 | Dow Corning Corporation | Fiber treatment compositions containing organofunctional siloxanes and methods for the preparation thereof |
US5973068A (en) | 1996-11-07 | 1999-10-26 | Shin-Etsu Chemical Co., Ltd. | Silicone resin-containing emulsion composition, method for making same, and article having a cured film of same |
GB9708182D0 (en) | 1997-04-23 | 1997-06-11 | Dow Corning Sa | A method of making silicone in water emulsions |
US6451717B1 (en) | 1999-12-14 | 2002-09-17 | E. I. Du Pont De Nemours And Company | Highly durable oil/water repellents for textiles |
EP1148080A1 (de) | 2000-04-19 | 2001-10-24 | Ciba Spezialitätenchemie Pfersee GmbH | Polyorganosiloxangemische für die Behandlung von Fasermaterialien |
JP2002146680A (ja) | 2000-11-09 | 2002-05-22 | Dai Ichi Kogyo Seiyaku Co Ltd | セルロース系繊維布帛の反撥風合い加工処理剤及び加工方法 |
EP1377709B1 (en) | 2001-04-04 | 2013-09-11 | Healthtex Apparel Corp. | Improved polymer-grafted cotton fibers and products |
FR2831547B1 (fr) | 2001-10-26 | 2005-08-19 | Rhodia Chimie Sa | Formulation silicone liquide pour la realisation de revetements elastomeres reticules anti-adherents et hydrofuges sur support solide, par exemple en papier |
JP2004059609A (ja) | 2002-07-25 | 2004-02-26 | Miki Riken Kogyo Kk | 柔軟撥水剤 |
EP1699874B1 (en) | 2003-11-26 | 2010-03-10 | Dow Corning Corporation | Silicone polymer and organic polymer containing alloy and/or hybrid emulsion compositions |
JP4952882B2 (ja) | 2006-01-13 | 2012-06-13 | 信越化学工業株式会社 | 液状シリコーンゴムコーティング剤組成物、カーテンエアーバッグ及びその製造方法 |
DE102008002570A1 (de) | 2008-06-20 | 2009-12-24 | Wacker Chemie Ag | Nanopartikuläre Silikonorganocopolymere und deren Verwendung in Beschichtungsmitteln |
CN103025834A (zh) | 2010-08-03 | 2013-04-03 | 道康宁公司 | 有机硅胶乳液 |
US8329255B2 (en) * | 2010-11-05 | 2012-12-11 | Momentive Performance Materials Inc. | Durable non-fluorine water repellent agent and process for preparing same |
JP5947628B2 (ja) | 2011-06-14 | 2016-07-06 | 大原パラヂウム化学株式会社 | 繊維仕上げ用エマルジョン組成物及びその製造方法 |
JP2015510006A (ja) | 2012-02-08 | 2015-04-02 | ダウ コーニング コーポレーションDow Corning Corporation | コーティング応用例 |
WO2015156043A1 (ja) | 2014-04-10 | 2015-10-15 | 信越化学工業株式会社 | シリコーン組成物、シリコーンエマルション組成物及び繊維処理剤 |
EP3144326B1 (en) | 2014-05-12 | 2020-04-15 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Resin beads, method for manufacturing resin beads and product containing resin beads |
JP5735160B1 (ja) | 2014-06-19 | 2015-06-17 | ヤフー株式会社 | 広告配信管理装置、広告配信システム、広告配信管理方法および広告配信管理プログラム |
JP6219789B2 (ja) | 2014-07-25 | 2017-10-25 | 株式会社Kri | 撥水撥油性膜形成用塗布組成物及び塗布液並びに撥水撥油性膜 |
US10584263B2 (en) | 2014-09-23 | 2020-03-10 | Basf Se | Aqueous polymer-silicon oil hybrid composition |
DE102014220912A1 (de) * | 2014-10-15 | 2016-04-21 | Wacker Chemie Ag | Zusammensetzungen von Aminosiloxanen, Alkoxysiliciumverbindungen und Metallcarboxylaten |
JP6394493B2 (ja) | 2015-05-18 | 2018-09-26 | 信越化学工業株式会社 | ブロックポリイソシアネート含有硬化性シリコーン組成物及びそれを用いた繊維処理剤 |
JP6811037B2 (ja) | 2016-06-24 | 2021-01-13 | 日華化学株式会社 | 撥水剤組成物、及び撥水性繊維製品の製造方法 |
EP3577180B1 (en) | 2017-02-06 | 2021-03-31 | Dow Silicones Corporation | Emulsion, composition comprising same, film formed therewith, and related methods |
JP6877837B2 (ja) | 2017-06-28 | 2021-05-26 | 旭化成ワッカーシリコーン株式会社 | ブロックポリイソシアネート組成物を含有するシリコーンゴム組成物、コーティング物の製造方法およびコーティング物 |
EP3700988B1 (en) | 2017-10-23 | 2021-08-18 | Basf Se | Aqueous silicone polymer emulsion |
US20200332148A1 (en) | 2017-12-25 | 2020-10-22 | Nicca Chemical Co., Ltd. | Water repellent agent composition, and production method of water repellent fiber product |
-
2022
- 2022-05-06 CN CN202280042468.XA patent/CN117480297A/zh active Pending
- 2022-05-06 JP JP2023575642A patent/JP2024522600A/ja active Pending
- 2022-05-06 EP EP22738293.4A patent/EP4355944A1/en active Pending
- 2022-05-06 US US18/551,429 patent/US11976414B2/en active Active
- 2022-05-06 WO PCT/US2022/072147 patent/WO2022266566A1/en active Application Filing
Also Published As
Publication number | Publication date |
---|---|
EP4355944A1 (en) | 2024-04-24 |
US11976414B2 (en) | 2024-05-07 |
WO2022266566A1 (en) | 2022-12-22 |
US20240102233A1 (en) | 2024-03-28 |
JP2024522600A (ja) | 2024-06-21 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
AU624263B2 (en) | Stable emulsions containing amino polysiloxanes and silanes for treating fibers and fabrics | |
US20110311723A1 (en) | Silicate Shell Microcapsules For Treating Textiles | |
WO1997032917A1 (en) | Silicone aminopolyalkyleneoxide block copolymers | |
US20070166475A1 (en) | Treating textiles with emulsions containing silicone resins | |
JP2001226878A (ja) | 繊維処理用組成物 | |
US7329707B2 (en) | Partially quaternised, amino-functional organopolysiloxanes and their use in aqueous systems | |
JPH0469669B2 (zh) | ||
US20080107814A1 (en) | Treatment Of Fiberfill Fibers With Aqueous Dispersions Of Organopolysiloxanes | |
JPS6336399B2 (zh) | ||
CA2362197A1 (en) | Shear stable aminosilicone emulsions | |
US6756077B2 (en) | Water repellent textile finishes and method of making | |
EP0292963A2 (en) | Fiber-treatment composition | |
EP0474207A1 (en) | Fiber treatment agent composition | |
JPH10140480A (ja) | 繊維処理剤 | |
US11976414B2 (en) | Polysiloxane-based water repellants for textiles | |
CN110475928B (zh) | 粘固有有机硅的纤维及其制造方法 | |
JPH0593366A (ja) | ポリエステル繊維処理剤 | |
WO2022034829A1 (ja) | シリコーンエマルション組成物及び繊維処理剤 | |
JP7439339B2 (ja) | シリコーン樹脂と有機ポリマーとの相互侵入網目を含む水性エマルジョン | |
EP3653786A1 (en) | Functional-agent-containing fiber and method for manufacturing same | |
CN110462128B (zh) | 电子射线粘固用纤维处理剂 | |
EP1368525B1 (en) | Water repellent textile finishes and method of treating textiles | |
JPS58144179A (ja) | 耐久撥水性布帛とその製造方法 | |
JPH0953016A (ja) | 繊維処理剤 |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
PB01 | Publication | ||
PB01 | Publication | ||
SE01 | Entry into force of request for substantive examination | ||
SE01 | Entry into force of request for substantive examination |