CN1090918C - 聚硅氧烷组合物 - Google Patents
聚硅氧烷组合物 Download PDFInfo
- Publication number
- CN1090918C CN1090918C CN95196845A CN95196845A CN1090918C CN 1090918 C CN1090918 C CN 1090918C CN 95196845 A CN95196845 A CN 95196845A CN 95196845 A CN95196845 A CN 95196845A CN 1090918 C CN1090918 C CN 1090918C
- Authority
- CN
- China
- Prior art keywords
- oil
- acetate
- alkyl
- group
- composition
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 239000000203 mixture Substances 0.000 title claims abstract description 84
- 229920001296 polysiloxane Polymers 0.000 title claims description 12
- 239000004205 dimethyl polysiloxane Substances 0.000 claims abstract description 34
- 229920000435 poly(dimethylsiloxane) Polymers 0.000 claims abstract description 34
- 229940008099 dimethicone Drugs 0.000 claims abstract description 30
- 235000013870 dimethyl polysiloxane Nutrition 0.000 claims abstract description 27
- 239000000796 flavoring agent Substances 0.000 claims abstract description 25
- 235000019634 flavors Nutrition 0.000 claims abstract description 25
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 24
- 125000003545 alkoxy group Chemical group 0.000 claims abstract description 20
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 18
- 125000002252 acyl group Chemical group 0.000 claims abstract description 10
- 239000002826 coolant Substances 0.000 claims abstract description 8
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims abstract description 7
- 125000006353 oxyethylene group Chemical group 0.000 claims abstract description 7
- -1 polysiloxane Polymers 0.000 claims description 59
- 229920005862 polyol Polymers 0.000 claims description 30
- 150000003077 polyols Chemical class 0.000 claims description 30
- 239000000126 substance Substances 0.000 claims description 29
- 235000013305 food Nutrition 0.000 claims description 24
- 239000003921 oil Substances 0.000 claims description 21
- 235000019198 oils Nutrition 0.000 claims description 21
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 16
- 230000003115 biocidal effect Effects 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 12
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 11
- 239000003139 biocide Substances 0.000 claims description 11
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 claims description 10
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- HIGQPQRQIQDZMP-DHZHZOJOSA-N geranyl acetate Chemical compound CC(C)=CCC\C(C)=C\COC(C)=O HIGQPQRQIQDZMP-DHZHZOJOSA-N 0.000 claims description 6
- DTUQWGWMVIHBKE-UHFFFAOYSA-N phenylacetaldehyde Chemical compound O=CCC1=CC=CC=C1 DTUQWGWMVIHBKE-UHFFFAOYSA-N 0.000 claims description 6
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- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 claims description 4
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- UWKAYLJWKGQEPM-LBPRGKRZSA-N linalyl acetate Chemical compound CC(C)=CCC[C@](C)(C=C)OC(C)=O UWKAYLJWKGQEPM-LBPRGKRZSA-N 0.000 claims description 4
- HLCSDJLATUNSSI-JXMROGBWSA-N (2e)-3,7-dimethylocta-2,6-dienenitrile Chemical compound CC(C)=CCC\C(C)=C\C#N HLCSDJLATUNSSI-JXMROGBWSA-N 0.000 claims description 3
- WNJSKZBEWNVKGU-UHFFFAOYSA-N 2,2-dimethoxyethylbenzene Chemical compound COC(OC)CC1=CC=CC=C1 WNJSKZBEWNVKGU-UHFFFAOYSA-N 0.000 claims description 3
- MTDAKBBUYMYKAR-UHFFFAOYSA-N 3,7-dimethyloct-6-enenitrile Chemical compound N#CCC(C)CCC=C(C)C MTDAKBBUYMYKAR-UHFFFAOYSA-N 0.000 claims description 3
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- 230000003647 oxidation Effects 0.000 claims description 3
- 238000007254 oxidation reaction Methods 0.000 claims description 3
- 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 claims description 3
- GEWDNTWNSAZUDX-WQMVXFAESA-N (-)-methyl jasmonate Chemical compound CC\C=C/C[C@@H]1[C@@H](CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-WQMVXFAESA-N 0.000 claims description 2
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- DSSYKIVIOFKYAU-XCBNKYQSSA-N (R)-camphor Chemical compound C1C[C@@]2(C)C(=O)C[C@@H]1C2(C)C DSSYKIVIOFKYAU-XCBNKYQSSA-N 0.000 claims description 2
- CDOSHBSSFJOMGT-JTQLQIEISA-N (R)-linalool Natural products CC(C)=CCC[C@@](C)(O)C=C CDOSHBSSFJOMGT-JTQLQIEISA-N 0.000 claims description 2
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- WRFXXJKURVTLSY-UHFFFAOYSA-N 2,6-dimethyloctan-2-ol Chemical compound CCC(C)CCCC(C)(C)O WRFXXJKURVTLSY-UHFFFAOYSA-N 0.000 claims description 2
- MJTPMXWJHPOWGH-UHFFFAOYSA-N 2-Phenoxyethyl isobutyrate Chemical compound CC(C)C(=O)OCCOC1=CC=CC=C1 MJTPMXWJHPOWGH-UHFFFAOYSA-N 0.000 claims description 2
- PJXHBTZLHITWFX-UHFFFAOYSA-N 2-heptylcyclopentan-1-one Chemical compound CCCCCCCC1CCCC1=O PJXHBTZLHITWFX-UHFFFAOYSA-N 0.000 claims description 2
- RIWRBSMFKVOJMN-UHFFFAOYSA-N 2-methyl-1-phenylpropan-2-ol Chemical compound CC(C)(O)CC1=CC=CC=C1 RIWRBSMFKVOJMN-UHFFFAOYSA-N 0.000 claims description 2
- HQWYOJGMWNFPFV-UHFFFAOYSA-N 2-methylidene-1-phenylheptan-1-one Chemical compound C(CCCC)C(C(=O)C1=CC=CC=C1)=C HQWYOJGMWNFPFV-UHFFFAOYSA-N 0.000 claims description 2
- WRMNZCZEMHIOCP-UHFFFAOYSA-N 2-phenylethanol Chemical compound OCCC1=CC=CC=C1 WRMNZCZEMHIOCP-UHFFFAOYSA-N 0.000 claims description 2
- DLHQZZUEERVIGQ-UHFFFAOYSA-N 3,7-dimethyl-3-octanol Chemical compound CCC(C)(O)CCCC(C)C DLHQZZUEERVIGQ-UHFFFAOYSA-N 0.000 claims description 2
- MBZRJSQZCBXRGK-UHFFFAOYSA-N 4-tert-Butylcyclohexyl acetate Chemical compound CC(=O)OC1CCC(C(C)(C)C)CC1 MBZRJSQZCBXRGK-UHFFFAOYSA-N 0.000 claims description 2
- ZGZYALXYGDOZED-UHFFFAOYSA-N C(C)(=O)OC=C.C(CCCCCCCCCC)(C(=O)O)C(=O)O Chemical compound C(C)(=O)OC=C.C(CCCCCCCCCC)(C(=O)O)C(=O)O ZGZYALXYGDOZED-UHFFFAOYSA-N 0.000 claims description 2
- 241000218645 Cedrus Species 0.000 claims description 2
- 241000723346 Cinnamomum camphora Species 0.000 claims description 2
- 241000402754 Erythranthe moschata Species 0.000 claims description 2
- 235000019501 Lemon oil Nutrition 0.000 claims description 2
- 244000227633 Ocotea pretiosa Species 0.000 claims description 2
- 235000004263 Ocotea pretiosa Nutrition 0.000 claims description 2
- 235000019502 Orange oil Nutrition 0.000 claims description 2
- 240000000783 Origanum majorana Species 0.000 claims description 2
- 235000006297 Origanum majorana Nutrition 0.000 claims description 2
- 240000007673 Origanum vulgare Species 0.000 claims description 2
- 235000004383 Origanum vulgare subsp. vulgare Nutrition 0.000 claims description 2
- 235000010450 Pino mugo Nutrition 0.000 claims description 2
- 241001136577 Pinus mugo Species 0.000 claims description 2
- 244000223014 Syzygium aromaticum Species 0.000 claims description 2
- 235000016639 Syzygium aromaticum Nutrition 0.000 claims description 2
- ZOJBYZNEUISWFT-UHFFFAOYSA-N allyl isothiocyanate Chemical compound C=CCN=C=S ZOJBYZNEUISWFT-UHFFFAOYSA-N 0.000 claims description 2
- SESFRYSPDFLNCH-UHFFFAOYSA-N benzyl benzoate Chemical compound C=1C=CC=CC=1C(=O)OCC1=CC=CC=C1 SESFRYSPDFLNCH-UHFFFAOYSA-N 0.000 claims description 2
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- XSNQECSCDATQEL-UHFFFAOYSA-N dihydromyrcenol Chemical compound C=CC(C)CCCC(C)(C)O XSNQECSCDATQEL-UHFFFAOYSA-N 0.000 claims description 2
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- 239000003120 macrolide antibiotic agent Substances 0.000 claims description 2
- 239000001780 majorana hortensis moench (origanum majorana l.) Substances 0.000 claims description 2
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- GEWDNTWNSAZUDX-UHFFFAOYSA-N methyl 7-epi-jasmonate Natural products CCC=CCC1C(CC(=O)OC)CCC1=O GEWDNTWNSAZUDX-UHFFFAOYSA-N 0.000 claims description 2
- OSWPMRLSEDHDFF-UHFFFAOYSA-N methyl salicylate Chemical compound COC(=O)C1=CC=CC=C1O OSWPMRLSEDHDFF-UHFFFAOYSA-N 0.000 claims description 2
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- RJSZFSOFYVMDIC-UHFFFAOYSA-N tert-butyl n,n-dimethylcarbamate Chemical compound CN(C)C(=O)OC(C)(C)C RJSZFSOFYVMDIC-UHFFFAOYSA-N 0.000 description 1
- OGWLTJRQYVEDMR-UHFFFAOYSA-F tetramagnesium;tetracarbonate Chemical compound [Mg+2].[Mg+2].[Mg+2].[Mg+2].[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O.[O-]C([O-])=O OGWLTJRQYVEDMR-UHFFFAOYSA-F 0.000 description 1
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- A23L27/70—Fixation, conservation, or encapsulation of flavouring agents
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Abstract
一种聚硅氧烷组合物,其中包含一种二甲聚硅氧烷共聚多元醇,它选自具有以下结构式(I)的烷基和烷氧基二甲聚硅氧烷共聚多元醇:其中的X选自氢原子,具有1至约16个碳原子的烷基,烷氧基和酰基,Y选自具有约8至约22个碳原子的烷基和烷氧基,n是0至约200,m是约1至约40,q是约1至100,残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000,x和y为能使氧乙烯基∶氧丙烯基的重量比为约100∶0至0∶100之值。该组合物能提供改善的表面残留性、作用和/或效力。
Description
发明领域
本发明涉及含聚硅氧烷的组合物及其在例如个人保健产品、洗衣店用和家用的清洁剂、漂白组合物等各种日常用品中的用途。具体地说,涉及作为亲脂体的食用香精、日化香精、清凉剂或抗微生物剂为基础的含聚硅氧烷的亲脂性组合物,它们对被其所处理的表面(例如牙齿、假牙、皮肤、头发、衣物、餐具、工作台表面等)表现出改善的滞留性、作用和/或效力。此外,本发明还涉及另外包含例如日化香精、食用香精等对漂白敏感的成份的含聚硅氧烷的组合物,它表现出提高的稳定性。
发明背景
亲脂性组合物,例如食用香精、日化香精、清凉剂和消毒剂组合物被广泛地直接使用或用在各种日用品中,包括化妆品,口腔和牙科用组合物,漂白、餐具洗涤、硬表面清洁产品和洗衣剂等。亲脂性组合物的一个共同问题是有关改善亲脂性成份的表面直接性或残留性。在很多(如果说不上是大多数)日用场合,为了例如加强香味或香气、或提高抗微生物的效力,人们需要加强亲脂体的表面残留性。
例如,现代的牙科及假牙制品中通常含有抗牙斑和/或抗牙石试剂,以及抗微生物试剂和食用香精。抗微生物作用可以通过减少口腔/假牙中的细菌数量或将被药物膜捕获的细菌杀死而阻止其继续生长和代谢来影响牙斑的形成。食用香精可以通过除臭作用来改善口臭的问题。有些抗微生物剂,例如醇还能够起除口臭剂的作用。但是,抗微生物剂的作用很大程度上取决于其在口腔/假牙中的留存,尤其是它们在有牙斑形成的牙齿/假牙表面的留存。
已知牙科制剂中的一个典型的缺点是只有相当短的时间,即刷牙和漱口的时间,可供抗微生物剂起作用。由于洁齿制剂是非经常使用的,大多数一天使用一到两次,使得这一问题更难解决。结果,大多数人较长的刷牙间隔提供了最佳的牙斑形成条件。
在许多其它个人及日用应用中,人们需要提供强化的表面直接性。例如洗衣剂可通过提高日化香精在织物表面的直接性从而加强洗涤后或使用中的芳香而获得品质上的改善。强化的抗微生物的直接性因为能够消除与汗液或其它污物有关的臭味也是十分有益的。强化的日化香精直接性在高级调香化妆品中也是十分有价值的。另一方面,强化的清凉剂直接性在治疗咳嗽/感冒的产品中是十分有用的。
所以,人们一直需要开发出一种有改善的表面残留性、作用和/或抗微生物效力的亲脂性组合物。
亲脂性组合物,例如日化香精、食用香精等在含漂白剂的组合物中的使用也会产生许多问题,尤其是与漂白剂作用后造成的香气或香味的特性或强度损失。漂白剂的效力也会受到不利的影响。所以,需要提高含有对漂白剂敏感的组份的漂白组合物的稳定性和有效性。
将聚硅氧烷包含在洁齿组合物中是已知的,据说能够覆盖牙齿表面而防止龋齿和牙斑。例如,GB-A-689,679揭示了一种漱口剂,其中含有用于防止牙垢、牙斑、牙石和食物碎屑在牙齿表面粘附或将它们去除的有机聚硅氧烷。漱口剂中可含有消毒化合物,例如百里酚,和食用香精和日化香精。
US-A-2,806,814揭示了一种牙科制剂,其中包含作为有效成份的氨基羧酸的高级脂肪族酰胺和聚硅氧烷化合物的混合物。该专利指出,聚硅氧烷化合物可用于防止牙垢、牙斑、牙石等在牙齿上的粘附或有助于将它们清除。聚硅氧烷化合物被认为在加强有效成份的抗菌和防酸作用方面起着增效剂的作用。二甲基聚硅氧烷被认为尤其有效。其中可以包含调味油和/或醇。
US-A-3624120揭示了一种环硅氧烷季铵盐聚合物,它被用作阳离子表面活性剂、杀菌剂和防龋齿剂。
所以,本发明提供了食用香精、日化香精、清凉剂、抗微生物剂或其它的亲脂性组合物,它具有得到改善的表面直接性、作用和/或效力。
本发明还提供了一种漂白剂组合物,其中包含一种无机过酸盐漂白剂和一种亲脂性组合物,例如食用香精和/或日化香精,而且它具有提高的稳定性。
发明概述
根据第一方面的内容,本发明提供了一种聚硅氧烷组合物,其中包含一种二甲聚硅氧烷共聚多元醇,选自具有以下结构式(I)的烷基和烷氧基二甲聚硅氧烷共聚多元醇:其中的X选自氢原子,具有1至约16个碳原子的烷基,烷氧基和酰基,Y选自具有约8至约22个碳原子的烷基和烷氧基,n是0至约200,m是约1至约40,q是约1至100,残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000,约250至约1000较好,x和y之值能使氧乙烯基∶氧丙烯基的重量比为约100∶0至0∶100,约100∶0至约20∶80较好。
本发明还涉及将二甲聚硅氧烷共聚多元醇与选自食用香精、日化香精、生理清凉剂、抗微生物剂及其混合物的亲脂体联用以改善表面直接性,其中的二甲聚硅氧烷共聚多元醇选自具有结构式(I)的烷基-和烷氧基-二甲聚硅氧烷共聚多元醇。
根据本发明另一方面的内容,提供了一种漂白剂组合物,其中包含一种无机过酸盐漂白剂,一种选自食用香精、日化香精、生理清凉剂、抗微生物剂及其混合物的亲脂体,和具有结构式(I)的烷基-和烷氧基-二甲聚硅氧烷共聚多元醇:其中的X选自氢原子,具有1至约16个碳原子的烷基,烷氧基和酰基,Y选自具有约8至约22个碳原子的烷基和烷氧基,n是0至约200,m是约1至约40,q是约1至100,残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000,x和y之值能使氧乙烯基∶氧丙烯基的重量比为约100∶0至0∶100。
本发明还涉及将二甲聚硅氧烷共聚多元醇与无机过酸盐漂白剂和选自食用香精、日化香精、生理清凉剂、抗微生物剂及其混合物的亲脂体联用以提高亲脂体的稳定性,其中的二甲聚硅氧烷共聚多元醇选自具有结构式(I)的烷基-和烷氧基-二甲聚硅氧烷共聚多元醇。
本文中的百分数和比率都是按组合物的总重计算的,除非另作说明。
本发明的组合物因而含有某种二甲聚硅氧烷共聚多元醇除斑剂和选自食用香精、日化香精、生理清凉剂、抗微生物剂及其混合物的亲脂体。本发明的其它组合物则取漂白剂和/或洗涤剂组合物的形式,其中包含二甲聚硅氧烷共聚多元醇除斑剂和亲脂体。
一般而言,二甲聚硅氧烷共聚多元醇选自具有结构式(I)的烷基-和烷氧基-二甲聚硅氧烷共聚多元醇:其中的X选自氢原子,具有1至约16个碳原子的烷基,烷氧基和酰基,Y选自具有约8至约22个碳原子的烷基和烷氧基,n是0至约200,m是约1至约40,q是约1至100,残基(C2H4O-)x(C3H6O-)yX的分子量为约50至约2000,约250至约1000较好,x和y之值能使得氧乙烯基∶氧丙烯基的重量比为约100∶0至0∶100,约100∶0至约20∶80较好。
在较好的实施方式中,二甲聚硅氧烷共聚多元醇选自C12至C20烷基二甲聚硅氧烷共聚多元醇及其混合物。极好的是商品名为Abil EM90的十六烷基二甲聚硅氧烷共聚多元醇。二甲聚硅氧烷共聚多元醇的含量(按重量计)通常为约0.01%至25%,较好的是约0.1%至约5%,更好的是约0.5%至约1.5%。
本发明的组合物还宜包含一种亲脂性化合物。通常,在此适用的亲脂性化合物是可在二甲聚硅氧烷共聚多元醇中溶解或增溶的油状物质,其在25℃时的重量溶解度至少约为1%,至少约5%更好。较好的亲脂性化合物选自食用香精、日化香精、生理清凉剂和抗微生物化合物。二甲聚硅氧烷共聚多元醇起着加强亲脂性化合物与被其所处理的表面的直接性的作用,由此加强和/或延长食用香精、日化香精或清凉剂的作用和/或抗微生物效力。
在此适用的亲脂性食用香精包含一种或一种以上选自冬青油、牛至油(oreganooil)、桂叶油、薄荷油、留兰香油、丁子香油、鼠尾草油、黄樟油、柠檬油、橙油、茴香油、苯甲醛、苦杏仁油、樟脑、雪松叶油、甘牛至油、香茅油、熏衣草油、芥末油、松油、松针油、迷迭香油、百里香油、肉桂油及其混合物的调味组份。
在此适用的亲脂性日化香精包含一种或一种以上已知日化香精组合物,包括日化香精油,净油,树脂等天然产物,和烃、醇、醛、酮、醚、酸、酯、缩醛、缩酮、腈等合成日化香精组份,包括饱和的和不饱和的化合物,脂肪族、羧酸和杂环化合物。在此适用的日化香精的实例包括乙酸香叶酯,乙酸里哪酯,香茅醇乙酸酯,乙酸二氢月桂烯酯,乙酸萜品酯,乙酸三环癸酯,丙酸三环癸酯,乙酸2-苯基乙酯,乙酸苄酯,水杨酸苄酯,苯甲酸苄酯,乙酸甲基苯基原酯,水杨酸戊酯,二氢茉莉酸甲酯,异丁酸苯氧基乙酯,橙花醇乙酸酯,乙酸三氯甲基-苯基甲酯,乙酸对叔丁基环己酯,乙酸异壬酯,乙酸柏木酯,乙酸韦惕蔚酯,苯醇,2-苯基乙醇,里哪醇,四氢里哪醇,香茅醇,二甲基苄基甲醇,二氢月桂烯醇,四氢月桂烯醇,萜品醇,丁子香酚,香叶醇,韦惕蔚醇,3-异莰基-环己醇,2-甲基-3-(对叔丁基苯基)-丙醇,2-甲基-3-(对异丙基苯基)-丙醇,3-(对叔丁基苯基)-丙醇,橙花醇,α-正戊基肉桂醛,α-己基肉桂醛,4-(4-羟基-4-甲基戊基)-3-环亚己基甲醛,4-(4-甲基-3-戊烯基)-3-环亚己基甲醛,4-乙酰氧-3-戊基-四氢吡喃,2-正庚基-环戊酮,3-甲基-2-戊基-环戊酮,正癸醛,正十二烷醛,羟基香茅醛,苯乙醛缩二甲醇,苯乙醛缩二乙醇,香叶腈,香茅腈,柏木基甲基醚,异长叶酮,茴香醛腈,茴香醛,天芥菜精,香豆素,香草醛,氧化二苯基,芷香酮,甲基芷香酮,异甲基芷香酮,甲基芷香酮,顺式-3-己醇及其酯,1,2-二氢化茚麝香,1,2,3,4-四氢化萘麝香,异苯并二氢呋喃麝香,大环酮,大环内酯麝香,十三烷二酸乙烯酯,芳香族硝基麝香,及其混合物。
在此适用的亲脂性抗微生物剂包括百里酚,醇,二氯苯氧氯酚,4-己基间苯二酚,苯酚,桉叶油素,苯甲酸,过氧化苯甲酰,对羟基苯甲酸甲酯,对羟基苯甲酸丙酯,水杨酰胺,及其混合物。
在此适用的生理清凉剂包括羧酰胺,烷酯和烷醚,及其混合物。
在此适用的烷醚具有以下结构式:其中的R5是任选的含有多至25个碳原子的羟基取代的脂肪族基团,以多至5个碳原子为佳,其中的X是氢原子或羟基,例如可以商品名Takasago向TakasagoInternational Corporation购得的那些。
用于本发明组合物的一种特别好的清凉剂是Takasago 10(3-1-氧基丙-1,2-二醇(MPD))。MPD是1-醇的单甘油衍生物,具有优良的清凉作用。
最有用的羧酰胺是Wason等,1979年1月23日的US-A-4,136,163中和Rawsell等,1980年10月28日的US-A-4,230,688中揭示的那些。
亲脂性化合物在本发明组合物中重量含量通常为约0.01%至10%,较好的是约0.05%至约5%,约0.1%至3%更好。
本发明组合物可任选地包含一种或一种以上表面活性剂,这在用于增溶亲脂体及提高效力的本发明亲脂性组合物中格外地好。合适的表面活性剂包括非皂阴离子,非离子,阳离子,两性离子和两性有机合成洗涤剂。在Gieske等,1977年9月27日的US-A-4,051,234中描述了许多合适的这类试剂。
在此适用的表面活性剂实例包括用每摩尔约0.5至约20摩尔环氧乙烷乙氧基化的C6-C18烷基硫酸盐和烷基醚硫酸盐;阴离子磺酸盐,包括C5-C20线型烷基苯磺酸盐,磺酸烷基酯,C6-C24烯烃磺酸盐,磺化聚羧酸,烷基甘油磺酸盐,脂肪酰甘油磺酸盐,及其混合物;羧酸盐阴离子,包括C6至C18伯、仲烷基羧酸盐,乙氧基羧酸盐和聚乙氧基聚羧酸盐表面活性剂,其平均乙氧基化程度为约1至约10;C5至C17肌氨酸盐,例如椰子酰肌氨酸钠,月桂基肌氨酸钠(Hamposyl-95 ex W.R.Grace);环氧乙烷或环氧丙烷与脂肪酸、脂肪醇、脂肪酰胺、多元醇(例如脱水山梨醇单硬脂酸酯,脱水山梨醇油酸酯),烷基苯酚(例如Tergitol)和聚环氧丙烷和聚氧丁烯(例如Pluronics)的缩合产物;US-A-4,565,647中揭示的烷基多糖;氧化胺,例如氧化二甲基椰子胺(dimethyl cocamine oxide),氧化二甲基月桂基胺和氧化椰子烷基二甲基胺(cocoalkyldimethyl amine oxide)(Aromox);多乙氧基醚,例如吐温40和吐温80(Hercules);脱水山梨醇硬脂酸酯,脱水山梨醇单油酸酯等;阳离子表面活性剂,例如氯化十六烷基吡啶鎓,溴化十六烷基三甲基铵,氯化二异丁基苯氧基乙氧基乙基-二甲基苄基铵和硝酸椰子烷基三甲基铵。
考虑到亲脂体的增溶,在此特别好的是非离子表面活性剂。在此适用的一种非离子表面活性剂具有以下结构通式:其中R1是具有8至22,以10至20个为宜碳原子的烷基或烯基苯基基团,m和n分别代表0-80和2-80。通常避免短链烷基,这是出于对效力的考虑,而且因为这类表面活性剂中未反应的脂肪醇会造成异味,有时会引起皮肤炎症。可以理解,这类表面活性剂通常是具有不同乙氧基化/丙氧基化程度的混合物,所以,m和n分别代表丙氧基化基团和乙氧基化基团数。具有上述一般形式的非离子表面活性剂包括混合的烷氧基化基团,其中的m和n都在约2至80之间,m最好为约2至约20,约3至约10更好,n最好为约2至约60,约5至约50更好。这类物质之一是PPG-5-cetech-20(Croda Inc提供,商品名为Procetyl AWS),其中的m和n分别为5和20。其它合适的非离子表面活性剂包括聚乙氧基化表面活性剂,例如乙氧基化烷基苯酚醚,尤其是具有8-16EO的辛基-和壬基酚醚;乙氧基化脂肪族C8-C20醇,它们可以是线型性或支链的,具有8至16,以9至15为佳的EO;以及乙氧基化氢化蓖麻油。
通常,表面活性剂与日化香精、清凉剂或其它油性物质之比在约50∶1至1∶10,约20∶1至1∶2较好,约10∶1至1∶1更好。
本发明的漂白组合物还包含一种或一种以上漂白剂,可以任选地与有机过氧酸前体、泡腾剂、螯合剂等联用。
漂白剂是无机过酸盐形式的,而且可以选自任意已知用在日用漂白、去污、假牙清洁剂等中的熟知的漂白剂,例如过硫酸碱金属和铵盐,一水合和四水合过硼酸盐,过碳酸盐(可以如GB-A-1,466,799中所述进行涂覆)和过磷酸盐,以及碱金属和碱土金属的过氧化物。合适的漂白剂实例包括过硫酸的钾、铵、钠和锂盐和一水合及四水合过硼酸盐,焦磷酸钠过氧水合物,以及镁、钙、锶、锌的过氧化物。但是,在此优选的是其中的过硫酸、过硼酸和过碳酸碱金属盐,尤其是过硼酸和过碳酸碱金属盐。
漂白剂在本发明漂白组合物中含量一般为约5%至70%,约10%至50%更好。
漂白剂中还可以包含泡腾剂,它在较好的实例中是固体物质形式的,可在水中伴以泡腾而放出二氧化碳或氧气。泡腾剂可以选自在酸性、中性或碱性pH条件下可起作用的起泡剂,但较好的是由在酸性或中性pH下有效或最有效的起泡剂与在碱性pH下有效或最有效的起泡剂混合而成。在酸性或中性pH下有效的泡腾剂包含至少一种碱金属碳酸盐或碳酸氢盐(例如碳酸氢钠、碳酸钠、碳酸氢三钠、碳酸钾、碳酸氢钾或它们的混合物)与至少一种无毒、生理上合适的有机酸(例如酒石酸、富马酸、柠檬酸、苹果酸、马来酸、葡糖酸、琥珀酸、水杨酸、己二酸或氨基磺酸、富马酸钠、酸式磷酸钠或钾、盐酸甜菜碱、或它们的混合物)组成的混合物。其中,优选的是苹果酸。在碱性pH下有效的泡腾剂包括过酸盐,例如前述过氧化硼酸、过硼酸的碱金属和碱土金属盐、过硫酸盐、过碳酸盐、过磷酸盐、及它们的混合物,例如某种碱金属的过硼酸盐(无水、一水合或四水合)与单过硫酸盐的混合物,例如E I du Point de Nemours Co.出售的Caroat,这是一种2∶1∶1的单过硫酸盐、硫酸钾和硫酸氢钾的混合物,其活泼氧含量约为4.5%。
在用于假牙清洁剂的较好的漂白组合物中,固体物质包含一种碳酸(氢)盐/酸泡腾剂对,任选地与过硼酸盐/过硫酸盐氧泡腾剂联用。两种泡腾剂的联用利于为达到最佳的清洁和抗菌活性所需的最佳的溶解性和pH条件。碳酸(氢)盐组份在组合物总量中通常占约5%至65%,较好的是25%至55%;酸组份在组合物总量中通常占约5%至50%,约10%至约30%更好。
本发明在漂白剂中还可以补充以已知的这类制剂中的其它组份。一种特别好的另外的组份是有机过氧酸前体,可笼统地将其定义为在后文过酸形成试验中滴定度至少为1.5ml 0.1N硫代硫酸钠的化合物。
将下列物质溶解在1000ml蒸馏水中,制备试验溶液:
焦磷酸钠
(Na4PO2O7·10H2O) 2.5g
过硼酸钠
(NaBO2·H2O2·3H2O),具有10.4%的溶解氧 0.615g
十二烷基苯磺酸钠 0.5g
在60℃时,向此溶液中加入一定量的活化剂,加量为对于每一个可获得的氧原子加入一分子当量的活化剂。
剧烈搅拌加入活化剂后的混合物,并将其维持在60℃,加入后5分钟,取100ml溶液,立即移液到250g碎冰和15ml冰醋酸的混合物上。然后加入碘化钾(0.4g),立即以淀粉为指示剂,用0.1N硫代硫酸钠滴定释放出的碘,直到蓝色第一次褪去。所用的硫代硫酸钠的毫升数就是漂白活化剂的滴定度。
有机过酸前体通常是具有一个或一个以上易于水解的酰基基团的化合物。较好的活化剂是N-酰基或O-酰基类的化合物,其中包含一个R-CO基团,其中的R是具有1至20个碳原子的烃或取代烃基团。合适的过酸前体实例包括:
1)结构式为RCONR1R2的酰基有机胺,其中的RCO是羧酰基,R1是酰基,R2是一个有机基团,正如US-A-3,117,148中所述。此类化合物的实例包括:
a)N,N-二乙酰苯胺和N-乙酰苯邻二甲酰亚胺;
b)N-酰基乙内酰脲,例如N,N-二乙酰基-5,5-二甲基乙内酰脲;
c)多酰基化的亚烷基二胺,例如N,N,N’,N’-四乙酰基乙二胺(TAED)和其相应的亚己基二胺(TAHD)衍生物,正如GB-A-907,356,GB-A-907,357和GB-A-907,358中所揭示的;
d)酰基化的甘脲,例如四乙酰基甘脲,正如GB-A-1,246,338,GB-A-1,246,339和GB-A-1,247,429中所揭示的。
2)酰基化的胺磺酰,例如N-甲基N-苯甲酰基-甲磺酰胺和N-苯基-N-乙酰基-甲磺酰胺,正如GB-A-3,183,266中所揭示的。
3)GB-A-836,988,GB-A-963,135和GB-A-1,147,871中所揭示的羧酸酯。此类化合物的实例包括乙酸苯酯,乙酰氧基苯磺酸钠,乙酸三氯乙酯,山梨醇六乙酸酯,果糖五乙酸酯,对硝基苯甲醛二乙酸酯,乙酸异丙烯酯,乙酰基乙酰氧肟酸和乙酰基水杨酸。其它实例是苯酚或取代苯酚与α氯代低级脂肪族羧酸形成的酯,例如氯乙酰基苯酚和氯乙酰基水杨酸的酯,正如US-A-3,130,165所述。
4)通式为AeL的羧酸酯,其中的Ac是有机羧酸的酰基部分,该有机羧酸任意地具有一个C6-C20取代、直链或支链的烷基或烯基部分或一个C6-C20取代芳基,L是离去基团,其共轭酸的pKa在4至13之间,例如羟苯磺酸酯或羟苯甲酸酯。此类化合物中之较好者:
a)Ac是R3-CO,R3是直链或支链烷基,具有6至20碳原子,6至12为佳,7至9个更好,其中从羰基碳开始并将其包括在内的最长的直链烷基包含5至18个碳原子,以5至10个为佳,R3可以任选地被Cl、Br、OCH3或OC2H5取代(最好在羰基碳的α位)。此类物质的实例包括3,5,5-三甲基己酰氧基苯磺酸钠,3,5,5-三甲基己酰氧基苯甲酸钠,2-乙基己酰氧基苯磺酸钠,壬酰氧基苯磺酸钠和辛酰氧基苯磺酸钠,其中的酰氧基最好是对位取代的;
b)Ac的通式为R3(AO)mXA,其中R3是一个直链或支链烷基或烷基芳基,在其烷基部分具有6至20个碳原子,以6至15个为佳,R5可任意地被Cl、Br、OCH3或OC2H5取代,AO是氧乙烯基或氧丙烯基,m是0至100,X是O、NR4或CO-NR4,而A为CO、CO-CO、R6-CO、CO-R6-CO,或CO-NR4-R6-CO,其中的R4是C1-C4烷基,R6是亚烷基、亚烯基、亚芳基或亚烷基芳基,其亚烷基或亚烯基部分具有1至8个碳原子。此类漂白活化剂包括结构式为R3(AO)mOCOL的碳酸衍生物,结构式为R3OCO(CH2)2COL的琥珀酸衍生物,结构式为R3OCH2COL的乙醇酸衍生物,结构式为R3OCH2CH2COL的羟基丙酸衍生物,结构式为R3OCOCOL的草酸衍生物,结构式为R3OCOCH=CHCOL的马来酸和富马酸衍生物,结构式为R3CONR1(CH2)6COL的酰基氨基己酸衍生物,结构式为R3CONR1CH2COL的酰基甘氨酸衍生物和结构式为R3CONR1(CH2)4COL的氨基-6-羰基己酸衍生物。其中,m以0至10为佳,m是0时R3最好是C6-C12烷基,C6-C10更好,m不是0时R3最好是C9-C15烷基。离去基L的定义如上。
5)酰基氰脲酸盐,例如三乙酰基或三苯甲酰基氰脲酸盐,例如美国专利3,332,882中所述。
6)任意取代的苯甲酸酐或邻苯二甲酸酐,例如苯甲酸酐,间氯苯甲酸酐和邻苯二甲酸酐。
7)GB-A-855735所述的内酰胺类的N乙酰基化前体化合物,尤其是己内酰胺和戊内酰胺类,例如苯甲酰基戊内酰胺,苯甲酰基己内酰胺和它们的取代苯甲酰基类似物,例如氯、氨基、烷基、芳基和烷氧基衍生物。
所有上述化合物中,优选的是有机过酸前体1(c),4(a)和7。
如果存在,过氧酸漂白剂前体占组合物总重的约0.1%至10%,0.5%至5%更好,而且通常以漂白剂前体凝聚物的形式加入。
在此优选的漂白剂凝聚物通常含有按重量计约5%至约40%的粘合剂或凝聚剂,约10%至30%更好。合适的凝聚剂包括聚乙酰基吡咯烷酮,分子量为20,000至500,000的聚氧乙烯,分子量1000至50,000的聚乙二醇,分子量4000至20,000的Carbowax,非离子表面活性剂,脂肪酸,羧甲基纤维素钠,明胶,脂肪醇,磷酸盐,多磷酸盐,粘土,硅铝酸盐和聚多羧酸盐。其中,特别优选聚乙二醇,尤其是分子量约1,000至约30,000的,2000至约10,000更好。
从溶解性和pH特性考虑,优选的漂白剂前体凝聚物具有按重量计约10%至约75%,较好的是约20%至约60%过氧酸漂白剂前体,约5%至60%,约5%至约50%为佳,更好的是约10%至约40%碳酸(氢)盐/酸泡腾剂对,约0%至约20%过氧硼酸盐,和5%至约40%,较好的是约10%至约30%凝聚剂。最终的漂白剂前体粒宜具有约500至1500mm的平均颗粒直接,约500至1,000mm更好,这对最佳的溶解性和产品外观十分重要。而且,漂白剂前体凝聚物含量为组合物总重的约1%至约20%,约5%至15%更好。
本发明的漂白组合物其形式可以是膏体、片剂、粒状或粉末状的。片剂形式的组合物可以是单层或多层片剂。
本发明的漂白组合物中还可以补充以其它这类制剂中的常用组份,尤其是前文所述的表面活性剂、螯合剂、酶、染料、甜味剂、片剂粘合剂和填料、泡沫抑制剂(例如二甲基聚硅氧烷),脂肪酸糖酯之类的泡沫稳定剂,防腐剂,例如滑石粉、硬脂酸镁、无定形煅制二氧化硅的精细粉末之类的润滑剂。
在此适用的片剂粘合剂和填料包括聚乙烯吡咯烷酮,分子量20,000至500,000的聚氧乙烯,分子量约1000至约50,000的聚乙二醇,分子量约4000至20,000的Carbowax,非离子表面活性剂,脂肪酸,羧甲基纤维素钠,明胶,脂肪醇,粘土,多羧酸酯聚合物,碳酸钠,碳酸钙,氢氧化钙,氧化镁,碱式碳酸镁,硫酸钠,蛋白质,纤维素醚,纤维素酯,聚乙烯醇,藻酸酯,具有假胶体特性的植物脂肪。其中,特别好的是聚乙二醇,尤其是分子量约1,000至约30,000的,约12,000至约30,000更好。
螯合剂通过将钙、镁及重金属阳离子等金属离子保留在溶液中来帮助清洁和加强漂白剂的稳定性。合适的螯合剂的实例包括三聚磷酸钠,酸式磷酸钠,焦磷酸四钠,例如次氮基三乙酸和乙二胺四乙酸及其盐,乙二胺N,N-二琥珀酸(EDDS)及其盐之类的氨基多羧酸,例如羟基乙烷二膦酸、乙二胺四亚甲基膦酸、二亚乙基三胺五亚甲基膦酸及其盐之类的多膦酸盐和氨基多膦酸盐。螯合剂的选择并不十分重要,但必须在干燥以及水溶液状态下可与假牙清洁剂中的其它成分相配伍。较好的是,螯合剂占组合物总重的0.1%至60%,0.5%至30%更好。但是,膦酸螯合剂宜占组合物总重的约0.1%至1%,0.1%至0.5%更好。
在此适用的酶其实例包括蛋白酶,碱性酶(alkalase),淀粉酶,真菌及细菌裂解酶,葡聚糖酶,歧化酶(mutanase),葡聚糖酶,酯酶,纤维素酶,果胶酶,乳糖酶和过氧化物酶等。US-A-3,519,570和US-A-3,533,139中论述了合适的酶。
以下实施例进一步描述和说明了本发明范围内的优选实施方式。
实施例I至V
以下是根据本发明的,代表性的假牙清洁片剂。其中的百分数以片剂总重为基础。片剂通过将颗粒化的组份混合物在冲头和冲模压片机中,在约105kPa压力下压制而成。
I II III IV V
苹果酸 12 10 15 - 14
柠檬酸 - 10 - 15 -
碳酸钠 10 8 10 6 10
氨基磺酸 5 - - 3 3
PEG 20,000 - 3 7 8 5
PVP 40,000 6 3 - - -
碳酸氢钠 23 24 25 23 24
一水合过硼酸钠 15 12 16 30 15
单过硫酸钾 15 18 13 - 14
煅制二氧化硅 - 3 1 1 -
滑石粉 2 - - - -
EDTA - - 1 - 3
EDTMP1 1 - - 1 -
食用香精5 2 1 2 1 2
Abil EM904 1 1.5 0.5 2 1
漂白剂前体凝聚物 9 8 10 12 10
漂白剂前体凝聚物 I II III IV V
TAED2 2 - 4 5 2.5
TMHOS3 2 3 - - -
氨基磺酸 2 2 2 2 3.5
碳酸氢钠 0.5 0.2 0.2 0.5 2
PEG 6000 2.5 2 2.4 2.5 1.5
染料 - 0.8 1.4 2 0.5
1.乙二胺四亚甲基膦酸
2.四乙酰基乙二胺
3. 3,5,5-三甲基己酰氧基苯磺酸钠
4.十六烷基二甲聚硅氧烷共聚多元醇
5.以薄荷为基质的食用香精
在以上实施例I至V中,片剂总重为3g;直经为25mm。
实施例I至V的片剂表现出改善的消斑,清洁及抗菌活性,具有优良的粘结力和其它生理和实用操作特性。
实施例VI至IX
以下是本发明中代表性的日化香精、食用香精、清凉剂和抗微生物组合物。百分比按组合物的总重计。
VI VII VIII IX
PPG-5-ceteth-20 3.0 3.0 4.5 3.0
PEG-40氢化蓖麻油 - 1.8 4.5 3.0
Trideceth-12 2.0 - - -
Trideceth-19 - 2.0 - 3.0
食用香精5 2.0 3.0
日化香精6 - 3.0 - -
三甲基丁酰胺 0.3 0.5 - -
二氯苯氧氯酚 - - 1.0 0.5
Abil EM904 1.0 1.5 5.0 1.0
水 补足至100%
6.日化香精是主要用于气味效果的各成份的复杂混合物。
实施例V至IX的日化香精,食用香精,清凉剂和/或抗微生物剂组合物表现出改善的表面直接性、作用和/或效力。
Claims (7)
2.根据权利要求1所述的组合物,其中的二甲聚硅氧烷共聚多元醇选自C12至C20烷基二甲聚硅氧烷共聚多元醇及其混合物。
3.根据权利要求2所述的组合物,其中的二甲聚硅氧烷共聚多元醇是十六烷基二甲聚硅氧烷共聚多元醇。
4.根据权利要求1所述的组合物,它包含(按重量计)约0.01%至约25%二甲聚硅氧烷共聚多元醇。
5.根据权利要求1所述的组合物,它包含一种或一种以上食用香精组份,选自冬青油、牛至油(oregano oil)、桂叶油、薄荷油、留兰香油、丁子香油、鼠尾草油、黄樟油、柠檬油、橙油、茴香油、苯甲醛、苦杏仁油、樟脑、雪松叶油、甘牛至油、香茅油、熏衣草油、芥末油、松油、松针油、迷迭香油、百里香油、肉桂油及其混合物。
6.根据权利要求1所述的组合物,它包含一种或一种以上日化香精组份,选自乙酸香叶酯,乙酸里哪酯,香茅醇乙酸酯,乙酸二氢月桂烯酯,乙酸萜品酯,乙酸三环癸酯,丙酸三环癸酯,乙酸2-苯基乙酯,乙酸苄酯,水杨酸苄酯,苯甲酸苄酯,乙酸甲基苯基原酯,水杨酸戊酯,二氢茉莉酸甲酯,异丁酸苯氧基乙酯,橙花醇乙酸酯,乙酸三氯甲基-苯基甲酯,乙酸对叔丁基环己酯,乙酸异壬酯,乙酸柏木酯,乙酸韦惕蔚酯,苯醇,2-苯基乙醇,里哪醇,四氢里哪醇,香茅醇,二甲基苄基甲醇,二氢月桂烯醇,四氢月桂烯醇,萜品醇,丁子香酚,香叶醇,韦惕蔚醇,3-异莰基-环己醇,2-甲基-3-(对叔丁基苯基)-丙醇,2-甲基-3-(对异丙基苯基)-丙醇,3-(对叔丁基苯基)-丙醇,橙花醇,α-正戊基肉桂醛,α-己基肉桂醛,4-(4-羟基-4-甲基戊基)-3-环亚己基甲醛,4-(4-甲基-3-戊烯基)-3-环亚己基甲醛,4-乙酰氧-3-戊基-四氢吡喃,2-正庚基-环戊酮,3-甲基-2-戊基-环戊酮,正癸醛,正十二烷醛,羟基香茅醛,苯乙醛缩二甲醇,苯乙醛缩二乙醇,香叶腈,香茅腈,柏木基甲戊基-环戊酮,正癸醛,正十二烷基,羟基香茅醛,苯乙醛缩二甲醇,苯乙醛缩二乙醇,香叶腈,香茅腈,柏木基甲基醚,异长叶酮,茴香醛腈,茴香醛,天芥菜精,香豆素,香草醛,氧化二苯基,芷香酮,甲基芷香酮,异甲基芷香酮,甲基芷香酮,顺式-3-己醇及其酯,1,2-二氢化茚麝香,1,2,3,4-四氢化萘麝香,异苯并二氢呋喃麝香,大环酮,大环内酯麝香,十三烷二酸乙烯酯,芳香族硝基麝香,及其混合物。
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ATE371434T1 (de) * | 2003-03-27 | 2007-09-15 | Dow Corning | Zusammensetzungen mit verzögerter freisetzung |
GB0306995D0 (en) * | 2003-03-27 | 2003-04-30 | Dow Corning | Fragrance compositions |
EP1885275A4 (en) * | 2005-05-31 | 2012-04-18 | Takasago Internat Corp Usa | TOPICAL HEATING COMPOSITION |
JP2013529659A (ja) | 2010-07-08 | 2013-07-22 | ユニリーバー・ナームローゼ・ベンノートシヤープ | ヘアケア組成物 |
BR112013027310B8 (pt) | 2011-05-04 | 2018-08-14 | Unilever Nv | composição de xampu |
WO2012150259A1 (en) | 2011-05-04 | 2012-11-08 | Unilever Plc | Composition |
GB202100945D0 (en) * | 2021-01-25 | 2021-03-10 | Brightcure Ltd | A composition useful for treating bacterial infections |
CN113024818B (zh) * | 2021-03-01 | 2022-07-08 | 浙江润禾有机硅新材料有限公司 | 一种高纯度低副产的聚醚改性硅氧烷的制备方法 |
CN115612109B (zh) * | 2022-11-08 | 2023-08-08 | 江苏美思德化学股份有限公司 | 有机硅共聚物、其制备方法及其应用、软质泡沫稳定剂和软质聚氨酯泡沫 |
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US4725575A (en) * | 1986-12-10 | 1988-02-16 | Union Camp Corporation | Silicone rubber dispensers of volatile organic liquids |
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US3723491A (en) * | 1971-01-25 | 1973-03-27 | Goldschmidt Ag Th | Polysiloxane-polyalkyleneglycol block copolymers suitable as foam stabilizers in the manufacture of polyurethane foams |
US4157384A (en) * | 1972-01-28 | 1979-06-05 | Wilkinson Sword Limited | Compositions having a physiological cooling effect |
US4136250A (en) * | 1977-07-20 | 1979-01-23 | Ciba-Geigy Corporation | Polysiloxane hydrogels |
FR2693466B1 (fr) * | 1992-07-09 | 1994-09-16 | Oreal | Composition cosmétique sous forme d'émulsion triple eau/huile de silicone/eau gélifiée. |
DE59308338D1 (de) * | 1992-10-31 | 1998-05-07 | Goldschmidt Ag Th | Kosmetische oder pharmazeutische Zubereitungen |
FR2701845B1 (fr) * | 1993-02-23 | 1995-04-07 | Oreal | Emulsion eau-dans-huile à usage cosmétique ou pharmaceutique. |
JP3050601B2 (ja) * | 1993-02-26 | 2000-06-12 | エスティー ローダー インコーポレーテッド | 二酸化チタン分散液、化粧品組成物およびそれを使用する方法 |
FR2718022B1 (fr) * | 1994-04-01 | 1996-04-26 | Roussel Uclaf | Compositions cosmétiques ou dermatologiques et leur préparation. |
US5589177A (en) * | 1994-12-06 | 1996-12-31 | Helene Curtis, Inc. | Rinse-off water-in-oil-in-water compositions |
-
1994
- 1994-12-22 GB GBGB9425928.0A patent/GB9425928D0/en active Pending
-
1995
- 1995-12-13 WO PCT/US1995/016675 patent/WO1996019119A1/en active IP Right Grant
- 1995-12-13 PL PL95320863A patent/PL320863A1/xx unknown
- 1995-12-13 EP EP95943929A patent/EP0792110B1/en not_active Expired - Lifetime
- 1995-12-13 DK DK95943929T patent/DK0792110T3/da active
- 1995-12-13 MX MX9704666A patent/MX9704666A/es not_active IP Right Cessation
- 1995-12-13 CN CN95196845A patent/CN1090918C/zh not_active Expired - Fee Related
- 1995-12-13 AU AU45268/96A patent/AU688193B2/en not_active Ceased
- 1995-12-13 JP JP8519994A patent/JPH10512854A/ja active Pending
- 1995-12-13 KR KR1019970704211A patent/KR100225666B1/ko not_active IP Right Cessation
- 1995-12-13 DE DE69526798T patent/DE69526798T2/de not_active Expired - Lifetime
- 1995-12-13 AT AT95943929T patent/ATE217761T1/de active
- 1995-12-13 HU HU9800735A patent/HUT77710A/hu unknown
- 1995-12-13 ES ES95943929T patent/ES2173990T3/es not_active Expired - Lifetime
- 1995-12-13 CA CA002206463A patent/CA2206463C/en not_active Expired - Fee Related
- 1995-12-13 PT PT95943929T patent/PT792110E/pt unknown
- 1995-12-13 SK SK832-97A patent/SK83297A3/sk unknown
- 1995-12-13 BR BR9510477A patent/BR9510477A/pt not_active IP Right Cessation
- 1995-12-13 NZ NZ300505A patent/NZ300505A/xx not_active IP Right Cessation
- 1995-12-13 CZ CZ971909A patent/CZ190997A3/cs unknown
- 1995-12-22 TR TR95/01648A patent/TR199501648A2/xx unknown
Patent Citations (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US4725575A (en) * | 1986-12-10 | 1988-02-16 | Union Camp Corporation | Silicone rubber dispensers of volatile organic liquids |
Also Published As
Publication number | Publication date |
---|---|
ES2173990T3 (es) | 2002-11-01 |
CZ190997A3 (en) | 1997-11-12 |
ATE217761T1 (de) | 2002-06-15 |
AU4526896A (en) | 1996-07-10 |
AU688193B2 (en) | 1998-03-05 |
DK0792110T3 (da) | 2002-06-17 |
DE69526798D1 (de) | 2002-06-27 |
JPH10512854A (ja) | 1998-12-08 |
CA2206463A1 (en) | 1996-06-27 |
PT792110E (pt) | 2002-10-31 |
CN1170340A (zh) | 1998-01-14 |
EP0792110A1 (en) | 1997-09-03 |
MX9704666A (es) | 1997-09-30 |
WO1996019119A1 (en) | 1996-06-27 |
KR100225666B1 (ko) | 1999-10-15 |
EP0792110A4 (en) | 1998-04-01 |
DE69526798T2 (de) | 2003-02-06 |
TR199501648A2 (tr) | 1996-07-21 |
NZ300505A (en) | 1999-07-29 |
PL320863A1 (en) | 1997-11-10 |
SK83297A3 (en) | 1998-01-14 |
GB9425928D0 (en) | 1995-02-22 |
CA2206463C (en) | 2000-10-03 |
HUT77710A (hu) | 1998-07-28 |
EP0792110B1 (en) | 2002-05-22 |
BR9510477A (pt) | 1998-06-02 |
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