CN1606599A - 聚合物的制备方法 - Google Patents
聚合物的制备方法 Download PDFInfo
- Publication number
- CN1606599A CN1606599A CN02825696.4A CN02825696A CN1606599A CN 1606599 A CN1606599 A CN 1606599A CN 02825696 A CN02825696 A CN 02825696A CN 1606599 A CN1606599 A CN 1606599A
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- China
- Prior art keywords
- acid
- powder
- polymkeric substance
- ester
- ethanol
- Prior art date
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- 238000000034 method Methods 0.000 title claims abstract description 27
- 229920000642 polymer Polymers 0.000 title abstract description 9
- 239000000178 monomer Substances 0.000 claims abstract description 53
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 34
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- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 7
- 239000000843 powder Substances 0.000 claims description 157
- -1 alkane thiol Chemical class 0.000 claims description 153
- 239000000126 substance Substances 0.000 claims description 94
- 239000000203 mixture Substances 0.000 claims description 83
- 239000002253 acid Substances 0.000 claims description 41
- 229910052799 carbon Inorganic materials 0.000 claims description 39
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- 150000001721 carbon Chemical group 0.000 claims description 32
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 claims description 23
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 20
- 238000009472 formulation Methods 0.000 claims description 20
- ISXSCDLOGDJUNJ-UHFFFAOYSA-N tert-butyl prop-2-enoate Chemical compound CC(C)(C)OC(=O)C=C ISXSCDLOGDJUNJ-UHFFFAOYSA-N 0.000 claims description 13
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- 125000001931 aliphatic group Chemical group 0.000 claims description 6
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- 125000000217 alkyl group Chemical group 0.000 description 20
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- BGHCVCJVXZWKCC-UHFFFAOYSA-N tetradecane Chemical compound CCCCCCCCCCCCCC BGHCVCJVXZWKCC-UHFFFAOYSA-N 0.000 description 18
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- 229920002554 vinyl polymer Polymers 0.000 description 10
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- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000047 product Substances 0.000 description 9
- GLZPCOQZEFWAFX-UHFFFAOYSA-N Geraniol Chemical compound CC(C)=CCCC(C)=CCO GLZPCOQZEFWAFX-UHFFFAOYSA-N 0.000 description 8
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- 239000000243 solution Substances 0.000 description 8
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- 239000012153 distilled water Substances 0.000 description 7
- 239000003995 emulsifying agent Substances 0.000 description 7
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- 230000035807 sensation Effects 0.000 description 7
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- OSSNTDFYBPYIEC-UHFFFAOYSA-N 1-ethenylimidazole Chemical compound C=CN1C=CN=C1 OSSNTDFYBPYIEC-UHFFFAOYSA-N 0.000 description 6
- 239000004471 Glycine Substances 0.000 description 6
- 229920002472 Starch Polymers 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- 239000007864 aqueous solution Substances 0.000 description 6
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- 229930195733 hydrocarbon Natural products 0.000 description 6
- 150000002430 hydrocarbons Chemical class 0.000 description 6
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 6
- 239000003999 initiator Substances 0.000 description 6
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- 150000003254 radicals Chemical class 0.000 description 6
- 239000008107 starch Substances 0.000 description 6
- 235000019698 starch Nutrition 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid group Chemical group S(O)(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- ZEMPKEQAKRGZGQ-AAKVHIHISA-N 2,3-bis[[(z)-12-hydroxyoctadec-9-enoyl]oxy]propyl (z)-12-hydroxyoctadec-9-enoate Chemical compound CCCCCCC(O)C\C=C/CCCCCCCC(=O)OCC(OC(=O)CCCCCCC\C=C/CC(O)CCCCCC)COC(=O)CCCCCCC\C=C/CC(O)CCCCCC ZEMPKEQAKRGZGQ-AAKVHIHISA-N 0.000 description 5
- WROUWQQRXUBECT-UHFFFAOYSA-N 2-ethylacrylic acid Chemical compound CCC(=C)C(O)=O WROUWQQRXUBECT-UHFFFAOYSA-N 0.000 description 5
- OSCJHTSDLYVCQC-UHFFFAOYSA-N 2-ethylhexyl 4-[[4-[4-(tert-butylcarbamoyl)anilino]-6-[4-(2-ethylhexoxycarbonyl)anilino]-1,3,5-triazin-2-yl]amino]benzoate Chemical compound C1=CC(C(=O)OCC(CC)CCCC)=CC=C1NC1=NC(NC=2C=CC(=CC=2)C(=O)NC(C)(C)C)=NC(NC=2C=CC(=CC=2)C(=O)OCC(CC)CCCC)=N1 OSCJHTSDLYVCQC-UHFFFAOYSA-N 0.000 description 5
- ZKYCLDTVJCJYIB-UHFFFAOYSA-N 2-methylidenedecanamide Chemical compound CCCCCCCCC(=C)C(N)=O ZKYCLDTVJCJYIB-UHFFFAOYSA-N 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical compound [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 5
- 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 5
- SNPLKNRPJHDVJA-ZETCQYMHSA-N D-panthenol Chemical compound OCC(C)(C)[C@@H](O)C(=O)NCCCO SNPLKNRPJHDVJA-ZETCQYMHSA-N 0.000 description 5
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 5
- 239000004166 Lanolin Substances 0.000 description 5
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- LDHQCZJRKDOVOX-NSCUHMNNSA-N crotonic acid Chemical compound C\C=C\C(O)=O LDHQCZJRKDOVOX-NSCUHMNNSA-N 0.000 description 5
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 5
- 239000006260 foam Substances 0.000 description 5
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 5
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 5
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- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 4
- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 4
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Classifications
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- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
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- A61K8/894—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a polyoxyalkylene group, e.g. cetyl dimethicone copolyol
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- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
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- A—HUMAN NECESSITIES
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- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/06—Preparations for styling the hair, e.g. by temporary shaping or colouring
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/06—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polyethers, polyoxymethylenes or polyacetals
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
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Abstract
本发明涉及一种通过使(a)烯属不饱和单体和(b)含聚氧化烯的聚硅氧烷衍生物进行自由基聚合而制备聚合物的方法,包括在碳链长度为C13-C22的链烷硫醇存在下进行该聚合。
Description
具有成膜性能的聚合物用于化妆品制剂,并尤其适合作为用于皮肤和头发的化妆品的添加剂。
在用于皮肤的化妆品制剂中,聚合物可开发出特定作用。聚合物尤其可贡献于皮肤保湿和调节皮肤并改善皮肤的感觉。皮肤变得越来越光滑和越来越柔软。
在用于头发的化妆品制剂中,聚合物用于定形,改善结构和使头发成形。它们增加相容性并改善头发的感觉。这些头发处理组合物一般包含成膜剂在醇或醇与水的混合物中的溶液。
对头发处理组合物的一个要求是尤其赋于头发以光泽、柔顺性和自然的令人愉快的感觉。
已知的是使用乙烯基内酰胺均聚和共聚物或含羧酸酯基的聚合物。性能如在高大气湿度中的强附着、弹性、从头发中洗出的能力和与其它配方组分的相容性的所需分布通过将疏水性、具有弹性和含有羧基的单体共聚而实现。
然而,用这些聚合物定形的发式的感觉令人不愉快地刺眼和不自然。尽管添加软化剂能改善这类发式的感觉,但这也降低定形作用。
经常使用聚硅氧烷,尽管这些聚合物与极性聚合物不相容并且常常需要其它添加剂以使它们能配制。分层可能既在配制剂的储存过程中又在使用过程中导致问题。
为了防止分层,因此不乏将聚硅氧烷基与聚合物共价键接的尝试。EP-A 408 311描述了碳主链上键接有聚二甲基硅氧烷侧链的接枝共聚物。但仅仅描述了使用携带聚硅氧烷链的不饱和单体制备的聚合物。
EP-A 670 342描述了烷氧基化的聚硅氧烷在头发护理组合物中的用途。但并未公开不饱和化合物的聚合物在头发护理组合物中的用途。尽管将烷氧基化的聚硅氧烷用作市购头发定形聚合物的添加剂改善了其感觉,但它也导致降低的定形作用。
欧洲专利EP-A 412 704和EP-A 412 707描述了呈摩尔质量为1000-50,000的与常规疏水和亲水单体聚合的大单体形式的聚硅氧烷基团。这些单体的合成极其复杂。由于它们的分子量高,因此基本上不可能将未反应的大单体及其非反应性杂质从聚合物中分离出来。这些代表了毒性和过敏危险。而且,如上述专利所教导,所得共聚物为了获得良好作用必须经常仅以与其它聚合物、载体和其它助剂的组合来配制。
DE 42 40 108描述了含有聚硅氧烷的基料,这类基料适于作为防污涂料,尤其作为防涂写涂料。这些基料然而与油漆类似,不适用于化妆品用途。
WO 99/04750描述了可通过在含有聚氧化烯的聚硅氧烷衍生物存在下自由基聚合烯属不饱和单体而获得的聚合物。
WO 99/04750描述了利用添加硫代乙醇酸乙基己酯来制备聚合物(实施例15-20)。
可根据WO 99/04750获得的聚合物的缺点主要在于它们的强烈固有气味,该气味经常在化妆品组合物的进一步储存和/或配制时增加。这导致仅能有限使用已知产品。在化妆品配制剂中,曾经尝试使用芳香油来除去这些聚合物的该固有气味。除了彻底除去该固有气味不总是可行的事实以外,芳香油的使用在各种条件下导致不希望的过敏反应。这限制了已知聚合物在化妆品组合物中的使用。此外,这些聚合物本身应该与现有技术的产品相比不那么刺激,因此适用于抗过敏化妆品制剂。
本发明的目的是提供这样一种方法,其中获得的聚合物由于其中性气味而适于广泛使用,尤其是用于化妆品组合物以及还尤其适于不添加芳香油的配制剂。关于此,特别感兴趣的是这些聚合物甚至在储存之后也不会在化妆品制剂中产生固有气味。另外,还需要诸如从头发中洗出的能力、与其它化妆品成分的相容性,尤其是在无水制剂中的溶解性、感觉和经处理头发的定型之类的性能。提供与现有技术的产品相比不那么刺激的聚合物也是希望的。本发明的另一个目的是提供可以粉末形式使用并因此尤其适于特定装饰性化妆品制剂的聚合物。
我们发现上述目的通过这样一种方法得以实现,其中使
(a)烯属不饱和单体和
(b)含聚氧化烯的聚硅氧烷衍生物
通过在碳链长度为C13-C22的链烷硫醇存在下自由基聚合而反应。
我们发现上述目的通过这样一种方法得以实现,其中使
(a)烯属不饱和单体和
(b)含聚氧化烯的聚硅氧烷衍生物
i)通过在碳链长度为C10-C22的链烷硫醇存在下自由基聚合,然后
ii)用过氧化氢处理而进行。
与现有技术的产品相反,尤其是与根据WO 99/04750的聚合物相反,可以此方式获得的聚合物的特征在于无气味并且甚至当无论以单独物质或还是以在化妆品制剂中储存时都不会产生气味。同时,可以此方式获得的聚合物显示出良好的成膜性能和良好的与常规化妆品成分的相容性。
所用的链烷硫醇是碳链长度为C10-C22的线性和支化链烷硫醇。特别优选线性链烷硫醇,还优选碳链长度为C13-C22,尤其是C14-C18的链烷硫醇。可提及的链烷硫醇是正癸硫醇、正十二烷硫醇、叔十二烷硫醇、正十四烷硫醇、正十五烷硫醇、正十六烷硫醇、正十七烷硫醇、正十八烷硫醇、正十九烷硫醇、正二十烷硫醇、正二十二烷硫醇。特别优选线性偶数链烷硫醇。
链烷硫醇还可以作为混合物使用。
链烷硫醇的用量基于待聚合单体计通常为0.1-5重量%,尤其是0.25-2重量%。链烷硫醇通常与单体一起加入聚合中。
若使用碳链长度为C10-C12的链烷硫醇,则需要随后的过氧化氢处理,以得到具有中性气味的聚合物。对于在聚合之后的过氧化氢处理,基于待聚合单体计通常使用0.01-2.0重量%,尤其是0.02-1.0重量%,特别优选0.03-0.15重量%的过氧化氢。已证实特别有利的是在20-100℃,尤其是30-80℃下进行该过氧化氢处理。该过氧化氢处理通常进行30-240分钟,尤其是45-90分钟。
若使用碳链长度为C13-C22的链烷硫醇,则可免去过氧化氢处理。然而在本发明的进一步实施方案中,也可在添加碳链长度为C13-C22的链烷硫醇的情况下涉及过氧化氢处理。
在本发明方法的优选实施方案中,将这些聚合物转化成粉末形式。为此,所有本领域熟练技术人员已知的方法都适合,例如喷雾干燥、冻干和流化床干燥。
特别优选喷雾干燥。
合适的可聚合单体(a)是烯属不饱和单体。关于此,可使用单独单体或两种或更多种单体的组合。
优选可通过由自由基引发的反应聚合的单体。术语“烯属不饱和单体”是指具有至少一个可被单-、二-、三-或四取代的可聚合碳-碳双键的单体。
烯属不饱和单体(a)可用下式表示:
X-C(O)CR7=CHR6其中X选自基团-OH、-OM、-OR8、NH2、-NHR8、N(R8)2;M是选自Na+、K+、Mg++、Ca++、Zn++、NH4 +、烷基铵、二烷基铵、三烷基铵和四烷基铵的阳离子;基团R8可相同或不同且选自-H、C1-C40线性或支化链的烷基、N,N-二甲基氨基乙基、2-羟基乙基、2-甲氧基乙基、2-乙氧基乙基、羟基丙基、甲氧基丙基或乙氧基丙基;R7和R6相互独立地选自-H、C1-C8线性或支化链的烷基链、甲氧基、乙氧基、2-羟基乙氧基、2-甲氧基乙氧基和2-乙氧基乙基。
合适的单体(a)的代表性但非限制性实例例如是丙烯酸及其盐、酯和酰胺。该盐可衍生自任何无毒的金属、铵或取代的铵抗衡离子。
该酯可衍生自C1-C40线性链、C3-C40支化链或C3-C40碳环醇,衍生自具有2至约8个羟基的多官能醇,例如乙二醇、己二醇、甘油和1,2,6-己三醇,衍生自氨基醇或衍生自醇醚,如甲氧基乙醇和乙氧基乙醇或聚乙二醇。
还合适的是下式(II)的丙烯酸和甲基丙烯酸的N,N-二烷基氨基烷酯和N-二烷基氨基烷基丙烯酰胺和甲基丙烯酰胺:
其中R9=H、具有1-8个碳原子的烷基,R10=H、甲基,R11=具有1-24个碳原子的亚烷基,其任选被烷基取代,R12、R13=C1-C40烷基,Z=氮,此时x=1,或者为氧,此时x=0。
该酰胺可以是未取代的、N-烷基或N-烷基氨基单取代的,或者N,N-二烷基-取代的或N,N-二烷基氨基二取代的,其中烷基或烷基氨基衍生自C1-C40线性链、C3-C40支化链或C3-C40碳环单元。另外,该烷基氨基还可以是季铵化的。
优选的式II单体是(甲基)丙烯酸N,N-二甲基氨基甲酯、(甲基)丙烯酸N,N-二乙基氨基甲酯、(甲基)丙烯酸N,N-二甲基氨基乙酯、(甲基)丙烯酸N,N-二乙基氨基乙酯。
同样还可使用的单体(a)是取代的丙烯酸及其盐、酯和酰胺,其中个碳原子上的取代基位于丙烯酸的二或三位上,并且相互独立地选自C1-C4-烷基、-CN、COOH,特别优选甲基丙烯酸、乙基丙烯酸和3-氰基丙烯酸。这些取代的丙烯酸的这些盐、酯和酰胺可按上述对丙烯酸的盐、酯和酰胺所述选择。
其它合适的单体(a)是C1-C40线性链、C3-C40支化链或C3-C40碳环羧酸的乙烯基和烯丙酯(例如:乙酸乙烯酯、丙酸乙烯酯、新壬酸乙烯酯、新十一烷酸乙烯酯或叔丁基苯甲酸乙烯酯);乙烯基或烯丙基卤,优选乙烯基氯和烯丙基氯;乙烯基醚,优选甲基、乙基、丁基或十二烷基乙烯基醚,乙烯基甲酰胺,乙烯基甲基乙酰胺,乙烯基胺;乙烯基内酰胺,优选乙烯基吡咯烷酮和乙烯基己内酰胺;乙烯基-或烯丙基-取代的杂环化合物,优选乙烯基吡啶,乙烯基噁唑啉和烯丙基吡啶。
还合适的是式III的N-乙烯基咪唑,其中R14-R16相互独立地为氢、C1-C4-烷基或苯基:
还合适的单体(a)是式(IV)的二烯丙基胺:
其中R17=C1-C24烷基。
其它合适的单体(a)是偏二氯乙烯;和具有至少一个碳-碳双键的烃,优选苯乙烯、α-甲基苯乙烯、叔丁基苯乙烯、丁二烯、异戊二烯、环己二烯、乙烯、丙烯、1-丁烯、2-丁烯、异丁烯、乙烯基甲苯以及这些单体的混合物。
特别合适的单体(a)是丙烯酸、甲基丙烯酸、乙基丙烯酸、丙烯酸甲酯、丙烯酸乙酯、丙烯酸丙酯、丙烯酸正丁酯、丙烯酸异丁酯、丙烯酸叔丁酯、丙烯酸2-乙基己酯、丙烯酸癸酯、甲基丙烯酸甲酯、甲基丙烯酸乙酯、甲基丙烯酸丙酯、甲基丙烯酸正丁酯、甲基丙烯酸异丁酯、甲基丙烯酸叔丁酯、甲基丙烯酸2-乙基己酯、甲基丙烯酸癸酯、乙基丙烯酸甲酯、乙基丙烯酸乙酯、乙基丙烯酸正丁酯、乙基丙烯酸异丁酯、乙基丙烯酸叔丁酯、乙基丙烯酸2-乙基己酯、乙基丙烯酸癸酯、丙烯酸2,3-二羟基丙酯、甲基丙烯酸2,3-二羟基丙酯、丙烯酸2-羟基乙酯、丙烯酸羟基丙酯、甲基丙烯酸2-羟基乙酯、乙基丙烯酸2-羟基乙酯、丙烯酸2-甲氧基乙酯、甲基丙烯酸2-甲氧基乙酯、乙基丙烯酸2-甲氧基乙酯、甲基丙烯酸2-乙氧基乙酯、乙基丙烯酸2-乙氧基乙酯、甲基丙烯酸羟基丙酯、甘油单丙烯酸酯、甘油单甲基丙烯酸酯、聚乙二醇(甲基)丙烯酸酯、不饱和磺酸,例如丙烯酰氨基丙磺酸;
丙烯酰胺、甲基丙烯酰胺、乙基丙烯酰胺、N-甲基丙烯酰胺、N,N-二甲基丙烯酰胺、N-乙基丙烯酰胺、N-异丙基丙烯酰胺、N-丁基丙烯酰胺、N-叔丁基丙烯酰胺、N-辛基丙烯酰胺、N-叔辛基丙烯酰胺、N-十八烷基丙烯酰胺、N-苯基丙烯酰胺、N-甲基甲基丙烯酰胺、N-乙基甲基丙烯酰胺、N-十二烷基甲基丙烯酰胺、1-乙烯基咪唑、1-乙烯基-2-甲基咪唑、(甲基)丙烯酸N,N-二甲基氨基甲酯、(甲基)丙烯酸N,N-二乙基氨基甲酯、(甲基)丙烯酸N,N-二甲基氨基乙酯、(甲基)丙烯酸N,N-二乙基氨基乙酯、(甲基)丙烯酸N,N-二甲基氨基丁酯、(甲基)丙烯酸N,N-二乙基氨基丁酯、(甲基)丙烯酸N,N-二甲基氨基己酯、(甲基)丙烯酸N,N-二甲基氨基辛酯、(甲基)丙烯酸N,N-二甲基氨基十二烷酯、N-[3-(二甲基氨基)丙基]甲基丙烯酰胺、N-[3-(二甲基氨基)丙基]丙烯酰胺、N-[3-(二甲基氨基)丁基]甲基丙烯酰胺、N-[8-(二甲基氨基)辛基]甲基丙烯酰胺、N-[12-(二甲基氨基)十二烷基]甲基丙烯酰胺、N-[3-(二乙基氨基)丙基]甲基丙烯酰胺、N-[3-(二乙基氨基)丙基]丙烯酰胺;
马来酸、富马酸、马来酸酐及其单酯、巴豆酸、衣康酸、二烯丙基二甲基氯化铵、乙烯基醚(例如:甲基、乙基、丁基或十二烷基乙烯基醚)、乙烯基甲酰胺、乙烯基甲基乙酰胺、乙烯基胺;甲基·乙烯基酮、马来酰亚胺、乙烯基吡啶、乙烯基咪唑、乙烯基呋喃、苯乙烯、磺酸苯乙烯酯、烯丙基醇及其混合物;
当中特别优选丙烯酸、甲基丙烯酸、马来酸、富马酸、巴豆酸、马来酸酐及其单酯、丙烯酸甲酯、甲基丙烯酸甲酯、丙烯酸乙酯、甲基丙烯酸乙酯、丙烯酸正丁酯、甲基丙烯酸正丁酯、丙烯酸叔丁酯、甲基丙烯酸叔丁酯、丙烯酸异丁酯、甲基丙烯酸异丁酯、丙烯酸2-乙基己基、N-叔丁基丙烯酰胺、N-辛基丙烯酰胺、丙烯酸2-羟基乙酯、丙烯酸羟基丙酯、甲基丙烯酸2-羟基乙酯、甲基丙烯酸羟基丙酯、(甲基)丙烯酸亚烷基二醇酯、不饱和磺酸例如丙烯酰氨基丙磺酸、乙烯基吡咯烷酮、乙烯基己内酰胺、乙烯基醚(例如:甲基、乙基、丁基或十二烷基乙烯基醚)、乙烯基甲酰胺、乙烯基甲基乙酰胺、乙烯基胺、1-乙烯基咪唑、1-乙烯基-2-甲基咪唑、甲基丙烯酸N,N-二甲基氨基甲酯和N-[3-(二甲基氨基)丙基]甲基丙烯酰胺;用甲基氯、硫酸甲酯或硫酸二乙酯季铵化的3-甲基-1-乙烯基氯化咪唑鎓、3-甲基-1-乙烯基甲基硫酸咪唑鎓、甲基丙烯酸N,N-二甲基氨基乙酯、N-[3-(二甲基氨基)丙基]甲基丙烯酰胺。
在非常特别优选的实施方案中,所用单体(a)是丙烯酸叔丁酯(=a1)和甲基丙烯酸(=a2)。
具有碱性氮原子的单体可以以下列方式季铵化:
适于将胺季铵化的试剂的实例是在烷基中具有1-24个碳原子的烷基卤,例如甲基氯、甲基溴、甲基碘、乙基氯、乙基溴、丙基氯、己基氯、十二烷基氯、月桂基氯和苄基卤,尤其是苄基氯和苄基溴。其它合适的季铵化试剂是硫酸二烷酯,尤其是硫酸二甲酯或硫酸二乙酯。碱性胺的季铵化还可用氧化烯如氧化乙烯或氧化丙烯在酸存在下进行。优选的季铵化试剂是:甲基氯、硫酸二甲酯或硫酸二乙酯。
在优选实施方案中,所用单体(a)是(甲基)丙烯酸酯。
季铵化可在聚合之前或之后进行。
此外,还可使用不饱和酸例如丙烯酸或甲基丙烯酸与式(V)的季铵化表氯醇(R18=C1-C40烷基)的反应产物。
其实例是(甲基)丙烯酰氧基羟基丙基三甲基氯化铵和(甲基)丙烯酰氧基羟基丙基三乙基氯化铵。
碱性单体还可通过将其用无机酸如硫酸、氢氯酸、氢溴酸、氢碘酸、磷酸或硝酸,或者用有机酸如甲酸、乙酸、乳酸或柠檬酸中和而阳离子化。
除上述单体外,还可将“大单体”如含聚硅氧烷和一个或多个可自由基聚合基团的大单体,或者烷基噁唑啉大单体用作单体(a),如EP 408 311所述。
此外,还可组合或单独使用含氟单体,如EP 558 423所述,或者使用具有交联作用或调节分子量的化合物。
可使用的调节剂是本领域熟练技术人员已知的常规化合物,例如硫化合物(例如:巯基乙醇、硫代乙醇酸2-乙基己酯、硫代乙酸或十二烷基硫醇)和三溴一氯甲烷或其它对所得聚合物的分子量具有调节效果的化合物。适当的话,还可使用含硫醇基团的聚硅氧烷化合物,优选使用不含聚硅氧烷的调节剂。
可使用的交联单体是具有至少两个烯属不饱和双键的化合物,例如烯属不饱和羧酸如丙烯酸或甲基丙烯酸和多元醇的酯,至少二元醇的醚,例如乙烯基醚或烯丙基醚。还合适的是具有至少两个双键的直链或支化的、线性或环状、脂族或芳族烃,当是脂族烃时不必共轭。还合适的是丙烯酸和甲基丙烯酸的酰胺,以及至少二官能胺例如1,2-二氨基乙烷、1,3-二氨基丙烷的N-烯丙基胺。还合适的是三烯丙基胺或相应的铵盐,脲衍生物的N-乙烯基化合物,至少二官能的酰胺、异氰脲酸酯或氨基甲酸乙酯。其它合适的交联剂是二乙烯基二氧六环、四烯丙基硅烷或四乙烯基硅烷。
特别优选的交联剂例如是亚甲基双丙烯酰胺、三烯丙基胺和三烯丙基铵盐、二乙烯基咪唑、N,N’-二乙烯基亚乙基脲、多元醇与丙烯酸或甲基丙烯酸的反应产物以及聚氧化烯或已与氧化乙烯和/或氧化丙烯和/或表氯醇反应的多元醇的甲基丙烯酸酯和丙烯酸酯。
本发明的单体(a)当含有可离子化的基团时可在聚合之前或之后用酸或碱部分或全部中和,以例如将在水中的溶解度或分散度调节至所需水平。
可用于携带酸基团的单体中和剂例如是无机碱如碳酸钠、碱金属氢氧化物和氨,有机碱如氨基醇,尤其是2-氨基-2-甲基-1-丙醇、单乙醇胺、二乙醇胺、三乙醇胺、三异丙醇胺、三[(2-羟基)-1-丙基]胺、2-氨基-2-甲基-1,3-丙二醇、2-氨基-2-羟基甲基-1,3-丙二醇和二胺类,如赖氨酸。
可用于携带可阳离子化基团的单体的中和剂例如是无机酸,如盐酸、硫酸或磷酸,以及还有有机酸,如羧酸、乳酸、柠檬酸或其它物质。
特别合适的含聚氧化烯的聚硅氧烷衍生物(b)是含有如下结构元素的那些:
R6是具有1-40个碳原子的有机基团,其可含有氨基、羧酸基团或磺酸酯基,并且当c=0时,还是无机酸的阴离子,以及其中基团R1可相同或不同,来自具有1-20个碳原子的脂族烃、具有3-20个碳原子的环状脂族烃,具有芳香性或者与R5相同,其中:
条件是R1、R2或R3至少之一是根据上述定义的含聚氧化烯的基团,n是1-6的整数,x和y是使得聚硅氧烷嵌段的分子量为300-30,000的整数,a、b可以是0-50的整数,条件是a和b之和大于0,以及c为0或1。
优选的基团R2和R5是其中a+b为5-30的那些。
基团R1优先选自:甲基、乙基、丙基、丁基、异丁基、戊基、异戊基、己基、辛基、癸基、十二烷基和十八烷基,脂环族基团,尤其是环己基,芳族基团,尤其是苯基或萘基,混合的芳族-脂族基团,如苄基或苯基乙基,以及甲苯基和二甲苯基和R5。
特别合适的基团R4是R4=-(CO)cR6,其中R6是具有1-40个碳原子且可携带其它离子基团如NH2、COOH、SO3H的任何所需烷基、环烷基或芳基。
优选的无机基团R6当c=0时是磷酸根和硫酸根。
在本发明的特别优选实施方案中,所用的含聚氧化烯的聚硅氧烷衍生物(b)是根据下式的化合物:
其中R1=-CH3
R4=-H、-COCH3、C1-C4烷基n=1-6,尤其是2-4,优选3,x和y是使得聚硅氧烷嵌段的分子量为1000-10,000的整数,a、b可以是0-50的整数,条件是a和b之和大于0。
这类特别优选的聚硅氧烷衍生物以CAS No.872 44-72-2已知。商业产品可以商品名Belsil DMC6031TM(Wacker)、Dabco DC193、Dabco DC5357、Dow Corning 198TM、Dow Corning 5039TM和Silwet 7600TM(Witco)获得。
这类特别优选的聚硅氧烷衍生物以CAS No.71965-38-3已知。商业产品可以商品名Abil B 8842、Abil B 8843、Silwet L 7607(Witco)获得。
还特别优选可以以商品名Belsil DMC6032TM(Wacker)和DowCorning 190TM(Dow Chemicals)获得的那些聚硅氧烷衍生物。
本发明的含聚硅氧烷的聚合物的单体(a)可占50-99.9重量%,优选70-99重量%,特别优选85-98重量%,若烯属不饱和单体(a)以两种单体(a1和a2)的组合使用,则证实有利的是使用49.5-99重量%(a1)和0.5-40重量%(a2)。
聚硅氧烷衍生物(b)在本发明聚合物中的存在量通常为0.1-50重量%,优选0.5-20重量%,特别优选2-15重量%。
在特别优选的实施方案中,所用单体混合物包含:
(a1)49.5-99重量%(甲基)丙烯酸酯,尤其是丙烯酸叔丁酯
(a2)0.5-40重量%另一(甲基)丙烯酸酯,尤其是甲基丙烯酸
(b)0.5-20重量%根据下式的含聚氧化烯的聚硅氧烷衍生物:
其中R1=-CH3
R4=-H、-COCH3、C1-C4烷基,n=1-6,尤其是2-4,优选3,x和y是使得聚硅氧烷嵌段的分子量为1000-10,000的整数,a、b可以是0-50的整数,条件是a和b之和大于0。
若聚硅氧烷化合物(b)在聚合中不存在,而是在聚合之后混入其中,则通常得到非常柔软的粘性膜,这些膜不适于根据本发明在皮肤和头发用化妆品中的应用。
这表明在聚合过程中可能导致聚合物接枝到聚硅氧烷化合物上并且这贡献良好的膜性能,如不发粘、高表面光滑度和硬度,以及还有改进的抗粘连性。然而,还可设想不同于本发明聚合物获得其有利性能的接枝的机理。
术语“可聚合”指所用单体可使用任何常规合成方法聚合。
例如,这可以是溶液聚合、乳液聚合、反乳液聚合、悬浮聚合、反悬浮聚合或沉淀聚合,但可使用的方法不限于此。对于溶液聚合,可将水、常规有机溶剂或根据本发明的聚硅氧烷衍生物本身或所述溶剂的混合物用作溶剂。
优选本发明聚合物的K值(根据Fickentscher,Cellulosechemie(纤维素化学),第13卷,第58-64卷(1932)在25℃下在1重量%乙醇溶液中测定)为30-50,优选37-41。
特别合适的聚合物是可溶于水中的那些或其在水中的分散性大得使它们可以以大于0.1g/l、优选大于0.2g/l的量溶于水∶乙醇=20∶80(体积%∶体积%)溶剂混合物中的那些。
对本发明而言,“水可分散的”聚合物是指当与水接触时在24小时内形成用眼睛而不是用光学设备检测不到任何固体颗粒的流体的聚合物。为了检测聚合物是否可分散于水中,将100mg呈100μm厚的膜形式的聚合物加入100ml水(20℃)中,并在市购振荡工作台上振荡24小时。若在振荡之后观察不到固体颗粒但流体混浊,则该聚合物可分散于水中;若不混浊,则该聚合物可溶于水中。
在单体的聚合过程中,任选还可存在其它聚合物,例如烯属不饱和单体的均聚-和共聚物,以及还有聚酰胺、聚氨酯或聚酯。该聚酰胺、聚氨酯或聚酯优选例如用羧酸酯基或磺酸酯基进行离子改性。
聚合物经常使用引发剂如过氧或偶氮化合物来制备,例如过氧化二苯甲酰、过新戊酸叔丁酯、过-2-乙基己酸叔丁酯、过氧化二叔丁基、氢过氧化叔丁基、过氧化2,5-二甲基-2,5-二(叔)丁基(己烷)、碱金属或铵过硫酸盐、偶氮二异丁腈、2,2’-偶氮二(2-甲基丁腈)、2,2’-偶氮二(2,4-二甲基戊腈)、1,1’-偶氮二(1-环己烷甲腈)、2,2’-偶氮二(2-脒基丙烷)盐、4,4’-偶氮二(4-氰基戊酸)或2-(氨基甲酰基偶氮)异丁腈等,过氧化氢或氧化还原引发剂。引发剂的用量基于待聚合单体计通常不超过10重量%,优选0.02-5重量%。
乳液聚合通常在排除氧气的情况下于20-200℃下进行。该聚合可间歇或连续进行。
该程序优选涉及在聚合过程中均匀地将至少部分单体、引发剂和链烷硫醇计量加入反应容器中。然而还可将该单体、链烷硫醇和引发剂在开始的时候引入反应器中并聚合,在有些情况下有必要进行冷却。
当聚合结束时,可通过以已知方式通过添加合适的引发剂而后聚合来降低残余单体含量。需要的话,还可以常规方式例如通过引入蒸汽而进行物理祛臭。
每种情况下需要的K值可以本身已知的方式通过选择聚合条件,例如聚合温度和引发剂浓度来建立。在有些情况下,特别当使用乳液和悬浮聚合时,使用调节剂,尤其是硫化合物如巯基乙醇、硫代乙醇酸2-乙基己酯、硫代乙醇酸或十二烷基硫醇可能对于降低K值是适当的。该K值根据Fikentscher,Cellulosechemie,第13卷,第58-64页(1932)于25℃下以1重量%浓度的乙醇溶液测定,并代表分子量的量度。
若聚合物通过乳液聚合制备,则所得分散体可以直接引入含水、含水-醇或含醇化妆品制剂中,例如头发定型制剂中,或者将分散体例如喷雾干燥,使得该聚合物可以作为粉末使用和加工。
本发明进一步提供可通过如实施例1-13所述的方法获得的聚合物。
可以此方式获得的聚合物的特征是低气味、低过敏潜力,以及还有良好的头发化妆品性能。
本发明进一步提供尤其呈粉末形式的本发明聚合物在化妆品制剂,尤其是在头发化妆品制剂中的用途。
本发明聚合物特别优选用于头发化妆品制剂中。可提及的头发化妆品制剂是头发卷曲剂、发用液剂、护发素、发用乳剂、开叉端用流体、长效卷发剂用中和剂、热油处理剂、调理剂、卷曲松散剂、卷曲定型液、发型固定液、洗发剂、发用蜡、润发脂、发用泡沫、染发剂或喷发胶。特别优选丙烯酸酯聚合物在呈喷射制剂和/或头发泡沫形式的发式定型组合物中的用途。
本发明聚合物在头发化妆品制剂中的特征是与喷雾制剂中的非极性推进剂,尤其是与烃类如正丙烷、异丙烷、正丁烷、异丁烷、正戊烷及其混合物具有高相容性。它们具有良好的头发定型作用,并且特征在于它们基本上不导致头发粘在一起。
除了无气味外,聚合物还对头发化妆品制剂中的性能具有优异结果。它们溶解在醇类如乙醇或异丙醇以及这些醇与水的混合物中,形成透明液体。当该溶液与推进剂如二甲基醚一起用于标准喷雾配制剂中时也获得该溶液的透明性。本发明的头发定型组合物可以毫无问题地从头发中洗出。用该组合物处理的头发具有增加的柔软度和令人愉快的自然感觉。该定型作用原则上还可利于降低喷发胶配制剂中成膜剂的需要量。由于本发明聚合物无气味这一事实,必要的话,还可省却添加掩盖气味的芳香油。出于所述原因,本发明聚合物尤其适于作为头发化妆品制剂中的成膜剂。
优选本发明聚合物用于化妆品制剂中,尤其是用于喷发胶制剂中,其包含如下组分:-0.1-20重量%,优选0.5-10重量%,尤其是2-6重量%聚合物,-1-99.9重量%,优选5-50重量%,尤其是10-20重量%水,-0-95重量%,优选20-60重量%,尤其是25-50重量%常规有机溶剂,如主要是乙醇、异丙醇和二甲氧基甲烷,以及还有丙酮、正丙醇、正丁醇、2-甲氧基丙1-醇、正戊烷、正己烷、环己烷、正庚烷、正辛烷或二氯甲烷或其混合物,-0-90重量%,优选30-80重量%,尤其是45-60重量%常规推进剂,如正丙烷、异丙烷、正丁烷、异丁烷、2,2-二甲基丁烷、正戊烷、异戊烷、二甲基醚、二氟乙烷、一氟三氯甲烷、二氯二氟甲烷或二氯四氟乙烷、HCF 152A或其混合物。
在所述化合物当中,主要使用的推进剂(推进剂气体)是烃类,尤其是丙烷、正丁烷、正戊烷及其混合物,以及还有二甲基醚和二氟乙烷。在某些情况下,所述氯化烃中的一种或多种是在推进剂混合物中共同使用,但基于推进剂混合物计仅以少量、例如不超过20重量%使用。
本发明头发化妆品制剂还特别适于不添加推进剂的泵喷雾制剂,或者适于加有常规压缩气体如氮气、压缩空气或二氧化碳作为推进剂的气溶胶型喷雾剂。
含水的标准喷雾配制剂例如具有下列组成:
2-10重量%聚合物,
10-76重量%乙醇,
2-20重量%水,
10-60重量%二甲基醚和/或丙烷/正丁烷和/或丙烷/异丁烷。
本发明聚合物可以含水或含水-醇溶液、O/W和W/O乳液、洗发剂、霜剂、泡沫、乳液、摩丝、喷雾剂(泵型喷雾剂或气溶胶)、凝胶或凝胶喷雾剂形式存在于终制剂中,因此可与其它常规助剂一起配制。
可提及的其它常规助剂是:表面活性剂,油体,乳化剂,助乳化剂,富脂剂,珠光蜡,基础剂,增稠剂,脂肪,蜡,聚硅氧烷化合物,水溶助长剂,防腐剂,芳香油,染料,稳定剂,pH调节剂,化妆品护理物质和活性成分如AHA、果酸、神经酰胺、植烷三醇、没药醇、泛酰醇、胶原质、前维生素和维生素,例如维生素A、E和C,蛋白质和蛋白质水解产物(例如小麦、杏仁或豌豆蛋白),增溶剂,配合剂,拒斥剂,漂白剂,着色剂,调色剂,鞣剂(例如二羟基丙酮),微细颜料如二氧化钛或氧化锌等。另外还可存在聚合物。
合适的阴离子表面活性剂例如是烷基硫酸盐,烷基醚硫酸盐,烷基磺酸盐,烷基芳基磺酸盐,烷基琥珀酸盐,烷基磺基琥珀酸盐,N-烷氧基肌氨酸盐,酰基牛磺酸盐,酰基羟乙基磺酸盐,烷基磷酸盐,烷基醚磷酸盐,烷基醚羧酸盐,α-烯烃磺酸盐,尤其是碱金属和碱土金属盐,例如钠盐、钾盐、镁盐、钙盐和铵盐以及三乙醇胺盐。烷基醚硫酸盐、烷基醚磷酸盐和烷基醚羧酸盐可在分子中具有1-10个氧化乙烯或氧化丙烯单元,优选1-3氧化乙烯单元。
合适的化合物例如是月桂基硫酸钠、月桂基硫酸铵、月桂基醚硫酸钠、月桂基醚硫酸铵、月桂基肌氨酸钠、油基琥珀酸钠、月桂基磺基琥珀酸铵、十二烷基苯磺酸钠、十二烷基苯磺酸三乙醇胺。
合适的两性表面活性剂例如是烷基甜菜碱、烷基酰氨基丙基甜菜碱、烷基磺基甜菜碱、甘氨酸烷酯、羧基甘氨酸烷酯、两性乙酸烷酯或两性丙酸烷酯、两性二乙酸烷酯或两性二丙酸烷酯。
还可使用例如椰油二甲基磺基丙基甜菜碱、月桂基甜菜碱、椰油酰氨基丙基甜菜碱或椰油两性丙酸钠。
合适的非离子表面活性剂例如是在可为线性或支化的烷基链中具有6-20个碳原子的脂族醇或烷基酚与氧化乙烯和/或氧化丙烯的反应产物。氧化烯的量为以每摩尔醇计约6-60mol。还合适的是烷基胺氧化物、单或二烷基链烷醇酰胺、聚乙二醇的脂肪酸酯、乙氧基化的脂肪酸酰胺、烷基多苷或脱水山梨糖醇醚酯。
另外,本发明制剂还包含常规阳离子表面活性剂,例如季铵化合物,例如十六烷基三甲基氯化铵。
本发明制剂,尤其是呈洗发剂配制剂形式的那些经常包含阴离子表面活性剂如碱表面活性剂,两性和阴离子表面活性剂如辅助表面活性剂。
本发明制剂经常包含2-50重量%,优选5-40重量%,特别优选8-30重量%表面活性剂。
合适的油性物质例如是基于具有6-18,优选8-10个碳原子的脂肪醇的Guerbet醇,线性C6-C22-脂肪酸与线性C6-C22-脂肪醇的酯,支化C6-C13-羧酸与线性C6-C22-脂肪醇的酯,线性C6-C22-脂肪酸与支化醇,尤其是2-乙基己醇的酯,羟基羧酸与线性或支化C6-C22-脂肪醇的酯,尤其是苹果酸二辛酯,线性和/或支化脂肪酸与多元醇(例如丙二醇、二聚二醇或三聚三醇)和/或Guerbet醇的酯,基于C6-C10-脂肪酸的甘油三酸酯,基于C6-C18-脂肪酸的液体甘油一-、二-、三酸酯混合物,C6-C22-脂肪醇和/或Guerbet醇与芳族羧酸,尤其是苯甲酸的酯,植物油,支化伯醇,取代的环己烷,线性和支化C6-C22-脂肪醇碳酸酯,Guerbet碳酸酯,苯甲酸与线性和/或支化C6-C22-醇(例如Finsolv TN)的酯,每个烷基具有6-22个碳原子的线性或支化的对称或不对称的二烷基醚,与多元醇的环氧化脂肪酸酯的开环产物,聚硅氧烷油和/或脂族烃或环烷烃。
合适的油性物质是动物和植物油,例如向日葵油、椰子油、鳄梨油、橄榄油或或羊毛脂。
合适的乳化剂例如是选自下列中至少一种的非离子表面活性剂:
(1)2-30mol氧化乙烯和/或0-5mol氧化丙烯与具有8-22个碳原子的线性脂肪醇、具有12-22个碳原子的脂肪酸和在烷基中具有8-15个碳原子的烷基酚的加成产物;
(2)1-30mol氧化乙烯与甘油的加成产物的C12/18-脂肪酸单-和二酯;
(3)具有6-22个碳原子的饱和和不饱和脂肪酸及其氧化乙烯加成产物的甘油单-和二酯和脱水山梨糖醇单-和二酯;
(4)烷基中具有8-22个碳原子的烷基单-和低聚配糖及其乙氧基化类似物;
(5)15-60mol氧化乙烯与蓖麻油和/或氢化蓖麻油的加成产物;
(6)多元醇,尤其是聚甘油酯,例如聚蓖麻醇酸聚甘油酯、聚-12-羟基硬脂酸聚甘油酯或二聚酸聚甘油酯,还合适的是这类物质中的两种或更多种的混合物;
(7)2-15mol氧化乙烯与蓖麻油和/或氢化蓖麻油的加成产物;
(8)基于线性、支化、不饱和或饱和C6/22-脂肪酸、蓖麻油酸和12-羟基硬脂酸和甘油、聚甘油、季戊四醇、二季戊四醇、糖醇(例如山梨糖醇)、烷基葡糖苷(例如甲基葡糖苷、丁基葡糖苷、月桂基葡糖苷)和聚葡糖苷(例如纤维素)的偏酯;
(9)磷酸单-、二-和三烷基酯,以及磷酸单-、二-和三-PEG烷基酯及其盐;
(10)羊毛蜡醇;
(11)聚硅氧烷-聚烷基-聚醚共聚物或相应的衍生物;
(12)季戊四醇、脂肪酸、柠檬酸和根据德国专利1165574的脂肪醇的混合酯和/或具有6-22个碳原子的脂肪酸、甲基葡萄糖和多元醇,优选甘油或聚甘油的混合酯,以及
(13)聚亚烷基二醇。
氧化乙烯和/或氧化丙烯与脂肪醇、脂肪酸、烷基酚、甘油单-和二酯,以及脂肪酸的脱水山梨糖醇单-和二酯,或者与蓖麻油的加成产物是已知的市购产品。它们是平均烷氧基化程度对应于进行加成反应使用的氧化乙烯和/或氧化丙烯和反应物的量的比例的同系混合物。氧化乙烯与甘油的加成产物的C12/18-脂肪酸单-和二酯由德国专利2024051已知为化妆品制剂的再加脂剂。C8/18-烷基单-和低聚配糖物、它们的制备和它们的用途由现有技术已知。它们的制备尤其通过使葡萄糖或或低聚糖与具有8-18个碳原子的伯醇反应而进行。关于配糖物酯,其中环状糖基与脂肪醇以配糖物形式键接的单配糖物,以及还有低聚合度优选不超过约8的低聚配糖物也是合适的。这里的低聚合度是基于对于工业级产品常见的同系分布的统计平均值。
所用乳化剂还可能是两性离子表面活性剂。术语“两性离子表面活性剂”是指在分子中携带至少一个季铵基团和至少一个羧酸酯基和一个磺酸酯基的那些表面活性化合物。特别合适的两性离子表面活性剂是所谓的甜菜碱,如N-烷基-N,N-二甲基甘氨酸铵,例如椰油烷基二甲基甘氨酸铵,N-酰基氨基丙基-N,N-二甲基甘氨酸铵,例如椰油酰基氨基丙基二甲基甘氨酸铵,和2-烷基-3-羧甲基-3-羟基乙基咪唑啉,其各自在烷基或酰基中具有8-18个碳原子,和羟基乙基羧甲基甘氨酸椰油酰基氨基乙酯。特别优选以CTFA名称为椰油酰氨基丙基甜菜碱已知的脂肪酸酰胺衍生物。同样合适的乳化剂是两性表面活性剂。两性表面活性剂应理解指在分子中除了C8/18-烷基或酰基外还含有至少一个游离氨基和至少一个-COOH-或-SO3H-基团且能形成内盐的那些表面活性化合物。合适的两性表面活性剂的实例是N-烷基甘氨酸、N-烷基丙酸、N-烷基氨基丁酸、N-烷基亚氨基二丙酸、N-羟基乙基-N-烷基酰氨基丙基甘氨酸、N-烷基牛磺酸、N-烷基肌氨酸、2-烷基氨基丙酸和烷基氨基乙酸,其中各自在烷基中具有约8-18个碳原子。特别优选的两性表面活性剂是N-椰油烷氨基丙酸酯、椰油酰基氨基乙氨基丙酸酯和C12/18-酰基肌氨酸。除两性乳化剂之外,季铵乳化剂也是合适的,其中特别优选酯季铵的那些,优选甲基-季铵化的二脂肪酸三乙醇胺酯盐。
作为富脂剂,可使用诸如例如羊毛脂和卵磷脂,以及乙氧基化或酰化的羊毛脂和卵磷脂衍生物,多元醇脂肪酸酯,单甘油酯和脂肪酸链烷醇酰胺之类的物质,其中后者还用作泡沫稳定剂。
合适的珠光蜡的实例是:亚烷基二醇酯,尤其是二硬脂酸乙二醇酯;脂肪酸链烷醇酰胺,尤其是椰子脂肪酸二乙醇酰胺;部分甘油酯,尤其是硬脂酸单甘油酯;任选羟基取代的多元羧酸与具有6-22个碳原子的脂肪醇的酯,尤其是酒石酸的长链酯;脂肪物质,例如总计具有至少24个碳原子的脂肪醇、脂肪酮、脂肪醛、脂肪醚和碳酸脂肪酯,尤其是月桂酮和二硬脂基醚;脂肪酸,如硬脂酸、羟基硬脂酸或二十二碳烷酸、具有12-22个碳原子的烯烃环氧化物与具有12-22个碳原子的脂肪醇和/或具有2-15个碳原子和2-10羟基的多元醇的开环产物及其混合物。
合适的基础剂主要是具有12-22个,优选16-18个碳原子的脂肪醇或羟基脂肪醇,以及还有部分甘油酯、脂肪酸或羟基脂肪酸。优选这些物质与具有相同链长度的烷基低聚葡糖苷和/或脂肪酸N-甲基葡糖酰胺和/或聚-12-羟基硬脂酸聚甘油酯的组合。合适的增稠剂例如是多糖,尤其是黄原酸胶、瓜尔树胶、琼脂、藻酸盐和甲基纤维素,纤维素衍生物,例如羧甲基纤维素和羟乙基纤维素,以及还有较高分子量的脂肪酸的聚乙二醇单-和二酯,聚丙烯酸酯(例如Goodrich的Carbopols或Sigma的Synthalens),聚丙烯酰胺,聚乙二醇和聚乙烯基吡咯烷酮,表面活性剂,例如乙氧基化的脂肪酸甘油酯,脂肪酸与多元醇如季戊四醇或三羟甲基丙烷的酯,具有窄同系物分布的脂肪醇乙氧基化物或烷基低聚葡糖苷,和电解质,如氯化钠和氯化铵。
脂肪的典型实例是甘油酯,以及合适的蜡尤其是蜂蜡、巴西棕榈蜡、小烛树蜡、褐煤蜡、石蜡或微晶蜡,其任选与亲水腊,例如十六烷基硬脂基醇或部分甘油酯组合。可使用的稳定剂是脂肪酸的金属盐,例如镁、铝和/或锌的硬脂酸盐或蓖麻醇酸盐。
合适的聚硅氧烷化合物例如是二甲基聚硅氧烷,甲基苯基聚硅氧烷,环状聚硅氧烷,以及氨基-、脂肪酸-、醇-、聚醚-、环氧-、氟-、配糖物-和/或烷基-改性的聚硅氧烷化合物,其可以在室温下呈液体或树脂形式。脂肪的典型实例是甘油酯,合适的蜡尤其是蜂蜡、巴西棕榈蜡、小烛树蜡、褐煤蜡、石蜡或微晶蜡,其任选与亲水腊,例如十六烷基硬脂基醇或部分甘油酯组合。可使用的稳定剂是脂肪酸的金属盐,例如镁、铝和/或锌的硬脂酸盐。
合适的溶剂尤其是水和具有1-6个碳原子的低级一元醇或多元醇及其混合物;优选的一元醇或多元醇是乙醇、异丙醇、丙二醇、甘油和山梨糖醇。
为了改进流动行为,还可使用水溶助长剂,例如乙醇、异丙醇或多元醇。这里合适的多元醇优选具有2-15个碳原子和至少两个羟基。典型实例是:
-甘油;
-亚烷基二醇,例如乙二醇、二甘醇、丙二醇、丁二醇、己二醇和平均分子量为100-1000道尔顿的聚乙二醇;
-自缩合度为1.5-10的工业级低聚甘油混合物,例如二甘油含量为40-50重量%的工业级二甘油混合物;
-羟甲基化合物,尤其例如三羟甲基乙烷、三羟甲基丙烷、三羟甲基丁烷、季戊四醇和二季戊四醇;
-低级烷基葡糖苷,尤其是在烷基中具有1-8个碳原子的那些,例如甲基-和丁基葡糖苷;
-具有5-12个碳原子的糖醇,例如山梨糖醇或甘露醇;
-具有5-12个碳原子的糖,例如葡萄糖或蔗糖;
-氨基糖,例如葡糖胺。
合适的防腐剂的实例是苯氧基乙醇、甲醛溶液、对羟基苯甲酸酯、戊二醇或山梨酸,以及在Cosmetics Directive的A和B部分的附录6中所列出的其它类物质。
这些物质例如包括对革兰氏阳性菌具有特异性作用的所有合适的防腐剂,例如三氯生(2,4,4’-三氯-2’-羟基二苯醚),双氯苯双胍己烷(1,1’-六亚甲基双[5-(4-氯苯基)二胍]和TTC(3,4,4’-三氯对称二苯脲)。季铵化合物原则上同样是合适的,但偏向用于消毒皂和洗涤液。许多香料也具有抗菌性能。具有对革兰氏阳性菌的特定效果的特定组合用于祛臭香料组合物。另外,大量精油或其特征性成分,例如丁子香油(丁子香酚)、薄荷油(薄荷醇)或百里香油(麝香草酚)表现出显著的抗菌效果。
防腐剂通常以约0.1-0.3重量%的浓度使用。
可提及的芳香油是天然和合成香料的混合物。天然香料是花(百合、熏衣草、玫瑰、茉莉、橙花),茎和叶子(天竺葵、广藿香、苦橙叶),果实(茴香、胡荽、孜然芹、刺柏),果皮(香柠檬、柠檬、橙子),根(肉豆蔻树、当归、芹菜、小豆蔻、广木香、鸢尾根、Calmus),木材(松木、檀香木、愈创木、雪松木、红木),香草和草(龙嵩、柠檬香草、鼠尾草、麝香草),针和枝(云杉、冷杉、松树、矮松),树脂和树胶(白松香、榄香、安息香树脂、没药树、乳香、红没药)的提取物。还合适的是动物原料,例如麝猫香和海狸香。典型的合成芳香化合物是酯、醚、醛、酮、醇和烃类产品。酯类芳香化合物例如是乙酸苄酯、异丁酸苯氧基乙酯、乙酸对叔丁基环己酯、乙酸芳樟酯、乙酸二甲基苄基甲酯、乙酸苯基乙酯、苯甲酸芳樟酯、甲酸苄酯、甲基苯基甘氨酸乙酯、环己基丙酸烯丙酯、丙酸苯烯丙酯和水杨酸苄酯。醚类例如包括苄基·乙基醚,醛类例如包括具有8-18个碳原子的链烷醛、柠檬醛、香茅醛、香茅氧基乙醛、樱草醛、羟基香茅醛、铃兰醛和波洁洪醛(bourgeonal),以及酮类例如包括紫罗兰酮、异甲基紫罗兰酮和甲基·柏木酮,以及醇类包括茴香脑、香茅醇、丁子香酚、异丁子香酚、香叶醇、芳樟醇、苯基乙基醇和松油醇,以及烃类主要包括萜和香脂。然而优选使用在一起产生令人愉快的香味的不同香料的混合物。通常用作香味组分的较低挥发性的精油也适合作为芳香油,例如鼠尾草油、春黄菊油、丁子香油、峰花油、薄荷油、肉桂叶子油、白柠檬花油、杜松浆果油、岩兰草油、乳香油、古蓬香脂油、Labolanum oil和杂薰衣草油。优选单独或以混合物使用香柠檬油、二氢月桂烯醇、铃兰醛、新铃兰醛、香茅醇、苯基乙基醇、α-己基肉桂醛、香叶醇、苄基丙酮、仙客来醛、芳樟醇、Boisambrene Forte、Ambroxan、吲哚、二氢茉莉酮酸甲酯、Sandelice、柠檬油、橘皮油、橙子油、戊基甘醇酸烯丙酯、cyclovertal、杂薰衣草油、香丹参油、β-二氢大马酮、波旁香叶油、水杨酸环己酯、Vertofix Coeur、异-E-Super、Fixolide NP、合成橡苔(Evernyl)、γ-甲基紫罗兰酮、苯基乙酸、乙酸香叶酯、乙酸苄酯、氧化玫瑰、Romillat、Irotyl和Floramat。
可使用的染料是证实适于化妆品目的的物质,如例如出版物“Kosmetische Frbemittel”[化妆品着色剂],the Farbstoffkommission derDeutschen Forschungsgemeinschaft[德国研究委员会染料会],VerlagChemie,Weinheim,1984,第81-106页所列出的。这些染料经常基于总混合物以0.001-0.1重量%的浓度使用。
为了设定头发化妆品制剂的特定性能,可有利地以与其它头发定型聚合物的混合物形式使用本发明聚合物。
其它适于该目的的聚合物例如是阴离子、阳离子、两性和中性聚合物。
阴离子聚合物的实例是丙烯酸和甲基丙烯酸或其盐的均聚-和共聚物、丙烯酸和丙烯酰胺及其盐的均聚-和共聚物、多羟基羧酸的钠盐、水可溶或水可分散的聚酯、聚氨酯(例如LuvisetTM PUR)和聚脲。特别合适的聚合物是丙烯酸叔丁酯、丙烯酸乙酯、甲基丙烯酸的共聚物(例如LuvimerTM100P),丙烯酸乙酯和甲基丙烯酸的共聚物(例如LuviflexTM Soft),正叔丁基丙烯酰胺、丙烯酸乙酯、丙烯酸的共聚物(Ultrahold StrongTM),乙酸乙烯酯、巴豆酸和任选的其它乙烯酯的共聚物(例如Luviset CA66TM),任选与醇反应的马来酸酐共聚物,阴离子聚硅氧烷例如乙烯基吡咯烷酮、丙烯酸叔丁酯、甲基丙烯酸的羧基官能化的共聚物(例如LuviskolTM VBM),丙烯酸叔丁酯、甲基丙烯酸和聚二甲基硅氧烷共聚醇的三元共聚物(例如Luviflex Silk)。丙烯酸和甲基丙烯酸与疏水单体例如(甲基)丙烯酸的C4-C30-烷酯、C4-C30-烷基乙烯酯、C4-C30-烷基乙烯基醚和透明质酸的共聚物,以及其它以商品名Amerhold DR-25、Ultrahold、LuvisetTM P.U.R.、AcronalTM、AcudyneTM、LovocrylTM、VersatylTM、AmphomerTM(28-4910、LV-71)、PlaciseTM L53、GantrezTM ES 425、Advantage PlusTM、OmnirezTM2000、ResynTM 28-1310、ResynTM 28-2930、BalanceTM(0/55)、AcudyneTM255、AristoflexTM A或Eastman AQTM已知的聚合物。
其它聚合物是可以INCI名称为聚硅氧烷-7和聚硅氧烷-8获得的聚合物(PlusTM SA70、PlusTM VS70)。
其它聚合物是INCI名称为聚季铵盐的阳离子聚合物,例如乙烯基吡咯烷酮/N-乙烯基咪唑鎓盐的共聚物(LuviquatTM FC、LuviquatTM HM、LuviquatTM MS、LuviquatTM Care),经硫酸二乙酯季铵化的N-乙烯基吡咯烷酮/甲基丙烯酸二甲基氨基乙酯的共聚物(LuviquatTM PQ 11),N-乙烯基己内酰胺/N-乙烯基吡咯烷酮/N-乙烯基咪唑鎓盐的共聚物(LuviquatTMHold),阳离子纤维素衍生物(聚季铵盐-4和-10),丙烯酰胺共聚物(聚季铵盐-),StyleezeTM CC-10,AquaflexTM SF-40和壳聚糖衍生物。
其它合适的聚合物还有中性聚合物,如聚乙烯基吡咯烷酮,N-乙烯基吡咯烷酮和乙酸乙烯酯和/或丙酸乙烯酯的共聚物,聚硅氧烷,聚乙烯基己内酰胺及其与N-乙烯基吡咯烷酮的共聚物,聚乙烯亚胺及其盐,聚乙烯基胺及其盐,纤维素衍生物,聚天冬氨酸盐和衍生物。这些包括以下列商品名已知的聚合物:LuviskolTM(K、VA、Plus)、PVP K、PVP/VA、AdvantageTMHC和H2O LD EP-1。
另外,生物聚合物也是合适的,即由可自然再生的原料获得的并由天然单体结构单元构成的聚合物,例如纤维素衍生物、壳多糖、脱乙酰壳多糖、DNA、透明质酸和RNA衍生物。
其它聚合物是甜菜碱聚合物,如Yukaformers(R205,SM)和Diaformers。
下列包括上列聚合物的INCI/CTFA名称和制造商:
INCI/CTFA | 聚合物 | 制造商 |
丙烯酸酯共聚物 | Amerhold DR-25 | Amerchol |
PVP/VA共聚物 | Luviskol VA | BASF |
聚乙烯基己内酰胺 | Luviskol Plus | BASF |
苯乙烯/丙烯酸酯共聚物 | Acronal 290 D,296 D | BASF |
VA/巴豆酸酯共聚物 | Luviset CA 66 | BASF |
丙烯酸酯/丙烯酰胺共聚物 | Ultrahold 8 | BASF |
丙烯酸酯/丙烯酰胺共聚物 | Ultrahold Strong | BASF |
丙烯酸酯共聚物 | Luviflex Soft | BASF |
丙烯酸酯共聚物 | Luvimer 100P,36D,30E | BASF |
聚季铵盐46 | Luviquat Hold | BASF |
聚氨酯-1 | Luviset P.U.R. | BASF |
甲基丙烯酰基乙基甜菜碱/丙烯酸酯共聚物 | Diaformer | Clariant |
二甘醇/CHDM/间苯二甲酸酯/SIP共聚物 | Eastman AQ聚合物 | Eastman |
VA/巴豆酸酯共聚物 | Aristoflex A | Hoechst Celanese |
丙烯酸酯/双丙酮丙烯酰胺共聚物 | Plascize L-53 | Goo Chemical |
PVP | PVP K;Luviskol K | ISP;BASF |
PVP/VA共聚物 | PVP/VA | ISP |
乙烯基己内酰胺/PVP/甲基丙烯酸二甲基氨基乙酯共聚物 | 共聚物VC713(=Advantage HC) | ISP |
乙烯基己内酰胺/PVP/甲基丙烯酸二甲基氨基乙酯共聚物 | H2OLDEP-1 | ISP |
PVM/MA丁酯共聚物 | Gantrez ES 425 | ISP |
VA/马来酸丁酯/丙烯酸异冰片酯 | Advantage Plus | ISP |
PVM的乙酯/MA共聚物 | Omnirez 2000 | ISP |
PVP/DMAPA丙烯酸酯共聚物 | Styleeze CC-10 | ISP |
PVP/乙烯基己内酰胺/DMAPA丙烯酸酯共聚物 | Aquaflex SF-40 | ISP |
甲基丙烯酰基乙基甜菜碱/丙烯酸酯共聚物 | Yukaformer R205Yukaformer SM | MitsubishiMitsubishi |
VA/巴豆酸酯/共聚物 | Resyn 28-1310 | National Starch |
VA/巴豆酸酯/新癸酸酯共聚物 | Resyn 28-2930 | National Starch |
VA/巴豆酸酯/乙烯基/新癸酸酯共聚物 | Luviset CAN | BASF |
辛基丙烯酰胺/丙烯酸酯/甲基丙烯酸丁基氨基乙酯共聚物 | Amphomer 28-4910 | National Starch |
辛基丙烯酰胺/丙烯酸酯/甲基丙烯酸丁基氨基乙酯共聚物 | Amphomer LV-71 | National Starch |
丙烯酸酯/辛基丙烯酰胺共聚物 | Versatyl 42 | National Starch |
辛基丙烯酰胺/丙烯酸酯共聚物 | Versatyl 90 | National Starch |
聚硅氧烷-7 | PlusTM SA70 | 3M |
聚硅氧烷-8 | PlusTM VS70 | 3M |
丙烯酸酯共聚物 | Balance 0/55 | National Starch |
辛基丙烯酰胺/丙烯酸酯/甲基丙烯酸丁基氨基乙酯共聚物 | Lovocryl 47 | National Starch |
丙烯酸酯/丙烯酸羟酯 | Acudyne | Rohm & Haas |
辅助剂和添加剂的总含量基于组合物计可为1-50重量%,优选5-40重量%。
辅助剂可在聚合过程中存在和/或在聚合之后加入。
聚合物尤其适用于化妆品组合物。例如它们可在化妆品组合物中用于清洁皮肤。这类化妆品清洁剂选自块皂,如盥洗皂、酪状皂、透明皂、高级香皂、祛臭皂、洗面皂、婴儿皂、护肤皂、擦洗皂和合成清洁剂;液体皂,如膏状皂、柔软皂和洗涤膏;以及液体洗液、淋浴和盆浴用品,如洗涤液、淋浴用品和凝胶、泡沫浴、浴油和擦洗剂、剃须泡沫、化妆水和膏霜。
本发明制剂还可用于皮肤护理用化妆品制剂中。该皮肤护理组合物尤其呈W/O或O/W皮肤用霜、日霜和夜霜、眼霜、面霜、抗皱霜、保湿霜、增白霜、维生素霜、润肤液、护理液和润肤乳液形式。
它们还适合诸如面部营养剂、敷面剂、祛臭剂和其它化妆品乳液的皮肤用化妆品制剂。
另外,本发明聚合物可用作毛孔清洁或皮肤紧致用条,用于抗粉刺组合物,拒斥剂,剃须制剂,脱毛组合物,个人卫生组合物,护足组合物和用于婴儿护肤用品。
非常特别优选在修饰性化妆品的制剂中使用本发明聚合物,尤其是以粉末形式存在的聚合物。
对于化妆品制剂特别合适的聚合物是可通过自由基聚合根据权利要求1和/或2的如下单体混合物而获得的那些:
(a1)49.5-99重量%(甲基)丙烯酸酯,尤其是丙烯酸叔丁酯,
(a2)0.5-40重量%另一种(甲基)丙烯酸酯,尤其是甲基丙烯酸,
(b)0.5-20重量%下式的含聚氧化烯的聚硅氧烷衍生物:
其中R1=-CH3
R4=-H、-COCH3、C1-C4烷基n=1-6,尤其是2-4,优选3x和y是使得聚硅氧烷嵌段的分子量为1000-10,000的整数,a、b可以是0-50的整数,条件是a和b之和大于0。
可提及的装饰性化妆品制剂的实例是掩饰用棒、舞台用化妆品、睫毛油和眼影、唇膏、眼线笔、眼线膏、化妆品、粉底化妆品、腮红、脂粉和眉笔,尤其是指甲油。
聚合物通常基于制剂的总重量以约0.001-20重量%,优选0.1-10重量%的量存在化妆品制剂中。
实施例
实施例1
制备聚合物(乳液聚合)
由120g水、6.9g Disponil FES77(=烷基醚磺酸钠盐,Henkel)、126g聚二甲基硅氧烷共聚醇(Belsil DMC6031)和113g进料1制备混合物,并加热至80℃。然后加入24g 7%浓度的过硫酸钠水溶液。然后在2小时内计量加入进料1。在蒸汽蒸馏之后,将该混合物冷却至60℃,并计量加入108g碳酸氢钾溶液。
进料1:
789g丙烯酸叔丁酯
261g甲基丙烯酸
540g水
63g Disponil FES77
4.53g 正十四烷硫醇
实施例2
实施例2的制备按照实施例1进行,但用正二十烷硫醇代替正十四烷硫醇。
实施例3
由1290g水、6.9gDisponol FES77、126g聚二甲基硅氧烷共聚醇(BelsilDMC6031)和113g进料1制备溶液,并加热至80℃。然后加入24g 7%浓度的过硫酸钠水溶液。在2小时内计量加入进料1。在另外2小时后和冷却至65℃之后,加入5.4g过氧化氢(30%浓度的水溶液)。在蒸汽蒸馏之后,将该混合物冷却至60℃,并计量加入108g碳酸氢钾溶液(10%浓度)。
进料1对应于实施例1。
实施例4
实施例4按照实施例3制备,但用正二十烷硫醇代替正十四烷硫醇。
实施例5
实施例5按照实施例3制备,但用正癸硫醇代替正十四烷硫醇。
实施例6
实施例6按照实施例3制备,但用正十二烷硫醇代替正十四烷硫醇。
实施例7
由372g水、2.4g Disponil FES77(=烷基醚磺酸钠盐,Henkel)、42g聚二甲基硅氧烷共聚醇(Belsil DMC6031=PEG/PPG-25/25聚二甲基硅氧烷,Wacker)和35g进料1制备混合物,并加热至40℃。然后加入8g 7%浓度的过硫酸钠水溶液。然后将该混合物加热至80℃,然后在2小时内计量加入进料1。然后加入89g水,并将该混合物于80℃后聚合2小时。在冷却至60℃后,加入47g碳酸氢钾溶液(10%浓度)。
进料1:
150g 水
21.6g Disponil FES77
263g丙烯酸叔丁酯
88g甲基丙烯酸
0.96g正十四烷硫醇
实施例8
实施例8按照实施例7制备,但用正二十烷硫醇代替正十四烷硫醇。
对比例
对比例按照实施例7制备,但用硫代乙醇酸乙基己酯代替正十四烷硫醇。
将根据实施例1-8和对比例制备的分散体通过喷雾干燥转化成粉末形式。
根据实施例1-8和对比例制备的聚合物以及由其制备的粉末的气味评估通过由5个试验者一组来进行。为此,将根据实施例制备的聚合物干燥,溶解在30%浓度的乙醇溶液中,然后配制成3%浓度水溶液,并用2-氨基-2-甲基丙醇100%中和。对于粉末的气味评估,将粉末溶解在30%浓度的乙醇溶液中,然后配制成3%浓度水溶液并中和。
气味性能的评估根据下列分级进行:
“1”无味
“2”弱的令人不愉快的气味
“3”强的令人不愉快的气味。
粉末和分散体就气味而言按如下评估:
1级:C3、C4、C6(在每种情况下为分散体和粉末)
2级:C1、C2、C5、C7和C8(在每种情况下为分散体和粉末)
3级:对比例(分散体和粉末)。
含有DME的喷发胶
聚合物 | 80∶20混合比 | 50∶50混合比 | 20∶80混合比 |
如C1-C8的粉末/LuviskolVA37 | 3.2%如C1-C8的粉末1.6%LuviskolVA37E0.74%AMP54.46%乙醇40.0%DME | 2.0%如C1-C8的粉末4.0%LuviskolVA37E0.46%AMP53.54%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%LuviskolVA37E0.19%AMP52.61%乙醇40.0%DME |
如C1-C8的粉末/LuviskolK30 | 3.2%如C1-C8的粉末0.8%LuviskolK300.74%AMP55.26%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%LuviskolK300.46%AMP55.54%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%LuviskolK300.19%AMP55.81%乙醇40.0%DME |
如C1-C8的粉末/LuviskolPlus | 3.2%如C1-C8的粉末2.0%LuviskolPlus0.74%AMP54.06%乙醇40.0%DME | 2.0%如C1-C8的粉末5.0%LuviskolPlus0.46%AMP52.54%乙醇40.0%DME | 0.8%如C1-C8的粉末8.0%LuviskolPlus0.19%AMP51.01%乙醇40.0%DME |
如C1-C8的粉末/LuvisetP.U.R. | 3.2%如C1-C8的粉末2.67%LuvisetP.U.R0.73%AMP53.40%乙醇40.0%DME | 2.0%如C1-C8的粉末6.67%LuvisetP.U.R0.46%AMP50.87%乙醇40.0%DME | 0.8%如C1-C8的粉末10.67%LuvisetP.U.R0.19%AMP48.34%乙醇40.0%DME |
如C1-C8的粉末/Luvimer100P | 3.2%如C1-C8的粉末0.8%Luvimer100P0.93%AMP55.07%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%Luvimer100P0.94%AMP55.06%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%Luvimer100P0.95%AMP55.05%乙醇40.0%DME |
如C1-C8的粉末/Ultrahold8 | 3.2%如C1-C8的粉末0.8%Ultrahold80.82%AMP55.18%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%Ultrahold80.66%AMP55.34%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%Ultrahold80.51%AMP55.49%乙醇40.0%DME |
如C1-C8的粉末/UltraholdStrong | 3.2%如C1-C8的粉末0.8%UltraholdStrong0.84%AMP55.16%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%UltraholdStrong0.71%AMP55.29%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%UltraholdStrong0.59%AMP55.41%乙醇40.0%DME |
如C1-C8的粉末/LuvisetCA66 | 3.2%如C1-C8的粉末0.8%LuvisetCA660.82%AMP55.18%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%LuvisetCA660.69%AMP55.31%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%LuvisetCA660.53%AMP55.47%乙醇40.0%DME |
如C1-C8的粉末/LuvisetCAN | 3.2%如C1-C8的粉末0.8%LuvisetCAN0.82%AMP55.18%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%LuvisetCAN0.70%AMP55.30%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%LuvisetCAN0.54%AMP55.46%乙醇40.0%DME |
如C1-C8的粉末/Amphomer | 3.2%如C1-C8的粉末0.8%Amphomer0.88%AMP55.12%乙醇40.0%DME | 2.0%如C1-C8的粉末2.0%Amphomer0.83%AMP54.87%乙醇40.0%DME | 0.8%如C1-C8的粉末3.2%Amphomer0.77%AMP55.23%乙醇40.0%DME |
含有Pr/Bu 3.5或Pr/Bu 3.5和DME的喷发胶
聚合物 | 80∶20混合比 | 50∶50混合比 | 20∶80混合比 |
如C1-C8的粉末/LuviskolVA37 | 3.2%如C1-C8的粉末1.6%LuviskolVA37E0.74%AMP54.46%乙醇10.0%Pr/Bu3.530.0%DME | 2.0%如C1-C8的粉末4.0%LuviskolVA37E0.46%AMP52.54%乙醇10.0%Pr/Bu3.530.0%DME | 0.8%如C1-C8的粉末3.2%LuviskolVA37E0.19%AMP52.61%乙醇10.0%Pr/Bu3.530.0%DME |
如C1-C8的粉末/LuviskolK30 | 3.2%如C1-C8的粉末0.8%LuviskolK300.74%AMP55.26%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末2.0%LuviskolK300.46%AMP55.54%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末3.2%LuviskolK300.19%AMP55.81%乙醇40.0%Pr/Bu3.5 |
如C1-C8的粉末/LuviskolPlus | 3.2%如C1-C8的粉末2.0%LuviskolPlus0.74%AMP54.06%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末5.0%LuviskolPlus0.46%AMP52.54%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末8.0%LuviskolPlus0.19%AMP51.01%乙醇40.0%Pr/Bu3.5 |
如C1-C8的粉末/LuvisetP.U.R. | - | 2.0%如C1-C8的粉末6.67%LuvisetP.U.R0.46%AMP50.87%乙醇10%Pr/Bu3.530.0%DME | 0.8%如C1-C8的粉末10.67%LuvisetP.U.R0.19%AMP48.34%乙醇15%Pr/Bu3.525.0%DME |
如C1-C8的粉末/Luvimer100P | 3.2%如C1-C8的粉末0.8%Luvimer100P0.93%AMP55.07%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末2.0%Luvimer100P0.94%AMP55.06%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末3.2%Luvimer100P0.95%AMP55.05%乙醇40.0%Pr/Bu3.5 |
如C1-C8的粉末/Ultrahold8 | 3.2%如C1-C8的粉末0.8%Ultrahold80.82%AMP55.18%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末2.0%Ultrahold80.66%AMP55.34%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末3.2%Ultrahold80.51%AMP55.49%乙醇40.0%Pr/Bu3.5 |
如C1-C8的粉末/UltraholdStrong | 3.2%如C1-C8的粉末0.8%UltraholdStrong0.84%AMP55.16%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末2.0%UltraholdStrong0.71%AMP55.29%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末3.2%UltraholdStrong0.59%AMP55.41%乙醇40.0%Pr/Bu3.5 |
如C1-C8的粉末/LuvisetCA66 | 3.2%如C1-C8的粉末0.8%LuvisetCA660.82%AMP55.18%乙醇10.0%Pr/Bu3.530.0%DME | 2.0%如C1-C8的粉末2.0%LuvisetCA660.69%AMP55.31%乙醇10.0%Pr/Bu3.530.0%DME | 0.8%如C1-C8的粉末3.2%LuvisetCA660.53%AMP55.47%乙醇10.0%Pr/Bu3.530.0%DME |
如C1-C8的粉末/LuvisetCAN | 3.2%如C1-C8的粉末0.8%LuvisetCAN0.82%AMP55.18%乙醇20.0%Pr/Bu3.520.0%DME | 2,0%如C1-C8的粉末2.0%LuvisetCAN0.70%AMP55.3%乙醇20.0%Pr/Bu3.520.0%DME | 0.8%如C1-C8的粉末3.2%LuvisetCAN0.54%AMP55.46%乙醇20.0%Pr/Bu3.520.0%DME |
如C1-C8的粉末/Amphomer | 3.2%如C1-C8的粉末0.8%Amphomer0.88%AMP55.12%乙醇40.0%Pr/Bu3.5 | 2.0%如C1-C8的粉末2.0%Amphomer0.83%AMP54.87%乙醇40.0%Pr/Bu3.5 | 0.8%如C1-C8的粉末3.2%Amphomer0.77%AMP55.23%乙醇40.0%Pr/Bu3.5 |
泵型喷雾剂
聚合物 | 8∶2混合比 | 1∶1混合比 | 2∶8混合比 |
如C1-C8的粉末LuviskolVA37 | 5.4%如C1-C8的粉末2.66%LuviskolVA37E1.27%AMP90.67%乙醇 | 3.37%如C1-C8的粉末6.66%LuviskolVA37E0.79%AMP89.18%乙醇 | 1.35%如C1-C8的粉末10.64%LuviskoIVA37E0.32%AMP87.69%乙醇 |
如C1-C8的粉末/LuviskolK30 | 5.4%如C1-C8的粉末1.33%LuviskolK301.27%AMP92.0%乙醇 | 3.37%如C1-C8的粉末3.33%LuviskolK300.79%AMP87.51%乙醇 | 2.69%如C1-C8的粉末5.32%LuviskolK300.32%AMP85.03%乙醇 |
如C1-C8的粉末/LuviskolPlus | 5.4%如C1-C8的粉末3.33%LuviskolPlus1.27%AMP90.0%乙醇 | 3.37%如C1-C8的粉末8.33%LuvikolPlus0.79%AMP92.51%乙醇 | 1.35%如C1-C8的粉末13.3%LuviskolPlus0.32%AMP91.55%乙醇 |
如C1-C8的粉末/LuvisetP.U.R. | 5.4%如C1-C8的粉末4.43%LuvisetP.U.R1.27%AMP88.85%乙醇 | 3.37%如C1-C8的粉末11.1%LuvisetP.U.R0.79%AMP84.74%乙醇 | 1.35%如C1-C8的粉末17.73%LuvisetP.U.R0.32%AMP80.6%乙醇 |
如C1-C8的粉末/Luvimer100P | 5.4%如C1-C8的粉末1.33%Luvimer100P1.55%AMP91.72%乙醇 | 3.37%如C1-C8的粉末3.33%Luvimer100P1.56%AMP91.74%乙醇 | 1.35%如C1-C8的粉末5.32%Luvimer100P1.58%AMP91.75%乙醇 |
如C1-C8的粉末/Ultrahold8 | 5.4%如C1-C8的粉末1.33%Ultrahold81.36%AMP91.91%乙醇 | 3.37%如C1-C8的粉末3.33%Ultrahold81.1%AMP92.2%乙醇 | 1.35%如C1-C8的粉末5.32%Ultrahold80.85%AMP92.48%乙醇 |
如C1-C8的粉末/UltraholdStrong | 5.4%如C1-C8的粉末1.33%UltraholdStrong1.4%AMP91.87%乙醇 | 3.37%如C1-C8的粉末3.33%UltraholdStrong1.18%AMP92.12%乙醇 | 1.35%如C1-C8的粉末5.32%UltraholdStrong0.98%AMP92.35%乙醇 |
如C1-C8的粉末/LuvisetCA66 | 5.4%如C1-C8的粉末1.33%LuvisetCA661.36%AMP91.91%乙醇 | 3.37%如C1-C8的粉末3.33%LuvisetCA661.15%AMP92.15%乙醇 | 1.35%如C1-C8的粉末5.32%LuvisetCA660.88%AMP92.15%乙醇 |
如C1-C8的粉末/LuvisetCAN | 5.4%如C1-C8的粉末1.33%LuvisetCAN1.37%AMP91.9%乙醇 | 3.37%如C1-C8的粉末3.33%LuvisetCAN1.17%AMP92.13%乙醇 | 1.35%如C1-C8的粉末5.32%LuvisetCAN0.9%AMP92.43%乙醇 |
如C1-C8的粉末/Amphomer | 5.4%如C1-C8的粉末1.33%Amphomer1.47%AMP91.8%乙醇 | 3.37%如C1-C8的粉末3.33%Amphomer1.38%AMP91.92%乙醇 | 1.35%如C1-C8的粉末3.33%Amphomer1.28%AMP94.04%乙醇 |
基于异丁烷和正戊烷的喷发胶配制剂
A)
3.4% 如C1-C8的粉末
0.79% AMP=2-氨基-2-甲基-1-丙醇
14.2% 正戊烷
2.4% 正丁烷
35.9% 异丁烷
43.31% 无水乙醇
B)
3.0% Ultrahold Strong
0.5% 如C1-C8的粉末
0.48% AMP
0.03% DC190(PEG/PPG-18/18聚二甲基硅氧烷;DOW Corning)
14.2% 正戊烷
2.4% 正丁烷
35.9% 异丁烷
43.49% 乙醇
亮发喷雾剂
2.0% 如C1-C8的粉末
0.46% AMP
1.0% DC556(苯基聚三甲基硅氧烷;DOW Corning)
0.1% 烟酰胺
0.2% D-泛酰醇
14.2% 正戊烷
35.9% 正丁烷
46.14% 乙醇
含有HFC152A的喷发胶VOC 80
3.4% 如C1-C8的粉末
0.79% AMP
60.0% 无水乙醇
15.81% HFC152A(氢氟烃152a)
20% 二甲基醚
含有维生素的喷发胶VOC 55
3.4% 如C1-C8的粉末
0.79% AMP
0.1% 烟酰胺
0.1% 泛酰醇
40.61% 水
15.0% 乙醇
40.0% DME
用于头发的防晒泵型喷雾剂
1% 如C1-C8的粉末
0.23% AMP
2% Uvinul MS 40(BASF AG)
96.77% 乙醇
VOC 80配制剂
3.96% 如C1-C8的粉末
0.92% AMP
0.10% 己二酸二异丁酯
0.05% 异癸烷
0.10% 芳香油
0.05% D-泛酰醇USP
14.78% 蒸馏水
40.04% 乙醇
40.0% DME(二甲基醚)
VOC 55配制剂
3.96% 如C1-C8的粉末
0.92% AMP
36.16% 蒸馏水
18.96% 乙醇
40.0% DME
头发修复剂
3.0% 如C1-C8的粉末
0.69% AMP
0.2% 水解的小麦蛋白
0.5% D-泛酰醇
5.0% 丙二醇
10.0% 无水乙醇
80.61% 水
具有UV保护的发用亮发凝胶
相A 0.8% Carbopol 2001 ETD(Carbomer,B.F.Goodrich)
34.84% 水
相B 5.0% Abil 200
3.0% Karion F(D-山梨糖醇)
3.0% 1,2-丙二醇
1.0% Cremophor RH40
q.s. 防腐剂
相C 50.0% 水
0.5% Uvinul P25
1.0% 如C1-C8的粉末
0.23% AMP
相D 0.63% AMP
发用凝胶
相A 0.50% Carbopol 940
49.50% 蒸馏水
0.40% 三乙醇胺
相B 0.50% 如C1-C8的粉末
0.12% AMP
20.00% 无水乙醇
28.98% 蒸馏水
洗发剂配制剂
1.0% 如C1-C8的粉末
0.23% AMP
10.0% Tegobetaine L 7
40.0% Texapon NSO
0.1% Euxyl K 100
2.0% NaCl
46.67% 水
含有Luviquat Care的洗发剂配制剂
1.0% 如C1-C8的粉末
0.23% AMP
7.7% Luviquat Care
10.0% Tegobetaine L 7
40.0% Texapon NSO
0.1% Euxyl K 100
2.0% NaCl
38.97% 水
头发用鸡尾酒
A)
3.00 Luvigel EM
2.00 Wacker Belsil DM 1000
3.00 Wacker Belsil CM 1000
2.00 Wacker Belsil PDM 200
2.00 Wacker Belsil ADM 6057 E
0.50 Wacker Belsil DMC6031
1.00 夏威夷果油
0.50 维生素E乙酸酯
1.00 Cremophor RH 40
0.40 ”Disco”芳香油
B)
2.00 如C1-C8的粉末
0.46 AMP
0.10 Euxyl K 100
加至100蒸馏水
睫毛油
相A 1.5% Cremophor A6
1.5% Cremophor A25
2.0% 硬脂酸
3.0% Imwitor 960 K
3.0% Softisan 100
1.5% Luvigel EM
10.0% Dow Corning 345
相B 2.0% 如C1-C8的粉末
0.46% AMP
0.3% Germal 115
74.24% 水
相C 0.5% 苯氧基乙醇
睫毛油
A)
25.72 蒸馏水
3.00 Lutrol E 400
0.50 Keltrol F
0.10 Abiol
0.40 Euxyl K 400
1.30 Neutrol TE
B)
25.60 蒸馏水(热水)
0.98 AMP
4.40 如C1-C8的粉末
C)
8.00 巴西棕榈蜡
4.00 蜂蜡
4.00 异十六烷
4.00 Panalene H 300 E
5.00 硬脂酸
1.00 单硬脂酸甘油酯
2.00 Finsolv TN
D)
7.00 Sicomet Green P 77 288
E)
3.00 Sicopearl Fantastico Gold
唇膏
商品名 INCI %
Abil Wax 9801 十六烷基聚二甲基硅氧烷 0.56
Carnauba Wax 2442 L 巴西棕榈蜡 2.89
Candelilla Wax 2039 Y 小烛树蜡 8.67
Lunacera W 80 纯地蜡 3.82
Rewopol PIB 1000 聚异丁烯 1.16
Adeps Lanae Lite 羊毛脂 34.68
Crodamol ML 十四醇乳酸酯 15.03
Napvis D 10 Napvis聚丁烯 2.31
Luvitol EHO 辛酸十六十八烷酯 25.26
蓖麻油 蓖麻油 4.05
天然(-)-α-红没药醇. 没药醇 0.12
维生素E乙酸酯 生育酚醋酸酯 0.87
d,l-α-生育酚 生育酚 0.58
基础唇膏质量 49.50g
如C1-C8的粉末 0.50g
将基础唇膏熔融并在搅拌下引入粉末。
Claims (17)
1.一种通过使以下组分进行自由基聚合而制备聚合物的方法:
(a)烯属不饱和单体
(b)含聚氧化烯的聚硅氧烷衍生物,
该方法包括在碳链长度为C13-C22的链烷硫醇存在下进行该聚合。
2.一种通过使以下组分进行自由基聚合而制备聚合物的方法:
(a)烯属不饱和单体
(b)含聚氧化烯的聚硅氧烷衍生物,
该方法包括:
i)在碳链长度为C10-C22的链烷硫醇存在下进行该聚合,然后
ii)用过氧化氢处理。
3.如权利要求1和/或2所要求的方法,其中将聚合物转化成粉末形式。
4.如权利要求3所要求的方法,其中将聚合物通过喷雾干燥转化成粉末形式。
5.如前述权利要求任一项所要求的方法,其中使用线性链烷硫醇。
6.如前述权利要求任一项所要求的方法,其中基于单体(a)计使用0.1-5重量%的链烷硫醇。
7.如前述权利要求任一项所要求的方法,其中所用的含聚氧化烯的聚硅氧烷衍生物(b)是式I的那些:
其中:
R2=CH3或者
R3=CH3或者R2
R4=H、CH3、
R6是具有1-40个碳原子的有机基团,其可含有氨基、羧酸基团或磺酸酯基,
并且当c=0时,还是无机酸的阴离子,以及
其中基团R1可相同或不同,来自具有1-20个碳原子的脂族烃、具有3-20个碳原子的环状脂族烃,具有芳香性或者与R5相同,其中:
条件是R1、R2或R3中至少一个是根据上述定义的含聚氧化烯的基团,
n是1-6的整数,
x和y是使得聚硅氧烷嵌段的分子量为300-30,000的整数,
a、b可以是0-50的整数,条件是a和b之和大于0,以及c为0或1。
8.如权利要求7所要求的方法,其中式I具有如下含义:
其中R1和R5具有权利要求7中所述的含义。
9.如权利要求8所要求的方法,其中式I具有如下含义:
其中
R1=-CH3
R4=-H、-COCH3、C1-C4烷基
n=1-6,尤其是2-4,
x和y是使得聚硅氧烷嵌段的分子量为1000-10,000的整数,
a、b可以是0-50的整数,条件是a和b之和大于0。
10.如前述权利要求任一项所要求的方法,其中(a)是至少一种(甲基)丙烯酸酯。
11.如前述权利要求任一项所要求的方法,其中(a)选自
(a1)丙烯酸叔丁酯和/或
(a2)甲基丙烯酸。
12.如前述权利要求任一项所要求的方法,其中
(a)占50-99.9重量%,以及
(b)占0.1-50重量%,
条件是它们之和为100%。
13.如前述权利要求任一项所要求的方法,其中
(a1)占49.5-99重量%,以及
(a2)占0.5-40重量%,
(b)占0.5-20重量%。
条件是它们之和为100%。
14.一种可通过权利要求1-13中任一项方法获得的聚合物。
15.一种如权利要求14所要求的聚合物,其呈粉末形式。
16.如权利要求14和/或15所要求的聚合物在化妆品制剂中的用途。
17.如权利要求16所要求的用途,用于头发化妆品制剂和修饰性化妆品制剂。
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE10163523A DE10163523A1 (de) | 2001-12-21 | 2001-12-21 | Verfahren zur Herstellung von Polymerisaten |
DE10163523.0 | 2001-12-21 |
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Publication Number | Publication Date |
---|---|
CN1606599A true CN1606599A (zh) | 2005-04-13 |
Family
ID=7710550
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Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
CN02825696.4A Pending CN1606599A (zh) | 2001-12-21 | 2002-12-17 | 聚合物的制备方法 |
Country Status (7)
Country | Link |
---|---|
US (1) | US20050069510A1 (zh) |
EP (1) | EP1458817A1 (zh) |
JP (1) | JP2005513234A (zh) |
CN (1) | CN1606599A (zh) |
AU (1) | AU2002358738A1 (zh) |
DE (1) | DE10163523A1 (zh) |
WO (1) | WO2003054088A1 (zh) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102666594A (zh) * | 2009-12-23 | 2012-09-12 | 陶氏环球技术有限责任公司 | 用于制备低气味共聚物乳胶的方法 |
CN113287812A (zh) * | 2021-05-17 | 2021-08-24 | 南京林业大学 | 一种抗菌抗病毒可降解口罩及其制备方法 |
Families Citing this family (4)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
DE10118478A1 (de) * | 2001-04-12 | 2002-10-17 | Basf Ag | Polysiloxanhaltige Polymere zur Antiknitterausrüstung von cellulosehaltigen Textilien |
WO2004078810A2 (de) * | 2003-03-07 | 2004-09-16 | Basf Aktiengesellschaft | Polymere produkte |
FR2915388B1 (fr) * | 2007-04-27 | 2010-12-24 | Oreal | Film hydrosoluble cosmetique |
FR3075631B1 (fr) | 2017-12-21 | 2020-04-03 | Lvmh Recherche | Composition de mascara contenant un ester de tetrahydroxypropylethylene diamine |
Family Cites Families (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2727032B2 (ja) * | 1991-03-27 | 1998-03-11 | 東洋化成工業株式会社 | 樹脂組成物エマルションの製造法 |
DE4414465C1 (de) * | 1994-04-26 | 1995-05-11 | Goldschmidt Ag Th | Polymethacrylsäureester-Polysiloxan-Blockmischpolymerisate, Verfahren zu ihrer Herstellung und ihre Verwendung als Modifizierungsmittel und als Lackadditive |
EP0998254B1 (de) * | 1997-07-23 | 2008-12-24 | Basf Se | Verwendung von polysiloxanhaltigen polymeren für kosmetische formulierungen |
DE19907587A1 (de) * | 1999-02-22 | 2000-08-24 | Basf Ag | Haarkosmetische Formulierungen |
DE10163118A1 (de) * | 2001-12-21 | 2003-07-03 | Basf Ag | Verfahren zur Herstellung von Polymerisaten |
-
2001
- 2001-12-21 DE DE10163523A patent/DE10163523A1/de not_active Withdrawn
-
2002
- 2002-12-17 EP EP02793049A patent/EP1458817A1/de not_active Withdrawn
- 2002-12-17 JP JP2003554796A patent/JP2005513234A/ja not_active Withdrawn
- 2002-12-17 US US10/497,989 patent/US20050069510A1/en not_active Abandoned
- 2002-12-17 AU AU2002358738A patent/AU2002358738A1/en not_active Abandoned
- 2002-12-17 CN CN02825696.4A patent/CN1606599A/zh active Pending
- 2002-12-17 WO PCT/EP2002/014397 patent/WO2003054088A1/de active Application Filing
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN102666594A (zh) * | 2009-12-23 | 2012-09-12 | 陶氏环球技术有限责任公司 | 用于制备低气味共聚物乳胶的方法 |
US8691937B2 (en) | 2009-12-23 | 2014-04-08 | Styron Europe Gmbh | Method for the preparation of low odor copolymer latexes |
CN113287812A (zh) * | 2021-05-17 | 2021-08-24 | 南京林业大学 | 一种抗菌抗病毒可降解口罩及其制备方法 |
Also Published As
Publication number | Publication date |
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DE10163523A1 (de) | 2003-07-03 |
JP2005513234A (ja) | 2005-05-12 |
WO2003054088A1 (de) | 2003-07-03 |
AU2002358738A1 (en) | 2003-07-09 |
EP1458817A1 (de) | 2004-09-22 |
US20050069510A1 (en) | 2005-03-31 |
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