CN117479921A - 用于增稠极性或非极性油的包含至少一种油和至少一种聚(衣康酸酯)的共聚物增稠组合物 - Google Patents
用于增稠极性或非极性油的包含至少一种油和至少一种聚(衣康酸酯)的共聚物增稠组合物 Download PDFInfo
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Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- 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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8164—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical, and containing at least one other carboxyl radical in the molecule, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers, e.g. poly (methyl vinyl ether-co-maleic anhydride)
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/92—Oils, fats or waxes; Derivatives thereof, e.g. hydrogenation products thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
- A61K2800/48—Thickener, Thickening system
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Birds (AREA)
- Dermatology (AREA)
- Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Lubricants (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Abstract
本发明涉及一种用于增稠极性或非极性油(H2)的共聚物增稠组合物(C),该组合物包含至少一种油(H1)和至少一种由两种单体单元组成的聚(衣康酸酯)(P)。
Description
本发明涉及一种用于增稠极性或非极性油的共聚物组合物;涉及其制备方法;并且涉及包含该增稠组合物的局部用配制品。
化妆品市场中需要增稠油。凝胶形成需要通过胶凝剂形成三维网络,使得能够固定液相或溶剂。可以使用几种策略来实现这一点。它们涉及各种类型的相互作用,包括弱相互作用(氢键、疏水/疏水等)和吸收/吸附现象。
目前提出的增稠解决方案在通用性方面提供了显著的性能和明显的优点,但也存在缺点,尤其是对配制品的感官特性和配制条件有影响。这些物质具有不同的化学性质:二氧化硅衍生物,粘土,聚合物如聚酰胺、聚丙烯酸酯、聚氨酯,蜂蜡,氢化植物油或糖脂肪酯或酰胺。
尽管市场上已经存在具有不同的性质和性能的油增稠剂,但它们的结构与特性之间的关系还没有清楚地确定,这是主要的科学障碍,因为目的是找到从植物来源的材料获得的结构,该结构能够为具有任何类型的性质的油(极性至非极性)提供高性能、不同类型的质地(致密到流体)和有吸引力或至少不令人望而却步的感官特性(不油腻、不发粘、非滑动性)。
因此,难题之一在于找到单一的通用结构或物质,从而允许所有类型的油(从最非极性至最极性)在低剂量下有效增稠,当然,胶凝机制根据油和胶凝剂的性质而不同。
本发明的解决方案是一种用于增稠极性或非极性油(H2)的共聚物组合物(C),该共聚物组合物包含至少一种油(H1)和至少一种聚(衣康酸酯)(P),该至少一种聚(衣康酸酯)由以下各项组成:
-A)衍生自选自由以下化合物组成的组的要素的单体的单体单元:
·具有式(AIId1)
其中Y和Y’相同,表示基团R1O-;或Y和Y’不同,表示HO-基团或基团R1O-,
其中R1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的脂肪族烃基基团,
·具有式(IIf1)
其中Y6和Y’6相同,表示具有式(Y61)的基团;或Y和Y’不同,表示HO-基团或具有式(Y61)的基团:
其中R1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的脂肪族烃基基团,
·具有式(IIg1)
其中Y7和Y’7相同,表示具有式(Y71)的基团;或Y和Y’不同,表示HO-基团或具有式(Y71)的基团:
其中R’1-C(=O)表示含有12至24个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且更特别地是选自由以下组成的组的要素的基团:十二烷酰基、十四烷酰基、十六烷酰基、十八烷酰基、二十烷酰基、二十二烷酰基、油烯基、亚油烯基、亚麻酰基或异硬脂酰基,并且其中x表示大于或等于1并且小于或等于5的自然整数,
以及
-B)衍生自选自由以下化合物组成的组的要素的单体的单体单元:
·具有式(IIa1)
其中Y1和Y’1可以相同或不同,表示HO-基团或具有式(Y11)的基团:
其中m是大于或等于2并且小于或等于10的整数;
·具有式(IIb1)
其中Y2和Y’2可以相同或不同,表示HO-基团或具有式(Y21)的基团:
其中o表示大于或等于2并且小于或等于4的整数;
·具有式(IIc1)
其中Y3和Y’3可以相同或不同,表示HO-基团或具有式(Y31)的基团:
·具有式(IIc1’)
其中Y4和Y’4可以相同或不同,表示HO-基团或具有式(Y41)的基团:
·具有式(IIe1)
其中Y5和Y’5可以相同或不同,表示HO-基团或具有式(Y51)的基团:
O-(CH2)q-OH(Y51),
其中q是大于或等于1并且小于或等于12、更特别地大于或等于3并且小于或等于8的整数;
·具有式(IIh1)
其中Y8和Y’8可以相同或不同,表示HO-基团或具有式(Y81)的基团:
其中R’1-C(=O)表示包含12至36个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且其中x表示大于或等于6并且小于或等于20的自然整数。
当Y或Y’不同并且表示HO-基团时,则存在于式(AIId1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y6或Y’6不同并且表示HO-基团时,则存在于式(IIf1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y7或Y’7不同并且表示HO-基团时,则存在于式(IIg1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y1或Y’1不同并且表示HO-基团时,则存在于式(IIa1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y2或Y’2不同并且表示HO-基团时,则存在于式(IIb1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y3或Y’3不同并且表示HO-基团时,则存在于式(IIc1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y4或Y’4不同并且表示HO-基团时,则存在于式(IIc1’)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
当Y5或Y’5不同并且表示HO-基团时,则存在于式(IIe1)中的羧酸官能团呈游离酸形式或部分或完全盐化形式。
所述增稠组合物(C)允许极性和非极性油(H2)增稠。
出于本发明的目的,术语“盐化”意指存在于单体中的酸官能团呈以盐形式与阳离子缔合的阴离子形式,该阳离子尤其是碱金属盐,如钠或钾阳离子,或如含氮碱的阳离子,如铵盐、赖氨酸盐或单乙醇胺盐(HOCH2-CH2-NH4 +)。它们优选地是钠盐或铵盐。
对于如上所定义的式(AIId1)中、式(Y61)中和式(IIf1’)中的基团R1,术语“包含6至36个碳原子、可选地被一个或多个羟基取代的饱和或不饱和的、直链或支链的脂肪族烃基基团”表示:
-饱和直链烷基基团,例如正己基、正庚基、正辛基、正壬基、正癸基、正十一烷基、正十二烷基、正十三烷基、正十四烷基、正十五烷基、正十六烷基、正十七烷基、正十八烷基、正十九烷基、正二十烷基和正二十二烷基基团;
-不饱和直链基团,如辛烯基、癸烯基、十一碳烯基、十二碳烯基、十三碳烯基、十四碳烯基、十五碳烯基、十六碳烯基、十七碳烯基、十八碳烯基、十九碳烯基、二十碳烯基、二十二碳烯基、4-十二碳烯基和5-十二碳烯基基团;
-被一个或两个羟基取代的包含6至36个碳原子的饱和或不饱和的、直链或支链的脂肪族基团,如羟基十二烷基、羟基十四烷基、羟基十六烷基、羟基十八烷基、羟基二十烷基和羟基二十二烷基,例如12-羟基十八烷基基团;
-衍生自具有式(1)的异烷醇的基团:
(CH3)(CH3)CH-(CH2)r-CH2-OH(1)
其中r表示在2与20之间的整数,例如异癸基、异十一烷基、异十二烷基、异十三烷基、异十四烷基、异十五烷基、异十六烷基、异十七烷基、异十八烷基、异十九烷基、异二十烷基或异二十二烷基基团;
具有式(2)的衍生自格尔伯特醇的支链烷基基团:
CH(CsH2s+1)(CtH2t+1)-CH2-OH(2)
其中t是在4与18之间的整数,s是在2与18之间的整数,并且s+t之和大于或等于6且小于或等于22,例如2-丁基辛基、2-丁基癸基、2-己基辛基、2-己基癸基、2-辛基癸基、2-己基十二烷基、2-辛基十二烷基、2-癸基十四烷基、2-十二烷基十六烷基或2-十四烷基十八烷基基团。
根据甚至更特定的方面,在如上所定义的式(AIId1)和(IIf1)的定义中,R1表示选自由以下组成的组中的要素中的至少一种的基团:正己基、正庚基、正辛基、正壬基、正癸基、正十二烷基、正十四烷基、正十六烷基、正十八烷基、正二十烷基、正二十二烷基、2-己基癸基、2-辛基癸基、2-己基十二烷基、2-辛基十二烷基、2-癸基十四烷基和12-羟基十八烷基基团。
根据特定方面,聚(衣康酸酯)(P)是交联聚(衣康酸酯)(P)。
出于本发明的目的,术语“交联聚(衣康酸酯)(P)”表示如先前所定义的并且还由至少一种衍生自多烯交联单体(AR)的单体单元组成的聚(衣康酸酯)。
术语“多烯交联单体(AR)”表示其化学式包括至少两个烯键并且在涉及构成如上所述的聚(衣康酸酯)的单体的自由基聚合反应期间允许两个或更多个聚合物链连接的化合物。可以在引发自由基聚合过程之前将多烯交联单体(AR)添加至单体中,从而允许制备交联聚(衣康酸酯)。
多烯交联单体(AR)还可以是自由基聚合过程中使用的单体组合物的成分,这是由于在两个或更多个衣康酸分子与一个多元醇分子之间的酯化。
出于本发明的目的,术语“多元醇”表示被至少两个羟基取代的脂肪族分子。
出于本发明的目的,术语“极性油”表示在其分子结构中包含极性基团(即能够与为永久偶极/永久偶极类型的水分子产生静电相互作用的基团)的疏水性化合物。
出于本发明的目的,术语“非极性油”表示不能与为永久偶极/永久偶极类型的水分子产生静电相互作用的疏水性化合物。
出于本发明的目的,术语“疏水性化合物”表示不能与水物理相互作用的化合物。
出于本发明的目的,术语“油”表示疏水和不溶于水的化合物和/或化合物的混合物。
视情况而定,根据本发明的解决方案可以具有以下特征中的一个或多个:
-组合物(C)包含按质量计在20%与80%之间、优选按质量计在40%与60%之间、甚至更优选按质量计在43%与57%之间的油(H1)和按质量计在80%与20%之间、优选按质量计在60%与40%之间、甚至更优选按质量计在57%与43%之间的聚(衣康酸酯)(P);
-油(H1)是在4℃与45℃之间、优选在15℃与45℃之间的温度下并且甚至更优选在15℃与35℃之间的温度下呈液体形式的油;
-油(H1)是矿物油或植物油或这两种类型的油的混合物;
-质量比(P)/(H1)是在5/1与1/5之间、优选在4/1与1/4之间、更优选在3/1与1/3之间、甚至更优选在1/2与2/1之间。
矿物油优选选自:
●链烷烃,异链烷烃或环烷烃如:以名称EmogreenTML15、EmogreenTML19、EmosmartTML15、EmosmartTML19、EmosmartTMV21、IsoparTML、IsoparTMH、IsoparTMG或IsoparTMM出售的烷烃和异烷烃和环烷烃的混合物,
●白色矿物油,如以如下名称出售的产品:MarcolTM52、MarcolTM82、DrakeolTM6VR、EolaneTM130、EolaneTM150,
●包含11至19个碳原子的直链烷烃,并且更特别地是正十一烷、正十二烷、正十三烷,并且甚至更特别地是正十一烷和正十三烷的混合物,
●包含7至20个碳原子的支链烷烃,如异十二烷、异十五烷、异十六烷、异十七烷、异十八烷、异十九烷或异二十烷、或由其INCI名称标识的它们中的一些的混合物:C7-8异链烷烃、C8-9异链烷烃、C9-11异链烷烃、C9-12异链烷烃、C9-13异链烷烃、C9-14异链烷烃、C9-16异链烷烃、C10-11异链烷烃、C10-12异链烷烃、C10-13异链烷烃、C11-12异链烷烃、C11-13异链烷烃、C11-14异链烷烃、C12-14异链烷烃、C12-20异链烷烃、C13-14异链烷烃、C13-16异链烷烃;
●可选地被一个或多个直链或支链烷基基团取代的环烷烃;
●半角鲨烷(或2,6,10-三甲基十二烷;CAS号:3891-98-3)、角鲨烷(或2,6,10,15,19,23-六甲基二十四烷)、氢化聚异丁烯或氢化聚癸烯。
植物油优选选自属于以下家族的油:
●具有式(IV)的亲脂性酯,
其中R2-(C=O)-表包含8至24个碳原子的饱和或不饱和的、直链或支链的酰基,并且R3独立于R2表示包含1至24个碳原子的饱和或不饱和的、直链或支链的烃基链,具有式(IV)的化合物表示例如月桂酸甲酯、月桂酸乙酯、月桂酸丙酯、月桂酸异丙酯、月桂酸丁酯、月桂酸2-丁酯、月桂酸己酯、椰油酸甲酯、椰油酸乙酯、椰油酸丙酯、椰油酸异丙酯、椰油酸丁酯、椰油酸2-丁酯、椰油酸己酯、椰油酸辛酯、椰油酸癸酯、椰油酸辛酯和癸酯、肉豆蔻酸甲酯、肉豆蔻酸乙酯、肉豆蔻酸丙酯、肉豆蔻酸异丙酯、肉豆蔻酸丁酯、肉豆蔻酸2-丁酯、肉豆蔻酸己酯、肉豆蔻酸辛酯、棕榈酸甲酯、棕榈酸乙酯、棕榈酸丙酯、棕榈酸异丙酯、棕榈酸丁酯、棕榈酸2-丁酯、棕榈酸己酯、棕榈酸辛酯、油酸甲酯、油酸乙酯、油酸丙酯、油酸异丙酯、油酸丁酯、油酸2-丁酯、油酸己酯、油酸辛酯、硬脂酸甲酯、硬脂酸乙酯、硬脂酸丙酯、硬脂酸异丙酯、硬脂酸丁酯、硬脂酸2-丁酯、硬脂酸己酯、硬脂酸辛酯、异硬脂酸甲酯、异硬脂酸乙酯、异硬脂酸丙酯、异硬脂酸异丙酯、异硬脂酸丁酯、异硬脂酸2-丁酯、异硬脂酸己酯、异硬脂酸异硬脂酯;
根据特定方面,具有式(IV)的化合物表示椰油酰基辛酸酯癸酸酯,如以商标名DUB810C出售的产品,椰油酸丙酯、椰油酸异丙酯、棕榈酸丙酯、棕榈酸异丙酯、棕榈酸辛酯。
●具有式(V)的甘油三酯
其中R4-(C=O)、R5-(C=O)和R6-(C=O),可以相同或不同,表示含有8至24个碳原子的直链或支链、饱和或不饱和的酰基,更特别是选自由以下组成的组的要素的酰基:辛酰基、癸酰基、十二烷酰基、十四烷酰基、十六烷酰基、十八烷酰基、二十烷酰基、二十二烷酰基、油烯基、亚油烯基、亚麻酰基或异硬脂酰基。
术语“油(H2)”意指如先前所定义的油(H1),并且更特别是如上所述的矿物油和具有式(V)的化合物,其中R4-(C=O),R5-(C=O)和R6-(C=O)可以相同或不同,表示选自由辛酰基、癸酰基和十二烷酰基组成的组的要素的酰基。
本发明的主题还是包含如先前所定义的组合物(C)的局部用配制品(F)。换言之,局部用配制品(F)包含组合物(C)和至少一种油(H2)的混合物。
在如上定义的配制品(F)的定义中使用的表述“局部使用”意指制备所述配制品以允许其施用于皮肤、头发、头皮或粘膜,无论它是在化妆品、皮肤化妆品、皮肤药物或药物组合物的情况下的直接施用,还是例如在呈纺织品或纸擦拭物形式的身体卫生产品或旨在与皮肤或粘膜接触的卫生产品的情况下的间接施用。
优选地,该局部用配制品(F)将是化妆品配制品。
所述局部用配制品(F)通常是呈油性组合物的形式,呈悬浮液、乳液、微乳液或纳米乳液的形式,无论它们具有油包水、水包油、水包油包水还是油包水包油类型。
所述局部用配制品(F)可以被包装在瓶中、泵瓶类型的装置中、以加压形式在气溶胶装置中、配备有穿孔壁(如格栅)的装置中或配备有球涂抹器(被称为滚抹器)的装置中。
一般而言,所述局部用组合物(F)还包含在用于局部使用的配制品(特别是化妆品、皮肤用化妆品、药物或皮肤药物配制品)领域中通常使用的赋形剂和/或活性成分,如增稠和/或胶凝表面活性剂、稳定剂、成膜化合物、水溶助剂、增塑剂、乳化剂和共乳化剂、遮光剂、珠光剂、富脂剂、多价螯合剂、螯合剂、抗氧化剂、香料、防腐剂、调理剂、旨在用于漂白体毛和皮肤的漂白剂、旨在提供关于皮肤或毛发的处理作用的活性成分、防晒剂、颜料或矿物填料、提供视觉效果或旨在用于包封活性成分的颗粒、去角质颗粒或质地剂。
如先前描述的组合物(C)和油(H2)的混合物将优选在50℃与85℃之间的温度下、更优选在80℃的温度下制备。然后将获得的均匀油性组合物冷却至在15℃与30℃之间的室温。
油(H2)的增稠最终通过测量动态粘度值通过量化粘性或胶凝液体稠度来进行视觉评估。
为了使组合物(C)被认为是有效的,必须至少实现粘性或胶凝的方面。
本发明的主题还是一种用于制备根据本发明的增稠共聚物组合物(C)的方法,该方法包括:
a)生产衣康酸单酯和/或低聚酯的组合物(C0),其包含由呈游离酸形式或部分或完全盐化形式的具有式(AIId1)、(IIf1)和(IIg1)的化合物组成的组中的至少一种要素和由呈游离酸形式或部分或完全盐化形式的具有式(IIa1)、(IIb1)、(IIc1)、(IIc1’)、(IIe1)和(IIh1)的化合物组成的组中的至少一种要素;
b)制备步骤a)中生产的该组合物(C0)与油(H1)的混合物(M1),
c)通过将热自由基引发剂引入在步骤b)结束时获得的所述混合物(M1)中引发混合物(M1)的共聚,以及
d)回收组合物(C)。
如先前所定义的方法的步骤c)中的术语“热引发剂”表示这样的分子:当将其置于所述结构特定的温度下时,通过至少一个共价键的均裂产生至少两个自由基,所述自由基使得能够引发自由基聚合。
根据特定方面,热引发剂选自由以下组成的组的要素:过氧化月桂酰、偶氮双(异丁腈)或AIBN、过氧化苯甲酰或BPO、偶氮双((2-甲基丁腈)或AMBN、4,4’-偶氮双(4-氰基戊酸)或ACVA、2,2’-偶氮双(2,4-二甲基戊腈)、枯烯氢过氧化物、二叔丁基过氧化物或叔丁基氢过氧化物。
用于制备增稠组合物(C)的方法将优选包括以下特征中的一个或多个:
-该方法包括去除组合物(C)中包含的油(H1)中的至少一些的步骤。这允许获得更浓缩的组合物(C),
-聚合在40℃与80℃之间的温度下进行,
-在步骤b)中添加交联单体(AR),
-交联单体是二烯或多烯交联单体,尤其是选自乙二醇二甲基丙烯酸酯、二乙二醇二丙烯酸酯、乙二醇二丙烯酸酯、二烯丙基脲、三烯丙基胺、三羟甲基丙烷三丙烯酸酯和亚甲基双(丙烯酰胺),
-生产衣康酸单酯和/或低聚酯的组合物(C0)的步骤a)包括以下子步骤:
i)将生物基醇或多元醇引入反应器中,该生物基醇或多元醇选自由以下呈液体形式的化合物组成的组的要素:
·具有以下结构的低聚甘油:
其中m表示大于或等于2并且小于或等于10的整数,
·具有以下结构的天然多元醇:
其中o表示等于2(赤藓糖醇)、或等于3(木糖醇)、或等于4(山梨糖醇)的数字,
·具有以下结构的脱水天然多元醇:
其中X表示氢原子(赤藓糖醇)、或基团-CH2-OH(木糖醇)或基团-CH(OH)-CH2-OH(山梨糖醇),
·具有以下结构的脂肪族脂肪醇:
R1-OH (IId)
其中R1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的烃基脂肪族基团。
根据特定方面,R1表示选自正己基、正庚基、正辛基、正癸基、正十二烷基、正十四烷基、正十六烷基、正十八烷基、油烯基、亚油烯基、亚麻烯基、花生基、山嵛基、瓢儿菜基和12-羟基硬脂基基团的烃基脂肪族基团,
·具有下式(IIe)的α,ω-二醇:
其中q表示大于或等于1并且小于或等于12的整数,
·具有下式(IIf)的化合物:
其中R’1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的烃基脂肪族基团。
根据特定方面,R’1表示选自正己基、正庚基、正辛基、正癸基、正十二烷基、正十四烷基、正十六烷基、正十八烷基、油烯基、亚油烯基、亚麻烯基、花生基、山嵛基、瓢儿菜基和12-羟基硬脂基基团的烃基脂肪族基团。
更特别地,具有式(IIf)的化合物是鲨肝醇,其结构如下:
·具有下式(IIg)的化合物:
其中R’1-C(=O)表示包含12至24个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且更特别地是选自由以下组成的组的要素的基团:十二烷酰基、十四烷酰基、十六烷酰基、十八烷酰基、二十烷酰基、二十二烷酰基、油烯基、亚油烯基、亚麻酰基或异硬脂酰基,并且其中x表示大于或等于1并且小于或等于5的自然整数;更特别地,具有式(IIg)的化合物是具有下式的单硬脂酸甘油酯;
以及
·具有下式(IIh)的化合物:
其中R’1-C(=O)表示包含12至36个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且更特别地是选自由以下组成的组的要素的基团:十二烷酰基、十四烷酰基、十六烷酰基、十八烷酰基、二十烷酰基、二十二烷酰基、油烯基、亚油烯基、亚麻酰基或异硬脂酰基,并且其中x表示大于或等于6并且小于或等于20的自然整数;更特别地,具有式(IIh)的化合物是聚甘油-6月桂酸酯,其结构如下:
ii)然后在机械搅拌下将衣康酸(I)、聚合抑制剂和酯化催化剂添加至该反应器中,
iii)在分压下将该反应器中的该介质维持在120℃与180℃之间的温度,以进行酯化反应,以及
iv)回收衣康酸单酯和/或低聚酯的组合物。
出于本发明的目的,术语“聚合抑制剂”表示当添加至单体中时,调节或迅速停止所述单体的不期望的聚合引发的化合物;在这些聚合抑制剂中,可以提及醌、氢醌、甲基氢醌、1,4-苯醌、2-叔丁基-1,4-苯醌、邻苯二酚(例如4-叔丁基邻苯二酚、2,6-二-叔丁基苯酚、6-叔丁基-2,4-二甲基苯酚、叔丁基氢醌、4-甲氧基苯酚、2,6-二-叔丁基-对甲酚)、芳香族硝基化合物(如硝基苯、硝基酚、硝基苯酚、亚硝基化合物、吩噻嗪、1,1-二苯基-2-苦基肼)和金属盐如铜盐,例如二丁基二硫代氨基甲酸铜(II),
-子步骤i)至iii)在120与180℃之间的温度下进行,
-子步骤iii)在500与20毫巴之间、并且更特别地在500与200毫巴之间的压力下进行,
-子步骤iii)持续在30分钟与10小时之间,
-在子步骤ii)中,该聚合抑制剂选自1,4-苯醌、2-叔丁基-1,4-苯醌、吩噻嗪、6-叔丁基-2,4-二甲基苯酚、二丁基二硫代氨基甲酸铜(II)、1,1-二苯基-2-苦基肼、2,6-二-叔丁基-对甲酚、4-叔丁基邻苯二酚、2,6-二-叔丁基苯酚、氢醌、叔丁基氢醌和4-甲氧基苯酚,
-在子步骤ii)中,该酯化催化剂是选自硫酸、盐酸、磷酸、硝酸、次磷酸、甲磺酸、对甲苯磺酸和三氟甲磺酸的酸以及酸性离子交换树脂。
化学计量摩尔比(IIa)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIb)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIc)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IId)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIe)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIf)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIg)/(I)大于或等于0.25并且小于或等于2.0。
化学计量摩尔比(IIh)/(I)大于或等于0.25并且小于或等于2.0。衣康酸单酯或低聚酯(A)的组合物通过测量宏观指数(酸值和酯值)和通过与具有内部校准的紫外(UV)检测器耦合的高效液相色谱(HPLC)测量的其残留的衣康酸含量来表征。
最后,确定衣康酸转化程度。必须实现大于或等于75%的转化程度,才能认为酯化反应已经正确进行。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的发泡和/或洗涤剂表面活性剂的实例包括阴离子、阳离子、两性或非离子的发泡和/或洗涤剂表面活性剂。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的发泡和/或洗涤剂阴离子表面活性剂包括烷基醚硫酸盐、烷基硫酸盐、烷基酰胺基醚硫酸盐、烷基芳基聚醚硫酸盐、单甘油酯硫酸盐、α-烯烃磺酸盐、链烷烃磺酸盐、烷基磷酸盐、烷基醚磷酸盐、烷基磺酸盐、烷基酰胺磺酸盐、烷基芳基磺酸盐、烷基羧酸盐、烷基磺基琥珀酸盐、烷基醚磺基琥珀酸盐、烷基酰胺磺基琥珀酸盐、烷基磺基乙酸盐、烷基肌氨酸盐、酰基羟乙基磺酸盐、N-酰基牛磺酸盐、酰基乳酸盐、N-酰基氨基酸衍生物、N-酰基肽衍生物、N-酰基蛋白质衍生物、N-酰基脂肪酸衍生物的碱金属盐、碱土金属盐、铵盐、胺盐或氨基醇盐。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的发泡和/或洗涤剂两性表面活性剂包括烷基甜菜碱、烷基酰胺基甜菜碱、磺基甜菜碱、烷基酰胺基烷基磺基甜菜碱、咪唑啉衍生物、磷酸酯甜菜碱、两性多乙酸盐和两性丙酸盐。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的发泡和/或洗涤剂阳离子表面活性剂特别地包括季铵衍生物。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的发泡和/或洗涤剂非离子表面活性剂更特别地包括包含含有8至16个碳原子的直链或支链的且饱和或不饱和的脂肪族基团的烷基聚糖苷,如辛基聚葡糖苷、癸基聚葡糖苷、十一烯基聚葡糖苷、十二烷基聚葡糖苷、十四烷基聚葡糖苷、十六烷基聚葡糖苷或1,12-十二烷二基聚葡糖苷;乙氧基化的氢化蓖麻油衍生物,如以INCI名称PEG-40氢化蓖麻油出售的产品;聚山梨醇酯,如聚山梨醇酯20、聚山梨醇酯40、聚山梨醇酯60、聚山梨醇酯70、聚山梨醇酯80或聚山梨醇酯85;椰仁酰胺;或N-烷基胺。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的增稠和/或胶凝表面活性剂的实例可选地包括烷氧基化的烷基聚糖苷脂肪酯,如乙氧基化的甲基聚葡糖苷酯,例如分别以名称GlucamateTMLT和GlucamateTMDOE-120出售的PEG 120甲基葡萄糖三油酸酯和PEG 120甲基葡萄糖二油酸酯;烷氧基化的脂肪酯,如以名称CrothixTMDS53出售的PEG 150季戊四醇四硬脂酸酯,或以名称AntilTM141出售的PEG 55丙二醇油酸酯;脂肪链聚亚烷基二醇氨基甲酸酯,如以名称ElfacosTMT211出售的PPG-14月桂醇聚醚异佛尔基二氨基甲酸酯,或以名称ElfacosTMGT2125出售的PPG-14棕榈油醇聚醚-60己基二氨基甲酸酯。
可以在所述组合物(F)中与如先前定义的所述增稠组合物(C)组合的增稠剂和/或胶凝剂的实例包括仅由单糖组成的多糖,如葡聚糖或葡萄糖均聚物、葡甘露聚糖葡聚糖、木葡聚糖、半乳甘露聚糖,其中主D-甘露糖链上的D-半乳糖单元的取代度(DS)是在0与1之间、并且更特别地在1与0.25之间,如来源于肉桂胶(DS=1/5)、刺槐豆胶(DS=1/4)、塔拉胶(DS=1/3)、瓜尔豆胶(DS=1/2)或葫芦巴胶(DS=1)的半乳甘露聚糖。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的增稠剂和/或胶凝剂的实例包括由单糖衍生物组成的多糖,如硫酸化的半乳聚糖且更特别地角叉菜胶和琼脂,乌龙糖(uronans)且更特别地褐藻胶、海藻酸盐和果胶,单糖和糖醛酸的杂聚物,且更特别地黄原胶、结冷胶、***胶渗出液和刺梧桐树胶渗出液、或葡糖胺聚糖。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的增稠剂和/或胶凝剂的实例包括纤维素,纤维素衍生物如甲基纤维素、乙基纤维素或羟丙基纤维素,硅酸盐,淀粉,亲水淀粉衍生物或聚氨酯。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的稳定剂的实例包括微晶蜡、且更特别地是地蜡,无机盐如氯化钠或氯化镁,或硅酮聚合物如聚硅氧烷聚烷基聚醚共聚物。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的溶剂的实例包括水,有机溶剂如甘油、双甘油、甘油低聚物、乙二醇、丙二醇、丁二醇、1,3-丙二醇、1,2-丙二醇、己二醇、二乙二醇、木糖醇、赤藓糖醇、山梨糖醇、水溶性醇(如乙醇、异丙醇或丁醇),或水和所述有机溶剂的混合物。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的温泉水或矿泉水的实例包括具有至少300mg/l的矿化度的温泉水或矿泉水,特别是雅漾(Avène)水、维泰尔(Vittel)水、维希盆地(Vichy basin)水、依泉(Uriage)水、理肤泉(La Roche-Posay)水、拉布尔布尔(La Bourboule)水、安亘湖(Enghien-les-Bains)水、圣泉薇莱班(Saint-Gervais-les-Bains)水、内里莱(Néris-les-Bains)水、阿勒瓦尔莱班(Allevard-les-Bains)水、迪涅(Digne)水、迈济耶(Maizières)水、Neyrac-les-Bains水、隆勒索涅(Lons-le-Saunier)水、罗什福尔(Rochefort)水、Saint Christau水、Les Fumades水和Tercis-les-Bains水。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的水溶助剂的实例包括二甲苯磺酸盐、枯烯磺酸盐、己基聚葡糖苷、2-乙基己基聚葡糖苷和正庚基聚葡糖苷。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的乳化表面活性剂的实例包括非离子表面活性剂、阴离子表面活性剂或阳离子表面活性剂。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的乳化非离子表面活性剂的实例包括山梨糖醇的脂肪酸酯,例如以名称MontaneTM40、MontaneTM60、MontaneTM70、MontaneTM80和MontaneTM85出售的产品;包含硬脂酸甘油酯和用在5mol与150mol之间的环氧乙烷乙氧基化的硬脂酸的组合物,例如包含用135mol环氧乙烷乙氧基化的硬脂酸和硬脂酸甘油酯的组合物(以名称SimulsolTM165出售);脱水甘露醇酯、乙氧基化的脱水甘露醇酯;蔗糖酯;甲基葡糖苷酯;包含直链或支链、饱和或不饱和的脂肪族基团并且包含14至36个碳原子的烷基聚糖苷,例如十四烷基聚葡萄糖苷、己基癸基聚葡萄糖苷、十八烷基聚葡萄糖苷、十六烷基聚木糖苷、十八烷基聚木糖苷、二十烷基聚葡萄糖苷、二十二烷基聚葡萄糖苷、2-辛基十二烷基聚木糖苷、12-羟基硬脂基聚葡萄糖苷;包含14至36个碳原子的直链或支链、饱和或不饱和的脂肪醇和如先前描述的烷基聚糖苷的组合物,例如以名称MontanovTM68、MontanovTM14、MontanovTM82、MontanovTM202、MontanovTMS、MontanovTMWO18、MontanovTML、FluidanovTM20X和EasynovTM出售的组合物。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的阴离子表面活性剂的实例包括甘油硬脂酸酯柠檬酸盐、鲸蜡硬脂基硫酸盐、皂如硬脂酸钠或硬脂酸三乙醇铵、和盐化的N-酰基氨基酸衍生物(例如硬脂酰谷氨酸盐)。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的阳离子乳化表面活性剂的实例包括氧化胺、季铵盐-82和在专利申请WO 96/00719中描述的表面活性剂并且主要是其脂肪链包含至少16个碳原子的那些。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的遮光剂和/或珠光剂的实例包括棕榈酸钠、硬脂酸钠、羟基硬脂酸钠、棕榈酸镁、硬脂酸镁、羟基硬脂酸镁、乙二醇单硬脂酸酯、乙二醇二硬脂酸酯、聚乙二醇单硬脂酸酯、聚乙二醇二硬脂酸酯、或包含12至22个碳原子的脂肪醇。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的质地剂的实例包括N-酰基氨基酸衍生物,如以名称AminohopeTMLL出售的月桂酰赖氨酸、以名称DryfloTM出售的辛烯基琥珀酸淀粉盐、以名称MontanovTM14出售的肉豆蔻基聚葡糖苷、纤维素纤维、棉纤维、壳聚糖纤维、滑石、绢云母或云母。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的除臭剂的实例包括碱金属硅酸盐,锌盐如硫酸锌、葡萄糖酸锌、氯化锌或乳酸锌;季铵盐,如鲸蜡基三甲基铵盐或鲸蜡基吡啶鎓盐;甘油衍生物,如甘油癸酸酯、甘油辛酸酯或聚甘油癸酸酯;1,2-癸二醇、1,3-丙二醇;水杨酸;碳酸氢钠;环糊精;金属沸石;TriclosanTM;水合溴化铝,水合氯化铝,氯化铝,硫酸铝,水合氯化铝锆,水合三氯化铝锆,水合四氯化铝锆,水合五氯化铝锆,水合八氯化铝锆,硫酸铝,乳酸钠铝,水合氯化铝和二醇的络合物,例如水合氯化铝和丙二醇的络合物,水合二氯化铝和丙二醇的络合物,倍半氯化羟基铝和丙二醇的络合物,水合氯化铝和聚乙二醇的络合物,水合二氯化铝和聚乙二醇的络合物,或倍半氯化羟基铝和聚乙二醇的络合物。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的蜡的实例包括蜂蜡、巴西棕榈蜡、小烛树蜡、小冠巴西棕蜡、日本蜡、软木纤维蜡、甘蔗蜡、石蜡、褐煤蜡、微晶蜡、羊毛脂蜡;地蜡、聚乙烯蜡、硅酮蜡、植物蜡、在室温下为固体的脂肪醇和脂肪酸,或在室温下为固体的甘油酯。在本专利申请中,术语“蜡”是指水不溶性的并且在大于或等于45℃的温度下具有固体外观的化合物和/或化合物的混合物。
可以在所述组合物(F)中与如上所定义的所述增稠组合物(C)组合的有效成分的实例包括维生素及其衍生物、特别是其酯,如视黄醇(维生素A)及其酯(例如棕榈酸视黄醇酯)、抗坏血酸(维生素C)及其酯、抗坏血酸的糖衍生物(如抗坏血酸基葡糖苷)、生育酚(维生素E)及其酯(如生育酚乙酸酯)、维生素B3或B10(烟酰胺及其衍生物);对皮肤显示美白或脱色素作用的化合物,如以名称SepiwhiteTMMSH、SepicalmTMVG出售的ω-十一碳烯酰基苯丙氨酸,ω-十一碳烯酰基苯丙氨酸的甘油单酯和/或甘油二酯,ω-十一碳烯酰基二肽,熊果苷,曲酸,氢醌;显示镇静作用的化合物,尤其是SepicalmTMS、尿囊素和甜没药醇;抗炎剂;显示保湿作用的化合物,如脲、羟基脲、甘油、聚甘油、甘油葡糖苷、二甘油葡糖苷、聚甘油葡糖苷、木糖醇葡糖苷;富含多酚的植物提取物,如葡萄提取物、松树提取物、葡萄酒提取物或橄榄提取物;显示减肥或解脂作用的化合物,如咖啡因或其衍生物、AdiposlimTM、AdipolessTM、岩藻黄质;N-酰基蛋白质;N-酰基肽,如MatrixylTM;N-酰基氨基酸;N-酰基蛋白质的部分水解产物;氨基酸;肽;蛋白的总水解产物;大豆提取物,例如RaffermineTM;小麦提取物,例如TensineTM或GliadineTM;植物提取物,如富含丹宁酸的植物提取物、富含异黄酮的植物提取物或富含萜的植物提取物;淡水藻或海藻的提取物;海洋植物提取物;海洋提取物,通常如珊瑚;精华蜡(essential wax);细菌提取物;神经酰胺;磷脂;显示抗微生物作用或净化作用的化合物,如LipacideTMC8G、LipacideTMUG、SepicontrolTMA5、OctopiroxTM或SensivaTMSC50;显示激励或刺激特性的化合物,如PhysiogenylTM、泛醇及其衍生物,如SepicapTMMP;抗老化活性剂,如SepiliftTMDPHP、LipacideTMPVB、SepivinolTM、SepivitalTM、ManolivaTM、Phyto-AgeTM、TimecodeTM;SurvicodeTM;抗光老化活性剂;保护真皮表皮交界处的完整性的活性剂;增加细胞外基质组分的合成的活性剂,如胶原、弹性蛋白或糖胺聚糖;在化学细胞通信上顺利地作用的活性剂,如细胞因子,或在物理细胞通信上顺利地作用的活性剂,如整合素;在皮肤上产生“变暖”感觉的活性剂,如皮肤微循环激活剂(如烟酸衍生物)或在皮肤上产生“新鲜”感觉的产品(如薄荷醇和衍生物);改善皮肤微循环的活性剂,例如静脉张力剂(venotonics);排水活性剂;具有减充血目的的活性剂,如银杏(Ginkgobiloba)、常春藤、马栗树、竹、假叶树属(Ruscus)、金雀花(butcher’s broom)、积雪草(Centella asiatica)、石衣藻属(fucus)、迷迭香或柳树提取物;用于晒黑或致黑皮肤的试剂,例如二羟基丙酮(DHA),赤藓酮糖,内消旋酒石醛,戊二醛,甘油醛,阿脲(alloxan)或茚三酮,植物提取物,例如紫檀属和鸡血檀(Baphia)属的红木提取物,如檀香紫檀(Pterocarpus santalinus)、非洲紫檀(Pterocarpus osun)、绍氏紫檀(Pterocarpussoyauxii)、刺猬紫檀(Pterocarpus erinaceus)、印度紫檀(Pterocarpus indicus)或非洲小叶紫檀(Baphia nitida),如在欧洲专利申请EP 0 971 683中描述的那些;以其促进和/或加速人体皮肤晒黑或致黑的作用和/或以其着色人体皮肤的作用已知的试剂,例如类胡萝卜素(并且更特别地是β-胡萝卜素和γ-胡萝卜素)),由宝芸达公司(Provital)以商标名“胡萝卜油(Carros Oil)”(INCI名称:胡萝卜(Daucus carrota),向日葵(Helianthusannuus)葵花籽油)出售的产品,其含有类胡萝卜素、维生素E和维生素K;以其在与暴露于紫外辐射组合时加速人体皮肤晒黑的作用已知的酪氨酸和/或其衍生物,例如由宝芸达公司以商标名SunTan AcceleratorTM出售的含有酪氨酸和核黄素(维生素B)的产品,由ZymoLine公司以商标名Zymo Tan Complex出售的酪氨酸和酪氨酸酶的络合物,由米百乐公司(Mibelle)以商标名MelanoBronzeTM(INCI名称:乙酰酪氨酸,僧侣的胡椒提取物(穗花牡荆(Vitex Agnus-castus)))出售的含有乙酰酪氨酸的产品,由Unipex公司以商标名Unipertan VEG-24/242/2002(INCI名称:丁二醇和乙酰酪氨酸以及水解植物蛋白和三磷酸腺苷)出售的产品,由西达玛(Sederma)公司以商标名Try-ExcellTM(INCI名称:油酰酪氨酸和丝瓜(Luffa cylindrica)(籽)油和油酸)出售的产品,其含有西葫芦种子(或丝瓜油)的提取物,由奥尔本米乐公司(Alban Muller)以商标名ActibronzeTM(INCI名称:水解小麦蛋白和乙酰酪氨酸和葡萄糖酸铜)出售的产品,由Synerga公司以商标名TyrostanTM(INCI名称:己酰酪氨酸钾)出售的产品,由Synerga公司以商标名Tyrosinol(INCI名称:脱水山梨糖醇异硬脂酸酯、油酸甘油酯、己酰酪氨酸)出售的产品,由奥尔本米乐公司以商标名InstaBronzeTM(INCI名称:二羟基丙酮和乙酰酪氨酸和葡萄糖酸铜)出售的产品,由Exymol公司以商标名Tyrosilane(INCI名称:甲基硅烷醇和乙酰酪氨酸)出售的产品;已知其在活化黑素生成中的作用的肽,例如由Infinitec Activos公司以商标名Bronzing SF肽粉末(INCI名称:葡聚糖和八肽-5)出售的产品,以商标名Melitane(INCI名称:甘油和水和葡聚糖和乙酰六肽-1)出售的包含已知其α-MSH激动剂作用的乙酰六肽-1的产品,由利普泰公司(Lipotec)以商标名Melatimes SolutionsTM(INCI名称:丁二醇,棕榈酰三肽-40)出售的产品,糖和糖衍生物,例如由宝芸达公司(Provital)以商标名TanositolTM(INCI名称:肌醇)出售的产品,由CODIF International公司以商标名ThalitanTM(或PhycosaccharideTMAG)(INCI名称:水和水解藻胶(掌状海带(Laminaria digitata))和硫酸镁和硫酸锰),其含有海洋来源的寡糖(与镁和锰离子螯合的古罗糖醛酸和甘露糖醛酸),由奥尔本米乐公司以商标名MelactivaTM(INCI名称:麦芽糊精,刺毛黧豆(Mucuna pruriens)籽提取物)出售的产品,富含类黄酮的化合物,例如由茜莱博公司(Silab)以商标名Biotanning(INCI名称:水解甜橙果实提取物)出售并且已知富含柠檬类黄酮(橙皮苷类型)的产品;旨在用于处理头发和/或体毛的试剂,例如用于保护毛囊黑色素细胞的试剂,旨在保护所述黑色素细胞免受是所述黑色素细胞的衰老和/或凋亡的原因的细胞毒素剂,如选自在EP 1 515 688 A2号下公开的欧洲专利申请中所描述的那些的多巴色素互变异构酶活性的模拟物,合成的SOD模拟分子,例如锰络合物,抗氧化剂化合物,例如环糊精衍生物,来源于抗坏血酸、赖氨酸或精氨酸吡咯烷酮羧酸盐的含硅化合物,肉桂酸和维生素C的单酯和二酯的组合,以及更一般地是在EP 1 515 688 A2号下公开的欧洲专利申请中提到的那些。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的抗氧化剂的实例包括EDTA及其盐、柠檬酸、酒石酸、草酸、BHA(丁基化羟基苯甲醚)、BHT(丁基化羟基甲苯)、生育酚衍生物如生育酚乙酸酯、抗氧化剂化合物的混合物如由阿克苏诺贝尔公司(AkzoNobel)以INCI名称:谷氨酸二乙酸四钠出售的Dissolvine GL 47S。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的防晒剂的实例包括在修改的化妆品指令76/768/EEC,附件VII中出现的所有那些。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的有机防晒剂包括苯甲酸衍生物的家族,例如对氨基苯甲酸(PABA),尤其是PABA的单甘油酯、N,N25-丙氧基PABA的乙基酯、N,N-二乙氧基PABA的乙基酯、N,N-二甲基PABA的乙基酯、N,N-二甲基PABA的甲基酯和N,N-二甲基PABA的丁基酯;邻氨基苯甲酸衍生物的家族,例如N-乙酰基邻氨基苯甲酸三甲环己酯;水杨酸衍生物的家族,例如水杨酸戊酯、水杨酸三甲环己酯、水杨酸乙基己酯、水杨酸苯酯、水杨酸苄酯和水杨酸对异丙醇苯酯;肉桂酸衍生物的家族,例如肉桂酸乙基己酯、4-异丙基肉桂酸乙酯、2,5-二异丙基肉桂酸甲酯、肉桂酸对甲氧基丙酯、肉桂酸对甲氧基异丙酯、肉桂酸对甲氧基异戊酯、肉桂酸对甲氧基辛酯(肉桂酸对甲氧基-2-乙基己酯)、肉桂酸对甲氧基-2-乙氧基乙酯、肉桂酸对甲氧基环己酯、肉桂酸乙基-α-氰基-β-苯酯、肉桂酸2-乙基己基-α-氰基-β-苯酯或肉桂酸甘油基二-对甲氧基单-2-乙基己酰酯;二苯甲酮衍生物的家族,例如2,4-二羟基二苯甲酮、2,2'-二羟基-4-甲氧基二苯甲酮、2,2',4,4'-四羟基二苯甲酮、2-羟基-4-甲氧基二苯甲酮、2-羟基-4-甲氧基-4'-甲基二苯甲酮、2-羟基-4-甲氧基二苯甲酮-5-磺酸酯、4-苯基二苯甲酮、4'-苯基二苯甲酮-2-5-羧酸2-乙基己酯、2-羟基-4-正辛氧基二苯甲酮、4-羟基-3-羧基二苯甲酮;3-(4'-甲基亚苄基)-d,l-樟脑、3-(亚苄基)-d,l-樟脑、樟脑苯扎铵甲基硫酸酯;尿刊酸、尿刊酸乙酯;磺酸衍生物的家族,例如2-苯基苯并咪唑-5-磺酸及其盐;三嗪衍生物的家族,例如羟基苯基三嗪、乙基己氧基羟基苯基-4-甲氧基苯基三嗪、2,4,6-三苯胺基(对羰基(carbo)-2'-乙基己基-1'-氧基)-1,3,5-三嗪、4,4-((6-(((1,1-二甲基乙基)氨基)羰基)苯基)氨基)-1,3,5-三嗪-2,4-二基二亚氨基)双(2-乙基己基)苯甲酸酯、2-苯基-5-甲基苯并噁唑、2,2'-羟基-5-甲基苯基苯并***、2-(2'-羟基-5'-叔辛基苯基)苯并***、2-(2'-羟基-5'-甲基苯基)苯并***;二苯并吖嗪;二茴香酰甲烷(dianisoylmethane)、4-甲氧基-4”-叔丁基苯甲酰基甲烷;5-(3,3-二甲基-2-降冰片烯)-3-戊-2-酮;二苯基丙烯酸酯衍生物的家族,例如2-氰基-3,3-二苯基-2-丙烯酸2-乙基己酯、2-氰基-3,3-二苯基-2-丙烯酸乙酯;聚硅氧烷的家族,例如亚苄基硅氧烷丙二酸酯。
可以在所述组合物(F)中与如先前所定义的所述增稠组合物(C)组合的无机防晒剂(也称为“无机防晒霜”)包括氧化钛,氧化锌,氧化铈,氧化锆,黄色、红色或黑色氧化铁,或氧化铬。这些无机防晒霜可以或可以不进行微粉化,可以或可以不经受表面处理,并且可以可选地呈水性或油性预分散体的形式。
现在将借助于以下实例更详细描述本发明。
根据本发明的实例:
E.1-根据本发明的衣康酸单酯和/或低聚酯(A)的组合物的制备:
E.1.1-甘油基单硬脂酸酯衣康酸酯组合物(AIIg)的制备:
在135℃下在机械搅拌下将108.5g(1摩尔当量)的单硬脂酸甘油酯(IIgA)、39.6g(1摩尔当量)的衣康酸(I)和1000ppm(/反应介质)的4-甲氧基苯酚(或MEHQ)引入到反应器中。然后添加0.5%(/反应介质)的50%H3PO2的水溶液并且将反应介质放在约500毫巴的受控真空下。酯化反应开始(形成的水的蒸馏)并且持续6小时。6小时后,分离125.7g的甘油基单硬脂酸酯衣康酸酯组合物(AIIg),并且不经任何进一步的步骤按原样进行表征。
E.1.2-鲨肝醇衣康酸酯组合物(AIIf)的制备:
进行如段落E.1.1-中所描述的相同的程序,用50.3g(1摩尔当量)的鲨肝醇(IIf)和19.2g(1摩尔当量)的衣康酸(I)替代108.5g(1摩尔当量)的单硬脂酸甘油酯(IIgA)和39.6g(1摩尔当量)的衣康酸(I)。分离和表征61.2g的鲨肝醇衣康酸酯组合物(AIIf)。
E.1.3-硬脂醇衣康酸酯组合物(AIId17)的制备:
进行如段落E.1.1-中所描述的相同的程序,用74.0g(1摩尔当量)的硬脂醇(IId17)和35.9g(1摩尔当量)的衣康酸(I)替代108.5g(1摩尔当量)的单硬脂酸甘油酯(IIgA)和39.6g(1摩尔当量)的衣康酸(I)。分离并表征100.3g的硬脂醇衣康酸酯组合物(AIId17)。
E.1.4-聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)的制备:
进行如段落E.1.1-中所描述的相同的程序,用160.1g(1摩尔当量)的聚甘油-6月桂酸酯(IIhB)和32.3g(1摩尔当量)的衣康酸(I)替代108.5g(1摩尔当量)的单硬脂酸甘油酯(IIg)和39.6g(1摩尔当量)的衣康酸(I)。分离并表征XXX g的聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)。
E.1.5-由1-二十烷醇和1-二十二烷醇的混合物制备衣康酸酯组合物(AIId18):
使用如段落E.1.3-中所描述的相同的程序,用1摩尔当量的1-二十烷醇和1-二十二烷醇的等摩尔混合物替代1摩尔当量的硬脂醇。分离并表征107.0g的硬脂醇衣康酸酯组合物(AIId18)。
E.1.6-结果和结论:
所制备的所有组合物(A)的分析特征整理在下表1中。
表1
a)在内标物的存在下通过HPLC/UV确定,
b)转化程度=[1-((组合物(A)的质量x%(I)残留量)/起始时衣康酸的质量)]x100。
-表1-制备的衣康酸单酯和/或低聚酯组合物(A)的表征。
总体上,先前描述的酯化条件允许分离具有在100与350mg KOH/g之间的酯值的组合物(A),证明了酯化物质的显著形成。
在所有情况下,酸值大于0,范围在60与350mg KOH/g之间。这些值指示,不是衣康酸(I)的所有羧酸官能团都被酯化。
最终,由收集的组合物(A)的最终质量、该最终质量中含有的并且通过GC确定的残留的衣康酸(I)的百分比、以及还有最初使用的衣康酸(I)的质量计算的转化程度***地大于75%,表明酯化反应令人满意地进行。
E.2-根据本发明的聚(衣康酸酯)(P)的制备:
E.2.5-鲨肝醇衣康酸酯组合物(AIIf)和聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)在DUB 810C中共聚以获得组合物(C1):
将23.3g的组合物(AIIf)和4.3g的组合物(AIIh)溶解于反应器中的28.1g的DUB810C中。将溶液在约400rpm的搅拌下在50℃的温度下均化,然后用氮气鼓泡45min以便从介质中去除氧气。然后将介质加热至80℃的温度。然后添加110mg的过氧化月桂酰以引发聚合反应。介质变得更粘。2h后,然后引入55mg的过氧化月桂酰。再维持3h后,组合物(C1)呈现蜡状外观,并且在热的时候进行调节。
E.2.6-鲨肝醇衣康酸酯组合物(AIIf)和聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)在DUB 810C中共聚以获得组合物(C2):
进行如段落E.2.5-中所描述的相同的程序,将组合物(AIIf)的量从23.3减少到20.5g并且将组合物(AIIh)的量从4.3增加到8.3g。分离组合物(C2)。
E.2.7-甘油基单硬脂酸酯衣康酸酯组合物(AIIg)和聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)在IsoparTM M中共聚以获得组合物(C3):
进行如段落E.2.5-中所描述的相同的程序,用24.0g的组合物(AIIg)替代23.3g的组合物(AIIf)并且用28.1g的IsoparTM M替代28.1g的DUB 810C。
E.2.8-1-二十烷醇和1-二十二烷醇衣康酸酯组合物(AIId18)和聚甘油-6月桂酸酯衣康酸酯组合物(AIIh)在DUB 810C中共聚以获得组合物(C4):
进行如段落E.2.6-中所描述的相同的程序,用20.5g的组合物(AIId18)替代20.5g的组合物(AIIf)。分离组合物(C4)。
E.2.10-汇总表:
表2
-表2-聚合物(P)和制备的组合物(C)的表征。
E.3-组合物(C)的增稠特性的评价:
在80℃下,将0.7g的组合物(C1)至(C3)溶解于5g的两种不同的油(H2)中:PrimolTM352和EmogreenTM L19。将由此获得的溶液冷却至室温并且在25℃的温度下使用装配有合适的转子(M)的Brookfield(或BKF)LVT型粘度计并且以6rpm的速度(V6)对其增稠进行视觉评估和/或测量。
将在25℃下观察获得的结果整理在下表3中。
表3
++:粘稠度
+++:胶凝稠度
-表3-组合物(C)对油(H2)的增稠特性。
使用BKF粘度计,转子3,速度6rpm在25℃下进行粘度测量获得的结果整理在下表4中。
表4
通常,对于化学结构和极性不同的两种油(H2)都可观察到粘稠度或胶凝稠度。
通过在25℃下测量动态粘度来证实增稠,因为在该25℃的相同的温度下,PrimolTM352示出165mPa.s的粘度(BKF LVT M2V6),DUBTM810C示出10mPa.s的粘度(BKF LVTM2V6),并且EmogreenTML19示出小于或等于10mPa.s的粘度(BKF RVT M2V6)。
增稠的油(即(C1)至(C4))施用到皮肤后在所述皮肤上都没有示出任何滑动性或粘性或具有油腻的感觉(由具有适当资格且经过培训的评估人员的小组进行评估)。
这些实例示出根据本发明进行的方法有利地允许获得呈液体形式的胶凝剂,该胶凝剂含有通过衍生自植物来源的起始材料的单体的聚合获得的聚合物,该聚合物在油(H1)制备时立即可用,不同于现有技术的呈粉末形式的胶凝聚合物。
Claims (16)
1.一种用于增稠极性或非极性油(H2)的共聚物组合物(C),该共聚物组合物包含至少一种油(H1)和至少一种聚(衣康酸酯)(P),该至少一种聚(衣康酸酯)(P)由单体单元A和单体单元B组成,该单体单元A衍生自选自以下化合物组成的组的要素的单体:
·具有式(AIId1)
其中Y和Y’相同,表示基团R1O-;或Y和Y’不同,表示HO-基团或基团R1O-,其中R1表示含有6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的烃基脂肪族基团,
·具有式(IIf1)
其中Y6和Y’6相同,表示具有式(Y61)的基团;或Y和Y’不同,表示HO-基团或具有式(Y61)的基团:
其中R1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的脂肪族烃基基团,以及
·具有式(IIg1)
其中Y7和Y’7相同,表示具有式(Y71)的基团;或Y和Y’不同,表示HO-基团或具有式(Y71)的基团:
其中R’1-C(=O)表示包含12至24个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且其中x表示大于或等于1并且小于或等于5的自然整数,
并且
该单体单元B衍生自选自由以下化合物组成的组的要素的单体:
·具有式(IIa1)
其中Y1和Y’1可以相同或不同,表示HO-基团或具有式(Y11)的基团:
其中m是大于或等于2并且小于或等于10的整数;
·具有式(IIb1)
其中Y2和Y’2可以相同或不同,表示HO-基团或具有式(Y21)的基团:
其中o是大于或等于2并且小于或等于4的整数;
·具有式(IIc1)
其中Y3和Y’3可以相同或不同,表示HO-基团或具有式(Y31)的基团:
·具有式(IIc1’)
其中Y4和Y’4可以相同或不同,表示HO-基团或具有式(Y41)的基团:
·具有式(IIe1)
其中Y5和Y’5可以相同或不同,表示HO-基团或具有式(Y51)的基团:
O-(CH2)q-OH (Y51),
其中q是大于或等于1并且小于或等于12、更特别地大于或等于3并且小于或等于8的整数;以及
·具有式(IIh1)
其中Y8和Y’8可以相同或不同,表示HO-基团或具有式(Y81)的基团:
其中R’1-C(=O)表示包含12至36个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且其中x表示大于或等于6并且小于或等于20的自然整数。
2.如权利要求1所述的增稠共聚物组合物(C),其特征在于,其包含按质量计在20%与80%之间的油(H1)和按质量计在20%与80%之间的聚(衣康酸酯)(P)。
3.如权利要求1和2中任一项所述的增稠共聚物组合物(C),其特征在于,该油(H1)是在4℃与45℃之间、甚至更优选在15℃与45℃之间、并且甚至更优选在15℃与35℃之间的温度下呈液体形式的油。
4.如权利要求1至3中的一项所述的增稠共聚物组合物(C),其特征在于,该油H1是矿物油或植物来源的油、或这两种类型的油的混合物。
5.一种局部用配制品(F),其包含如权利要求1至4中的一项所定义的组合物(C)。
6.一种用于制备如权利要求1至4中的一项所定义的增稠共聚物组合物(C)的方法,该方法包括:
a)生产衣康酸单酯和/或低聚酯的组合物(C0),其包含由呈游离酸形式或部分或完全盐化形式的具有式(AIId1)、(IIf1)和(IIg1)的化合物组成的组中的至少一种要素和由呈游离酸形式或部分或完全盐化形式的具有式(IIa1)、(IIb1)、(IIc1)、(IIc1’)、(IIe1)和(IIh1)的化合物组成的组中的至少一种要素;
b)制备步骤a)中生产的该组合物(C0)与油(H1)的混合物(M1),
c)通过将热自由基引发剂引入在步骤b)结束时获得的所述混合物(M1)中引发该混合物(M1)的共聚,以及
d)回收组合物(C)。
7.如权利要求6所述的方法,其特征在于,其包括去除组合物(C)中包含的该油(H1)中的至少一些的步骤。
8.如权利要求6和7中任一项所述的方法,其特征在于,该聚合在40℃与80℃之间的温度下进行。
9.如权利要求6至8中的一项所述的方法,其特征在于,在步骤b)中,添加交联单体(AR)。
10.如权利要求9所述的方法,其特征在于,该交联单体(AR)是二烯或多烯交联单体,尤其是选自乙二醇二甲基丙烯酸酯、二乙二醇二丙烯酸酯、乙二醇二丙烯酸酯、二烯丙基脲、三烯丙基胺、三羟甲基丙烷三丙烯酸酯和亚甲基双(丙烯酰胺)。
11.如权利要求6至10中的一项所述的方法,其特征在于,生产该衣康酸单酯和/或低聚酯的组合物(C0)的步骤a)包括以下子步骤:
i)将生物基醇或多元醇引入反应器中,该生物基醇或多元醇选自由以下呈液体形式的化合物组成的组的要素:
-具有以下结构的低聚甘油:
其中m表示大于或等于2并且小于或等于10的整数,
-具有以下结构的天然多元醇:
其中o表示等于2(赤藓糖醇)、或等于3(木糖醇)、或等于4(山梨糖醇)的数字,
-具有以下结构的脱水天然多元醇:
其中X表示氢原子(赤藓糖醇)、或基团-CH2-OH(木糖醇)或基团-CH(OH)-CH2-OH(山梨糖醇),
-具有以下结构的脂肪族脂肪醇:
R1—OH(IId)
其中R1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的烃基脂肪族基团,
-具有下式(IIe)的α,ω-二醇:
其中q表示大于或等于1并且小于或等于12的整数,
-具有下式(IIf)的化合物:
其中R’1表示包含6至36个碳原子并且可选地被一个或多个羟基取代的直链或支链、饱和或不饱和的烃基脂肪族基团,
-具有下式(IIg)的化合物:
其中R’1-C(=O)表示包含12至24个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且x表示大于或等于1并且小于或等于5的整数,以及
-具有下式(IIh)的化合物:
其中R’1-C(=O)表示包含12至36个碳原子的直链或支链、饱和或不饱和的烃基酰基基团,并且x表示大于或等于6并且小于或等于20的自然整数,
ii)然后在机械搅拌下将衣康酸(I)、聚合抑制剂和酯化催化剂添加至该反应器中,
iii)在分压下将该反应器中的该介质维持在120℃与180℃之间的温度,以进行酯化反应,以及
iv)回收衣康酸单酯和/或低聚酯的组合物。
12.如权利要求11所述的方法,其特征在于,子步骤i)至iii)在120℃与180℃之间的温度下进行。
13.如权利要求11和12中任一项所述的方法,其特征在于,子步骤iii)在500与20毫巴之间、并且更特别地在500与200毫巴之间的压力下进行。
14.如权利要求11至13中的一项所述的方法,其特征在于,所述子步骤iii)持续在30分钟与10小时之间。
15.如权利要求11至14中的一项所述的方法,其特征在于,在子步骤ii)中,该聚合抑制剂选自1,4-苯醌、2-叔丁基-1,4-苯醌、吩噻嗪、6-叔丁基-2,4-二甲基苯酚、二丁基二硫代氨基甲酸铜(II)、1,1-二苯基-2-苦基肼、2,6-二-叔丁基-对甲酚、4-叔丁基邻苯二酚、2,6-二-叔丁基苯酚、氢醌、叔丁基氢醌和4-甲氧基苯酚。
16.如权利要求11至15中的一项所述的方法,其特征在于,在子步骤ii)中,该酯化催化剂是选自硫酸、盐酸、磷酸、硝酸、次磷酸、甲磺酸、对甲苯磺酸和三氟甲磺酸的酸以及酸性离子交换树脂。
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FRFR2106666 | 2021-06-23 | ||
PCT/EP2022/067062 WO2022268906A1 (fr) | 2021-06-23 | 2022-06-22 | Composition copolymérique épaississante d'huiles polaires ou apolaires, comprenant au moins une huile et au moins un poly(itaconate) |
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