CN111511714A - 脂氨基酸和二醇的新组合物,用于制备其的方法,以及由其产生的化妆品或药物组合物 - Google Patents
脂氨基酸和二醇的新组合物,用于制备其的方法,以及由其产生的化妆品或药物组合物 Download PDFInfo
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- CN111511714A CN111511714A CN201880083232.4A CN201880083232A CN111511714A CN 111511714 A CN111511714 A CN 111511714A CN 201880083232 A CN201880083232 A CN 201880083232A CN 111511714 A CN111511714 A CN 111511714A
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Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C233/00—Carboxylic acid amides
- C07C233/01—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms
- C07C233/45—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups
- C07C233/46—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom
- C07C233/47—Carboxylic acid amides having carbon atoms of carboxamide groups bound to hydrogen atoms or to acyclic carbon atoms having the nitrogen atom of at least one of the carboxamide groups bound to a carbon atom of a hydrocarbon radical substituted by carboxyl groups with the substituted hydrocarbon radical bound to the nitrogen atom of the carboxamide group by an acyclic carbon atom having the carbon atom of the carboxamide group bound to a hydrogen atom or to a carbon atom of an acyclic saturated carbon skeleton
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Abstract
披露了一种脂氨基酸和二醇的新组合物,一种用于制备其的方法,以及一种由其产生的化妆品或药物组合物。
Description
本发明涉及一种用于制备氨基酸、(寡)肽或部分或完全蛋白质水解产物的N-酰基衍生物的新颖方法,所述方法具有高的所用起始材料转化率。本发明还涉及获得的这些N-酰基化合物用于制备用于局部使用的化妆品或药物组合物或工业洗涤组合物的用途。
N-酰基氨基酸衍生物,也称为脂氨基酸(LAA),是阴离子表面活性剂,其由极性头和具有亲脂性的基于烃的链形成,所述极性头源自至少一种氨基酸的残基、或(寡)肽的残基或部分或完全蛋白质水解产物的残基,所述基于烃的链源自脂肪酰氯或脂肪酸甲酯,所述脂肪酰氯或脂肪酸甲酯本身衍生自油化学。
这些氨基酸、(寡)肽或部分或完全蛋白质水解产物的N-酰基衍生物通常首先作为有助于发泡和清洁特性的成分用于制备化妆品组合物例如像沐浴露或洗发剂,或者作为有助于生物学特性的成分用于制备化妆品组合物(其旨在防止或纠正难看的皮肤效应);所述生物学特性是例如抗衰老、瘦身、紧致、脱色素或促色素形成(pro-pigmenting)特性。
氨基酸、(寡)肽或部分或完全蛋白质水解产物的N-酰基衍生物通常通过在酰氯的存在下、在称为肖顿-鲍曼(Schotten-Baumann)条件的实验条件下一种或多种氨基酸的酰化来合成。
此方法例如在美国专利US 2 463 779和US 6 703 517中,在出版物J.Am.OilChem.Soc.[美国石油化学家协会杂志],78(1956),172中,以及在以编号WO 92/21318和WO94/26694公开的国际申请中披露。
此酰化方法包括将氨基酸盐化的先前步骤,随后是用酰氯酰化氨基酸盐的步骤,并且然后酸化所获得的N-酰基盐。
第一个步骤包括用无机碱中和预先溶解在水中或水和有机助溶剂的混合物中的氨基酸,所述无机碱通常是氢氧化钠水溶液或氢氧化钾水溶液。羧基然后呈离子化形式,因此使氨基酸更好地溶解在水中。此水溶液的pH是在9.0与12.0之间,这确保了氨基酸的胺官能团不被质子化。
第二个步骤是适当的酰化步骤。在此阶段,在环境温度下将酰氯逐渐添加到经中和的氨基酸溶液中。亲核胺官能团攻击羰基官能团的亲电子碳。这导致在两种起始底物之间形成酰胺键,并且还导致盐酸的形成。通过逐渐添加无机碱直接原位中和此酸(将pH调节至约10.0)。
在此阶段,酰氯水解以产生皂的副反应也是可能的。然而,必须将其最小化,以便实现氨基酸向其N-酰基衍生物的令人满意的转化并有效地分离它们,因为皂(或脂肪酸盐)的过高含量可能导致反应介质的相分离和/或气味或毒性问题(例如,对于C8和C'11酰基链)。
使得能够控制皂的形成的两个主要的反应参数是在反应阶段期间的搅拌速度(搅拌速度的优化使得可以改善氯化物与介质的接触表面积),以及在氨基酸的溶解步骤期间任选地添加酰化助溶剂,例如像丙酮、甲基乙基酮、异丙醇或二醇类。
此助溶剂添加使得可以改善酰氯对反应介质的亲和力。在此种情况下,必须机敏地选择酰化助溶剂,以便避免或最小化产生自此同一助溶剂与酰氯之间的反应的新副产物(例如像源自酯化副反应的副产物)的形成。
最后步骤包括完成步骤,以形成的N-酰基衍生物的形式提供,并且两种替代方案是可能的。
第一种包括将获得的反应介质的pH值调节到约7。N-酰基衍生物原样在溶液中分离,无需任何另外的纯化,并且包含酰化盐、未反应的氨基酸和任选的助溶剂。因此,它在水溶液中呈盐化形式,并且更精确地为羧酸盐形式,并且具有通常小于50%的纯度。
R1=氨基酸侧链,
R=椰油酰基链,
X=抗衡离子。
第二种包括通过将反应混合物酸化到2左右的pH值来沉淀N-酰基衍生物,并且然后进行若干次过滤和洗涤操作,以最终干燥所获得的介质结束。因此,此程序使得可以除去在酰化反应期间产生的所有盐、任选的酰化助溶剂和所有未反应的氨基酸。在这种情况下,N-酰基衍生物是呈具有羧酸官能团的非盐化形式,并且是呈固体形式,更特别是粉状形式,并且具有大于80%的纯度。
R1=氨基酸侧链,
R=椰油酰基链,
X=抗衡离子。
由于酰氯对亲核化合物和官能团(例如胺官能团)的非常高的反应性,以上描述的肖顿-鲍曼方法展现出在主要由水形成的溶剂介质中以高收率以快速动力学进行N-酰化反应而无需大量供应能量例如像热能的优点。
然而,现今,化妆品产品的配方人员面临关于当涉及制备成品时使用粉末的困难。而且,残留脂肪酸,其酰基基团含有小于12个碳原子,当它们以过大量存在时可能产生皮肤刺激反应和/或使人不愉快的气味,不适合用于制备化妆品组合物。因此,需要开发一种用于直接合成盐化的N-酰基氨基酸的高纯液体盐而没有沉淀/过滤/干燥阶段的方法。
诸位发明人发现,使用还可以用作最终稀释溶剂的酰化助溶剂可以实现此结果,应理解,此类助溶剂还必须使得能够在酰化步骤期间控制和/或最小化脂肪酸的形成、在反应条件下与酰氯具有差的反应性、允许在高温下通过简单的液/液倾析在酰化期间产生的盐的有效消除、以及最后使得能够获得具有中性pH的均匀的N-酰基氨基酸的溶液。
以公开号FR 2765105A2公开的法国专利申请描述了一种用于制备N-酰基氨基酸衍生物的混合物的方法,所述方法具体地使用不明确量的丙二醇(或1,2-丙二醇)、月桂酰氯,并且指示最终产物中的残留月桂酸含量是15质量%。
因此,根据第一方面,本发明的主题是一种组合物(C1),所述组合物每100%其质量包含:
(a)-大于或等于50质量%且小于或等于95质量%、更特别地大于或等于60质量%且小于或等于80质量%的质量比例的具有式(I)的化合物或具有式(I)的化合物的混合物:
X-[CH2]p-C(=O)-Y-OH (I),
其中p表示大于或等于5且小于或等于8的整数,Y表示或者具有式(IIa)的二价基团:
-[N(R3)-CH(R2)-C(=O)-]m- (IIa),
其中R3表示氢原子或甲基基团,m表示大于或等于1且小于或等于4的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基和3-氨丙基基团的基团;或者具有式(IIb)的二价基团:
其中R4表示氢原子或羟基基团,并且n表示大于或等于1且小于或等于4的整数;并且X表示或者甲基基团或者亚甲基基团(CH2=),或者具有式(III)的一价基团:
HO-Y’-C(=O)- (III),
其中Y’表示或者如前定义的具有式(IIa)的二价基团,或者如前定义的具有式(IIb)的二价基团,应理解,当X表示具有式(III)的基团时,Y和Y’是相同的;
(b)-大于0质量%且小于或等于15质量%、更特别地大于或等于5质量%且小于或等于10质量%的质量比例的包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇:
Ra 1-C(Rb 1)(OH)-C(OH)(Rc 1)(Rd 1) (IVa),
其中基团Ra 1、Rb 1、Rc 1和Rd 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,
Ra 1-C(Rb 1)(OH)-[C(Re 1)(Rf 1)]t-C(OH)(Rc 1)(Rd 1) (IVb),
其中t等于一、二或三,基团Ra 1、Rb 1、Rc 1、Rd 1、Re 1和Rf 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,应理解,基团Ra 1或Rb 1的至少一个和/或基团Rc 1或Rd 1的至少一个不表示氢原子;
(c)-大于或等于0质量%且小于或等于5质量%、更特别地大于或等于0.5质量%且小于或等于2.5质量%的质量比例的具有式(V)的化合物或具有式(V)的化合物的混合物:
X-[CH2]p-C(=O)-OH (V),
其中X表示甲基基团或乙烯基基团(CH2=CH-),p表示大于或等于5且小于或等于8的整数,或所述具有式(V)的化合物的混合物;以及
(d)-大于0质量%且小于50质量%、更特别地大于或等于10质量%且小于或等于25质量%的质量比例的水,
应理解,所述组合物的pH小于或等于3、更特别地小于或等于2.0。
根据一个具体方面,本发明的主题是如上定义的组合物(C1),其特征在于,在式(I)和(V)中,X表示甲基基团,根据此具体方面,在式(I)和(V)中,一价基团
X-(CH2)p-C(=O)更特别地表示选自庚酰基、辛酰基、癸酰基或10-十一碳烯酰基基团的基团。根据此更具体方面,如上定义的组合物(C1)最特别地特征在于,在式(I)中,二价基团Y表示具有式(IIa1)的二价基团:
-[NH-CH(R2)-C(=O)-]m- (IIa1),
其中m表示大于或等于一且小于或等于四的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基或3-氨丙基基团的基团;例如具有式(II’a1)的二价基团:
-NH-CH2-C(=O)- (II′a1),
如以上定义的组合物(C1),其特征在于,在式(I)和(V)中,一价基团X-(CH2)p-C(=O)-表示辛酰基基团。
根据另一个具体方面,如上定义的组合物(C1)的特征在于,在式(I)和(V)中,一价基团X-(CH2)p-C(=O)-表示10-十一碳烯酰基基团并且Y表示具有式(IIa2)的二价基团:
-[NH-CH(苄基)-C(=O)-]m- (IIa2),
表述“包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇”在如上定义的组合物(C1)中特别表示1,2-丙二醇、1,2-丁二醇、1,2-戊二醇、1,2-己二醇、1,2-辛二醇、1,3-丁二醇、2,3-丁二醇、2,3-戊二醇、2,3-己二醇、2,5-己二醇、或2-甲基2,4-戊二醇;并且更特别地1,2-丙二醇、1,2-丁二醇、1,3-丁二醇、1,2-戊二醇、1,2-己二醇、或2-甲基2,4-戊二醇。
本发明的主题还是一种用于制备如前定义的组合物(C1)的方法,其特征在于,所述方法包括以下连续步骤:
-步骤a),在此步骤期间,将所述包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇与水混合以形成混合物(S1),所述混合物每100%其质量包含从5质量%至70质量%、并且更特别地从5质量%至30质量%的所述具有式(IVa)或具有式(IVb)的邻二醇以及从30质量%至95质量%、并且更特别地从70质量%至95质量%的水;
-步骤b),在此步骤期间,将具有式(VIa):
或具有式(VIb)的化合物:
或具有式(VIa)或(VIb)的至少一种化合物与具有式(VIa)或(VIb)的至少另一种化合物的混合物以一定比例添加到所述混合物(S1)中使得所获得的混合物(M1)每100%其质量含有从5质量%至50质量%、更特别地从5质量%至30质量%的所述具有式(IVa)或(IVb)的化合物或所述具有式(VIa)和/或(VIb)的化合物的混合物,以及从50质量%至95质量%、更特别地从50质量%至70质量%的所述混合物(S1);
-步骤c),在此步骤期间,将氢氧化钠或氢氧化钾添加到所述混合物(M1)中以形成具有大于或等于9、更特别地大于或等于9.5的pH的混合物(M2);
-步骤d),在此步骤期间,将在0.7与1.0摩尔当量之间、更特别地在0.8与0.9摩尔当量之间的具有式(VII)的酰氯:
X-[CH2]p-C(=O)-Cl (VII),
其中X和p是如在上式(I)中所定义的,或具有式(VII)的酰氯的混合物倒入所述混合物(M2)中,同时通过联合添加氢氧化钠或氢氧化钾将所述pH维持在大于或等于9、更特别地大于或等于9.5的值,所述步骤e)导致形成混合物(M3);
-步骤e),在此步骤期间,将所述混合物(M3)酸化直至达到小于或等于3、更特别地小于或等于2.5的pH值;
-步骤f),出于排出母液目的的倾析;
-如果必要的话或如果需要的话,至少一个步骤g),在倾析之后用盐水洗涤以获得所述希望的组合物。
如上定义的方法的步骤a)通常是在环境温度下进行的。根据其具体方面,将所述包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇与水混合以形成混合物(S1),所述混合物每100%其质量包含从10质量%至20质量%的所述具有式(IVa)或具有式(IVb)的邻二醇和从80质量%至90质量%的水;
如上定义的方法的步骤b)通常是在环境温度下进行的。根据其具体方面,所述具有式(IVa)或式(IVb)的化合物,或所述具有式(IVa)或(IVb)的至少一种化合物与具有式(IVa)或(IVb)的至少另一种化合物的混合物以一定比例添加到所述混合物(S1)中使得所获得的混合物(M1)每100%其质量含有从10质量%至25质量%的所述具有式(IVa)或(IVb)的化合物或所述具有式(IVa)和/或(IVb)的化合物的混合物,以及从75质量%至90质量%的所述混合物(S1)。
如上定义的方法的步骤d)通常是通过以下方式进行的:将具有式(VII)的酰氯或具有式(VII)的酰氯的混合物逐渐倒入所述混合物(M2)中,同时将反应温度维持在10℃与40℃之间的范围;然后使反应在40℃与60℃之间的温度下进行约三十分钟。
如上定义的方法的步骤f)通常是通过将反应温度维持在40℃与60℃之间的范围进行的。
本发明的主题还是一种用于制备用于局部使用的化妆品、皮肤化妆品、皮肤药物或药物组合物(C)的方法,所述组合物包含:大于或等于5质量%且小于或等于30质量%的质量比例的具有式(I')的化合物或具有式(I')的化合物的混合物:
X-[CH2]p-C(=O)-Y-O-M+ (I’),
其中p表示大于或等于5且小于或等于8的整数,M+表示钠阳离子,Y表示或者具有式(IIa)的二价基团:
-[N(R3)-CH(R2)-C(=O)-]m- (IIa),
其中R3表示氢原子或甲基基团,m表示大于或等于1且小于或等于4的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基和3-氨丙基基团的基团;或者具有式(IIb)的二价基团:
其中R4表示氢原子或羟基基团,并且n表示大于或等于1且小于或等于4的整数;并且X表示或者甲基基团或者亚甲基基团(CH2=),或者具有式(III)的一价基团:
HO-Y’-C(=O)- (III),
其中Y’表示或者如上定义的具有式(IIa)的二价基团,或者如前定义的具有式(IIb)的二价基团,应理解,当X表示具有式(III)的基团时,Y和Y’是相同的;
(b)-大于5质量%且小于或等于30质量%的质量比例的包含从三至八个原子且或 者由式(IVa)或者由式(IVb)表示的二醇:
Ra 1-C(Rb 1)(OH)-C(OH)(Rc 1)(Rd 1) (IVa),
其中基团Ra 1、Rb 1、Rc 1和Rd 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,
Ra 1-C(Rb 1)(OH)-[C(Re 1)(Rf 1)]t-C(OH)(Rc 1)(Rd 1) (IVb),
其中t等于一、二或三,基团Ra 1、Rb 1、Rc 1、Rd 1、Re 1和Rf 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,应理解,基团Ra 1或Rb 1的至少一个和基团Rc 1或Rd 1的至少一个不表示氢原子;
(d)-大于40质量%且小于90质量%的质量比例的水,
应理解,所述组合物(C)的pH小于或等于9且大于或等于5.5,
所述方法的特征在于所述方法包括步骤h),在此步骤期间,将必要量的具有式(IVa)或具有式(IVb)的二醇、氢氧化钠水溶液和水同时或依次添加到如权利要求1至7中任一项所述的组合物(C1)中,直至达到如上定义的比例和pH值。
在通过如上定义的方法获得的用于局部使用的所述化妆品、皮肤化妆品、皮肤药物或药物组合物(C)的定义中使用的表述“用于局部使用”意指所述组合物通过施用于皮肤、头发、头皮或黏膜使用,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黏膜接触的卫生产品的情况下的间接施用。
通过如上定义的方法获得的用于局部使用的化妆品、皮肤化妆品、皮肤药物或药物组合物(C)可以以加压形式包装在气溶胶装置中或“泵动式喷涂”类型的装置中、包装在配备有穿孔壁的装置(例如格栅)中、或包装在配备有球涂抹器的装置(称为“滚抹器”)中。当将其包装在小瓶子中时,所述组合物(C)可以借助于机械加压装置或推进剂气体装置以细小液滴的形式施用。在可以与根据本发明的组合物(C)组合的推进剂之中的是氢氟化合物,例如二氯二氟甲烷、三氯氟甲烷、二氟乙烷、异丁烷、丁烷和丙烷。
通过如上定义的方法获得的所述组合物(C)还可以包含在用于局部使用的制剂(特别是化妆品、皮肤化妆品、药物或皮肤药物制剂)领域中通常使用的赋形剂和/或活性成分。
此类赋形剂例如是发泡和/或洗涤剂表面活性剂、增稠和/或胶凝表面活性剂、增稠剂和/或胶凝剂、稳定剂、成膜化合物、溶剂和助溶剂、水溶助剂、增塑剂、遮光剂、珠光剂、多价螯合剂、螯合剂、抗氧化剂、香料、精油、防腐剂、调节剂、提供视觉效果或旨在包封活性剂的颗粒、去角质颗粒、质地剂、光学增白剂。
此类活性成分例如旨在为皮肤或头发提供处理和/或保护作用,如防晒剂、矿物填料或颜料、驱虫剂、除臭剂或旨在漂白体毛和皮肤的漂白剂。
在可以包括在所述组合物(C)中的水溶性抗氧化剂之中的是例如抗坏血酸、谷胱甘肽、酒石酸、草酸和谷氨酸二乙酸四钠。
在可以包括在所述组合物(C)中的水溶性多价螯合剂之中的是例如乙二胺四乙酸(EDTA)盐,例如EDTA的钠盐,二乙烯三胺五乙酸(DTPA)盐,例如DTPA的钠盐,以及乙酰基谷氨酸(Dissolvine系列)。
在可以包括在所述组合物(C)中的水溶性染料之中的是例如焦糖、黄5、酸性蓝9/蓝1、绿5、绿3/固绿FCF 3、橙4、红4/食品红1、黄6、酸性红33/食品红12、红40、胭脂虫红(CI15850,CI 75470)、外用紫2、红6-7、普鲁士蓝、群青、酸性黄3/黄10、酸性蓝3、黄10。
在可以包括在所述组合物(C)中的稳定颜色的水溶性剂之中的是例如三(四甲基羟基哌啶醇)柠檬酸盐、苯并三唑基丁苯酚磺酸钠或苯并三唑基十二烷基对甲酚。
作为任选地存在于所述组合物(C)中的发泡和/或洗涤剂表面活性剂的实例,可以提及在本活性领域中通常使用的局部可接受的阴离子、阳离子、两性或非离子的发泡和/或洗涤剂表面活性剂。
在可以包括在所述组合物(C)中的发泡和/或洗涤剂阴离子表面活性剂之中的是例如烷基醚硫酸盐、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-酰基蛋白质衍生物以及脂肪酸的碱金属盐、碱土金属盐、铵盐、胺盐、氨基醇盐。
在任选地存在于所述组合物(C)中的发泡和/或洗涤剂两性表面活性剂之中,可以提及烷基甜菜碱、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、磷酸甜菜碱、两性聚乙酸盐和两性丙酸盐。
在任选地存在于所述组合物(C)中的发泡和/或洗涤剂阳离子表面活性剂之中,特别地可以提及季铵衍生物。
在任选地存在于所述组合物(C)中的发泡和/或洗涤剂非离子表面活性剂之中,更特别地可以提及含有直链或支链的、饱和或不饱和的脂肪族基团并且含有从八至十二个碳原子的烷基聚糖苷;蓖麻油衍生物、聚山梨醇酯、椰仁酰胺和N-烷基胺。
作为任选地存在于所述组合物(C)中的质地剂的实例,可以提及N-酰基氨基酸衍生物,例如在名称AminohopeTM LL下出售的月桂酰赖氨酸、在名称DryfloTM下出售的辛烯基淀粉琥珀酸盐、在名称Montanov 14下出售的肉豆蔻基聚葡萄糖苷、纤维素纤维、棉纤维、壳聚糖纤维、滑石、绢云母、云母和珍珠岩。
任选地存在于所述组合物(C)中的活性成分的实例包括:
-维生素及其衍生物,例如视黄醇(维生素A)和其酯(例如棕榈酸视黄酯)、呈其盐形式和酯的抗坏血酸(维生素C)、抗坏血酸的糖衍生物(如抗坏血酸葡糖苷)、生育酚(维生素E)及其酯(例如生育酚乙酸酯)、维生素B3或B10(烟酰胺及其衍生物);-对皮肤有增亮或脱色素作用的化合物,例如SepiwhiteTM MSH、熊果苷、曲酸、氢醌、VegewhiteTM、GatulineTM、SynerlightTM、BiowhiteTM、PhytolightTM、DermalightTM、ClariskinTM、MelaslowTM、DermawhiteTM、Ethioline、MelarestTM、GigawhiteTM、AlbatineTM和LumiskinTM;
-具有镇静作用的化合物,如SepicalmTM S、尿囊素和没药醇;
-抗炎剂;
-具有保湿作用的化合物,例如二甘油,三甘油,脲,羟基脲,甘油基葡萄糖苷,二甘油基葡萄糖苷,聚甘油葡萄糖苷,赤藓醇葡萄糖苷,山梨醇葡萄糖苷,木糖醇葡萄糖苷,包含木糖醇葡萄糖苷、脱水木糖醇和木糖醇的以商标名AquaxylTM出售的组合物;
-具有减肥或分解脂肪作用的化合物,如咖啡因或其衍生物、AdiposlimTM和AdipolessTM;
-富含丹宁酸、多酚和/或异黄酮的植物提取物,例如葡萄提取物、松树提取物、葡萄酒提取物、橄榄提取物;大豆提取物,例如RaffermineTM;小麦提取物,例如TensineTM或GliadineTM;富含萜烯的植物提取物;淡水或海水藻类提取物;海洋提取物,通常例如珊瑚;
-具有抗微生物作用或具有净化作用的化合物,例如LipacideTM C8G、LipacideTMUG、SepicontrolTM A5;OctopiroxTM或SensivaTM SC50;
-具有活肤或刺激特性的化合物,如PhysiogenylTM、泛醇以及其衍生物如SepicapTM MP;
-抗老化活性剂,如SepiliftTM DPHP、LipacideTM PVB、SepivinolTM、SepivitalTM、ManolivaTM、Phyto-AgeTM、TimecodeTM;SurvicodeTM;
-抗光老化活性剂;
-增加细胞外基质组分的合成的活性剂,例如胶原、弹性蛋白和糖胺聚糖;
-在化学细胞通信上有利地作用的活性剂,如细胞因子,或在物理细胞通信上有利地作用的活性剂,如整合素;
-在皮肤上产生“加热”感觉的活性剂,例如皮肤毛细管循环活化剂(例如烟酸衍生物)或在皮肤上产生“清凉”感觉的产品(例如薄荷醇和其衍生物);
-改善皮肤毛细血管循环的活性剂,例如静脉紧张剂(venotonic agent);排水活性剂;减充血活性剂,例如银杏、常春藤、马栗树、竹、花竹柏(ruscus)、金雀花(butcher’sbroom)、积雪草、岩藻、迷迭香或柳树的提取物;
-充当皮肤绷紧剂的活性剂,例如植物蛋白质水解产物,海洋来源的水解产物,例如海带提取物的水解产物,鱼类软骨水解产物,海洋弹性蛋白,由赛比克公司(SEPPIC)以商标名SesaflashTM出售的产品,或胶原蛋白溶液;
-皮肤晒黑剂或褐变剂,例如二羟基丙酮、靛红、阿脲、茚三酮、甘油醛、内消旋酒石醛、戊二醛或赤藓酮糖。
作为任选地存在于所述组合物(C)中的除臭剂的实例,可以提及碱金属硅酸盐,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,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。
作为任选地存在于所述组合物(C)中的增稠剂或胶凝剂的实例,可以提及直链或支链的或交联的聚电解质类型的聚合物,如部分或完全成盐的丙烯酸均聚物,部分或完全成盐的甲基丙烯酸均聚物,部分或完全成盐的2-甲基-[(1-氧代-2-丙烯基)氨基]-1-丙磺酸(AMPS)均聚物,丙烯酸和AMPS的共聚物,丙烯酰胺和AMPS的共聚物,乙烯基吡咯烷酮和AMPS的共聚物,AMPS和(2-羟乙基)丙烯酸酯的共聚物,AMPS和(2-羟乙基)甲基丙烯酸酯的共聚物,AMPS和羟乙基丙烯酰胺的共聚物,AMPS和N,N-二甲基丙烯酰胺的共聚物,AMPS和三(羟甲基)丙烯酰胺基甲烷(THAM)的共聚物,丙烯酸或甲基丙烯酸和(2-羟乙基)丙烯酸酯的共聚物,丙烯酸或甲基丙烯酸和(2-羟乙基)甲基丙烯酸酯的共聚物,丙烯酸或甲基丙烯酸和羟乙基丙烯酰胺的共聚物,丙烯酸或甲基丙烯酸和THAM的共聚物,丙烯酸或甲基丙烯酸和N,N-二甲基丙烯酰胺的共聚物,丙烯酸或甲基丙烯酸、AMPS和(2-羟乙基)丙烯酸酯的三元共聚物,丙烯酸或甲基丙烯酸、AMPS和(2-羟乙基)甲基丙烯酸酯的三元共聚物,丙烯酸或甲基丙烯酸、AMPS和THAM的三元共聚物,丙烯酸或甲基丙烯酸、AMPS和N,N-二甲基丙烯酰胺的三元共聚物,丙烯酸或甲基丙烯酸、AMPS和丙烯酰胺的三元共聚物,丙烯酸或甲基丙烯酸和丙烯酸烷基酯的共聚物(其碳链包含在四与三十个之间的碳原子并且更特别地在十与三十个之间的碳原子),AMPS和丙烯酸烷基酯的共聚物(其碳链包含在四与三十个之间的碳原子并且更特别地在十与三十个之间的碳原子),至少一种具有游离的部分成盐或完全成盐的强酸官能团的单体与至少一种中性单体和至少一种具有式(VIII)的单体的直链、支链或交联的三元共聚物:
CH2=C(R’3)-C(=O)-[CH2-CH2-O]n-R’4 (VIII)
其中R’3表示氢原子或甲基基团,R'4表示含有从八至三十个碳原子的直链或支链的烷基基团,并且n表示大于或等于一且小于或等于五十的数。
可以包括在所述组合物(C)中的聚电解质型的直链或支链或交联的聚合物可以呈溶液、水性悬浮液、油包水乳液、水包油乳液、粉末的形式存在,例如在以下名称下出售的产品:SimuleTM EG、SimulgelTM EPG、SepigelTM 305、SimulgelTM 600、SimulgelTM NS、SimulgelTM INS 100、SimulgelTM FL、SimulgelTM A、SimulgelTM SMS 88、SepinovTM EMT10、SepiplusTM 400、SepiplusTM 265、SepiplusTM S、SepimaxTM Zen、AristoflexTM AVC、AristoflexTM AVS、NovemerTM EC-1、NovemerTM EC 2、AristoflexTM HMB、CosmediaTM SP、FlocareTM ET 25、FlocareTM ET 75、FlocareTM ET 26、FlocareTM ET 30、FlocareTM ET 58、FlocareTM PSD 30、ViscolamTM AT 64以及ViscolamTM AT 100;仅由糖构成的多糖,例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D-甘露糖主链上的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,例如源自肉桂胶(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;由糖衍生物构成的多糖,例如半乳聚糖硫酸盐并且更特别是角叉菜胶和琼脂,乌龙糖(uronans)并且更特别是褐藻胶、海藻酸盐和果胶,糖和糖醛酸的杂聚物,并且更特别是黄原胶、结冷胶、阿拉伯树胶挤出物和刺梧桐树胶挤出物、葡萄糖胺聚糖;纤维素,纤维素衍生物例如甲基纤维素、乙基纤维素、羟丙基纤维素、硅酸盐、淀粉、亲水淀粉衍生物、聚氨酯。
作为可以存在于所述组合物(C)中的油的实例,可以提及矿物油,如液体石蜡、液体凡士林、异链烷烃或白矿物油;动物来源的油例如角鲨烯或角鲨烷;植物油,如角鲨烷、甜杏仁油、椰仁油、蓖麻油、霍霍巴油、橄榄油、菜籽油、花生油、向日葵油、小麦胚芽油、玉米胚芽油、大豆油、棉籽油、苜蓿油、罂粟油、南瓜油、月见草油、小米油、大麦油、黑麦油、红花油、桐树油、西番莲油、榛子油、棕榈油、乳木果油、杏仁油、芫荽籽油、山毛榉实果油、横经席叶油、大蒜芥油、鳄梨油、金盏花油,衍生自花或蔬菜的油;乙氧基化的植物油;合成油,例如脂肪酸酯,如肉豆蔻酸丁酯,肉豆蔻酸丙酯,肉豆蔻酸异丙酯、肉豆蔻酸鲸蜡酯,棕榈酸异丙酯,棕榈酸辛酯,硬脂酸丁酯,硬脂酸十六烷基酯,硬脂酸异丙酯,硬脂酸辛酯,硬脂酸异鲸蜡酯,油酸十二烷基酯,月桂酸己酯,二辛酸丙二醇酯,衍生自羊毛脂酸的酯类(如羊毛脂酸异丙酯、羊毛脂酸异鲸蜡酯),脂肪酸单甘油酯、二甘油酯和三甘油酯(例如三庚酸甘油酯),苯甲酸烷基酯,氢化油,聚(α-烯烃),聚烯烃(如聚(异丁烷)),合成的异烷烃(例如异十六烷、异十二烷),全氟化油;硅酮油,例如二甲基聚硅氧烷、甲基苯基聚硅氧烷、用胺改性的硅酮、用脂肪酸改性的硅酮、用醇改性的硅酮、用醇和脂肪酸改性的硅酮、用聚醚基团改性的硅酮、环氧基改性的硅酮、用氟基团改性的硅酮、环状硅酮以及用烷基改性的硅酮。在本专利申请中,术语“油”是指水不溶性的并且在25℃的温度下具有液体外观的化合物和/或化合物的混合物。
作为任选地存在于所述组合物(C)中的蜡的实例,可以提及蜂蜡、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;在环境温度下是固体的脂肪醇和脂肪酸;在环境温度下是固体的甘油酯。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。
作为可以包括在所述组合物(C)中的乳化非离子表面活性剂的实例,可以提及山梨醇的脂肪酸酯,例如在名称MontaneTM 40、MontaneTM 60、MontaneTM 70、MontaneTM 80和MontaneTM 85下出售的产品;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(在名称SimulsolTM 165下出售);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;含有直链或支链、饱和或不饱和的脂肪族基团,含有从14至36个碳原子的烷基聚糖苷,例如十四烷基聚葡糖苷、十六烷基聚葡糖苷、十八烷基聚葡糖苷、十六烷基聚木糖苷、十八烷基聚木糖苷、二十烷基聚葡糖苷、二十二烷基(dodecosyl)聚葡糖苷、(2-辛基十二烷基)聚木糖苷、(12-羟基硬脂基)聚葡糖苷;含有从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前描述的烷基聚糖苷的组合物,例如以商标名MontanovTM 68、MontanovTM 14、MontanovTM 82、MontanovTM 202、MontanovTM S、MontanovTM WO18、MontanovTM L、FluidanovTM 20X和EasynovTM出售的组合物。
作为任选地存在于所述组合物(C)中的用于防护太阳紫外线辐射的试剂的实例,指出了颜料、有机防晒剂和无机防晒剂。
作为任选地存在于所述组合物(C)中的用作用于防护太阳紫外线辐射的试剂的颜料,例如有二氧化钛、棕色氧化铁、黄色氧化铁、黑色氧化铁或红色氧化铁、或者白色或有色珠光颜料,如钛云母。
作为任选地存在于所述组合物(C)中的用作用于防护太阳紫外线辐射的试剂的有机防晒剂,例如有:
-苯甲酸衍生物家族的那些,例如对-氨基苯甲酸(PABA),尤其是PABA的单甘油酯、N,N-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、N,N-二甲基PABA的丁基酯;
-邻氨基苯甲酸衍生物家族的那些,例如N-乙酰基邻氨基苯甲酸三甲环己酯;
-水杨酸衍生物家族的那些,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、水杨酸对异丙醇苯基酯;
-肉桂酸衍生物的家族的那些,例如肉桂酸乙基己酯、肉桂酸乙基-4-异丙酯、肉桂酸甲基-2,5-二异丙酯、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、肉桂酸甘油基二-对-甲氧基-单-2-乙基己酰酯;
-二苯甲酮衍生物家族的那些,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、2-乙基己基-4'-苯基二苯甲酮-2-羧酸酯、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盐;尿刊酸、尿刊酸乙酯;
-磺酸衍生物家族的那些,如2-苯基苯并咪唑-5-磺酸及其盐;三嗪衍生物家族,如羟苯基三嗪、乙基己氧基羟苯基-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、苯甲酸的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)酯、2-苯基-5-甲基苯并噁唑、2,2'-羟基-5-甲基苯基苯并三唑、2-(2'-羟基-5'-叔辛基苯基)苯并三唑、2-(2'-羟基-5'-甲基苯基)苯并三唑;二苯并氮卓(dibenzazine);二茴香酰基甲烷、4-甲氧基-4”-叔丁基苯甲酰基甲烷;5-(3,3-二甲基-2-亚降冰片基)-3-戊-2-酮;2-(4-二乙基氨基-2-羟基苯甲酰基)苯甲酸己基酯、2,4-双{[4-(2-乙基己氧基)-2-羟基]苯基}-6-(4-甲氧基苯基)-1,3,5-三嗪、2,4,6-三[4-(2-乙基己氧基羰基)苯胺基]-1,3,5-三嗪、2-乙基己基二甲氧基亚苄基二氧代咪唑烷丙酸酯、二苯基丙烯酸酯衍生物的家族,如2-乙基己基-2-氰基-3,3-二苯基-2-丙烯酸酯或乙基-2-氰基-3,3-二苯基-2-丙烯酸酯;
-聚硅氧烷家族的那些,如亚苄基硅氧烷丙二酸酯。
作为任选地存在于所述组合物(C)中的用作用于防护太阳紫外线辐射的试剂的无机防晒剂,例如有氧化钛、氧化锌、氧化铈、氧化锆、黄色、红色或黑色氧化铁、氧化铬。这些矿物防晒剂可以进行或可以不进行微粉化,可以经历或可以不经历表面处理并且可以任选地呈水性或油性预分散体的形式存在。
以下实例阐明本发明,然而不限制本发明。
根据本发明的组合物(C1)的制备
通用程序如下:
组合物(C1)的特征整理在下表1中:
对比组合物(C21)的制备
如此获得的组合物(C21)的特征整理在下表2中。
对比组合物(C22)的制备
在环境温度和机械搅拌下,将20质量%的甘氨酸、L-天冬氨酸、L-谷氨酸和L-丙氨酸的混合物以基于100质量%的所述氨基酸的混合物10%/35%/45%/10%的甘氨酸/L-天冬氨酸/L-谷氨酸/L-丙氨酸的质量比例引入到80质量%的水/二醇(按质量计85/15)的混合物中,
(C<sub>1A</sub>) | (C<sub>1B</sub>) | (C<sub>1C</sub>) | |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>) | 2-甲基-2,4-戊二醇 | 1,2-丙二醇 | 1,3-丙二醇 |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>)的含量 | 8.9质量% | 1.2质量% | 1.1质量% |
辛酸(V)的含量 | 0.8质量% | 2.2质量% | 3.9质量% |
水含量 | 19.0质量% | 19.8质量% | 16.0质量% |
N-辛酰甘氨酸(I)的含量 | 71.3质量% | 76.8质量% | 78.5质量% |
副产物的存在 | 否 | 否 | 0.5质量% |
组合物的pH | pH=1.8 | pH=2.0 | pH=1.9 |
(C<sub>1D</sub>) | (C<sub>1E</sub>) | (C<sub>1F</sub>) | |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>) | 1,2-丁二醇 | 1,3-丁二醇 | 1,4-丁二醇 |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>)的含量 | 8.1质量% | 3.8质量% | 0.9质量% |
辛酸(V)的含量 | 0.6质量% | 2.4质量% | 3.0质量% |
水含量 | 19.1质量% | 20.2质量% | 23.0质量% |
N-辛酰甘氨酸(I)的含量 | 72.2质量% | 73.6质量% | 71.9质量% |
副产物的存在 | 否 | 否 | 1.2质量% |
组合物的pH | pH=1.6 | pH=1.5 | pH=1.7 |
(C<sub>1G</sub>) | (C<sub>1H</sub>) | (C<sub>1I</sub>) | |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>) | 1,2-戊二醇 | 1,5-戊二醇 | 1,2-己二醇 |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>)的含量 | 6.6质量% | 2.2质量% | 10.1质量% |
辛酸(V)的含量 | 0.8质量% | 2.9质量% | 0.6质量% |
水含量 | 19.0质量% | 18.5质量% | 16.2质量% |
N-辛酰甘氨酸(I)的含量 | 73.6质量% | 74.6质量% | 73.1质量% |
副产物的存在 | 否 | 1.8质量% | 否 |
组合物的pH | pH=1.8 | pH=2.1 | pH=2.2 |
表1
(C<sub>21</sub>) | (C<sub>22</sub>) | |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>) | 1,2-丙二醇 | 1,2-丙二醇 |
二醇(IV<sub>a</sub>)或(IV<sub>b</sub>)的含量 | 0.9质量% | 1.9质量% |
月桂酸(V)的含量 | 4.1质量% | 12.9质量% |
水含量 | 11.0质量% | 27.5质量% |
N-月桂酰甘氨酸(I)的含量 | 83.2质量% | 11.9质量% |
N-月桂酰丙氨酸(I)的含量 | - | 11.0质量% |
N-月桂酰天冬氨酸(I)的含量 | - | 12.2质量% |
N-月桂酰谷氨酸(I)的含量 | - | 20.4质量% |
副产物的存在 | 0.8质量% | 2.2质量% |
组合物的pH | pH=2.1 | pH=2.2 |
表2
不像组合物(C1C)、(C1F)、(C21)和(C22),为本发明主题的组合物(C1A)、(C1B)和(C1D)、(C1E)和(C1G)的分析揭示了它们不含有副产物,并且它们的脂肪酸浓度比组合物(C1C)、(C1H)、(C1F)、(C21)和(C22)的脂肪酸浓度更低。
Claims (10)
1.一种组合物(C1),每100%其质量包含:
(a)-大于或等于50质量%且小于或等于95质量%的质量比例的具有式(I)的化合物或具有式(I)的化合物的混合物:
X-[CH2]p-C(=O)-Y-OH (I),
其中p表示大于或等于5且小于或等于8的整数,Y表示或者具有式(IIa)的二价基团:
-[N(R3)-CH(R2)-C(=O)-]m- (IIa),
其中R3表示氢原子或甲基基团,m表示大于或等于1且小于或等于4的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基和3-氨丙基基团的基团;或者具有式(IIb)的二价基团:
其中R4表示氢原子或羟基基团,并且n表示大于或等于1且小于或等于4的整数;并且X表示或者甲基基团或者亚甲基基团(CH2=),或者具有式(III)的一价基团:
HO-Y’-C(=O)- (III),
其中Y’表示或者如前定义的所述具有式(IIa)的二价基团,或者如前定义的所述具有式(IIb)的二价基团,应理解,当X表示所述具有式(III)的基团时,Y和Y’是相同的;
(b)-大于0质量%且小于或等于15质量%的质量比例的包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇:
Ra 1-C(Rb 1)(OH)-C(OH)(Rc 1)(Rd 1) (IVa),
其中基团Ra 1、Rb 1、Rc 1和Rd 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,
Ra 1-C(Rb 1)(OH)-[C(Re 1)(Rf 1)]t-C(OH)(Rc 1)(Rd 1) (IVb),
其中t等于一、二或三,基团Ra 1、Rb 1、Rc 1、Rd 1、Re 1和Rf 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,应理解,基团Ra 1或Rb 1的至少一个和/或基团Rc 1或Rd 1的至少一个不表示氢原子;
(c)-大于或等于0质量%且小于或等于5质量%的质量比例的具有式(V)的化合物或具有式(V)的化合物的混合物:
X-[CH2]p-C(=O)-OH (V),
其中X表示甲基基团或乙烯基基团(CH2=CH-),p表示大于或等于5且小于或等于8的整数,或所述具有式(V)的化合物的混合物;以及
(d)-大于0质量%且小于50质量%的质量比例的水,
应理解,所述组合物的pH小于或等于3。
2.如权利要求1所述的组合物(C1),其特征在于,在式(I)和(V)中,X表示甲基基团。
3.如权利要求2所述的组合物(C1),其特征在于,在式(I)中,所述二价基团Y表示具有式(IIa1)的二价基团:
-[NH-CH(R2)-C(=O)-]m- (IIa1),
其中m表示大于或等于一且小于或等于四的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基或3-氨丙基基团的基团。
4.如权利要求3所述的组合物(C1),其特征在于,在式(I)中,所述二价基团Y表示具有式(II’a1)的二价基团:
-NH-CH2-C(=O)- (II’a1)。
5.如权利要求4所述的组合物(C1),其特征在于,在式(I)和(V)中,所述一价基团X-(CH2)p-C(=O)-表示辛酰基基团。
6.如权利要求2所述的组合物(C1),其特征在于,在式(I)和(V)中,所述一价基团X-(CH2)p-C(=O)-表示10-十一碳烯酰基基团并且Y表示具有式(IIa2)的二价基团:
-[NH-CH(苄基)-C(=O)-]m- (IIa2)。
7.如权利要求1至6中任一项所述的组合物(C1),其特征在于,所述包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇选自1,2-丙二醇、1,2-丁二醇、1,3-丁二醇、1,2-戊二醇、1,2-己二醇、1,2-辛二醇、2,3-丁二醇、2,3-戊二醇、2,3-己二醇、2,5-己二醇或2-甲基-2,4-戊二醇。
8.如权利要求7所述的组合物(C1),其特征在于,所述包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇选自1,2-丙二醇、1,2-丁二醇、1,3-丁二醇、1,2-戊二醇、1,2-己二醇或2-甲基-2,4-戊二醇。
9.一种用于制备如权利要求1至8中任一项所述的组合物(C1)的方法,其特征在于,所述方法包括以下连续步骤:
-步骤a),在此步骤期间,将所述包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇与水混合以形成混合物(S1),所述混合物每100%其质量包含从5质量%至70质量%的所述具有式(IVa)或具有式(IVb)的二醇和从30质量%至95质量%的水;
-步骤b),在此步骤期间,将具有式(VIa):
或具有式(VIb)的化合物:
或具有式(VIa)或(VIb)的至少一种化合物与具有式(VIa)或(VIb)的至少另一种化合物的混合物以一定比例添加到所述混合物(S1)中使得所获得的混合物(M1)每100%其质量含有从5质量%至50质量%的所述具有式(VIa)或(VIb)的化合物或所述具有式(VIa)和/或(VIb)的化合物的混合物,以及从50质量%至95质量%的所述混合物(S1);
-步骤c),在此步骤期间,将氢氧化钠或氢氧化钾添加到所述混合物(M1)中以形成具有大于或等于9的pH的混合物(M2);
-步骤d),在此步骤期间,将具有式(VII)的酰氯:
X-[CH2]p-C(=O)-Cl (VII),
其中X和p是如在上式(I)中所定义的,或具有式(VII)的酰氯的混合物倒入所述混合物(M2)中,同时通过联合添加氢氧化钠或氢氧化钾将所述pH维持在大于或等于9的值,所述步骤e)导致形成混合物(M3);
-步骤e),在此步骤期间,将所述混合物(M3)酸化直至达到小于或等于3的pH值;
-步骤f),出于排出母液目的的倾析;
-如果必要的话或如果需要的话,至少一个步骤g),在倾析之后用盐水洗涤以获得所述希望的组合物。
10.一种用于制备用于局部使用的化妆品、皮肤化妆品、皮肤药物或药物组合物(C)的方法,所述组合物包含:大于或等于5质量%且小于或等于30质量%的质量比例的具有式(I')的化合物或具有式(I')的化合物的混合物:
X-[CH2]p-C(=O)-Y-O-M+ (I’),
其中X表示甲基基团或乙烯基基团(CH2=CH-),p表示大于或等于5且小于或等于12的整数,M+表示钠阳离子,Y表示或者具有式(IIa)的二价基团:
-[N(R3)-CH(R2)-C(=O)-]m- (IIa),
其中R3表示氢原子或甲基基团,m表示大于或等于1且小于或等于4的整数,并且R2表示氢原子或选自甲基、异丙基、异丁基、1-甲基丙基、苄基和3-氨丙基基团的基团;或者具有式(IIb)的二价基团:
其中R4表示氢原子或羟基基团,并且n表示大于或等于1且小于或等于4的整数;并且X表示或者甲基基团或者亚甲基基团(CH2=),或者具有式(III)的一价基团:
HO-Y’-C(=O)- (III),
其中Y’表示或者如上定义的所述具有式(IIa)的二价基团,或者如上定义的所述具有式(IIb)的二价基团,应理解,当X表示所述具有式(III)的基团时,Y和Y’是相同的;
(b)-大于5质量%且小于或等于30质量%的质量比例的包含从三至八个原子且或者由式(IVa)或者由式(IVb)表示的二醇:
Ra 1-C(Rb 1)(OH)-C(OH)(Rc 1)(Rd 1) (IVa),
其中基团Ra 1、Rb 1、Rc 1和Rd 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,
Ra 1-C(Rb 1)(OH)-[C(Re 1)(Rf 1)]t-C(OH)(Rc 1)(Rd 1) (IVb),
其中t等于一、二或三,基团Ra 1、Rb 1、Rc 1、Rd 1、Re 1和Rf 1的每一个彼此独立地表示氢原子或含有从一至五个碳原子的饱和脂肪族基团,应理解,基团Ra 1或Rb 1的至少一个和基团Rc 1或Rd 1的至少一个不表示氢原子;
(d)-大于40质量%且小于90质量%的质量比例的水,
应理解,所述组合物(C)的pH小于或等于9且大于或等于5.5,
所述方法的特征在于所述方法包括步骤h),在此步骤期间,将必要量的具有式(IVa)或具有式(Vb)的二醇、氢氧化钠水溶液和水同时或依次添加到如权利要求1至8中任一项所述的组合物(C1)中,直至达到如上定义的比例和pH值。
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FR1762585A FR3075197B1 (fr) | 2017-12-20 | 2017-12-20 | Nouvelle composition de lipoaminoacides et de diols, le procede pour leur preparation et composition cosmetique ou pharmaceutique en resultant |
FR1762585 | 2017-12-20 | ||
PCT/FR2018/053213 WO2019122601A1 (fr) | 2017-12-20 | 2018-12-12 | Nouvelle composition de lipoaminoacides et de diols, le procédé pour leur préparation et composition cosmétique ou pharmaceutique en résultant |
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JP (1) | JP7361035B2 (zh) |
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EP0415598A1 (en) * | 1989-08-16 | 1991-03-06 | Unilever Plc | Cosmetic composition |
FR2765105A1 (fr) * | 1997-06-25 | 1998-12-31 | Seppic Sa | Composition comprenant un lipoaminoacide et du gluconate de zinc et utilisation en cosmetique |
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FR2826265B1 (fr) * | 2001-06-26 | 2005-02-18 | Oreal | Composition cosmetique ou dermatologique comprenant une association entre un inhibiteur de l'elastase de la famille des n-acylaminoamides et au moins un agent antifongique et/ou antibacterien |
US6703517B2 (en) | 2001-11-26 | 2004-03-09 | Ajinomoto Co., Inc. | Method for preparing N-long chain acyl neutral amino acid |
JP2003221371A (ja) | 2001-11-26 | 2003-08-05 | Ajinomoto Co Inc | N−長鎖アシル中性アミノ酸の製造方法 |
US20130101530A1 (en) * | 2011-10-25 | 2013-04-25 | Galaxy Surfactants Ltd. | Antimicrobial preservative compositions for personal care products |
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2017
- 2017-12-20 FR FR1762585A patent/FR3075197B1/fr active Active
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- 2018-12-12 CN CN201880083232.4A patent/CN111511714B/zh active Active
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- 2018-12-12 US US16/956,420 patent/US20210093533A1/en not_active Abandoned
- 2018-12-12 EP EP18833922.0A patent/EP3728182B1/fr active Active
- 2018-12-12 WO PCT/FR2018/053213 patent/WO2019122601A1/fr unknown
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EP0415598A1 (en) * | 1989-08-16 | 1991-03-06 | Unilever Plc | Cosmetic composition |
FR2765105A1 (fr) * | 1997-06-25 | 1998-12-31 | Seppic Sa | Composition comprenant un lipoaminoacide et du gluconate de zinc et utilisation en cosmetique |
FR2771632A1 (fr) * | 1997-12-01 | 1999-06-04 | Seppic Sa | Composition synergique comprenant au moins un lipoaminoacide et au moins un glycol; application en cosmetique |
JP2002212031A (ja) * | 2001-01-16 | 2002-07-31 | Noevir Co Ltd | クレンジング組成物 |
US20140056953A1 (en) * | 2011-04-14 | 2014-02-27 | Novo Nordisk A/S | Fatty acid acylated amino acids for oral peptide delivery |
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WO2017153161A1 (de) * | 2016-03-08 | 2017-09-14 | Minasolve Germany Gmbh | Wässrige lösungen von n-acyl-aminosäuren |
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JP7361035B2 (ja) | 2023-10-13 |
EP3728182B1 (fr) | 2024-04-17 |
WO2019122601A1 (fr) | 2019-06-27 |
FR3075197A1 (fr) | 2019-06-21 |
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