CN110872454B - 含有碱性染料和氨基酸的化合物、染发用染料以及染发用组合物 - Google Patents
含有碱性染料和氨基酸的化合物、染发用染料以及染发用组合物 Download PDFInfo
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- CN110872454B CN110872454B CN201910814409.XA CN201910814409A CN110872454B CN 110872454 B CN110872454 B CN 110872454B CN 201910814409 A CN201910814409 A CN 201910814409A CN 110872454 B CN110872454 B CN 110872454B
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- 239000000981 basic dye Substances 0.000 title abstract description 21
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 86
- 239000000126 substance Substances 0.000 claims abstract description 32
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- -1 alkylene carbonate Chemical compound 0.000 claims description 72
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- 235000014113 dietary fatty acids Nutrition 0.000 claims description 9
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- 229930195712 glutamate Natural products 0.000 description 6
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- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 4
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- 229910052801 chlorine Inorganic materials 0.000 description 3
- 125000001309 chloro group Chemical group Cl* 0.000 description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 3
- 238000011156 evaluation Methods 0.000 description 3
- 229910052731 fluorine Inorganic materials 0.000 description 3
- 125000001153 fluoro group Chemical group F* 0.000 description 3
- IPSIPYMEZZPCPY-UHFFFAOYSA-N new fuchsin Chemical compound [Cl-].C1=CC(=[NH2+])C(C)=CC1=C(C=1C=C(C)C(N)=CC=1)C1=CC=C(N)C(C)=C1 IPSIPYMEZZPCPY-UHFFFAOYSA-N 0.000 description 3
- 230000003287 optical effect Effects 0.000 description 3
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- CMXXUDSWGMGYLZ-XRIGFGBMSA-N (2s)-2-amino-3-(1h-imidazol-5-yl)propanoic acid;hydron;chloride;hydrate Chemical compound O.Cl.OC(=O)[C@@H](N)CC1=CN=CN1 CMXXUDSWGMGYLZ-XRIGFGBMSA-N 0.000 description 2
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- SVTBMSDMJJWYQN-UHFFFAOYSA-N 2-methylpentane-2,4-diol Chemical compound CC(O)CC(C)(C)O SVTBMSDMJJWYQN-UHFFFAOYSA-N 0.000 description 2
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- 239000010452 phosphate Substances 0.000 description 1
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- ABLZXFCXXLZCGV-UHFFFAOYSA-N phosphonic acid group Chemical group P(O)(O)=O ABLZXFCXXLZCGV-UHFFFAOYSA-N 0.000 description 1
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- NJGBTKGETPDVIK-UHFFFAOYSA-N raspberry ketone Chemical compound CC(=O)CCC1=CC=C(O)C=C1 NJGBTKGETPDVIK-UHFFFAOYSA-N 0.000 description 1
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- 229940043267 rhodamine b Drugs 0.000 description 1
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- 239000011734 sodium Substances 0.000 description 1
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- 239000000661 sodium alginate Substances 0.000 description 1
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- 229940074545 sodium dihydrogen phosphate dihydrate Drugs 0.000 description 1
- KMPHTYSTEHXSTL-UHFFFAOYSA-M sodium;2-hydroxypropanoate;2-hydroxypropanoic acid Chemical compound [Na+].CC(O)C(O)=O.CC(O)C([O-])=O KMPHTYSTEHXSTL-UHFFFAOYSA-M 0.000 description 1
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- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000005580 triphenylene group Chemical group 0.000 description 1
- 125000003960 triphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C3=CC=CC=C3C12)* 0.000 description 1
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Classifications
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- C07D—HETEROCYCLIC COMPOUNDS
- C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
- C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
- C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
- C07D265/38—[b, e]-condensed with two six-membered rings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
- C09B69/02—Dyestuff salts, e.g. salts of acid dyes with basic dyes
- C09B69/06—Dyestuff salts, e.g. salts of acid dyes with basic dyes of cationic dyes with organic acids or with inorganic complex acids
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- A61K8/4926—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with one nitrogen as the only hetero atom having six membered rings
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B69/00—Dyes not provided for by a single group of this subclass
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- A61K8/494—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing heterocyclic compounds with more than one nitrogen as the only hetero atom
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- A61Q5/10—Preparations for permanently dyeing the hair
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C211/00—Compounds containing amino groups bound to a carbon skeleton
- C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
- C07C211/44—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring
- C07C211/49—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton
- C07C211/50—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to only one six-membered aromatic ring having at least two amino groups bound to the carbon skeleton with at least two amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C245/00—Compounds containing chains of at least two nitrogen atoms with at least one nitrogen-to-nitrogen multiple bond
- C07C245/02—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides
- C07C245/06—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings
- C07C245/08—Azo compounds, i.e. compounds having the free valencies of —N=N— groups attached to different atoms, e.g. diazohydroxides with nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings with the two nitrogen atoms of azo groups bound to carbon atoms of six-membered aromatic rings, e.g. azobenzene
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
- C07D233/54—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members
- C07D233/66—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having two double bonds between ring members or between ring members and non-ring members with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to ring carbon atoms
- C07D233/88—Nitrogen atoms, e.g. allantoin
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B19/00—Oxazine dyes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/02—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group
- C09B44/06—Azo dyes containing onium groups containing ammonium groups not directly attached to an azo group from coupling components containing hydroxyl as the only directing group
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
- C09B44/00—Azo dyes containing onium groups
- C09B44/10—Azo dyes containing onium groups containing cyclammonium groups attached to an azo group by a carbon atom of the ring system
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Abstract
本发明提供一种染发能力优异、水溶性和发泡性良好、清洗时和干燥后保持毛发的顺滑且耐汗性优异、抑制染色毛发褪色的染发用染料及其染发用组合物,所述化合物由下述通式(1)表示,化1:(X)(Z)(1),式中,X表示至少含有一个可具有取代基的碳原子数为0~20的氨基酸的碱性染料,Z表示含有氨基酸的非显色阴离子。
Description
技术领域
本发明涉及含有碱性染料和氨基酸的化合物、染发用染料以及染发用组合物。更详细地,涉及染发能力优异、水溶性和发泡性良好、清洗时和干燥后保持毛发的顺滑且耐汗性优异、能够有效抑制染色毛发褪色的染发用染料及染发用组合物。
背景技术
近年来,在广泛的年龄层中,通过将黑发和白发染色来享受各种各样的发色的人正在增加,作为染发剂,出售有很多染色剂(有时称为“染毛剂”)、头发修复精华素、发色护理剂、颜色护发素等。在染发处理中,主要利用使用染色能力高、着色良好的氧化染料的氧化染发剂(永久染发剂),但是存在容易引起毛发损伤和过敏等皮肤刺激的问题。因此,代替所述氧化染料,提出了使用安全性高的碱性染料的染发剂(专利文献1~5)。
使用所述碱性染料的半永久染发剂(发色护理剂和颜色护发素)因每日洗发和日晒等影响,存在染色褪色的问题,为了维持染色,需要反复多次染发。若反复染发,则毛发受到大的伤害,所以可能会更容易褪色,开发具有褪色抑制效果的碱性染料等成为重要的课题。
现有技术文献
专利文献
专利文献1:日本特开2004-269400号公报
专利文献2:日本特开2010-1278号公报
专利文献3:日本特开2017-88502号公报
专利文献4:国际公开第2013/190774号
专利文献5:国际公开第2014/203771号
发明内容
本发明要解决的课题是提供一种染发能力优异、水溶性和发泡性良好、清洗时和干燥后保持顺滑且耐汗性优异、抑制染色毛发褪色的染发用染料及染发用组合物。
本发明为了解决上述课题进行深入研究得出结果,以下是主旨,由以下的内容构成。
1.一种化合物,由下述通式(1)表示,
化1:
(X)(Z) (1),
式中,X表示至少含有一个能够具有取代基的碳原子数为0~20的氨基酸的碱性染料,Z表示含有氨基酸的非显色阴离子。
2.所述化合物中,在所述通式(1),X是由下述通式(2)表示的碱性染料,
化2:
式中,R1及R2分别独立表示
能够具有取代基的碳原子数为0~20的氨基、
能够具有取代基的碳原子数为2~20的直链状或支链状的烯基、
能够具有取代基的碳原子数为6~30的芳香族烃基、或者
能够具有取代基的碳原子数为2~30的杂环基。
3.所述化合物中,在所述通式(1)中,X是由下述通式(3)表示的碱性染料,
化3:
式中,R3~R18分别独立表示-H、卤素原子、-NO2、-NO、-CN、-OH、能够具有取代基的碳原子数为0~20的氨基、
能够具有取代基的碳原子数为2~20的直链状或支链状的烯基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷基、
能够具有取代基的碳原子数为3~20的环烷基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷氧基、
能够具有取代基的碳原子数为3~20的环烷氧基、
能够具有取代基的碳原子数为0~20的酰基、
能够具有取代基的碳原子数为6~30的芳香族烃基、或者
能够具有取代基的碳原子数为2~30的杂环基,
R3~R18能够在相邻的基团之间彼此键合而形成环。
4.所述化合物中,在所述通式(1)中,X是由下述通式(4)表示的碱性染料,
化4:
式中,R19~R27分别独立表示-H、卤素原子、-NO2、-NO、-CN、-OH、能够具有取代基的碳原子数为0~20的氨基、
能够具有取代基的碳原子数为2~20的直链状或支链状的烯基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷基、
能够具有取代基的碳原子数为3~20的环烷基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷氧基、
能够具有取代基的碳原子数为3~20的环烷氧基、
能够具有取代基的碳原子数为1~20的酰基、
能够具有取代基的碳原子数为6~30的芳香族烃基、或者
能够具有取代基的碳原子数为2~30的杂环基,
R19~R23及R24~R27能够在相邻的基团之间彼此键合而形成环。
5.所述化合物中,在所述通式(1)中,X是由下述通式(5)表示的碱性染料,
化5:
式中,R28~R30分别独立表示能够具有取代基的碳原子数为0~20的氨基、
能够具有取代基的碳原子数为2~20的直链状或支链状的烯基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷基、
能够具有取代基的碳原子数为1~20的环烷基、
能够具有取代基的碳原子数为1~20的直链状或支链状的烷氧基、
能够具有取代基的碳原子数为3~20的环烷氧基、
能够具有取代基的碳原子数为1~20的酰基、
能够具有取代基的碳原子数为6~30的芳香族烃基、或者
能够具有取代基的碳原子数为2~30的杂环基,
R29和R30能够彼此键合而形成环。
6.所述化合物中,在所述通式(1)中,由Z表示的含有氨基酸的非显色阴离子是氨基酸系的阴离子表面活性剂。
7.一种染发用染料,含有所述化合物。
8.一种染发用组合物,含有:所述染发用染料;从润湿剂、溶胀剂、渗透剂、溶剂、pH调节剂、表面活性剂、香料以及增稠剂组成的群中选择的至少一种助剂;以及水。
根据本发明的化合物、染发用染料,能够提供染发能力优异、水溶性和发泡性良好、清洗时和干燥后毛发不干燥、毛发不蓬松、保持顺滑且耐汗性优异、有效抑制染色毛发褪色的染发用组合物。
具体实施方式
以下,针对本发明的实施方式进行详细说明。此外,本发明不限于以下实施方式,可以在该主旨范围内实施各种变形。首先,具体说明关于由所述通式(1)表示的化合物,但本发明不限于此。
在通式(1)中,由“X”表示的在“含有至少一个可具有取代基的碳原子数为0~20的氨基的碱性染料”中的“碱性染料”还表示为阳离子染料,所述碱性染料表示由在分子结构中具有表示碱性(阳离子性)的鎓基的化合物构成的染料。作为含在由“X”表示的染料分子中的鎓基的例子,可举出铵基(-NH3 +)、磷基(-PH3 +)、氧鎓基(-OH2 +)、硫基(-SH2 +)、亚胺基(=NH2 +)、腈基(-C≡NH+)等,代表性的是具有下述的有关季铵基的基团。在这些基团中的“-H”的部分可以被可具有取代基的碳原子数为1~20的直链状或支链状的烷基或芳香族烃基等其它基团取代,这些基团也可以在一个染料分子中含有一个或多个。此外,这些碱性染料“X”优选为水溶性染料。
在通式(1)中,作为由“X”表示的在“含有至少一个可具有取代基的碳原子数为0~20的氨基的碱性染料”中“氨基”,可举出季铵基(-N+RR′R″,R、R′及R″是H或任意的取代基)、“=N+<”或“=N+RR′”(R、R′是H或任意的取代基)、未取代氨基(-NH2)、一取代氨基(-NHR,R是任意的取代基)或者二取代氨基(-NHRR′,R及R′是任意的取代基)。但是,优选地为X磺酸基(-SO3H)、羧基(-COOH)、磷酸基(-O-PO(OH)2)、异羟肟酸基(-CO-NH-OH)、膦酸基(-PO(OH)2)、硼酸基(-O-B(OH)2)、次膦酸基(-O-POH2)、硅醇基(-SiH2-OH或者-Si(OH)3)等的不含有酸性基团的碱性染料。
在通式(1)中,“Z”表示“含有氨基酸的非显色阴离子”。在通式(1)中“Z”是所述“X”的反离子,能够形成由通式(1)表示的化合物(络合物)。在本发明中“含有氨基酸的非显色阴离子”意指含有“氨基酸”或者“氨基酸”结构且能够成为阴离子的化合物。通常,氨基酸是具有氨基(-NHRR′,R及R′表示H或者可以相同或可以不同的任意基团)和羧基(-COOH、-COO-)的化合物。作为具体的氨基酸,可举出主要为甘氨酸、丙氨酸、缬氨酸、亮氨酸、异亮氨酸、丝氨酸、苏氨酸、半胱氨酸、胱氨酸、蛋氨酸、天冬氨酸、谷氨酸、天冬酰胺、谷氨酰胺、赖氨酸、精氨酸、苯丙氨酸、酪氨酸、色氨酸、组氨酸的α-氨基酸,在本发明中“含有氨基酸的非显色阴离子”可以在分子结构中含有这些氨基酸,因此,也可以具有氨基酸中的氨基等被取代的结构。
在通式(1)中的“Z”中,所述氨基和羧基可以是一个或多个。由“Z”表示的“含有氨基酸的非显色阴离子”处于“阴离子”状态时,“Z”是与阳离子“X”成对形成络合物的阴离子。因此,优选地,“X”的化合价和“Z”的化合价相同,更优选地,分别为1价或2价,特别优选地,分别为1价。
在由通式(1)表示的“X”、“Z”中,为使通式(1)中整体为中性,“X”和“Z”可以分别是一种也可以混合多个,但是,优选地,X的种类为一种,同样,优选地,“Z”的种类为一种。
在通式(1)中,“X”可以使用市售的碱性染料。此外,在通式(1)中,优选地,“X”是由所述通式(2)~(5)中的一种表示的化合物。
在通式(1)中,作为在“X”中含有或者由R1~R30表示的“可具有取代基的碳原子数为0~20的氨基”,可举出-NH2、乙氨基、乙酰氨基、苯氨基等的一取代氨基;二乙氨基、二苯氨基、乙酰基苯氨基等的二取代氨基等。此外,具有进一步与这些氨基键合的基团的、可具有三甲氨(或三甲基氨)基、三乙氨(或三乙基氨)基等的三烷氨(或三烷基氨)基、三苯基氨(或三甲基氨)基等的取代基的季氨基也包含在“可具有取代基的碳原子数为0~20的氨基”中,这些取代基可以相同也可以彼此不同。
在通式(1)中,作为由R1~R30表示的“可具有取代基的碳原子数为2~20的直链状或支链状的烯基”中的“碳原子数为2~20的直链状或支链状的烯基”,具体地,可举出乙烯基、烯丙基、异丙烯基、2-丁烯基、1-己烯基或者多个这些烯基键合的直链状或支链状的基团。
在通式(1)中,作为由R1~R30表示的“可具有取代基的碳原子数为6~30的芳香族烃基”中的“碳原子数为6~30的芳香族烃基”,具体地,可举出苯基、联苯基、三苯基、四苯基、苯乙烯基、萘基、蒽基、苊基、菲基、芴基、茚基、芘基、三亚苯基等,也可以插入酰基和氨基。在这里,本发明的“芳香族烃基”表示的是芳香族烃基和稠合多环芳香族基。
在通式(1)中,作为由R1~R30表示的“可具有取代基的碳原子数为2~30的杂环基”中的“碳原子数为2~30的杂环基”,具体地,可举出三嗪基、吡啶基、嘧啶基、咪唑基、呋喃基、吡咯基、噻吩基、喹啉基、异喹啉基、苯并呋喃基、苯并噻吩基、吲哚基、咔唑基、咔啉基、吡啶并吲哚基、恶唑基、苯并恶唑基、噻唑基、苯并噻唑基、喹喔啉基、苯并咪唑基、吡唑基、二苯并呋喃基、二苯并噻吩基、萘啶基、菲咯啉基、吖啶基、乙内酰脲基等,也可以介入酰基和氨基而键合。
在通式(3)和(4)中,作为由R3~R27表示的“卤素原子”,可举出氟原子、氯原子、溴原子、碘原子等。在本发明中,作为“卤素原子”,优选为氟原子或者氯原子。
在通式(3)~(5)中,作为由R3~R30表示的“可具有取代基的碳原子数为1~20的直链状或支链状的烷基”中的“碳原子数为1~20的直链状或支链状的烷基”,具体地,可举出甲基、乙基、丙基、丁基、戊基、己基、庚基、辛基、壬基、癸基等的直链状的烷基;异丙基、异丁基、仲丁基、叔丁基、异辛基、叔辛基等的支链状的烷基。
在通式(3)~(5)中,作为由R3~R30表示的“可具有取代基的碳原子数为3~20的环烷基”中的“碳原子数为3~20的环烷基”,具体地,可举出环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环癸基、环十二烷基等。
在通式(3)~(5)中,作为由R3~R30表示的“可具有取代基的碳原子数为1~20的直链状或支链状的烷氧基”中的“碳原子数为1~20的直链状或支链状的烷氧基”,具体地,可举出甲氧基、乙氧基、丙氧基、正丁氧基、正戊氧基、正己氧基、庚氧基、辛氧基、壬氧基、癸氧基等的直链状的烷氧基;异丙氧基、异丁氧基、仲丁氧基、叔丁氧基、异辛氧基、叔辛氧基等的支链状的烷氧基。
在通式(3)~(5)中,作为由R3~R30表示的“可具有取代基的碳原子数为3~20的环烷氧基”中的“碳原子数为3~20的环烷氧基”,具体地,可举出环丙氧基、环丁氧基、环戊氧基、环己氧基等。
在通式(3)~(5)中,作为由R3~R30表示的“可具有取代基的碳原子数为1~20的酰基”中的“碳原子数为1~20的酰基”,具体地,可举出甲酰基、乙酰基、丙酰基、丙烯酰基、苯甲酰基等。
作为在通式(1)的X中的“可具有取代基的碳原子数为0~20的氨基”中的“取代基”或者由通式(2)~(5)中R1~R30表示的
“可具有取代基的碳原子数为0~20的氨基”、
“可具有取代基的碳原子数为2~20的直链状或支链状的烯基”、
“可具有取代基的碳原子数为1~20的直链状或支链状的烷基”、
“可具有取代基的碳原子数为3~20的环烷基”、
“可具有取代基的碳原子数为1~20的直链状或支链状的烷氧基”、
“可具有取代基的碳原子数为3~20的环烷氧基”、
“可具有取代基的碳原子数为1~20的酰基”、
“可具有取代基的碳原子数为6~30的芳香族烃基”或者
“可具有取代基的碳原子数为5~30的杂环基”中的“取代基”,
具体地,可举出硝基(-NO2)、亚硝基(-NO)、氰基(-CN)、羟基(-OH);氟原子、氯原子、溴原子、碘原子等的卤素原子;
未取代氨基;甲氨基、二甲氨基、二乙氨基、乙基甲氨基、甲基丙氨基、二叔丁氨基、二苯氨基等的具有碳原子数为1~20的直链状或支链状的烷基或者碳原子数为6~30的芳基的一取代或二取代氨基;
磺酰胺基(-S(=O)2-NRR′)(基团中的“-NRR′”是未取代氨基;甲氨基、二甲氨基、二乙氨基、乙基甲氨基、甲基丙氨基、二叔丁基氨基、二苯氨基等的具有碳原子数为1~20的直链状或支链状的烷基或者碳原子数为6~30的芳基的一取代或二取代氨基);
甲基、乙基、正丙基、异丙基、正丁基、仲丁基、叔丁基、戊基、正己基、异己基、庚基、正辛基、叔辛基、异辛基、壬基、癸基等的碳原子数为1~20的直链状或支链状的烷基;
环丙基、环丁基、环戊基、环己基、环庚基、环辛基、环癸基、环十二烷基等的碳原子数为3~20的环烷基;
甲氧基、乙氧基、丙氧基、叔丁氧基、正戊氧基、正己氧基等的碳原子数为1~20的直链状或支链状的烷氧基;
环丙氧基、环丁氧基、环戊氧基、环己氧基等的碳原子数为3~20的环烷氧基;乙烯基、1-丙烯基、烯丙基、1-丁烯基、2-丁烯基、1-戊稀基、1-己烯基、异丙烯基、异丁烯基或者多个这些烯基键合的碳原子数为2~20的直链状或支链状的烯基;
甲酰基、乙酰基、丙酰基、丙烯酰基、苯甲酰基等的碳原子数为1~20的酰基;苯基、萘基、蒽基、菲基、芘基、三亚苯基、茚基、芴基、苯乙烯基等的碳原子数为6~30的芳香族烃基;
吡啶基、嘧啶基、三嗪基、吡咯基、咪唑基、吡唑基、三唑基、吡嗪基、哒嗪基、哌啶基、哌嗪基、喹啉基、异喹啉基、萘啶基、吲哚基、苯并咪唑基、咔唑基、咔啉基、吡啶并吲哚基、吖啶基、菲咯啉基、菲啶基、乙内酰脲基、呋喃基、苯并呋喃基、二苯并呋喃基、吡喃基、香豆酰基、异苯并呋喃基、呫吨基、氧蒽基、吡喃基、噻吩基、噻喃基、苯并噻吩基、二苯并噻吩基、噻吨基、恶唑基、苯并恶唑基、吗啉基、噻唑基、苯并噻唑基等的碳原子数为2~30的杂环基;
环丙烯基、环丁烯基、环戊稀基、环己烯基、环庚烯基、(1,3-或1,4-)环己二烯基、1,5-环辛二烯基等的碳原子数为3~30的环状烯烃基等。这些“取代基”可以仅包含一个,也可以包含多个,当包含多个时,可以相同也可以不同。此外,这些“取代基”可以具有所述例示的取代基,进一步,这些取代基之间可以通过单键合、取代或未取代的亚甲基、氧原子或者硫原子,彼此键合而形成环。
在通式(2)中,作为R1或者R2,优选为
可具有取代基的碳原子数为6~30的芳香族烃基或者
可具有取代基的碳原子数为2~30的杂环基。
在通式(3)中,作为R3~R18,优选为-H、卤素原子、可具有取代基的碳原子数为0~20的氨基或者可具有取代基的碳原子数为1~20的直链状或支链状的烷基。
在通式(3)中,R3~R18可以在相邻基团之间彼此键合而形成环,当形成环时,优选地,R3和R4、R5和R6、R7~R11、R12~R16、R17和R18彼此键合而形成环,该环优选为五元环或者六元环。
在通式(4)中,作为R3~R18,优选为-H、
可具有取代基的碳原子数为0~20的氨基或者
可具有取代基的碳原子数为6~30的芳香族烃基。
在通式(4)中,R19~R27也可以是相邻基团之间彼此键合而形成环,当形成环时,优选地,R20和R21、R22和R23、R24~R27彼此键合而形成环,该环优选为五元环或者六元环。
在通式(5)中,作为R28~R30,优选为
可具有取代基的碳原子数为1~20的直链状或支链状的环烷基、
可具有取代基的碳原子数为6~30的芳香族烃基或者
可具有取代基的碳原子数为2~30的杂环基。
在通式(5)中,R29和R30也可以彼此键合而形成环,当形成环时,优选为五元环或者六元环。
在通式(1)中,由“Z”表示的“含有氨基酸的非显色阴离子”优选为在分子结构中含有氨基酸的氨基酸系表面活性剂,因此,优选为氨基酸系阴离子表面活性剂。具体地,可举出N-酰基-N-烷基甘氨酸盐(N-椰油酰基-N-甲基甘氨酸盐等的N-C8~C22烷酰基-N-烷酰基甘氨酸盐)、
N-酰基-N-烷基谷氨酸盐(N-椰油酰基-N-甲基谷氨酸盐等的N-C8~C22烷酰基-N-烷基谷氨酸盐)、
N-酰基-N-烷基丙氨酸盐(N-椰油酰基-N-甲基丙氨酸盐、N-月桂酰基-N-甲基-β-丙氨酸盐等的N-C8~C22烷酰基-N-烷基丙氨酸盐)、
N-酰基-N-烷基天冬氨酸盐(N-椰油酰基-N-甲基天冬氨酸盐等的N-C8~C22烷酰基-N-烷基天冬氨酸盐)、
N-酰基甘氨酸盐(N-椰油酰基甘氨酸盐等的N-C8~C22烷酰基甘氨酸盐)、
N-酰基谷氨酸盐(月桂酰基谷氨酸钠、N-椰油酰基谷氨酸盐等的N-C8~C22烷酰基谷氨酸盐)、
N-酰基丙氨酸盐(N-椰油酰基丙氨酸盐等的N-C8~C22烷酰基丙氨酸盐)、
N-酰基天冬氨酸盐(N-月桂酰基天冬氨酸盐等的N-C8~C22烷酰基天冬氨酸盐)、
N-酰基肌氨酸盐(N-椰油酰基肌氨酸盐等的N-C8~C22烷酰基肌氨酸盐)等的氨基酸系阴离子(负离子)表面活性剂。作为这些盐,例如,可举出锂、钠、钾、铯等的碱金属盐;三乙醇胺等的三烷基胺盐;精氨酸等的盐性氨基酸盐等。
在通式(1)中,作为由“Z”表示的氨基酸系阴离子性表面活性剂,优选为N-酰基-N-烷基谷氨酸盐、N-月桂酰基-N-甲基-β-丙氨酸盐等的N-酰基-N-烷基丙氨酸盐、月桂酰基谷氨酸钠等的N-酰基谷氨酸盐、N-酰基丙氨酸盐。在这些氨基酸系阴离子表面活性剂中,作为含有“N-烷基”基团部分的情况中的烷基,可举出甲基、乙基、丙基等,优选为甲基。此外,在这些氨基酸系阴离子表面活性剂中,作为“酰基”基团,例如,可举出椰油酰基、月桂酰基、肉豆蔻酰基、棕榈酰基、硬脂酰基等,优选为椰油酰基或者月桂酰基。
作为由通式(1)表示的本发明的化合物,优选化合物的具体例如下所示,但本发明不限于这些化合物。此外,在下述结构式中,省略记载了一些氢原子,此外,即使存在立体异构体,也记载了平面结构式。
【化6】
【化7】
【化8】
【化9】
【化10】
【化11】
【化12】
【化13】
【化14】
【化15】
【化16】
【化17】
由所述通式(1)表示的化合物例如可以将所述通式(1)中的由(X)表示的碱性染料和由(Z)表示的氨基酸钠盐等的盐作为起始原料合成。具体地,将所述碱性染料溶解于水和有机溶剂等中,在适合的温度条件下,添加氨基酸钠盐等进行反应,通过将得到的固体在适合的溶剂、温度等的条件下进行精制,能够得到本发明的染发用染料(将氨基酸作为抗衡离子的染料)的化合物。
由通式(1)表示的本发明的化合物,可以用根据柱色谱法的精制;根据硅胶、活性炭、活性白土等的吸附精制;根据溶剂的重结晶和结晶法等公知的方法进行精制。此外,化合物的鉴定和物性评价分析可以通过紫外可见吸收光谱分析(UV-Vis)、热重分析-差热分析(TG-DTA)、气象色谱分析(GC)、核磁共振分析(NMR)的分析等进行。
根据本发明的化合物优选为以所谓染发剂(hair colorants)的形式进行使用。由通式(1)表示的化合物优选为作为染发用染料进行使用,通过混合其它染料和添加剂、助剂等的成分等,可以作为含有由通式(1)表示的化合物的染发用染料进行使用。适合于本发明的染发用染料的实施方式是染发用组合物,含有由通式(1)表示的化合物的染发用染料和从由湿润剂、溶胀剂、渗透剂、溶剂、pH调节剂、表面活性剂、香料和增稠剂组成的群中选择的至少一种助剂以及水。
作为湿润剂,可举出甘油、丙二醇、山梨糖醇、1,3-丁二醇、聚乙二醇类等。当使用湿润剂时,其含量基于染发用组合物的总量优选为0.1重量%~20重量%,更优选为0.5重量%~10重量%。
作为溶胀剂,可举出含有氨(氢氧化铵)或者单乙醇胺(MEA)的碱性水溶液。当使用溶胀剂时,其含量基于染发用组合物的总量优选为0.1重量%~20重量%,更优选为0.5重量%~10重量%。
此外,作为渗透剂、溶剂,可举出乙醇、1-丙醇、2-丙醇、1-丁醇、2-丁醇、丁氧基乙醇等的具有碳原子数为1~6的烷基的一价酒精;丙二醇、丁二醇、戊二醇、己二醇、己三醇、庚二醇、庚三醇、辛二醇、辛三醇、异戊二醇、丙烯乙二醇、甘油、二乙二醇单乙醚等的碳原子数为3~8的多价酒精或者其醚;N-甲基-2-吡咯烷酮、N-乙基-2-吡咯烷酮、N-丙基-2-吡咯烷酮、N-丁基-2-吡咯烷酮、N-环己基-2-吡咯烷酮等的在室温(25℃±2℃)下呈液态的N-烷基吡咯烷酮;碳酸亚乙酯、碳酸亚丙酯等的碳酸亚烷基酯(低级碳酸亚烷基酯);苄氧基乙氧基乙醇、苄醇、苄氧基乙醇、肉桂醇、对茴香醇、对甲基苄醇、苯氧乙醇、苯氧、2-苄基乙醇、β-苯乙醇等的芳香醇。在其中,优选为芳香醇或N-烷基吡咯烷酮,更优选为苄醇、苄氧基乙氧基乙醇、苄氧基乙醇。当使用渗透剂、溶剂时,其含量基于染发用组合物的总量优选为2重量%~40重量%,更优选为5重量%~20重量%。
作为pH调节剂,可举出磷酸、乳酸-乳酸钠、柠檬酸-柠檬酸钠等的酸;氨水、氢氧化钠、氢氧化钾、碳酸钠等的碱。当使用pH调节剂时,其含量基于染发用组合物的总量优选为0.1重量%~10重量%,更优选为0.5重量%~5重量%。
作为表面活性剂,主要使用阳离子表面活性剂或者非离子表面活性剂。具体地,可举出聚硅氧烷等的硅化合物、聚氧乙烯烷基醚、聚氧乙烯脂肪酸酯、聚甘油脂肪酸酯、脂肪胺及其季铵盐(三甲基硬脂基氯化铵等)、山梨醇烷基醚等的糖醇醚类、聚氧乙烯脱水山梨糖醇脂肪酸酯等,但不限于这些。在其中,优选为聚氧乙烯脱水山梨糖醇脂肪酸酯。通过使用聚氧乙烯脱水山梨糖醇脂肪酸酯,进一步提高减少皮肤污染的效果(防止皮肤污染的能力)。
作为聚氧乙烯脱水山梨糖醇脂肪酸酯,优选为从由聚氧乙烯脱水山梨糖醇单月桂酸酯、聚氧乙烯脱水山梨糖醇单棕榈酸酯、聚氧乙烯脱水山梨糖醇单硬脂酸酯和聚氧乙烯脱水山梨糖醇单油酸酯组成的群中选择的至少一个。
当使用表面活性剂时,从减少皮肤污染的观点出发,其含量基于染发用组合物的总量优选为0.1重量%~20重量%,更优选0.5重量%~10重量%。
作为香料,可举出香兰素、合成醇、胡椒醛、香豆素、2-甲基-3-(3,4-亚甲二氧基-苯基)-丙醛、4-(4-羟基苯基)-2-丁酮、苯甲醛、茴香醇、3,4-二甲氧基苯甲醛、乙酸胡椒酯、苯乙醛二甲缩醛、苯氧乙醇、苯乙醛甘油缩醛、呋喃醇、糖内酯、麦芽酚、乙基麦芽酚、乙基二甘醇、醋酸苄酯、芳樟醇、樟脑、松油醇、香茅醇、香叶醇、2,6-壬二烯、碳酸甲基辛酯、3,7-二甲基-2,6-辛二烯醛、壬醛等。当使用香料时,其含量基于染发用组合物的总量优选为0.00001重量%~2重量%。
作为增稠剂,可举出瓜尔胶及其衍生物、羟乙基纤维素、黄原胶、胶原蛋白、明胶、羧甲基纤维素钠盐、羧乙烯聚合物(注册商标,Carbopol)、海藻酸钠、阿拉伯树胶(Gumarabic)、纤维素衍生物和聚合物(环氧乙烷)来源的增稠剂。这些增稠剂具有使染发用组合物高粘度化而成为易于处理的形态的凝胶的效果。当使用增稠剂时,其含量基于染发用组合物的总量优选为0.1重量%~20重量%,更优选为0.5重量%~10重量%。
用于本发明的染发用组合物的水没有特别限定,可以使用离子交换水、净化水、纯净水等。
本发明的含有由通式(1)表示的化合物的染发用染料是作为其自身的染发用染料具有优异的染发能力和稳健性,并能够将毛发均匀地染色。此外,通过含有由通式(1)表示的化合物的染发用染料与其它色系的毛发用染料组合,还能够调色为黄色、棕色、黑色系。
例如,作为组合碱性染料,可举出在分子内具有氨基或者取代氨基的直接染料,具体地,可举出红色213号(C.I.基本紫10,罗丹明B)、红色214号(C.I.基本紫,罗丹明B醋酸盐);碱性蓝(C.I.基本蓝)7、9、26、75、99;碱性红(C.I.基本红)2、22、51、76;碱性黄(C.I.基本黄)57、87;碱性橙(C.I.基本橙)31;碱性棕(C.I.基本棕)16、17;碱性紫(C.I.基本紫)2、3、4、14等。此外,“C.I.”意指颜色索引。
作为组合HC染料,例如,可举出在分子内具有硝基的直接染料,具体地,可举出C.I.HC蓝2、15;C.I.HC红1、3、7、11、13;C.I.HC黄2、4、5、9、11、13;C.I.HC橙1、2;C.I.HC紫1、2;4-羟基丙基氨基-3-硝基苯酚等。
在本发明的染发用组合物的实施方式中,优选地,含有由通式(1)表示的化合物的染发用染料基于染发用组合物的总量为0.001重量%~5重量%,其余物质是含有从由湿润剂、溶胀剂、渗透剂、溶剂、pH调节剂、表面活性剂、香料和增稠剂组成的群中选择的至少一种助剂以及水的物质。若染发用染料的含量小于0.001重量%,则难以获得保持色调和均染性的效果,即使添加超过5重量%的量,提高染色等的效果也会减小。染发用染料的含量基于染发用组合物的总量优选为0.01重量%~5重量%,更优选为0.05重量%~2重量%。
本发明的染发用组合物的pH值优选为4~9,更优选为5~7。染发用组合物的pH值可以通过公知的方法调节,但是优选使用柠檬酸一水合物和柠檬酸三钠二水合物等的pH调节剂进行。即,例如,当制备pH 6的染发用组合物时,通过将柠檬酸一水合物和柠檬酸三钠二水合物溶解于水,预先制备pH6水溶液后,在该水溶液中添加含有由通式(1)表示的化合物的染发剂染料和根据需要添加其它添加剂(助剂等),能够得到pH 6的染发用组合物。
本发明的染发用组合物,在不妨碍本发明效果的范围内,也可以添加公知的化妆品用成分。作为可添加的化妆品用成分,可举出高级酒精、凡士林、多价酒精、酯类、防腐剂、杀菌剂、硅氧烷衍生物、水溶性聚合物等。
作为使用本发明的染发用组合物的染发方法,具体地、例如,可以通过对人的毛发和家畜的毛等的染发对象接触本发明的染发用组合物来进行染发。染发温度优选为5℃~60℃,考虑到在头皮附近进行,更优选为15℃~45℃。染发时间优选为5分钟~60分钟,更优选为10分钟~30分钟。
染发后,通常进行清洗和干燥等后处理。清洗进行到染发剂的颜色完全不溶出为止即可,例如,在5℃~40℃、以5L/分钟~15L/分钟的流水下每0.5分钟~2分钟进行冲洗。清洗后的干燥可以是自然干燥(通常在5℃~40℃下10分钟~10小时),根据需要也可以使用热风干燥机(通常在40℃~60℃下10分钟~10小时)。
此外,清洗后,也可以进行皂洗。皂洗例如是使用适量的皂洗液(洗发水和温水的混合液),通常在15℃~50℃的温度下清洗1分钟~10分钟,进行清洗直到完全除去皂洗液。
通过如上所述的方式,含有根据本发明的化合物的染发用染料和染发用组合物在染色剂、头发修复精华素、发色护理剂的任一者中也能够发挥优异的染色效果。特别是,能够对染色能力弱的发色护理剂发挥效果。
【实施例】
以下,根据实施例,较为详细地说明本发明,但本发明不限于以下的实施例。
<试样评价方法>
在以下实施例和比较例中,将使用分光色度计(彩色技术系统株式会社,JS555)对得到的试样进行评价。此外,染发浓度(K/Sd)按照以下的顺序算出。使用分光色度计测定在染发前(白发)及染发后(染发)的试样的各波长(λ)中的反射率(Rλ),使用下述Kubelka-Munk公式算出光学浓度(K/S)。将从染发的光学浓度(K/S)减去白发的光学浓度(K/S)的值作为染发浓度(K/Sd)求出。
Kubelka-Munk公式:
K/S=∑(1-Rλ)2/2Rλ
Rλ:波长(λ)中的反射率
λ:400nm~700nm(10nm间隔)
色彩使用CIE L*a*b*表色彩系统,用分光色度计测定L*、a*以及b*。L*是明度,其越大,着色强度越小。a*和b*是表示色调和饱和度的色度。a*对应于红-绿色轴,+为红色,-为绿色。b*对应于黄-蓝色轴,+为黄色,-为蓝色。
此外,针对染发前和染发后的各个试样测定色彩(L*、a*、b*),从该差值ΔL*、Δa*以及Δb*,通过以下公式算出色差ΔE*和色调差ΔH*。
ΔE*={(ΔL*)2+(Δa*)2+(Δb*)2}1/2
ΔH*={(Δa*)2+(Δb*)2}1/2
耐汗性评价通过求出针对未经测试试样的下述耐汗性试样的K/Sd的比率(残留率%)、色差(ΔE*)以及色调差(ΔH*)来进行评价。此外,ΔE*、ΔH*是由彩色技术系统株式会社制造的分光色度计JS555测出L*、a*以及b*,并由下述所示的公式求出的。ΔE*越小表示变色越少,并且ΔH*越小表示色调变化越小并耐汗性优异。
ΔE*={(ΔL*)2+(Δa*)2+(Δb*)2}1/2
ΔH*={(Δa*)2+(Δb*)2}1/2
以下,针对本发明的实施方式,根据实施例具体地说明,但本发明不限于以下实施例。
[合成实施例1]化合物(A-1)的合成
在反应容器中加入50g的C.I.基本蓝75、500mL的MeOH、250mL的水,在60℃下加热,溶解C.I.基本蓝75。在该溶液中加入45.7g的月桂酰基谷氨酸钠,在60℃下搅拌2小时。减压蒸馏除去甲醇,将析出固体与水过滤分离。将得到的固体在500mL的变性乙醇中,在60℃下搅拌1小时,通过过滤除去不溶物,重复两次减压蒸馏除去溶剂的操作,得到由下述结构式(A-1)表示的化合物(54.7g,收率为62%)。
【化18】
进行化合物(A-1)的NMR测定,得到下述的结果。
1H NMR(600MHz,CD3OD):δ(ppm)=0.89(3H,t,J=6.9Hz)、1.36(6H,t,J=7.6Hz)、1.60-1.62(18H,m)、2.23(2H,t,J=6.2Hz)、2.28-2.32(2H,m)、3.82(4H,m)、4.26-4.28(1H,m)、7.01(1H,d,J=2.8Hz)、7.05(1H,d,J=2.8Hz)、7.31-7.34(2H,m)、7.39-7.40(2H,m)、7.48-7.52(3H,m)、7.78-7.80(2H,m)。
[合成实施例2]化合物(A-2)的合成
在反应容器中加入10g的C.I.基本红51和200mL的水,在60℃下加热,溶解C.I.基本红51。在该溶液中加入18.9g的月桂酰基谷氨酸钠,在60℃下搅拌1小时。将析出的固体和溶液进行分离,将得到的固体在100mL的变性乙醇中,在60℃下搅拌1小时之后,通过过滤除去不溶物之后,减压蒸馏除去溶剂,得到由下述结构式(A-2)表示的化合物(11.8g,收率为57%)。
【化19】
进行化合物(A-2)的NMR测定,得到下述的结果。
1H NMR(600MHz,CD3OD):δ(ppm)=0.89(3H,t,J=6.9Hz)、1.60-1.62(18H,m)、2.23(2H,t,J=6.2Hz)、2.28-2.32(2H,m)、3.26(6H,s)、4.04(6H,s)、4.26-4.28(1H,m)、6.94(2H,d,J=8.9Hz)、7.50(2H,s)、7.97(2H,d,J=8.9)。
[合成实施例3]化合物(A-3)的合成
在反应容器中加入10g的C.I.基本紫2和300mL的水,在60℃下加热,溶解C.I.基本紫2。在该溶液中加入18.9g的月桂酰基谷氨酸钠,在60℃下搅拌1小时。除去溶液部分,将得到的固体在500mL的变性乙醇中,在60℃下搅拌1小时,通过过滤除去不溶物之后,减压蒸馏除去溶剂。将得到的固体在100mL的变性乙醇中,在60℃下搅拌1小时,通过过滤除去不溶物,减压蒸馏除去溶剂,得到由下述结构式(A-3)表示的化合物(15.9g,收率为89.7%)。
【化20】
进行化合物(A-3)的NMR测定,得到下述的结果。
1H NMR(600MHz,CD3OD):δ(ppm)=0.89(3H,t,J=6.9Hz)、1.60-1.62(18H,m)、2.11(9H,s)、2.23(2H,t,J=6.2)、2.28-2.32(2H,m)、4.26-4.28(1H,m)、6.78(3H,d,J=8.3Hz)、6.93(3H,s)、6.99(3H,d,J=8.3Hz)。
[合成实施例4]化合物(A-4)的合成
在反应容器中加入10g的C.I.HC蓝15和350mL水,在60℃下加热,溶解C.I.HC蓝15。在该溶液中加入7.0g的月桂酰基谷氨酸钠,在60℃下搅拌2小时。将除去液体部分而得到的固体在200mL的变性乙醇中,在60℃下搅拌1小时,通过过滤除去不溶物,减压蒸馏除去溶剂,得到由下述结构式(A-4)表示的化合物(10.6g,收率为73%)。
【化21】
进行化合物(A-4)的NMR测定,得到下述的结果。
1H NMR(600MHz,CD3OD):δ(ppm)=0.89(3H,t,J=6.9Hz)、1.60-1.62(18H,m)、2.21(12H,s)、2.23(2H,t,J=6.2)、2.28-2.32(2H,m)、4.26-4.28(1H,m)、7.14(4H,s)、7.55-7.61(3H,m)。
[合成实施例5]化合物(A-5)的合成
在反应容器中加入30g的C.I.基本棕16和300mL的甲醇,在60℃下加热,溶解C.I.基本棕16。在该溶液中加入29.5g的月桂酰基谷氨酸钠,在60℃下搅拌2小时。将减压蒸馏除去溶剂而得到的固体在300mL的变性乙醇中,在60℃下搅拌1小时,通过过滤除去不溶物。将减压蒸馏除去溶剂而得到的固体在150mL的水中,在60℃下搅拌1小时,重复三次通过过滤除去溶液的操作,将得到的固体干燥,得到由下述结构式(A-5)表示的化合物(16.0g,收率为29.3%)。
【化22】
进行化合物(A-5)的NMR测定,得到下述的结果。
1H NMR(600MHz,CD3OD):δ(ppm)=0.89(3H,t,J=6.9Hz)、1.60-1.62(18H,m)、2.23(2H,t,J=6.2Hz)、2.28-2.32(2H,m)、3.83(9H,s)、4.26-4.28(1H,m)、7.73(2H,d,J=8.9Hz)、7.82(1H,d,J=8.9Hz)、7.92(1H,d,J=9.6Hz)、8.01(1H,d,J=9.6Hz)、9.07(1H,s)。
[实施例1]
<染发染色>
将16.5mg的作为染发用染料的化合物(A-3)、100mg的乙醇、100mg的作为表面活性剂的三甲基硬脂基氯化铵、200mg的作为增稠剂的羟乙基纤维素、9.53g的作为pH调节剂的pH 6水溶液(柠檬酸·H2O/柠檬酸·3Na·2H2O/水(1:11:988)水溶液)混合,制备染色凝胶。
然后,染色的毛发使用BEAULAX株式会社制造的白发100%BM-W。对于1质量份的毛发,取2质量份的染色凝胶,使用梳子在毛发上涂抹每个角落,在40℃下染色10分钟,并进行清洗。
化合物(A-3)能够得到在染发染色中具有充分的水溶性、染发时发泡性良好、清洗时和干燥后毛发不干燥、并且毛发不蓬松、保持顺滑的试样。
通过所述<试样评价方法>,测定试验前的试样的染发浓度(K/Sd)和色彩。结果示出在表1中。
<耐汗性试验>
针对充分干燥的试样,进行下述的人工汗液(林纯药工业株式会社制造)处理,并进行清洗。
人工汗液处理:
·人工汗液成分
(酸性)0.05%的L-组氨酸盐酸盐一水合物
0.50%的氯化钠
0.22%的磷酸二氢钠二水合物
0.005%的氢氧化钠水溶液(pH 5.5)
(碱性)0.05%的L-组氨酸盐酸盐一水合物
0.50%的氯化钠
0.50%磷酸氢二钠十二水合物
0.007%氢氧化钠水溶液(pH 8.0)
·浴比:1:10(对于1质量份的染发,10质量份的处理液)
·处理温度:40℃
·处理时间:10分钟
针对在上述条件下进行人工汗液处理的毛发试样,测定染色浓度(K/Sd),评价残留率(%)。相同地,测定色彩,评价试验前后的色调差(ΔH)。结果示出在表1中。
【表1】
[实施例2和实施例3]
除了代替实施例1的化合物(A-3)使用化合物(A-4)和化合物(A-5)之外,与实施例1同样进行测定染发染色、染发浓度以及耐汗性试验。得到的试样与实施例1相同,能够得到水溶性、发泡性、清洗时和干燥后毛发不干燥、并且毛发不蓬松、保持顺滑的试样。染发浓度测定、耐汗性试验的结果示出在表1中。
[比较例1~比较例3]
除了代替实施例1的化合物(A-1)使用不属于本发明的化合物的染料的C.I.基本紫2、C.I.HC蓝15以及C.I.基本棕16之外,与实施例1同样进行测定染发染色、染发浓度以及耐汗性试验。此外,上述的实施例1和比较例1、实施例2和比较例2以及实施例3和比较例3中所使用的染发用组合物中的各个染料的浓度调节为使得着色毛发的每单位质量的染料(仅相当于显色成分,排除非显色成分)的质量相等(实际上,通过测定实施例和比较例的染料凝胶的溶液的吸光度来一起调节染料浓度)。这些结果一起示出在表1中(表中的化合物的“C.I.”被省略)。
从表1的结果可知,使用含有本发明的化合物的染发用染料和染发用组合物与使用以往的染料相比,染发浓度高,能够得到高的染发能力。此外,从酸性和碱性的耐汗试验的结果可知,与比较例的染料相比,试验后染发浓度的残留率高,试验后的色调变化也与以往相同。进一步,使用实施例的染发用组合物,关于水溶性、发泡性、清洗时和干燥后毛发的干燥与否和顺滑,得到了与比较例相同的结果。
产业上利用可能性
根据本发明的化合物和染发用染料,能够提供染发能力优异、水溶性和发泡性良好、清洗时和干燥后保持毛发的顺滑且耐汗性优异、能够有效抑制染色毛发褪色的染发用组合物。
Claims (4)
1.一种化合物,所述化合物为下述结构式中的一个,【化6】
【化7】
【化8】
【化9】
【化10】
【化11】
2.根据权利要求1所述的化合物,其中,
所述化合物为下述结构式中的一个,
【化8】
【化9】
【化10】
3.一种染发用染料,含有权利要求1或2所述的化合物。
4.一种染发用组合物,含有:
权利要求3所述的染发用染料;
从由湿润剂、溶胀剂、渗透剂及溶剂、pH调节剂、表面活性剂、香料以及增稠剂组成的群中选择的至少一种助剂;以及
水,
所述湿润剂为甘油、丙二醇、山梨糖醇、1,3-丁二醇、或者聚乙二醇类,
所述溶胀剂为含有氨或者单乙醇胺的碱性水溶液,
所述渗透剂及溶剂为具有碳原子数为1~6的烷基的一元醇、碳原子数为3~8的多元醇或者其醚、在室温下呈液态的N-烷基吡咯烷酮、碳酸亚烷基酯、或者芳香醇,
所述表面活性剂为硅化合物、聚氧乙烯烷基醚、聚氧乙烯脂肪酸酯、聚甘油脂肪酸酯、脂肪胺及其季铵盐、糖醇醚类、或者聚氧乙烯脱水山梨糖醇脂肪酸酯。
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- 2019-08-30 EP EP19194510.4A patent/EP3616680B1/en not_active Revoked
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KR20200026087A (ko) | 2020-03-10 |
JP2022087179A (ja) | 2022-06-09 |
JP2020033495A (ja) | 2020-03-05 |
EP3616680A1 (en) | 2020-03-04 |
US10738019B2 (en) | 2020-08-11 |
EP3616680B1 (en) | 2021-03-17 |
US20200071283A1 (en) | 2020-03-05 |
CN110872454A (zh) | 2020-03-10 |
KR102662459B1 (ko) | 2024-04-30 |
JP7350125B2 (ja) | 2023-09-25 |
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