JP4907185B2 - Shampoo, conditioner, hair treatment, hair water, hair wax, hair mousse or hair gel - Google Patents
Shampoo, conditioner, hair treatment, hair water, hair wax, hair mousse or hair gel Download PDFInfo
- Publication number
- JP4907185B2 JP4907185B2 JP2006026170A JP2006026170A JP4907185B2 JP 4907185 B2 JP4907185 B2 JP 4907185B2 JP 2006026170 A JP2006026170 A JP 2006026170A JP 2006026170 A JP2006026170 A JP 2006026170A JP 4907185 B2 JP4907185 B2 JP 4907185B2
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- JP
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- Prior art keywords
- hair
- mercapto
- group
- formula
- methyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
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- 210000004209 hair Anatomy 0.000 title claims description 242
- 238000011282 treatment Methods 0.000 title claims description 50
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 title claims description 46
- 239000002453 shampoo Substances 0.000 title claims description 30
- 241000195940 Bryophyta Species 0.000 title claims description 21
- 235000011929 mousse Nutrition 0.000 title claims description 21
- -1 mercapto compound Chemical group 0.000 claims description 205
- CWERGRDVMFNCDR-UHFFFAOYSA-N alpha-mercaptoacetic acid Natural products OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 claims description 21
- 125000003396 thiol group Chemical group [H]S* 0.000 claims description 20
- PMNLUUOXGOOLSP-UHFFFAOYSA-N alpha-mercaptopropionic acid Natural products CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 14
- SUWCVSZZLFOSJL-UHFFFAOYSA-N 3-sulfanyloxolan-2-one Chemical compound SC1CCOC1=O SUWCVSZZLFOSJL-UHFFFAOYSA-N 0.000 claims description 11
- 125000002947 alkylene group Chemical group 0.000 claims description 11
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 10
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 9
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- XYEDNYNWFGOEBD-UHFFFAOYSA-N 1-methyl-3-sulfanylpyrrolidin-2-one Chemical compound CN1CCC(S)C1=O XYEDNYNWFGOEBD-UHFFFAOYSA-N 0.000 claims description 7
- 125000004200 2-methoxyethyl group Chemical group [H]C([H])([H])OC([H])([H])C([H])([H])* 0.000 claims description 7
- XTMFNGWHWBKGNB-UHFFFAOYSA-N 2-sulfanylcyclopentan-1-one Chemical compound SC1CCCC1=O XTMFNGWHWBKGNB-UHFFFAOYSA-N 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 7
- 229910052717 sulfur Inorganic materials 0.000 claims description 7
- GIGXCOFIDQFKPS-UHFFFAOYSA-N 2-ethoxyethyl 3-sulfanylpropanoate Chemical compound CCOCCOC(=O)CCS GIGXCOFIDQFKPS-UHFFFAOYSA-N 0.000 claims description 5
- ZSVVABYVFGHFGR-UHFFFAOYSA-N 3-sulfanylazepan-2-one Chemical compound SC1CCCCNC1=O ZSVVABYVFGHFGR-UHFFFAOYSA-N 0.000 claims description 5
- CLWUQJHGNOFQHQ-UHFFFAOYSA-N 3-sulfanylpiperidin-2-one Chemical compound SC1CCCNC1=O CLWUQJHGNOFQHQ-UHFFFAOYSA-N 0.000 claims description 5
- JUHNSCTZYIBZNP-UHFFFAOYSA-N 5-ethyl-3-sulfanyloxolan-2-one Chemical compound CCC1CC(S)C(=O)O1 JUHNSCTZYIBZNP-UHFFFAOYSA-N 0.000 claims description 5
- KQMHPBZASSQUOI-UHFFFAOYSA-N 5-methyl-3-sulfanyloxolan-2-one Chemical compound CC1CC(S)C(=O)O1 KQMHPBZASSQUOI-UHFFFAOYSA-N 0.000 claims description 5
- YEGBSNMLLSWLOO-UHFFFAOYSA-N 1-methyl-3-sulfanylpiperidin-2-one Chemical compound CN1CCCC(S)C1=O YEGBSNMLLSWLOO-UHFFFAOYSA-N 0.000 claims description 4
- DQQRFOMJMVWLKB-UHFFFAOYSA-N 2-methoxyethyl 3-sulfanylpropanoate Chemical compound COCCOC(=O)CCS DQQRFOMJMVWLKB-UHFFFAOYSA-N 0.000 claims description 4
- GSDIICCYVAIIOY-UHFFFAOYSA-N 2-sulfanylcyclohexan-1-one Chemical compound SC1CCCCC1=O GSDIICCYVAIIOY-UHFFFAOYSA-N 0.000 claims description 4
- 125000004434 sulfur atom Chemical group 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- HNJBEVLQSNELDL-UHFFFAOYSA-N pyrrolidin-2-one Chemical compound O=C1CCCN1 HNJBEVLQSNELDL-UHFFFAOYSA-N 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 description 46
- 238000003786 synthesis reaction Methods 0.000 description 46
- 238000000034 method Methods 0.000 description 27
- 239000000243 solution Substances 0.000 description 25
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 239000007788 liquid Substances 0.000 description 17
- 239000003795 chemical substances by application Substances 0.000 description 16
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 16
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 230000000694 effects Effects 0.000 description 15
- 150000001875 compounds Chemical class 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 13
- 239000011521 glass Substances 0.000 description 12
- 238000003756 stirring Methods 0.000 description 12
- 239000000126 substance Substances 0.000 description 12
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 11
- 238000006243 chemical reaction Methods 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 239000008213 purified water Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- LSNNMFCWUKXFEE-UHFFFAOYSA-N Sulfurous acid Chemical class OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 8
- 230000002378 acidificating effect Effects 0.000 description 8
- 238000012937 correction Methods 0.000 description 8
- FHPVNTBXCQPWDY-UHFFFAOYSA-N 3-sulfanylpyrrolidin-2-one Chemical compound SC1CCNC1=O FHPVNTBXCQPWDY-UHFFFAOYSA-N 0.000 description 7
- 239000000654 additive Substances 0.000 description 7
- 238000002360 preparation method Methods 0.000 description 7
- 239000002994 raw material Substances 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 239000012855 volatile organic compound Substances 0.000 description 7
- 239000001993 wax Substances 0.000 description 7
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 6
- 238000009835 boiling Methods 0.000 description 6
- 231100000640 hair analysis Toxicity 0.000 description 6
- 238000005259 measurement Methods 0.000 description 6
- 230000007935 neutral effect Effects 0.000 description 6
- GEHJYWRUCIMESM-UHFFFAOYSA-L sodium sulfite Chemical compound [Na+].[Na+].[O-]S([O-])=O GEHJYWRUCIMESM-UHFFFAOYSA-L 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-L sulfite Chemical class [O-]S([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-L 0.000 description 6
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 5
- 150000001241 acetals Chemical class 0.000 description 5
- 239000008346 aqueous phase Substances 0.000 description 5
- 239000007864 aqueous solution Substances 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 238000001816 cooling Methods 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 239000003814 drug Substances 0.000 description 5
- 239000003205 fragrance Substances 0.000 description 5
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002596 lactones Chemical class 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 235000019198 oils Nutrition 0.000 description 5
- 229920002545 silicone oil Polymers 0.000 description 5
- 235000007586 terpenes Nutrition 0.000 description 5
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 description 4
- DMXVIRCAGMRKKJ-UHFFFAOYSA-N 2,4-dibromobutanoyl bromide Chemical compound BrCCC(Br)C(Br)=O DMXVIRCAGMRKKJ-UHFFFAOYSA-N 0.000 description 4
- NFFDSZJZQBYUKM-UHFFFAOYSA-N 3-bromo-1-methylpyrrolidin-2-one Chemical compound CN1CCC(Br)C1=O NFFDSZJZQBYUKM-UHFFFAOYSA-N 0.000 description 4
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 4
- BAVYZALUXZFZLV-UHFFFAOYSA-N Methylamine Chemical compound NC BAVYZALUXZFZLV-UHFFFAOYSA-N 0.000 description 4
- WQDUMFSSJAZKTM-UHFFFAOYSA-N Sodium methoxide Chemical compound [Na+].[O-]C WQDUMFSSJAZKTM-UHFFFAOYSA-N 0.000 description 4
- 239000002253 acid Substances 0.000 description 4
- 150000001298 alcohols Chemical class 0.000 description 4
- 239000000872 buffer Substances 0.000 description 4
- 239000002537 cosmetic Substances 0.000 description 4
- BNIILDVGGAEEIG-UHFFFAOYSA-L disodium hydrogen phosphate Chemical compound [Na+].[Na+].OP([O-])([O-])=O BNIILDVGGAEEIG-UHFFFAOYSA-L 0.000 description 4
- 229940079593 drug Drugs 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N glycine betaine Chemical compound C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 150000002366 halogen compounds Chemical class 0.000 description 4
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 4
- 238000009776 industrial production Methods 0.000 description 4
- 150000002894 organic compounds Chemical class 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 150000002989 phenols Chemical class 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 125000003161 (C1-C6) alkylene group Chemical group 0.000 description 3
- HPCYZQZHUNXJPG-UHFFFAOYSA-N 2,4-dibromo-n-methylbutanamide Chemical compound CNC(=O)C(Br)CCBr HPCYZQZHUNXJPG-UHFFFAOYSA-N 0.000 description 3
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 3
- GVPDRYJFYUWXQK-UHFFFAOYSA-N 3-bromopyrrolidin-2-one Chemical compound BrC1CCNC1=O GVPDRYJFYUWXQK-UHFFFAOYSA-N 0.000 description 3
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 3
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 3
- 241000402754 Erythranthe moschata Species 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 3
- 206010044625 Trichorrhexis Diseases 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 238000007605 air drying Methods 0.000 description 3
- 125000004183 alkoxy alkyl group Chemical group 0.000 description 3
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 239000004202 carbamide Substances 0.000 description 3
- 239000012295 chemical reaction liquid Substances 0.000 description 3
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- 230000000052 comparative effect Effects 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 238000001035 drying Methods 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
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
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- 229910052736 halogen Inorganic materials 0.000 description 3
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- 239000011593 sulfur Substances 0.000 description 3
- OOCCDEMITAIZTP-QPJJXVBHSA-N (E)-cinnamyl alcohol Chemical compound OC\C=C\C1=CC=CC=C1 OOCCDEMITAIZTP-QPJJXVBHSA-N 0.000 description 2
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- SPEUIVXLLWOEMJ-UHFFFAOYSA-N 1,1-dimethoxyethane Chemical compound COC(C)OC SPEUIVXLLWOEMJ-UHFFFAOYSA-N 0.000 description 2
- XDOFQFKRPWOURC-UHFFFAOYSA-N 16-methylheptadecanoic acid Chemical compound CC(C)CCCCCCCCCCCCCCC(O)=O XDOFQFKRPWOURC-UHFFFAOYSA-N 0.000 description 2
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- GWCRPYGYVRXVLI-UHFFFAOYSA-N 2-ethyl-4-hydroxy-5-methyl-3(2H)-furanone Chemical compound CCC1OC(C)=C(O)C1=O GWCRPYGYVRXVLI-UHFFFAOYSA-N 0.000 description 2
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- SYWTVQYXXCXVSX-UHFFFAOYSA-N 3,4-bis(sulfanyl)oxolan-2-one Chemical compound SC1COC(=O)C1S SYWTVQYXXCXVSX-UHFFFAOYSA-N 0.000 description 2
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- 238000002203 pretreatment Methods 0.000 description 1
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- 239000003223 protective agent Substances 0.000 description 1
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- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
Landscapes
- Cosmetics (AREA)
Description
本発明は、弱酸性から中性領域で使用可能で、くせ毛直しやカール伸ばし、カール形成など、毛髪の変形矯正に最適なシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースおよび頭髪用ジェルに関する。 The present invention can be used in mildly acidic to neutral regions, and is ideal for correcting hair deformation such as hair straightening, curling, curling , hair treatment, hair water, hair wax, hair mousse and hair For gels .
従来、くせ毛直しやカール伸ばし、カール形成などの毛髪の変形矯正に関して、亜硫酸塩や亜硫酸水素塩などを用いた毛髪処理剤が広く使用されてきた。これら亜硫酸塩や亜硫酸水素塩は、パーマネントウエーブ剤にも使用されるが、上記変形矯正用の毛髪処理剤では、パーマネントウエーブを目的とした場合と比べて処理剤中の亜硫酸塩や亜硫酸水素塩の濃度が低く、さらに極めて緩和な条件で使用するために毛髪の変形矯正の効果が不充分であった。 Conventionally, hair treatment agents using sulfites, bisulfites, and the like have been widely used for straightening hair deformation such as combing, curling and curling. These sulfites and bisulfites are also used in permanent waving agents. However, in the above-mentioned hair treatment agent for deformation correction, the sulfites and bisulfites in the treatment agents are less than those intended for permanent waving. The effect of correcting the deformation of hair was insufficient because it was used at a low concentration and under extremely mild conditions.
また、亜硫酸塩が酸性側で分解されやすいことから、亜硫酸塩を含む毛髪処理剤は通常、アルカリ性側に調整されており、そのアルカリ性のために毛髪の痛みや肌荒れなどの障害が生じるという問題もあった。 In addition, since sulfites are easily decomposed on the acidic side, hair treatment agents containing sulfites are usually adjusted to the alkaline side, and the problem of problems such as hair pain and rough skin occurs due to the alkalinity. there were.
このような問題を改善するための技術としては、例えば、亜硫酸塩や亜硫酸水素塩に加えてイミダゾリジンジオンを配合した毛髪処理用組成物(特許文献1)、亜硫酸塩や亜硫酸水素塩に加えて尿素およびアルコール類を配合した毛髪処理用組成物(特許文献2)などが提案されている。 As a technique for improving such a problem, for example, in addition to sulfite and bisulfite, a hair treatment composition containing imidazolidinedione (Patent Document 1), sulfite and bisulfite. A hair treatment composition containing urea and alcohols (Patent Document 2) has been proposed.
しかしながら、前者のイミダゾリジンジオンを配合する方法では、酢酸緩衝液の使用により酸性側での使用が明記されているものの、毛髪の変形矯正効果の向上はさして大きくない。また、後者の尿素およびアルコール類を添加する方法では、亜硫酸塩や亜硫酸水素塩の分解を抑制するために、アルカリ性での使用が記載されておりアルカリによる毛髪損傷の問題が依然として残される。
本発明は、皮膚や毛髪への刺激が少ない弱酸性から中性領域で使用可能なシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースおよび頭髪用ジェル、より詳しくは、くせ毛直しやカール伸ばし、カール形成など、毛髪の変形矯正に最適なシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースおよび頭髪用ジェルを提供することを目的としている。 The present invention relates to shampoos, rinses, conditioners, hair treatments, hair water, hair waxes, hair mousses and hair gels that can be used in mildly acidic to neutral areas with little irritation to the skin and hair. The object is to provide shampoos, rinses, conditioners, hair treatments, hair water, hair waxes, hair mousses and hair gels that are optimal for straightening hair deformation such as curling and curling.
本発明者らは上記実情に鑑みて鋭意研究を重ねた結果、特定のメルカプト化合物を含有する薬剤では、従来では充分な効果がみられなかったpH領域で、毛髪の変形矯正効果を有効に発揮することを見出し、本発明を完成するに至った。 As a result of intensive studies in view of the above circumstances, the present inventors have effectively demonstrated the effect of correcting hair deformation in a pH region where a sufficient effect has not been observed with a drug containing a specific mercapto compound. As a result, the present invention has been completed.
すなわち、本発明は、以下の[1]〜[23]の事項を含むものである。
[1]本発明の毛髪矯正剤は、下記式(1)または(2)で示されるメルカプト化合物の少なくとも1種を含有することを特徴としている;
That is, the present invention includes the following items [1] to [23].
[1] The hair straightener of the present invention is characterized by containing at least one mercapto compound represented by the following formula (1) or (2);
(式(1)中、Rは分岐を有していてもよい総炭素数1〜6のアルキレン基を表し、R2
は総炭素数3〜15のアルコキシアルキル基を表す。ただし、R2のアルキレン部分には
エーテル結合が含まれていてもよい。)
(In formula (1), R represents a C1-C6 alkylene group which may have a branch, and R < 2 >.
Represents an alkoxyalkyl group having 3 to 15 carbon atoms in total. However, the alkylene moiety of R 2 may contain an ether bond. )
(式(2)中、Xは単結合、−O−、−S−、−NH−、−NR4−のいずれかの構造を
表し、R4は炭素数1〜6のアルキル基を表す。Yは酸素原子または硫黄原子を表し、R3は少なくとも1つのメルカプト基を有する二価の有機残基を表す。)。
(In formula (2), X represents a single bond, a structure of —O—, —S—, —NH—, or —NR 4 —, and R 4 represents an alkyl group having 1 to 6 carbon atoms. Y represents an oxygen atom or a sulfur atom, and R 3 represents a divalent organic residue having at least one mercapto group.
[2]前記式(1)で示されるメルカプト化合物が、下記式(1a)で示される化合物であることを特徴とする上記[1]に記載の毛髪矯正剤; [2] The hair straightener according to the above [1], wherein the mercapto compound represented by the formula (1) is a compound represented by the following formula (1a);
(式(1a)中、R1は水素原子または炭素数1〜5のアルキル基を表し、R2は式(1)中のR2と同じ意味を表す。)。
[3]前記式(1a)のR1が、水素原子またはメチル基であることを特徴とする上記[2]に記載の毛髪矯正剤。
(In the formula (1a), R 1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R 2 has the same meaning as R 2 in the formula (1).).
[3] The hair straightener according to [2] above, wherein R 1 in the formula (1a) is a hydrogen atom or a methyl group.
[4]前記式(1a)のR2が、2−メトキシエチル基、2−エトキシエチル基、2−メ
トキシプロピル基、2−エトキシプロピル基、1−メトキシプロパン−2−イル基、1−エトキシプロパン−2−イル基、5−メトキシ−3−オキサペンチル基または5−エトキシ−3−オキサペンチル基のいずれかであることを特徴とする上記[2]または[3]に記載の毛髪矯正剤。
[4] R 2 in the formula (1a) is 2-methoxyethyl group, 2-ethoxyethyl group, 2-methoxypropyl group, 2-ethoxypropyl group, 1-methoxypropan-2-yl group, 1-ethoxy. The hair straightener according to [2] or [3] above, which is any one of a propan-2-yl group, a 5-methoxy-3-oxapentyl group, and a 5-ethoxy-3-oxapentyl group .
[5]前記式(1a)で示されるメルカプト化合物が、チオグリコール酸2−メトキシエチルエステル、チオグリコール酸2−エトキシエチルエステル、チオ乳酸2−メトキシエチルエステルまたはチオ乳酸2−エトキシエチルエステルのいずれかであることを特徴とする上記[2]に記載の毛髪矯正剤。 [5] The mercapto compound represented by the formula (1a) is any of thioglycolic acid 2-methoxyethyl ester, thioglycolic acid 2-ethoxyethyl ester, thiolactic acid 2-methoxyethyl ester, or thiolactic acid 2-ethoxyethyl ester. The hair straightener as described in [2] above, wherein
[6]前記式(1)で示されるメルカプト化合物が、下記式(1b)で示される化合物で
あることを特徴とする上記[1]に記載の毛髪矯正剤;
[6] The hair straightener according to the above [1], wherein the mercapto compound represented by the formula (1) is a compound represented by the following formula (1b);
(式(1b)中、R2は式(1)のR2と同じ意味を表す)。
[7]前記式(1b)のR2が、2−メトキシエチル基、2−エトキシエチル基、2−メ
トキシプロピル基、2−エトキシプロピル基、1−メトキシプロパン−2−イル基、1−エトキシプロパン−2−イル基、5−メトキシ−3−オキサペンチル基または5−エトキシ−3−オキサペンチル基のいずれかであることを特徴とする上記[6]に記載の毛髪矯正剤。
(In the formula (1b), R 2 has the same meaning as R 2 of formula (1)).
[7] R 2 in the formula (1b) is 2-methoxyethyl group, 2-ethoxyethyl group, 2-methoxypropyl group, 2-ethoxypropyl group, 1-methoxypropan-2-yl group, 1-ethoxy. The hair straightener according to [6] above, which is a propan-2-yl group, a 5-methoxy-3-oxapentyl group, or a 5-ethoxy-3-oxapentyl group.
[8]前記式(1b)で示されるメルカプト化合物が、3−メルカプトプロピオン酸2−メトキシエチルエステルまたは3−メルカプトプロピオン酸2−エトキシエチルエステルのいずれかであることを特徴とする上記[6]に記載の毛髪矯正剤。 [8] The mercapto compound represented by the formula (1b) is any one of 3-mercaptopropionic acid 2-methoxyethyl ester and 3-mercaptopropionic acid 2-ethoxyethyl ester, [6] The hair straightener described in 1.
[9]前記式(2)のXが、−O−、−NH−、−S−、または−N(CH3)−のいず
れかであることを特徴とする上記[1]に記載の毛髪矯正剤。
[10]前記式(2)のXが、単結合であることを特徴とする上記[1]に記載の毛髪矯正剤。
[9] X in the formula (2) is, -O -, - NH -, - S-, or -N (CH 3) - hair according to the above [1] which is characterized in that either Correction agent.
[10] The hair straightener according to [1] above, wherein X in the formula (2) is a single bond.
[11]前記式(2)のYが、酸素原子であることを特徴とする上記[1]、[9]、[10]のいずれかに記載の毛髪矯正剤。
[12]前記式(2)のR3が、少なくとも1つのメルカプト基を有するアルキレン基で
あることを特徴とする上記[1]および[9]〜[11]のいずれかに記載の毛髪矯正剤。
[11] The hair straightener according to any one of [1], [9], and [10] above, wherein Y in the formula (2) is an oxygen atom.
[12] The hair straightener according to any one of [1] and [9] to [11] above, wherein R 3 in the formula (2) is an alkylene group having at least one mercapto group .
[13]前記式(2)のYが酸素原子であり、R3が少なくとも1つのメルカプト基を有
するアルキレン基であるときに、前記R3のメルカプト基がカルボニル基のα位に結合し
ていることを特徴とする上記[1]、[9]、[10]のいずれかに記載の毛髪矯正剤。
[13] When Y in the formula (2) is an oxygen atom and R 3 is an alkylene group having at least one mercapto group, the mercapto group of R 3 is bonded to the α-position of the carbonyl group. The hair straightener according to any one of [1], [9], and [10] above.
[14]前記式(2)で示されるメルカプト化合物が、2−メルカプト−4−ブタノリド、2−メルカプト−4−メチル−4−ブタノリド、2−メルカプト−4−エチル−4−ブタノリド、2−メルカプト−4−ブチロラクタム、N−メチル−2−メルカプト−4−ブチロラクタム、2−メルカプト−5−バレロラクタム、N―メチル−2−メルカプト−5−バレロラクタムまたは2−メルカプト−6−ヘキサノラクタムのいずれかであることを特徴とする上記[1]に記載の毛髪矯正剤。 [14] The mercapto compound represented by the formula (2) is 2-mercapto-4-butanolide, 2-mercapto-4-methyl-4-butanolide, 2-mercapto-4-ethyl-4-butanolide, 2-mercapto. Any of -4-butyrolactam, N-methyl-2-mercapto-4-butyrolactam, 2-mercapto-5-valerolactam, N-methyl-2-mercapto-5-valerolactam or 2-mercapto-6-hexanolactam The hair straightener according to [1] above, wherein
[15]前記式(2)で示されるメルカプト化合物が、2−メルカプトシクロペンタノンまたは2−メルカプトシクロヘキサノンのいずれかであることを特徴とする上記[1]に記載の毛髪矯正剤。 [15] The hair straightener according to [1] above, wherein the mercapto compound represented by the formula (2) is either 2-mercaptocyclopentanone or 2-mercaptocyclohexanone.
[16]前記メルカプト化合物を0.1〜10質量%の量で含有することを特徴とする上記[1]〜[15]のいずれかに記載の毛髪矯正剤。
[17]pHが4.0〜7.5であることを特徴とする上記[1]〜[16]のいずれかに記載の毛髪矯正剤。
[16] The hair straightener according to any one of [1] to [15] above, which contains the mercapto compound in an amount of 0.1 to 10% by mass.
[17] The hair straightener according to any one of [1] to [16] above, wherein the pH is 4.0 to 7.5.
[18]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするシャンプー。
[19]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするリンス。
[20]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするコンディショナー。
[21]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするヘアトリートメント。
[22]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするヘアウオーター。
[23]上記[1]〜[17]のいずれかに記載の毛髪矯正剤を含有することを特徴とするヘアムース。
[18] A shampoo comprising the hair straightener according to any one of [1] to [17] above.
[19] A rinse comprising the hair straightener according to any one of [1] to [17].
[20] A conditioner comprising the hair straightener according to any one of [1] to [17].
[21] A hair treatment comprising the hair straightener according to any one of [1] to [17].
[22] A hair water comprising the hair straightener according to any one of [1] to [17].
[23] A hair mousse comprising the hair straightener according to any one of [1] to [17].
本発明のシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースまたは頭髪用ジェルによれば、弱酸性から弱アルカリ性までの広いpH領域において、優れた毛髪変形矯正効果を達成できる。とくに、弱酸性から中性のpH領域において、より一層優れた毛髪変形矯正能を発揮するため、本発明のシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースまたは頭髪用ジェルによれば、毛髪や皮膚へのダメージを大幅に低減すると共に、くせ毛直しやカール伸ばし、カール形成などを確実に行うことが可能である。従って、本発明のシャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムースまたは頭髪用ジェルは、くせ毛やカールなどの毛髪を変形させて矯正する、毛髪の変形矯正に極めて有用である。 According to the shampoo, rinse, conditioner, hair treatment, hair water, hair wax, hair mousse or hair gel of the present invention, an excellent hair deformation correction effect can be achieved in a wide pH range from weak acidity to weak alkalinity. In particular, the shampoo, rinse, conditioner, hair treatment, hair water, hair wax, hair mousse or hair gel of the present invention is used in order to demonstrate even more excellent hair deformation correction ability in a weakly acidic to neutral pH range. As a result, it is possible to greatly reduce damage to hair and skin and to reliably perform curly hair straightening, curling, curling, and the like. Therefore, the shampoo, rinse, conditioner, hair treatment, hair water, hair wax, hair mousse, or hair gel of the present invention is extremely useful for straightening hair deformation by deforming hair such as comb hair and curl.
以下、本発明について具体的に説明する。
本発明の毛髪矯正剤は、下記式(1)または(2)
Hereinafter, the present invention will be specifically described.
The hair straightener of the present invention has the following formula (1) or (2)
(式(1)中、Rは分岐を有していてもよい総炭素数1〜6のアルキレン基を表し、R2
は総炭素数3〜15のアルコキシアルキル基を表す。ただし、R2のアルキレン部分には
エーテル結合が含まれていてもよい。)
(In formula (1), R represents a C1-C6 alkylene group which may have a branch, and R < 2 >.
Represents an alkoxyalkyl group having 3 to 15 carbon atoms in total. However, the alkylene moiety of R 2 may contain an ether bond. )
(式(2)中、Xは単結合、−O−、−S−、−NH−、−NR4−のいずれかの構造を
表し、R4は炭素数1〜6のアルキル基を表す。Yは酸素原子または硫黄原子を表し、R3は少なくとも1つのメルカプト基を有する二価の有機残基を表す。)
で示されるメルカプト化合物の少なくとも1種を含有することを特徴としている。
(In formula (2), X represents a single bond, a structure of —O—, —S—, —NH—, or —NR 4 —, and R 4 represents an alkyl group having 1 to 6 carbon atoms. Y represents an oxygen atom or a sulfur atom, and R 3 represents a divalent organic residue having at least one mercapto group.)
It contains at least 1 sort (s) of the mercapto compound shown by these.
まず、これらのメルカプト化合物について説明する。
本発明の毛髪矯正剤に用いることのできるメルカプト化合物は、上記式(1)で示される化合物および/または式(2)で示される化合物である。
First, these mercapto compounds will be described.
The mercapto compound that can be used in the hair straightener of the present invention is a compound represented by the above formula (1) and / or a compound represented by the formula (2).
式(1)において、Rは、分岐を有していてもよい総炭素数1〜6のアルキレン基を表す。具体的には、例えば、メチレン基、エチレン基、メチルメチレン基、ジメチルメチレン基、エチルメチレン基、プロピルメチレン基、ブチルメチレン基、メチルエチレン基、ジメチルエチレン基、1,2−ジメチルエチレン基、プロピレン基、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基などが挙げられる。 In formula (1), R represents a C1-C6 alkylene group which may have a branch. Specifically, for example, methylene group, ethylene group, methylmethylene group, dimethylmethylene group, ethylmethylene group, propylmethylene group, butylmethylene group, methylethylene group, dimethylethylene group, 1,2-dimethylethylene group, propylene Group, tetramethylene group, pentamethylene group, hexamethylene group and the like.
また、R2は、総炭素数3〜15のアルコキシアルキル基を表す。ただし、R2のアルキレン部分にはエーテル結合が含まれていてもよい。R2の総炭素数は3〜10が好ましく
、さらには3〜8が工業的な原料入手の容易さから好ましい。R2に含まれる上記アルコ
キシ基部分の炭素数は1〜4が好ましく、アルキレン基部分の炭素数は1〜8が好ましい。具体的には、例えば、2−メトキシエチル、2−エトキシエチル、2−プロポキシエチル、2−イソプロポキシエチル、2−ブトキシエチル、2−イソブトキシエチル、2−tert−ブトキシエチル、1−メトキシプロパン−2−イル、1−エトキシプロパン−2−イル、1−プロポキシプロパン−2−イル、1−イソプロポキシプロパン−2−イル、1−ブトキシプロパン−2−イル、1−イソブトキシプロパン−2−イル、1−tert−ブトキシプロパン−2−イル、2−メトキシプロピル、2−エトキシプロピル、2−プロポキシプロピル、2−イソプロポキシプロピル、2−ブトキシプロピル、2−イソブトキシプロピル、2−tert−ブトキシプロピル、5−メトキシ−3−オキサペンチル、5−エトキシ−3−オキサペンチル、5−プロポキシ−3−オキサペンチル、5−イソプロポキシ−3−オキサペンチル、5−ブトキシ−3−オキサペンチル、5−イソブトキシ−3−オキサペンチル、5−tert−ブトキシ−3−オキサペンチル、8−メトキシ−3,6−ジオキサオクチル、8−エトキシ−3,6−ジオキサオクチル、8−プロポキシ−3,6−ジオキサオクチル、8−イソプロポキシ−3,6−ジオキサオクチル、8−ブトキシ−3,6−ジオキサオクチル、8−イソブトキシ−3,6−ジオキサオクチル、8−tert−ブトキシ−3,6−ジオキサオクチルなどが挙げられる。
R 2 represents an alkoxyalkyl group having 3 to 15 carbon atoms in total. However, the alkylene moiety of R 2 may contain an ether bond. The total carbon number of R 2 is preferably 3 to 10, and more preferably 3 to 8 because of easy availability of industrial raw materials. The alkoxy group portion contained in R 2 preferably has 1 to 4 carbon atoms, and the alkylene group portion preferably has 1 to 8 carbon atoms. Specifically, for example, 2-methoxyethyl, 2-ethoxyethyl, 2-propoxyethyl, 2-isopropoxyethyl, 2-butoxyethyl, 2-isobutoxyethyl, 2-tert-butoxyethyl, 1-methoxypropane 2-yl, 1-ethoxypropan-2-yl, 1-propoxypropan-2-yl, 1-isopropoxypropan-2-yl, 1-butoxypropan-2-yl, 1-isobutoxypropan-2- 1-tert-butoxypropan-2-yl, 2-methoxypropyl, 2-ethoxypropyl, 2-propoxypropyl, 2-isopropoxypropyl, 2-butoxypropyl, 2-isobutoxypropyl, 2-tert-butoxy Propyl, 5-methoxy-3-oxapentyl, 5-ethoxy-3-oxapentyl, 5-propo Si-3-oxapentyl, 5-isopropoxy-3-oxapentyl, 5-butoxy-3-oxapentyl, 5-isobutoxy-3-oxapentyl, 5-tert-butoxy-3-oxapentyl, 8-methoxy- 3,6-dioxaoctyl, 8-ethoxy-3,6-dioxaoctyl, 8-propoxy-3,6-dioxaoctyl, 8-isopropoxy-3,6-dioxaoctyl, 8-butoxy-3 , 6-dioxaoctyl, 8-isobutoxy-3,6-dioxaoctyl, 8-tert-butoxy-3,6-dioxaoctyl and the like.
式(1)で示される化合物として、より具体的には、下記式(1a)、(1b)で示される化合物が好ましく挙げられる。 More specifically, preferred examples of the compound represented by the formula (1) include compounds represented by the following formulas (1a) and (1b).
(式(1a)中、R1は水素原子または炭素数1〜5のアルキル基を表し、R2は式(1)中のR2と同じ意味を表す。) (Formula (1a), R 1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, R 2 has the same meaning as R 2 in the formula (1).)
(式(1b)中、R2は式(1)のR2と同じ意味を表す。)。
上記式(1a)においてR1は水素原子または炭素数1〜5のアルキル基を表し、好ま
しくは水素原子、またはメチル基、エチル基、プロピル基、ブチル基などの炭素数1〜4のアルキル基である。これらの中では、工業的な原料入手の容易さから、水素原子、メチル基およびエチル基がより好ましく、水素原子およびメチル基がさらに好ましい。
(In the formula (1b), R 2 has the same meaning as R 2 of formula (1).).
In the above formula (1a), R 1 represents a hydrogen atom or an alkyl group having 1 to 5 carbon atoms, preferably a hydrogen atom or an alkyl group having 1 to 4 carbon atoms such as a methyl group, an ethyl group, a propyl group, or a butyl group. It is. In these, a hydrogen atom, a methyl group, and an ethyl group are more preferable, and a hydrogen atom and a methyl group are more preferable from the ease of industrial raw material acquisition.
R2は、上記式(1)と同じである。R2の具体例としては、式(1)において上述したものと同じものが挙げられるが、その中でも工業的な原料入手の容易さの点から、2−メトキシエチル、2−エトキシエチル、2−プロポキシエチル、2−メトキシ−1−メチルエチル、2−エトキシ−1−メチルエチル、2−メトキシプロピル、2−エトキシプロピル、5−メトキシ−3−オキサペンチル、5−エトキシ−3−オキサペンチルが好ましく、2−メトキシエチル、2−エトキシエチル、2−メトキシプロピル、2−エトキシプロピル、1−メトキシプロパン−2−イル、1−エトキシプロパン−2−イル、5−メトキシ−3−オキサペンチル、5−エトキシ−3−オキサペンチルがより好ましい。 R 2 is the same as in the above formula (1). Specific examples of R 2 include the same as those described above in formula (1). Among them, 2-methoxyethyl, 2-ethoxyethyl, 2- Propoxyethyl, 2-methoxy-1-methylethyl, 2-ethoxy-1-methylethyl, 2-methoxypropyl, 2-ethoxypropyl, 5-methoxy-3-oxapentyl and 5-ethoxy-3-oxapentyl are preferred. 2-methoxyethyl, 2-ethoxyethyl, 2-methoxypropyl, 2-ethoxypropyl, 1-methoxypropan-2-yl, 1-ethoxypropan-2-yl, 5-methoxy-3-oxapentyl, 5- More preferred is ethoxy-3-oxapentyl.
式(1a)で示されるメルカプト化合物の具体例としては、例えば、チオグリコール酸2−メトキシエチルエステル、チオグリコール酸2−エトキシエチルエステル、チオグリコール酸2−メトキシプロピルエステル、チオグリコール酸2−エトキシプロピルエステル、チオ乳酸2−メトキシエチルエステル、チオ乳酸2−エトキシエチルエステル、チオ乳酸2−メトキシプロピルエステル、チオ乳酸2−エトキシプロピルエステルなどが挙げられる。 Specific examples of the mercapto compound represented by the formula (1a) include, for example, thioglycolic acid 2-methoxyethyl ester, thioglycolic acid 2-ethoxyethyl ester, thioglycolic acid 2-methoxypropyl ester, thioglycolic acid 2-ethoxy Examples include propyl ester, thiolactic acid 2-methoxyethyl ester, thiolactic acid 2-ethoxyethyl ester, thiolactic acid 2-methoxypropyl ester, and thiolactic acid 2-ethoxypropyl ester.
これらの中でも、チオグリコール酸2−メトキシエチルエステル、チオグリコール酸2−エトキシエチルエステル、チオ乳酸2−メトキシエチルエステル、チオ乳酸2−エトキシエチルエステルが毛髪矯正性能及び工業的な製造の容易さの点で好ましい。 Among these, thioglycolic acid 2-methoxyethyl ester, thioglycolic acid 2-ethoxyethyl ester, thiolactic acid 2-methoxyethyl ester, and thiolactic acid 2-ethoxyethyl ester are excellent in hair straightening performance and industrial production ease. This is preferable.
式(1b)においてR2は上記式(1)のR2と同じである。
式(1b)で示されるメルカプト化合物の具体例としては、3−メルカプトプロピオン酸2−メトキシエチルエステル、3−メルカプトプロピオン酸2−エトキシエチルエステル、3−メルカプトプロピオン酸2−メトキシプロピルエステル、3−メルカプトプロピオン酸2−エトキシプロピルエステルなどが挙げられる。
R 2 in the formula (1b) is the same as R 2 in the formula (1).
Specific examples of the mercapto compound represented by the formula (1b) include 3-mercaptopropionic acid 2-methoxyethyl ester, 3-mercaptopropionic acid 2-ethoxyethyl ester, 3-mercaptopropionic acid 2-methoxypropyl ester, 3- Examples include mercaptopropionic acid 2-ethoxypropyl ester.
これらの中でも、3−メルカプトプロピオン酸2−メトキシエチルエステル、3−メルカプトプロピオン酸2−エトキシエチルエステルが毛髪矯正性能及び工業的な製造の容易さの点で好ましい。 Among these, 3-mercaptopropionic acid 2-methoxyethyl ester and 3-mercaptopropionic acid 2-ethoxyethyl ester are preferable in terms of hair straightening performance and ease of industrial production.
このような式(1)で示されるメルカプト化合物、より具体的には式(1a)、式(1b)で示されるメルカプトカルボン酸アルコキシアルキルエステルは、市販のチオカルボン酸エステル、あるいは、より入手容易なチオカルボン酸を原料として鉱酸や有機酸などの酸触媒存在下にモノアルコキシアルキルアルコールと混合加熱することにより合成することができる。 Such a mercapto compound represented by the formula (1), more specifically, a mercaptocarboxylic acid alkoxyalkyl ester represented by the formula (1a) or (1b) is a commercially available thiocarboxylic acid ester or more easily available. It can be synthesized by mixing and heating with monoalkoxyalkyl alcohol using thiocarboxylic acid as a raw material in the presence of an acid catalyst such as mineral acid or organic acid.
一方、式(2)において、Xは単結合、−O−、−S−、−NH−、−NR4−のいず
れかの構造を表し、R4は炭素数1〜6のアルキル基を表す。R4としては、毛髪への浸透性向上の点でメチル基、エチル基が好ましく、特に工業的な原料入手の容易さの点でメチル基が好ましい。なお、水あるいは水溶液への溶解度が比較的高く、剤の調製が容易である点からは、Xとしては、−O−、−NH−、−NR4−が好ましい。
On the other hand, in Formula (2), X represents a single bond, a structure of —O—, —S—, —NH—, or —NR 4 —, and R 4 represents an alkyl group having 1 to 6 carbon atoms. . R 4 is preferably a methyl group or an ethyl group from the viewpoint of improving the permeability to hair, and particularly preferably a methyl group from the viewpoint of easy availability of industrial raw materials. In view of relatively high solubility in water or an aqueous solution and easy preparation of the agent, X is preferably —O—, —NH—, or —NR 4 —.
Yは、酸素原子または硫黄原子を表すが、工業的な原料入手の容易さの点で酸素原子が好ましい。
R3は少なくとも1つのメルカプト基(−SH)を有する二価の有機残基を表す。R3は少なくとも1つのメルカプト基を有する二価の有機残基であれば特に限定されないが、少なくとも1つのメルカプト基を有するアルキレン基が好ましい。少なくとも1つのメルカプト基を有するアルキレン基としては、少なくとも1つのメルカプト基を有し、分岐を有していてもよく、主鎖の炭素数が2〜6のアルキレン基が好ましく挙げられる。Xが−O−、−S−、−NH−、−NR4−のいずれかである場合には、原料入手の容易さの点か
ら、さらに好ましいR3として、少なくとも1つのメルカプト基を有するエチレン基及び
プロピレン基が挙げられる。
Y represents an oxygen atom or a sulfur atom, and an oxygen atom is preferable from the viewpoint of easy availability of industrial raw materials.
R 3 represents a divalent organic residue having at least one mercapto group (—SH). R 3 is not particularly limited as long as it is a divalent organic residue having at least one mercapto group, but is preferably an alkylene group having at least one mercapto group. As the alkylene group having at least one mercapto group, an alkylene group having at least one mercapto group, optionally having a branch, and having 2 to 6 carbon atoms in the main chain is preferably exemplified. When X is any of —O—, —S—, —NH—, and —NR 4 —, ethylene having at least one mercapto group is more preferable as R 3 from the viewpoint of easy availability of raw materials. Groups and propylene groups.
二価の有機残基が有するメルカプト基の数は、工業的製造の容易さおよび毛髪矯正剤調製時の取り扱い性の点から1〜3が好ましく、更に好ましくは1〜2である。
また、二価の有機残基が有するメルカプト基の位置は限定されず、メルカプト基は直接二価の有機残基に結合していてもよく、さらにアルキレン基などを介して結合していてもよい(例えばメルカプトエチル基)が、Yが酸素原子である場合には、−CY−で表されるカルボニル基のα位にある炭素原子(該炭素原子は前記二価の有機残基を構成する炭素原子である)にメルカプト基が結合していることが、工業的製造の容易さおよび毛髪変形矯正性能の点から好ましい。
The number of mercapto groups possessed by the divalent organic residue is preferably 1 to 3, more preferably 1 to 2 from the viewpoint of ease of industrial production and handling at the time of preparing a hair straightener.
Further, the position of the mercapto group possessed by the divalent organic residue is not limited, and the mercapto group may be directly bonded to the divalent organic residue, or may be further bonded via an alkylene group or the like. When Y is an oxygen atom (for example, a mercaptoethyl group), the carbon atom at the α-position of the carbonyl group represented by —CY— (the carbon atom is a carbon constituting the divalent organic residue). It is preferable that a mercapto group is bonded to (which is an atom) from the viewpoint of easy industrial production and hair deformation correction performance.
式(2)において、Xが−O−、−S−、−NH−、−NR4−のいずれかである場合
のメルカプト化合物の具体例としては、3−メルカプト−4−ブタノリド、2,3−ジメルカプト−4−ブタノリド、2,4−ジメルカプト−4−ブタノリド、3,4−ジメルカプト−4−ブタノリド、3−メルカプト−4−ブチロチオラクトン、3−メルカプト−4−ブチロラクタム、2,3−ジメルカプト−4−ブチロラクタム、2,4−ジメルカプト−4−ブチロラクタム、3,4−ジメルカプト−4−ブチロラクタム、3−メルカプト−5−ペンタノリド、4−メルカプト−5−ペンタノリド、2,3−ジメルカプト−5−ペンタノリド、2,4−ジメルカプト−5−ペンタノリド、2,5−ジメルカプト−5−ペンタノリド、3,4−ジメルカプト−5−ペンタノリド、3−メルカプト−5−バレロチオラクトン、3−メルカプト−5−バレロラクタム、4−メルカプト−5−バレロラクタム、2,3−ジメルカプト−5−バレロラクタム、2,4−ジメルカプト−5−バレロラクタム、2,5−ジメルカプト−5−バレロラクタム、
In the formula (2), specific examples of the mercapto compound when X is any of —O—, —S—, —NH—, and —NR 4 — include 3-mercapto-4-butanolide, 2,3 -Dimercapto-4-butanolide, 2,4-dimercapto-4-butanolide, 3,4-dimercapto-4-butanolide, 3-mercapto-4-butyrothiolactone, 3-mercapto-4-butyrolactam, 2,3- Dimercapto-4-butyrolactam, 2,4-dimercapto-4-butyrolactam, 3,4-dimercapto-4-butyrolactam, 3-mercapto-5-pentanolide, 4-mercapto-5-pentanolide, 2,3-dimercapto-5 Pentanolide, 2,4-dimercapto-5-pentanolide, 2,5-dimercapto-5-pentanolide, 3,4-dimerca To-5-pentanolide, 3-mercapto-5-valerothiolactone, 3-mercapto-5-valerolactam, 4-mercapto-5-valerolactam, 2,3-dimercapto-5-valerolactam, 2,4-dimercapto -5-valerolactam, 2,5-dimercapto-5-valerolactam,
3−メルカプト−6−ヘキサノリド、4−メルカプト−6−ヘキサノリド、5−メルカプト−6−ヘキサノリド、2,3−ジメルカプト−6−ヘキサノリド、2,4−ジメルカプト−6−ヘキサノリド、2,5−ジメルカプト−6−ヘキサノリド、3−メルカプト−6−ヘキサノラクタム、4−メルカプト−6−ヘキサノラクタム、5−メルカプト−6−ヘキサノラクタム、2,3−ジメルカプト−6−ヘキサノラクタム、2,4−ジメルカプト−6−ヘキサノラクタム、2,5−ジメルカプト−6−ヘキサノラクタム、2−メルカプト−3−プロピオラクトン、2−メルカプト−2−メチル−3−プロピオラクトン、2−メルカプト−3−メチル−3−プロピオラクトン、2−メルカプト−3−エチル−3−プロピオラクトン、2−メルカプト−2,3−ジメチル−3−プロピオラクトン、2−メルカプト−3−プロピオラクタム、2−メルカプト−2−メチル−3−プロピオラクタム、2−メルカプト−3−メチル−3−プロピオラクタム、2−メルカプト−3−エチル−3−プロピオラクタム、2−メルカプト−2,3−ジメチル−3−プロピオラクタム、 3-mercapto-6-hexanolide, 4-mercapto-6-hexanolide, 5-mercapto-6-hexanolide, 2,3-dimercapto-6-hexanolide, 2,4-dimercapto-6-hexanolide, 2,5-dimercapto- 6-hexanolide, 3-mercapto-6-hexanolactam, 4-mercapto-6-hexanolactam, 5-mercapto-6-hexanolactam, 2,3-dimercapto-6-hexanolactam, 2,4- Dimercapto-6-hexanolactam, 2,5-dimercapto-6-hexanolactam, 2-mercapto-3-propiolactone, 2-mercapto-2-methyl-3-propiolactone, 2-mercapto-3- Methyl-3-propiolactone, 2-mercapto-3-ethyl-3-propiolactone, 2-merca To-2,3-dimethyl-3-propiolactone, 2-mercapto-3-propiolactam, 2-mercapto-2-methyl-3-propiolactam, 2-mercapto-3-methyl-3-propio Lactam, 2-mercapto-3-ethyl-3-propiolactam, 2-mercapto-2,3-dimethyl-3-propiolactam,
2−メルカプト−3−プロピオチオラクトン、2−メルカプト−2−メチル−3−プロピオチオラクトン、2−メルカプト−3−メチル−3−プロピオチオラクトン、2−メルカプト−3−エチル−3−プロピオチオラクトン、2−メルカプト−2,3−ジメチル−3−プロピオチオラクトン、2−メルカプト−4−ブタノリド、2−メルカプト―2−メチル−4,4−ジメチル−4−ブタノリド、2−メルカプト−3−(2−プロペニル)−4−ブタノリド、2−メルカプト−4−メチル−4−ブタノリド、2−メルカプト−2−メ
チル−4−ブタノリド、2−メルカプト−3−メチル−4−ブタノリド、2−メルカプト−4−メチル−4−ブタノリド、2−メルカプト−3,4−ジメチル−4−ブタノリド、2−メルカプト−2−エチル−4−ブタノリド、2−メルカプト−3−エチル−4−ブタノリド、2−メルカプト−4−エチル−4−ブタノリド、2−メルカプト−4−ブチロチオラクトン、2−メルカプト−2−メチル−4−ブチロチオラクトン、2−メルカプト−3−メチル−4−ブチロチオラクトン、2−メルカプト−4−メチル−4−ブチロチオラクトン、2−メルカプト−3,4−ジメチル−4−ブチロチオラクトン、2−メルカプト−2−エチル−4−ブチロチオラクトン、2−メルカプト−3−エチル−4−ブチロチオラクトン、2−メルカプト−4−エチル−4−ブチロチオラクトン、
2-mercapto-3-propiothiolactone, 2-mercapto-2-methyl-3-propiothiolactone, 2-mercapto-3-methyl-3-propiothiolactone, 2-mercapto-3-ethyl-3 -Propiothiolactone, 2-mercapto-2,3-dimethyl-3-propiothiolactone, 2-mercapto-4-butanolide, 2-mercapto-2-methyl-4,4-dimethyl-4-butanolide, 2, -Mercapto-3- (2-propenyl) -4-butanolide, 2-mercapto-4-methyl-4-butanolide, 2-mercapto-2-methyl-4-butanolide, 2-mercapto-3-methyl-4-butanolide 2-mercapto-4-methyl-4-butanolide, 2-mercapto-3,4-dimethyl-4-butanolide, 2-mercapto-2-ethyl 4-butanolide, 2-mercapto-3-ethyl-4-butanolide, 2-mercapto-4-ethyl-4-butanolide, 2-mercapto-4-butyrothiolactone, 2-mercapto-2-methyl-4-buty Rothiolactone, 2-mercapto-3-methyl-4-butyrothiolactone, 2-mercapto-4-methyl-4-butyrothiolactone, 2-mercapto-3,4-dimethyl-4-butyrothiolactone 2-mercapto-2-ethyl-4-butyrothiolactone, 2-mercapto-3-ethyl-4-butyrothiolactone, 2-mercapto-4-ethyl-4-butyrothiolactone,
2−メルカプト−4−ブチロラクタム、2−メルカプト−2−メチル−4−ブチロラクタム、2−メルカプト−3−メチル−4−ブチロラクタム、2−メルカプト−4−メチル−4−ブチロラクタム、2−メルカプト−3,4−ジメチル−4−ブチロラクタム、2−メルカプト−2−エチル−4−ブチロラクタム、2−メルカプト−3−エチル−4−ブチロラクタム、2−メルカプト−4−エチル−4−ブチロラクタム、2−メルカプト−5−ペンタノリド、2−メルカプト−2−メチル−5−ペンタノリド、2−メルカプト−3−メチル−5−ペンタノリド、2−メルカプト−4−メチル−5−ペンタノリド、2−メルカプト−5−メチル−5−ペンタノリド、2−メルカプト−2−エチル−5−ペンタノリド、2−メルカプト−3−エチル−5−ペンタノリド、2−メルカプト−4−エチル−5−ペンタノリド、2−メルカプト−5−エチル−5−ペンタノリド、2−メルカプト−5−バレロラクタム、2−メルカプト−2−メチル−5−バレロラクタム、2−メルカプト−3−メチル−5−バレロラクタム、2−メルカプト−4−メチル−5−バレロラクタム、2−メルカプト−5−メチル−5−バレロラクタム、2−メルカプト−2−エチル−5−バレロラクタム、2−メルカプト−3−エチル−5−バレロラクタム、2−メルカプト−4−エチル−5−バレロラクタム、2−メルカプト−5−エチル−5−バレロラクタム、 2-mercapto-4-butyrolactam, 2-mercapto-2-methyl-4-butyrolactam, 2-mercapto-3-methyl-4-butyrolactam, 2-mercapto-4-methyl-4-butyrolactam, 2-mercapto-3, 4-dimethyl-4-butyrolactam, 2-mercapto-2-ethyl-4-butyrolactam, 2-mercapto-3-ethyl-4-butyrolactam, 2-mercapto-4-ethyl-4-butyrolactam, 2-mercapto-5 Pentanolide, 2-mercapto-2-methyl-5-pentanolide, 2-mercapto-3-methyl-5-pentanolide, 2-mercapto-4-methyl-5-pentanolide, 2-mercapto-5-methyl-5-pentanolide, 2-mercapto-2-ethyl-5-pentanolide, 2-mercapto-3-ethyl -5-pentanolide, 2-mercapto-4-ethyl-5-pentanolide, 2-mercapto-5-ethyl-5-pentanolide, 2-mercapto-5-valerolactam, 2-mercapto-2-methyl-5-valerolactam 2-mercapto-3-methyl-5-valerolactam, 2-mercapto-4-methyl-5-valerolactam, 2-mercapto-5-methyl-5-valerolactam, 2-mercapto-2-ethyl-5 Valerolactam, 2-mercapto-3-ethyl-5-valerolactam, 2-mercapto-4-ethyl-5-valerolactam, 2-mercapto-5-ethyl-5-valerolactam,
2−メルカプト−5−バレロチオラクトン、2−メルカプト−2−メチル−5−バレロチオラクトン、2−メルカプト−3−メチル−5−バレロチオラクトン、2−メルカプト−4−メチル−5−バレロチオラクトン、2−メルカプト−5−メチル−5−バレロチオラクトン、2−メルカプト−2−エチル−5−バレロチオラクトン、2−メルカプト−3−エチル−5−バレロチオラクトン、2−メルカプト−4−エチル−5−バレロチオラクトン、2−メルカプト−5−エチル−5−バレロチオラクトン、2−メルカプト−6−ヘキサノリド、2−メルカプト−2−メチル−6−ヘキサノリド、2−メルカプト−3−メチル−6−ヘキサノリド、2−メルカプト−4−メチル−6−ヘキサノリド、2−メルカプト−5−メチル−6−ヘキサノリド、2−メルカプト−6−メチル−6−ヘキサノリド、2−メルカプト−6−ヘキサノラクタム、2−メルカプト−2−メチル−6−ヘキサノラクタム、2−メルカプト−3−メチル−6−ヘキサノラクタム、2−メルカプト−4−メチル−6−ヘキサノラクタム、2−メルカプト−5−メチル−6−ヘキサノラクタム、2−メルカプト−6−メチル−6−ヘキサノラクタム、2−メルカプト−6−ヘキサノチオラクトン、2−メルカプト−2−メチル−6−ヘキサノチオラクトン、2−メルカプト−3−メチル−6−ヘキサノチオラクトン、2−メルカプト−4−メチル−6−ヘキサノチオラクトン、2−メルカプト−5−メチル−6−ヘキサノチオラクトン、2−メルカプト−6−メチル−6−ヘキサノチオラクトンおよび、これらラクタム類のN−メチルあるいはN−エチル誘導体などが挙げられる。 2-mercapto-5-valerothiolactone, 2-mercapto-2-methyl-5-valerothiolactone, 2-mercapto-3-methyl-5-valerothiolactone, 2-mercapto-4-methyl-5-valerothio Lactone, 2-mercapto-5-methyl-5-valerothiolactone, 2-mercapto-2-ethyl-5-valerothiolactone, 2-mercapto-3-ethyl-5-valerothiolactone, 2-mercapto-4- Ethyl-5-valerothiolactone, 2-mercapto-5-ethyl-5-valerothiolactone, 2-mercapto-6-hexanolide, 2-mercapto-2-methyl-6-hexanolide, 2-mercapto-3-methyl- 6-hexanolide, 2-mercapto-4-methyl-6-hexanolide, 2-mercapto-5-methyl-6-hexa Lido, 2-mercapto-6-methyl-6-hexanolide, 2-mercapto-6-hexanolactam, 2-mercapto-2-methyl-6-hexanolactam, 2-mercapto-3-methyl-6-hexano Lactam, 2-mercapto-4-methyl-6-hexanolactam, 2-mercapto-5-methyl-6-hexanolactam, 2-mercapto-6-methyl-6-hexanolactam, 2-mercapto-6 Hexanothiolactone, 2-mercapto-2-methyl-6-hexanothiolactone, 2-mercapto-3-methyl-6-hexanothiolactone, 2-mercapto-4-methyl-6-hexanothiolactone, 2-mercapto- 5-methyl-6-hexanothiolactone, 2-mercapto-6-methyl-6-hexanothiolactone, and these Such as N- methyl or N- ethyl derivative Kutamu acids and the like.
これらの中でも、2−メルカプト−4−ブタノリド、2−メルカプト−4−ブチロチオラクトン、2−メルカプト−4−ブチロラクタム、N―メチル−2−メルカプト−4−ブチロラクタム、2−メルカプト−4−メチル−4−ブタノリド、2−メルカプト−4−エチル−4−ブタノリド、2−メルカプト−5−ペンタノリド、2−メルカプト−5−バレロラクタム、N−メチル−2−メルカプト−5−バレロラクタム、2−メルカプト−6−
ヘキサノラクタム、3−メルカプト−4−ブタノリド、2,3−ジメルカプト−4−ブタノリド、2,4−ジメルカプト−4−ブタノリド、3−メルカプト−4−ブチロラクタム、2,3−ジメルカプト−4−ブチロラクタム、2,4−ジメルカプト−4−ブチロラクタム、2,3−ジメルカプト−5−ペンタノリド、2,4−ジメルカプト−5−ペンタノリド、2,5−ジメルカプト−5−ペンタノリド、3−メルカプト−5−バレロラクタム、4−メルカプト−5−バレロラクタム、2,3−ジメルカプト−5−バレロラクタム、2,4−ジメルカプト−5−バレロラクタム、2,5−ジメルカプト−5−バレロラクタムが好ましい。さらには2−メルカプト−4−ブタノリド、2−メルカプト−4−メチル−4−ブタノリド、2−メルカプト−4−エチル−4−ブタノリド、2−メルカプト−4−ブチロラクタム、N−メチル−2−メルカプト−4−ブチロラクタム、2−メルカプト−5−バレロラクタム、N―メチル−2−メルカプト−5−バレロラクタム及び2−メルカプト−6−ヘキサノラクタムが毛髪矯正性能及び工業的な原料入手の容易さから特に好ましい。
Among these, 2-mercapto-4-butanolide, 2-mercapto-4-butyrothiolactone, 2-mercapto-4-butyrolactam, N-methyl-2-mercapto-4-butyrolactam, 2-mercapto-4-methyl -4-butanolide, 2-mercapto-4-ethyl-4-butanolide, 2-mercapto-5-pentanolide, 2-mercapto-5-valerolactam, N-methyl-2-mercapto-5-valerolactam, 2-mercapto -6
Hexanolactam, 3-mercapto-4-butanolide, 2,3-dimercapto-4-butanolide, 2,4-dimercapto-4-butanolide, 3-mercapto-4-butyrolactam, 2,3-dimercapto-4-butyrolactam, 2,4-dimercapto-4-butyrolactam, 2,3-dimercapto-5-pentanolide, 2,4-dimercapto-5-pentanolide, 2,5-dimercapto-5-pentanolide, 3-mercapto-5-valerolactam, 4 -Mercapto-5-valerolactam, 2,3-dimercapto-5-valerolactam, 2,4-dimercapto-5-valerolactam and 2,5-dimercapto-5-valerolactam are preferred. Furthermore, 2-mercapto-4-butanolide, 2-mercapto-4-methyl-4-butanolide, 2-mercapto-4-ethyl-4-butanolide, 2-mercapto-4-butyrolactam, N-methyl-2-mercapto- 4-butyrolactam, 2-mercapto-5-valerolactam, N-methyl-2-mercapto-5-valerolactam and 2-mercapto-6-hexanolactam are particularly preferred because of their hair straightening performance and industrial availability. preferable.
これら式(2)で示されるメルカプト化合物は、既知の方法に準じて製造可能である。例えば、ラクトン化合物、ラクタム化合物をハロゲン化化合物としたのちにメルカプト基を導入することで合成できる。 These mercapto compounds represented by the formula (2) can be produced according to known methods. For example, it can be synthesized by introducing a mercapto group after using a lactone compound or a lactam compound as a halogenated compound.
具体的には、メルカプトラクトン及びメルカプトチオラクトンの合成では、まず、市販のラクトンあるいはチオラクトンを使用して、J.Am.Chem.Soc.1945,.67.2218−2220に記載された方法によりハロゲン体を合成する。合成したハロゲン体あるいは市販で入手可能なハロゲン体をAnn.1960,639.146−56に記載された方法に準じて反応させることでラクトン誘導体が合成できる。 Specifically, in the synthesis of mercaptolactone and mercaptothiolactone, first, a commercially available lactone or thiolactone is used. Am. Chem. Soc. 1945,. The halogen compound is synthesized by the method described in 67.2218-2220. Synthetic halogen compounds or commercially available halogen compounds are described in Ann. A lactone derivative can be synthesized by reacting according to the method described in 1960, 639.146-56.
メルカプトラクタム類は、J.Am.Chem.Soc.1958.80.6233−6237に記載された方法に準じて合成して得られるハロゲン化合物をラクトン類と同様にAnn.1960,639.146−56に記載された方法に準じて反応させることによりラクタム誘導体として合成できる。 Mercaplactams are described in J. Org. Am. Chem. Soc. 1958.80.6233-6237, a halogen compound obtained by synthesizing according to the method described in Ann. 1960, 639.146-56 can be synthesized as a lactam derivative by reacting according to the method described in 1960.
また、上記式(2)で示されるメルカプト化合物として、原料入手の容易さの点からは、Xが単結合である態様も好ましい。なお、Xが単結合である場合には、式(2)で示される化合物は、下記式(2a)で示される化合物となる。 In addition, as the mercapto compound represented by the above formula (2), an embodiment in which X is a single bond is preferable from the viewpoint of easy availability of raw materials. In addition, when X is a single bond, the compound represented by the formula (2) is a compound represented by the following formula (2a).
式(2a)において、YおよびR3は、式(2)と同じである。Xが単結合である場合
の好ましいR3の例としては、少なくとも1つのメルカプト基を有するブチレン基及びペ
ンチレン基が挙げられる。メルカプト基の数は、取り扱いや製造の容易さの点から1〜2が好ましい。
In the formula (2a), Y and R 3 are the same as those in the formula (2). Preferred examples of R 3 when X is a single bond include a butylene group and a pentylene group having at least one mercapto group. The number of mercapto groups is preferably 1 to 2 from the viewpoint of ease of handling and production.
式(2a)で示されるメルカプト化合物の具体例としては、2−メルカプトシクロペンタノン、3−メルカプトシクロペンタノン、2−メルカプトシクロヘキサノン、3−メルカプトシクロヘキサノン、2−メルカプトシクロヘプタノン、3−メルカプトシクロヘプ
タノン、2−メルカプトシクロオクタノン、3−メルカプトシクロオクタノン、2−メルカプト−テトラヒドロピラン−4−オン、3−メルカプト−テトラヒドロピラン−4−オン、2−メルカプト−テトラヒドロチオピラン−4−オン、3−メルカプト−テトラヒドロチオピラン−4−オン、4−メルカプト−テトラヒドロチオフェン−3−オン、5−メルカプト−3−ピロリドン、5−メルカプト−N−メチル−3−ピロリドン、4−メルカプト−テトラヒドロピラン−3−オン、5−メルカプト−テトラヒドロピラン−3−オン、3−メルカプト−テトラヒドロピラン−4−オン、4−メルカプト−3−ピペリドン、5−メルカプト−3−ピペリドン、3−メルカプト−4−ピペリドン、4−メルカプト−N−メチル−3−ピペリドン、5−メルカプト−N−メチル−3−ピペリドン、3−メルカプト−N−メチル−4−ピペリドンが挙げられる。これらの中でも2−メルカプトシクロペンタノン及び2−メルカプトシクロヘキサノンが好ましい。
Specific examples of the mercapto compound represented by the formula (2a) include 2-mercaptocyclopentanone, 3-mercaptocyclopentanone, 2-mercaptocyclohexanone, 3-mercaptocyclohexanone, 2-mercaptocycloheptanone, 3-mercaptocyclo Heptanone, 2-mercaptocyclooctanone, 3-mercaptocyclooctanone, 2-mercapto-tetrahydropyran-4-one, 3-mercapto-tetrahydropyran-4-one, 2-mercapto-tetrahydrothiopyran-4-one 3-mercapto-tetrahydrothiopyran-4-one, 4-mercapto-tetrahydrothiophene-3-one, 5-mercapto-3-pyrrolidone, 5-mercapto-N-methyl-3-pyrrolidone, 4-mercapto-tetrahydropyran -3 ON, 5-mercapto-tetrahydropyran-3-one, 3-mercapto-tetrahydropyran-4-one, 4-mercapto-3-piperidone, 5-mercapto-3-piperidone, 3-mercapto-4-piperidone, 4- Examples include mercapto-N-methyl-3-piperidone, 5-mercapto-N-methyl-3-piperidone and 3-mercapto-N-methyl-4-piperidone. Among these, 2-mercaptocyclopentanone and 2-mercaptocyclohexanone are preferable.
これらのメルカプト化合物も、市販のハロゲン化物からAnn.1960,639.146−56に記載された方法に準じて合成できる。
次に、本発明の毛髪矯正剤について説明する。
These mercapto compounds are also commercially available from Ann. 1960, 639.146-56.
Next, the hair straightener of the present invention will be described.
本発明の毛髪矯正剤は、上述した式(1)または式(2)で示されるメルカプト化合物を少なくとも1種含んでいることを特徴とする。上記メルカプト化合物は、単独で使用することも可能であるが、2種類以上組み合わせて使用することができる。 The hair straightener of the present invention contains at least one mercapto compound represented by the above formula (1) or (2). Although the said mercapto compound can also be used independently, it can be used in combination of 2 or more types.
本発明の毛髪矯正剤は、上記メルカプト化合物を通常0.01〜15質量%、より好ましくは0.1〜10質量%、さらに好ましくは1〜5質量%の量で含有する。上記メルカプト化合物の含有量がこの範囲にあれば、期待される毛髪矯正効果を充分に発揮することができる。 The hair straightener of the present invention contains the mercapto compound in an amount of usually 0.01 to 15% by mass, more preferably 0.1 to 10% by mass, and still more preferably 1 to 5% by mass. If the content of the mercapto compound is within this range, the expected hair straightening effect can be sufficiently exhibited.
その一方、メルカプト化合物の含有量が上記下限値未満では本発明の効果がほとんど発揮されない場合があり、上記上限値を超えると臭気が強くなるので実用的でない場合がある。 On the other hand, if the content of the mercapto compound is less than the above lower limit value, the effect of the present invention may be hardly exhibited. If the content exceeds the above upper limit value, the odor becomes strong and may not be practical.
本発明の毛髪矯正剤は、予め調製した毛髪矯正剤として使用してもよく、使用する直前に各薬剤を混合する用事調製の態様で使用してもよい。用事調製の場合には、上記式(1)または式(2)で表されるメルカプト化合物以外を含む薬剤に当該メルカプト化合物を原液あるいは結晶のまま添加する方式でもよく、当該メルカプト化合物を膨潤剤や浸透促進剤などの添加剤などで溶解した希釈液の状態で混合する方式でもよい。 The hair straightening agent of the present invention may be used as a hair straightening agent prepared in advance, or may be used in an aspect of preparation for preparation in which each drug is mixed immediately before use. In the case of business preparation, the mercapto compound may be added as a stock solution or in a crystal form to a drug containing other than the mercapto compound represented by the above formula (1) or formula (2). A method of mixing in the state of a diluted solution dissolved with additives such as a penetration enhancer may be used.
また、水を主成分とする毛髪矯正剤を調製する場合には、式(1)または式(2)で示されるメルカプト化合物の、水に対する溶解性を向上し、溶解時間の短縮、油層の生成を防ぐために、溶解補助剤としてプロピレングリコール、N−メチルピロリドン、エトキシエタノールなどの、通常、化粧品に使用される添加剤を使用し、その配合量を増やすことで溶解速度を速めることができる。なお、このような添加剤の増加により、本来必要とされる性能に低下がみられる場合には、2相分離の状態にて調製して、使用の度に混合する態様で使用してもよい。また、界面活性剤を添加して乳化状態にして使用してもよい。 In addition, when preparing a hair straightener containing water as a main component, the solubility of the mercapto compound represented by formula (1) or formula (2) in water is improved, the dissolution time is shortened, and an oil layer is formed. In order to prevent this, an additive usually used in cosmetics such as propylene glycol, N-methylpyrrolidone and ethoxyethanol is used as a solubilizing agent, and the dissolution rate can be increased by increasing the amount of the additive. In addition, when a decrease in performance that is originally required due to an increase in such additives, it may be prepared in a two-phase separation state and mixed in every use. . Further, a surfactant may be added and used in an emulsified state.
本発明の毛髪矯正剤は、主として、毛髪のくせ毛直し、カール伸ばし、いわゆる寝ぐせの改善のほか、カール形成などにも好適に使用される薬剤であり、パーマネントウエーブ用薬剤の分野で一般に行われる臭素酸塩や過酸化水素による酸化処理を必要としない。 The hair straightener of the present invention is mainly used in the field of permanent wave pharmaceuticals, mainly used for curling hair, straightening curls, improving so-called sleepiness, and curling. No oxidation treatment with bromate or hydrogen peroxide is required.
本発明の毛髪矯正剤は、用途には特に制限はなく、例えば、シャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、ヘアワックス、ヘアムース、頭髪用ジェルなどとして用いられる。 The hair straightener of the present invention is not particularly limited in use, and is used, for example, as a shampoo, rinse, conditioner, hair treatment, hair water, hair wax, hair mousse, hair gel and the like.
これらの中では、シャンプー、リンス、コンディショナー、ヘアトリートメント、ヘアウオーター、またはヘアムースからなる群より選ばれるいずれかの毛髪化粧料として好ましく用いられる。 Among these, it is preferably used as any hair cosmetic selected from the group consisting of shampoos, rinses, conditioners, hair treatments, hair waters, or hair mousses.
また、剤の形態としては、例えば、液状、泡状、ゲル状、クリーム状、ペースト状にして使用可能であり、その形態によって液タイプ、スプレータイプ、エアゾールタイプ、クリームタイプ、ゲルタイプのいずれかのタイプの薬剤として使用できる。 In addition, as the form of the agent, for example, it can be used in the form of liquid, foam, gel, cream or paste, depending on the form, either liquid type, spray type, aerosol type, cream type, gel type Can be used as a type of drug.
本発明の毛髪矯正剤は、毛髪への塗布後、櫛による整髪あるいは洗髪までの比較的短い時間で、くせ毛やカールの矯正ができる。
該毛髪矯正剤は、アルカリ性側で使用できることは言うまでもないが、亜硫酸塩を含む公知の毛髪処理剤で使用されているpHよりも低い、弱酸性から中性領域で使用可能であり、むしろ該pH領域でより一層優れた毛髪変形矯正効果を示す。使用するpHについては特に制限はないが、好ましくはpH2.5〜9.0、更に好ましくはpH3.5〜8.0、特に好ましくはpH4.0〜7.5である。pHが上記範囲にあると皮膚刺激性も少なく、毛髪の損傷などを引き起こす原因となりにくい。なお、pHの測定温度は23℃である。
The hair straightener of the present invention can correct hairs and curls in a relatively short time from hair application to hair styling or hair washing after application to the hair.
It goes without saying that the hair straightener can be used on the alkaline side, but it can be used in the weakly acidic to neutral range, which is lower than the pH used in known hair treatments including sulfites, rather the pH The hair deformation correction effect is even better in the region. Although there is no restriction | limiting in particular about pH to be used, Preferably it is pH 2.5-9.0, More preferably, it is pH 3.5-8.0, Most preferably, it is pH 4.0-7.5. When the pH is in the above range, there is little skin irritation and it is difficult to cause damage to hair. In addition, the measurement temperature of pH is 23 degreeC.
さらに、本発明の毛髪矯正剤によれば、毛髪のソフト感が向上する。その理由は、定かではないが、上記式(1)または式(2)で示されるメルカプト化合物を使用することによって、剤の親油性が増し、毛髪への浸透性が向上するために短時間で効果が現れると推定され、さらには、弱酸性から中性領域で使用されるために毛髪の損傷などがなくソフト感が得られるものと考えられる。 Furthermore, according to the hair straightener of the present invention, the soft feeling of hair is improved. The reason for this is not clear, but by using the mercapto compound represented by the above formula (1) or formula (2), the lipophilicity of the agent is increased and the penetration into the hair is improved in a short time. It is presumed that an effect appears, and further, since it is used in a weakly acidic to neutral region, it is considered that there is no hair damage and a soft feeling can be obtained.
また、本発明の毛髪矯正剤によれば、亜硫酸塩や亜硫酸水素塩などを含まなくとも充分に毛髪の矯正効果が得られるが、本発明の効果を損なわない範囲で、従来から知られている亜硫酸塩や亜硫酸水素塩、あるいは、チオグリコール酸、システインなどを本発明の毛髪矯正剤にさらに使用することも可能である。 Further, according to the hair straightener of the present invention, a hair straightening effect can be sufficiently obtained without containing sulfite or hydrogen sulfite, but it is conventionally known as long as the effect of the present invention is not impaired. It is also possible to further use sulfite, bisulfite, thioglycolic acid, cysteine and the like in the hair straightener of the present invention.
さらに、本発明の毛髪矯正剤には、毛髪の加工性能および使用感を向上させる目的で公知慣用の添加剤を配合してもよい。添加剤としては、界面活性剤、起泡洗浄助剤、過脂肪剤、増粘剤、粘度調整剤、不透明化剤、キレート剤、紫外線吸収剤、防腐剤、抗フケ剤、殺菌防腐剤、毛髪保護剤、湿潤剤、乳化剤、浸透促進剤、緩衝剤、香料、染料、安定化剤、臭気マスキング剤、パール剤等が挙げられる。また、必要に応じて、美容成分、その他、化粧料において汎用の他の成分を配合してもよい。 Furthermore, you may mix | blend a well-known and usual additive with the hair straightener of this invention in order to improve the processing performance and usability of hair. Additives include surfactants, foaming aids, overfat agents, thickeners, viscosity modifiers, opacifiers, chelating agents, UV absorbers, antiseptics, anti-dandruff agents, disinfecting antiseptics, hair Protective agents, wetting agents, emulsifiers, penetration enhancers, buffers, fragrances, dyes, stabilizers, odor masking agents, pearl agents, and the like. Moreover, you may mix | blend the other general component in cosmetics and other cosmetics as needed.
界面活性剤としては、アニオン性界面活性剤として、ラウリル硫酸ナトリウム、ポリオキシエチレンラウリルエーテル硫酸ナトリウム、ヤシ油脂肪酸メチルタウリンナトリウム、ラウロイルメチルアラニンナトリウム;両性界面活性剤としては、ラウリルジメチルアミノ酢酸ベタイン、イミダゾリン系活性剤、ヤシ油脂肪酸アミドプロピルベタイン;カチオン界面活性剤としては、塩化セチルトリメチルアンモニウム、塩化ステアリルトリメチルアンモニウム、塩化ベヘニルトリメチルアンモニウム;非イオン性界面活性剤としては、アルキルアルカノールアミドなどが挙げられる。 As surfactants, anionic surfactants include sodium lauryl sulfate, polyoxyethylene lauryl ether sodium sulfate, coconut oil fatty acid sodium methyl taurine, sodium lauroyl methylalanine; amphoteric surfactants include lauryl dimethylaminoacetic acid betaine, Imidazoline-based surfactants, coconut oil fatty acid amidopropyl betaine; cationic surfactants include cetyltrimethylammonium chloride, stearyltrimethylammonium chloride, behenyltrimethylammonium chloride; nonionic surfactants include alkylalkanolamides .
増粘剤としては、カルボキシメチルセルロース、カルボキシビニルポリマー、ヒドロキシエチルセルロース、ヒドロキシプロピルセルロース、キサンタンガム、カラギーナン、アルギン酸塩、ペクチン、トラガントガム、ポリビニルピロリドンなどの高分子化合物;ラウリルアルコール、セチルアルコール、ステアリルアルコール、イソステアリルアルコール、オレイルアルコール、ベヘニルアルコールなどの高級アルコール;カオリン;ラウ
リン酸、ミリスチン酸、パルミチン酸、ステアリン酸、ベヘニン酸、オレイン酸、ウンデシル酸、イソステアリン酸などの脂肪酸;ワセリンなどが挙げられる。
Thickeners include polymer compounds such as carboxymethylcellulose, carboxyvinyl polymer, hydroxyethylcellulose, hydroxypropylcellulose, xanthan gum, carrageenan, alginate, pectin, tragacanth gum, polyvinylpyrrolidone; lauryl alcohol, cetyl alcohol, stearyl alcohol, isostearyl Higher alcohols such as alcohol, oleyl alcohol, and behenyl alcohol; kaolin; fatty acids such as lauric acid, myristic acid, palmitic acid, stearic acid, behenic acid, oleic acid, undecylic acid, and isostearic acid; petrolatum and the like.
湿潤剤あるいは乳化剤としては、グリセリン、ジグリセリン、プロピレングリコール、ジプロピレングリコール、1,3−ブタンジオール、ポリエチレングリコール、ソルビトール、植物抽出エキス、ビタミン類、ヒアルロン酸塩、コンドロイチン硫酸塩、上述したカチオン性界面活性剤、アニオン性界面活性剤、両性界面活性剤、非イオン性界面活性剤や、ポリオキシエチレンオレイルエーテル、ポリオキシエチレンステアリルエーテル、ポリオキシエチレンセチルエーテル、ポリオキシエチレンオクチルフェニルエーテル、ポリオキシエチレンドデシルフェニルエーテル、ポリオキシエチレンノニルエーテルなどのエーテル型非イオン界面活性剤;ジメチルポリシロキサン、メチルフェニルポリシロキサン、アミノ変性シリコーンオイル、アルコール変性シリコーンオイル、フッ素変性シリコーンオイル、ポリエーテル変性シリコーンオイル、アルキル変性シリコーンオイルなどのシリコーン誘導体などが挙げられる。 Wetting agents or emulsifiers include glycerin, diglycerin, propylene glycol, dipropylene glycol, 1,3-butanediol, polyethylene glycol, sorbitol, plant extract, vitamins, hyaluronate, chondroitin sulfate, and the above-mentioned cationic Surfactant, anionic surfactant, amphoteric surfactant, nonionic surfactant, polyoxyethylene oleyl ether, polyoxyethylene stearyl ether, polyoxyethylene cetyl ether, polyoxyethylene octylphenyl ether, polyoxy Ether type nonionic surfactants such as ethylene dodecyl phenyl ether and polyoxyethylene nonyl ether; dimethyl polysiloxane, methyl phenyl polysiloxane, amino-modified silicone oil Alcohol-modified silicone oil, fluorine-modified silicone oil, polyether-modified silicone oil, and silicone derivatives, such as alkyl-modified silicone oil.
浸透促進剤としては、エタノール、プロパノール、イソプロパノール、1,2−プロピレングリコール、1,3−ブタンジオール、グリセリン、エチルカルビトール、ベンジルアルコール、ベンジルオキシエタノール、尿素、2−メチルピロリドンなどが挙げられる。 Examples of penetration enhancers include ethanol, propanol, isopropanol, 1,2-propylene glycol, 1,3-butanediol, glycerin, ethyl carbitol, benzyl alcohol, benzyloxyethanol, urea, and 2-methylpyrrolidone.
緩衝剤としては、無機緩衝剤のほか、アルギニン、リジンなどの塩基性アミノ酸を含む緩衝剤、クエン酸塩などの有機酸類が挙げられる。
pH調整剤としては、塩酸、リン酸などの無機酸、あるいはリン酸水素二ナトリウム、リン酸二水素ナトリウム等の無機酸塩;クエン酸、リンゴ酸、乳酸、コハク酸、シュウ酸などの有機酸、あるいはそのナトリウム塩;アンモニア、ジエタノールアミン、トリエタノールアミン、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウムなどのアルカリ剤が挙げられる。
Examples of the buffer include inorganic buffers, buffers containing basic amino acids such as arginine and lysine, and organic acids such as citrate.
Examples of pH adjusters include inorganic acids such as hydrochloric acid and phosphoric acid, or inorganic acid salts such as disodium hydrogen phosphate and sodium dihydrogen phosphate; organic acids such as citric acid, malic acid, lactic acid, succinic acid, and oxalic acid. Or an alkali agent such as ammonia, diethanolamine, triethanolamine, sodium hydroxide, potassium hydroxide, sodium carbonate, sodium bicarbonate, potassium carbonate, potassium bicarbonate, or the like.
香料としては、(A)炭化水素類、(B)アルコール類、(C)フェノール類、(D)アルデヒド類及び/又はアセタール類、(E)ケトン類及び/又はケタール類、(F)エーテル類、(G)合成ムスク類、(H)酸類、(I)ラクトン類、(J)エステル類、(K)含窒素及び/又は含硫及び/又は含ハロゲン化合物、(L)天然香料等を使用することができる。具体的には、特開2003−137758号公報に開示されたものが例示される。 As perfumes, (A) hydrocarbons, (B) alcohols, (C) phenols, (D) aldehydes and / or acetals, (E) ketones and / or ketals, (F) ethers , (G) synthetic musks, (H) acids, (I) lactones, (J) esters, (K) nitrogen-containing and / or sulfur-containing and / or halogen-containing compounds, (L) natural fragrances, etc. can do. Specifically, what was disclosed by Unexamined-Japanese-Patent No. 2003-137758 is illustrated.
(A)炭化水素類は、炭素と水素で構成された揮発性有機化合物であれば特に限定されることはなく、脂肪族炭化水素類、脂環式炭化水素類、テルペン系炭化水素類、芳香族炭化水素類などが例示される。
(B)アルコール類は、水酸基を持つ揮発性有機化合物であれば特に限定されることはなく、脂肪族アルコール類、脂環式アルコール類、テルペン系アルコール類、芳香族アルコール類などが例示される。
(C)フェノール類は、フェノール性の化合物及びその誘導体であって香りを有する有機化合物であれば特に限定されることはなく、例えば1価、2価、3価のフェノール性化合物、ポリフェノール類、又はこれらの化合物のエーテル誘導体などが例示される。
(D)アルデヒド類又はアセタール類は、アルデヒド基又はアセタール基を分子内にもつ揮発性有機化合物であれば特に限定されることはなく、脂肪族アルデヒドやアセタール、テルペン系アルデヒドやアセタール、芳香族アルデヒドやアセタールなどが例示される。
(E)ケトン類又はケタール類は、ケトン基又はケタール基を分子内にもつ揮発性有機化合物であれば特に限定されることはなく、脂肪族ケトンやケタール、テルペン系ケトン
やケタール、芳香族ケトンやケタールなどが例示される。
(F)エーテル類は、分子内にエーテル基を有する揮発性有機化合物であれば特に限定されることはなく、脂肪族エーテル、テルペン系エーテル、芳香族エーテルなどが例示される。
(G)合成ムスク類は、ムスク香或いはムスク類似香を有する有機化合物であれば特に限定されることはない。
(H)酸類は、分子内にカルボキシル基を有する有機化合物であれば特に限定されることはない。
(I)ラクトン類は、分子内にラクトン基を有する揮発性有機化合物であれば特に限定されることはない。
(J)エステル類は、分子内にエステル基を有する揮発性有機化合物であれば特に限定されることはない。
(K)含窒素及び/又は含硫黄及び/又は含ハロゲン化合物は、窒素、硫黄、ハロゲンを分子中に含有する有香性有機化合物であれば特に限定されることはない。
(L)天然香料も特に限定はない。
(A) The hydrocarbon is not particularly limited as long as it is a volatile organic compound composed of carbon and hydrogen, and is not limited to aliphatic hydrocarbons, alicyclic hydrocarbons, terpene hydrocarbons, aromatics. Group hydrocarbons and the like are exemplified.
(B) The alcohol is not particularly limited as long as it is a volatile organic compound having a hydroxyl group, and examples thereof include aliphatic alcohols, alicyclic alcohols, terpene alcohols, and aromatic alcohols. .
(C) The phenols are not particularly limited as long as they are phenolic compounds and derivatives thereof, and are organic compounds having a fragrance. For example, monovalent, divalent, and trivalent phenolic compounds, polyphenols, Or the ether derivative of these compounds etc. are illustrated.
(D) Aldehydes or acetals are not particularly limited as long as they are volatile organic compounds having an aldehyde group or an acetal group in the molecule. Aliphatic aldehydes, acetals, terpene aldehydes, acetals, aromatic aldehydes And acetal.
(E) Ketones or ketals are not particularly limited as long as they are volatile organic compounds having a ketone group or ketal group in the molecule. Aliphatic ketones, ketals, terpene ketones, ketals, aromatic ketones And ketal.
The (F) ether is not particularly limited as long as it is a volatile organic compound having an ether group in the molecule, and examples thereof include aliphatic ethers, terpene ethers, and aromatic ethers.
(G) The synthetic musk is not particularly limited as long as it is an organic compound having a musk aroma or a musk-like aroma.
(H) Acids are not particularly limited as long as they are organic compounds having a carboxyl group in the molecule.
(I) The lactone is not particularly limited as long as it is a volatile organic compound having a lactone group in the molecule.
(J) The esters are not particularly limited as long as they are volatile organic compounds having an ester group in the molecule.
(K) The nitrogen-containing and / or sulfur-containing and / or halogen-containing compound is not particularly limited as long as it is a fragrant organic compound containing nitrogen, sulfur and halogen in the molecule.
(L) The natural fragrance is not particularly limited.
これら香料の具体例を以下に例示する。たとえば、
2,6,10−トリメチル−9−ウンデカナール、n−デセナール、n−オクタナール、アミルグリコール酸アリル、ヘキサン酸アリル、α-アミルシンナミルアルデヒド、アネ
ソール、p−メトキシベンズアルデヒド、6,7−デヒドロ−1,1,2,3,3−ペンタメチル−4(5H)−インダノン、シンナミルアルコール、cis−3−ヘキセン−1−
イル酢酸エステル、cis−6−ノネノール、シトラール、シトラールジエチルアセタール
、シトロネラール、シトロネロール、シトロネリルニトリル、酢酸トリシクロデセン、プロピオン酸トリシクロデセン、酢酸シクロヘキシルオキシ−2−プロペニルエステル、δ−ダマスコン、ジヒロドジャスモン、ジフェニルエーテル、アセトアルデヒドエチルフェニルアセタール、アセトアルデヒドエチルリナリルアセタール、エストラゴール、エチル2−メチルブチレート、エチルマルトール、エチルブチレート、エチルデヒドロシクロゲラネート、エチルバニリン、オイゲノール、p−エチル−α,α−ジメチルジヒドロシンナムアルデヒド、2,4,6−トリメチル−4−フェニル−1,3−ジオキサン、エチルオクタヒドロ−4,7−メタノ[3aH]-3a-カルボキシレート、2−エチル−4−ヒドロキ
シ−5−メチル−3−(2H)フラノン、α−メチルフェニルアセトアルデヒド、インドール、
Specific examples of these fragrances are illustrated below. For example,
2,6,10-trimethyl-9-undecanal, n-decenal, n-octanal, allyl amyl glycolate, allyl hexanoate, α-amylcinnamyl aldehyde, anesole, p-methoxybenzaldehyde, 6,7-dehydro- 1,1,2,3,3-pentamethyl-4 (5H) -indanone, cinnamyl alcohol, cis-3-hexene-1-
Ile acetate ester, cis-6-nonenol, citral, citral diethyl acetal, citronellal, citronellol, citronellilnitrile, tricyclodecene acetate, tricyclodecene propionate, cyclohexyloxy-2-propenyl acetate, δ-damascone, dihiro Dojasmon, diphenyl ether, acetaldehyde ethyl phenyl acetal, acetaldehyde ethyl linalyl acetal, estragole, ethyl 2-methyl butyrate, ethyl maltol, ethyl butyrate, ethyl dehydrocyclogeranate, ethyl vanillin, eugenol, p-ethyl-α, α -Dimethyldihydrocinnamaldehyde, 2,4,6-trimethyl-4-phenyl-1,3-dioxane, ethyloctahydro-4,7-methano [3aH ] -3a-carboxylate, 2-ethyl-4-hydroxy-5-methyl-3- (2H) furanone, α-methylphenylacetaldehyde, indole,
α−イオノン、サリチル酸イソアミル、イソブチルキノリン、α−イソメチルイオノン、フェニルアセトアルデヒド、6−(3−フェニル)テトラヒドロ[2H]ピラン−2−オン、2−(2,4−ジメチル−3−シクロヘキシル)−5−メチル−5−(1−メチルプロピル)−1,3−ジオキサン、cis−3−ヘキセノール、ゲラニルニトリル、cis−3−ヘキセニルメチルカルボネート、テトラヒドロリナノール、リナロール、cis−3−ドデセナ
ール、エチル 2−メチルペンタン酸エステル、2,6−ジメチル−5−ヘプタナール、メチル アントラニル酸エステル、安息香酸メチル、サリチル酸メチル、3−メチルシクロペンタデカノリド、ネロール、p−クレゾール、p−メチルアニソール、フェニル酢酸、β−フェネチルアルコール、フェネチルホルメート、フェネチルイソアミルエーテル、4−(p−ヒドロキシフェニル)−2−ブタノン、テトラヒドロ−4−メチル−2−(2−メチル−1−プロペニル)−(2H)ピラン、5−メチル−3−ヘプタノンオキシム、trans−2−ヘキセン−1−オール、2−トリデセノニトリル、3−シクロヘキセン−1
−カルボキサアルデヒドジメチルアセタール、バニリン、o−tert−ブチルシクロヘキシ
ル酢酸エステル、アセチルセドレン、ベチベリル酢酸エステル、フェニルアセトアルデヒドジメチルアセタール、ロジノールなどである。
α-ionone, isoamyl salicylate, isobutylquinoline, α-isomethylionone, phenylacetaldehyde, 6- (3-phenyl) tetrahydro [2H] pyran-2-one, 2- (2,4-dimethyl-3-cyclohexyl) -5-methyl-5- (1-methylpropyl) -1,3-dioxane, cis-3-hexenol, geranyl nitrile, cis-3-hexenylmethyl carbonate, tetrahydrolinanol, linalool, cis-3-dodecenal, Ethyl 2-methylpentanoate, 2,6-dimethyl-5-heptanal, methyl anthranilate, methyl benzoate, methyl salicylate, 3-methylcyclopentadecanolide, nerol, p-cresol, p-methylanisole, Phenylacetic acid, β-phenethyl alcohol, phenethyl Formate, phenethyl isoamyl ether, 4- (p-hydroxyphenyl) -2-butanone, tetrahydro-4-methyl-2- (2-methyl-1-propenyl)-(2H) pyran, 5-methyl-3-heptanone Oxime, trans-2-hexen-1-ol, 2-tridecenonitrile, 3-cyclohexene-1
-Carboxaaldehyde dimethyl acetal, vanillin, o-tert-butylcyclohexyl acetate, acetyl cedrene, vetiberyl acetate, phenylacetaldehyde dimethyl acetal, rosinol.
その他の添加剤としては、パラフィン、流動パラフィン、ミツロウ、スクワラン、ホホ
バ油、オリーブ油、エステル油、トリグリセリド、ワセリン、ラノリンなどの油剤;コラーゲンやケラチンなどの加水分解物およびその誘導体などの毛髪保護成分が挙げられる。
Other additives include oils such as paraffin, liquid paraffin, beeswax, squalane, jojoba oil, olive oil, ester oil, triglyceride, petrolatum, lanolin; hair protecting ingredients such as hydrolysates such as collagen and keratin and their derivatives. Can be mentioned.
以下に、実施例を挙げて本発明を説明するが、本発明はこれらの実施例により何ら限定されるものではない。なお、以下の例中において、とくに言及しない限り、「%」および「部」は質量基準である。 EXAMPLES The present invention will be described below with reference to examples, but the present invention is not limited to these examples. In the following examples, “%” and “part” are based on mass unless otherwise specified.
[合成例1]
チオグリコール酸2−メトキシエチルエステルの合成
温度計、冷却管付きの1000mLの4つ口フラスコにチオグリコール酸メチル300g(2.83mol、東京化成株式会社製)と2−メトキシエタノール320g(4.21mol、東京化成株式会社製)、95%硫酸3.6g(純正化学株式会社製)を入れ、80℃にて5時間撹拌した。反応中は、冷却管上部からアスピレーターを使用して微減圧とすることで反応の進行によって生成するメタノールを留去した。反応後の液を直接濃縮、減圧下で蒸留精製し、沸点:65℃/0.6kPaにてチオグリコール酸2−メトキシエチルエステルを123g(0.82mol、収率29%)取得した。
[Synthesis Example 1]
Synthesis of 2-methoxyethyl ester of thioglycolic acid 300 g (2.83 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) and 320 g (4.21 mol) of 2-methoxyethanol in a 1000 mL four-necked flask equipped with a thermometer and a cooling tube , Manufactured by Tokyo Chemical Industry Co., Ltd.) and 3.6 g of 95% sulfuric acid (manufactured by Junsei Chemical Co., Ltd.), and stirred at 80 ° C. for 5 hours. During the reaction, methanol generated by the progress of the reaction was distilled off by using an aspirator from the upper part of the cooling pipe to make a slight vacuum. The solution after the reaction was directly concentrated and purified by distillation under reduced pressure to obtain 123 g (0.82 mol, yield 29%) of thioglycolic acid 2-methoxyethyl ester at a boiling point of 65 ° C./0.6 kPa.
[合成例2]
チオグリコール酸2−エトキシエチルエステルの合成
チオグリコール酸メチル300g(2.83mol、東京化成株式会社製)と2−エトキシエタノール379g(4.21mol、東京化成株式会社製)を使用した以外は、合成例1と同様にして、沸点:99〜103℃/2.0kPaにてチオグリコール酸2−エトキシエチルエステル144g(0.88mol、収率31%)を取得した。
[Synthesis Example 2]
Synthesis of thioglycolic acid 2-ethoxyethyl ester Synthesis except that 300 g of methyl thioglycolate (2.83 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) and 379 g of 2-ethoxyethanol (4.21 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) were used In the same manner as in Example 1, 144 g (0.88 mol, 31% yield) of thioglycolic acid 2-ethoxyethyl ester was obtained at a boiling point of 99 to 103 ° C./2.0 kPa.
[合成例3]
チオ乳酸2−エトキシエチルエステルの合成
チオ乳酸300g(2.83mol)と2−エトキシエタノール379g(4.21mol、東京化成株式会社製)を使用した以外は、合成例1と同様にして、沸点:102℃/2.6kPaにてチオ乳酸2−エトキシエチルエステル175g(0.98mol、収率35%)を取得した。
[Synthesis Example 3]
Synthesis of thiolactic acid 2-ethoxyethyl ester In the same manner as in Synthesis Example 1 except that 300 g (2.83 mol) of thiolactic acid and 379 g of 2-ethoxyethanol (4.21 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) were used, the boiling point: 175 g (0.98 mol, yield 35%) of thiolactic acid 2-ethoxyethyl ester was obtained at 102 ° C./2.6 kPa.
[合成例4]
メルカプトプロピオン酸2−エトキシエチルエステルの合成
メルカプトプロピオン酸300g(2.83mol)と2−エトキシエタノール379g(4.21mol、東京化成株式会社製)を使用した以外は、合成例1と同様にして、沸点:101℃/2.0kPaにてメルカプトプロピオン酸2−エトキシエチルエステル166g(0.93mol、収率33%)を取得した。
[Synthesis Example 4]
Synthesis of mercaptopropionic acid 2-ethoxyethyl ester In the same manner as in Synthesis Example 1, except that 300 g (2.83 mol) mercaptopropionic acid and 379 g (4.21 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) were used. Boiling point: 166 g (0.93 mol, yield 33%) of mercaptopropionic acid 2-ethoxyethyl ester was obtained at 101 ° C./2.0 kPa.
[合成例5]
2−メルカプト−4−ブタノリド(別名:2−メルカプト−4−ブチロラクトン)の合成
70%水硫化ナトリウム(49g、0.6mmol、純正化学株式会社製)をメチルアルコール(500g、純正化学社製、特級)と精製水(蒸留後にイオン交換フィルターを通した水、500g)に溶解した。溶解した液を撹拌しながら氷冷し10℃以下まで冷却した。冷却した溶液に2−ブロモ−4−ブタノリド(100g、0.6mol、東京化成株式会社製)を約30分かけて滴下した。滴下完了後の液を10分間撹拌した後に、反応液を減圧下で約半量となるまで濃縮した。濃縮した液に、酢酸エチル(500mL、純正化学社製、特級)を加えて抽出した。得られた水相を酢酸エチル(500mL)で再抽出した。これらの抽出した有機相を合わせて、減圧下に濃縮、蒸留精製し、沸点:94℃/0.3kPaにて2−メルカプト−4−ブタノリド(23g、収率32%)を得た。
[Synthesis Example 5]
Synthesis of 2-mercapto-4-butanolide (also known as 2-mercapto-4-butyrolactone) 70% sodium hydrosulfide (49 g, 0.6 mmol, manufactured by Junsei Co., Ltd.) and methyl alcohol (500 g, Junsei Chemical Co., Ltd., special grade) ) And purified water (water through an ion exchange filter after distillation, 500 g). The dissolved liquid was ice-cooled with stirring and cooled to 10 ° C. or lower. To the cooled solution, 2-bromo-4-butanolide (100 g, 0.6 mol, manufactured by Tokyo Chemical Industry Co., Ltd.) was added dropwise over about 30 minutes. After the completion of the dropwise addition, the liquid was stirred for 10 minutes, and then the reaction liquid was concentrated to about half volume under reduced pressure. To the concentrated liquid, ethyl acetate (500 mL, manufactured by Junsei Chemical Co., Ltd., special grade) was added for extraction. The resulting aqueous phase was re-extracted with ethyl acetate (500 mL). These extracted organic phases were combined, concentrated under reduced pressure, and purified by distillation to obtain 2-mercapto-4-butanolide (23 g, yield 32%) at a boiling point of 94 ° C./0.3 kPa.
[合成例6]
2−メルカプトシクロペンタノンの合成
ナトリウムメトキシドのメタノール溶液(44g;ナトリウムメトキシドとして濃度28%、0.22mol、純正化学株式会社製)に氷冷下、約10℃以下を保ちながら硫化水素ガス(住友精化株式会社製ボンベ充填硫化水素ガス)を10g吹き込んだ。10℃以下を保つ様にして、2−ブロモシクロペンタノン23.7g(0.2mol、東京化成株式会社製)を滴下した。滴下後の液を30分間、5℃以下を保ちながら撹拌した。反応後の液を真空ポンプで徐々に減圧して、約35gとなるまでメタノールを留去した。留去後の液に10℃以下を保ちながら、10%塩酸をpH3となるまで滴下した。滴下後の液にジエチルエーテル100gを加えて抽出し、得られた水相をジエチルエーテル100gで2回再抽出した。抽出したジエチルエーテル相を混ぜて、エバポレーターを使用して濃縮した。濃縮後の油状成分を減圧下に蒸留精製し、沸点:51℃/0.9kPaにて2−メルカプトシクロペンタノン7.4g(0.064mol、収率32%)を得た。
[Synthesis Example 6]
Synthesis of 2-mercaptocyclopentanone Hydrogen sulfide gas in a methanol solution of sodium methoxide (44 g; concentration 28% as sodium methoxide, 0.22 mol, manufactured by Junsei Chemical Co., Ltd.) under ice-cooling while maintaining about 10 ° C. or less 10 g (bomb filled hydrogen sulfide gas manufactured by Sumitomo Seika Co., Ltd.) was blown. 2-Bromocyclopentanone 23.7g (0.2mol, Tokyo Chemical Industry Co., Ltd.) was dripped so that 10 degrees C or less might be maintained. The liquid after the dropping was stirred for 30 minutes while maintaining the temperature at 5 ° C or lower. The liquid after the reaction was gradually depressurized with a vacuum pump, and methanol was distilled off to about 35 g. While maintaining the temperature at 10 ° C. or lower, 10% hydrochloric acid was added dropwise until the pH reached 3. The liquid after the addition was extracted by adding 100 g of diethyl ether, and the resulting aqueous phase was re-extracted twice with 100 g of diethyl ether. The extracted diethyl ether phases were mixed and concentrated using an evaporator. The oily component after concentration was purified by distillation under reduced pressure to obtain 7.4 g (0.064 mol, yield 32%) of 2-mercaptocyclopentanone at a boiling point of 51 ° C./0.9 kPa.
[合成例7]
2、4−ジブロモ酪酸ブロミドの合成
A.Kamalらの方法(Tetrahedron:Asymmetry 2003, 14, 2587)に準じて、4−ブタノリ
ドより合成した。
4−ブタノリド(20g、0.23mol、東京化成株式会社)に三臭化リン(2.5g、0.43g atom、東京化成株式会社)を加えた。
上記の溶液に、10℃以下を保ちながら臭素(40.4g、0.25mol、和光純薬株式会社)を撹拌下、約2hrかけて滴下した。滴下完了後、70℃に昇温して、臭素(40.4g、0.25mol、和光純薬株式会社)を約30分間かけて滴下した。滴下完了後の液を80℃に昇温した後に、80℃で3時間撹拌した。
反応終了後の反応液の下部にガラス管を挿入し、ガラス管より窒素を吹き込む事で、未反応の臭素と反応により生成する臭化水素を除去した。この反応液を減圧下に蒸留することで、2,4−ジブロモ酪酸ブロミド(38g、0.12mol、bp.87−88℃/0.7kPa、収率53%)を得た。
[Synthesis Example 7]
Synthesis of 2,4-dibromobutyric acid bromide
The compound was synthesized from 4-butanolide according to the method of A. Kamal et al. (Tetrahedron: Asymmetry 2003, 14, 2587).
Phosphorus tribromide (2.5 g, 0.43 g atom, Tokyo Chemical Industry Co., Ltd.) was added to 4-butanolide (20 g, 0.23 mol, Tokyo Chemical Industry Co., Ltd.).
Bromine (40.4 g, 0.25 mol, Wako Pure Chemical Industries, Ltd.) was added dropwise to the above solution over about 2 hours while stirring at 10 ° C. or lower. After completion of dropping, the temperature was raised to 70 ° C., and bromine (40.4 g, 0.25 mol, Wako Pure Chemical Industries, Ltd.) was added dropwise over about 30 minutes. The solution after completion of the dropwise addition was heated to 80 ° C. and then stirred at 80 ° C. for 3 hours.
After completion of the reaction, a glass tube was inserted into the lower part of the reaction solution, and nitrogen was blown from the glass tube to remove unreacted bromine and hydrogen bromide produced by the reaction. This reaction solution was distilled under reduced pressure to obtain 2,4-dibromobutyric acid bromide (38 g, 0.12 mol, bp. 87-88 ° C./0.7 kPa, yield 53%).
[合成例8]
N−メチル−2−ブロモ−4−ブチロラクタムの合成
40%メチルアミン水溶液(7.9g、0.10mol、純正化学株式会社)と水3.3gの混合溶液を10℃以下に冷却した溶液に、10℃以下を保つようにして2,4−ジブロモ酪酸ブロミド(38g、0.12mol)を15分間で滴下した。滴下完了後に30℃に昇温して、30分間撹拌した。反応液にクロロホルム50gを加えて、有機層を抽出した。分離した有機層に硫酸マグネシウムを加えて乾燥した。硫酸マグネシウムをろ過により除去して得られた有機層を濃縮して得られる濃縮残渣をシリカゲルカラムクロマトグラフィーで精製することでN−メチル−2,4−ジブロモ酪酸アミド(23.1g、0.090mol、収率74%)を得た。
得られたN−メチル−2,4−ジブロモ酪酸アミドをTHF(200mL)に溶解した。溶解した溶液を氷冷下10℃以下としてから60%NaH in mineral oil(6.6g、0.166mol、純正化学株式会社)を約15分で少しずつ加えた。添加後に室温まで昇温して、2時間撹拌した。反応後の反応液を約1/3重量となるまで濃縮した後に、濃縮残渣を氷水(100g)に入れた。クロロホルム100gで抽出した。得られたクロロホルム層を濃縮して得られる濃縮残渣をシリカゲルカラムクロマトグラフィーで精製することでN−メチル−2−ブロモ−4−ブチロラクタム(10.2g、0.057mol、収率69%)を取得した。
[Synthesis Example 8]
Synthesis of N-methyl-2-bromo-4-butyrolactam A mixed solution of 40% methylamine aqueous solution (7.9 g, 0.10 mol, Junsei Chemical Co., Ltd.) and water 3.3 g was cooled to 10 ° C. or lower. 2,4-Dibromobutyric acid bromide (38 g, 0.12 mol) was added dropwise over 15 minutes while maintaining the temperature at 10 ° C. or lower. After completion of dropping, the temperature was raised to 30 ° C. and stirred for 30 minutes. Chloroform 50g was added to the reaction liquid, and the organic layer was extracted. Magnesium sulfate was added to the separated organic layer and dried. N-methyl-2,4-dibromobutyric acid amide (23.1 g, 0.090 mol) was obtained by purifying the concentrated residue obtained by concentrating the organic layer obtained by removing magnesium sulfate by filtration, using silica gel column chromatography. Yield 74%).
The obtained N-methyl-2,4-dibromobutyric acid amide was dissolved in THF (200 mL). The dissolved solution was cooled to 10 ° C. or lower under ice cooling, and then 60% NaH in mineral oil (6.6 g, 0.166 mol, Junsei Chemical Co., Ltd.) was added little by little in about 15 minutes. After the addition, the mixture was warmed to room temperature and stirred for 2 hours. After the reaction solution after the reaction was concentrated to about 1/3 weight, the concentrated residue was put into ice water (100 g). Extracted with 100 g of chloroform. The concentrated residue obtained by concentrating the obtained chloroform layer was purified by silica gel column chromatography to obtain N-methyl-2-bromo-4-butyrolactam (10.2 g, 0.057 mol, yield 69%). did.
[合成例9]
N−メチル−2−メルカプト−4−ブチロラクタムの合成
70%水硫化ナトリウム(6.1g、0.077mmol、純正化学株式会社製)をメチルアルコール(100g、純正化学社製、特級)と精製水(蒸留後にイオン交換フィルターを通した水、100g)に溶解した。溶解した液を撹拌しながら氷冷し10℃以下まで冷却した。冷却した溶液にN−メチル−2−ブロモ−4−ブチロラクタム(11.4g、0.064mol、収率77%)のメチルアルコール(50g)の混合液を約30分かけて滴下した。滴下完了後の液を60分間撹拌した後に、反応液を減圧下で約1/3量となるまで濃縮した。濃縮した液に、酢酸エチル(500mL、純正化学社製、特級)を加えて抽出した。残った水相はさらに酢酸エチル(500mL)で再抽出した。これらの抽出した有機相(酢酸エチル相)を合わせて、減圧下で濃縮した。濃縮して得られた残渣をシリカゲルカラムクロマトグラフィーで精製することでN−メチル−2−メルカプト−4−ブチロラクタム(5.4g、0.041mol、収率64%)を取得した。
[Synthesis Example 9]
Synthesis of N-methyl-2-mercapto-4-butyrolactam 70% sodium hydrosulfide (6.1 g, 0.077 mmol, manufactured by Junsei Chemical Co., Ltd.), methyl alcohol (100 g, Junsei Chemical Co., Ltd., special grade) and purified water ( After distillation, it was dissolved in 100 g) of water passed through an ion exchange filter. The dissolved liquid was ice-cooled with stirring and cooled to 10 ° C. or lower. To the cooled solution was added dropwise a mixture of methyl alcohol (50 g) of N-methyl-2-bromo-4-butyrolactam (11.4 g, 0.064 mol, yield 77%) over about 30 minutes. After the completion of the dropwise addition, the liquid was stirred for 60 minutes, and then the reaction liquid was concentrated under reduced pressure to about 1/3 volume. To the concentrated liquid, ethyl acetate (500 mL, manufactured by Junsei Chemical Co., Ltd., special grade) was added for extraction. The remaining aqueous phase was further re-extracted with ethyl acetate (500 mL). These extracted organic phases (ethyl acetate phase) were combined and concentrated under reduced pressure. The residue obtained by concentration was purified by silica gel column chromatography to obtain N-methyl-2-mercapto-4-butyrolactam (5.4 g, 0.041 mol, yield 64%).
[合成例10]
2−ブロモ−4−ブチロラクタムの合成
合成例7で記載したと同様の方法により得られた2,4−ジブロモ酪酸ブロミドを使用して、40%メチルアミン水溶液の代わりにアンモニア水を使用した以外は、合成例8に従って2,4−ジブロモ酪酸アミド(12.4g、0.076mol、mp.79℃、収率63%)を得た。さらに、N−メチル−2,4−ジブロモ酪酸アミドの代わりに、この2,4−ジブロモ酪酸アミドを使用した以外は、合成例8と同様の方法により2−ブロモ−4−ブチロラクタム(3.4g、0.021mol、収率27%)を取得した。
[Synthesis Example 10]
Synthesis of 2-bromo-4-butyrolactam Using 2,4-dibromobutyric acid bromide obtained by the same method as described in Synthesis Example 7, except that ammonia water was used instead of 40% aqueous methylamine solution According to Synthesis Example 8, 2,4-dibromobutyric acid amide (12.4 g, 0.076 mol, mp. 79 ° C., yield 63%) was obtained. Further, 2-bromo-4-butyrolactam (3.4 g) was prepared in the same manner as in Synthesis Example 8 except that this 2,4-dibromobutyric acid amide was used instead of N-methyl-2,4-dibromobutyric acid amide. 0.021 mol, 27% yield).
[合成例11]
2−メルカプト−4−ブチロラクタムの合成
N−メチル−2−ブロモ−4−ブチロラクタムの代わりに、2−ブロモ−4−ブチロラクタム(3.4g、0.021mol)を使用した以外は、合成例9に従って2−メルカプト−4−ブチロラクタム(1.7g、0.014mol、収率69%)を合成した。
[Synthesis Example 11]
Synthesis of 2-mercapto-4-butyrolactam According to Synthesis Example 9 except that 2-bromo-4-butyrolactam (3.4 g, 0.021 mol) was used instead of N-methyl-2-bromo-4-butyrolactam. 2-mercapto-4-butyrolactam (1.7 g, 0.014 mol, 69% yield) was synthesized.
[くせ毛サンプル]
20代日本人女性の化学的処理を行っていないくせ毛10本を1単位として根本の部分を接着し、長さ20cmの毛束となるようにして、くせ毛サンプルを作成した。
[Skin hair sample]
A comb hair sample was prepared by adhering the root portion of 10 wrinkled hairs of a Japanese woman in their twenties as a unit to form a hair bundle having a length of 20 cm.
この毛束をシャンプー、リンス、ヘアウオーター評価に用いた。
実施例1〜3
[シャンプー液の調製]
シャンプーに使用する成分比率は、表1に示す割合で以下の手順に従って調製した。
This hair bundle was used for shampoo, rinsing and hair water evaluation.
Examples 1-3
[Preparation of shampoo solution]
The component ratio used for the shampoo was prepared according to the following procedure at the ratio shown in Table 1.
精製水25gを70℃に加温し、70℃となった精製水にラウリルポリオキシエチレン硫酸エステルトリエタノールアミン塩水溶液、ラウリルポリオキシエチレン硫酸エステルソーダ塩水溶液、ラウロイルジエタノールアミド、ポリエチレングリコール400の順に撹拌しながら加えた。均一になったところで放冷し、クエン酸、リン酸水素二ナトリウムを撹拌しながら加えpHを調整した。調整後の液に、合成例1で得られたチオグリコール酸2−メトキシエチルエステルを加えて再び撹拌した。充分に撹拌した後に、pHを再度調整した。pH調整後のシャンプー液が100gとなるように精製水を加え、再び均一となるようにガラス棒にて撹拌した。 25 g of purified water was heated to 70 ° C., and the purified water at 70 ° C. was added in the order of lauryl polyoxyethylene sulfate triethanolamine aqueous solution, lauryl polyoxyethylene sulfate sodium carbonate aqueous solution, lauroyl diethanolamide, polyethylene glycol 400 in this order. Added with stirring. When it became uniform, it was allowed to cool, and citric acid and disodium hydrogen phosphate were added with stirring to adjust the pH. The thioglycolic acid 2-methoxyethyl ester obtained in Synthesis Example 1 was added to the liquid after the adjustment and stirred again. After thorough stirring, the pH was adjusted again. Purified water was added so that the shampoo solution after pH adjustment was 100 g, and the mixture was stirred with a glass rod so as to be uniform again.
[処理前のくせ毛度測定]
くせ毛サンプルを0.5%ラウリル硫酸ナトリウム(花王株式会社製 エマール2Fペーストを使用)水溶液に温度40℃で30分間浸漬し、その後、約25℃の水中ですすぎ洗いを2回行い、水分を軽く拭き取った後に、毛束の接着部分が上になるように吊して約
25℃で風乾した。
[Measurement of hair loss before treatment]
Soak the hair sample in an aqueous solution of 0.5% sodium lauryl sulfate (using Emar 2F paste manufactured by Kao Corporation) at a temperature of 40 ° C for 30 minutes, and then rinse twice in water at about 25 ° C to lighten the moisture. After wiping, the hair bundle was hung so that the bonded portion was on the top, and air-dried at about 25 ° C.
乾燥後のくせ毛10本を吊した状態にて上端から下端までのそれぞれの長さを測定した(L1cm)。次にこの毛髪を引っ張り、まっすぐな状態での毛髪の長さを測定した(L0cm)。 Each length from the upper end to the lower end was measured (L1 cm) in a state where 10 hairs after drying were suspended. Next, this hair was pulled and the length of the hair in a straight state was measured (L0 cm).
次の式により処理前くせ毛度を計算した。
処理前くせ毛度=L1cm/L0cm
なお、くせ毛度は、1に近くなる程まっすぐであることを意味する。
The combing hair degree before processing was calculated by the following formula.
Comb hair before treatment = L1cm / L0cm
In addition, it means that a hairline degree is so straight that it is close to 1.
[くせ毛直し処理]
くせ毛サンプルをガラス板上に乗せ、調製したシャンプー液1gを毛髪にパスツールピペットにて約1cm間隔で滴下した。滴下後のシャンプー液が均一に毛髪に広がるようにガラス棒でなじませ、充分になじませた後に、櫛でまっすぐになるように伸ばした。のばした毛髪にポリ塩化ビニリデン製の包装用ラップフィルム(製品名:サランラップ(R)、旭化成株式会社製)を掛けた。処理をした毛髪をガラス板ごと35℃の恒温オーブンに20分間放置した。その後、ガラス板から外した毛束を約25℃の水中ですすぎ洗いを2回行い、水分を軽く拭き取った後に、毛束の接着部分が上になるように吊して約25℃で風乾した。
[Hair treatment]
The comb hair sample was placed on a glass plate, and 1 g of the prepared shampoo solution was dropped on the hair with a Pasteur pipette at about 1 cm intervals. After dripping, the shampoo solution was spread with a glass rod so that the shampoo solution spread evenly over the hair. The extended hair was covered with a wrapping film made of polyvinylidene chloride (product name: Saran Wrap (R), manufactured by Asahi Kasei Co., Ltd.). The treated hair was left in a constant temperature oven at 35 ° C. for 20 minutes together with the glass plate. After that, the hair bundle removed from the glass plate was rinsed twice in water at about 25 ° C., and after lightly wiping off the moisture, it was hung so that the bonded portion of the hair bundle was on top and air-dried at about 25 ° C. .
風乾後、乾燥後のくせ毛10本を吊した状態にて上端から下端までの長さを測定した(L3cm)。次にこの毛髪を引っ張り、まっすぐな状態での毛髪の長さを測定した(L2cm)。 After air-drying, the length from the upper end to the lower end was measured (L3 cm) in a state where 10 dried comb hairs were suspended. Next, the hair was pulled and the length of the hair in a straight state was measured (L2 cm).
次の式により処理後くせ毛度を計算した。
処理後くせ毛度=L3cm/L2cm
くせ毛度改善率は、以下の式により計算した。計算には、処理前後の測定値の10本の平均値を使用して計算した。
The combing hair degree was calculated after the treatment according to the following formula.
Comb hair after treatment = L3cm / L2cm
The improvement rate of the hair loss was calculated by the following formula. For the calculation, the average value of 10 measured values before and after the treatment was used.
くせ毛改善率(%)=
[(処理後くせ毛度−処理前くせ毛度)÷処理前くせ毛度]×100
[毛髪破断テスト]
[処理前毛髪の破断テスト]
市販のテンションゲージ(大場計器製作所製 丸型(棒)ゲージ O−BT)が動かないようにテーブル面に水平となるように固定した。テンションゲージのL字金具部分に1本の毛髪をU字型に引っかけた。毛髪の両端を手に持ち、毛髪が切れるまでゆっくりと引っ張った。切れた際に、テンションゲージの動きがとまり、この数値を記録した。
Comb hair improvement rate (%) =
[(Combination hair after treatment-Comb hair before treatment) ÷ Comb hair before treatment] × 100
[Hair break test]
[Break test of hair before treatment]
A commercially available tension gauge (round (bar) gauge O-BT manufactured by Oba Keiki Seisakusho) was fixed so as to be horizontal on the table surface. One hair was hooked in a U shape on the L-shaped metal part of the tension gauge. Holding both ends of the hair in hand, slowly pulled until the hair was cut. When it was cut, the tension gauge stopped and recorded this value.
処理前の毛髪を50本測定し、その平均値を処理前の毛髪強度(W0)とした。
[処理後毛髪の破断テスト]
シャンプー液による毛髪の処理を10回繰り返して行い、毛髪破断テストサンプルとした。処理後の乾燥したくせ毛10本をテンションゲージを使用し、処理前毛髪の破断テストと同様の測定を行った。得られた測定値の平均値を処理後の毛髪強度(W1)とした。
50 hairs before treatment were measured, and the average value was defined as the hair strength (W0) before treatment.
[Break test of hair after treatment]
The hair treatment with the shampoo solution was repeated 10 times to obtain a hair breakage test sample. Ten dry dry hairs after the treatment were measured using a tension gauge in the same manner as the break test of the pre-treatment hair. The average value of the obtained measured values was defined as the hair strength (W1) after the treatment.
破断強度低下率は以下の式により算出した。
破断強度低下率(%)=[(W0−W1)÷W0]×100
以上の結果を表1に示す。
実施例4〜6
メルカプト化合物を合成例2で得られたチオグリコール酸2−エトキシエチルエステルに替え、表1に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を
表1に示す。
実施例7〜9
メルカプト化合物を合成例3で得られたチオ乳酸2−エトキシエチルエステルに替え、表1に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表1に示す。
実施例10〜12
メルカプト化合物を合成例4で得られた3−メルカプトプロピオン酸2−エトキシエチルエステルに替え、表2に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表2に示す。
実施例13〜15
メルカプト化合物を合成例5で得られた2−メルカプト−4−ブタノリドに替え、表2に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表2に示す。実施例16〜18
メルカプト化合物を合成例6で得られた2−メルカプトシクロペンタノンに替え、表2に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表2に示す。
The breaking strength reduction rate was calculated by the following formula.
Breaking strength reduction rate (%) = [(W0−W1) ÷ W0] × 100
The results are shown in Table 1.
Examples 4-6
The mercapto compound was replaced with thioglycolic acid 2-ethoxyethyl ester obtained in Synthesis Example 2, and the procedure was performed according to Examples 1 to 3 except that the component ratios shown in Table 1 were followed. The results are shown in Table 1.
Examples 7-9
The mercapto compound was replaced with the thiolactic acid 2-ethoxyethyl ester obtained in Synthesis Example 3, and the procedure was performed according to Examples 1 to 3 except that the component ratios shown in Table 1 were followed. The results are shown in Table 1.
Examples 10-12
The mercapto compound was replaced with 3-mercaptopropionic acid 2-ethoxyethyl ester obtained in Synthesis Example 4, and the procedure was performed according to Examples 1 to 3 except that the component ratios shown in Table 2 were followed. The results are shown in Table 2.
Examples 13-15
The same procedure as in Examples 1 to 3 was performed except that the mercapto compound was replaced with 2-mercapto-4-butanolide obtained in Synthesis Example 5 and the component ratios shown in Table 2 were followed. The results are shown in Table 2. Examples 16-18
The mercapto compound was replaced with 2-mercaptocyclopentanone obtained in Synthesis Example 6, and the same procedure as in Examples 1 to 3 was performed except that the component ratios shown in Table 2 were followed. The results are shown in Table 2.
実施例19〜21
メルカプト化合物を合成例9で得られたN−メチル−2−メルカプト−4−ブチロラクタムに替え、表3に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表3に示す。
実施例22〜24
メルカプト化合物を合成例11で得られた2−メルカプト−4−ブチロラクタムに替え、表3に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表3に示す。
比較例1〜3
メルカプト化合物の代わりに亜硫酸ナトリウム(純正化学株式会社製)を使用し、表3に示す成分比率に従った以外は、実施例1〜3に準じて行った。その結果を表3に示す。
Examples 19-21
The mercapto compound was replaced with N-methyl-2-mercapto-4-butyrolactam obtained in Synthesis Example 9, and the same procedure as in Examples 1 to 3 was performed except that the component ratios shown in Table 3 were followed. The results are shown in Table 3.
Examples 22-24
The mercapto compound was replaced with 2-mercapto-4-butyrolactam obtained in Synthesis Example 11, and the procedure was performed according to Examples 1 to 3 except that the component ratios shown in Table 3 were followed. The results are shown in Table 3.
Comparative Examples 1-3
It carried out according to Examples 1-3 except using sodium sulfite (made by Junsei Chemical Co., Ltd.) instead of the mercapto compound and following the component ratios shown in Table 3. The results are shown in Table 3.
実施例25
[リンス液の調製]
リンス液に使用する成分比率は、表4に示す割合で以下の手順に従って調製した。
Example 25
[Preparation of rinse solution]
The component ratio used for the rinse liquid was prepared according to the following procedure at the ratio shown in Table 4.
精製水60gにグリセリンを加え70℃に加温して、70℃のまま保温して水相液とした。別の容器に、セチルアルコール、シリコン油、ポリオキシエチレンオレイルエーテル、ステアリルトリメチルアンモニウムクロリドを混合して、加熱融解して70℃とした(油相)。激しく撹拌しながら油相に水相を加えた。 Glycerin was added to 60 g of purified water, heated to 70 ° C., and kept at 70 ° C. to obtain an aqueous phase solution. In another container, cetyl alcohol, silicon oil, polyoxyethylene oleyl ether, and stearyltrimethylammonium chloride were mixed and heated to melt to 70 ° C. (oil phase). The aqueous phase was added to the oil phase with vigorous stirring.
その後、冷却しながら更に混合した。冷却した液に、クエン酸、リン酸水素二ナトリウムを撹拌しながら加えpHを調整した。調整後の液に、合成例2で得られたチオグリコール酸2−エトキシエチルエステルを加えて再び撹拌した。充分に撹拌した後に、pHを再度調整した。pH調整後のリンス液が100gとなるように精製水を加え、再び均一となるようにガラス棒で撹拌した。 Then, it further mixed, cooling. To the cooled liquid, citric acid and disodium hydrogen phosphate were added with stirring to adjust the pH. To the adjusted liquid, the thioglycolic acid 2-ethoxyethyl ester obtained in Synthesis Example 2 was added and stirred again. After thorough stirring, the pH was adjusted again. Purified water was added so that the rinsing solution after pH adjustment was 100 g, and the mixture was stirred with a glass rod so as to be uniform again.
[くせ毛直し効果の測定]
くせ毛サンプルをガラス板上に乗せ、調製したリンス液1gを毛髪にパスツールピペットにて約1cm間隔で滴下した。滴下後のリンス液が均一に毛髪に広がるようにガラス棒でなじませ、充分になじませた後に、櫛でまっすぐになるように伸ばした。
[Measurement of hair straightening effect]
The comb hair sample was placed on a glass plate, and 1 g of the prepared rinse solution was dropped onto the hair with a Pasteur pipette at about 1 cm intervals. After dripping, the rinse solution was spread with a glass rod so that it spreads evenly over the hair. After thoroughly blended, it was straightened with a comb.
のばした毛髪にポリ塩化ビニリデン製の包装用ラップフィルム(製品名:サランラップ(R)、旭化成株式会社製)を掛けた。処理をした毛髪をガラス板ごと35℃の恒温オーブンに20分間放置した。その後、ガラス板から外した毛束を約25℃の水中ですすぎ洗いを1回行い、水分を軽く拭き取った後に、毛束の接着部分が上になるように吊して約25℃で風乾した。 The extended hair was covered with a wrapping film made of polyvinylidene chloride (product name: Saran Wrap (R), manufactured by Asahi Kasei Co., Ltd.). The treated hair was left in a constant temperature oven at 35 ° C. for 20 minutes together with the glass plate. After that, the hair bundle removed from the glass plate was rinsed once in water at about 25 ° C., and after lightly wiping off moisture, it was hung so that the bonded portion of the hair bundle was on top and air-dried at about 25 ° C. .
風乾後、乾燥後のくせ毛をシャンプー処理評価の場合と同様に、処理後くせ毛度の測定およびリンス処理を10回繰り返した後の毛髪破断テストを行った。その結果を表4に示す。
実施例26
メルカプト化合物を合成例3で得られたチオ乳酸2−エトキシエチルエステルに替え、表4に示す成分比率に従った以外は、実施例25に準じて行った。その結果を表4に示す。
実施例27
メルカプト化合物を合成例5で得られた2−メルカプト−4−ブタノリドに替え、表4に示す成分比率に従った以外は、実施例25に準じて行った。その結果を表4に示す。
実施例28
メルカプト化合物を合成例6で得られた2−メルカプトシクロペンタノンに替え、表4に示す成分比率に従った以外は、実施例25に準じて行った。その結果を表4に示す。
実施例29
メルカプト化合物を合成例11で得られた2−メルカプト−4−ブチロラクタムに替え、表4に示す成分比率に従った以外は、実施例25に準じて行った。その結果を表4に示す。
比較例4、5
メルカプト化合物の代わりに亜硫酸ナトリウムを使用し、表4に示す成分比率に従った以外は、実施例25に準じて行った。その結果を表4に示す。
After air drying, the hair after drying was subjected to a hair breakage test after 10 times of measurement of the comb hair after the treatment and rinsing treatment in the same manner as in the shampoo treatment evaluation. The results are shown in Table 4.
Example 26
The mercapto compound was replaced with the thiolactic acid 2-ethoxyethyl ester obtained in Synthesis Example 3, and the procedure was performed according to Example 25 except that the component ratios shown in Table 4 were followed. The results are shown in Table 4.
Example 27
The mercapto compound was replaced with 2-mercapto-4-butanolide obtained in Synthesis Example 5, and the procedure was performed according to Example 25 except that the component ratios shown in Table 4 were followed. The results are shown in Table 4.
Example 28
The same procedure as in Example 25 was performed except that the mercapto compound was replaced with 2-mercaptocyclopentanone obtained in Synthesis Example 6 and the component ratios shown in Table 4 were followed. The results are shown in Table 4.
Example 29
The mercapto compound was replaced with 2-mercapto-4-butyrolactam obtained in Synthesis Example 11, and the procedure was performed according to Example 25 except that the component ratios shown in Table 4 were followed. The results are shown in Table 4.
Comparative Examples 4 and 5
It carried out according to Example 25 except having used sodium sulfite instead of the mercapto compound and having followed the component ratio shown in Table 4. The results are shown in Table 4.
実施例30
[ヘアウオーター液の調製]
ヘアウオーター液に使用する成分比率は、表5に示す割合で以下の手順に従って調製した。
Example 30
[Preparation of hair water solution]
The component ratio used for the hair water solution was prepared according to the following procedure at the ratio shown in Table 5.
エチルアルコールにプロピレングリコール、ポリオキシエチレンステアリルエーテルを加えて溶解した。これにポリビニルピロリドンを加え湿潤させ、かき混ぜながら精製水65gを徐々に加えた。水を加えた液にリン酸水素二ナトリウム、リン酸二水素ナトリウム
を撹拌しながら加えpHを調整した。調整後の液に、合成例2で得られたチオグリコール酸2−エトキシエチルエステルを加えて再び撹拌した。充分に撹拌した後に、pHを再度調整した。pH調整後のヘアウオーター液が100gとなるように精製水を加え、撹拌した。
Propylene glycol and polyoxyethylene stearyl ether were added to ethyl alcohol and dissolved. Polyvinylpyrrolidone was added to this and moistened, and 65 g of purified water was gradually added while stirring. To the liquid to which water was added, disodium hydrogen phosphate and sodium dihydrogen phosphate were added with stirring to adjust the pH. To the adjusted liquid, the thioglycolic acid 2-ethoxyethyl ester obtained in Synthesis Example 2 was added and stirred again. After thorough stirring, the pH was adjusted again. Purified water was added and stirred so that the hair water solution after pH adjustment was 100 g.
[くせ毛直し効果の測定]
くせ毛サンプルの一端をクリップで挟み、保持台に括りつけて吊した。吊した毛髪にハンドスプレーを用いて、ヘアウオーターを均一にぬれる様に噴霧した。吊した毛髪の一端に約5gの重りを付けて10分間、30℃で放置した後に重りを外し、風乾した。
[Measurement of hair straightening effect]
One end of the hair sample was pinched with a clip and tied to a holding base and suspended. Using a hand spray on the suspended hair, the hair water was sprayed so as to be evenly wetted. A weight of about 5 g was attached to one end of the suspended hair and left at 30 ° C. for 10 minutes, and then the weight was removed and air-dried.
風乾後、乾燥後のくせ毛をシャンプー処理評価の場合と同様に、処理後くせ毛度の測定およびヘアウオーター処理を10回繰り返した後の毛髪破断テストを行った。
以上の結果を表5に示す。
実施例31
メルカプト化合物を合成例3で得られたチオ乳酸2−エトキシエチルエステルに替え、表5に示す成分比率に従った以外は、実施例30に準じて行った。その結果を表5に示す。
実施例32
メルカプト化合物を合成例5で得られた2−メルカプト−4−ブタノリドに替え、表5に示す成分比率に従った以外は、実施例30に準じて行った。その結果を表5に示す。
比較例6、7
メルカプト化合物の代わりに亜硫酸ナトリウムを使用し、表5に示す成分比率に従った以外は、実施例30に準じて行った。その結果を表5に示す。
After air-drying, the hair after drying was subjected to a hair breakage test after 10 times of measurement of the post-treatment combing hair degree and hair water treatment, as in the case of shampoo treatment evaluation.
The results are shown in Table 5.
Example 31
The mercapto compound was replaced with the thiolactic acid 2-ethoxyethyl ester obtained in Synthesis Example 3, and the procedure was performed according to Example 30, except that the component ratios shown in Table 5 were followed. The results are shown in Table 5.
Example 32
The mercapto compound was replaced with 2-mercapto-4-butanolide obtained in Synthesis Example 5, and the procedure was performed according to Example 30 except that the component ratios shown in Table 5 were followed. The results are shown in Table 5.
Comparative Examples 6 and 7
It carried out according to Example 30 except having used sodium sulfite instead of the mercapto compound and having followed the component ratio shown in Table 5. The results are shown in Table 5.
以上の結果から、本発明のメルカプト化合物を含有する毛髪矯正剤は、弱酸性から弱アルカリ性までの広いpH領域において、毛髪の変形矯正効果が高いことが分かる。さらに、弱酸性から中性のpH領域においては、毛髪の変形矯正効果がより一層高い上に、毛髪の損傷が少ないことが明らかである。 From the above results, it can be seen that the hair straightener containing the mercapto compound of the present invention has a high hair deformation correction effect in a wide pH range from weak acidity to weak alkalinity. Furthermore, it is clear that in a weakly acidic to neutral pH range, the hair deformation correction effect is even higher and the hair is less damaged.
Claims (11)
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