JP2021187822A - Hair treatment agent - Google Patents
Hair treatment agent Download PDFInfo
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- JP2021187822A JP2021187822A JP2020106540A JP2020106540A JP2021187822A JP 2021187822 A JP2021187822 A JP 2021187822A JP 2020106540 A JP2020106540 A JP 2020106540A JP 2020106540 A JP2020106540 A JP 2020106540A JP 2021187822 A JP2021187822 A JP 2021187822A
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- 239000003795 chemical substances by application Substances 0.000 claims abstract description 46
- JOOXCMJARBKPKM-UHFFFAOYSA-N 4-oxopentanoic acid Chemical compound CC(=O)CCC(O)=O JOOXCMJARBKPKM-UHFFFAOYSA-N 0.000 claims abstract description 40
- 229940040102 levulinic acid Drugs 0.000 claims abstract description 20
- 230000000694 effects Effects 0.000 abstract description 37
- 239000002253 acid Substances 0.000 description 23
- 230000003700 hair damage Effects 0.000 description 20
- 238000010494 dissociation reaction Methods 0.000 description 14
- 230000005593 dissociations Effects 0.000 description 14
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000011156 evaluation Methods 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000003638 chemical reducing agent Substances 0.000 description 8
- 230000006378 damage Effects 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 7
- 125000003396 thiol group Chemical group [H]S* 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 6
- 238000002156 mixing Methods 0.000 description 6
- 159000000000 sodium salts Chemical class 0.000 description 6
- 238000012360 testing method Methods 0.000 description 5
- 230000002378 acidificating effect Effects 0.000 description 4
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 4
- 235000001014 amino acid Nutrition 0.000 description 4
- 150000002500 ions Chemical class 0.000 description 4
- 229910052742 iron Inorganic materials 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 239000004475 Arginine Substances 0.000 description 3
- ODKSFYDXXFIFQN-BYPYZUCNSA-P L-argininium(2+) Chemical compound NC(=[NH2+])NCCC[C@H]([NH3+])C(O)=O ODKSFYDXXFIFQN-BYPYZUCNSA-P 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
- -1 alkyl ether carboxylic acid amino acid salt Chemical class 0.000 description 3
- 150000001413 amino acids Chemical class 0.000 description 3
- ODKSFYDXXFIFQN-UHFFFAOYSA-N arginine Natural products OC(=O)C(N)CCCNC(N)=N ODKSFYDXXFIFQN-UHFFFAOYSA-N 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 230000007935 neutral effect Effects 0.000 description 3
- 150000007524 organic acids Chemical class 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 239000008213 purified water Substances 0.000 description 3
- 239000002453 shampoo Substances 0.000 description 3
- 238000003756 stirring Methods 0.000 description 3
- PMNLUUOXGOOLSP-UHFFFAOYSA-N 2-mercaptopropanoic acid Chemical compound CC(S)C(O)=O PMNLUUOXGOOLSP-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- MHAJPDPJQMAIIY-UHFFFAOYSA-N Hydrogen peroxide Chemical compound OO MHAJPDPJQMAIIY-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- 241000209094 Oryza Species 0.000 description 2
- 235000007164 Oryza sativa Nutrition 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- UFULAYFCSOUIOV-UHFFFAOYSA-N cysteamine Chemical compound NCCS UFULAYFCSOUIOV-UHFFFAOYSA-N 0.000 description 2
- 239000002552 dosage form Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000000118 hair dye Substances 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 229960003151 mercaptamine Drugs 0.000 description 2
- 230000001590 oxidative effect Effects 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 235000009566 rice Nutrition 0.000 description 2
- JHJLBTNAGRQEKS-UHFFFAOYSA-M sodium bromide Chemical compound [Na+].[Br-] JHJLBTNAGRQEKS-UHFFFAOYSA-M 0.000 description 2
- 239000007921 spray Substances 0.000 description 2
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- 208000034656 Contusions Diseases 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- WHUUTDBJXJRKMK-UHFFFAOYSA-N Glutamic acid Natural products OC(=O)C(N)CCC(O)=O WHUUTDBJXJRKMK-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- IMQLKJBTEOYOSI-GPIVLXJGSA-N Inositol-hexakisphosphate Chemical compound OP(O)(=O)O[C@H]1[C@H](OP(O)(O)=O)[C@@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@H](OP(O)(O)=O)[C@@H]1OP(O)(O)=O IMQLKJBTEOYOSI-GPIVLXJGSA-N 0.000 description 1
- 102000011782 Keratins Human genes 0.000 description 1
- 108010076876 Keratins Proteins 0.000 description 1
- CKLJMWTZIZZHCS-REOHCLBHSA-N L-aspartic acid Chemical compound OC(=O)[C@@H](N)CC(O)=O CKLJMWTZIZZHCS-REOHCLBHSA-N 0.000 description 1
- WHUUTDBJXJRKMK-VKHMYHEASA-N L-glutamic acid Chemical compound OC(=O)[C@@H](N)CCC(O)=O WHUUTDBJXJRKMK-VKHMYHEASA-N 0.000 description 1
- HNDVDQJCIGZPNO-YFKPBYRVSA-N L-histidine Chemical compound OC(=O)[C@@H](N)CC1=CN=CN1 HNDVDQJCIGZPNO-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-YFKPBYRVSA-N L-lysine Chemical compound NCCCC[C@H](N)C(O)=O KDXKERNSBIXSRK-YFKPBYRVSA-N 0.000 description 1
- KDXKERNSBIXSRK-UHFFFAOYSA-N Lysine Natural products NCCCCC(N)C(O)=O KDXKERNSBIXSRK-UHFFFAOYSA-N 0.000 description 1
- 239000004472 Lysine Substances 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- IMQLKJBTEOYOSI-UHFFFAOYSA-N Phytic acid Natural products OP(O)(=O)OC1C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C(OP(O)(O)=O)C1OP(O)(O)=O IMQLKJBTEOYOSI-UHFFFAOYSA-N 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000013543 active substance Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 239000002280 amphoteric surfactant Substances 0.000 description 1
- 229920006318 anionic polymer Polymers 0.000 description 1
- 239000003945 anionic surfactant Substances 0.000 description 1
- 235000003704 aspartic acid Nutrition 0.000 description 1
- SWXQKHHHCFXQJF-UHFFFAOYSA-N azane;hydrogen peroxide Chemical compound [NH4+].[O-]O SWXQKHHHCFXQJF-UHFFFAOYSA-N 0.000 description 1
- OQFSQFPPLPISGP-UHFFFAOYSA-N beta-carboxyaspartic acid Natural products OC(=O)C(N)C(C(O)=O)C(O)=O OQFSQFPPLPISGP-UHFFFAOYSA-N 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 208000034526 bruise Diseases 0.000 description 1
- 150000001720 carbohydrates Chemical class 0.000 description 1
- 229920006317 cationic polymer Polymers 0.000 description 1
- 239000003093 cationic surfactant Substances 0.000 description 1
- 239000002537 cosmetic Substances 0.000 description 1
- 235000018417 cysteine Nutrition 0.000 description 1
- XUJNEKJLAYXESH-UHFFFAOYSA-N cysteine Natural products SCC(N)C(O)=O XUJNEKJLAYXESH-UHFFFAOYSA-N 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 125000002228 disulfide group Chemical group 0.000 description 1
- 239000003814 drug Substances 0.000 description 1
- 229940079593 drug Drugs 0.000 description 1
- 239000003205 fragrance Substances 0.000 description 1
- 235000013922 glutamic acid Nutrition 0.000 description 1
- 239000004220 glutamic acid Substances 0.000 description 1
- 230000003676 hair loss Effects 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- HNDVDQJCIGZPNO-UHFFFAOYSA-N histidine Natural products OC(=O)C(N)CC1=CN=CN1 HNDVDQJCIGZPNO-UHFFFAOYSA-N 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 150000007529 inorganic bases Chemical group 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
- 235000011090 malic acid Nutrition 0.000 description 1
- 229910021645 metal ion Inorganic materials 0.000 description 1
- 150000007522 mineralic acids Chemical class 0.000 description 1
- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 239000002736 nonionic surfactant Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007530 organic bases Chemical class 0.000 description 1
- 239000007800 oxidant agent Substances 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 239000000467 phytic acid Substances 0.000 description 1
- 229940068041 phytic acid Drugs 0.000 description 1
- 235000002949 phytic acid Nutrition 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920000137 polyphosphoric acid Polymers 0.000 description 1
- 102000004196 processed proteins & peptides Human genes 0.000 description 1
- 108090000765 processed proteins & peptides Proteins 0.000 description 1
- 235000018102 proteins Nutrition 0.000 description 1
- 102000004169 proteins and genes Human genes 0.000 description 1
- 108090000623 proteins and genes Proteins 0.000 description 1
- 238000003303 reheating Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- XUXNAKZDHHEHPC-UHFFFAOYSA-M sodium bromate Chemical compound [Na+].[O-]Br(=O)=O XUXNAKZDHHEHPC-UHFFFAOYSA-M 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- 230000001629 suppression Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 150000003628 tricarboxylic acids Chemical class 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、毛髪の傷みと弾力の低下を十分に抑制し、かつ、良好な縮毛矯正効果を有する毛髪処理剤に関する。 The present invention relates to a hair treatment agent that sufficiently suppresses hair damage and decrease in elasticity and has a good hair straightening effect.
一般的な縮毛矯正剤は、主成分の還元剤、酸化剤の作用及び高温での機械的処理によりクセを矯正することができる。具体的には、チオグリコール酸又はその塩、システアミン又はその塩等の還元剤と、アンモニア水、モノエタノールアミン、炭酸水素アンモニウム、アルギニン等のアルカリ剤を含有する第１剤を毛髪に塗布することによりケラチンタンパクに存在するジスルフィド結合を還元開裂した後中間水洗し、ドライヤーなどで乾燥し、アイロンによる高温での機械的処理によりストレート状に伸ばした上で、過酸化水素あるいは臭素酸ナトリウム等の酸化剤を主成分とする第２剤で処理して、ジスルフィド基を酸化再形成させ、毛髪をストレート状に固定する。しかし、アルカリ性の第１剤を作用させると毛髪が膨潤軟化し、ドライヤーなどでの乾燥及びアイロンによる高温での機械的処理により毛髪の傷みと弾力が低下し、処理後の時間経過に伴い毛髪の傷みにより感触が悪くなるという問題がある。このため、毛髪の傷みと弾力の低下を十分に抑制し、かつ、良好な縮毛矯正効果を有する毛髪処理剤の開発が望まれている。 A general hair straightener can straighten habits by the action of a reducing agent and an oxidizing agent as main components and mechanical treatment at a high temperature. Specifically, the first agent containing a reducing agent such as thioglycolic acid or a salt thereof, cysteamine or a salt thereof, and an alkaline agent such as aqueous ammonia, monoethanolamine, ammonium hydrogen peroxide, and arginine is applied to the hair. After reducing and cleaving the disulfide bond present in the keratin protein, it is washed with intermediate water, dried with a dryer, etc., stretched straight by mechanical treatment at high temperature with an iron, and then oxidized with hydrogen peroxide or sodium bromide. It is treated with a second agent containing an agent as a main component to oxidatively reform the disulfide group and fix the hair in a straight shape. However, when the first alkaline agent is applied, the hair swells and softens, and the hair is damaged and loses elasticity due to drying with a dryer and mechanical treatment at high temperature with an iron. There is a problem that the feel becomes worse due to the damage. Therefore, it is desired to develop a hair treatment agent that sufficiently suppresses hair damage and decrease in elasticity and has a good hair straightening effect.
毛髪の傷みと弾力の低下の少ない縮毛矯正方法及び毛髪処理剤として、特許文献１には、Ｒ１−Ｏ−（ＣＨ２ＣＨ２Ｏ）ｎＣＨ２ＣＯＯＭ（式中、Ｒ１は飽和又は不飽和の炭化水素基を示し、ｎは１〜１０の数を示し、Ｍはリシン、ヒスチジン又はアルギニンを示す。）で表されるアルキルエーテルカルボン酸アミノ酸塩及び還元剤を含み、ｐＨが中性領域であり、前記還元剤が、システアミン及びその塩からなる群から選択される少なくとも１種である縮毛矯正用の毛髪処理剤が開示されている。当該特許の明細書において「中性領域」とは、ｐＨ６．０〜８．０の範囲を意味するとの記載がある。この毛髪処理剤では、ｐＨが中性領域であっても、弱〜強アルカリ性における場合と同等以上のストレートデザイン形成効果を有し、かつ毛髪の傷みを抑制することが可能ではあるが、毛髪の等電点付近であるｐＨ４．５〜５．５よりアルカリ寄りであるため、毛髪の傷みと弾力の低下を十分に解消することができない。As bruise and elasticity decrease less hair straightening method and the hair treatment agent of the hair, Patent Document 1, in R 1 -O- (CH 2 CH 2 O) n CH 2 COOM ( wherein, R 1 is a saturated or It represents an unsaturated hydrocarbon group, n represents a number of 1 to 10, M represents an alkyl ether carboxylic acid amino acid salt represented by lysine, histidine or arginine) and a reducing agent, and the pH is neutral. A hair treatment agent for straightening hair, which is a region and the reducing agent is at least one selected from the group consisting of arginine and a salt thereof, is disclosed. In the specification of the patent, it is stated that the "neutral region" means the range of pH 6.0 to 8.0. This hair treatment agent has a straight design forming effect equal to or higher than that in the case of weak to strong alkalinity even in the neutral pH range, and can suppress hair damage, but it is possible to suppress hair damage. Since the pH is closer to alkaline than the pH of 4.5 to 5.5, which is near the isoelectric point, it is not possible to sufficiently eliminate the damage to the hair and the decrease in elasticity.
毛髪の傷みと弾力の低下の少ない縮毛矯正方法及び毛髪処理剤として、特許文献２には、縮毛矯正剤として、チオグリコール酸と、有機酸及び／又はリン酸と、有機酸塩及び／又はリン酸塩と、を含み酸性である、毛髪処理剤組成物が開示されている。この方法では、毛髪の傷みを十分に抑制し、かつ、良好な縮毛矯正効果を発現できることが可能ではあるが、毛髪の弾力の低下を十分に解消することができない。また、有機酸及び／又はリン酸は、チオグリコール酸の酸解離定数に近い酸解離定数を有するものを選択することが好ましく、チオグリコール酸は、そのほとんどが解離ないし中和されておらず、酸の状態で存在し、酸性ｐＨに調整することないし酸性ｐＨを維持することが容易になると考えられるとの記載がある。すなわち、当該特許に配合されている有機酸及び／又はリン酸の少なくとも１種は、チオグリコール酸の酸解離定数に近い酸解離定数を有し、チオグリコール酸のほとんどが解離ないし中和されておらず、酸の状態で存在することが当該特許の効果を提供するための必要条件である。 As a hair straightening method and a hair treatment agent with less damage to hair and a decrease in elasticity, Patent Document 2 describes thioglycolic acid, an organic acid and / or phosphoric acid, an organic acid salt and / as a hair straightening agent. Alternatively, a hair treatment agent composition containing and acid phosphate is disclosed. With this method, it is possible to sufficiently suppress the damage to the hair and to exhibit a good hair straightening effect, but it is not possible to sufficiently eliminate the decrease in the elasticity of the hair. Further, it is preferable to select an organic acid and / or a phosphoric acid having an acid dissociation constant close to the acid dissociation constant of thioglycolic acid, and most of the thioglycolic acid is not dissociated or neutralized. There is a description that it exists in an acidic state, and it is considered that it is easy to maintain the acidic pH without adjusting to the acidic pH. That is, at least one of the organic acid and / or phosphoric acid contained in the patent has an acid dissociation constant close to the acid dissociation constant of thioglycolic acid, and most of the thioglycolic acid is dissociated or neutralized. It is not necessary to be present in the acid state, which is a necessary condition for providing the effect of the patent.
毛髪の傷みと弾力の低下の少ない縮毛矯正方法及び毛髪処理剤として、特許文献３には、（ｉ）還元剤、アルカリ剤及び水を含む第１の薬剤を毛髪に塗布する工程、（ｉ−２）前記毛髪を洗浄し、その後に、前記毛髪を乾燥する工程、（ｉ−３）ボイラー部及びハンドピース部を備える噴霧器の、前記ボイラー部で水を沸騰させて水蒸気を生成し、前記水蒸気を１３０℃以上３気圧以上で加熱する工程、（ｉ−４）前記ハンドピース部で前記水蒸気を２００℃以上に再加熱することにより０．２６〜１ｎｍの粒径を有し、かつ２００〜２３０℃の温度を有する過熱水蒸気を得る工程、（ｉｉ）前記工程（ｉ−４）の後に、前記過熱水蒸気を前記毛髪に向けて噴霧する工程、及び（ｉｉｉ）前記噴霧の直後に又は前記噴霧を行いながら、前記毛髪に１６０〜１７０℃の温度をかけて前記毛髪を伸ばす工程を含む毛髪にストレートパーマをかける方法が開示されている。この方法では、より毛髪の傷みが少なく、毛髪の艶がより改善されるが、毛髪の弾力の低下を十分に解消することができず、さらに手間と時間、及び／又は過熱水蒸気を得る専用の装置が必要になり、実益に乏しいのが現状である。 As a hair straightening method and a hair treatment agent with less damage to the hair and a decrease in elasticity, Patent Document 3 describes (i) a step of applying a first agent containing a reducing agent, an alkaline agent and water to the hair, (i). -2) The step of washing the hair and then drying the hair, (i-3) boiling water in the boiler part of a sprayer provided with a boiler part and a handpiece part to generate steam, and the above. Step of heating steam at 130 ° C. or higher and 3 atm or higher, (i-4) By reheating the steam to 200 ° C. or higher in the handpiece portion, the steam has a particle size of 0.26 to 1 nm and 200 to 200. A step of obtaining superheated steam having a temperature of 230 ° C., (ii) a step of spraying the superheated steam toward the hair after the step (i-4), and (iii) immediately after the spray or the spray. Disclosed is a method of applying a straight perm to the hair, which comprises a step of applying a temperature of 160 to 170 ° C. to the hair to straighten the hair. This method causes less damage to the hair and improves the gloss of the hair, but it cannot sufficiently eliminate the decrease in the elasticity of the hair, and it is dedicated to obtaining labor, time, and / or superheated steam. The current situation is that equipment is required and the actual profit is poor.
本発明は、前記従来技術の欠点に鑑みてなされたものであり、毛髪の傷みと弾力の低下を十分に抑制し、かつ、良好な縮毛矯正効果を有する毛髪処理剤を提供することを目的とする。 The present invention has been made in view of the above-mentioned drawbacks of the prior art, and an object of the present invention is to provide a hair treatment agent which sufficiently suppresses hair damage and decrease in elasticity and has a good hair straightening effect. And.
本発明者は、前記の課題を解決すべく鋭意研究を重ねた結果、対イオンを有しないレブリン酸と、還元成分とを含有し、かつｐＨが４．０〜５．５の範囲に調整するにより、毛髪の傷みと弾力の低下を十分に抑制し、かつ、良好な縮毛矯正効果を実現できることを見出し、本発明を完成するに至った。 As a result of diligent research to solve the above-mentioned problems, the present inventor adjusts the pH to a range of 4.0 to 5.5, which contains levulinic acid having no counterion and a reducing component. As a result, it has been found that damage to hair and a decrease in elasticity can be sufficiently suppressed and a good hair straightening effect can be realized, and the present invention has been completed.
すなわち、本発明の毛髪処理剤は、
（ａ）対イオンを有しないレブリン酸を２〜２０質量％と、
（ｂ）還元成分を２〜１１質量％と、
を含有し、かつｐＨが４．０〜５．５の範囲であることを特徴とする。That is, the hair treatment agent of the present invention is
(A) Levulinic acid having no counterion is 2 to 20% by mass,
(B) The reducing component is 2 to 11% by mass,
The pH is in the range of 4.0 to 5.5.
本発明の毛髪処理剤により、髪の傷みと弾力の低下を十分に抑制し、かつ、良好な縮毛矯正効果が可能となる。 The hair treatment agent of the present invention sufficiently suppresses damage to hair and a decrease in elasticity, and enables a good hair straightening effect.
＜毛髪処理剤＞
本発明の毛髪処理剤は、対イオンを有しないレブリン酸と還元成分とを必須に含有する。以下、本発明について詳述する。<Hair treatment agent>
The hair treatment agent of the present invention indispensably contains levulinic acid having no counterion and a reducing component. Hereinafter, the present invention will be described in detail.
対イオンを有しないレブリン酸の含有量は、本発明の毛髪処理剤の全量に対して、２〜２０質量％、好ましくは７．５〜１５質量％である。含有量が２質量％未満では十分な毛髪の傷みと弾力の低下を抑制する効果を得ることができず、一方、２０質量％を超えて含有しても、含有量に見合った毛髪の傷みと弾力の低下を抑制する効果の向上は期待できない。 The content of levulinic acid having no counterion is 2 to 20% by mass, preferably 7.5 to 15% by mass, based on the total amount of the hair treatment agent of the present invention. If the content is less than 2% by mass, sufficient hair damage and the effect of suppressing the decrease in elasticity cannot be obtained, while even if the content exceeds 20% by mass, the hair damage is commensurate with the content. No improvement in the effect of suppressing the decrease in elasticity can be expected.
還元成分の含有量は、本発明の毛髪処理剤の全量に対して、２〜１１質量％、好ましくは５〜７質量％である。含有量が２質量％未満では十分な縮毛矯正効果を得ることができず、一方、１１質量％を超えて含有すると、毛髪の傷みと弾力の低下が発生してしまう。 The content of the reducing component is 2 to 11% by mass, preferably 5 to 7% by mass, based on the total amount of the hair treatment agent of the present invention. If the content is less than 2% by mass, a sufficient hair straightening effect cannot be obtained, while if the content exceeds 11% by mass, the hair is damaged and the elasticity is reduced.
前記還元成分としては、チオール基を有していてかつ、酸解離定数がレブリン酸より小さい値を有している又は、チオール基を有していてかつ、酸解離定数を有しない種々の公知のものを使用することができる。チオール基を有していてかつ、酸解離定数がレブリン酸より小さい値を有している還元成分では、レブリン酸は、対イオンを有することなく、その効果を発揮することができる。また、酸を対イオンとして有する還元剤に用いられる酸はレブリン酸より小さい酸解離定数を有する必要がある。これにより、レブリン酸は、対イオンを有することなく、その効果を発揮することができる。チオール基を有していてかつ、酸解離定数がレブリン酸より小さい値を有している還元成分として例えば、チオグリコール酸又はその塩、チオ乳酸又はその塩、システイン又はその塩等が挙げられる。また、チオール基を有していてかつ、酸解離定数を有しない還元成分として例えば、システアミン又はその塩、チオグリセリン等が挙げられる。チオール基を有していてかつ、酸解離定数がレブリン酸より小さい値を有している還元成分及び、チオール基を有していてかつ、酸解離定数を有しない還元成分より選択される１種を単独で又は２種以上を組み合わせて用いることができる。 As the reducing component, various known substances having a thiol group and having an acid dissociation constant smaller than that of levulinic acid, or having a thiol group and having no acid dissociation constant. You can use things. In the reducing component having a thiol group and having an acid dissociation constant smaller than that of levulinic acid, levulinic acid can exert its effect without having a counterion. Further, the acid used for the reducing agent having an acid as a counterion needs to have an acid dissociation constant smaller than that of levulinic acid. Thereby, levulinic acid can exert its effect without having a counterion. Examples of the reducing component having a thiol group and having an acid dissociation constant smaller than that of levulinic acid include thioglycolic acid or a salt thereof, thiolactic acid or a salt thereof, cysteine or a salt thereof and the like. Further, examples of the reducing component having a thiol group and not having an acid dissociation constant include cysteamine or a salt thereof, thioglycerin and the like. One selected from a reducing component having a thiol group and having an acid dissociation constant smaller than that of levulinic acid, and a reducing component having a thiol group and having no acid dissociation constant. Can be used alone or in combination of two or more.
本発明の毛髪処理剤は、ｐＨを４．０〜５．５の範囲、好ましくは４．５〜５．５の範囲に保持することが必要である。ｐＨが４．０未満では、十分な縮毛矯正効果を得ることができず、ｐＨが５．５を超えると、毛髪の傷みと弾力の低下が発生してしまう。即ち、毛髪の等電点付近であることが必要である。
毛髪処理剤のｐＨを前記範囲に調整するための対イオンを有しない塩基としては、特に限定されるものではないが、水酸化ナトリウムや水酸化カリウム等の無機塩基、アンモニア水やトリエタノールアミン、塩基性アミノ酸等の有機塩基を用いることができる。又、対イオンを有する塩基としては、対イオンを有する塩基に用いられるレブリン酸以外の酸は、レブリン酸より小さい酸解離定数を有する必要がある。これにより、レブリン酸は、対イオンを有することなく、その効果を発揮することができる。例えば、グリコール酸や乳酸等のモノカルボン酸のナトリウム塩等である対イオンを有する塩基、マレイン酸やリンゴ酸等のジカルボン酸のナトリウム塩等である対イオンを有する塩基、クエン酸等のトリカルボン酸のナトリウム塩等である対イオンを有する塩基、グルタミン酸やアスパラギン酸である酸性アミノ酸のナトリウム塩等である対イオンを有する塩基、リン酸やポリリン酸等の無機酸のナトリウム塩等である対イオンを有する塩基、エチドロン酸、エデト酸、フィチン酸等のキレート効果を特に有する酸のナトリウム塩等である対イオンを有する塩基、等を用いることができる。これらは、１種を単独で又は２種以上を組み合わせて用いることができる。
毛髪処理剤のｐＨを前記範囲に調整するための酸としては、レブリン酸より小さい酸解離定数を有する酸であれば、特に限定されるものではない。The hair treatment agent of the present invention needs to keep the pH in the range of 4.0 to 5.5, preferably in the range of 4.5 to 5.5. If the pH is less than 4.0, a sufficient hair straightening effect cannot be obtained, and if the pH exceeds 5.5, hair damage and a decrease in elasticity will occur. That is, it is necessary to be near the isoelectric point of the hair.
The base having no counterion for adjusting the pH of the hair treatment agent to the above range is not particularly limited, but is not particularly limited, but is an inorganic base such as sodium hydroxide or potassium hydroxide, aqueous ammonia or triethanolamine, and the like. Organic bases such as basic amino acids can be used. Further, as the base having a counterion, an acid other than levulinic acid used for the base having a counterion needs to have an acid dissociation constant smaller than that of levulinic acid. Thereby, levulinic acid can exert its effect without having a counterion. For example, a base having a counterion such as a sodium salt of a monocarboxylic acid such as glycolic acid or lactic acid, a base having a counterion such as a sodium salt of a dicarboxylic acid such as maleic acid or malic acid, or a tricarboxylic acid such as citric acid. A base having a pair ion such as a sodium salt of, a base having a pair ion such as a sodium salt of an acidic amino acid such as glutamic acid or aspartic acid, and a counter ion such as a sodium salt of an inorganic acid such as phosphoric acid or polyphosphoric acid. A base having a counter ion, such as a sodium salt of an acid having a particularly chelating effect such as a base having a ethidronic acid, an edetonic acid, or a phytic acid, can be used. These can be used alone or in combination of two or more.
The acid for adjusting the pH of the hair treatment agent to the above range is not particularly limited as long as it has an acid dissociation constant smaller than that of levulinic acid.
前記毛髪処理剤には、レブリン酸と還元成分以外にも、通常化粧品や医薬部外品等に用いられる他の成分を、本発明の効果を損なわない範囲内で任意に添加することができる。このような成分として、例えばカチオン性高分子、アニオン性高分子、非イオン高分子、両性高分子、多価アルコール、糖類、アミノ酸、ペプチド、プロテイン、金属イオン封鎖剤、油分、粉末成分、カチオン界面活性剤、アニオン界面活性剤、非イオン界面活性剤、両性界面活性剤、増粘剤、粉末成分、香料、粉末成分、色素、水等を含有することができる。 In addition to levulinic acid and reducing components, other components usually used for cosmetics, quasi-drugs, and the like can be arbitrarily added to the hair treatment agent as long as the effects of the present invention are not impaired. Such components include, for example, cationic polymers, anionic polymers, nonionic polymers, amphoteric polymers, polyhydric alcohols, saccharides, amino acids, peptides, proteins, metal ion blockers, oils, powder components, cationic surfactants. It can contain an active agent, an anionic surfactant, a nonionic surfactant, an amphoteric surfactant, a thickener, a powder component, a fragrance, a powder component, a pigment, water and the like.
本発明にかかる毛髪処理剤の剤型は、所望の効果が充分に発揮されるのであれば特に限定されないが、例えば、液状、乳液状、ゲル状、フォーム状、クリーム状などの剤型を採りうる。 The dosage form of the hair treatment agent according to the present invention is not particularly limited as long as the desired effect is sufficiently exhibited, and for example, a liquid, milky liquid, gel-like, foam-like, cream-like or other dosage form is adopted. sell.
以下に具体例を挙げて本発明を更に詳細に説明するが、本発明は以下の実施例に限定されるものではない。また、以下の実施例等における配合量は特に断らない限り質量％を示す。 The present invention will be described in more detail below with reference to specific examples, but the present invention is not limited to the following examples. In addition, the blending amount in the following examples and the like indicates mass% unless otherwise specified.
（実施例１〜８及び比較例１〜２）
下記の表１に掲げた組成を有する毛髪処理剤を、精製水に各成分を均一になるまで撹拌混合することにより調製した。
得られた毛髪処理剤の毛髪の傷みと弾力の低下抑制効果及び縮毛矯正効果の評価を、下記の方法により評価した。(Examples 1 to 8 and Comparative Examples 1 to 2)
A hair treatment agent having the composition shown in Table 1 below was prepared by stirring and mixing each component in purified water until the components became uniform.
The evaluation of the hair damage and elasticity reduction suppressing effect and the curly hair straightening effect of the obtained hair treatment agent was evaluated by the following method.
また、臭素酸ナトリウムの７質量％水溶液を調整し、第２剤とする。 Further, a 7% by mass aqueous solution of sodium bromate is prepared and used as a second agent.
＜試験毛束の作成＞
天然クセ毛（インド人黒毛）を伸長時の長さが３０ｃｍになるように切りそろえ、重さ３ｇの毛束を作成した。ついで、各毛束を市販の８レベルの酸化染毛剤にて処理し、市販のシャンプーにて２回洗浄し、十分にタオルドライし、毛束の一端を固定して垂直方向に吊し、２４時間室温放置する。その後、再度、各毛束を市販の８レベルの酸化染毛剤にて処理し、市販のシャンプーにて２回洗浄し、十分にタオルドライし試験毛束とした。<Creation of test hair bundle>
Natural peculiar hair (Indian black hair) was cut so that the length at the time of extension was 30 cm, and a hair bundle weighing 3 g was created. Then, each hair bundle was treated with a commercially available 8-level oxidative hair dye, washed twice with a commercially available shampoo, thoroughly towel-dried, and one end of the hair bundle was fixed and hung vertically. Leave at room temperature for 24 hours. Then, each hair bundle was treated again with a commercially available 8-level oxidative hair dye, washed twice with a commercially available shampoo, and sufficiently towel-dried to obtain a test hair bundle.
＜毛髪の傷みと弾力の低下抑制効果の評価＞
試験毛束に調整した毛髪処理剤を３ｇ塗布し、４０℃で２０分間放置する。その後、お湯で十分に毛髪処理剤を洗い流す。十分にタオルドライしてからドライヤーで乾燥させ、１９０℃に熱した毛髪矯正アイロンにて１０秒間かけて毛髪をストレート状にした。次に、前記第２剤を５ｇ塗布し、室温にて１５分間放置し、お湯で十分に第２剤を洗い流す。十分にタオルドライし、この毛束の一端を固定して垂直方向に吊し、２４時間室温放置する。その後、６０℃の２％ポリオキシエチレンラウリル硫酸Ｎａ水溶液に１時間浸漬し、十分にお湯で洗い流した後、十分にタオルドライし、この毛束の一端を固定して垂直方向に吊し、２４時間室温放置して十分に乾燥した時に、下記の評価基準により、１０年以上の美容師経験を有する３名が評価した。
＜評価基準＞
毛髪の傷みは、毛髪の手触りで評価する。毛髪の傷みと弾力の低下は、毛束の一端を固定して垂直方向に吊し、２４時間室温放置して十分に乾燥した試験毛束との比較にて評価する。
１．ゴワツキがあり手触りが悪い。弾力がやや弱い〜弱い。
２．ゴワツキがややあり手触りがやや悪い。弾力はやや弱い。
３．ゴワツキがない。弾力はキープしている。
４．しなやかさがあり手触りがよい。弾力はキープしている。
５．しなやかさがあり手触りがとてもよい。弾力はキープしている。<Evaluation of hair damage and elasticity suppression effect>
Apply 3 g of the adjusted hair treatment agent to the test hair bundle and leave it at 40 ° C. for 20 minutes. After that, wash off the hair treatment agent thoroughly with hot water. The hair was sufficiently towel-dried, dried with a dryer, and straightened with a hair straightening iron heated to 190 ° C. for 10 seconds. Next, 5 g of the second agent is applied, left at room temperature for 15 minutes, and the second agent is thoroughly washed away with hot water. Thoroughly towel dry, fix one end of this hair bundle, hang it vertically, and leave it at room temperature for 24 hours. Then, it was immersed in a 2% aqueous solution of sodium polyoxyethylene lauryl sulfate at 60 ° C. for 1 hour, rinsed thoroughly with hot water, thoroughly towel-dried, and one end of this hair bundle was fixed and hung vertically. When it was left at room temperature for a long time and dried sufficiently, it was evaluated by three people who had more than 10 years of experience as a beautician according to the following evaluation criteria.
<Evaluation criteria>
Hair damage is assessed by the feel of the hair. Hair damage and loss of elasticity are evaluated by comparison with a sufficiently dry test hair bundle in which one end of the hair bundle is fixed and hung vertically and left at room temperature for 24 hours.
1. 1. It is stiff and feels bad. Elasticity is a little weak to weak.
2. 2. There is a little ruggedness and the texture is a little bad. The elasticity is a little weak.
3. 3. There is no stiffness. The elasticity is kept.
4. It is supple and feels good. The elasticity is kept.
5. It is supple and feels very good. The elasticity is kept.
＜縮毛矯正効果の評価＞
試験毛束に調整した毛髪処理剤を３ｇ塗布し、４０℃で２０分間放置する。その後、お湯で十分に毛髪処理剤を洗い流す。十分にタオルドライしてからドライヤーで乾燥させ、１９０℃に熱した毛髪矯正アイロンにて１０秒間かけて毛髪をストレート状にした。次に、前記第２剤を５ｇ塗布し、室温にて１５分間放置し、お湯で十分に第２剤を洗い流す。十分にタオルドライし、この毛束の一端を固定して垂直方向に吊し、２４時間室温放置した後、市販のシャンプーにて１回洗浄し、十分にタオルドライし、この毛束の一端を固定して垂直方向に吊し、２４時間室温放置してして十分に乾燥した時に、下記の評価基準により、１０年以上の美容師経験を有する３名が評価した。
＜評価基準＞
１．クセが残っており、まとまりが悪い。
２．クセは少し残っており、まとまりがやや悪い。
３．クセがわずかに残っているが、まとまりがある。
４．クセがほぼ伸びていて、まとまりが良い。
５．クセが伸びていて、ツヤとまとまりが良い。<Evaluation of hair straightening effect>
Apply 3 g of the adjusted hair treatment agent to the test hair bundle and leave it at 40 ° C. for 20 minutes. After that, wash off the hair treatment agent thoroughly with hot water. The hair was sufficiently towel-dried, dried with a dryer, and straightened with a hair straightening iron heated to 190 ° C. for 10 seconds. Next, 5 g of the second agent is applied, left at room temperature for 15 minutes, and the second agent is thoroughly washed away with hot water. Thoroughly towel dry, fix one end of this hair bundle and hang it vertically, leave it at room temperature for 24 hours, wash it once with a commercially available shampoo, thoroughly towel dry it, and then towel dry one end of this hair bundle. When it was fixed, hung vertically, left at room temperature for 24 hours and sufficiently dried, it was evaluated by three people with more than 10 years of experience as a beautician according to the following evaluation criteria.
<Evaluation criteria>
1. 1. There is a habit left, and it is not well organized.
2. 2. There is a little habit left, and the cohesion is a little bad.
3. 3. There is a slight habit, but it is cohesive.
4. The habit is almost stretched and the cohesiveness is good.
5. It has a long habit and is glossy and cohesive.
実施例１〜８に示されるように、対イオンを有しないレブリン酸を２〜２０質量％を含有した場合に、十分な毛髪の傷みと弾力の低下抑制効果及び、縮毛矯正効果が得られた。これに対し、比較例１〜２に示されるように、対イオンを有しないレブリン酸の配合量が前記範囲未満である場合には、十分な毛髪の傷みと弾力の低下抑制効果が不十分であった。 As shown in Examples 1 to 8, when levulinic acid having no counterion is contained in an amount of 2 to 20% by mass, sufficient hair damage, an effect of suppressing a decrease in elasticity, and an effect of straightening curly hair can be obtained. rice field. On the other hand, as shown in Comparative Examples 1 and 2, when the blending amount of levulinic acid having no counterion is less than the above range, sufficient hair damage and the effect of suppressing the decrease in elasticity are insufficient. there were.
（実施例９〜１６及び比較例３〜７）
下記の表２に掲げた組成を有する毛髪処理剤を、精製水に各成分を均一になるまで撹拌混合することにより調製した。
得られた毛髪処理剤の毛髪の傷みと弾力の低下抑制効果及び縮毛矯正効果の評価を前記の方法により評価した。(Examples 9 to 16 and Comparative Examples 3 to 7)
A hair treatment agent having the composition shown in Table 2 below was prepared by stirring and mixing each component in purified water until the components became uniform.
The evaluation of the hair damage and elasticity reduction suppressing effect and the hair straightening effect of the obtained hair treatment agent was evaluated by the above method.
実施例９〜１６に示されるように、還元剤を２〜１１質量％を含有した場合に、十分な毛髪の傷みと弾力の低下抑制効果及び、縮毛矯正効果が得られた。これに対し、比較例３〜７に示されるように、還元剤の配合量が前記範囲外である場合には、毛髪の傷みと弾力の低下抑制効果又は、縮毛矯正効果が不十分であった。 As shown in Examples 9 to 16, when the reducing agent was contained in an amount of 2 to 11% by mass, sufficient hair damage, an effect of suppressing a decrease in elasticity, and an effect of straightening curly hair were obtained. On the other hand, as shown in Comparative Examples 3 to 7, when the blending amount of the reducing agent is out of the above range, the effect of suppressing hair damage and decrease in elasticity or the effect of straightening curly hair is insufficient. rice field.
（実施例１７〜２４及び比較例８〜１５）
下記の表３に掲げた組成を有する毛髪処理剤を、精製水に各成分を均一になるまで撹拌混合することにより調製した。
得られた毛髪処理剤の毛髪の傷みと弾力の低下抑制効果及び縮毛矯正効果の評価を前記の方法により評価した。(Examples 17 to 24 and Comparative Examples 8 to 15)
A hair treatment agent having the composition shown in Table 3 below was prepared by stirring and mixing each component in purified water until the components became uniform.
The evaluation of the hair damage and elasticity reduction suppressing effect and the hair straightening effect of the obtained hair treatment agent was evaluated by the above method.
実施例１７〜２４に示されるように、ｐＨが４．０〜５．５の場合に、十分な毛髪の傷みと弾力の低下抑制効果及び、縮毛矯正効果が得られた。これに対し、比較例８〜１７に示されるように、ｐＨが前記範囲外である場合には、毛髪の傷みと弾力の低下抑制効果又は、縮毛矯正効果が不十分であった。 As shown in Examples 17 to 24, when the pH was 4.0 to 5.5, sufficient hair damage, an effect of suppressing a decrease in elasticity, and an effect of straightening curly hair were obtained. On the other hand, as shown in Comparative Examples 8 to 17, when the pH was out of the above range, the effect of suppressing hair damage and decrease in elasticity or the effect of straightening curly hair was insufficient.
Claims (1)
（ｂ）還元成分を２〜１１質量％と、
を含有し、かつｐＨが４．０〜５．５の範囲であることを特徴とする毛髪処理剤。(A) Levulinic acid having no counterion is 2 to 20% by mass,
(B) The reducing component is 2 to 11% by mass,
A hair treatment agent containing, and having a pH in the range of 4.0 to 5.5.
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| JPH08268849A (en) * | 1996-05-02 | 1996-10-15 | Shiseido Co Ltd | Acidic hair-dyeing agent composition for head hair |
| JP2007176826A (en) * | 2005-12-27 | 2007-07-12 | Lion Corp | Hair cosmetic |
| JP2013053113A (en) * | 2011-09-06 | 2013-03-21 | Nippon Fine Chem Co Ltd | Hair improvement method based on lactone compound |
| JP2019123701A (en) * | 2018-01-12 | 2019-07-25 | 株式会社イングラボ | Hair treatment agent |
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| JP2020070282A (en) | 2018-10-31 | 2020-05-07 | 株式会社Ｃｕｔｉｃｕｌａ | Hair treatment agent and permanent wave treatment method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JPS4840945A (en) * | 1971-10-07 | 1973-06-15 | Otsuka Chemical Co Ltd | |
| JPH08268849A (en) * | 1996-05-02 | 1996-10-15 | Shiseido Co Ltd | Acidic hair-dyeing agent composition for head hair |
| JP2007176826A (en) * | 2005-12-27 | 2007-07-12 | Lion Corp | Hair cosmetic |
| JP2013053113A (en) * | 2011-09-06 | 2013-03-21 | Nippon Fine Chem Co Ltd | Hair improvement method based on lactone compound |
| JP2019123701A (en) * | 2018-01-12 | 2019-07-25 | 株式会社イングラボ | Hair treatment agent |
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| JP2023074728A (en) * | 2021-11-18 | 2023-05-30 | 京楽産業．株式会社 | game machine |
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