JPH0611690B2 - Resin composition for fixing hair coloring agent and hair coloring agent using the same - Google Patents
Resin composition for fixing hair coloring agent and hair coloring agent using the sameInfo
- Publication number
- JPH0611690B2 JPH0611690B2 JP4024588A JP4024588A JPH0611690B2 JP H0611690 B2 JPH0611690 B2 JP H0611690B2 JP 4024588 A JP4024588 A JP 4024588A JP 4024588 A JP4024588 A JP 4024588A JP H0611690 B2 JPH0611690 B2 JP H0611690B2
- Authority
- JP
- Japan
- Prior art keywords
- coloring agent
- hair
- weight
- hair coloring
- resin composition
- 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.)
- Expired - Fee Related
Links
- 239000003086 colorant Substances 0.000 title claims description 24
- 230000037308 hair color Effects 0.000 title claims description 17
- 239000011342 resin composition Substances 0.000 title claims description 14
- 239000000178 monomer Substances 0.000 claims description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 7
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 7
- -1 aliphatic alcohols Chemical class 0.000 claims description 7
- 239000000126 substance Substances 0.000 claims description 7
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 5
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 5
- 125000005397 methacrylic acid ester group Chemical group 0.000 claims description 4
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 claims description 3
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 3
- 125000004432 carbon atom Chemical group C* 0.000 claims description 3
- 150000002148 esters Chemical class 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 claims description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 3
- 229920002554 vinyl polymer Polymers 0.000 claims description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 2
- 230000003472 neutralizing effect Effects 0.000 claims 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 25
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 14
- 235000019441 ethanol Nutrition 0.000 description 12
- 239000000203 mixture Substances 0.000 description 10
- 239000011347 resin Substances 0.000 description 9
- 229920005989 resin Polymers 0.000 description 9
- 239000002904 solvent Substances 0.000 description 7
- 229920001577 copolymer Polymers 0.000 description 6
- 239000007921 spray Substances 0.000 description 6
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 238000002360 preparation method Methods 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- 238000004040 coloring Methods 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000003505 polymerization initiator Substances 0.000 description 4
- 238000006116 polymerization reaction Methods 0.000 description 4
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 3
- 238000007334 copolymerization reaction Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- 239000007789 gas Substances 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 2
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 2
- VHUUQVKOLVNVRT-UHFFFAOYSA-N Ammonium hydroxide Chemical compound [NH4+].[OH-] VHUUQVKOLVNVRT-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 238000005299 abrasion Methods 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N ammonia Natural products N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- RJUVPCYAOBNZAX-VOTSOKGWSA-N ethyl (e)-3-(dimethylamino)-2-methylprop-2-enoate Chemical compound CCOC(=O)C(\C)=C\N(C)C RJUVPCYAOBNZAX-VOTSOKGWSA-N 0.000 description 2
- 239000000118 hair dye Substances 0.000 description 2
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 2
- 238000010992 reflux Methods 0.000 description 2
- 229920003067 (meth)acrylic acid ester copolymer Polymers 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- HXKKHQJGJAFBHI-UHFFFAOYSA-N 1-aminopropan-2-ol Chemical compound CC(O)CN HXKKHQJGJAFBHI-UHFFFAOYSA-N 0.000 description 1
- SDXHBDVTZNMBEW-UHFFFAOYSA-N 1-ethoxy-2-(2-hydroxyethoxy)ethanol Chemical compound CCOC(O)COCCO SDXHBDVTZNMBEW-UHFFFAOYSA-N 0.000 description 1
- VTETWVVUUXJHMT-UHFFFAOYSA-N 1-ethoxy-2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethanol Chemical compound CCOC(O)COCCOCCOCCO VTETWVVUUXJHMT-UHFFFAOYSA-N 0.000 description 1
- YHYCMHWTYHPIQS-UHFFFAOYSA-N 2-(2-hydroxyethoxy)-1-methoxyethanol Chemical compound COC(O)COCCO YHYCMHWTYHPIQS-UHFFFAOYSA-N 0.000 description 1
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 1
- XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
- IOAOAKDONABGPZ-UHFFFAOYSA-N 2-amino-2-ethylpropane-1,3-diol Chemical compound CCC(N)(CO)CO IOAOAKDONABGPZ-UHFFFAOYSA-N 0.000 description 1
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 1
- ZNQVEEAIQZEUHB-UHFFFAOYSA-N 2-ethoxyethanol Chemical compound CCOCCO ZNQVEEAIQZEUHB-UHFFFAOYSA-N 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 206010016322 Feeling abnormal Diseases 0.000 description 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 description 1
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-M chloroacetate Chemical group [O-]C(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-M 0.000 description 1
- FOCAUTSVDIKZOP-UHFFFAOYSA-N chloroacetic acid Chemical class OC(=O)CCl FOCAUTSVDIKZOP-UHFFFAOYSA-N 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- SWXVUIWOUIDPGS-UHFFFAOYSA-N diacetone alcohol Chemical compound CC(=O)CC(C)(C)O SWXVUIWOUIDPGS-UHFFFAOYSA-N 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- LVTYICIALWPMFW-UHFFFAOYSA-N diisopropanolamine Chemical compound CC(O)CNCC(C)O LVTYICIALWPMFW-UHFFFAOYSA-N 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000005448 ethoxyethyl group Chemical group [H]C([H])([H])C([H])([H])OC([H])([H])C([H])([H])* 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 238000005562 fading Methods 0.000 description 1
- 238000010528 free radical solution polymerization reaction Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- 125000000959 isobutyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 238000006386 neutralization reaction Methods 0.000 description 1
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 230000002265 prevention Effects 0.000 description 1
- 239000003380 propellant Substances 0.000 description 1
- 239000008213 purified water Substances 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
Classifications
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q5/00—Preparations for care of the hair
- A61Q5/004—Preparations used to protect coloured hair
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
- A61K8/8141—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides or nitriles thereof; Compositions of derivatives of such polymers
- A61K8/8152—Homopolymers or copolymers of esters, e.g. (meth)acrylic acid esters; Compositions of derivatives of such polymers
Landscapes
- Life Sciences & Earth Sciences (AREA)
- Health & Medical Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Description
【発明の詳細な説明】 〔産業上の利用分野〕 本発明は、頭髪着色料固着用樹脂組成物、特に頭髪を一
時的に着色するために顔料等の頭髪着色料を固着させる
樹脂組成物及びそれを用いた頭髪着色剤に関する。DETAILED DESCRIPTION OF THE INVENTION [Industrial field of application] The present invention relates to a resin composition for fixing a hair colorant, particularly a resin composition for fixing a hair colorant such as a pigment for temporarily coloring hair. A hair coloring agent using the same.
頭髪を一時的に着色するために頭髪着色料とその固着用
樹脂を混合してなる白髪の着色剤やマスカラタイプ、カ
ラースプレー、カラフォーム等からなる頭髪化粧用着色
剤が知られている。マスカラタイプ、カラースプレー、
カラフォームはエタノールや水等を溶媒としたものであ
り、またカラースプレー、カラフォームはフロンガス等
の噴射剤と共に耐圧エアゾール容器に充填されている。BACKGROUND ART There are known white hair colorants prepared by mixing a hair colorant and a fixing resin for temporary coloring of hair, and hair colorants such as mascara type, color spray, and color foam. Mascara type, color spray,
Colorfoam uses ethanol or water as a solvent, and color spray and colorfoam are filled in a pressure resistant aerosol container together with a propellant such as Freon gas.
上記の頭髪着色料固着用樹脂として、ビニルピロリドン
−酢酸ビニル共重合体、Ｎ，Ｎ′−ジメチルアミノエチ
ルメタクリレートのモノクロル酢酸塩変性物とメタクリ
ル酸エステルの共重合体、アクリル酸エステル−メタク
リル酸エステル共重合体等が知られている。As the above-mentioned resin for fixing the hair coloring agent, a vinylpyrrolidone-vinyl acetate copolymer, a monochloroacetic acid salt modified product of N, N'-dimethylaminoethyl methacrylate and a methacrylic acid ester copolymer, an acrylic acid ester-methacrylic acid ester Copolymers and the like are known.
しかし、上記ビニルピロリドン−酢酸ビニル共重合体で
は、形成フィルムが吸湿前には硬く、また吸湿すると急
に柔軟になり、べたつきが生じる等の問題があった。ま
た、Ｎ，Ｎ′−ジメチルアミノエチルメタクリレートの
モノクロル酢酸塩変性物とメタクリル酸エステルの共重
合体についても吸湿性が大きく、湿潤時の色落ちが多く
なる等の問題があった。さらに、アクリル酸エステル−
メタクリル酸エステル共重合体では、一般的なセット剤
の場合、形成フィルムが硬く、フレーキング防止も不十
分であり、ソフト感がなく、洗髪性が悪い等の問題があ
った。However, in the above-mentioned vinylpyrrolidone-vinyl acetate copolymer, there is a problem that the formed film is hard before absorbing moisture, and when absorbing moisture, it suddenly becomes flexible and sticky. Further, a copolymer of N, N'-dimethylaminoethyl methacrylate modified with monochloroacetate and a methacrylic acid ester also has a problem that the hygroscopicity is large and the color fading when wet is increased. Furthermore, acrylic acid ester-
In the case of a general setting agent, the methacrylic acid ester copolymer has problems that the formed film is hard, flaking prevention is insufficient, there is no soft feeling, and the hair washability is poor.
従って、本発明の目的は、毛髪への密着性がよく、形成
フィルムが柔軟であり、耐水性を有し、摩擦による色落
ちがなく、洗髪性の良好な頭髪着色料固着用樹脂組成物
及びそれを用いた頭髪着色剤を提供することにある。Therefore, an object of the present invention is to provide a resin composition for fixing a hair colorant, which has good adhesion to hair, a formed film is flexible, has water resistance, does not lose color due to friction, and has good hair washability. It is to provide a hair coloring agent using the same.
本発明に係る頭髪着色料固着用樹脂組成物は、下記の重
合性単量体ａ〜ｄ、即ち、 ａ．次式で示されるアクリル酸エステル及び／又はメタ
クリル酸エステルからなる少なくとも１種の単量体
３０〜７０重量％ （式中、Ｒ1は水素原子又はメチル基、Ｒ2はメチル基又
はエチル基、ｎは１〜１０の整数である。） ｂ．アクリル酸、メタクリル酸及びイタコン酸からなる
群より選ばれた少なくとも１種の単量体 ５〜
２５重量％ ｃ．アクリル酸及び／又はメタクリル酸の炭素数８〜１
８の脂肪族アルコールのエステルからなる少なくとも１
種の単量体 ５〜２０重量％ ｄ．その他のビニル系単量体 ２０〜５０重量
％ を共重合し、水溶性有機塩基性物質で中和してなるもの
であり、また本発明に係る頭髪着色剤は上記の頭髪着色
料固着用樹脂組成物を頭髪着色料等と共に含むものであ
る。The hair colorant fixing resin composition according to the present invention has the following polymerizable monomers a to d, that is, a. At least one monomer consisting of acrylic acid ester and / or methacrylic acid ester represented by the following formula
30-70% by weight (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is a methyl group or an ethyl group, and n is an integer of 1 to 10.) b. At least one monomer selected from the group consisting of acrylic acid, methacrylic acid, and itaconic acid;
25% by weight c. Acrylic acid and / or methacrylic acid having 8 to 1 carbon atoms
At least 1 consisting of an ester of 8 aliphatic alcohols
Seed monomer 5-20% by weight d. Other vinyl-based monomer 20 to 50% by weight is copolymerized and neutralized with a water-soluble organic basic substance, and the hair coloring agent according to the present invention is the above-mentioned resin for fixing hair coloring agent. The composition includes a hair coloring agent and the like.
上記単量体ａは、樹脂の髪への密着性及び光沢を向上さ
せ、親水性、洗髪性等を調整するものであり、その使用
料は、全重合性単量体に対して３０〜７０重量％、好ま
しくは３５〜６０重量％である。上記使用量が３０重量
％に満たないと、毛髪への密着不良や光沢不良等を生じ
ると共に洗髪性も低下し、一方、それが７０重量％を超
えると、親水性が過剰になると共に耐水性が低下する。The monomer a improves adhesion of the resin to hair and gloss, and adjusts hydrophilicity, hair washability, and the like, and the use amount thereof is 30 to 70 with respect to all polymerizable monomers. %, Preferably 35-60% by weight. If the amount used is less than 30% by weight, poor adhesion to hair, poor gloss, and the like, and poor hair washability, while if it exceeds 70% by weight, the hydrophilicity becomes excessive and the water resistance is high. Is reduced.
単量体ａの具体例として、例えば、メトキシエチル（メ
タ）アクリレート、メトキシジエチレングリコール（メ
タ）アクリレート、メトキシテトラエチレン（メタ）ア
クリレート、メトキシポリエチレングリコール＃４００
（メタ）アクリレート、エトキシエチル（メタ）アクリ
レート、エトキシジエチレングリコール（メタ）アクリ
レート、エトキシテトラエチレングリコール（メタ）ア
クリレート、エトキシポリエチレングリコール＃４００
（メタ）アクリレート等をあげることができ、それらの
アクリル酸エステル、メタクリル酸エステルを単独又は
併用で使用することができる。Specific examples of the monomer a include, for example, methoxyethyl (meth) acrylate, methoxydiethylene glycol (meth) acrylate, methoxytetraethylene (meth) acrylate, methoxypolyethylene glycol # 400.
(Meth) acrylate, ethoxyethyl (meth) acrylate, ethoxydiethylene glycol (meth) acrylate, ethoxytetraethylene glycol (meth) acrylate, ethoxypolyethylene glycol # 400
Examples thereof include (meth) acrylate, and acrylic acid ester and methacrylic acid ester thereof can be used alone or in combination.
単量体ｂも樹脂の親水性や洗髪性に関与し、その使用量
は５〜２５重量％、好ましくは１０〜２５重量％であ
る。上記使用量が５重量％に満たないと、得られたフィ
ルムが水に難溶で洗髪性が不良になり、一方、それが２
５重量％を超えると、吸湿量が多くなると共に粘着性が
顕著になる。単量体ｂとして、既述のアクリル酸、メタ
クリル酸及びイタコン酸からなる群より選ばれた不飽和
カルボン酸を単独又は併用で使用することができる。The monomer b also contributes to the hydrophilicity and hair washability of the resin, and the amount used is 5 to 25% by weight, preferably 10 to 25% by weight. If the amount used is less than 5% by weight, the resulting film is poorly soluble in water and has poor hair washability.
When it exceeds 5% by weight, the amount of moisture absorption increases and the tackiness becomes remarkable. As the monomer b, an unsaturated carboxylic acid selected from the group consisting of acrylic acid, methacrylic acid and itaconic acid described above can be used alone or in combination.
単量体ｃは形成フィルムの柔軟性や耐水性に関与し、そ
の使用量は５〜２０重量％、好ましくは５〜１５重量％
である。上記使用量が５重量％に満たないと、フィルム
が硬く、耐水性が不良になり、一方、それが２０重量％
を超えると、フィルムが過剰に柔軟になると共に粘着性
が顕著になり、また洗髪性が低下する。The monomer c is involved in the flexibility and water resistance of the formed film, and the amount used is 5 to 20% by weight, preferably 5 to 15% by weight.
Is. If the amount used is less than 5% by weight, the film becomes hard and the water resistance becomes poor, while it is 20% by weight.
When it exceeds, the film becomes excessively flexible, the tackiness becomes remarkable, and the hair washability is deteriorated.
単量体ｃの具体例として、例えば、２−エチルヘキシル
（メタ）アクリレート、ドデシル（メタ）アクリレー
ト、パルミチル（メタ）アクリレート、ステアリル（メ
タ）アクリレート等をあげることができ、それらのアク
リル酸エステル、メタクリル酸エステルを単独又は併用
で使用することができる。Specific examples of the monomer c include, for example, 2-ethylhexyl (meth) acrylate, dodecyl (meth) acrylate, palmityl (meth) acrylate, stearyl (meth) acrylate, and the like. The acid esters can be used alone or in combination.
単量体ｄは、得られるフィルムに適度の硬度及び柔軟性
等を付与するものであり、その使用量は２０〜５０重量
％である。The monomer d imparts appropriate hardness and flexibility to the obtained film, and its amount used is 20 to 50% by weight.
単量体ｄの具体例として、例えば、メチル（メタ）アク
リレート、エチル（メタ）アクリレート、ブチル（メ
タ）アクリレート、イソブチル（メタ）アクリレート、
シクロヘキシル（メタ）アクリレート、酢酸ビニル、ビ
ニルピロリドン、（メタ）アクリルアミド、ジアセトン
（メタ）アクリルアミド、アクリロニトリル、スチレン
等をあげることができ、それらのビニル系単量体を単独
又は併用で使用することができる。Specific examples of the monomer d include, for example, methyl (meth) acrylate, ethyl (meth) acrylate, butyl (meth) acrylate, isobutyl (meth) acrylate,
Examples thereof include cyclohexyl (meth) acrylate, vinyl acetate, vinylpyrrolidone, (meth) acrylamide, diacetone (meth) acrylamide, acrylonitrile, and styrene, and those vinyl monomers can be used alone or in combination. .
上記の単量体ａ〜ｄの共重合は、親水性溶媒中における
通常の溶液重合により、例えば各単量体を親水性溶媒に
溶解し、重合開始剤を添加し、窒素気流下、溶媒の沸点
又はそれに近い温度で攪拌することにより行なうことが
できる。上記の単量体は、その全種類及び全量を重合当
初から存在させて、或は単量体の種類及び／又は量に関
して分割添加を行なうことにより共重合させる。上記溶
媒は、樹脂溶液中の固形分が３０〜６０重量％となるよ
うに使用することが好ましい。The copolymerization of the above-mentioned monomers a to d is carried out by ordinary solution polymerization in a hydrophilic solvent, for example, by dissolving each monomer in the hydrophilic solvent, adding a polymerization initiator, and adding the polymerization initiator under a nitrogen stream. It can be carried out by stirring at a temperature at or near the boiling point. The above-mentioned monomers are copolymerized by allowing all kinds and all amounts thereof to be present from the beginning of the polymerization, or by performing divided addition with respect to the kind and / or amount of the monomers. The solvent is preferably used such that the solid content in the resin solution is 30 to 60% by weight.
親水性溶媒として、例えばメチルアルコール、エチルア
ルコール、イソプロピルアルコール、ブチルアルコール
等の水に可溶の炭素数１〜４の脂肪族アルコール、例え
ば９５％エチルアルコール等の含水アルコール、さらに
アセトン、メチルセロソルブ、エチルセロソルブ、ジオ
キサン、酢酸メチル、ジメチルホルムアミド等を単独又
は併用で使用することができる。また、重合開始剤とし
て、例えば、過酸化ベンゾイル、過酸化ラウロイル等の
過酸化物、アゾビスイソブチロニトリル等のアゾ系化合
物を使用することが好ましい。Examples of hydrophilic solvents include water-soluble aliphatic alcohols having 1 to 4 carbon atoms such as methyl alcohol, ethyl alcohol, isopropyl alcohol, and butyl alcohol, hydrous alcohols such as 95% ethyl alcohol, and acetone and methyl cellosolve. Ethyl cellosolve, dioxane, methyl acetate, dimethylformamide and the like can be used alone or in combination. Further, it is preferable to use, for example, a peroxide such as benzoyl peroxide or lauroyl peroxide, or an azo compound such as azobisisobutyronitrile as the polymerization initiator.
上記共重合により得られた樹脂含有液に水溶性有機塩基
性物質を加えることにより、共重合樹脂を中和すると共
に水溶性にする。中和率は、５０〜１００％が好適であ
る。By adding a water-soluble organic basic substance to the resin-containing liquid obtained by the above copolymerization, the copolymerized resin is neutralized and becomes water-soluble. The neutralization rate is preferably 50 to 100%.
水溶性有機塩基性物質として、例えば、アンモニア水、
モノ、ジ又はトリエタノールアミン、モノ、ジ又はトリ
イソプロパノールアミン、モルホリン、アミノメチルプ
ロパノールアミン、アミノエチルプロパノールアミン、
アミノメチルプロパンジオール、アミノエチルプロパン
ジオール等を単独又は併用で使用することができる。特
に有機アミンを使用すると水を含有しない樹脂組成物が
得られるので、水分を忌避するエアゾールには好適であ
る。As the water-soluble organic basic substance, for example, aqueous ammonia,
Mono, di or triethanolamine, mono, di or triisopropanolamine, morpholine, aminomethylpropanolamine, aminoethylpropanolamine,
Aminomethyl propane diol, amino ethyl propane diol and the like can be used alone or in combination. In particular, when an organic amine is used, a resin composition containing no water can be obtained, which is suitable for an aerosol that repels water.
そのようにして得られた樹脂組成物は、共重合体の分子
量が５０００〜２０００００程度であり、前記共重合で
得られたる親水性溶媒溶液のままで、或は含水溶媒系と
して頭髪着色料の固着のために、好ましくは（頭髪着色
料／樹脂組成物）＝（1/1）〜（1/20）の比率（固形分
比率）で使用することができる。The resin composition thus obtained has a copolymer having a molecular weight of about 5,000 to 200,000, and is used as a hydrophilic solvent solution obtained by the copolymerization as it is, or as a water-containing solvent system for a hair coloring agent. For fixing, it can be preferably used in a ratio (solid content ratio) of (hair colorant / resin composition) = (1/1) to (1/20).
〔実施例１〜６〕 以下、本発明を実施例に基いて説明する。なお、以下に
記載する「％」及び「部」は何れも重量基準である。Examples 1 to 6 Hereinafter, the present invention will be described based on examples. In addition, "%" and "part" described below are based on weight.
〈樹脂組成物の製造〉 還流冷却器、温度計、窒素置換用ガラス管、滴下ロート
及び攪拌機を取付けた１四つ口フラスコに、重合性単
量体ａ〜ｄ２００部、エタノール１００部、重合開始剤
０．５〜２部を加え、窒素気流下、８０℃で還流加熱
し、４時間重合を行なう。重合後、冷却し、５０℃にて
水溶性有機塩基性物質のエタノール溶液を添加し、固形
分５０％となるようにエタノールで希釈する。<Production of Resin Composition> A 1-four-necked flask equipped with a reflux condenser, a thermometer, a glass tube for nitrogen substitution, a dropping funnel, and a stirrer, 200 parts of polymerizable monomers a to d, 100 parts of ethanol, and initiation of polymerization. 0.5 to 2 parts of the agent is added, and the mixture is heated under reflux at 80 ° C. under a nitrogen stream to carry out polymerization for 4 hours. After the polymerization, the mixture is cooled, an ethanol solution of a water-soluble organic basic substance is added at 50 ° C., and diluted with ethanol so that the solid content becomes 50%.
表１に、実施例１〜６及び比較例１〜６について、重合
性単量体ａ〜ｄの組成、重合開始剤や水溶性有機塩基性
物質の種類及び使用量等を示す。Table 1 shows the compositions of the polymerizable monomers a to d, the types and the amounts of the polymerization initiator and the water-soluble organic basic substance, for Examples 1 to 6 and Comparative Examples 1 to 6.
〈カラーベースの調製〉 各実施例及び比較例の上記樹脂組成物（固形分５０％）
４０％を頭髪着色料としてのカーボンブラック１０％、
エタノール５０％と混合し、３段ロールを用いてカラー
ベースを調製する。 <Preparation of color base> The resin composition of each Example and Comparative Example (solid content 50%)
40% carbon black 10% as hair coloring,
Mix with 50% ethanol and prepare a color base using a triple roll.
〈カラーフォームの調製〉 上記カラーベースを使用し、下記の組成で３タイプ（タ
イプＡ：消泡が速い、タイプＢ：消泡がタイプＡとタイ
プＣの中間程度、及びタイプＣ：消泡が遅い）のカラー
フォームからなる頭髪着色剤を調製した。<Preparation of Color Foam> Using the above color base, the following compositions have 3 types (type A: fast defoaming, type B: defoaming intermediate between type A and type C, and type C: slow defoaming). The hair coloring agent consisting of the color foam of 1) was prepared.
〈カラースプレーの調製〉 上記カラーベースを使用し、下記の組成でカラースプレ
ーからなる頭髪着色剤を調製した。 <Preparation of Color Spray> Using the above color base, a hair coloring agent composed of a color spray was prepared with the following composition.
組 成（％） カラーベース ６ エタノール ３４ フロンガスＦ−１１ ２４ フロンガスＦ−１２ ３６ （但し、実施例３及び比較例３については、有機塩基性
物質としてアンモニア水を使用するため、カラースプレ
ーの調製が不可能である。） 〈マスカラタイプの調製〉 上記カラーベースを使用し、下記の組成でマスカラタイ
プらなる頭髪着色剤を調製した。Composition (%) Color base 6 Ethanol 34 Freon gas F-11 24 Freon gas F-12 36 (However, since Example 3 and Comparative Example 3 use aqueous ammonia as an organic basic substance, preparation of a color spray is not possible. It is possible.) <Preparation of mascara type> Using the above color base, a hair coloring agent of mascara type was prepared with the following composition.
組 成（％） カラーベース １０ 樹脂組成物（固形分５０％） ４ エタノール １０ 精製水 ７６ 〈性能評価〉 脱色毛髪１０cm、約１ｇの毛束に適量の上記頭髪着色剤
を塗布し、ドライヤー（温風）にて乾燥後の毛髪につい
て下記の各性能を評価した結果を表２に示す。Composition (%) Color base 10 Resin composition (solid content 50%) 4 Ethanol 10 Purified water 76 <Performance evaluation> Decolorized hair 10 cm, about 1 g of hair is coated with an appropriate amount of the above hair coloring agent, and a dryer (warm air) Table 2 shows the results of evaluating the following performances of the dried hair in ().
（１）粘着性 乾燥後の毛髪の粘着性を指触で評価する。(1) Adhesiveness The adhesiveness of the hair after drying is evaluated by touch with a finger.
○：粘着なし、 △：粘着少しあり、 ×：粘着大 （２）フレーキング 乾燥後の毛髪を櫛でとき、樹脂の脱落の有無を評価す
る。◯: No adhesion, Δ: Some adhesion, X: Large adhesion (2) Flaking When the dried hair is combed, it is evaluated whether or not the resin has fallen off.
○：粘着なし、 △：脱落少しあり、 ×：脱落多い （３）洗髪性 市販品シャンプーの１％水溶液を作り、乾燥後の毛髪を
３５℃にて洗浄し、水洗後に乾燥し、脱落の程度を評価
する。◯: No stickiness, Δ: Slight dropout, X: Many dropouts (3) Hair washability Make a 1% aqueous solution of a commercial shampoo, wash the dried hair at 35 ° C., wash it with water, and then dry it to remove it. Evaluate.
○：残留物なし、 △：残留物少量、 ×：残留物多量 （４）耐水性 乾燥後の毛髪を４０℃の水に３０秒間浸漬した後、それ
を取出し、白色布にてしごき、白色布への色落ちの程度
を評価する。◯: No residue, Δ: Small amount of residue, ×: Large amount of residue (4) Water resistance After immersing the dried hair in water at 40 ° C for 30 seconds, take it out, and iron it with a white cloth, white cloth To evaluate the degree of discoloration.
○：色落ちなし、 △：色落ち少しあり、 ×：色落ち
多い（部分溶解あり） （５）耐摩性 摩擦堅牢度試験機（ＪＩＳ Ｐ−８１３６）を使用し、
白色綿布をテーブルに固定すると共に乾燥後の毛髪を上
部に固定し、荷重３００ｇを３０回摩擦する。綿布への
色落ちの程度を１〜５の５段階で評価する。◯: No discoloration, Δ: Some discoloration, ×: Many discoloration (with partial dissolution) (5) Abrasion resistance Using a friction fastness tester (JIS P-8136),
A white cotton cloth is fixed to the table and the hair after drying is fixed to the upper part, and a load of 300 g is rubbed 30 times. The degree of discoloration on the cotton cloth is evaluated on a scale of 1 to 5.
１：着色殆どなし、 ５：全面着色あり、 〔発明の効果〕 以上のように、本発明は、毛髪への密着性がよく、形成
フィルムが柔軟であり、粘着性及びフレーキングがな
く、しかも洗髪性、耐水性及び耐摩性に優れた頭髪着色
料固着用樹脂組成物及びそれを用いた頭髪着色剤を提供
することができる。1: Almost no coloring, 5: Full coloring, [Effect of the Invention] As described above, the present invention has good adhesion to hair, a flexible formed film, no tackiness and flaking, and excellent hair washability, water resistance and abrasion resistance. A colorant fixing resin composition and a hair coloring agent using the same can be provided.
Claims (2)
溶性有機塩基性物質で中和してなる頭髪着色料固着用樹
脂組成物。 ａ．次式で示されるアクリル酸エステル及び／又はメタ
クリル酸エステルからなる少なくとも１種の単量体
３０〜７０重量％ （式中、Ｒ1は水素原子又はメチル基、Ｒ2はメチル基又
はエチル基、ｎは１〜１０の整数である。） ｂ．アクリル酸、メタクリル酸及びイタコン酸からなる
群より選ばれた少なくとも１種の単量体 ５〜
２５重量％ ｃ．アクリル酸及び／又はメタクリル酸の炭素数８〜１
８の脂肪族アルコールのエステルからなる少なくとも１
種の単量体 ５〜２０重量％ ｄ．その他のビニル系単量体 ２０〜５０重量
％1. A resin composition for fixing a hair colorant, which is obtained by copolymerizing the following polymerizable monomers a to d and neutralizing with a water-soluble organic basic substance. a. At least one monomer consisting of acrylic acid ester and / or methacrylic acid ester represented by the following formula
30-70% by weight (In the formula, R 1 is a hydrogen atom or a methyl group, R 2 is a methyl group or an ethyl group, and n is an integer of 1 to 10.) b. At least one monomer selected from the group consisting of acrylic acid, methacrylic acid, and itaconic acid;
25% by weight c. Acrylic acid and / or methacrylic acid having 8 to 1 carbon atoms
At least 1 consisting of an ester of 8 aliphatic alcohols
Seed monomer 5-20% by weight d. Other vinyl monomers 20 to 50% by weight
物を含む頭髪着色剤。2. A hair coloring agent containing the resin composition for fixing hair coloring agent according to claim 1.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4024588A JPH0611690B2 (en) | 1988-02-23 | 1988-02-23 | Resin composition for fixing hair coloring agent and hair coloring agent using the same |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP4024588A JPH0611690B2 (en) | 1988-02-23 | 1988-02-23 | Resin composition for fixing hair coloring agent and hair coloring agent using the same |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPH01213221A JPH01213221A (en) | 1989-08-28 |
| JPH0611690B2 true JPH0611690B2 (en) | 1994-02-16 |
Family
ID=12575322
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP4024588A Expired - Fee Related JPH0611690B2 (en) | 1988-02-23 | 1988-02-23 | Resin composition for fixing hair coloring agent and hair coloring agent using the same |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPH0611690B2 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2322863A (en) * | 1997-03-05 | 1998-09-09 | Kansai Paint Co Ltd | Water soluble acrylic resin, and compositions and method using it |
| JP2022528492A (en) * | 2019-04-03 | 2022-06-13 | エスペーセーエム・エスアー | Cosmetic composition for hair |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH0459719A (en) * | 1990-06-25 | 1992-02-26 | Osaka Organic Chem Ind Ltd | Resin composition for aerosol |
| US7056346B1 (en) | 1996-05-23 | 2006-06-06 | L'oreal S.A. | Direct dye composition for the hair, comprising a crosslinked polymer containing acrylic units and C10-C30 alkyl acrylate units |
| FR2748932B1 (en) * | 1996-05-23 | 1998-07-03 | Oreal | DIRECT HAIR DYE COMPOSITION COMPRISING A CROSSLINKED POLYMER WITH ACRYLIC PATTERNS AND C10-C30 ACYLATE ACRYLATES |
| DE19838851A1 (en) | 1998-08-26 | 2000-03-02 | Basf Ag | Cosmetic agents, especially hair cosmetics, comprise water-soluble or water dispersible polymers which are also useful in pharmaceutical products and coatings for the textile, paper, printing, leather and adhesive industries |
| KR101353365B1 (en) * | 2005-07-26 | 2014-01-20 | 로디아 인코포레이티드 | Polymers with pendant poly(alkyleneoxy) substituent groups and their use in personal care applications |
| JP2011026304A (en) * | 2009-06-24 | 2011-02-10 | Mitsubishi Chemicals Corp | Copolymer for cosmetic, and composition for cosmetic containing the same |
| US9302126B2 (en) * | 2010-07-30 | 2016-04-05 | Wei Gao | Fixative polymer compatible with hair styling composition |
| JP5680895B2 (en) * | 2010-07-30 | 2015-03-04 | 株式会社ファンケル | Polymer emulsifier and emulsified composition |
-
1988
- 1988-02-23 JP JP4024588A patent/JPH0611690B2/en not_active Expired - Fee Related
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB2322863A (en) * | 1997-03-05 | 1998-09-09 | Kansai Paint Co Ltd | Water soluble acrylic resin, and compositions and method using it |
| GB2322863B (en) * | 1997-03-05 | 1999-05-12 | Kansai Paint Co Ltd | Water-soluble acrylic resin,and compositions and method using it |
| JP2022528492A (en) * | 2019-04-03 | 2022-06-13 | エスペーセーエム・エスアー | Cosmetic composition for hair |
Also Published As
| Publication number | Publication date |
|---|---|
| JPH01213221A (en) | 1989-08-28 |
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