JP2012001480A - Temporarily hair-dyeing agent composition - Google Patents
Temporarily hair-dyeing agent composition Download PDFInfo
- Publication number
- JP2012001480A JP2012001480A JP2010137311A JP2010137311A JP2012001480A JP 2012001480 A JP2012001480 A JP 2012001480A JP 2010137311 A JP2010137311 A JP 2010137311A JP 2010137311 A JP2010137311 A JP 2010137311A JP 2012001480 A JP2012001480 A JP 2012001480A
- Authority
- JP
- Japan
- Prior art keywords
- group
- organopolysiloxane
- meth
- hair
- component
- 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.)
- Granted
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 48
- 239000000975 dye Substances 0.000 title abstract description 7
- 229920001296 polysiloxane Polymers 0.000 claims abstract description 58
- 239000000049 pigment Substances 0.000 claims abstract description 19
- 125000000217 alkyl group Chemical group 0.000 claims abstract description 16
- 239000000982 direct dye Substances 0.000 claims abstract description 11
- 125000002947 alkylene group Chemical group 0.000 claims abstract description 9
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000003710 aryl alkyl group Chemical group 0.000 claims abstract description 6
- 125000003118 aryl group Chemical group 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 6
- -1 methacryloyl Chemical group 0.000 claims description 51
- 239000000178 monomer Substances 0.000 claims description 43
- 239000001027 temporary hair color Substances 0.000 claims description 41
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 38
- 229920002554 vinyl polymer Polymers 0.000 claims description 32
- 125000004432 carbon atom Chemical group C* 0.000 claims description 29
- 125000002091 cationic group Chemical group 0.000 claims description 23
- 229920001577 copolymer Polymers 0.000 claims description 19
- 229920002545 silicone oil Polymers 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 8
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 claims description 6
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims description 5
- 125000003342 alkenyl group Chemical group 0.000 claims description 4
- 239000000470 constituent Substances 0.000 claims description 4
- 238000004043 dyeing Methods 0.000 claims description 4
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 238000010526 radical polymerization reaction Methods 0.000 claims description 3
- YZCKVEUIGOORGS-IGMARMGPSA-N Protium Chemical compound [1H] YZCKVEUIGOORGS-IGMARMGPSA-N 0.000 claims description 2
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- 125000005843 halogen group Chemical group 0.000 claims description 2
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- 238000012546 transfer Methods 0.000 abstract description 17
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- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 12
- 239000002904 solvent Substances 0.000 description 11
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- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 10
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- 230000015572 biosynthetic process Effects 0.000 description 9
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- ODUCDPQEXGNKDN-UHFFFAOYSA-N nitroxyl Chemical compound O=N ODUCDPQEXGNKDN-UHFFFAOYSA-N 0.000 description 8
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- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 6
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 6
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 6
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 6
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- 239000012467 final product Substances 0.000 description 5
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- SZVJSHCCFOBDDC-UHFFFAOYSA-N iron(II,III) oxide Inorganic materials O=[Fe]O[Fe]O[Fe]=O SZVJSHCCFOBDDC-UHFFFAOYSA-N 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 5
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 5
- 239000002994 raw material Substances 0.000 description 5
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- 150000005846 sugar alcohols Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
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- NYEZZYQZRQDLEH-UHFFFAOYSA-N 2-ethyl-4,5-dihydro-1,3-oxazole Chemical compound CCC1=NCCO1 NYEZZYQZRQDLEH-UHFFFAOYSA-N 0.000 description 4
- KWIUHFFTVRNATP-UHFFFAOYSA-N Betaine Natural products C[N+](C)(C)CC([O-])=O KWIUHFFTVRNATP-UHFFFAOYSA-N 0.000 description 4
- 241000283707 Capra Species 0.000 description 4
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- KWIUHFFTVRNATP-UHFFFAOYSA-O N,N,N-trimethylglycinium Chemical compound C[N+](C)(C)CC(O)=O KWIUHFFTVRNATP-UHFFFAOYSA-O 0.000 description 4
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- 239000010426 asphalt Substances 0.000 description 4
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- 238000004448 titration Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
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- 229910052742 iron Inorganic materials 0.000 description 1
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- JCDAAXRCMMPNBO-UHFFFAOYSA-N iron(3+);oxygen(2-);titanium(4+) Chemical compound [O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[O-2].[Ti+4].[Ti+4].[Fe+3].[Fe+3] JCDAAXRCMMPNBO-UHFFFAOYSA-N 0.000 description 1
- NCNCGGDMXMBVIA-UHFFFAOYSA-L iron(ii) hydroxide Chemical compound [OH-].[OH-].[Fe+2] NCNCGGDMXMBVIA-UHFFFAOYSA-L 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
- 150000002576 ketones Chemical class 0.000 description 1
- 239000004310 lactic acid Substances 0.000 description 1
- 235000014655 lactic acid Nutrition 0.000 description 1
- 239000005001 laminate film Substances 0.000 description 1
- 229940031957 lauric acid diethanolamide Drugs 0.000 description 1
- SXQCTESRRZBPHJ-UHFFFAOYSA-M lissamine rhodamine Chemical compound [Na+].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=C(S([O-])(=O)=O)C=C1S([O-])(=O)=O SXQCTESRRZBPHJ-UHFFFAOYSA-M 0.000 description 1
- 238000010550 living polymerization reaction Methods 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
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229920003117 medium viscosity grade hydroxypropyl cellulose Polymers 0.000 description 1
- 229940102396 methyl bromide Drugs 0.000 description 1
- LNOPIUAQISRISI-UHFFFAOYSA-N n'-hydroxy-2-propan-2-ylsulfonylethanimidamide Chemical compound CC(C)S(=O)(=O)CC(N)=NO LNOPIUAQISRISI-UHFFFAOYSA-N 0.000 description 1
- ZIUHHBKFKCYYJD-UHFFFAOYSA-N n,n'-methylenebisacrylamide Chemical compound C=CC(=O)NCNC(=O)C=C ZIUHHBKFKCYYJD-UHFFFAOYSA-N 0.000 description 1
- YKYONYBAUNKHLG-UHFFFAOYSA-N n-Propyl acetate Natural products CCCOC(C)=O YKYONYBAUNKHLG-UHFFFAOYSA-N 0.000 description 1
- ILCQQHAOOOVHQJ-UHFFFAOYSA-N n-ethenylprop-2-enamide Chemical compound C=CNC(=O)C=C ILCQQHAOOOVHQJ-UHFFFAOYSA-N 0.000 description 1
- 125000001280 n-hexyl group Chemical group C(CCCCC)* 0.000 description 1
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- DYUWTXWIYMHBQS-UHFFFAOYSA-N n-prop-2-enylprop-2-en-1-amine Chemical compound C=CCNCC=C DYUWTXWIYMHBQS-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000004923 naphthylmethyl group Chemical group C1(=CC=CC2=CC=CC=C12)C* 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 125000001971 neopentyl group Chemical group [H]C([*])([H])C(C([H])([H])[H])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 230000003472 neutralizing effect Effects 0.000 description 1
- 229910017604 nitric acid Inorganic materials 0.000 description 1
- 150000002825 nitriles Chemical class 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 125000004433 nitrogen atom Chemical group N* 0.000 description 1
- 125000001196 nonadecyl 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])C([H])([H])[H] 0.000 description 1
- 125000001400 nonyl 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])[H] 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 125000002347 octyl 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])[H] 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000012860 organic pigment Substances 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- BMMGVYCKOGBVEV-UHFFFAOYSA-N oxo(oxoceriooxy)cerium Chemical compound [Ce]=O.O=[Ce]=O BMMGVYCKOGBVEV-UHFFFAOYSA-N 0.000 description 1
- BWOROQSFKKODDR-UHFFFAOYSA-N oxobismuth;hydrochloride Chemical compound Cl.[Bi]=O BWOROQSFKKODDR-UHFFFAOYSA-N 0.000 description 1
- DXGLGDHPHMLXJC-UHFFFAOYSA-N oxybenzone Chemical compound OC1=CC(OC)=CC=C1C(=O)C1=CC=CC=C1 DXGLGDHPHMLXJC-UHFFFAOYSA-N 0.000 description 1
- 229960001173 oxybenzone Drugs 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N p-toluenesulfonic acid Substances CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 125000001147 pentyl group Chemical group C(CCCC)* 0.000 description 1
- 239000001024 permanent hair color Substances 0.000 description 1
- 125000005561 phenanthryl group Chemical group 0.000 description 1
- 229940057874 phenyl trimethicone Drugs 0.000 description 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 1
- 239000000419 plant extract Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920006254 polymer film Polymers 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920001451 polypropylene glycol Polymers 0.000 description 1
- 238000012673 precipitation polymerization Methods 0.000 description 1
- 239000003755 preservative agent Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- QJWFJOSRSZOLKK-UHFFFAOYSA-N prop-2-enamide Chemical class NC(=O)C=C.NC(=O)C=C QJWFJOSRSZOLKK-UHFFFAOYSA-N 0.000 description 1
- 229940090181 propyl acetate Drugs 0.000 description 1
- 239000001057 purple pigment Substances 0.000 description 1
- KXXXUIKPSVVSAW-UHFFFAOYSA-K pyranine Chemical compound [Na+].[Na+].[Na+].C1=C2C(O)=CC(S([O-])(=O)=O)=C(C=C3)C2=C2C3=C(S([O-])(=O)=O)C=C(S([O-])(=O)=O)C2=C1 KXXXUIKPSVVSAW-UHFFFAOYSA-K 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000000985 reactive dye Substances 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 239000001054 red pigment Substances 0.000 description 1
- 125000000467 secondary amino group Chemical group [H]N([*:1])[*:2] 0.000 description 1
- 239000001026 semi permanent hair color Substances 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 229920006268 silicone film Polymers 0.000 description 1
- LLELVHKMCSBMCX-UHFFFAOYSA-M sodium 1-[(4-chloro-5-methyl-2-sulfophenyl)diazenyl]naphthalen-2-olate Chemical compound [Na+].Cc1cc(N=Nc2c(O)ccc3ccccc23)c(cc1Cl)S([O-])(=O)=O LLELVHKMCSBMCX-UHFFFAOYSA-M 0.000 description 1
- JAOZKJMVYIWLKU-UHFFFAOYSA-N sodium 7-hydroxy-8-[(4-sulfonaphthalen-1-yl)diazenyl]naphthalene-1,3-disulfonic acid Chemical compound C1=CC=C2C(=C1)C(=CC=C2S(=O)(=O)O)N=NC3=C(C=CC4=CC(=CC(=C43)S(=O)(=O)O)S(=O)(=O)O)O.[Na+] JAOZKJMVYIWLKU-UHFFFAOYSA-N 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- MNCGMVDMOKPCSQ-UHFFFAOYSA-M sodium;2-phenylethenesulfonate Chemical compound [Na+].[O-]S(=O)(=O)C=CC1=CC=CC=C1 MNCGMVDMOKPCSQ-UHFFFAOYSA-M 0.000 description 1
- STZCRXQWRGQSJD-UHFFFAOYSA-N sodium;4-[[4-(dimethylamino)phenyl]diazenyl]benzenesulfonic acid Chemical compound [Na+].C1=CC(N(C)C)=CC=C1N=NC1=CC=C(S(O)(=O)=O)C=C1 STZCRXQWRGQSJD-UHFFFAOYSA-N 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 239000005720 sucrose Substances 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 238000010558 suspension polymerization method Methods 0.000 description 1
- 210000004243 sweat Anatomy 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 125000001302 tertiary amino group Chemical group 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000005425 toluyl group Chemical group 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- VPYJNCGUESNPMV-UHFFFAOYSA-N triallylamine Chemical compound C=CCN(CC=C)CC=C VPYJNCGUESNPMV-UHFFFAOYSA-N 0.000 description 1
- 125000002889 tridecyl 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])[H] 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- DTQVDTLACAAQTR-UHFFFAOYSA-N trifluoroacetic acid Substances OC(=O)C(F)(F)F DTQVDTLACAAQTR-UHFFFAOYSA-N 0.000 description 1
- NWKBFCIAPOSTKG-UHFFFAOYSA-M trimethyl-[3-[(3-methyl-5-oxo-1-phenyl-4h-pyrazol-4-yl)diazenyl]phenyl]azanium;chloride Chemical compound [Cl-].CC1=NN(C=2C=CC=CC=2)C(=O)C1N=NC1=CC=CC([N+](C)(C)C)=C1 NWKBFCIAPOSTKG-UHFFFAOYSA-M 0.000 description 1
- LINXHFKHZLOLEI-UHFFFAOYSA-N trimethyl-[phenyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound C[Si](C)(C)O[Si](O[Si](C)(C)C)(O[Si](C)(C)C)C1=CC=CC=C1 LINXHFKHZLOLEI-UHFFFAOYSA-N 0.000 description 1
- 125000002221 trityl group Chemical group [H]C1=C([H])C([H])=C([H])C([H])=C1C([*])(C1=C(C(=C(C(=C1[H])[H])[H])[H])[H])C1=C([H])C([H])=C([H])C([H])=C1[H] 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 125000002948 undecyl 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])[H] 0.000 description 1
- NQPDZGIKBAWPEJ-UHFFFAOYSA-N valeric acid Chemical compound CCCCC(O)=O NQPDZGIKBAWPEJ-UHFFFAOYSA-N 0.000 description 1
- 229960000834 vinyl ether Drugs 0.000 description 1
- 239000001993 wax Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Landscapes
- Cosmetics (AREA)
Abstract
Description
本発明は、一時染毛剤組成物に関する。 The present invention relates to a temporary hair dye composition.
染毛剤は、酸化染料を用いて頭髪中で発色させることで着色する永久染毛剤（ヘアカラー）、直接染料を頭髪に浸透吸着させることで着色する半永久染毛剤（ヘアマニキュア）、頭髪上に着色剤（主として顔料）を含む着色皮膜を形成させることで着色する一時染毛剤などに分類される。このうち、一時染毛剤は、頭髪へのダメージが少なく、洗髪により容易に除去でき、簡便に用いることができることから、気軽に毛染めを楽しむことができるものとして好まれている。 Hair dyes are permanent hair dyes that are colored by coloring in the hair using an oxidative dye (hair color), semi-permanent hair dyes that are colored by directly adsorbing the dye on the hair (hair manicure), and hair. It is classified as a temporary hair dye that is colored by forming a colored film containing a colorant (mainly a pigment) thereon. Of these, temporary hair dyes are preferred as being able to enjoy hair dyeing casually because they have little damage to the hair, can be easily removed by shampooing, and can be easily used.
従来の一時染毛剤としては、着色剤を着色皮膜として頭髪上に固着させるとともに、この着色皮膜に耐水性を付与し、また摩擦などによる皮膚や衣類への色移りを防止するため、皮膜形成ポリマーを含有させた組成物などが知られている（例えば、特許文献１）。 As a conventional temporary hair dye, a film is formed to fix the colorant on the hair as a colored film, to impart water resistance to the colored film, and to prevent color transfer to the skin and clothing due to friction, etc. A composition containing a polymer is known (for example, Patent Document 1).
しかしながら、このような皮膜形成ポリマーを用いた一時染毛剤では、着色剤の固着や耐水性には優れるものの、形成された着色皮膜が硬いため、着色された毛髪の感触（やわらかさ）が劣るという問題があった。すなわち、着色された毛髪の風合いに関して、ごわつく、きしむ、などといった問題があった。 However, although the temporary hair dye using such a film-forming polymer is excellent in fixing of the colorant and water resistance, the formed colored film is hard, so the feel (softness) of the colored hair is inferior. There was a problem. That is, there is a problem that the texture of the colored hair is stiff and squeaky.
そこで、一時染毛剤において、着色効果、汗や雨などに対する耐水性、良好な風合い感を得るために、適当な着色皮膜を得る必要があり、このため、上記のような皮膜形成ポリマーを用いた一時染毛剤では、更にシリコーン油などの油剤を併用することによりポリマー皮膜のごわつき感の低減が図られていた（特許文献２）。しかしながら、シリコーン油を多量に用いた時やシリコーン油と皮膜形成ポリマーとの組合せによっては、皮膜表面に油が滲みだし、ベタツキによる感触低下、さらには指などが触れたときの色移りが起こるなどの問題があった。 Therefore, in order to obtain a coloring effect, water resistance against sweat and rain, and a good texture in a temporary hair dye, it is necessary to obtain an appropriate colored film. For this reason, a film-forming polymer as described above is used. In the temporary hair dyes that have been used, reduction of the polymer film's stiff feeling has been attempted by further using an oil agent such as silicone oil (Patent Document 2). However, when a large amount of silicone oil is used, or depending on the combination of silicone oil and film-forming polymer, the oil begins to ooze out on the surface of the film, resulting in a decrease in feel due to stickiness, and color transfer when touched by a finger, etc. There was a problem.
一方、特許文献３には、一定条件下において伸長率０〜15％の範囲で破断又は塑性変形を生じないオルガノポリシロキサン及びこれを含有する毛髪セット剤が開示されている。この毛髪セット剤は、毛髪のセット性及びその保持性に優れ、セット後の毛髪に柔軟でゴワゴワしない良好な感触を付与できるものであるが、染毛剤への適用のみならず、一時染毛剤への適用については記述も示唆もない。 On the other hand, Patent Document 3 discloses an organopolysiloxane that does not break or plastically deform within a range of 0 to 15% elongation under a certain condition and a hair setting agent containing the same. This hair setting agent is excellent in setting and retaining properties of hair, and can give a good feel that is soft and irritating to the hair after setting, but it is not only applied to hair dyes, but also temporary hair dyeing There is no description or suggestion about application to the drug.
本発明は、一時染毛剤の基本性能である、着色性、耐水性、色移りのし難さのみならず、着色毛髪の感触（やわらかさ）の良さ、べたつきのなさ、処方液の毛髪上への塗布しやすさにも優れた一時染毛剤を提供することを課題とする。 The present invention is not limited to the basic properties of temporary hair dyes, such as colorability, water resistance, and difficulty of color transfer, but also the feel (softness) of colored hair, non-stickiness, It is an object of the present invention to provide a temporary hair dye excellent in ease of application to the skin.
本発明者らは、上記特許文献３に開示されているオルガノポリシロキサンについて、上記特許文献３には記載されていない、一時染毛剤への適用について検討を行った結果、このうち特定範囲のオルガノポリシロキサンを特定の配合組成において用いた場合に、一時染毛剤の基本性能である、着色性、耐水性、色移りのし難さ、速乾性のみならず、着色毛髪の感触（風合い）の良さ、べたつきのなさ、処方液の毛髪上への塗布しやすさをも兼ね備えた卓越した性能が得られることを見出した。 As a result of examining the application of the organopolysiloxane disclosed in Patent Document 3 to a temporary hair dye that is not described in Patent Document 3, the present inventors have a specific range. When organopolysiloxane is used in a specific composition, not only the basic properties of temporary hair dyes, which are the colorability, water resistance, difficulty of color transfer, quick drying, but also the feel of colored hair (feel) The present inventors have found that excellent performance can be obtained, which has both good quality, no stickiness, and ease of application of the prescription solution onto the hair.
本発明は、次の成分(A)及び(B)を含有し、成分(A)の含有量が３〜20質量％である一時染毛剤組成物を提供するものである。
(A) 主鎖を構成するオルガノポリシロキサンセグメントのケイ素原子の少なくとも２つに、ヘテロ原子を含むアルキレン基を介して、下記一般式(1)；
The present invention provides a temporary hair dye composition containing the following components (A) and (B), wherein the content of the component (A) is 3 to 20% by mass.
(A) At least two silicon atoms of the organopolysiloxane segment constituting the main chain, via an alkylene group containing a hetero atom, the following general formula (1);
〔式中、Ｒ1は水素原子、炭素数１〜22のアルキル基、アラルキル基又はアリール基を示し、ｎは２又は３を示す。〕
で表される繰り返し単位からなるポリ（N-アシルアルキレンイミン）セグメントが結合してなるオルガノポリシロキサンであって、
主鎖を構成するオルガノポリシロキサンセグメント（ａ）と、ポリ（N-アシルアルキレンイミン）セグメント（ｂ）との質量比（ａ／ｂ）が83／17〜98／2であり、
主鎖を構成するオルガノポリシロキサンの重量平均分子量が10,000〜200,000であり、
隣接するポリ（N-アシルアルキレンイミン）セグメント間におけるオルガノポリシロキサンセグメントの重量平均分子量（グラフト点間分子量）が12,000〜30,000である、
オルガノポリシロキサン
(B) 顔料及び／又は直接染料
[Wherein, R 1 represents a hydrogen atom, an alkyl group having 1 to 22 carbon atoms, an aralkyl group or an aryl group, and n represents 2 or 3. ]
An organopolysiloxane formed by bonding poly (N-acylalkyleneimine) segments composed of repeating units represented by:
The mass ratio (a / b) between the organopolysiloxane segment (a) constituting the main chain and the poly (N-acylalkylenimine) segment (b) is 83/17 to 98/2,
The weight average molecular weight of the organopolysiloxane constituting the main chain is 10,000 to 200,000,
The weight average molecular weight (molecular weight between graft points) of the organopolysiloxane segment between adjacent poly (N-acylalkyleneimine) segments is 12,000 to 30,000,
Organopolysiloxane
(B) Pigments and / or direct dyes
本発明の一時染毛剤組成物は、基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさ、塗布しやすさをも兼ね備えるものである。 The temporary hair dye composition of the present invention has the basic performance of colorability, water resistance of the colored film, difficulty in color transfer, soft touch, non-stickiness, and ease of application. It is.
〔(A)：オルガノポリシロキサン〕
成分(A)において、ポリ（N-アシルアルキレンイミン）セグメントは、オルガノポリシロキサンセグメントを構成する任意のケイ素原子に、ヘテロ原子を含むアルキレン基を介して少なくとも２つ結合することが可能であるが、両末端を除く１以上のケイ素原子に上記アルキレン基を介して結合していることが好ましく、両末端を除く２以上のケイ素原子に上記アルキレン基を介して結合していることがより好ましい。
[(A): Organopolysiloxane]
In component (A), at least two poly (N-acylalkyleneimine) segments can be bonded to any silicon atom constituting the organopolysiloxane segment via an alkylene group containing a hetero atom. In addition, it is preferably bonded to one or more silicon atoms excluding both ends via the alkylene group, and more preferably bonded to two or more silicon atoms excluding both ends via the alkylene group.
オルガノポリシロキサンセグメントとポリ（N-アシルアルキレンイミン）との結合において介在するヘテロ原子を含むアルキレン基としては、窒素原子、酸素原子及び／又はイオウ原子を１〜３個含む炭素数２〜20のアルキレン基が挙げられる。その具体例としては、以下のものが挙げられる。 The alkylene group containing a hetero atom intervening in the bond between an organopolysiloxane segment and poly (N-acylalkyleneimine) has 2 to 20 carbon atoms containing 1 to 3 nitrogen atoms, oxygen atoms and / or sulfur atoms. An alkylene group is mentioned. Specific examples thereof include the following.
ポリ（N-アシルアルキレンイミン）セグメントを構成するN-アシルアルキレンイミン単位は前記一般式(1)で表されるものであるが、一般式(1)において、Ｒ1の炭素数１〜22のアルキル基としては、例えば、炭素数１〜22の直鎖、分岐状又は環状のアルキル基が例示され、具体的には、メチル基、エチル基、n-プロピル基、イソプロピル基、n-ブチル基、tert-ブチル基、ペンチル基、ヘキシル基、シクロへキシル基、ヘプチル基、オクチル基、ノニル基、デシル基、ウンデシル基、ドデシル基、オクタデシル基、ノナデシル基、エイコシル基、ドコシル基等が例示される。中でも、炭素数１〜10、特に炭素数１〜６のアルキル基がより好ましい。 The N-acylalkyleneimine unit constituting the poly (N-acylalkylenimine) segment is represented by the general formula (1). In the general formula (1), R 1 has 1 to 22 carbon atoms. Examples of the alkyl group include linear, branched or cyclic alkyl groups having 1 to 22 carbon atoms, and specifically include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, and an n-butyl group. Tert-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl, dodecyl, octadecyl, nonadecyl, eicosyl, docosyl, etc. The Among these, an alkyl group having 1 to 10 carbon atoms, particularly 1 to 6 carbon atoms is more preferable.
アラルキル基としては、例えば、炭素数７〜15のアラルキル基が例示され、具体的には、ベンジル基、フェネチル基、トリチル基、ナフチルメチル基、アントラセニルメチル基等が例示される。中でも、炭素数７〜14、特に炭素数７〜10のアラルキル基がより好ましい。 Examples of the aralkyl group include aralkyl groups having 7 to 15 carbon atoms, and specific examples include a benzyl group, a phenethyl group, a trityl group, a naphthylmethyl group, and an anthracenylmethyl group. Among them, an aralkyl group having 7 to 14 carbon atoms, particularly 7 to 10 carbon atoms is more preferable.
アリール基としては、例えば、炭素数６〜14のアリール基が例示され、具体的には、フェニル基、トリル基、キシリル基、ナフチル基、ビフェニル基、アントリル基、フェナントリル基等が例示され、中でも、炭素数６〜12、特に炭素数６〜９のアリール基がより好ましい。 Examples of the aryl group include an aryl group having 6 to 14 carbon atoms, and specific examples include a phenyl group, a tolyl group, a xylyl group, a naphthyl group, a biphenyl group, an anthryl group, and a phenanthryl group. An aryl group having 6 to 12 carbon atoms, particularly 6 to 9 carbon atoms is more preferable.
これらの中でも、Ｒ1としては、炭素数１〜６のアルキル基が特に好ましい。 Among these, R 1, particularly preferably an alkyl group having 1 to 6 carbon atoms.
オルガノポリシロキサンセグメント（ａ）と、ポリ（N-アシルアルキレンイミン）セグメント（ｂ）との質量比（ａ／ｂ）は83／17〜98／2であるが、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとする観点から、好ましくは85／15〜96／4、更に好ましくは87／13〜90／10である。 The mass ratio (a / b) of the organopolysiloxane segment (a) to the poly (N-acylalkylenimine) segment (b) is 83/17 to 98/2. Preferably from 85/15 to 96/4, more preferably from the viewpoint of having excellent performance of colorability and water resistance of the colored film, difficulty in color transfer, soft touch, and non-stickiness. Is 87/13 to 90/10.
なお、本明細書において、質量比（ａ／ｂ）は、成分(A)のオルガノポリシロキサンを重クロロホルム中に５質量％溶解させ、核磁気共鳴（1H-NMR）分析により、オルガノポリシロキサンセグメント中のアルキル基又はフェニル基と、ポリ（N-アシルアルキレンイミン）セグメント中のメチレン基の積分比より求めた値をいう。 In the present specification, the mass ratio (a / b) is determined by dissolving 5% by mass of the organopolysiloxane of component (A) in deuterated chloroform and analyzing it by nuclear magnetic resonance ( 1 H-NMR) analysis. The value obtained from the integral ratio of the alkyl group or phenyl group in the segment and the methylene group in the poly (N-acylalkylenimine) segment.
また、隣接するポリ（N-アシルアルキレンイミン）セグメント間におけるオルガノポリシロキサンセグメントの重量平均分子量（グラフト点間分子量；ＭＷg）は12,000〜30,000であるが、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとする観点から、好ましくは13,000〜28,000、更に好ましくは15,000〜25,000である。 The weight average molecular weight (molecular weight between graft points; MWg) of the organopolysiloxane segment between adjacent poly (N-acylalkylenimine) segments is 12,000 to 30,000, which is a basic performance of a temporary hair dye composition. From the viewpoint of having excellent colorability, water resistance of the colored film, difficulty in color transfer, soft touch and non-stickiness, it is preferably 13,000 to 28,000, more preferably 15,000 to 25,000.
本明細書において、「隣接するポリ（N-アシルアルキレンイミン）セグメント間におけるオルガノポリシロキサンセグメント」とは、下記式(2)に示すように、ポリ（N-アシルアルキレンイミン）セグメントのオルガノポリシロキサンセグメントに対する結合点（結合点Ａ）から、これに隣接するポリ（N-アシルアルキレンイミン）セグメントの結合点（結合点Ｂ）までの２点間において破線で囲まれた部分であって、１つのＲ2ＳｉＯ単位と、１つのＲ6と、ｙ＋１個のＲ2 2ＳｉＯ単位とから構成されるセグメントをいう。また、「ポリ（N-アシルアルキレンイミン）セグメント」とは、上記Ｒ6に結合するＺをいう。 In the present specification, “an organopolysiloxane segment between adjacent poly (N-acylalkyleneimine) segments” means an organopolysiloxane of a poly (N-acylalkyleneimine) segment as shown in the following formula (2): A portion surrounded by a broken line between two points from a bonding point to the segment (bonding point A) to a bonding point (bonding point B) of the poly (N-acylalkyleneimine) segment adjacent thereto, A segment composed of an R 2 SiO unit, one R 6 , and y + 1 R 2 2 SiO units. The “poly (N-acylalkylenimine) segment” refers to Z bonded to the above R 6 .
上記一般式(2)中、Ｒ2はそれぞれ独立に炭素数１〜22のアルキル基又はフェニル基を示し、Ｒ6はヘテロ原子を含むアルキレン基を示し、Ｚはポリ（N-アシルアルキレンイミン）セグメントを示し、Ｒ7は重合開始剤の残基を示し、ｙは正の数を示す。 In the general formula (2), each R 2 independently represents an alkyl group having 1 to 22 carbon atoms or a phenyl group, R 6 represents an alkylene group containing a hetero atom, and Z represents a poly (N-acylalkyleneimine). Represents a segment, R 7 represents a residue of a polymerization initiator, and y represents a positive number.
ＭＷgは、上記一般式(2)において破線で囲まれた部分の分子量であるが、ポリ（N-アシルアルキレンイミン）セグメント１モル当たりのオルガノポリシロキサンセグメントの質量（g/mol）と解することができ、原料化合物である変性オルガノポリシロキサンの官能基がポリ（N-アシルアルキレンイミン）で100％置換されると、変性オルガノポリシロキサンの官能基当量（g/mol）と一致する。 MWg is the molecular weight of the portion surrounded by the broken line in the above general formula (2), but is understood as the mass (g / mol) of the organopolysiloxane segment per mole of the poly (N-acylalkylenimine) segment. When the functional group of the modified organopolysiloxane, which is a raw material compound, is 100% substituted with poly (N-acylalkyleneimine), it matches the functional group equivalent (g / mol) of the modified organopolysiloxane.
ポリ（N-アシルアルキレンイミン）セグメントの分子量（ＭＷox）は、N-アシルアルキレンイミン単位の分子量と重合度とから算出する方法又は後述するゲルパーミエーションクロマトグラフィー（GPC）測定法により測定することが可能であるが、本発明においてはGPC測定法により測定される数平均分子量をいい、好ましくは800〜4500、更に好ましくは1000〜4000、更に好ましくは2000〜3000である。これにより、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとすることができる。 The molecular weight (MWox) of the poly (N-acylalkylenimine) segment can be measured by a method of calculating from the molecular weight of N-acylalkyleneimine units and the degree of polymerization, or a gel permeation chromatography (GPC) measurement method described later. Although it is possible, in the present invention, it means the number average molecular weight measured by the GPC measurement method, preferably 800 to 4500, more preferably 1000 to 4000, and still more preferably 2000 to 3000. Thereby, it is excellent in the colorability which is the basic performance of a temporary hair dye composition, the water resistance of a coloring film, and the difficulty of a color transfer, and also has a soft touch and non-stickiness.
また、ＭＷgは、主鎖を構成するオルガノポリシロキサンセグメントの含有率（Ｃsi）を用いて下記式により求めることができる。 Further, MWg can be obtained by the following formula using the content (Csi) of the organopolysiloxane segment constituting the main chain.
主鎖を構成するオルガノポリシロキサンセグメントの重量平均分子量（ＭＷsi）は10,000〜200,000であるが、水等の極性溶媒への溶解性と溶解後の取り扱いやすさ、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとする観点から、好ましくは20,000〜180,000、更に好ましくは30,000〜150,000である。ＭＷsiは、原料化合物である変性オルガノポリシロキサンと共通の骨格を有するため、ＭＷsiは原料化合物である変性オルガノポリシロキサンの重量平均分子量と略同一である。なお、原料化合物である変性オルガノポリシロキサンの重量平均分子量は、下記測定条件によるGPCで測定し、ポリスチレン換算したものである。 The weight average molecular weight (MWsi) of the organopolysiloxane segment constituting the main chain is 10,000 to 200,000, but it is soluble in polar solvents such as water, ease of handling after dissolution, and basic performance of the temporary hair dye composition From the standpoint of having excellent colorability and water resistance of the colored film, difficulty in color transfer, soft touch, and non-stickiness, preferably from 20,000 to 180,000, more preferably from 30,000 to 150,000 is there. Since MWsi has a common skeleton with the modified organopolysiloxane that is the raw material compound, MWsi is substantially the same as the weight average molecular weight of the modified organopolysiloxane that is the raw material compound. In addition, the weight average molecular weight of the modified organopolysiloxane which is a raw material compound is measured by GPC under the following measurement conditions and is converted to polystyrene.
カラム ：Super HZ4000＋Super HZ2000（東ソー株式会社製）
溶離液 ：１mMトリエチルアミン/THF
流量 ：0.35mL/min
カラム温度：40℃
検出器 ：UV
サンプル ：50μL
Column: Super HZ4000 + Super HZ2000 (manufactured by Tosoh Corporation)
Eluent: 1 mM triethylamine / THF
Flow rate: 0.35mL / min
Column temperature: 40 ° C
Detector: UV
Sample: 50μL
成分(A)のオルガノポリシロキサンの重量平均分子量（ＭＷt）は、好ましくは12,000〜250,000、より好ましくは30,000〜200,000、更に好ましくは50,000〜150,000である。これにより、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとなり、加えて水等の極性溶媒に対する溶解性が優れたものになる。本明細書において、ＭＷtは、原料化合物である変性オルガノポリシロキサンの重量平均分子量と、前述の質量比（ａ／ｂ）とから求めることができる。 The weight average molecular weight (MWt) of the organopolysiloxane of component (A) is preferably 12,000 to 250,000, more preferably 30,000 to 200,000, and even more preferably 50,000 to 150,000. As a result, the colorability and water resistance of the colored film, which are the basic performance of the temporary hair dye composition, are excellent in resistance to color transfer, and also have a soft feel and non-stickiness, in addition to water, etc. The solubility in a polar solvent is excellent. In the present specification, MWt can be determined from the weight average molecular weight of the modified organopolysiloxane that is a raw material compound and the aforementioned mass ratio (a / b).
成分(A)のオルガノポリシロキサンは、例えば、下記一般式(3)で表される変性オルガノポリシロキサンと、下記一般式(4)で表される環状イミノエーテルを開環重合して得られる末端反応性ポリ（N-アシルアルキレンイミン）とを反応させることにより製造される。 The organopolysiloxane of component (A) is, for example, a terminal obtained by ring-opening polymerization of a modified organopolysiloxane represented by the following general formula (3) and a cyclic imino ether represented by the following general formula (4) It is produced by reacting with a reactive poly (N-acylalkylenimine).
〔式中、Ｒ2は上記と同義であり、Ｒ3、Ｒ4はそれぞれＲ2と同一の基を示すか又は下記式 [Wherein R 2 has the same meaning as above, and R 3 and R 4 each represent the same group as R 2 , or
のいずれかで表される１価の基を示し、Ｒ5は上記式で表される１価の基を示し、ｄは135〜1350の整数を示し、ｅは３〜57の整数を示す。〕 R 5 represents a monovalent group represented by the above formula, d represents an integer of 135 to 1350, and e represents an integer of 3 to 57. ]
〔式中、Ｒ1及びｎは前記と同義である。〕 [Wherein, R 1 and n are as defined above. ]
変性オルガノポリシロキサンは、官能基当量が好ましくは10,000〜30,000、より好ましくは12,000〜28,000、特に好ましくは13,000〜25,000である。重量平均分子量は、前述の主鎖を構成するオルガノポリシロキサンセグメントの重量平均分子量（ＭＷsi）と略同一である。 The modified organopolysiloxane preferably has a functional group equivalent of 10,000 to 30,000, more preferably 12,000 to 28,000, and particularly preferably 13,000 to 25,000. The weight average molecular weight is substantially the same as the weight average molecular weight (MWsi) of the organopolysiloxane segment constituting the main chain.
環状イミノエーテル(4)の開環重合には、重合開始剤を用いることができる。重合開始剤としては、求電子反応性の強い化合物、例えば、ベンゼンスルホン酸アルキルエステル、p-トルエンスルホン酸アルキルエステル、トリフルオロメタンスルホン酸アルキルエステル、トリフルオロ酢酸アルキルエステル、硫酸ジアルキルエステル等の強酸のアルキルエステルを使用することができ、中でも硫酸ジアルキルが好適に使用される。重合開始剤の使用量は、通常、環状イミノエーテル(4)２〜100モルに対して、重合開始剤１モルである。 A polymerization initiator can be used for the ring-opening polymerization of the cyclic imino ether (4). As the polymerization initiator, a compound having strong electrophilic reactivity, for example, a strong acid such as benzenesulfonic acid alkyl ester, p-toluenesulfonic acid alkyl ester, trifluoromethanesulfonic acid alkyl ester, trifluoroacetic acid alkyl ester, sulfuric acid dialkyl ester, etc. Alkyl esters can be used, and among them, dialkyl sulfate is preferably used. The amount of the polymerization initiator used is usually 1 mol of the polymerization initiator with respect to 2 to 100 mol of the cyclic imino ether (4).
重合溶媒としては、例えば、酢酸エチル、酢酸プロピル等の酢酸エステル類、ジエチルエーテル、ジイソプロピルエーテル、ジオキサン、テトラヒドロフラン等のエーテル類、アセトン、メチルエチルケトン等のケトン類、クロロホルム、塩化メチレン等のハロゲン溶媒、アセトニトリル、ベンゾニトリル等のニトリル系溶媒、N,N-ジメチルフォルムアミド、N,N-ジメチルアセトアミド、ジメチルスルフォキシド等の非プロトン性極性溶媒を使用することができ、中でも酢酸エステル類が好適に使用される。溶媒の使用量は、通常、環状イミノエーテル(4)100質量部に対して20〜2000質量部である。 Examples of the polymerization solvent include acetates such as ethyl acetate and propyl acetate, ethers such as diethyl ether, diisopropyl ether, dioxane and tetrahydrofuran, ketones such as acetone and methyl ethyl ketone, halogen solvents such as chloroform and methylene chloride, acetonitrile. , Nitrile solvents such as benzonitrile, aprotic polar solvents such as N, N-dimethylformamide, N, N-dimethylacetamide, dimethyl sulfoxide, etc., among which acetates are preferred Is done. The amount of the solvent used is usually 20 to 2000 parts by mass with respect to 100 parts by mass of the cyclic imino ether (4).
重合温度は通常30〜170℃、好ましくは40〜150℃であり、重合時間は重合温度等により一様ではないが、通常１〜60時間である。 The polymerization temperature is usually 30 to 170 ° C., preferably 40 to 150 ° C., and the polymerization time is usually 1 to 60 hours, although it is not uniform depending on the polymerization temperature and the like.
環状イミノエーテル(4)として、例えば、2-置換-2-オキサゾリンを用いれば、前記一般式(1)において、ｎ＝２のポリ（N-アシルエチレンイミン）が得られ、2-置換−ジヒドロ-2-オキサジンを用いれば、上記一般式(1)において、ｎ＝３のポリ（N-アシルプロピレンイミン）が得られる。 When, for example, 2-substituted-2-oxazoline is used as the cyclic imino ether (4), a poly (N-acylethyleneimine) of n = 2 in the general formula (1) is obtained, and 2-substituted-dihydro When 2-oxazine is used, poly (N-acylpropyleneimine) having n = 3 in the general formula (1) can be obtained.
ポリ（N-アシルアルキレンイミン）と、オルガノポリシロキサンセグメントとの連結方法としては、例えば、下記の方法が挙げられる。
１）環状イミノエーテルをリビング重合して得られる末端反応性ポリ（N-アシルアルキレンイミン）に、上記一般式(3)で表される変性オルガノポリシロキサンを反応させる方法
２）カルボキシル基と水酸基との縮合によるエステルの形成反応
３）カルボキシル基とアミノ基との縮合によるアミドの形成反応
４）ハロゲン化アルキル基と、１級、２級又は３級アミノ基との２級、３級又は４級アンモニウムの形成反応
５）Ｓｉ−Ｈ基を有するオルガノポリシロキサンへのビニル基の付加反応
６）エポキシ基とアミノ基とのβ−ヒドロキシアミン形成反応
Examples of a method for connecting poly (N-acylalkylenimine) and the organopolysiloxane segment include the following methods.
1) A method of reacting a terminally reactive poly (N-acylalkyleneimine) obtained by living polymerization of a cyclic imino ether with a modified organopolysiloxane represented by the above general formula (3) 2) A carboxyl group and a hydroxyl group 3) Formation of ester by condensation of carboxyl group and amino group 4) Formation of amide by condensation of carboxyl group and amino group 4) Secondary, tertiary or quaternary of alkyl halide group with primary, secondary or tertiary amino group Formation reaction of ammonium 5) Addition reaction of vinyl group to organopolysiloxane having Si-H group 6) Formation reaction of β-hydroxyamine between epoxy group and amino group
中でも、上記１）の方法は、下に示す理論式（式中、ＭＷiはポリ(N-アシルアルキレンイミン)の分子量）のように、環状イミノエーテル(4)と重合開始剤の使用量で重合度を容易に制御でき、しかも通常のラジカル重合よりも分子量分布の狭い略単分散のポリ（N-アシルアルキレンイミン）が得られる点で最も有効である。 In particular, the above method 1) is polymerized by using the cyclic imino ether (4) and the polymerization initiator as shown in the following theoretical formula (where MWi is the molecular weight of poly (N-acylalkyleneimine)). It is most effective in that a substantially monodispersed poly (N-acylalkylenimine) having a molecular weight distribution narrower than that of normal radical polymerization can be obtained.
成分(A)のオルガノポリシロキサンとしては、ポリ（N-ホルミルエチレンイミン）オルガノシロキサン、ポリ（N-アセチルエチレンイミン）オルガノシロキサン、ポリ（N-プロピオニルエチレンイミン）オルガノシロキサン等が挙げられる。 Examples of the component (A) organopolysiloxane include poly (N-formylethyleneimine) organosiloxane, poly (N-acetylethyleneimine) organosiloxane, and poly (N-propionylethyleneimine) organosiloxane.
成分(A)のオルガノポリシロキサンは単独で又は２種以上を組み合わせて用いることができ、その含有量は、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとする観点から、全組成中（エアゾール式の場合、噴射剤を含まない原液の全組成中。以下同じ）の３〜20質量％、更には４〜18質量％、特に５〜16質量％が好ましい。 The organopolysiloxane of component (A) can be used alone or in combination of two or more, and its content is the basic performance of the temporary hair dye composition, the water resistance of the colored film, the color transfer From the viewpoint of having a soft feel and non-stickiness in addition to being excellent in the difficulty of being treated, 3 to 3 in the whole composition (in the case of an aerosol type, in the whole composition of the stock solution containing no propellant, the same applies hereinafter) 3 20 mass%, further 4-18 mass%, especially 5-16 mass% are preferable.
〔(B)：顔料及び／又は直接染料〕
成分(B)において顔料及び／又は直接染料は、成分(A)と組み合わせて用いることにより、頭髪に顔料及び／又は直接染料を含む皮膜を形成し、頭髪表面を着色被覆するために配合されるものであり、化粧料に一般に用いられるものであれば特に制限はない。
[(B): Pigment and / or direct dye]
In the component (B), the pigment and / or the direct dye are used in combination with the component (A) to form a film containing the pigment and / or the direct dye on the hair and color-coat the hair surface. If it is a thing and is generally used for cosmetics, there will be no restriction | limiting in particular.
顔料としては、その形状（球状、針状、板状等）や粒子径、粒子構造（多孔質、無孔質等）を問わず、いずれのものも使用することができ、例えば無機顔料、有機顔料、パール顔料、金属粉末顔料、光輝性粉体等が挙げられる。
無機顔料としては、具体的には、カーボンブラック、黒酸化鉄、黒酸化チタン等の無機黒色系顔料；酸化鉄（べんがら）、水酸化鉄、チタン酸鉄等の無機赤色系顔料；γ−酸化鉄等の無機褐色系顔料；黄酸化鉄、黄土等の無機黄色系顔料；群青、紺青等の無機青色系顔料；マンガンバイオレット、コバルトバイオレット等の無機紫色系顔料；酸化クロム、水酸化クロム、チタン酸コバルト等の無機緑色系顔料；酸化チタン、酸化亜鉛、酸化セリウム等の無機白色系顔料等が挙げられる。これらのうち、カーボンブラック、黒酸化鉄、黒酸化チタン、酸化鉄（べんがら）、黄酸化鉄、群青、紺青が好ましい。
Any pigment can be used regardless of its shape (spherical, needle, plate, etc.), particle diameter, particle structure (porous, nonporous, etc.), such as inorganic pigments, organic Examples thereof include pigments, pearl pigments, metal powder pigments, and glittering powders.
Specific examples of inorganic pigments include inorganic black pigments such as carbon black, black iron oxide, and black titanium oxide; inorganic red pigments such as iron oxide, iron hydroxide, and iron titanate; γ-oxidation Inorganic brown pigments such as iron; Inorganic yellow pigments such as yellow iron oxide and ocher; Inorganic blue pigments such as ultramarine and bitumen; Inorganic purple pigments such as manganese violet and cobalt violet; Chromium oxide, chromium hydroxide and titanium Inorganic green pigments such as cobalt oxide; inorganic white pigments such as titanium oxide, zinc oxide and cerium oxide. Of these, carbon black, black iron oxide, black titanium oxide, iron oxide (bengal), yellow iron oxide, ultramarine blue, and bitumen are preferable.
有機顔料としては、赤色201号、赤色202号、赤色203号、赤色204号、赤色205号、赤色206号、赤色207号、赤色208号、赤色219号、赤色220号、赤色221号、赤色228号、赤色404号、赤色405号、だいだい色203号、だいだい色204号、だいだい色401号、黄色205号、黄色401号、青色404号等が挙げられ、このうち、赤色202号、赤色404号、黄色205号、黄色401号、青色404号が好ましい。 Organic pigments include red 201, red 202, red 203, red 204, red 205, red 206, red 207, red 208, red 219, red 220, red 221 and red 228, red 404, red 405, orange 203, orange 204, orange 401, yellow 205, yellow 401, blue 404, etc., of which red 202, red 404, Yellow 205, Yellow 401 and Blue 404 are preferred.
パール顔料としては、パール粉末、オキシ塩化ビスマス、雲母、金属酸化物被覆雲母（例えば、雲母チタン、酸化鉄被覆雲母、酸化鉄被覆雲母チタン、黒酸化鉄被覆雲母、黒酸化鉄被覆雲母チタン、黄酸化鉄被覆雲母、酸化鉄・黒酸化鉄被覆雲母チタン、紺青被覆雲母チタン、酸化鉄・紺青被覆雲母チタン、カルミン被覆雲母チタン、硫酸バリウム被覆雲母チタンなど）、金属酸化物被覆アルミナフレーク、金属酸化物被覆シリカフレーク、多層コートパール顔料（例えば、TiO2-SiO2-TiO2-Mica等）等が挙げられる。
金属粉末顔料としては、金粉、銀粉、銅粉、アルミニウム粉、真鍮粉等が挙げられる。
光輝性粉体としては、ポリエチレンテレフタレート・アルミニウム・エポキシ積層体、ポリエチレンテレフタレート・ポリオレフィン積層フィルム体等が挙げられる。
Examples of the pearl pigment include pearl powder, bismuth oxychloride, mica, metal oxide-coated mica (for example, mica titanium, iron oxide-coated mica, iron oxide-coated mica titanium, black iron oxide-coated mica, black iron oxide-coated mica titanium, yellow Iron oxide coated mica, iron oxide / black iron oxide coated mica titanium, bitumen coated mica titanium, iron oxide / bitumen coated mica titanium, carmine coated mica titanium, barium sulfate coated mica titanium, etc.), metal oxide coated alumina flakes, metal oxide Product-coated silica flakes, multilayer coated pearl pigments (for example, TiO 2 —SiO 2 —TiO 2 —Mica) and the like.
Examples of the metal powder pigment include gold powder, silver powder, copper powder, aluminum powder, and brass powder.
Examples of the glitter powder include polyethylene terephthalate / aluminum / epoxy laminate, polyethylene terephthalate / polyolefin laminate film, and the like.
顔料は、単独で又は２種以上を組み合わせて用いることができ、その含有量は、着色性、色移りのしにくさ、塗布後の感触と塗布しやすさの点から、全組成中の0.01〜30質量％、更に0.1〜25質量％、特に１〜20質量％が好ましい。 The pigments can be used alone or in combination of two or more, and the content thereof is 0.01% in the total composition from the viewpoints of colorability, resistance to color transfer, feel after application, and ease of application. -30% by mass, more preferably 0.1-25% by mass, especially 1-20% by mass.
成分(B)として直接染料を用いると、直接染料の一部が頭髪内部に浸透するため、繰り返し使用することで頭髪を少しずつ染めていく徐染型一時染毛料とすることができる。直接染料としては、染毛剤に利用可能である公知の酸性染料、塩基性染料、分散染料、反応性染料等を用いることができる。酸性染料としては、例えば青色１号、青色２号、青色202号、青色203号、紫色401号、黒色401号、だいだい色205号、だいだい色207号、だいだい色402号、赤色３号、赤色102号、赤色104号、赤色105号、赤色106号、赤色225号、赤色227号、赤色502号、黄色４号、黄色５号、黄色202号、黄色203号、黄色402号、緑色３号、緑色204号、緑色205号、かっ色201号、酸性橙３等が挙げられる。塩基性染料としては、例えば塩基性青99、塩基性茶16、塩基性茶17、塩基性赤76、塩基性黄57等が挙げられる。酸性染料及び塩基性染料以外の直接染料としては、例えば2-ニトロ-p-フェニレンジアミン、2-アミノ-6-クロロ-4-ニトロフェノール、3-ニトロ-p-ヒドロキシエチルアミノフェノール、4-ニトロ-o-フェニレンジアミン、4-アミノ-3-ニトロフェノール、４−ヒドロキシプロピルアミノ-3-ニトロフェノール、N,N-ビス-(2-ヒドロキシエチル)-2-ニトロ-p-フェニレンジアミン、分散紫１、分散青１、分散黒９、HC青２、HC橙１、HC赤１、HC赤３、HC黄２、HC黄４、HC黄５等が挙げられる。 When a direct dye is used as the component (B), a part of the direct dye penetrates into the hair, so that it can be used as a gradual dyeing type temporary hair dye that gradually dyes the hair by repeated use. As the direct dye, known acidic dyes, basic dyes, disperse dyes, reactive dyes and the like that can be used for hair dyes can be used. Examples of acid dyes include Blue No. 1, Blue No. 2, Blue No. 202, Blue No. 203, Purple No. 401, Black No. 401, Dai No. 205, Dai No. 207, Dai No. 402, Red No. 3, Red 102, Red 104, Red 105, Red 106, Red 225, Red 227, Red 502, Yellow 4, Yellow 5, Yellow 202, Yellow 203, Yellow 402, Green 3 Green 204, green 205, brown 201, acidic orange 3, and the like. Examples of the basic dye include basic blue 99, basic brown 16, basic brown 17, basic red 76, basic yellow 57, and the like. Examples of direct dyes other than acid dyes and basic dyes include 2-nitro-p-phenylenediamine, 2-amino-6-chloro-4-nitrophenol, 3-nitro-p-hydroxyethylaminophenol, and 4-nitro. -o-phenylenediamine, 4-amino-3-nitrophenol, 4-hydroxypropylamino-3-nitrophenol, N, N-bis- (2-hydroxyethyl) -2-nitro-p-phenylenediamine, dispersed purple 1, dispersion blue 1, dispersion black 9, HC blue 2, HC orange 1, HC red 1, HC red 3, HC yellow 2, HC yellow 4, HC yellow 5, and the like.
直接染料は、単独で又は２種以上を組み合わせて用いることができ、その含有量は、着色性、、色移りのしにくさ、塗布後の感触と塗布しやすさの点から、全組成中の0.01〜５質量％、更に0.05〜３質量％、特に0.1〜１質量％が好ましい。 Direct dyes can be used singly or in combination of two or more, and their content is in the total composition from the viewpoints of colorability, resistance to color transfer, feel after application and ease of application. 0.01 to 5% by mass, more preferably 0.05 to 3% by mass, and particularly preferably 0.1 to 1% by mass.
また、成分(A)のオルガノポリシロキサンと成分(B)の含量との質量比(A)／(B)は、一時染毛剤組成物の基本性能である着色性と着色皮膜の耐水性、色移りのし難さに優れるほか、やわらかな感触、べたつきのなさを兼ね備えたものとする観点より、0.1〜2000が好ましく、更には0.5〜200、特に１〜20が好ましい。 Further, the mass ratio (A) / (B) between the organopolysiloxane of component (A) and the content of component (B) is the basic performance of the temporary hair dye composition and the water resistance of the colored film, From the viewpoint of being excellent in the difficulty of color transfer and having a soft touch and non-stickiness, 0.1 to 2000 is preferable, 0.5 to 200, and particularly 1 to 20 is preferable.
〔(C)：カチオン性基含有共重合体〕
本発明の一時染毛剤組成物には、更に成分(C)として、一般式(I)又は(II)で表される親水性ノニオン性基含有ビニル単量体の少なくとも１種と、一般式(III)又は(IV)で表されるカチオン性基含有ビニル単量体の少なくとも１種と、ビニル基、アクリロイル基、メタクリロイル基及びアリル基から選ばれる少なくとも２個の基を分子中に有する架橋性ビニル単量体の少なくとも１種とを必須構成単量体とし、ラジカル重合することにより得られる、カチオン性基含有共重合体を含有させることができる。このカチオン性基含有共重合体は、優れた増粘性を有するため、本発明の一時染毛剤組成物がヘアマスカラ剤である場合に、特に好適である。
[(C): cationic group-containing copolymer]
The temporary hair dye composition of the present invention further includes, as component (C), at least one hydrophilic nonionic group-containing vinyl monomer represented by general formula (I) or (II), and a general formula Crosslink having at least one of the cationic group-containing vinyl monomers represented by (III) or (IV) and at least two groups selected from vinyl group, acryloyl group, methacryloyl group and allyl group in the molecule A cationic group-containing copolymer obtained by radical polymerization using at least one kind of a functional vinyl monomer as an essential constituent monomer can be contained. Since this cationic group-containing copolymer has excellent thickening properties, it is particularly suitable when the temporary hair dye composition of the present invention is a hair mascara agent.
〔式中、Ｒ11は水素原子又はメチル基を示し、Ｒ12及びＲ13は同一又は異なって、水素原子又は炭素数１〜４の直鎖状若しくは分岐状のアルキル基又はアルケニル基を示す。〕 [Wherein, R 11 represents a hydrogen atom or a methyl group, and R 12 and R 13 are the same or different and represent a hydrogen atom or a linear or branched alkyl group or alkenyl group having 1 to 4 carbon atoms. ]
〔式中、Ｒ11は前記の意味を示し、Ａ1及びＡ2は同一又は異なって、炭素数２〜６のポリメチレン基を示し、Ｂは酸素原子又はメチレン基を示す。〕 [Wherein R 11 represents the above-mentioned meaning, A 1 and A 2 are the same or different and represent a polymethylene group having 2 to 6 carbon atoms, and B represents an oxygen atom or a methylene group. ]
〔式中、Ｒ11は前記の意味を示し、Ｒ14及びＲ15は同一又は異なって、炭素数１〜４のアルキル基又はアルケニル基を示し、Ｒ16は水素原子又は炭素数１〜４のアルキル基を示し、Ｙは−O−、−NH−又は−O−CH2CH(OH)−基を示し、Ａ3は炭素数１〜４の直鎖状又は分岐状の２価飽和炭化水素基を示し、Ｘは酸の共役塩基、ハロゲン原子又は炭素数１〜４のアルキルサルフェートを示す。〕 [Wherein R 11 represents the above-mentioned meaning, R 14 and R 15 are the same or different and represent an alkyl group or alkenyl group having 1 to 4 carbon atoms, and R 16 represents a hydrogen atom or 1 to 4 carbon atoms. Represents an alkyl group, Y represents an —O—, —NH— or —O—CH 2 CH (OH) — group, and A 3 represents a linear or branched divalent saturated hydrocarbon having 1 to 4 carbon atoms. And X represents an acid conjugate base, a halogen atom or an alkyl sulfate having 1 to 4 carbon atoms. ]
〔式中、Ｒ17及びＲ18は同一又は異なって水素原子又はメチル基を示し、Ｒ19及びＲ20は同一又は異なって水素原子又は炭素数１〜４のアルキル基を示し、Ｘは前記の意味を示す。〕 [Wherein, R 17 and R 18 are the same or different and each represents a hydrogen atom or a methyl group; R 19 and R 20 are the same or different and each represent a hydrogen atom or an alkyl group having 1 to 4 carbon atoms; Indicates meaning. ]
・親水性ノニオン性基含有ビニル単量体
成分(C)のカチオン性基含有共重合体を構成する単量体のうち、前記一般式(Ｉ)で表される親水性ノニオン性基含有ビニル単量体としては、（メタ）アクリルアミド、N-メチル（メタ）アクリルアミド、N,N-ジメチル（メタ）アクリルアミド、N,N-ジエチル（メタ）アクリルアミド、N-n-プロピル（メタ）アクリルアミド、N-イソプロピル（メタ）アクリルアミド、N-t-ブチル（メタ）アクリルアミド、N-イソブチル（メタ）アクリルアミド等が挙げられる。
また一般式(II)で表される親水性ノニオン性基含有ビニル単量体としては、N-（メタ）アクロイルモルホリンなどが挙げられる。
これらの親水性ノニオン性基含有ビニル単量体は、単独で又は２種以上を混合して用いることができる。
Hydrophilic nonionic group-containing vinyl monomer Among the monomers constituting the cationic group-containing copolymer of component (C), the hydrophilic nonionic group-containing vinyl monomer represented by the general formula (I) As the polymer, (meth) acrylamide, N-methyl (meth) acrylamide, N, N-dimethyl (meth) acrylamide, N, N-diethyl (meth) acrylamide, Nn-propyl (meth) acrylamide, N-isopropyl ( Examples include meth) acrylamide, Nt-butyl (meth) acrylamide, N-isobutyl (meth) acrylamide and the like.
Examples of the hydrophilic nonionic group-containing vinyl monomer represented by the general formula (II) include N- (meth) acryloylmorpholine.
These hydrophilic nonionic group-containing vinyl monomers can be used alone or in admixture of two or more.
これらの親水性ノニオン性基含有ビニル単量体の中では、N,N-ジ置換アクリルアミドを用いた場合に使用感的に特に好ましく、更にはN,N-ジメチル（メタ）アクリルアミド、N,N-ジエチル（メタ）アクリルアミドが、エタノール水溶液やアニオン界面活性剤水溶液をもゲル化できるため、応用範囲が広く好ましい。 Among these hydrophilic nonionic group-containing vinyl monomers, N, N-disubstituted acrylamide is particularly preferable in terms of usability, and N, N-dimethyl (meth) acrylamide, N, N -Diethyl (meth) acrylamide is preferable because it can gel an aqueous ethanol solution and an aqueous anionic surfactant solution.
・カチオン性基含有ビニル単量体
成分(C)のカチオン性基含有共重合体を構成する単量体のうち、前記一般式(III)で表されるカチオン性基含有ビニル単量体の具体例としては、ジメチルアミノエチル（メタ）アクリレート、ジエチルアミノエチル（メタ）アクリレート、ジプロピルアミノエチル（メタ）アクリレート、ジイソプロピルアミノエチル（メタ）アクリレート、ジブチルアミノエチル（メタ）アクリレート、ジイソブチルアミノエチル（メタ）アクリレート、ジt-ブチルアミノエチル（メタ）アクリレート、ジメチルアミノプロピル（メタ）アクリルアミド、ジエチルアミノプロピル（メタ）アクリルアミド、ジプロピルアミノプロピル（メタ）アクリルアミド、ジイソプロピルアミノプロピル（メタ）アクリルアミド、ジブチルアミノプロピル（メタ）アクリルアミド、ジイソブチルアミノプロピル（メタ）アクリルアミド、ジt-ブチルアミノプロピル（メタ）アクリルアミド等のジアルキルアミノ基を有する（メタ）アクリル酸エステル又は（メタ）アクリルアミド類を酸で中和した酸中和物あるいは４級化剤で４級化した４級アンモニウム塩が挙げられる。上記の酸中和物を得るための好ましい酸としては、塩酸、硫酸、硝酸、酢酸、ギ酸、マレイン酸、フマル酸、クエン酸、酒石酸、アジピン酸、スルファミン酸、トルエンスルホン酸、乳酸、ピロリドン-2-カルボン酸、コハク酸などが挙げられ、また上記４級アンモニウム塩を得るための好ましい４級化剤としては、塩化メチル、塩化エチル、臭化メチル、ヨウ化メチル等のハロゲン化アルキル、硫酸ジメチル、硫酸ジエチル、硫酸ジ-n-プロピル等の一般的なアルキル化剤が挙げられる。
また一般式(IV)で表されるカチオン性基含有ビニル単量体の具体例としては、ジメチルジアリルアンモニウムクロライド、ジエチルジアリルアンモニウムクロライド等のジアリル型４級アンモニウム塩が挙げられる。
これらのカチオン性基含有ビニル単量体は、単独で又は２種以上を混合して用いることができる。
-Cationic group-containing vinyl monomer Among the monomers constituting the cationic group-containing copolymer of component (C), specific examples of the cationic group-containing vinyl monomer represented by the general formula (III) Examples include dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dipropylaminoethyl (meth) acrylate, diisopropylaminoethyl (meth) acrylate, dibutylaminoethyl (meth) acrylate, diisobutylaminoethyl (meth) Acrylate, di-t-butylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylamide, diethylaminopropyl (meth) acrylamide, dipropylaminopropyl (meth) acrylamide, diisopropylaminopropyl (meth) acrylamide, dibutyl acrylate Acids obtained by neutralizing (meth) acrylic acid esters or (meth) acrylamides having a dialkylamino group such as nopropyl (meth) acrylamide, diisobutylaminopropyl (meth) acrylamide, di-t-butylaminopropyl (meth) acrylamide, etc. with an acid A quaternary ammonium salt quaternized with a neutralized product or a quaternizing agent can be mentioned. Preferred acids for obtaining the acid neutralized product include hydrochloric acid, sulfuric acid, nitric acid, acetic acid, formic acid, maleic acid, fumaric acid, citric acid, tartaric acid, adipic acid, sulfamic acid, toluenesulfonic acid, lactic acid, pyrrolidone- Preferred examples of the quaternizing agent for obtaining the quaternary ammonium salt include alkyl halides such as methyl chloride, ethyl chloride, methyl bromide and methyl iodide, sulfuric acid, and the like. Common alkylating agents such as dimethyl, diethyl sulfate, di-n-propyl sulfate and the like can be mentioned.
Specific examples of the cationic group-containing vinyl monomer represented by the general formula (IV) include diallyl-type quaternary ammonium salts such as dimethyldiallylammonium chloride and diethyldiallylammonium chloride.
These cationic group-containing vinyl monomers can be used alone or in admixture of two or more.
これらのカチオン性基含有ビニル単量体の中でより好ましいものとしては、ジメチルアミノエチル（メタ）アクリレート、ジエチルアミノエチル（メタ）アクリレート、ジメチルアミノプロピル（メタ）アクリルアミド、ジエチルアミノプロピル（メタ）アクリルアミドを前記の４級化剤で４級化した４級アンモニウム塩、あるいはジメチルジアリルアンモニウムクロライドが挙げられる。ここで酸中和物モノマーは、系のpHなどにより中和した酸の解離が起こり、ポリマー構造が変化するため、粘度の安定性が低いという欠点を有する。この点からも４級アンモニウム塩型モノマーがより好ましい。 Among these cationic group-containing vinyl monomers, more preferable examples include dimethylaminoethyl (meth) acrylate, diethylaminoethyl (meth) acrylate, dimethylaminopropyl (meth) acrylamide, and diethylaminopropyl (meth) acrylamide. A quaternary ammonium salt quaternized with a quaternizing agent, or dimethyldiallylammonium chloride. Here, the acid neutralized monomer has a disadvantage that the stability of the viscosity is low because dissociation of the neutralized acid occurs due to the pH of the system and the polymer structure is changed. From this point, a quaternary ammonium salt monomer is more preferable.
・少なくとも２個のビニル基を分子中に有する架橋性ビニル単量体
成分(C)のカチオン性基含有共重合体を構成する単量体のうち、少なくとも２個のビニル基を分子中に有する架橋性ビニル単量体としては、エチレングリコールジ（メタ）アクリレート、ジエチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、プロピレングリコールジ（メタ）アクリレート、ジプロピレングリコールジ（メタ）アクリレート、ポリプロピレングリコールジ（メタ）アクリレート、1,2−ブチレングリコールジ（メタ）アクリレート、1,3−ブチレングリコールジ（メタ）アクリレート、ネオペンチルグリコールジ（メタ）アクリレート、グリセリンジ（メタ）アクリレート、グリセリントリ（メタ）アクリレート、トリメチロールプロパントリ（メタ）アクリレート、ペンタエリスリトールテトラ（メタ）アクリレート等の多価アルコールの（メタ）アクリル酸エステル類；N-メチルアリルアクリルアミド、N-ビニルアクリルアミド、N,N'-メチレンビス（メタ）アクリルアミド、ビスアクリルアミド酢酸等のアクリルアミド類；ジビニルベンゼン、ジビニルエーテル、ジビニルエチレン尿素等のジビニル化合物；ジアリルフタレート、ジアリルマレート、ジアリルアミン、トリアリルアミン、トリアリルアンモニウム塩、ペンタエリスリトールのアリルエーテル化体、分子中に少なくとも２個のアリルエーテル単位を有するスクローゼのアリルエーテル化体等のポリアリル化合物；ビニル（メタ）アクリレート、アリル（メタ）アクリレート、2-ヒドロキシ-3-アクリロイルオキシプロピル（メタ）アクリレート等の不飽和アルコールの（メタ）アクリル酸エステルなどが挙げられる。
・ Crosslinkable vinyl monomer having at least two vinyl groups in the molecule Among the monomers constituting the cationic group-containing copolymer of component (C), it has at least two vinyl groups in the molecule. Crosslinkable vinyl monomers include ethylene glycol di (meth) acrylate, diethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, propylene glycol di (meth) acrylate, dipropylene glycol di (meth) acrylate, polypropylene Glycol di (meth) acrylate, 1,2-butylene glycol di (meth) acrylate, 1,3-butylene glycol di (meth) acrylate, neopentyl glycol di (meth) acrylate, glycerin di (meth) acrylate, glycerin tri ( (Meth) acrylate, tri (Meth) acrylic acid esters of polyhydric alcohols such as methylolpropane tri (meth) acrylate and pentaerythritol tetra (meth) acrylate; N-methylallylacrylamide, N-vinylacrylamide, N, N'-methylenebis (meth) acrylamide Acrylamides such as bisacrylamide acetic acid; divinyl compounds such as divinylbenzene, divinyl ether, divinylethyleneurea; diallyl phthalate, diallyl malate, diallylamine, triallylamine, triallyl ammonium salt, allyl etherified pentaerythritol A polyallyl compound such as an allyl etherified product of sucrose having at least two allyl ether units; vinyl (meth) acrylate, allyl (meth) acrylate, 2-hydroxy-3-acrylate Such Leroy oxy propyl (meth) acrylate unsaturated (meth) acrylic acid ester of an alcohol and the like.
これらの架橋性ビニル単量体の中では、エチレングリコールジ（メタ）アクリレート、ポリエチレングリコールジ（メタ）アクリレート、ジビニルベンゼン、ペンタエリスリトールトリアリルエーテル、ペンタエリスリトールテトラアリルエーテルが好ましい。 Among these crosslinkable vinyl monomers, ethylene glycol di (meth) acrylate, polyethylene glycol di (meth) acrylate, divinylbenzene, pentaerythritol triallyl ether, and pentaerythritol tetraallyl ether are preferable.
・単量体成分の配合割合
成分(C)のカチオン性基含有共重合体を得るために好ましいカチオン性基含有ビニル単量体と親水性ノニオン性基含有ビニル単量体との配合比率は、カチオン性基含有ビニル単量体／親水性ノニオン性基含有ビニル単量体（モル比）で、98／２〜２／98であり、更に好ましくは60／40〜３／97である。これらの単量体の配合比率がここに示した範囲を逸脱した場合、例えばカチオン性基含有ビニル単量体の配合比率が、ここに示した範囲より過剰になった場合には、チキソトロピー性に欠ける傾向となる。また親水性ノニオン性基含有ビニル単量体の配合比率が、ここに示した範囲より過剰になった場合には、低シェアレート時の粘度が低くなりやすい傾向となる。
Mixing ratio of monomer component The mixing ratio of the cationic group-containing vinyl monomer and the hydrophilic nonionic group-containing vinyl monomer preferable for obtaining the cationic group-containing copolymer of component (C) is: Cationic group-containing vinyl monomer / hydrophilic nonionic group-containing vinyl monomer (molar ratio), which is 98/2 to 2/98, more preferably 60/40 to 3/97. When the blending ratio of these monomers deviates from the range shown here, for example, when the blending ratio of the cationic group-containing vinyl monomer exceeds the range shown here, the thixotropy is improved. It tends to lack. Further, when the blending ratio of the hydrophilic nonionic group-containing vinyl monomer is excessive from the range shown here, the viscosity at the time of low shear rate tends to be lowered.
また、成分(C)のカチオン性基含有共重合体を構成する単量体中の少なくとも２個のビニル基を分子中に有する架橋性ビニル単量体の割合は、単量体全量に対して0.002〜５質量％が好ましく、0.002質量％以上0.1質量％未満が特に好ましい。かかる少なくとも２個のビニル基を分子中に有する架橋性ビニル単量体の割合が0.002質量％未満である場合には、得られるカチオン性基含有共重合体の架橋度が小さくなりすぎるため、該カチオン性基含有共重合体から形成されるハイドロゲルの粘度を高くすることができなくなり、また５質量％を超える場合には、ハイドロゲルを手にとって触った時の感触が硬く、すべりの悪いものが得られやすくなる。 The proportion of the crosslinkable vinyl monomer having in the molecule at least two vinyl groups in the monomer constituting the cationic group-containing copolymer of component (C) is based on the total amount of monomers. 0.002-5 mass% is preferable and 0.002 mass% or more and less than 0.1 mass% are especially preferable. When the ratio of the crosslinkable vinyl monomer having at least two vinyl groups in the molecule is less than 0.002% by mass, the degree of crosslinking of the resulting cationic group-containing copolymer becomes too small. The hydrogel formed from the cationic group-containing copolymer cannot be increased in viscosity, and when it exceeds 5% by mass, it feels hard when the hydrogel is touched by the hand, and the slippage is poor. Becomes easier to obtain.
・他の単量体成分
成分(C)のカチオン性基含有共重合体は、前記の３種類のビニル単量体を必須構成成分とする共重合体であるが、これらビニル単量体と共重合可能な他のビニル単量体も構成成分とすることができる。
-Other monomer components The cationic group-containing copolymer of component (C) is a copolymer comprising the above three types of vinyl monomers as essential constituent components. Other vinyl monomers that can be polymerized can also be a constituent.
他のビニル単量体としては、たとえばメチル（メタ）アクリレート、エチル（メタ）アクリレート、n-プロピル（メタ）アクリレート、イソプロピル（メタ）アクリレート、n-ブチル（メタ）アクリレート、イソブチル（メタ）アクリレート、t-ブチル（メタ）アクリレート、n-ペンチル（メタ）アクリレート、ネオペンチル（メタ）アクリレート、シクロペンチル（メタ）アクリレート、n-ヘキシル（メタ）アクリレート、シクロヘキシル（メタ）アクリレート、n-オクチル（メタ）アクリレート、イソオクチル（メタ）アクリレート、2-エチルヘキシル（メタ）アクリレート、n-デシル（メタ）アクリレート、イソデシル（メタ）アクリレート、ラウリル（メタ）アクリレート、トリデシル（メタ）アクリレート、ステアリル（メタ）アクリレート、イソステアリル（メタ）アクリレート、ベヘニル（メタ）アクリレート、フェニル（メタ）アクリレート、トルイル（メタ）アクリレート、キシリル（メタ）アクリレート、ベンジル（メタ）アクリレート、2-エトキシエチル（メタ）アクリレート、2-ブトキシエチル（メタ）アクリレート、2-フェノキシ（メタ）アクリレート、2-メトキシプロピル（メタ）アクリレート、3-メトキシプロピル（メタ）アクリレート、2-エトキシプロピル（メタ）アクリレート、3-エトキシプロピル（メタ）アクリレートなどの（メタ）アクリル酸誘導体；2-アクリルアミド-2-メチルプロパンスルホン酸、スチレンスルホン酸ナトリウム、アクリル酸、メタアクリル酸、2-スルホエチルメタクリレートなどのアニオン性基含有単量体；N-(3-スルホプロピル)-N-アクリロイルオキシエチル-N,N-ジメチルアンモニウムベタイン、N-(3-スルホプロピル)-N-メタクリロイルアミドプロピル-N,N-ジメチルアンモニウムベタイン、N-(3-カルボキシメチル)-N-メタクリロイルアミドプロピル-N,N-ジメチルアンモニウムベタイン、N-(3-スルホプロピル)-N-メタクリロイルオキシエチル-N,N-ジメチルアンモニウムベタイン、N-カルボキシメチル-N-メタクリロイルオキシエチル-N,N-ジメチルアンモニウムベタイン等のベタイン類が挙げられる。 Examples of other vinyl monomers include methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, isopropyl (meth) acrylate, n-butyl (meth) acrylate, isobutyl (meth) acrylate, t-butyl (meth) acrylate, n-pentyl (meth) acrylate, neopentyl (meth) acrylate, cyclopentyl (meth) acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, n-octyl (meth) acrylate, Isooctyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, n-decyl (meth) acrylate, isodecyl (meth) acrylate, lauryl (meth) acrylate, tridecyl (meth) acrylate, stearyl (meth) acrylate , Isostearyl (meth) acrylate, behenyl (meth) acrylate, phenyl (meth) acrylate, toluyl (meth) acrylate, xylyl (meth) acrylate, benzyl (meth) acrylate, 2-ethoxyethyl (meth) acrylate, 2 -Butoxyethyl (meth) acrylate, 2-phenoxy (meth) acrylate, 2-methoxypropyl (meth) acrylate, 3-methoxypropyl (meth) acrylate, 2-ethoxypropyl (meth) acrylate, 3-ethoxypropyl (meth) (Meth) acrylic acid derivatives such as acrylate; anionic group-containing monomers such as 2-acrylamido-2-methylpropanesulfonic acid, sodium styrenesulfonate, acrylic acid, methacrylic acid, 2-sulfoethyl methacrylate; N- (3-sulfopropyl) -N- Cryroyloxyethyl-N, N-dimethylammonium betaine, N- (3-sulfopropyl) -N-methacryloylamidopropyl-N, N-dimethylammonium betaine, N- (3-carboxymethyl) -N-methacryloylamidopropyl -N, N-dimethylammonium betaine, N- (3-sulfopropyl) -N-methacryloyloxyethyl-N, N-dimethylammonium betaine, N-carboxymethyl-N-methacryloyloxyethyl-N, N-dimethylammonium betaine And the like betaines.
・重合方法
成分(C)のカチオン性基含有共重合体を製造する方法については必ずしも制限はないが、通常は水溶液重合法、逆相懸濁重合法、沈澱重合法などの方法によることが好ましい。
-Polymerization method The method for producing the cationic group-containing copolymer of component (C) is not necessarily limited, but it is usually preferable to use an aqueous solution polymerization method, reverse phase suspension polymerization method, precipitation polymerization method or the like. .
成分(C)のカチオン性基含有共重合体は、単独で又は２種以上を組み合わせて用いることができ、その含有量は、塗布しやすさの点から、全組成中の0.01〜２質量％、更には0.05〜1.5質量％、特に0.1〜１質量％が好ましい。 The cationic group-containing copolymer of component (C) can be used alone or in combination of two or more, and its content is 0.01 to 2% by mass in the total composition from the viewpoint of ease of application. Further, 0.05 to 1.5% by mass, particularly 0.1 to 1% by mass is preferable.
〔(D)：フェニル変性シリコーンオイル又はジメチルシリコーンオイル〕
本発明の一時染毛剤組成物には、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させるため、更に成分(D)として、25℃における動粘度が200mm2/s以下のフェニル変性シリコーンオイル又はジメチルシリコーンオイルを含有させることができる。
[(D): Phenyl-modified silicone oil or dimethyl silicone oil]
The temporary hair dye composition of the present invention has a kinematic viscosity at 25 ° C. of 200 mm 2 as a component (D) in order to further improve the feel after use while ensuring the effect obtained by the component (A). Phenyl-modified silicone oil or dimethylsilicone oil of not more than / s can be contained.
フェニル変性シリコーンオイルとしては、ジフェニルジメチコン、フェニルメチコン、フェニルトリメチコン等が挙げられる。具体的には、KF-50-100CS（25℃の動粘度100mm2/s）、KF-53（同175mm2/s）、KF-56（同14mm2/s）（以上、信越化学工業株式会社）、SH556（同14mm2/s）（東レ・ダウコーニング株式会社）等が挙げられる。 Examples of the phenyl-modified silicone oil include diphenyl dimethicone, phenyl methicone, and phenyl trimethicone. Specifically, KF-50-100CS (kinematic viscosity at 25 ° C 100 mm 2 / s), KF-53 (175 mm 2 / s), KF-56 (14 mm 2 / s) (Shin-Etsu Chemical Co., Ltd.) Company), SH556 (14mm 2 / s) (Toray Dow Corning Co., Ltd.).
ジメチルシリコーンオイルとしては、ジメチコン等が挙げられる。具体的には、KF-96A-200CS（25℃の動粘度200mm2/s）、KF-96A-100CS（同100mm2/s）、KF-96A-50CS（同50mm2/s）、KF-96A-30CS（同30mm2/s）、KF-96A-20CS（同20mm2/s）、KF-96A-10CS（同10mm2/s）、KF-96A-6CS（同６mm2/s）、KF -96A-5CS（同５mm2/s）、KF-96L-2CS（同２mm2/s）、KF-96L-1.5CS（同1.5mm2/s）、KF-96L-1CS（同１mm2/s）（以上、信越化学工業株式会社）、SH200 C Fluid 200CS（同200mm2/s）、SH200 C Fluid 100CS（同100mm2/s）、SH200 C Fluid 50CS（同50mm2/s）、SH200 C Fluid 30CS（同30mm2/s）、SH200 C Fluid 20CS（同20mm2/s）、SH200 C Fluid 10CS（同10mm2/s）、SH200 C Fluid 6CS（同６mm2/s）、SH200 C Fluid 5CS（同５mm2/s）、SH200 C Fluid 2CS（同２mm2/s）、SH200 Fluid 1.5CS（同1.5mm2/s）、SH200 C Fluid 1CS（同１mm2/s）（以上、東レ・ダウコーニング株式会社）等が挙げられる。 Examples of dimethyl silicone oil include dimethicone. Specifically, KF-96A-200CS (kinematic viscosity at 25 ° C 200 mm 2 / s), KF-96A-100CS (100 mm 2 / s), KF-96A-50CS (50 mm 2 / s), KF- 96A-30CS (30mm 2 / s), KF-96A-20CS (20mm 2 / s), KF-96A-10CS (10mm 2 / s), KF-96A-6CS (6mm 2 / s), KF -96A-5CS (5mm 2 / s), KF-96L-2CS (2mm 2 / s), KF-96L-1.5CS (1.5mm 2 / s), KF-96L-1CS (1mm 2) / s) (Shin-Etsu Chemical Co., Ltd.), SH200 C Fluid 200CS (200 mm 2 / s), SH200 C Fluid 100CS (100 mm 2 / s), SH200 C Fluid 50CS (50 mm 2 / s), SH200 C Fluid 30CS (30mm 2 / s), SH200 C Fluid 20CS (20mm 2 / s), SH200 C Fluid 10CS (10mm 2 / s), SH200 C Fluid 6CS (6mm 2 / s), SH200 C Fluid 5CS (5mm 2 / s), SH200 C Fluid 2CS (2mm 2 / s), SH200 Fluid 1.5CS (1.5mm 2 / s), SH200 C Fluid 1CS (1mm 2 / s) (Toray, Dow Corning Co., Ltd.).
成分(D)のフェニル変性シリコーンオイル、ジメチルシリコーンオイルは、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させる観点から、25℃における動粘度が200mm2/s以下のものが好ましく、更には150mm2/s以下、特に100mm2/s以下のものが好ましい。 Component (D) phenyl-modified silicone oil and dimethyl silicone oil have a kinematic viscosity at 25 ° C of 200 mm 2 / s or less from the viewpoint of further improving the feel after use while ensuring the effect obtained by component (A). Are preferably 150 mm 2 / s or less, more preferably 100 mm 2 / s or less.
成分(D)のフェニル変性シリコーンオイル、ジメチルシリコーンオイルは、単独で又は２種以上を組み合わせて用いることができ、その含有量は、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させる観点から、全組成中の0.1〜20質量％、更には0.5〜15質量％、特に１〜10質量％が好ましい。 The component (D) phenyl-modified silicone oil and dimethyl silicone oil can be used alone or in combination of two or more thereof, and the content thereof can be obtained after use while ensuring the effect obtained by the component (A). From the viewpoint of further improving the touch, 0.1 to 20% by mass, more preferably 0.5 to 15% by mass, and particularly preferably 1 to 10% by mass in the total composition.
〔(E)：ポリエーテル変性シリコーンオイル〕
本発明の一時染毛剤組成物には、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させるため、更に成分(E)として、HLBが２〜７のポリエーテル変性シリコーンオイルを含有させることができる。
[(E): Polyether-modified silicone oil]
In the temporary hair dye composition of the present invention, in order to further improve the feel after use while ensuring the effect obtained by the component (A), a polyether having 2 to 7 HLB as the component (E) is further provided. Modified silicone oil can be included.
成分(E)のポリエーテル変性シリコーンオイルは、ジメチルポリシロキサンの主鎖にポリオキシアルキレン基、好ましくはポリオキシエチレン基が結合したものであり、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させる観点から、HLBが２〜７のものが好ましく、更にはHLBが３〜６、特に４〜５のものが好ましい。なお、本明細書におけるHLBは、以下のように定義される。
HLB＝Ｅ／５（Ｅは分子中に含まれるポリオキシエチレン部分の質量％）
The polyether-modified silicone oil of component (E) is a dimethylpolysiloxane main chain bonded with a polyoxyalkylene group, preferably a polyoxyethylene group, while ensuring the effect obtained by component (A), From the viewpoint of further improving the feel after use, those having an HLB of 2 to 7 are preferred, and those having an HLB of 3 to 6, particularly 4 to 5 are preferred. In addition, HLB in this specification is defined as follows.
HLB = E / 5 (E is the mass% of the polyoxyethylene part contained in the molecule)
成分(E)のポリエーテル変性シリコーンオイルは、単独で又は２種以上を組み合わせて用いることができ、その含有量は、成分(A)によって得られる効果を確保しつつ、使用後の感触を更に向上させる観点から、全組成中の0.1〜10質量％、更には0.5〜８質量％、特に１〜５質量％が好ましい。 The polyether-modified silicone oil of component (E) can be used singly or in combination of two or more, and the content further enhances the feel after use while ensuring the effect obtained by component (A). From the viewpoint of improving, 0.1 to 10% by mass, more preferably 0.5 to 8% by mass, and particularly preferably 1 to 5% by mass in the total composition.
〔多価アルコール〕
本発明の一時染毛剤組成物は、多価アルコール類の含有量が、５質量％以下、更には２質量％以下であることが望ましく、実質的に含有しないことが最も望ましい。従来の一時染毛剤組成物には、被膜形成樹脂に可塑性を付与して着色皮膜を柔らかくし、感触を向上させるために、グリコール類（例えば、エチレングリコール、ジエチレングリコール、トリエチレングリコール、プロピレングリコール、ジプロピレングリコール、イソプレングリコール、1,3-ブチレングリコール等）、グリセリン類（例えば、グリセリン、ジグリセリン、ポリグリセリン等）等の多価アルコールが配合されている。しかし、本発明の場合、特にマスカラタイプ、フォームタイプ、スプレータイプ等の剤型の場合には、逆に多価アルコール類が少ない方が着色性、感触、耐水性に優れ、また速乾性も得られるため好ましい。
[Polyhydric alcohol]
In the temporary hair dye composition of the present invention, the content of polyhydric alcohols is desirably 5% by mass or less, more desirably 2% by mass or less, and most desirably not containing substantially. In conventional temporary hair dye compositions, glycols (for example, ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, Polyhydric alcohols such as dipropylene glycol, isoprene glycol, 1,3-butylene glycol, etc.) and glycerins (for example, glycerin, diglycerin, polyglycerin etc.) are blended. However, in the case of the present invention, especially in the case of dosage forms such as mascara type, foam type, spray type, etc., the smaller the number of polyhydric alcohols, the better the coloring, feel and water resistance, and quick drying. Therefore, it is preferable.
〔溶媒〕
本発明の一時染毛剤組成物は、水、低級アルコール又は水と低級アルコールの混合物を溶媒とすることが好ましい。低級アルコールとしては、エタノール、1-プロパノール、2-プロパノール等が挙げられ、中でもエタノール、2-プロパノール、特にエタノールが好ましい。溶媒の含有量は、調製時の溶解性促進、顔料分散性、塗布後の速乾性等の点から、全組成中の30〜98質量％が好ましく、更には40〜97質量％、特に50〜96質量％が好ましい。
〔solvent〕
The temporary hair dye composition of the present invention preferably uses water, a lower alcohol or a mixture of water and a lower alcohol as a solvent. Examples of the lower alcohol include ethanol, 1-propanol, 2-propanol and the like, and ethanol, 2-propanol, and particularly ethanol is preferable. The content of the solvent is preferably from 30 to 98% by mass, more preferably from 40 to 97% by mass, particularly from 50 to 97% by mass, from the viewpoints of solubility promotion during preparation, pigment dispersibility, quick drying after application, and the like. 96 mass% is preferred.
〔他の任意成分〕
本発明の一時染毛剤組成物には、これらのほかに、通常染毛剤組成物に用いられる成分を添加することができ、例えば、界面活性剤；油脂、難揮発性炭化水素類、シリコーン油等の油性成分；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、カルボキシビニルポリマー等の増粘剤；LPG（液化石油ガス）、ペンタン、ジメチルエーテル、ジエチルエーテル等の噴射剤；その他、香料、防腐剤、紫外線吸収剤、キレート剤、酸化防止剤、植物抽出物等を例示することができる。
[Other optional ingredients]
In addition to these, components that are usually used in hair dye compositions can be added to the temporary hair dye composition of the present invention. For example, surfactants; oils and fats, hardly volatile hydrocarbons, silicones Oily components such as oil; thickeners such as hydroxyethyl cellulose, hydroxypropyl cellulose, carboxyvinyl polymer; propellants such as LPG (liquefied petroleum gas), pentane, dimethyl ether, diethyl ether; other fragrances, preservatives, UV absorbers And chelating agents, antioxidants, plant extracts and the like.
〔剤型〕
本発明の一時染毛剤組成物の剤型は特に制限されず、例えばフォーム、ヘアマスカラ、ジェル、スプレー、クリーム、ワックス等の形態とすることができる。本発明の一時染毛剤組成物は、毛髪に適用した後、洗い流さずに放置して使用される。
[Drug type]
The dosage form of the temporary hair dye composition of the present invention is not particularly limited, and may be in the form of foam, hair mascara, gel, spray, cream, wax or the like. The temporary hair dye composition of the present invention is used after being applied to hair, without being washed away.
以下の実施例において、オルガノポリシロキサンセグメントの含有率とは核磁気共鳴法（1H-NMR）から求めた値であり、また最終生成物の重量平均分子量は計算値である。ポリ（N-プロピオニルエチレンイミン）の分子量は、ゲルパーミエーションクロマトグラフィー(GPC)より求めた、数平均分子量である。 In the following examples, the content of the organopolysiloxane segment is a value determined by nuclear magnetic resonance (1H-NMR), and the weight average molecular weight of the final product is a calculated value. The molecular weight of poly (N-propionylethyleneimine) is a number average molecular weight determined by gel permeation chromatography (GPC).
Column ：K-804L＋K-804L 昭和電工（株）製
溶離液 ：１mmol/ＬファーミンDM20（花王（株）製）／クロロホルム
流量 ：1.0mL／min
カラム温度：40℃
検出器 ：RI
サンプル量：５mg/mL，100μL
ポリスチレン換算
Column: K-804L + K-804L manufactured by Showa Denko KK Eluent: 1 mmol / L Pharmin DM20 (manufactured by Kao Corporation) / chloroform Flow rate: 1.0 mL / min
Column temperature: 40 ° C
Detector: RI
Sample amount: 5mg / mL, 100μL
Polystyrene conversion
合成例１ オルガノポリシロキサンＡ
硫酸ジエチル0.8ｇ（0.005モル）と2-エチル−２−オキサゾリン12.8ｇ（0.14モル）を脱水した酢酸エチル29ｇに溶解し、窒素雰囲気下８時間加熱還流し、末端反応性ポリ（N-プロピオニルエチレンイミン）を合成した。数平均分子量をGPCにより測定したところ、2700であった。ここに、側鎖一級アミノプロピル変性ポリジメチルシロキサン（重量平均分子量100000、アミン当量20000）100ｇを酢酸エチルの33％溶液とした上で一括して加え、10時間加熱還流した。反応混合物を減圧濃縮し、N-プロピオニルエチレンイミン−ジメチルシロキサン共重合体を、淡黄色ゴム状固体（111ｇ、収率98％）として得た。最終生成物のオルガノポリシロキサンセグメントの含有率は88質量％であり、重量平均分子量は114000であった。溶媒としてメタノールを使用した塩酸による中和滴定の結果、アミノ基は残存していないことがわかった。
Synthesis Example 1 Organopolysiloxane A
Dissolve 0.8 g (0.005 mol) of diethyl sulfate and 12.8 g (0.14 mol) of 2-ethyl-2-oxazoline in 29 g of dehydrated ethyl acetate, and heat and reflux for 8 hours under a nitrogen atmosphere. End-reactive poly (N-propionylethylene) Imine) was synthesized. The number average molecular weight measured by GPC was 2700. To this was added 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 100000, amine equivalent 20000) in a 33% solution of ethyl acetate, and the mixture was heated to reflux for 10 hours. The reaction mixture was concentrated under reduced pressure to obtain an N-propionylethyleneimine-dimethylsiloxane copolymer as a pale yellow rubber-like solid (111 g, yield 98%). The content of the organopolysiloxane segment in the final product was 88% by mass, and the weight average molecular weight was 114,000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that no amino group remained.
合成例２ オルガノポリシロキサンＢ
合成例１と同様の方法により、硫酸ジエチル0.6ｇ（0.004モル）と２−エチル−２−オキサゾリン3.6ｇ（0.04モル）、脱水した酢酸エチル9ｇから、数平均分子量1200のポリ（Ｎ−プロピオニルエチレンイミン）を得た。更に、側鎖一級アミノプロピル変性ポリジメチルシロキサン（重量平均分子量100000、アミン当量20000）100ｇを用いて、Ｎ−プロピオニルエチレンイミン−ジメチルシロキサン共重合体を淡黄色ゴム状固体（95ｇ、収率95％）として得た。最終生成物のオルガノポリシロキサンセグメントの含有率は96質量％であり、重量平均分子量は104000であった。溶媒としてメタノールを使用した塩酸による中和滴定の結果、約30質量％のアミノ基が残存していることがわかった。
Synthesis Example 2 Organopolysiloxane B
In the same manner as in Synthesis Example 1, 0.6 g (0.004 mol) of diethyl sulfate, 3.6 g (0.04 mol) of 2-ethyl-2-oxazoline, and 9 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 1200. Imin). Further, 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 100000, amine equivalent 20000) was used to convert N-propionylethyleneimine-dimethylsiloxane copolymer to a pale yellow rubbery solid (95 g, yield 95%). ). The content of the organopolysiloxane segment in the final product was 96% by mass, and the weight average molecular weight was 104000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 30% by mass of amino groups remained.
合成例３ オルガノポリシロキサンＣ
合成例１と同様の方法により、硫酸ジエチル6.5ｇ（0.042モル）と2-エチル-2-オキサゾリン20.1ｇ（0.21モル）、脱水した酢酸エチル57ｇから、数平均分子量900のポリ（N-プロピオニルエチレンイミン）を得た。更に、側鎖一級アミノプロピル変性ポリジメチルシロキサン（重量平均分子量36000、アミン当量2000）100ｇを用いて、N-プロピオニルエチレンイミン−ジメチルシロキサン共重合体を淡黄色水飴状半固体（124ｇ、収率98％）として得た。最終生成物のオルガノポリシロキサンセグメントの含有率は79質量％、重量平均分子量は46000であった。溶媒としてメタノールを使用した塩酸による中和滴定の結果、約21モル％のアミノ基が残存していることがわかった。
Synthesis Example 3 Organopolysiloxane C
In the same manner as in Synthesis Example 1, 6.5 g (0.042 mol) of diethyl sulfate, 20.1 g (0.21 mol) of 2-ethyl-2-oxazoline and 57 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 900. Imin). Further, 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 36000, amine equivalent 2000) was used to convert the N-propionylethyleneimine-dimethylsiloxane copolymer into a pale yellow syrupy semisolid (124 g, yield 98). %). The final product had an organopolysiloxane segment content of 79% by mass and a weight average molecular weight of 46000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 21 mol% of amino groups remained.
合成例４ オルガノポリシロキサンＤ
合成例１と同様の方法により、硫酸ジエチル3.2ｇ（0.021モル）と2-エチル-2-オキサゾリン92.8ｇ（0.98モル）、脱水した酢酸エチル205ｇから、数平均分子量5200のポリ（N-プロピオニルエチレンイミン）を得た。更に、側鎖一級アミノプロピル変性ポリジメチルシロキサン（重量平均分子量50000、アミン当量3800）100ｇを用いて、N-プロピオニルエチレンイミン−ジメチルシロキサン共重合体を淡黄色ゴム状固体（188ｇ、収率96％）として得た。最終生成物のオルガノポリシロキサンセグメントの含有率は51質量％であり、重量平均分子量は98000であった。溶媒としてメタノールを使用した塩酸による中和滴定の結果、約24モル％のアミノ基が残存していることがわかった。
Synthesis Example 4 Organopolysiloxane D
In the same manner as in Synthesis Example 1, 3.2 g (0.021 mol) of diethyl sulfate, 92.8 g (0.98 mol) of 2-ethyl-2-oxazoline and 205 g of dehydrated ethyl acetate were added to poly (N-propionylethylene having a number average molecular weight of 5200. Imin). Further, 100 g of side chain primary aminopropyl-modified polydimethylsiloxane (weight average molecular weight 50000, amine equivalent 3800) was used to convert N-propionylethyleneimine-dimethylsiloxane copolymer into a pale yellow rubber-like solid (188 g, yield 96%). ). The content of the organopolysiloxane segment in the final product was 51% by mass, and the weight average molecular weight was 98,000. As a result of neutralization titration with hydrochloric acid using methanol as a solvent, it was found that about 24 mol% of amino groups remained.
実施例１〜27及び比較例１〜９
表１に示す処方の一時染毛剤組成物（フォーム剤）及び表２に示す処方の一時染毛剤組成物（ヘアマスカラ剤）を調製し、以下の方法及び基準に従って、「着色性」、「色移りのし難さ」、「耐水性」、「着色毛束の感触（柔かさ）」、「着色毛束の感触（ベタツキのなさ）」について評価した。
Examples 1-27 and Comparative Examples 1-9
A temporary hair dye composition (foam) having the formulation shown in Table 1 and a temporary hair dye composition (hair mascara) having the formulation shown in Table 2 were prepared, and according to the following method and criteria, “colorability”, Evaluation was made on “difficulty of color transfer”, “water resistance”, “feel of colored hair bundle (softness)”, and “feel of colored hair bundle (no stickiness)”.
◆一時染毛剤の調製
表１に示す処方をディスパー（特殊機化工業社製，ホモディスパー）により撹拌混合（1000rpm，５分間）して原液を調製し、エアゾール試験瓶（東京高分子社製）に入れ、撹拌球（ステンレス製，直径６mm）を入れた後に試験瓶専用バルブで密栓し、原液：噴射剤＝90：10の質量比で噴射剤（LPG，0.44MPa）を充填して、一時染毛剤（フォーム剤）を調製した。
また、表２に示す処方をディスパー（特殊機化工業社製，ホモディスパー）により撹拌混合（1000rpm，５分間）して液を調製し、マスカラ用容器（花王社製「ブローネポイントカバー」の容器）に入れ、撹拌球（ステンレス製，直径３mm）を入れた後に液を充填して、一時染毛剤（ヘアマスカラ剤）を調製した。
なお、花王社製「ブローネポイントカバー」の容器は、ボトル、ブラシ付のキャップ、ブラシに含浸した過剰のヘアマスカラ液を絞り落とすためのシゴキゴムの３点から構成される。ボトルはプロピレン製の円筒形で、その径は16.2mm、高さは91.5mmである。シゴキゴムはニトリルブタジエンラバー製で、ボトルの口に嵌め込まれ、その穴径は3.4mmである。ブラシは線径が0.7mmのナイロン糸がステンレス（SUS304）のワイヤーに編みこまれており、ブラシ長さは21.5mm、ブラシ径は6.2mm、ブラシの山数は12であり、プロピレンの軸を介してキャップと連結している。キャップの高さは40mm、キャップとブラシとを組立てた時の高さが118mmである。
◆ Preparation of temporary hair dye The formulation shown in Table 1 was stirred and mixed (1000 rpm, 5 minutes) with a disper (made by Tokushu Kika Kogyo Co., Ltd.) to prepare a stock solution. ), Put a stirring ball (stainless steel, 6 mm in diameter) and seal it with a valve dedicated to a test bottle, and fill with propellant (LPG, 0.44 MPa) at a mass ratio of stock solution: propellant = 90:10, A temporary hair dye (foaming agent) was prepared.
In addition, the formulation shown in Table 2 was stirred and mixed (1000 rpm, 5 minutes) with a disper (made by Tokushu Kika Kogyo Co., Ltd., homodisper) to prepare a liquid, and a container for mascara (a container for “Brone Point Cover” made by Kao) ), A stirring ball (made of stainless steel, 3 mm in diameter) was added, and the solution was filled to prepare a temporary hair dye (hair mascara).
In addition, the container of “Brone point cover” manufactured by Kao Corporation is composed of three points: bottle, cap with brush, and shigoki rubber for squeezing out excess hair mascara liquid impregnated in the brush. The bottle is a propylene cylinder with a diameter of 16.2mm and a height of 91.5mm. Shigoki rubber is made of nitrile butadiene rubber and is fitted into the mouth of the bottle. Its hole diameter is 3.4mm. The brush has a 0.7mm diameter nylon thread woven into stainless steel (SUS304) wire, the brush length is 21.5mm, the brush diameter is 6.2mm, the number of brush crests is 12, and the propylene shaft is Via the cap. The height of the cap is 40 mm, and the height when the cap and brush are assembled is 118 mm.
◆評価用毛束
ヤギ毛束（ビューラックス社製，10cm，１ｇ）を下記組成のモデルシャンプーで洗浄後、十分に乾燥したものを用意した。
この毛束に各フォーム剤0.4ｇを塗布し、指でよく馴染ませ、20℃、相対湿度60％の条件下で２時間自然乾燥して、着色毛束を得た。
また、この毛束に各ヘアマスカラ剤を、前述のマスカラ用容器のブラシを用いて毛束全体に均等になるように塗布した。マスカラ用容器のボトル内にブラシを差込み、ヘアマスカラ剤を十分に含浸させた後、ブラシをシゴキゴムを通して過剰の液を絞り落としながら 引き抜き、毛束に塗布した。この操作を連続８回繰り返し、毛束全体にヘアマスカラ剤0.4gを均等に塗布し、20℃、相対湿度60％の条件下で２時間自然乾燥して、着色毛束を得た。
◆ Evaluation hair bundle A goat hair bundle (manufactured by Beaulux, 10 cm, 1 g) was washed with a model shampoo having the following composition, and then sufficiently dried.
Each foam agent 0.4g was apply | coated to this hair | bristle bundle, it was made to adapt well with a finger | toe, and naturally dried for 2 hours on the conditions of 20 degreeC and relative humidity 60%, and the colored hair | bristle bundle was obtained.
Moreover, each hair mascara agent was apply | coated to this hair bundle so that it might become equal to the whole hair bundle using the brush of the container for mascara mentioned above. The brush was inserted into the bottle of the mascara container and sufficiently impregnated with the hair mascara agent, and then the brush was pulled out while squeezing out excess liquid through squeegee rubber and applied to the hair bundle. This operation was repeated 8 times in succession, 0.4 g of a hair mascara agent was evenly applied to the entire hair bundle, and naturally dried for 2 hours at 20 ° C. and a relative humidity of 60% to obtain a colored hair bundle.
（モデルシャンプー組成） （質量％）
ポリオキシエチレン(2.5)ラウリルエーテル硫酸ナトリウム（25質量％） 62.00
ラウリン酸ジエタノールアミド 2.28
エデト酸二ナトリウム 0.10
安息香酸ナトリウム 0.50
オキシベンゾン 0.03
リン酸（75質量％） 0.10
ジブチルヒドロキシトルエン 0.01
塩化ナトリウム 0.80
精製水 残量
合計 100
(Model shampoo composition) (mass%)
Polyoxyethylene (2.5) sodium lauryl ether sulfate (25% by mass) 62.00
Lauric acid diethanolamide 2.28
Edetate disodium 0.10
Sodium benzoate 0.50
Oxybenzone 0.03
Phosphoric acid (75% by mass) 0.10
Dibutylhydroxytoluene 0.01
Sodium chloride 0.80
Purified water remaining total 100
◆一時染毛剤の性能評価
１）着色性
各着色毛束について、色彩色差計（コニカミノルタ社製，CR-400）により、ヤギ毛束の着色前後における色差（ΔＥ）を測定し、Ｎ＝３の平均値をもって下記基準に従い評価を行った。
◆ Performance Evaluation of Temporary Hair Dye 1) Colorability For each colored hair bundle, the color difference (ΔE) before and after coloring of the goat hair bundle was measured with a color difference meter (Konica Minolta, CR-400), N = Evaluation was performed according to the following criteria with an average value of 3.
（評価基準）
◎：Ｘ≧Ｙ＋３
○：Ｙ＋３＞Ｘ≧Ｙ
△：Ｙ＞Ｘ≧Ｙ−３
×：Ｙ−３＞Ｘ
※Ｘは評価対象のΔＥ値
Ｙは比較例１のΔＥ値
(Evaluation criteria)
A: X ≧ Y + 3
○: Y + 3> X ≧ Y
Δ: Y> X ≧ Y-3
X: Y-3> X
* X is the ΔE value to be evaluated
Y is the ΔE value of Comparative Example 1
２）色移り（二次付着）のし難さ
各着色毛束を濾紙（東洋濾紙社製，定性濾紙，No.2，直径150mm）を半分に折り畳んだ間に挟み、重り（水を入れて全量を1200ｇに調整した1000mLガラスビーカー（外径110mm，全高150mm））を、ヤギ毛束全体を押さえるように載置した。
このまま１分間放置した後、試験後の各濾紙と、試験前の濾紙との色差（ΔＥ）を、色彩色差計（コニカミノルタ社製，CR-400）により測定し、Ｎ＝３の平均値をもって下記基準に従い評価を行った。
2) Difficulty of color transfer (secondary adhesion) Each colored hair bundle is sandwiched between filter paper (Toyo Roshi Kaisha, qualitative filter paper, No.2, diameter 150mm) folded in half, and weight (with water added) A 1000 mL glass beaker (outer diameter 110 mm, total height 150 mm) adjusted to 1200 g in total was placed so as to hold the entire goat hair bundle.
After leaving for 1 minute, the color difference (ΔE) between each filter paper after the test and the filter paper before the test was measured with a color difference meter (CR-400, manufactured by Konica Minolta Co., Ltd.), and an average value of N = 3 Evaluation was performed according to the following criteria.
（評価基準）
◎：ΔＥが0.5未満
○：ΔＥが0.5以上、１未満
△：ΔＥが１以上、３未満
×：ΔＥが３以上
(Evaluation criteria)
◎: ΔE is less than 0.5 ○: ΔE is 0.5 or more and less than 1 △: ΔE is 1 or more and less than 3 ×: ΔE is 3 or more
３）耐水性
各着色毛束を500mLガラスビーカー（外径90mm、全高120mm）に入れた500mLの水の中に浸漬し、３分間静置した。その後、毛束を水中から引き上げ、十分に濡れたままの毛束を濾紙（東洋濾紙社製、定性濾紙、No.2、直径150mm）を半分に折り畳んだ間に挟み、重り（水を入れて全量を1200ｇに調整した1000mLガラスビーカー（外径110mm、全高150mm））を、ヤギ毛束全体を押さえるように載置した。
このまま１分間放置した後、毛束を取り除き、20℃、相対湿度60％の条件下で24時間乾燥させた各濾紙と、試験前の濾紙との色差（ΔＥ）を、色彩色差計（コニカミノルタ社製，CR-400）により測定し、Ｎ＝３の平均値をもって下記基準に従い評価を行った。
3) Water resistance Each colored hair bundle was immersed in 500 mL of water placed in a 500 mL glass beaker (outer diameter 90 mm, total height 120 mm) and allowed to stand for 3 minutes. After that, pull up the hair bundle from the water, put the hair bundle while it is sufficiently wet between filter paper (Toyo Roshi Kaisha, qualitative filter paper, No.2, diameter 150mm) folded in half, and add weight (with water) A 1000 mL glass beaker (outer diameter 110 mm, total height 150 mm) adjusted to a total amount of 1200 g was placed so as to hold the entire goat hair bundle.
After leaving for 1 minute, the hair bundle was removed, and the color difference (ΔE) between each filter paper dried at 20 ° C. and 60% relative humidity for 24 hours and the filter paper before the test was measured with a color difference meter (Konica Minolta). CR-400), and an average value of N = 3 was evaluated according to the following criteria.
（評価基準）
◎：ΔＥが0.5未満
○：ΔＥが0.5以上、１未満
△：ΔＥが１以上、３未満
×：ΔＥが３以上
(Evaluation criteria)
◎: ΔE is less than 0.5 ○: ΔE is 0.5 or more and less than 1 △: ΔE is 1 or more and less than 3 ×: ΔE is 3 or more
４）着色毛束の感触（柔らかさ）
各着色毛束について、パネラー５名による５段階官能評価（着色毛束を指で触った時の柔らかさの評価）を行った。５名の評価の合計点をもって下記基準に従い評価を行った。
4) Colored hair bundle feel (softness)
Each colored hair bundle was subjected to a five-step sensory evaluation (evaluation of softness when the colored hair bundle was touched with a finger) by five panelists. Evaluation was made according to the following criteria with a total score of five people.
（評価点）
５点：比較例１よりも柔らかいと感じる
４点：比較例１よりもやや柔らかいと感じる
３点：どちらともいえない
２点：比較例１の方がやや柔らかいと感じる
１点：比較例１の方が柔らかいと感じる
(Evaluation points)
5 points: feels softer than Comparative Example 1 4 points: feels slightly softer than Comparative Example 1 3 points: cannot be said 2 points: Comparative Example 1 feels slightly softer 1 point: Comparative Example 1 Feels softer
（評価基準）
◎：23点以上
○：23点未満、20点以上
△：20点未満、16点以上
×：16点未満
(Evaluation criteria)
◎: 23 points or more ○: Less than 23 points, 20 points or more △: Less than 20 points, 16 points or more ×: Less than 16 points
５）着色毛束の感触（ベタツキの無さ）
各着色毛束について、パネラー５名による５段階官能評価（着色毛束を指で触った時のベタツキの無さの評価）を行った。５名の評価の合計点をもって下記基準に従い評価を行った。
5) Colored hair bundle feel (no stickiness)
Each colored hair bundle was subjected to a five-step sensory evaluation (an evaluation of the absence of stickiness when the colored hair bundle was touched with a finger) by five panelists. Evaluation was made according to the following criteria with a total score of five people.
（評価点）
５点：比較例１よりもベタツキがないと感じる
４点：比較例１よりもややベタツキがないと感じる
３点：どちらともいえない
２点：比較例１の方がややベタツキがないと感じる
１点：比較例１の方がベタツキがないと感じる
(Evaluation points)
5 points: feels less sticky than Comparative Example 1 4 points: feels less sticky than Comparative Example 1 3 points: cannot say 2 points: feels Comparative Example 1 is somewhat less sticky 1 Point: Comparative Example 1 feels less sticky
（評価基準）
◎：20点以上
○：20点未満、15点以上
△：15点未満、10点以上
×：10点未満
(Evaluation criteria)
◎: 20 points or more ○: Less than 20 points, 15 points or more △: Less than 15 points, 10 points or more ×: Less than 10 points
６）洗浄性
各着色毛束をモデルシャンプーで２回洗浄後、ドライヤーの冷風を30分間あてて、十分に乾燥して、洗浄済毛束を得た。着色後、洗浄して乾燥させた毛束と、着色試験前の毛束との色差（ΔＥ）を、色彩色差計（コニカミノルタ社製，CR-400）により測定し、Ｎ＝３の平均値をもって下記基準に従い評価を行った。
6) Detergency Each colored hair bundle was washed twice with a model shampoo, and then dried with cold air from a dryer for 30 minutes to obtain a washed hair bundle. After coloring, the color difference (ΔE) between the hair bundle washed and dried and the hair bundle before the coloring test was measured with a color difference meter (manufactured by Konica Minolta, CR-400), and the average value of N = 3 Was evaluated according to the following criteria.
（評価基準）
◎：ΔＥが10未満
○：ΔＥが10以上、15未満
△：ΔＥが15以上、20未満
×：ΔＥが20以上
(Evaluation criteria)
◎: ΔE is less than 10 ○: ΔE is 10 or more and less than 15 △: ΔE is 15 or more and less than 20 ×: ΔE is 20 or more
*１：ユカフォーマーSM（三菱化学社製）
*２：ソフタノール90（日本触媒社製）
*３：ソフケアKG-301W（花王社製）
*４：HPC-M（日本曹達社製）
*５：Carbopol ETD2020（ルブリゾール社製）
*６：SH556（東レ・ダウコーニング社製）
*７：KF50-100CS（信越シリコーン社製）
*８：KF50-1000CS（信越シリコーン社製）
*９：SH200 C Fluid 200cs（東レ・ダウコーニング社製）
*10：SH200 C Fluid 1000cs（東レ・ダウコーニング社製）
*11：SH3775M（東レ・ダウコーニング社製）
*12：SH3773M（東レ・ダウコーニング社製）
* 1: Yuka Former SM (Mitsubishi Chemical Corporation)
* 2: Softanol 90 (made by Nippon Shokubai Co., Ltd.)
* 3: Sofcare KG-301W (manufactured by Kao Corporation)
* 4: HPC-M (Nippon Soda Co., Ltd.)
* 5: Carbopol ETD2020 (manufactured by Lubrizol)
* 6: SH556 (Toray Dow Corning)
* 7: KF50-100CS (manufactured by Shin-Etsu Silicone)
* 8: KF50-1000CS (manufactured by Shin-Etsu Silicone)
* 9: SH200 C Fluid 200cs (Toray Dow Corning)
* 10: SH200 C Fluid 1000cs (Toray Dow Corning)
* 11: SH3775M (Toray Dow Corning)
* 12: SH3773M (Toray Dow Corning)
なお、実施例９〜12、15、19については、精製水をエタノールに置き換えた、実質的に非水系のヘアマスカラ剤についても調製した。これらのものについても同様にして評価を行い、同様な結果が得られた。
それ以外の実施例についても、実質的に非水系のヘアマスカラ剤として調製することができる。これらのものも同様にして評価を行えば、同様な結果が得られる。
In addition, about Examples 9-12, 15, and 19, it prepared also about the substantially non-aqueous hair mascara agent which replaced the purified water with ethanol. These were also evaluated in the same manner, and similar results were obtained.
Other examples can also be prepared as substantially non-aqueous hair mascara agents. If these are evaluated in the same manner, similar results can be obtained.
Claims (6)
(A) 主鎖を構成するオルガノポリシロキサンセグメントのケイ素原子の少なくとも２つに、ヘテロ原子を含むアルキレン基を介して、下記一般式(1)；
で表される繰り返し単位からなるポリ（N-アシルアルキレンイミン）セグメントが結合してなるオルガノポリシロキサンであって、
主鎖を構成するオルガノポリシロキサンセグメント（ａ）と、ポリ（N-アシルアルキレンイミン）セグメント（ｂ）との質量比（ａ／ｂ）が83／17〜98／2であり、
主鎖を構成するオルガノポリシロキサンの重量平均分子量が10,000〜200,000であり、
隣接するポリ（N-アシルアルキレンイミン）セグメント間におけるオルガノポリシロキサンセグメントの重量平均分子量（グラフト点間分子量）が12,000〜30,000である、
オルガノポリシロキサン
(B) 顔料及び／又は直接染料 A temporary hair dye composition containing the following components (A) and (B), wherein the content of the component (A) is 3 to 20% by mass.
(A) At least two silicon atoms of the organopolysiloxane segment constituting the main chain, via an alkylene group containing a hetero atom, the following general formula (1);
An organopolysiloxane formed by bonding poly (N-acylalkyleneimine) segments composed of repeating units represented by:
The mass ratio (a / b) between the organopolysiloxane segment (a) constituting the main chain and the poly (N-acylalkylenimine) segment (b) is 83/17 to 98/2,
The weight average molecular weight of the organopolysiloxane constituting the main chain is 10,000 to 200,000,
The weight average molecular weight (molecular weight between graft points) of the organopolysiloxane segment between adjacent poly (N-acylalkyleneimine) segments is 12,000 to 30,000,
Organopolysiloxane
(B) Pigments and / or direct dyes
(C) 一般式(I)又は(II)で表される親水性ノニオン性基含有ビニル単量体の少なくとも１種と、一般式(III)又は(IV)で表されるカチオン性基含有ビニル単量体の少なくとも１種と、ビニル基、アクリロイル基、メタクリロイル基及びアリル基から選ばれる少なくとも２個の基を分子中に有する架橋性ビニル単量体の少なくとも１種とを必須構成単量体とし、ラジカル重合することにより得られる、カチオン性基含有共重合体
(C) At least one hydrophilic nonionic group-containing vinyl monomer represented by general formula (I) or (II) and a cationic group-containing vinyl represented by general formula (III) or (IV) Essential constituent monomers comprising at least one monomer and at least one cross-linkable vinyl monomer having in the molecule at least two groups selected from vinyl, acryloyl, methacryloyl and allyl groups And a cationic group-containing copolymer obtained by radical polymerization
(D) 25℃における動粘度が200mm2/s以下のフェニル変性シリコーンオイル又はジメチルシリコーンオイル。 Furthermore, the temporary hair dye composition in any one of Claims 1-4 containing the following component (D).
(D) Phenyl-modified silicone oil or dimethyl silicone oil having a kinematic viscosity at 25 ° C. of 200 mm 2 / s or less.
(E) HLBが２〜７のポリエーテル変性シリコーンオイル。 Furthermore, the temporary hair-dyeing composition in any one of Claims 1-5 containing the following component (E).
(E) A polyether-modified silicone oil having an HLB of 2 to 7.
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Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2014080384A (en) * | 2012-10-16 | 2014-05-08 | Hoyu Co Ltd | Hair treatment agent composition |
| JP2017114815A (en) * | 2015-12-24 | 2017-06-29 | 花王株式会社 | Temporary hair dye composition |
| JP2018150280A (en) * | 2017-03-14 | 2018-09-27 | 花王株式会社 | Temporary hair dyeing composition |
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| JPH05112423A (en) * | 1991-10-18 | 1993-05-07 | Kao Corp | Cosmetic |
| JPH07133352A (en) * | 1993-08-10 | 1995-05-23 | Kao Corp | Organopolysiloxane, hair-setting composition containing same, and setting method for hair using the same |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| JP2014080384A (en) * | 2012-10-16 | 2014-05-08 | Hoyu Co Ltd | Hair treatment agent composition |
| JP2017114815A (en) * | 2015-12-24 | 2017-06-29 | 花王株式会社 | Temporary hair dye composition |
| JP2018150280A (en) * | 2017-03-14 | 2018-09-27 | 花王株式会社 | Temporary hair dyeing composition |
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