JP7481326B2 - カルボシロキサンデンドリマー構造を有する共重合体、並びにこれを含有する組成物、化粧料原料、皮膜形成剤及び化粧料 - Google Patents
カルボシロキサンデンドリマー構造を有する共重合体、並びにこれを含有する組成物、化粧料原料、皮膜形成剤及び化粧料 Download PDFInfo
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 1
- NNMHYFLPFNGQFZ-UHFFFAOYSA-M sodium polyacrylate Chemical compound [Na+].[O-]C(=O)C=C NNMHYFLPFNGQFZ-UHFFFAOYSA-M 0.000 description 1
- NTHWMYGWWRZVTN-UHFFFAOYSA-N sodium silicate Chemical compound [Na+].[Na+].[O-][Si]([O-])=O NTHWMYGWWRZVTN-UHFFFAOYSA-N 0.000 description 1
- 229910052911 sodium silicate Inorganic materials 0.000 description 1
- WYPBVHPKMJYUEO-NBTZWHCOSA-M sodium;(9z,12z)-octadeca-9,12-dienoate Chemical compound [Na+].CCCCC\C=C/C\C=C/CCCCCCCC([O-])=O WYPBVHPKMJYUEO-NBTZWHCOSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 229940031439 squalene Drugs 0.000 description 1
- TUHBEKDERLKLEC-UHFFFAOYSA-N squalene Natural products CC(=CCCC(=CCCC(=CCCC=C(/C)CCC=C(/C)CC=C(C)C)C)C)C TUHBEKDERLKLEC-UHFFFAOYSA-N 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 229920003179 starch-based polymer Polymers 0.000 description 1
- 239000004628 starch-based polymer Substances 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 229960004274 stearic acid Drugs 0.000 description 1
- 125000003696 stearoyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229940012831 stearyl alcohol Drugs 0.000 description 1
- 229910052917 strontium silicate Inorganic materials 0.000 description 1
- QSQXISIULMTHLV-UHFFFAOYSA-N strontium;dioxido(oxo)silane Chemical compound [Sr+2].[O-][Si]([O-])=O QSQXISIULMTHLV-UHFFFAOYSA-N 0.000 description 1
- 229940117986 sulfobetaine Drugs 0.000 description 1
- 150000003871 sulfonates Chemical class 0.000 description 1
- 125000000542 sulfonic acid group Chemical group 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000002730 suntanning agent Substances 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 239000003784 tall oil Substances 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- WYKYCHHWIJXDAO-UHFFFAOYSA-N tert-butyl 2-ethylhexaneperoxoate Chemical compound CCCCC(CC)C(=O)OOC(C)(C)C WYKYCHHWIJXDAO-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 150000003512 tertiary amines Chemical group 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- BORJONZPSTVSFP-UHFFFAOYSA-N tetradecyl 2-hydroxypropanoate Chemical compound CCCCCCCCCCCCCCOC(=O)C(C)O BORJONZPSTVSFP-UHFFFAOYSA-N 0.000 description 1
- DZKXJUASMGQEMA-UHFFFAOYSA-N tetradecyl tetradecanoate Chemical compound CCCCCCCCCCCCCCOC(=O)CCCCCCCCCCCCC DZKXJUASMGQEMA-UHFFFAOYSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- OULAJFUGPPVRBK-UHFFFAOYSA-N tetratriacontyl alcohol Natural products CCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCCO OULAJFUGPPVRBK-UHFFFAOYSA-N 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 125000003944 tolyl group Chemical group 0.000 description 1
- 235000015961 tonic Nutrition 0.000 description 1
- 230000001256 tonic effect Effects 0.000 description 1
- 229960000716 tonics Drugs 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- LOIYMIARKYCTBW-OWOJBTEDSA-N trans-urocanic acid Chemical compound OC(=O)\C=C\C1=CNC=N1 LOIYMIARKYCTBW-OWOJBTEDSA-N 0.000 description 1
- LADGBHLMCUINGV-UHFFFAOYSA-N tricaprin Chemical compound CCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCC)COC(=O)CCCCCCCCC LADGBHLMCUINGV-UHFFFAOYSA-N 0.000 description 1
- 239000001069 triethyl citrate Substances 0.000 description 1
- VMYFZRTXGLUXMZ-UHFFFAOYSA-N triethyl citrate Natural products CCOC(=O)C(O)(C(=O)OCC)C(=O)OCC VMYFZRTXGLUXMZ-UHFFFAOYSA-N 0.000 description 1
- 235000013769 triethyl citrate Nutrition 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 125000000725 trifluoropropyl group Chemical group [H]C([H])(*)C([H])([H])C(F)(F)F 0.000 description 1
- 229940117985 trimethyl pentaphenyl trisiloxane Drugs 0.000 description 1
- SZEMGTQCPRNXEG-UHFFFAOYSA-M trimethyl(octadecyl)azanium;bromide Chemical compound [Br-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C SZEMGTQCPRNXEG-UHFFFAOYSA-M 0.000 description 1
- STYCVOUVPXOARC-UHFFFAOYSA-M trimethyl(octyl)azanium;hydroxide Chemical compound [OH-].CCCCCCCC[N+](C)(C)C STYCVOUVPXOARC-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
- SVTUWEUXLNHYPF-UHFFFAOYSA-N trimethyl-[propyl-bis(trimethylsilyloxy)silyl]oxysilane Chemical compound CCC[Si](O[Si](C)(C)C)(O[Si](C)(C)C)O[Si](C)(C)C SVTUWEUXLNHYPF-UHFFFAOYSA-N 0.000 description 1
- 229940118594 trimethylolpropane triisostearate Drugs 0.000 description 1
- VLPFTAMPNXLGLX-UHFFFAOYSA-N trioctanoin Chemical compound CCCCCCCC(=O)OCC(OC(=O)CCCCCCC)COC(=O)CCCCCCC VLPFTAMPNXLGLX-UHFFFAOYSA-N 0.000 description 1
- UJMBCXLDXJUMFB-UHFFFAOYSA-K trisodium;5-oxo-1-(4-sulfonatophenyl)-4-[(4-sulfonatophenyl)diazenyl]-4h-pyrazole-3-carboxylate Chemical compound [Na+].[Na+].[Na+].[O-]C(=O)C1=NN(C=2C=CC(=CC=2)S([O-])(=O)=O)C(=O)C1N=NC1=CC=C(S([O-])(=O)=O)C=C1 UJMBCXLDXJUMFB-UHFFFAOYSA-K 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N tristearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 239000002383 tung oil Substances 0.000 description 1
- PBYZMCDFOULPGH-UHFFFAOYSA-N tungstate Chemical compound [O-][W]([O-])(=O)=O PBYZMCDFOULPGH-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229960002703 undecylenic acid Drugs 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 1
- 238000005292 vacuum distillation Methods 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 235000019871 vegetable fat Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 239000010455 vermiculite Substances 0.000 description 1
- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 229920001567 vinyl ester resin Polymers 0.000 description 1
- 229940088594 vitamin Drugs 0.000 description 1
- 235000013343 vitamin Nutrition 0.000 description 1
- 239000011782 vitamin Substances 0.000 description 1
- 229930003231 vitamin Natural products 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 239000007762 w/o emulsion Substances 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 229920001285 xanthan gum Polymers 0.000 description 1
- 235000010493 xanthan gum Nutrition 0.000 description 1
- 239000000230 xanthan gum Substances 0.000 description 1
- 229940082509 xanthan gum Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000000811 xylitol Substances 0.000 description 1
- 235000010447 xylitol Nutrition 0.000 description 1
- HEBKCHPVOIAQTA-SCDXWVJYSA-N xylitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)CO HEBKCHPVOIAQTA-SCDXWVJYSA-N 0.000 description 1
- 229960002675 xylitol Drugs 0.000 description 1
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 229940105125 zinc myristate Drugs 0.000 description 1
- XOOUIPVCVHRTMJ-UHFFFAOYSA-L zinc stearate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O XOOUIPVCVHRTMJ-UHFFFAOYSA-L 0.000 description 1
- UHVMMEOXYDMDKI-JKYCWFKZSA-L zinc;1-(5-cyanopyridin-2-yl)-3-[(1s,2s)-2-(6-fluoro-2-hydroxy-3-propanoylphenyl)cyclopropyl]urea;diacetate Chemical compound [Zn+2].CC([O-])=O.CC([O-])=O.CCC(=O)C1=CC=C(F)C([C@H]2[C@H](C2)NC(=O)NC=2N=CC(=CC=2)C#N)=C1O UHVMMEOXYDMDKI-JKYCWFKZSA-L 0.000 description 1
- GBFLQPIIIRJQLU-UHFFFAOYSA-L zinc;tetradecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCC([O-])=O GBFLQPIIIRJQLU-UHFFFAOYSA-L 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- FYGDTMLNYKFZSV-BYLHFPJWSA-N β-1,4-galactotrioside Chemical compound O[C@@H]1[C@@H](O)[C@H](O)[C@@H](CO)O[C@H]1O[C@@H]1[C@H](CO)O[C@@H](O[C@@H]2[C@@H](O[C@@H](O)[C@H](O)[C@H]2O)CO)[C@H](O)[C@H]1O FYGDTMLNYKFZSV-BYLHFPJWSA-N 0.000 description 1
Classifications
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
- A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
- A61K8/89—Polysiloxanes
- A61K8/895—Polysiloxanes containing silicon bound to unsaturated aliphatic groups, e.g. vinyl dimethicone
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L43/00—Compositions of homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing boron, silicon, phosphorus, selenium, tellurium or a metal; Compositions of derivatives of such polymers
- C08L43/04—Homopolymers or copolymers of monomers containing silicon
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F230/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal
- C08F230/04—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal
- C08F230/08—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and containing phosphorus, selenium, tellurium or a metal containing a metal containing silicon
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K8/00—Cosmetics or similar toiletry preparations
- A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
- A61K8/30—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds
- A61K8/33—Cosmetics or similar toiletry preparations characterised by the composition containing organic compounds containing oxygen
- A61K8/34—Alcohols
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q19/00—Preparations for care of the skin
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/14—Methyl esters, e.g. methyl (meth)acrylate
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F6/00—Post-polymerisation treatments
- C08F6/001—Removal of residual monomers by physical means
- C08F6/003—Removal of residual monomers by physical means from polymer solutions, suspensions, dispersions or emulsions without recovery of the polymer therefrom
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/05—Alcohols; Metal alcoholates
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
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- A—HUMAN NECESSITIES
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- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/10—General cosmetic use
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
- A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
- A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
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- A61K2800/544—Dendrimers, Hyperbranched polymers
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- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q17/00—Barrier preparations; Preparations brought into direct contact with the skin for affording protection against external influences, e.g. sunlight, X-rays or other harmful rays, corrosive materials, bacteria or insect stings
- A61Q17/04—Topical preparations for affording protection against sunlight or other radiation; Topical sun tanning preparations
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- A—HUMAN NECESSITIES
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- A61Q5/00—Preparations for care of the hair
- A61Q5/12—Preparations containing hair conditioners
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- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
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- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Dispersion Chemistry (AREA)
- Dermatology (AREA)
- Emergency Medicine (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Cosmetics (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Silicon Polymers (AREA)
Description
(a2) (a1)成分とは異なる、ラジカル重合性のビニル基を有する不飽和単量体に、
重合開始剤を添加してラジカル重合反応を行う工程を有し、かつ、
工程(I):ラジカル重合反応における最初の重合開始剤添加から少なくとも2時間後に、(Ia)最初に添加した重合開始剤と同一または異なる重合開始剤をさらに添加する工程を有する、共重合体の製造方法である。
工程(II):工程(I)の後、常圧または減圧下、系中に残存する未反応の不飽和単量体または飽和単量体を留去する工程を有してもよい。
式(1):
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1~10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1~10の整数であり、
Li+1は、水素原子、炭素原子数1~10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1~10の整数である)の場合は、Li+1は水素原子、炭素原子数1~10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、aiは0~3の整数である)である}。
本発明にかかるにおけるカルボシロキサンデンドリマー構造を含有する共重合体は、本発明の未反応の不飽和単量体(a1)および当該未反応の不飽和単量体(a1)に由来する飽和単量体の含有量が、共重合体に対して2500ppm以下であることを特徴とする。好適には、これらのカルボシロキサンデンドリマー構造を有する単量体の含有量は、2400ppm以下であり、後述する製造法を用いることで、必要に応じて、2000ppm以下、1500ppm以下の含有量に低減した共重合体も製造可能であり、化粧料原料として、刺激性が懸念されるカルボシロキサンデンドリマー構造含有単量体の含有量が極めて少ない共重合体を得ることができる。
すなわち、本発明の共重合体組成物は、上記の特定の未反応単量体が低減された共重合体および、(C)アルコール類および(D)油剤から選ばれる1種類以上を含有する組成物である。本発明の第一の発明である共重合体を化粧料に配合する際には、溶媒に溶解した溶液や分散媒に分散した分散液、或いは粉体状、顆粒状、ブロック状などの固体の形態とすることができる。特に、本発明に係る共重合体は、1種類以上の(C)アルコール類および/または(D)油剤に溶解あるいは分散して、前記共重合体と、これらの分散媒を含有する共重合体組成物の形態で化粧料に配合することが好適である。
本発明にかかる共重合体はアルコール類に分散ないし溶解して使用してもよく、また、本発明の共重合体は化粧料の汎用成分であるアルコール類と一定の親和性を有するので、化粧料の配合処方として共存させることもできる。アルコール類としては、1種又は2種以上の多価アルコール及び/又は低級一価アルコールを用いることができる。低級アルコールとしては、エタノール、イソプロパノール、n-プロパノール、t-ブタノール、sec-ブタノール等が例示され、エタノールが好ましい。多価アルコールとしては、1,3-プロパンジオール、1,3-ブチレングリコール、1,2-ブチレングリコール、プロピレングリコール、トリメチレングリコール、テトラメチレングリコール、2,3-ブチレングリコール、ペンタメチレングリコール、2-ブテン-1,4-ジオール、ジブチレングリコール、ペンチルグリコール、ヘキシレングリコール、オクチレングリコール等の2価アルコール、グリセリン、トリメチロールプロパン、1,2,6-ヘキサントリオール等の3価アルコール、ペンタエリスリトール、キシリトール等の4価以上の多価アルコール、ソルビトール、マンニトール、マルチトール、マルトトリオース、ショ糖、エリトリトール、グルコース、フルクトース、デンプン分解物、マルトース、キシリトース、デンプン分解糖還元アルコール等の糖アルコールが挙げられる。更に、これら低分子多価アルコールのほかに、ジエチレングリコール、ジプロピレングリコール、トリエチレングリコール、ポリプロピレングリコール、テトラエチレングリコール、ジグリセリン、ポリエチレングリコール、トリグリセリン、テトラグリセリン、ポリグリセリン等の多価アルコール重合体等が例示される。中でも、エタノール、1,3-プロパンジオール、1,3-ブチレングリコール、ソルビトール、ジプロピレングリコール、グリセリン、ポリエチレングリコールが特に好ましい。これらのアルコール類のうち、イソプロパノール等は上述の反応溶媒としても使用可能であるので、これらのアルコール類を含む重合反応組成物は、そのまま共重合体組成物として利用できる場合がある。
本発明にかかる共重合体は油剤に分散ないし溶解して使用してもよく、前記の油剤としては、化粧料一般に使用される動物油、植物油、合成油等が挙げられる。前記油剤は固体、半固形、液体のいずれでもよく、不揮発性、半揮発性、揮発性のいずれでもよい。油剤は、肌や毛髪に潤滑性を付与し、肌を柔軟にし、しっとり感を付与するために用いられる。また、油剤は、本発明の共重合体を希釈して共重合体組成物を得る目的でも使用することができ、特に、5~100℃で液状であり、(D1)シリコーン系油剤および(D2)有機系油剤から選択される少なくとも1種であることが好ましく、これらの油剤の種類、粘度等は化粧料の種類、用途に応じて、適宜選択することができる。これらの油剤は、上記共重合体組成物と同時に、本発明の化粧料に配合されるものである。
シリコーン系油剤は一般には疎水性であり、その分子構造は、直鎖状、環状、分岐状のいずれであってもよい。シリコーンオイル類の25℃における粘度は、通常、0.65~100,000mm2/sの範囲であり、0.65~10,000mm2/sの範囲が好ましい。また、当該シリコーン系油剤は揮発性を有しても良く、かつ、好ましい。
有機系油剤は、(D2-1)炭化水素油、(D2-2)脂肪酸エステル油、高級アルコール、高級脂肪酸、油脂、フッ素系油剤が代表的であり、本発明においては特に限定されるものではないが、有機系油剤は5~100℃で液状であることが好ましい。さらには、炭化水素油及び/又は脂肪酸エステル油が好ましい。これらは単独でも併用でもよく、前記シリコーン系油剤とも併用することができる。適切な油剤を組み合わせることにより、組成物および/または化粧料の経日安定性を高めるとともに、化粧料毎に求められる感触を付与することができる。前記シリコーン系油剤を配合することによりシリコーンオイル特有のさっぱりとした感触を付与することができ、さらに、揮発性の高い油剤を用いることで肌上にさっぱりした感触を付与することができ、またさらには炭化水素油及び/又は脂肪酸エステル油を前記シリコーン系油剤と併用することにより、肌や毛髪が潤うような保湿感(「しっとりした感触」ともいう)や滑らかな感触を付与することができる。
本発明は、上記共重合体を含有する化粧料に関する。ここで、上記の特定の未反応単量体が低減された共重合体を化粧料に配合する場合の配合量の好適範囲は既に述べたとおりであり、上記の特定の未反応単量体の含有量が100ppm以下の化粧料を設計乃至提供可能である。
本発明の共重合体または共重合体組成物を含有する化粧料は、さらに、粉体または着色剤、特に化粧品に用いられる任意の粉体(着色剤として用いられる粉体・顔料を含む)を配合することができる。粉体または着色剤は通常の化粧料に使用されるものであれば、その形状(球状、棒状、針状、板状、シート状、不定形状、紡錘状、お椀状、ラズベリー状等)や粒子径(煙霧状、微粒子、顔料級等)、粒子構造(多孔質、無孔質、二次凝集等)を問わず、いずれのものも使用することができるが、これらの粉体及び/または着色剤を顔料として配合する場合、平均粒子径が1nm~20μmの範囲にある無機顔料粉体、有機顔料粉体、樹脂粉体から選択される1種類又は2種類以上を配合することが好ましい。
ゲル化剤としては油溶性のものが好ましく、ゲル化または増粘効果を有する。具体的にはアルミニウムステアレート、マグネシウムステアレート、ジンクミリステート等の金属セッケン、N-ラウロイル-L-グルタミン酸、α、γ-ジ-n-ブチルアミン等のアミノ酸誘導体、デキストリンパルミチン酸エステル、デキストリンステアリン酸エステル、デキストリン2-エチルヘキサン酸パルミチン酸エステル等のデキストリン脂肪酸エステル、ショ糖パルミチン酸エステル、ショ糖ステアリン酸エステル等のショ糖脂肪酸エステル、モノベンジリデンソルビトール、ジベンジリデンソルビトール等のソルビトールのベンジリデン誘導体等が挙げられる。これらは必要に応じて一種、又は二種以上用いることができる。
有機変性粘土鉱物としては、例えば、ジメチルベンジルドデシルアンモニウムモンモリロナイトクレー、ジメチルジオクタデシルアンモニウムモンモリナイトクレー、ジメチルアルキルアンモニウムヘクトライト、ベンジルジメチルステアリルアンモニウムヘクトライト、塩化ジステアリルジメチルアンモニウム処理ケイ酸アルミニウムマグネシウム等が挙げられる。これらの市販品としては、ベントン27(ベンジルジメチルステアリルアンモニウムクロライド処理ヘクトライト: ナショナルレッド社製)、ベントン38(ジステアリルジメチルアンモニウムクロライド処理ヘクトライト: ナショナルレッド社製)等がある。
シリコーン樹脂は、高度の分岐状構造、網状構造又は籠状構造を有するオルガノポリシロキサンであり、常温で液状又は固形状であり、本発明の目的に反しない限り、通常化粧料に用いられるシリコーン樹脂であればいずれのものでもよい。固形状のシリコーン樹脂には、例えば、トリオルガノシロキシ単位(M単位)(オルガノ基はメチル基のみ、メチル基とビニル基若しくはフェニル基である)、ジオルガノシロキシ単位(D単位)(オルガノ基はメチル基のみ、メチル基とビニル基若しくはフェニル基である)、モノオルガノシロキシ単位(T単位)(オルガノ基はメチル基、ビニル基、又はフェニル基である)及びシロキシ単位(Q単位)の任意の組み合わせからなるMQ樹脂、MDQ樹脂、MTQ樹脂、MDTQ樹脂、TD樹脂、TQ樹脂、TDQ樹脂がある。さらには、トリメチルシロキシケイ酸、ポリアルキルシロキシケイ酸、ジメチルシロキシ単位含有トリメチルシロキシケイ酸、アルキル(パーフルオロアルキル)シロキシケイ酸が例示される。これらのシリコーン樹脂は油溶性であり、D4やD5に溶解しうるものが特に好ましい。
本発明においては、1,000,000mm2/s以上の、シリコーンガムと称される、超高粘度のオルガノポリシロキサンもシリコーン油として使用することができる。シリコーンガムは、超高重合度の直鎖状ジオルガノポリシロキサンであり、シリコーン生ゴムやオルガノポリシロキサンガムとも称されている。シリコーンガムは、その重合度が高いため、測定可能な程度の可塑度を有する点で、前記の油状シリコーン類と区別される。このようなシリコーン生ゴムとしては、ジアルキルシロキシ単位(D単位)を有する置換又は非置換のオルガノポリシロキサン、例えばジメチルポリシロキサン、メチルフェニルポリシロキサン、アミノポリシロキサン、メチルフロロアルキルポリシロキサン等、または、それらの微架橋構造を有したもの等が挙げられ、代表例として、一般式:R10(CH3)2SiO{(CH3)2SiO}s{(CH3)R11SiO}tSi(CH3)2R10(式中、R11はビニル基、フェニル基、炭素数が6~20のアルキル基、炭素数3~15のアミノアルキル基、炭素数3~15のパーフロロアルキル基、炭素数3~15の4級アンモニウム塩基含有アルキル基から選択される基であり、末端基R10は、炭素数1~8のアルキル基、フェニル基、ビニル基、炭素数3~15のアミノアルキル基、水酸基及び炭素数1~8のアルコキシ基から選択される基である。また、s=2,000~6,000、t=0~1,000、s+t=2,000~6,000)で示されるものがある。中でも、重合度3000~20000のジメチルポリシロキサン生ゴムが好ましい。これらのシリコーンガムは、そのまま、或いは油状シリコーンに分散させた液状のガムディスパージョン(シリコーンガムのオイル分散物)として、本発明にかかる化粧料に配合することができる。
シリコーンエラストマーは、その目的に応じて任意の形態で化粧料に配合することが可能であるが、特に、前記の「(E)粉体」にて説明したシリコーンエラストマー粉体のほか、架橋性オルガノポリシロキサンとして配合することが好ましい。シリコーンエラストマー粉体は水分散液の形態としても、本発明の化粧料で使用することができる。このような水分散液の市販品としては、例えば東レ・ダウコーニング社製のBY 29-129,PF-2001 PIF Emulsion等が挙げられる。これらのシリコーンエラストマー粉末の水系分散体(=サスペンジョン)を配合することにより、本発明の化粧料の使用感をさらに改善することができる点で極めて有用である。
有機変性シリコーンは、親油性であるものが好ましい。具体的には、前記の他、アミノ変性シリコーン、アミノポリエーテル変性シリコーン、エポキシ変性シリコーン、カルボキシル変性シリコーン、アミノ酸変性シリコーン、カルビノール変性シリコーン、アクリル変性シリコーン、フェノール変性シリコーン、アミドアルキル変性シリコーン、アミノグリコール変性シリコーン、アルコキシ変性シリコーンを挙げることができる。該有機変性シリコーン類は、主鎖としてポリシロキサン結合の他に、アルキレン鎖、アミノアルキレン鎖又は化合物が親水性を有さない程度のポリエーテル鎖を有するものであってもよく、有機変性基は、ポリシロキサン鎖の側鎖又は末端の一方又は両方に有するものであってよい。本発明の化粧料を毛髪化粧料として使用する場合、アミノ変性シリコーン、カルビノール変性シリコーン、アミノポリエーテル変性シリコーン又はアミノグリコール変性シリコーンを好適に用いることができ、3-アミノプロピル基、N-(2-アミノエチル)3-アミノプロピル基等を有するアミノ変性シリコーンが一般的なものとして例示できる。
紫外線防御成分には、無機系の紫外線防御成分と有機系の紫外線防御成分がある。本発明の化粧料が日焼け止め化粧料であれば、少なくとも1種の無機系又は有機系、特に有機系の紫外線防御成分を含有することが好ましい。本願発明の共重合体は、一般に難溶性の有機系の紫外線防御成分、例えば、「ユビナールA」として知られるジエチルアミノヒドロキシベンゾイル安息香酸ヘキシル、「チノソーブS」として知られるビスエチルヘキシルオキシフェノールメトキシフェニルトリアジン、「オクトクリレン」として知られる2-シアノ-3、3-ジフェニルプロパ-2-エン酸2-エチルヘキシルエステル、その他桂皮酸系紫外線吸収剤などとの相溶性に優れ、本願発明の共重合体との配合安定性を改善することができる。
一方、本発明の化粧料は、水溶性の成分を多く含む水性またはエマルジョン型の化粧料であってもよく、その剤形に応じて(N)水溶性高分子を配合することもでき、かつ好ましい。水溶性高分子としては、1種又は2種以上の水溶性高分子を用いることができる。天然の水溶性高分子としては、例えば、アラビアガム、トラガカントガム、ガラクタン、グアーガム、キャロブガム、カラヤガム、カラギーナン、ペクチン、カンテン、クインスシード(マルメロ)、アルゲコロイド(カッソウエキス)、デンプン(コメ、トウモロコシ、バレイショ、コムギ)、グリチルリチン酸等の植物系高分子、キサンタンガム、デキストラン、サクシノグルカン、プルラン等の微生物系高分子、コラーゲン、カゼイン、アルブミン、ゼラチン等の動物系高分子が挙げられる。また、半合成の水溶性高分子としては、例えば、カルボキシメチルデンプン、メチルヒドロキシプロピルデンプン等のデンプン系高分子、メチルセルロース、ニトロセルロース、エチルセルロース、メチルヒドロキシプロピルセルロース、ヒドロキシエチルセルロース、セルロース硫酸ナトリウム、ヒドロキシプロピルセルロース、カルボキシメチルセルロースナトリウム(CMC)、結晶セルロース、セルロース末等のセルロース系高分子、アルギン酸ナトリウム、アルギン酸プロピレングリコールエステル等のアルギン酸系高分子が挙げられる。合成の水溶性高分子としては、例えば、ポリビニルアルコール、ポリビニルメチルエーテル系高分子、ポリビニルピロリドン、カルボキシビニルポリマー(CARBOPOL 940, 941; BF Goodrich社)等のビニル系高分子、ポリエチレングリコール20,000、ポリエチレングリコール6,000、ポリエチレングリコール4,000等のポリオキシエチレン系高分子、ポリオキシエチレンポリオキシプロピレン共重合体、PEG/PPGメチルエーテル等の共重合体系高分子、ポリアクリル酸ナトリウム、ポリエチルアクリレート、ポリアクリルアミド等のアクリル系高分子、ポリエチレンイミン、カチオンポリマー等が例示される。その他のカチオン性水溶性高分子としては、特に、毛髪化粧料に好適に配合できる成分として、第4級窒素変性ポリサッカライド(例えば、カチオン変性セルロース、カチオン変性ヒドロキシエチルセルロース、カチオン変性グアーガム、カチオン変性ローカストビーンガム、カチオン変性デンプン等)、塩化ジメチルジアリルアンモニウム誘導体(例えば、塩化ジメチルジアリルアンモニウム・アクリルアミド共重合体、ポリ塩化ジメチルメチレンピペリジニウム等)、ビニルピロリドン誘導体(例えば、ビニルピロリドン・ジメチルアミノエチルメタクリル酸共重合体塩、ビニルピロリドン・メタクリルアミドプロピルトリメチルアンモニウムクロライド共重合体、ビニルピロリドン・塩化メチルビニルイミダゾリウム共重合体等)が例示できる。
また、化粧料の種類およびその製剤の形態も特に限定されるものではなく、スキンケア製品、制汗剤製品、脱臭剤製品、メイクアップ製品、紫外線防御製品などの皮膚用化粧品、睫毛化粧料製品、毛髪用洗浄剤製品、整髪料製品、毛髪用着色料製品、養毛料製品、ヘアリンス製品、ヘアコンディショナー製品、ヘアトリートメント製品等の頭髪用化粧品;浴用化粧品等の毛髪化粧料製品であってよい。また、その形態は特に限定されないが、溶液状、乳液状、クリーム状、固形状、半固形状、ペースト状、ゲル状、粉末状、多層状、ムース状、油中水型或いは水中油型の乳化組成物(エマルジョン組成物)のいずれであってもよい。
本発明にかかる化粧料は、上記の共重合体を含むので、撥水性に優れ、かつ、持続性および皮脂耐久性に優れた皮膜を皮膚又は毛髪上に形成することができる。特に、本発明に係る共重合体は、刺激性が懸念され、かつ、通常の留去手段では共重合体からの分離や除去が困難な性質を有するカルボシロキサンデンドリマー構造を含有する単量体の含有量が極めて少なく、かつ、耐水性および耐皮脂性に優れる皮膜を肌または髪上に形成可能であり、刺激性の問題なく、これらの機能性皮膜を与える化粧料を設計可能である。
本発明に係る共重合体は、刺激性が懸念され、かつ、通常の留去手段では共重合体からの分離や除去が困難な性質を有するカルボシロキサンデンドリマー構造を含有する単量体の含有量が極めて少ないほかは、公知のアクリルシリコーンデンドリマーコポリマーと同様の撥水性、洗浄性、皮膜形成性などの特性を備えている。このため、例えば、特許第4009382号公報(特開2000-063225号公報)等中に記載されている、カルボシロキサンデンドリマー構造を側鎖に有するビニル系重合体等について公知の処方において、その一部または全部を置き換えて使用することができる。すなわち、公知のカルボシロキサンデンドリマー構造を側鎖に有するビニル系重合体を含む化粧料処方について、本発明に係る共重合体により対応するビニル系重合体を置換して化粧料処方を設計乃至製造することは、本件出願人がここに明確に教示するものである。
本発明に係る共重合体皮膜形成剤として、化粧料以外にも用いることができる。すなわち、皮膜に撥水効果や撥油効果や均一性(integrity)や強度や擦れ耐性が求められるような用途であれば分野に限らず用いることができる。特に、塗料組成物や繊維への撥水効果付与剤や無機材料・有機材料の処理剤などにも用いることが可能である。また、本発明の皮膜形成剤は必要であれば、水性環境下において用いることができるため、取り扱いも容易である。
前記のとおり、本発明に係る共重合体の原料であるカルボシロキサンデンドリマー構造を含有する単量体は、通常の留去手段では共重合体からの分離や除去が困難な性質を有する。しかしながら、本発明に係る共重合体の製造方法により、当該単量体を共重合体に対して2500ppm以下に低減可能である。さらに、以下の工程(I)を有する製造方法により、ラジカル重合反応に要する反応時間を短縮し、工業的生産効率を改善することができる。
(a1)ラジカル重合可能な有機基を有するカルボシロキサンデンドリマー構造を有する不飽和単量体と、
(a2) (a1)成分とは異なる、ラジカル重合性のビニル基を有する不飽和単量体に、
重合開始剤を添加してラジカル重合反応を行う工程を有し、かつ、
工程(I):ラジカル重合反応における最初の重合開始剤添加から少なくとも2時間後に、(Ia)最初に添加した重合開始剤と同一または異なる重合開始剤をさらに添加する工程を有することを特徴とする。当該製造方法は、前記の工程(I)において、任意で、(Ib)常圧(1atm)での沸点が160℃未満のラジカル重合性のビニル基を有する単量体(a2´)を添加して、未反応の(a1)成分のラジカル重合反応を進める工程を有してもよく、さらに、工程(II):工程(I)の後、常圧または減圧下、系中に残存する未反応の不飽和単量体または飽和単量体を留去する工程を有してもよく、かつ、好ましい。
[GPCピークトップ分子量]
溶出溶媒にトルエンを、カラムにTSKgel Multipore HXL-Mを用いてGPC分析し、標準ポリスチレンによる検量線を用いて分子量を求めた。
[残存カルボシロキサンデンドリマーモノマー(A-1)定量]
高速液体クロマトグラフィー(島津製作所 Prominence-i LC-2030C3D、カラム:Atlantis T3 - 3μm (3.0 x 100mm)、紫外線可視吸収検出部、溶出溶媒:水/メタノール/THFのグラジェントモード)で定量した。
[動粘度]
ウベローデ粘度管を用いて、25℃での組成物の粘度を測定した。
[不揮発分]
直径6cmのアルミ皿に試料を1g秤量し、150℃、1時間で加熱した後に残った試料から求めた。
[皮膜べたつき]
前記と同様にしてアルミ皿上に作成した皮膜に指で触れたとき、皮膜と一体化したアルミ皿が持ち上がるかどうかで判別した。
[接触角(水)]
ビニル系共重合体のIPA溶液をガラスプレート上に塗布後、室温にて溶媒を乾燥除去してビニル系重合体の塗膜を得た。この塗膜表面に水滴5μLを載せて、水に対する接触角を測定した。測定装置は、Drop shape analysis system (KRUSS DSA10 Mk-2)を用い、n=5以上の平均値を求めた。
[接触角(人工皮脂)]
ビニル系共重合体のIPA溶液をガラスプレート上に塗布後、室温にて溶媒を乾燥除去してビニル系重合体の塗膜を得た。この塗膜表面に人工皮脂(トリオレイン:オレイン酸:スクワラン=3:1:1の混合物)の液滴5μLを載せて、人工皮脂に対する接触角を測定した。測定装置は、Drop shape analysis system (KRUSS DSA10 Mk-2)を用い、n=5以上の平均値を求めた。
[共重合体およびその液状組成物の調製]
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、イソプロピルアルコール(IPA)を163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、下記式(A-1):
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、カルボシロキサンデンドリマーモノマー(A-1)80g(40重量%)、V-601を2g(1重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、1時間かけて滴下した。滴下終了後、窒素雰囲気下8時間加熱攪拌し、不揮発分40.6%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量23,600のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が30,750ppm残存していることがわかった。
参考例1のV-601の量を4.4g(2.2重量%)にする以外は同様に操作し、反応生成物を得た。GPCで分析したところ、ピークトップ分子量16,000のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が11,000ppm残存していることがわかった。
参考例1のV-601の量を8.8g(4.4重量%)にする以外は同様に操作し、反応生成物を得た。GPCで分析したところ、ピークトップ分子量12,600のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が2,250ppm残存していることがわかった。
以上の結果を表1にまとめた。実施例1と参考例2との比較、そして参考例1~3の比較から、最初に加える重合開始剤V-601の量によってポリマー分子量が決定されることがわかった。また、重合開始剤V-601を時間差を置いて追加添加することにより、反応性の悪いカルボシロキサンデンドリマーモノマー(A-1)の残存量を著しく低減することができた。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、カルボシロキサンデンドリマーモノマー(A-1)80g(40重量%)、V-601を4.4g(2.2重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、1時間かけて滴下した。滴下終了後、窒素雰囲気下6時間加熱攪拌し、V-601 0.6g(0.3重量%)をIPA 30gに溶解させた溶液を加えた。さらに6時間攪拌の後、不揮発分40.0%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量17,200のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が2,350ppm残存していることがわかった。
参考例1のV-601の量を4.4g(2.2重量%)、加熱攪拌の時間を12時間にする以外は同様に操作し、反応生成物を得た。GPCで分析したところ、ピークトップ分子量17,000のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が5,200ppm残存していることがわかった。
参考例1のV-601の量を4.4g(2.2重量%)、加熱攪拌の時間を24時間にする以外は同様に操作し、反応生成物を得た。GPCで分析したところ、ピークトップ分子量18,000のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が2,740ppm残存していることがわかった。
以上の結果を表2にまとめた。開始剤を追加することによって、反応性の悪いカルボシロキサンデンドリマーモノマー(A-1)の残存量を減らすことができるだけでなく、反応時間も大幅に短縮できることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、カルボシロキサンデンドリマーモノマー(A-1)80g(40重量%)、1,1,3,3-テトラメチルブチルパーオキシ-2-エチルヘキサノエート(パーオクタO、日油株式会社製)を4.4g(2.2重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、1時間かけて滴下した。滴下終了後、窒素雰囲気下4時間加熱攪拌し、パーオクタ(登録商標)O(1,1,3,3-テトラメチルブチルペルオキシ-2-エチルヘキサノエート) 4.4g(2.2重量%)をIPA 30gに溶解させた溶液を加えた。さらに4時間攪拌の後、反応生成物を得た。GPCで分析したところ、ピークトップ分子量19,400のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が1,350ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、カルボシロキサンデンドリマーモノマー(A-1)80g(40重量%)、パーオクタOを4.4g(2.2重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、1時間かけて滴下した。滴下終了後、窒素雰囲気下6時間加熱攪拌し、パーオクタ(登録商標)O(1,1,3,3-テトラメチルブチルペルオキシ-2-エチルヘキサノエート) 0.6g(0.3重量%)をIPA 30gに溶解させた溶液を加えた。さらに6時間攪拌の後、反応生成物を得た。GPCで分析したところ、ピークトップ分子量18,700のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が1,320ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート110g(55重量%)、n-ブチルアクリレート10g(5重量%)、カルボシロキサンデンドリマーモノマー(A-1)80g(40重量%)、パーオクタOを4.4g(2.2重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、1時間かけて滴下した。滴下終了後、窒素雰囲気下12時間加熱攪拌し、反応生成物を得た。GPCで分析したところ、ピークトップ分子量17,000のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が9.580ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、75℃に加熱した。滴下ロートにメチルメタクリレート76g(38重量%)、n-ブチルアクリレート24g(12重量%)、カルボシロキサンデンドリマーモノマー(A-1)100g(50重量%)、V-601を2g(1重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を75℃に保ったまま、3時間かけて滴下した。滴下終了後、窒素雰囲気下4時間加熱攪拌し、V-601 8g(4重量%)をIPA 30gに溶解させた溶液と、n-ブチルアクリレート0.6g(0.3重量%)を加えた。さらに6時間攪拌の後、不揮発分40.0%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量23,100のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が1,380ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート76g(38重量%)、n-ブチルアクリレート24g(12重量%)、カルボシロキサンデンドリマーモノマー(A-1)100g(50重量%)、V-601を2g(1重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、3時間かけて滴下した。滴下終了後、窒素雰囲気下4時間加熱攪拌し、V-601 8g(4重量%)をIPA 30gに溶解させた溶液と、n-ブチルアクリレート0.6g(0.3重量%)を加えた。さらに2時間攪拌の後、不揮発分39.8%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量28,900のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が2,240ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート76g(38重量%)、n-ブチルアクリレート24g(12重量%)、カルボシロキサンデンドリマーモノマー(A-1)100g(50重量%)、V-601を2g(1重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、3時間かけて滴下した。滴下終了後、窒素雰囲気下1時間加熱攪拌し、V-601 2g(1重量%)をIPA 30gに溶解させた溶液を加えた。さらに2時間攪拌の後、不揮発分40.7質量%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量28,400のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が4,320ppm残存していることがわかった。
攪拌装置,温度計,還流管を取り付けた1リットル4つ口フラスコに、IPAを163g仕込み、窒素ガスでバブリングを行い十分に脱気し、70℃に加熱した。滴下ロートにメチルメタクリレート76g(38重量%)、n-ブチルアクリレート24g(12重量%)、カルボシロキサンデンドリマーモノマー(A-1)100g(50重量%)、V-601を2g(1重量%)、IPAを107g仕込み、溶解させた。窒素雰囲気下、滴下ロートよりモノマー混合物を70℃に保ったまま、3時間かけて滴下した。滴下終了後、窒素雰囲気下7時間加熱攪拌し、不揮発分40.9質量%の反応生成物を得た。GPCで分析したところ、ピークトップ分子量29,300のポリマーであることがわかった。また、高速液体クロマトグラフィーで分析したところ、カルボシロキサンデンドリマーモノマー(A-1)が14,750ppm残存していることがわかった。
以上の結果を表4にまとめた。組成の異なるモノマーの重合では、重合開始剤とともに低分子モノマーを一緒に追加することで反応性の悪いカルボシロキサンデンドリマーモノマー(A-1)の残存量をさらに減らすことができた。
以下、上記の実施例により得た重合体について、油剤(イソドデカン等)により反応溶媒を置換して、液状の共重合体組成物を得た。その詳細および性状を表5にまとめた。なお、不揮発分は、各実施例におけるカルボシロキサンデンドリマー構造を有するビニル共重合体であり、これらの液状の共重合体組成物中における(A-1)成分の含有量は
1000ppm以下に低減されている。
実施例1のビニル系重合体のイソプロピルアルコール溶液200gにイソドデカン(マルカゾールR、丸善石油製)120g加えた後、120℃でIPAを留出させた。減圧下、未反応単量体を留出させ、液状組成物を得た。不揮発分は37.0質量%、動粘度は27mm2/sであった。接触角(水)は105°、接触角(人工皮脂)は52°であり、また、皮膜にべたつきもなく、化粧料用皮膜剤として有用であった。
実施例2のビニル系重合体のイソプロピルアルコール溶液200gにマルカゾールRを120g加えた後、120℃でIPAを留出させた。減圧下、未反応単量体を留出させ、液状組成物を得た。不揮発分は40.5質量%、動粘度は66mm2/sであった。
実施例3のビニル系重合体のイソプロピルアルコール溶液200gにマルカゾールRを120g加えた後、120℃でIPAを留出させた。減圧下、未反応単量体を留出させ、液状組成物を得た。不揮発分は41.6質量%、動粘度は172mm2/sであった。
実施例5のビニル系重合体のイソプロピルアルコール溶液200gにドデカン(PARAFOL 12-97、サソール社製)を120g加えた後、120℃でIPAを留出させた。減圧下、未反応単量体を留出させ、液状組成物を得た。不揮発分は39.4質量%、動粘度は76mm2/sであった。接触角(水)は113°、接触角(人工皮脂)は59°であり、また、皮膜にべたつきもなく、化粧料用皮膜剤として有用であった。
実施例5のビニル系重合体のイソプロピルアルコール溶液200gにウンデカンとトリデカンの混合液(CETIOL ULTIMATE、BASF社製)を120g加えた後、120℃でIPAを留出させた。減圧下、未反応単量体を留出させ、液状組成物を得た。不揮発分は37.6質量%、動粘度は49mm2/sであった。接触角(水)は109°、接触角(人工皮脂)は51°であり、また、皮膜にべたつきもなく、化粧料用皮膜剤として有用であった。
Claims (7)
- (a1)ラジカル重合可能な有機基を有するカルボシロキサンデンドリマー構造を有する不飽和単量体と、
(a2) (a1)成分とは異なる、ラジカル重合性のビニル基を有する不飽和単量体
の共重合体であり、未反応の不飽和単量体(a1)および当該未反応の不飽和単量体(a1)に由来する飽和単量体の含有量が、共重合体に対して2500ppm以下である、共重合体の製造方法であって、
(a1)ラジカル重合可能な有機基を有するカルボシロキサンデンドリマー構造を有する不飽和単量体と、
(a2) (a1)成分とは異なる、ラジカル重合性のビニル基を有する不飽和単量体に、
重合開始剤を添加してラジカル重合反応を行う工程を有し、かつ、
工程(I):ラジカル重合反応における最初の重合開始剤添加から少なくとも2時間後に、(Ia)最初に添加した重合開始剤と同一または異なる重合開始剤をさらに添加する工程
を有する、共重合体の製造方法。 - 共重合体を構成する (a1)成分および(a2)成分の全質量に対して、上記の(a1)成分の質量%が20質量%以上であることを特徴とする、請求項1に記載の共重合体の製造方法。
- (a1)成分が、式(1)で示されるカルボシロキサンデンドリマー構造を有する不飽和単量体である、請求項1または請求項2に記載の共重合体の製造方法。
式(1):
Zは、2価の有機基であり、
pは、0又は1であり、
R1及びR2は、それぞれ独立して、炭素原子数1~10のアルキル基、アリール基又はアラルキル基であり、
L1は、i=1とした場合の下記式(2)で示されるシリルアルキル基
Z及びpは、前記と同じであり、
R1及びR2は、前記と同じであり、
iは、前記シリルアルキル基の総階層数を示す1~10の整数であり、
Li+1は、水素原子、炭素原子数1~10のアルキル基、アリール基、アラルキル基及び前記シリルアルキル基からなる群から選択される基であり、但し、i=c(cは前記シリルアルキル基の階層を示す1~10の整数である)の場合は、Li+1は水素原子、炭素原子数1~10のアルキル基、アリール基又はアラルキル基であり、i<cの場合は前記シリルアルキル基であり、aiは0~3の整数である)である}。 - 前記の工程(I)が、さらに、(Ib)常圧(1atm)での沸点が160℃未満のラジカル重合性のビニル基を有する単量体(a2´)を添加して、未反応の(a1)成分のラジカル重合反応を進める工程
を含む、請求項1~請求項3のいずれか1項に記載の共重合体の製造方法。 - さらに、工程(II):工程(I)の後、常圧または減圧下、系中に残存する未反応の不飽和単量体または飽和単量体を留去する工程
を有する、請求項1~請求項4のいずれか1項に記載の共重合体の製造方法。 - さらに、工程(III):系中に残存する未反応の不飽和単量体に対して水素添加反応を行い、不飽和単量体を飽和単量体に転換する工程を含む、請求項1~請求項5のいずれか1項に記載の共重合体の製造方法。
- さらに、工程(IV):系中に1種類以上の(C)アルコール類および/または(D)油剤を添加し、ラジカル重合反応における反応溶媒を除去する工程を含む、請求項1~請求項6のいずれか1項に記載の共重合体の製造方法。
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