JP5841347B2 - 新規なオルガノポリシロキサン、それを含む界面活性剤、エマルジョン組成物、粉体処理剤、油性原料の増粘剤、ゲル化剤、ゲル状組成物、化粧料用原料並びに、これらを含む外用剤及び化粧料 - Google Patents
新規なオルガノポリシロキサン、それを含む界面活性剤、エマルジョン組成物、粉体処理剤、油性原料の増粘剤、ゲル化剤、ゲル状組成物、化粧料用原料並びに、これらを含む外用剤及び化粧料 Download PDFInfo
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- JP5841347B2 JP5841347B2 JP2011102362A JP2011102362A JP5841347B2 JP 5841347 B2 JP5841347 B2 JP 5841347B2 JP 2011102362 A JP2011102362 A JP 2011102362A JP 2011102362 A JP2011102362 A JP 2011102362A JP 5841347 B2 JP5841347 B2 JP 5841347B2
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- silicone
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- 229910052902 vermiculite Inorganic materials 0.000 description 1
- 235000019354 vermiculite Nutrition 0.000 description 1
- 235000019156 vitamin B Nutrition 0.000 description 1
- 239000011720 vitamin B Substances 0.000 description 1
- 235000019163 vitamin B12 Nutrition 0.000 description 1
- 239000011715 vitamin B12 Substances 0.000 description 1
- 235000019164 vitamin B2 Nutrition 0.000 description 1
- 239000011716 vitamin B2 Substances 0.000 description 1
- 235000019158 vitamin B6 Nutrition 0.000 description 1
- 239000011726 vitamin B6 Substances 0.000 description 1
- 235000011912 vitamin B7 Nutrition 0.000 description 1
- 239000011735 vitamin B7 Substances 0.000 description 1
- 235000019154 vitamin C Nutrition 0.000 description 1
- 239000011718 vitamin C Substances 0.000 description 1
- 235000019166 vitamin D Nutrition 0.000 description 1
- 239000011710 vitamin D Substances 0.000 description 1
- 150000003710 vitamin D derivatives Chemical class 0.000 description 1
- 235000001892 vitamin D2 Nutrition 0.000 description 1
- 239000011653 vitamin D2 Substances 0.000 description 1
- MECHNRXZTMCUDQ-RKHKHRCZSA-N vitamin D2 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)/C=C/[C@H](C)C(C)C)=C\C=C1\C[C@@H](O)CCC1=C MECHNRXZTMCUDQ-RKHKHRCZSA-N 0.000 description 1
- 235000005282 vitamin D3 Nutrition 0.000 description 1
- 239000011647 vitamin D3 Substances 0.000 description 1
- QYSXJUFSXHHAJI-YRZJJWOYSA-N vitamin D3 Chemical compound C1(/[C@@H]2CC[C@@H]([C@]2(CCC1)C)[C@H](C)CCCC(C)C)=C\C=C1\C[C@@H](O)CCC1=C QYSXJUFSXHHAJI-YRZJJWOYSA-N 0.000 description 1
- 229940046009 vitamin E Drugs 0.000 description 1
- 235000019165 vitamin E Nutrition 0.000 description 1
- 239000011709 vitamin E Substances 0.000 description 1
- 229940046008 vitamin d Drugs 0.000 description 1
- 229940021056 vitamin d3 Drugs 0.000 description 1
- 239000004636 vulcanized rubber Substances 0.000 description 1
- 235000020234 walnut Nutrition 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
- 125000005023 xylyl group Chemical group 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000001052 yellow pigment Substances 0.000 description 1
- 229940098697 zinc laurate Drugs 0.000 description 1
- 229940012185 zinc palmitate Drugs 0.000 description 1
- 229940057977 zinc stearate Drugs 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
- GPYYEEJOMCKTPR-UHFFFAOYSA-L zinc;dodecanoate Chemical compound [Zn+2].CCCCCCCCCCCC([O-])=O.CCCCCCCCCCCC([O-])=O GPYYEEJOMCKTPR-UHFFFAOYSA-L 0.000 description 1
- GJAPSKMAVXDBIU-UHFFFAOYSA-L zinc;hexadecanoate Chemical compound [Zn+2].CCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCC([O-])=O GJAPSKMAVXDBIU-UHFFFAOYSA-L 0.000 description 1
- KUPGJMJHAFGISS-UHFFFAOYSA-L zinc;hexadecyl phosphate Chemical compound [Zn+2].CCCCCCCCCCCCCCCCOP([O-])([O-])=O KUPGJMJHAFGISS-UHFFFAOYSA-L 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
- 229910001928 zirconium oxide Inorganic materials 0.000 description 1
- 239000004711 α-olefin Substances 0.000 description 1
- 235000007680 β-tocopherol Nutrition 0.000 description 1
- 239000011590 β-tocopherol Substances 0.000 description 1
- 239000002478 γ-tocopherol Substances 0.000 description 1
- QUEDXNHFTDJVIY-DQCZWYHMSA-N γ-tocopherol Chemical compound OC1=C(C)C(C)=C2O[C@@](CCC[C@H](C)CCC[C@H](C)CCCC(C)C)(C)CCC2=C1 QUEDXNHFTDJVIY-DQCZWYHMSA-N 0.000 description 1
Classifications
-
- 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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/892—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by a hydroxy group, e.g. dimethiconol
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- A61Q1/00—Make-up preparations; Body powders; Preparations for removing make-up
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/04—Preparations containing skin colorants, e.g. pigments for lips
- A61Q1/06—Lipsticks
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/10—Preparations containing skin colorants, e.g. pigments for eyes, e.g. eyeliner, mascara
-
- A—HUMAN NECESSITIES
- 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
-
- 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
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/04—Polysiloxanes
- C08L83/06—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- 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
- A61K2800/10—General cosmetic use
-
- 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
- A61K2800/48—Thickener, Thickening system
-
- 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
- A61Q1/02—Preparations containing skin colorants, e.g. pigments
- A61Q1/08—Preparations containing skin colorants, e.g. pigments for cheeks, e.g. rouge
Landscapes
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Animal Behavior & Ethology (AREA)
- General Health & Medical Sciences (AREA)
- Public Health (AREA)
- Veterinary Medicine (AREA)
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Dermatology (AREA)
- Birds (AREA)
- Epidemiology (AREA)
- Cosmetics (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Silicon Polymers (AREA)
- Medicinal Preparation (AREA)
Description
R1は一価有機基(但し、R2及びQを除く)を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは下記一般式(2−1):
R3は二価有機基を表し、
dは1又は2である)、又は、下記一般式(2−2):
R3は上記のとおりであり、
d’は0又は1である)で表わされる糖アルコール基含有有機基であり、
a 、b 及びcは、それぞれ、1.0≦a≦2.5、0.0001≦b≦1.5、及び、0.0001≦c≦1.5の範囲にある数である}で表される共変性オルガノポリシロキサンによって達成される。
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは上記一般式(2−1)又は(2−2)で表される糖アルコール含有有機基であり、
Xは上記のR1、R2及びQで表される官能基のいずれかを表し、
a=0〜2000、b=0〜200、c=0〜50であり、b=0の場合、Xの少なくとも一つはR2で表される基である。また、c=0の場合、Xの少なくとも一つはQで表される基である。}で表されるものが好ましい。
R1がメチル基であり、
R2が炭素原子数10〜20の、置換若しくは非置換の、直鎖状若しくは分岐状のアルキル基であり、
更に、a+b+cが0〜1000の範囲であることを満たし、且つ
a=0〜1000、b=0〜200、c=0〜50の範囲の数(ただし、b=0の場合、Xの少なくとも一つはR2で表される基であり、c=0の場合、Xの少なくとも一つはQで表される基である。)であることがより好ましい。また、a+b+cが0〜500の範囲であることを満たし、且つ
a=0〜500、b=0〜150、c=0〜50の範囲の数(ただし、b=0の場合、Xの少なくとも一つはR2で表される基であり、c=0の場合、Xの少なくとも一つはQで表される基である。)であることが特に好ましい。
R1は一価有機基(但し、R2及びQを除く)を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは下記一般式(2−1):
R3は二価有機基を表し、
dは1又は2である)、又は、下記一般式(2−2):
R3は上記のとおりであり、
d’は0又は1である)で表わされる糖アルコール基含有有機基であり、
a 、b 及びcは、それぞれ、1.0≦a≦2.5、0.0001≦b≦1.5、及び、0.0001≦c≦1.5の範囲にある数である}で表されるものである。
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは上記一般式(2−1)又は(2−2)で表される糖アルコール含有有機基であり、
Xは上記のR1、R2及びQで表される官能基のいずれかを表し、
a=0〜2000、b=0〜200、c=0〜50であり、b=0の場合、Xの少なくとも一つはR2で表される基である。また、c=0の場合、Xの少なくとも一つはQで表される基である。なお、b=c=0の場合は、Xの一方がR2で表される基であり、他方がQで表される基であることが好ましい。}で表されるものが好ましい。R1としての一価有機基、及び、R2としての炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基の例は上記のとおりである。
R1がメチル基であり、
R2が炭素原子数10〜20の、置換若しくは非置換の、直鎖状若しくは分岐状のアルキル基であり、
更に、a+b+cが0〜1000の範囲であることを満たし、且つ、a=0〜1000、b=0〜150、c=0〜50の範囲の数(ただし、b=0の場合、Xの少なくとも一つはR2で表される基であり、c=0の場合、Xの少なくとも一つはQで表される基である。なお、b=c=0の場合は、Xの一方がR2で表される基であり、他方がQで表される基であることが好ましい。)であることがより好ましい。また、a+b+cが0〜500の範囲であることを満たし、且つ
a=0〜500、b=0〜150、c=0〜50の範囲の数(ただし、b=0の場合、Xの少なくとも一つはR2で表される基であり、c=0の場合、Xの少なくとも一つはQで表される基である。)であることが特に好ましい。
変性率(モル%)=(1分子あたりの珪素原子に結合した糖アルコール含有有機基の数)/{6+2×(a+b+c)}×100
で示される。例えば、1つの糖アルコール含有有機基を有するトリシロキサンからなる共変性オルガノポリシロキサンの場合には、8個の珪素原子結合官能基のうち、1個が糖アルコール含有有機基により変性されているから、糖アルコール含有有機基による変性率は、12.5モル%である。
R1は一価有機基を表し、
QH、QH1及びQH2は、それぞれ独立して、上記のR1又は水素原子を表し、
m1=0〜2000、好ましくは0〜1000、m2=0〜200、好ましくは0〜150、m3=0〜50、このましくは0〜25であり、m2=0又はm3=0の場合、QHの少なくとも一つは水素原子であり、m2+m3=0の場合、QHは共に水素原子である}で表されるオルガノハイドロジェンポリシロキサンと、下記一般式:
Z−R2’
(式中、Zは不飽和有機基を表し、
R2’は炭素原子数7〜28の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表す)で表されるモノ不飽和有機化合物、及び、下記一般式(2’−1):
Zは上記のとおりであり、
dは1又は2であり、好ましくは1である)で表される糖アルコールのモノ不飽和エーテル化合物、又は、下記一般式(2’−2):
Zは上記のとおりであり、
d’は0又は1であり、好ましくは0である)で表される糖アルコールのモノ不飽和エーテル化合物を、オルガノハイドロジェンポリシロキサン中の珪素結合水素原子に対し、それぞれ、1モル当量以上となる物質量で付加反応させることにより得ることができる。
本発明の共変性オルガノポリシロキサンは、各種粉体の親水性表面に配向して適度な撥水性を付与できるため、粉体処理剤、特に、粉体表面処理剤として好適に用いることができる。本発明の粉体処理剤中の前記共変性オルガノポリシロキサンの配合量は、粉体処理効果、特に、粉体表面処理効果、を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
本発明における「粉体」は、化粧料の成分として一般に使用されるものであり、白色及び着色顔料、並びに、体質顔料を含む。白色及び着色顔料は化粧料の着色等に使用され、一方、体質顔料は、化粧料の感触改良等に使用される。本発明における「粉体」としては、化粧料に通常使用される白色及び着色顔料、並びに、体質顔料を特に制限なく使用することができる。1種類又は2種類以上の粉体を配合することが好ましい。
本発明における「油剤」は、化粧料の成分として一般に使用されるものであり、特に限定されるものではない。油剤は、通常は室温で液体であるが、ワックスのような固形であってもよく、後述する高粘度かつ粘稠なガム状或いはペースト状であってもよい。
R6は、水素原子、水酸基、或いは、炭素原子数1〜30の、一価の非置換又はフッ素若しくはアミノ置換アルキル基、アリール基、アルコキシ基及び(CH3)3SiO{(CH3)2SiO}lSi(CH3)2CH2CH2-(lは0〜1000の整数)で示される基から選択される基であり、
dは、0〜3の整数であり、
eは、0〜1000の整数であり、
fは、0〜1000の整数であり、但し、1≦e+f≦2000である)
R6は、上記と同様であり、
gは、0〜8の整数であり、
hは、0〜8の整数であり、但し、3≦g+h≦8である)
R6は、上記と同様であり、
iは1〜4の整数であり、
jは0〜500の整数である)
で表されるオルガノポリシロキサンを使用することができる。
本発明の共変性オルガノポリシロキサンは、親水性の糖アルコール含有有機基と疎水性の長鎖炭化水素基を同一分子中に備えるので、界面活性剤として好適に用いることができる。本発明の界面活性剤中の前記共変性オルガノポリシロキサンの配合量は、界面活性効果を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
本発明の共変性オルガノポリシロキサンは、増粘剤又はゲル化剤、特に油剤の増粘剤又はゲル化剤として使用することもできる。本発明の増粘剤又はゲル化剤中の前記共変性オルガノポリシロキサンの配合量は、増粘効果又はゲル化効果を発揮する限り特に限定されるものではないが、例えば、50〜100重量(質量)%とすることができ、70〜100重量(質量)%が好ましく、90〜100重量(質量)%がより好ましい。
反応器に平均組成式:MD72DH 12Mで表されるメチルハイドロジェンポリシロキサン 172.6g、キシリトールモノアリルエーテル 19.4g、1−デセン 41.3g、イソプロピルアルコール(IPA) 75.2gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒30mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*1 3DR*2 9Mで表される「共変性シリコーン1」を得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C10H21
収量は196.0g(84%)であった。生成物の25℃における動粘度は650,000mm2/sec、屈折率は1.428、性状は淡褐色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD42DH 17Mで表されるメチルハイドロジェンポリシロキサン 126.3g、キシリトールモノアリルエーテル 14.1g、1−デセン 69.6g、イソプロピルアルコール(IPA) 63.0gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒24mgを添加し、80℃で2.5時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD42DR*1 2DR*2 15Mで表される「共変性シリコーン2」を得た。ここで、R*1及びR*2は下記を示す。
R*1= キシリトール残基
R*2= −C10H21
収量は180.6g(86%)であった。生成物の25℃における動粘度は135,200mm2/sec、屈折率は1.431、性状は淡黄色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD72DH 3Mで表されるメチルハイドロジェンポリシロキサン 168.9g、テトラグリセリンモノアリルエーテル 41.1g、IPA 63.0gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒24mgを添加し、80℃で3時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD72DR*4 3Mで表される「テトラグリセリン変性シリコーン」を得た。ここで、R*4は−C3H6O−X(Xはテトラグリセリン部分)を表す。収量は185.2g(88%)であった。生成物の25℃における動粘度は750,000mm2/sec以上、屈折率は1.429、性状は乳白色の不透明均一な粘稠液体であった。
反応器に平均組成式:MD70DH 3Mで表されるメチルハイドロジェンポリシロキサン 224.6g、キシリトールモノアリルエーテル 30.5g、イソプロピルアルコール(IPA) 75.0gを仕込み、窒素流通下で攪拌しながら80℃まで加温した。白金触媒30mgを添加し、80℃で3時間反応を行なった。IRスペクトルによりSi−H結合の消失を確認し、反応の進行を確認した後、反応液を減圧下で加熱して低沸分を溜去することによって、平均組成式:MD70DR*1 3Mで表される糖アルコール変性シリコーンを得た。ここで、R*1はキシリトール残基を表す。収量は215.0g(85%)であった。生成物の25℃における動粘度は83,000mm2/sec、屈折率は1.415、性状は淡黄色の不透明均一な粘稠液体であった。
実施例1で得られた「共変性シリコーン1」、及び、実施例2で得られた「共変性シリコーン2」を用いて表1に示す組成の油中水型乳化組成物を下記に示す方法によって調製し、以下の評価基準により、乳化安定性、乳化物外観の審美性、及び、官能性(感触・使用感)を評価した。また、乳化物を顕微鏡で観察(1000倍)することにより分散相の平均粒子径を求めた。より具体的には、顕微鏡観察において、視野内に確認された水相の粒子径の平均値を求めることにより、平均粒子径を決定した。結果を表1に併せて示す。なお、表中、数値は重量(質量)部を示す。
参考例1で得られた「テトラグリセリン変性シリコーン」、参考例2で得られた「糖アルコール変性シリコーン」、並びに、下記に示す「SS-2910」及び「FZ-2233」を用いて、表1及び表2に示す組成の油中水型乳化組成物を実施例3〜8の場合と同様に調製し、実施例3〜8の場合と同様に、乳化安定性、乳化物外観の審美性、及び、官能性(感触・使用感)を評価した。また、実施例3〜8の場合と同様に、乳化物中の分散相の平均粒子径を求めた。結果を表1及び表2に併せて示す。なお、表中、数値は重量(質量)部を示す。なお、明らかに乳化液が得られていない場合には、「×」とした。
(2)FZ−2233:直鎖状ブロック共重合体(ABn)タイプのポリエーテル変性シリコーン(商品名FZ−2233、東レ・ダウコーニング社製)
1. 容量150mlの容器に、表1及び表2に示される油剤、及び、界面活性剤(乳化剤)としての各変性シリコーンを仕込んだ。
2. 加温と撹拌を行い、各変性シリコーンを油剤中に均一分散又は溶解させた(油相A)。
3. 別の容器に食塩とイオン交換水とを仕込み、スパチュラで混合して溶解させた。更に、1,3−ブチレングリコールを混合して溶解させた(水相B)。
4. ホモディスパーの鋸歯を油相Aに浸し、容器を固定したのち1000rpmで攪拌しながら、水相Bをほぼ定速で約40秒かけて油相A中に注ぎ込んだ。
5. ホモディスパーの回転数を3000rpmに上げ、攪拌を更に1分間継続して油中水型乳化組成物を得た。
各組成の油中水型乳化組成物を40℃において1ヶ月間静置し、静置前後の乳化状態の変化を、以下の基準により評価した。
◎: 粘度変化≦±5% 且つ、外観は変化なく均一。
○: ±5%<粘度変化≦±10% 且つ、外観も均一。
△: ±10%<粘度変化≦±20%、又は乳化物の表面がやや不均一化。
×: ±20%<粘度変化、又は、水滴や水相の分離あり。
各組成の油中水型乳化組成物を室温で1日間静置した後の乳化物表面の美しさを、以下の基準により評価した。
◎: 乳化物表面に気泡や穴などによるツブがほとんど認められず、全体的になめらかで美しい外観である。
○: 表面に気泡や穴などによる微細なツブが少し認められるが、目立たない。なめらかで均質な外観。
△: 乳化物の表面粗さが容易に見え、気泡や穴などによるツブが連続的に存在している。
×: 乳化自体ができておらず相分離が起こり、表面が不均一化している。
各組成の油中水型乳化組成物0.10gを指にとって、前腕部に軽くすべらせるように塗布した。乳化物が均一に広がるよう、何度か皮膚(塗布部位)を指で軽くなぞる動作を繰り返し、このときの感触及び使用感を、以下の基準により評価した。
○: しっとりした感触で滑らかに良く伸び、さらっとしてべとつきも無い。
△: しっとりした感触でべとつきも無いが、やや滑らかさが不足している。
×: 重く伸びが悪い、又はべとつきが気になる、又は油っぽい感触である。
実施例1で得られた「共変性シリコーン1」及び実施例2で得られた「共変性シリコーン2」を用いて表3に示す組成のリキッドファンデーションを調製し、以下の評価手順及び評価基準により、伸び広がり性、仕上がりの美しさ、密着感、違和感のない自然な肌感覚、及び、安定性を評価した。結果を表3に併せて示す。なお、表中、数値は重量(質量)部を示す。
参考例1で得られた「テトラグリセリン変性シリコーン」、参考例2で得られた「糖アルコール変性シリコーン」、及び、「SS-2910」を用いて、表3に示す組成のリキッドファンデーションを調製し、実施例9及び10と同様に、伸び広がり性、仕上がりの美しさ、密着感、違和感のない自然な肌感覚、安定性を評価した。結果を表3に併せて示す。なお、表中、数値は重量部を示す。
1. 得られたリキッドファンデーション0.15gを、予め産毛を剃り落とした清浄な皮膚上(前腕部)に、パフを用いて直径約5cmの円形に均一に塗布し、肌への「伸び広がり性」を評価した。
2. 塗布10分後(初期)、4時間後、及び、9時間後の時点で、「仕上がりの美しさ」、「密着感」、及び、「違和感のない自然な肌感覚」について、目視及び触感にて官能評価を行った。
3. 得られたリキッドファンデーションを40℃で2ヶ月静置させた後、外観及び性状の安定性を評価した。
各項目について、以下の基準により評価した。
◎: 滑らかによく伸び広がった。
○: 普通に伸び広がった。
△: 伸び広げるのに通常よりも力を要した。
◎: 緊密にカバーされ、非常に美しい仕上がりであった。
○: 緊密にカバーされてはいるが、小皺による溝が僅かにあった。
×: 塗布表面の均一感がやや不足し、きめの粗さが目立ってきた。
◎: 密着感をはっきりと感じた。
○: 密着感はあるが、意識しないと気づかないレベルだった。
×: 密着感を全く感じなかった。
◎: 違和感の無い自然な皮膚感覚であった。
○: 皮膚感覚に僅かの違和感があった。
△: 少し不自然な皮膚感覚があった。
○: 分離や粉の沈降が無く、均一な外観・性状を維持していた。
△: 粉の沈降が若干認められたが、振り混ぜると容易に均一に再分散できた。
×: 粉が沈降し、振り混ぜても均一な再分散ができなかった。
A: 成分1)及び成分6)〜13)を室温で混合した後、ホモミキサーで撹拌しながら溶解させる。
B: 成分14)〜16)を混合し、完全に溶解させる。
C:その後、Aをホモミキサーで撹拌しながらBを添加する。
D:これに成分2〜5を加え、ホモミキサーで混合分散後、脱気し、容器へ充填して液状ファンデーションを得た。
本実施例にかかる日焼け止め化粧料の調製に先立ち、実施例2で得られた「共変性シリコーン2」を用いて、化粧料原料である酸化亜鉛分散体を調製した。具体的には、微粒子酸化亜鉛(商品名:微粒子酸化亜鉛(テイカ製、MZY-505S)) 30g、実施例2で得られた「共変性シリコーン2」 2.5g、及び、デカメチルシクロペンタシロキサン 17.5gを混合し、ジルコニアビーズ(0.8 mm Φ) 200gを加え、ペイントシェイカーにて1時間混合してスラリー状の分散体を作成した。
1. ポリエーテル変性シリコーン(注1) 3部
2. アルキルシリコーンWAX(注2) 2部
3. 流動パラフィン 5部
4. イソノナン酸イソデシル 6部
5. 酸化チタン分散体(注3) 2部
6. 酸化亜鉛分散体(注4) 10部
7. グリセリン 4部
8. 塩化ナトリウム 1部
9. 精製水 残量
10. 防腐剤 適量
注1)ダウコーニング社製、DC5200を使用した。
注2)ダウコーニング社製、AMS-C30 COSMETIC WAXを使用した。
注3)「酸化チタン分散体」は下記の方法に従って製造したものを使用した。
微粒子酸化チタン(商品名:MTY−100SAS(テイカ社製))20g、実施例2で得られた「共変性シリコーン2」5g及びイソドデカン25gを混合し、ジルコニアビーズ(0.8 mm Φ)200gを加え、ペイントシェイカーにて1時間混合してスラリー状の分散体を作成した。
注4)上記の方法に従って、調製したサンプルを使用した。
成分1〜6を混合撹拌して得られた油相に成分7〜10を混合撹拌して得られた水相を添加し、撹拌して乳化した。
(成分)
1. ポリシリコーン13(注1) 3部
2. デカメチルペンタシクロシロキサン 14部
3. 共変性シリコーン1 0.5部
4. オクタン酸セチル 3部
5. カルビノール変性シリコーン 2部
6. 流動パラフィン 5部
7. PPG−3 ミリスチルエーテル 5部
8. 1,3−ブチレングリコール 4部
9. 塩化ナトリウム 1部
10. 精製水 残量
11. ステアリン酸処理酸化チタン 6.68部
12. ステアリン酸処理酸化鉄(赤、黄色、黒) 1.62部
13. ステアリン酸処理マイカ 1.7部
注1)直鎖状ブロック共重合体(ABn)タイプのポリエーテル変性シリコーン:東レ・ダウコーニング社製FZ−2233を使用した。
成分1〜7を混合して均一に溶解させた。成分1〜7の混合物に成分11〜13を加えて分散させ、更に成分8〜10の混合物を加えて乳化し、リキッドファンデーションを作成した。
(成分)
1. 軽質流動イソパラフィン 45部
2. カプリルメチコン 5部
3. 重質流動パラフィン 7.2部
4. ジメチルシリコーン(6cs) 1部
5. 共変性シリコーン1 1部
6. 有機変性粘度鉱物 3.5部
7. ポリエチレンワックス 4部
8. キャンデリラワックス 5部
9. マイクロクリスタリンワックス 2.5部
10. パルミチン酸デキストリン 5部
11. エタノール 2部
12. タルク 10部
13. ステアリン酸処理酸化チタン 8部
14. 赤色201号 適量
15. 防腐剤 適量
16. 酸化防止剤 0.3部
成分1〜16を混合し、油性マスカラを得た。
(成分)
1. 重質流動イソパラフィン 50部
2. 流動パラフィン 16.2部
3. リンゴ酸ジイソステアリル 10部
4. 2−エチルヘキサン酸セチル 10部
5. パルミチン酸デキストリン 7部
6. トリメチルシロキシケイ酸 2部
7. オクチルシラン処理酸化チタン 2部
8. 共変性シリコーン2 2部
9. 赤色201号 0.2部
10. パラヒドロキシ安息香酸メチル 0.3部
11. トコフェロール 0.3部
成分1〜11を混合し、型に流し込みリップグロスを得た。
Claims (19)
- 下記一般式(1):
{式中、
R1は炭素原子数1〜8の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは下記一般式(2−1):
(式中、
R3は二価有機基を表し、
dは1又は2である)、又は、下記一般式(2−2):
(式中、
R3は上記のとおりであり、
d’は0又は1である)で表わされる糖アルコール基含有有機基であり、
a 、b 及びcは、それぞれ、1.0≦a≦2.5、0.0001≦b≦1.5、及び、0.0001≦c≦1.5の範囲にある数である}で表される共変性オルガノポリシロキサン。 - 上記一般式(2−1)又は(2−2)において、R3である二価有機基が炭素原子数3〜5の、置換若しくは非置換の、直鎖状若しくは分岐状の二価炭化水素基である、請求項1記載の共変性オルガノポリシロキサン。
- 前記共変性オルガノポリシロキサンが、下記一般式(3):
{式中、R1は炭素原子数1〜8の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
R2は炭素原子数9〜30の、置換若しくは非置換の、直鎖状若しくは分岐状の一価炭化水素基を表し、
Qは上記一般式(2−1)又は(2−2)で表される糖アルコール含有有機基であり、
Xは上記のR1、R2及びQで表される官能基のいずれかを表し、
a=0〜2000、b=0〜200、c=0〜50であり、b=0の場合、Xの少なくとも一つはR2で表される基である。また、c=0の場合、Xの少なくとも一つはQで表される基である。}で表される、請求項1又は2記載の共変性オルガノポリシロキサン。 - 上記一般式(3)において、
R1がメチル基であり、
R2が炭素原子数10〜20の、置換若しくは非置換の、直鎖状若しくは分岐状のアルキル基であり、
更に、a+b+cが0〜1000の範囲であることを満たし、且つ
a=0〜1000、b=0〜150、c=0〜50の範囲の数(ただし、b=0の場合、Xの少なくとも一つはR2で表される基であり、c=0の場合、Xの少なくとも一つはQで表される基である。)であることを特徴とする請求項3記載の共変性オルガノポリシロキサン。 - 請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサンを含む界面活性剤。
- (A)請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサン、(B)水、及び、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含むエマルジョン組成物。
- 請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサンを含む粉体処理剤。
- 粉体表面処理剤である、請求項7記載の粉体処理剤。
- 請求項8記載の粉体処理剤で表面処理された粉体。
- (A)請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサン、及び、(D)粉体を含む化粧料用原料。
- 更に、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含む請求項10記載の化粧料用原料。
- 請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサンを含むゲル化剤。
- (A)請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサン、及び、(C)シリコーン油、非極性有機化合物及び低極性有機化合物からなる群から選択される5〜100℃で液状の少なくとも1種の油剤を含むゲル状組成物。
- 請求項1乃至4のいずれかに記載の共変性オルガノポリシロキサンを含む外用剤。
- 請求項6記載のエマルジョン組成物を含む外用剤。
- 請求項9記載の粉体を含む化粧料。
- 請求項10又は11記載の化粧料用原料を含む化粧料。
- 請求項13記載のゲル状組成物を含む外用剤。
- 化粧料である、請求項14、15又は18記載の外用剤。
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| Country | Link |
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| US (1) | US9980897B2 (ja) |
| EP (1) | EP2563845B1 (ja) |
| JP (1) | JP5841347B2 (ja) |
| KR (1) | KR20130058700A (ja) |
| CN (1) | CN102906161B (ja) |
| WO (1) | WO2011136397A1 (ja) |
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| EP2563844A1 (en) | 2010-04-30 | 2013-03-06 | Dow Corning Toray Co., Ltd. | Organopolysiloxane and use thereof as surfactant, powder treatment agent, thickening agent of oil -based raw material or gelling agent. gel and emulsion compositions, as well as, preparations for external use and cosmetics comprising the same |
| CN103154093B (zh) | 2010-08-23 | 2015-08-26 | 道康宁公司 | 糖硅氧烷共聚物及其制备和使用方法 |
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| WO2012165235A1 (ja) * | 2011-05-30 | 2012-12-06 | 東レ・ダウコーニング株式会社 | 新規オルガノポリシロキサンエラストマー及びその利用 |
| JP5756344B2 (ja) * | 2011-05-30 | 2015-07-29 | 東レ・ダウコーニング株式会社 | 新規液状オルガノポリシロキサン及びその利用 |
| JP6105920B2 (ja) * | 2011-12-27 | 2017-03-29 | 東レ・ダウコーニング株式会社 | 共変性オルガノポリシロキサン、それを含有してなる油中水型エマルション用乳化剤、外用剤および化粧料 |
| JP6313540B2 (ja) | 2011-12-27 | 2018-04-18 | 東レ・ダウコーニング株式会社 | ジグリセリン誘導体変性シリコーン、それを含有してなる油中水型エマルション用乳化剤、外用剤および化粧料 |
| JP6369888B2 (ja) | 2011-12-27 | 2018-08-08 | 東レ・ダウコーニング株式会社 | 新規液状オルガノポリシロキサン及びその利用 |
| JP6092545B2 (ja) | 2012-08-22 | 2017-03-08 | 東レ・ダウコーニング株式会社 | カルボシロキサンデンドリマー構造および親水性基を有する共重合体およびその用途 |
| JP5797618B2 (ja) | 2012-08-22 | 2015-10-21 | 東レ・ダウコーニング株式会社 | 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、それを含む組成物及び化粧料 |
| JP6022289B2 (ja) | 2012-10-02 | 2016-11-09 | 東レ・ダウコーニング株式会社 | 共変性オルガノポリシロキサンを含有してなる処理剤および化粧料 |
| JP6063197B2 (ja) | 2012-10-02 | 2017-01-18 | 東レ・ダウコーニング株式会社 | 新規な共変性オルガノポリシロキサン、それを含有してなる粉体処理剤および粉体組成物 |
| EP3009466B1 (en) * | 2013-06-13 | 2021-02-24 | Dow Toray Co., Ltd. | Silicone modified by long-chain hydrocarbon group-containing diglycerin derivative, and use thereof |
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| WO2015162904A1 (ja) | 2014-04-21 | 2015-10-29 | 東レ・ダウコーニング株式会社 | 液状の高純度糖誘導体変性シリコーン又はその組成物の製造方法 |
| CN106414557A (zh) | 2014-04-21 | 2017-02-15 | 道康宁东丽株式会社 | 液态高纯度多元醇衍生物改性的有机硅或其组合物的制造方法 |
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| KR20250116678A (ko) | 2022-11-30 | 2025-08-01 | 다우 도레이 캄파니 리미티드 | 유기규소-작용성 공중합체의 고체 입자, 이의 제조 방법, 및 상기 고체 입자를 포함하는 화장료 |
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- 2011-04-28 US US13/643,676 patent/US9980897B2/en not_active Expired - Fee Related
- 2011-04-28 EP EP11727805.1A patent/EP2563845B1/en not_active Not-in-force
- 2011-04-28 KR KR1020127030758A patent/KR20130058700A/ko not_active Withdrawn
- 2011-04-28 WO PCT/JP2011/060803 patent/WO2011136397A1/en not_active Ceased
- 2011-04-28 JP JP2011102362A patent/JP5841347B2/ja not_active Expired - Fee Related
- 2011-04-28 CN CN201180025854.XA patent/CN102906161B/zh not_active Expired - Fee Related
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|---|---|
| WO2011136397A1 (en) | 2011-11-03 |
| EP2563845B1 (en) | 2015-01-07 |
| US9980897B2 (en) | 2018-05-29 |
| US20130102686A1 (en) | 2013-04-25 |
| JP2011246705A (ja) | 2011-12-08 |
| CN102906161B (zh) | 2014-10-22 |
| KR20130058700A (ko) | 2013-06-04 |
| CN102906161A (zh) | 2013-01-30 |
| EP2563845A1 (en) | 2013-03-06 |
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