JP6196038B2 - 膨潤シリコーンゲルを含むシリコーン組成物 - Google Patents
膨潤シリコーンゲルを含むシリコーン組成物 Download PDFInfo
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- JP6196038B2 JP6196038B2 JP2012535287A JP2012535287A JP6196038B2 JP 6196038 B2 JP6196038 B2 JP 6196038B2 JP 2012535287 A JP2012535287 A JP 2012535287A JP 2012535287 A JP2012535287 A JP 2012535287A JP 6196038 B2 JP6196038 B2 JP 6196038B2
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- 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
- 229960002703 undecylenic acid Drugs 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 235000012141 vanillin Nutrition 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229960003048 vinblastine Drugs 0.000 description 1
- JXLYSJRDGCGARV-XQKSVPLYSA-N vincaleukoblastine Chemical compound C([C@@H](C[C@]1(C(=O)OC)C=2C(=CC3=C([C@]45[C@H]([C@@]([C@H](OC(C)=O)[C@]6(CC)C=CCN([C@H]56)CC4)(O)C(=O)OC)N3C)C=2)OC)C[C@@](C2)(O)CC)N2CCC2=C1NC1=CC=CC=C21 JXLYSJRDGCGARV-XQKSVPLYSA-N 0.000 description 1
- OGWKCGZFUXNPDA-XQKSVPLYSA-N vincristine Chemical compound C([N@]1C[C@@H](C[C@]2(C(=O)OC)C=3C(=CC4=C([C@]56[C@H]([C@@]([C@H](OC(C)=O)[C@]7(CC)C=CCN([C@H]67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)C[C@@](C1)(O)CC)CC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-XQKSVPLYSA-N 0.000 description 1
- 229960004528 vincristine Drugs 0.000 description 1
- OGWKCGZFUXNPDA-UHFFFAOYSA-N vincristine Natural products C1C(CC)(O)CC(CC2(C(=O)OC)C=3C(=CC4=C(C56C(C(C(OC(C)=O)C7(CC)C=CCN(C67)CC5)(O)C(=O)OC)N4C=O)C=3)OC)CN1CCC1=C2NC2=CC=CC=C12 OGWKCGZFUXNPDA-UHFFFAOYSA-N 0.000 description 1
- 238000011179 visual inspection Methods 0.000 description 1
- 235000019155 vitamin A Nutrition 0.000 description 1
- 239000011719 vitamin A Substances 0.000 description 1
- 235000010374 vitamin B1 Nutrition 0.000 description 1
- 239000011691 vitamin B1 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
- 229940045997 vitamin a Drugs 0.000 description 1
- 229940011671 vitamin b6 Drugs 0.000 description 1
- 239000000341 volatile oil Substances 0.000 description 1
- 235000020234 walnut Nutrition 0.000 description 1
- 239000008170 walnut oil Substances 0.000 description 1
- 239000010698 whale oil Substances 0.000 description 1
- 239000010497 wheat germ oil Substances 0.000 description 1
- 230000037303 wrinkles Effects 0.000 description 1
- 229940075420 xanthine Drugs 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
- 239000012138 yeast extract Substances 0.000 description 1
- 239000009538 yokuinin Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- GAWWVVGZMLGEIW-GNNYBVKZSA-L zinc ricinoleate Chemical compound [Zn+2].CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O.CCCCCC[C@@H](O)C\C=C/CCCCCCCC([O-])=O GAWWVVGZMLGEIW-GNNYBVKZSA-L 0.000 description 1
- 229940100530 zinc ricinoleate Drugs 0.000 description 1
- OJYLAHXKWMRDGS-UHFFFAOYSA-N zingerone Chemical compound COC1=CC(CCC(C)=O)=CC=C1O OJYLAHXKWMRDGS-UHFFFAOYSA-N 0.000 description 1
- 239000001243 zingiber officinale rosc. root absolute Substances 0.000 description 1
Images
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- 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
- C08G77/42—Block-or graft-polymers containing polysiloxane sequences
- C08G77/442—Block-or graft-polymers containing polysiloxane sequences containing vinyl polymer sequences
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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
- A61K8/02—Cosmetics or similar toiletry preparations characterised by special physical form
- A61K8/04—Dispersions; Emulsions
- A61K8/042—Gels
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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
- A61K8/81—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions involving only carbon-to-carbon unsaturated bonds
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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
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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
- A61K8/891—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone
- A61K8/893—Polysiloxanes saturated, e.g. dimethicone, phenyl trimethicone, C24-C28 methicone or stearyl dimethicone modified by an alkoxy or aryloxy group, e.g. behenoxy dimethicone or stearoxy dimethicone
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- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
- A61Q15/00—Anti-perspirants or body deodorants
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J3/00—Processes of treating or compounding macromolecular substances
- C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
- C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
- C08J3/075—Macromolecular gels
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- 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
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
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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
- A61K2800/54—Polymers characterized by specific structures/properties
- A61K2800/546—Swellable particulate polymers
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- Cosmetics (AREA)
- Macromonomer-Based Addition Polymer (AREA)
Description
一般的には、成分(A)は、フリーラジカル重合性基を有するオルガノポリシロキサンを含む。該オルガノポリシロキサンは、ポリマー又はオリゴマー及びポリマーの混合物とすることができ、ポリマーオルガノポリシロキサンはホモポリマー又はヘテロポリマーのいずれかとすることができる。なお、オルガノポリシロキサンは線状、分岐、又は超分岐構造とすることができる。成分(A)にフリーラジカル触媒付加重合を行い、いくつかの態様では、共重合及び/又は架橋を行うこともできる。
(1)R1 3SiO(R1 2SiO)a(R1R2SiO)bSiR1 3
において、aは0〜20,000の値を有し、bは1〜20,000の値を有し、各R1基は独立して水素、ハロゲン、又は一価有機基であり、各R2基は独立して一価不飽和有機基である、式;及び
(2)R3 2R4SiO(R3 2SiO)c(R3R4SiO)dSiR3 2R4
において、cは0〜20,000の値を有し、dは0〜20,000の値を有し、各R3は独立して水素、ハロゲン、又は一価有機基であり、各R4基は独立して一価不飽和有機基である、式
から選択される式を有するフリーラジカル重合性オルガノポリシロキサンを含むことができる。
から選択されるオルガノポリシロキサンの構造単位を有するシロキサン樹脂を含むことができ、
Mは単官能性単位R3SiO1/2を表し、Dは二官能性単位R2SiO2/2を表し、Tは三官能性単位RSiO3/2を表し、Qは四官能性単位SiO4/2を表す。
一般的には、成分(B)はフリーラジカルを生成し、フリーラジカル付加重合及び/又は架橋を開始させることができる少なくとも1つの有機ボラン化合物を含む。有機ボランを周囲条件で非自然発火性にする安定化有機ボラン化合物を用いることができる。いくつかの態様では、成分(B)は、酸素の存在下で有機窒素反応性化合物を導入するとフリーラジカルを生成(し、重合を開始)する、有機ボランと、錯体を周囲条件で安定にする適切な有機窒素(例えば、アミン)との間で形成された錯体である。いくつかの態様では、成分(B)は加熱するとフリーラジカルを生成(し、重合を開始)する有機ボラン化合物である。いくつかの態様では、成分(B)は、溶媒を蒸発させ、ボランを遊離し、これによりラジカルを生成する、溶媒安定化有機ボラン(例えば、トリアルキルボランのTHF溶液)である。
式中、Bはホウ素を表し、Nは窒素を表し;R6、R7、及びR8の少なくとも1つは、ケイ素含有基がホウ素に共有結合した1つ以上のケイ素原子を含有し;R6、R7、及びR8は、独立して水素、シクロアルキル基、骨格上に1〜12個の炭素原子を有する線状若しくは分岐アルキル基、アルキルアリール基、アルキルシラン若しくはアリールシラン基のようなオルガノシラン基、オルガノシロキサン基、別のホウ素原子との共有結合として機能することができるアルキレン基、別のホウ素原子との共有結合として機能することができる二価オルガノシロキサン基、又はこれらのハロゲン置換ホモログから選択することができる基であり;R9、R10、及びR11は、ホウ素と錯化することができるアミン化合物又はポリアミン化合物を生成する基であり、独立して水素、1〜10個の炭素原子を含有するアルキル基、1〜10個の炭素原子を含有するハロゲン置換アルキル基、又は有機ケイ素官能性基から選択され;R6、R7、及びR8基の少なくとも2つ並びにR9、R10、及びR11基の少なくとも2つを組み合わせ、複素環構造を形成することができるが、ただし、2つの結合基からの原子数の合計は11を超えない。
一般的には、成分(C)は、貧溶媒又は非溶媒のような非混和性流体とは対照的に、シリコーンエラストマーとそれを膨潤させるのに十分に相溶性である、少なくとも1つの混和性流体を含む。いくつかの態様では、適切な混和性流体は、シリコーン;有機化合物;イオン性液体及び超臨界流体のような「環境に優しい」溶媒;並びにこれらの混合物から選択することができる。
一般的には、任意の成分(D)は、成分(B)の有機ボラン−有機窒素錯体と組み合わされ、酸素化環境に露出されると、有機ボラン−有機窒素錯体を解離させ、これによりフリーラジカル重合及び/又は架橋を開始させることができる、少なくとも1つの有機窒素反応性化合物を含む。こうした有機窒素反応性化合物の存在は、室温以下を含む成分(B)の有機ボラン−有機窒素錯体の解離温度より低い温度での急速な重合及び/又は架橋を可能にする。
一般的には、成分(E)は、フリーラジカル重合することができる少なくとも1つの有機コモノマーを含む。いくつかの態様では、成分(E)は、分子当たり少なくとも1つのフリーラジカル重合性基を有する有機コモノマーである。いくつかの実施形態では、成分(E)の有機コモノマーは分子当たり少なくとも1つの親水性基を有する。適切な有機化合物の例としては、これらに限定されないが、2−エチルヘキシルアクリレート、2−エチルヘキシルメタクリレート、メチルアクリレート、メチルメタクリレート、ネオペンチルグリコールジアクリレート、ネオペンチルグリコールジメタクリレート、グリシジルアクリレート、グリシジルメタクリレート、アリルアクリレート、アリルメタクリレート、ステアリルアクリレート、テトラヒドロフリルメタクリレート、カプロラクトンアクリレート、ペルフルオロブチルアクリレート、ペルフルオロブチルメタクリレート、1H,1H,2H,2H−ヘプタデカフルオロデシルアクリレート、1H,1H,2H,2H−ヘプタデカフルオロデシルメタクリレート、テトラヒドロペルフルオロアクリレート、フェノキシエチルアクリレート、フェノキシエチルメタクリレート、ビスフェノールAアクリレート、ビスフェノールAジメタクリレート、エトキシル化ビスフェノールAアクリレート、エトキシル化ビスフェノールAメタクリレート、ヘキサフルオロビスフェノールAジアクリレート、ヘキサフルオロビスフェノールAジメタクリレート、ジエチレングリコールジアクリレート、ジエチレングリコールジメタクリレート、ジプロピレングリコールジアクリレート、ジプロピレングリコールジメタクリレート、ポリエチレングリコールジアクリレート、ポリエチレングリコールジメタクリレート、ポリプロピレングリコールメタクリレート、ポリプロピレングリコールジアクリレート、ポリプロピレングリコールジメタクリレート、プロピレングリコールモノメタクリレート、エチレングリコールモノメタクリレート、N−イソプロピルアクリルアミド、トリメチロールプロパントリアクリレート、トリメチロールプロパントリメタクリレート、エトキシル化トリメチロールプロパントリアクリレート、エトキシル化トリメチロールプロパントリメタクリレート、ペンタエリスリトールトリアクリレート、ペンタエリスリトールトリメタクリレート、ペンタエリスリトールテトラアクリレート、ペンタエリスリトールテトラメタクリトール、メチル−3−ブテノエート、アリルメチルカーボネート、ジアリルピロカーボネート、アリルアセトアセテート、ジアリルカーボネート、ジアリルフタレート、ジメチルイタコネート、ジアリルカーボネート、又はこれらの組み合わせが挙げられる。他の有用な有機化合物としては、ヒドロキシアクリレートのようなイソシアネート反応性アクリレートモノマー、オリゴマー又はポリマーをイソシアネート官能性プレポリマーと反応させることにより調製された(メタ)アクリレート末端ポリウレタンプレポリマー;アクリレート又はメタクリレート末端ポリイソブチレンのような(メタ)アクリレート末端ゴム状オリゴマー及びポリマー;並びにメタクリレート官能基化大豆油のような(メタ)アクリレート官能基化天然油誘導体が挙げられる。当業者であれば、成分(E)についての有機化合物の選択が、とりわけ、成分(A)の性質及び得られる製品の所望の用途によって決まるだろうということを認識するだろう。良好な結果は、成分(E)としてのメタクリレート(例えば、ポリプロピレングリコールモノメタクリレート)の選択によって得られた。いくつかの態様では、成分(E)はアクリレート及びメタクリレートから選択される。
一般的には、任意の成分(F)は、エラストマー粒子によるin situカプセル化のためシリコーン組成物に添加することができる、少なくとも1つのパーソナルケア又はヘルスケア活性成分を含む。いくつかの態様では、成分(F)はシリコーン組成物に、シリコーンエラストマーの生成中に添加してもよく(プリロード法)、又はシリコーンエラストマーの形成後に添加してもよい(ポストロード法)。いくつかの態様では、感熱活性成分は熱応答又は分解についてのそれらの閾値温度より低い温度で組成物中に組み込まれる。いくつかの態様では、組成物中に懸濁させた活性成分は、そうである必要はないが、粒子形態であり得る。活性成分がカプセル化の条件で粒子形態である場合、その粒径、分布、又は形状は限定されない。組成物中の他の成分の厳選により、ポリマー粒子の特性を制御し、活性成分の放出の望ましいメカニズムを可能にすることができる。放出メカニズムの例としては、熱、機械的、及び化学的応力による抽出、溶出、膨潤、溶融、軟化、分解、研磨、圧搾又は粗砕が挙げられる。
シリコーン組成物は追加成分を含むこともできる。限定することなく、こうした任意の追加成分の例としては、界面活性剤;乳化剤;分散剤;ポリマー安定剤;架橋剤;粒子のニ次重合又は架橋をもたらすのに有用なポリマー、架橋剤、及び触媒の組み合わせ;増粘剤のようなレオロジー調整剤;密度調整剤;アジリジン安定剤;ヒドロキノン及びヒンダードアミンのような硬化調整剤;有機過酸化物及びオゾニドのようなフリーラジカル開始剤;ポリマー;希釈剤;酸受容体;抗酸化剤;熱安定剤;難燃剤;捕捉剤;シリル化剤;気泡安定剤;溶媒;希釈剤;可塑剤;充填剤及び無機粒子、顔料、染料並びに乾燥剤が挙げられる。
各種実施形態では、シリコーンエラストマー組成物の調製方法が提供される。こうした方法は、成分(A)を成分(B)、成分(C)、酸素、任意で成分(D)、任意で成分(E)、及び任意で成分(F)の存在下、約5℃〜約95℃の温度を維持しながら重合させ、実質的に均質なシリコーンエラストマーゲルを形成する工程を含む。いくつかの実施形態では、ゲルは、成分(C)と相溶性であり、これを吸収するエラストマーを有する。いくつかの実施形態では、形成されたゲルは、不希釈状態のシリコーンエラストマーの固有のプラトーせん断弾性率の1/2以下のプラトーせん断弾性率を有する。
本発明の実施形態によると、オルガノポリシロキサンネットワークを含むシリコーン組成物、及びこうした組成物の製造方法が提供される。いくつかの実施形態では、組成物はゲル、ペースト、又はパウダーである。いくつかの実施形態では、シリコーンゲル組成物は、オルガノポリシロキサンを、有機ボランフリーラジカル触媒により開始されるフリーラジカル重合によって、少なくとも1つの混和性流体の存在下で重合させ、混和性流体を吸収するシリコーンエラストマーマトリックスを形成する工程を含む方法により調製される。よって、エラストマーは混和性流体中で膨潤性又はそれ以外では相溶性であり、混和性流体はエラストマーにより吸収され、エラストマーは膨潤するので、本発明のシリコーンゲル組成物は均質(すなわち単相)である。いくつかの実施形態では、組成物は約20〜約99(重量)%の1つ以上の混和性流体、及び約5〜約80(重量)%のエラストマーを含む。いくつかの実施形態では、組成物は約50〜約90(重量)%の1つ以上の混和性流体、及び約10〜約50(重量)%のエラストマーを含む。混和性流体は、得られるエラストマーマトリックスにより増粘され、膨潤状態で、不希釈状態のエラストマーの固有のプラトーせん断弾性率の半分以下である、プラトーせん断弾性率(G)を有するゲル又は半固体状態を形成する。
シリコーン組成物はさまざまな用途に有用である。例えば、それらは、燃料若しくは油のような非極性流体の修復若しくは安全な輸送に;電気ケーブルの充填材又は絶縁材として;地盤安定化のための土又は水バリアとして;又は電子産業においてコイルオンプラグ設計に用いられるエポキシ材料の代替品として用いることができる。こうした組成物は、架橋シリコーンゴム粒子の担体として用いることもでき、粒子の封止材、塗料、被覆剤、潤滑油、接着剤、消泡剤、及びポッティング用途への組み込みを容易にする。さらに、シリコーンゲル組成物は、医薬剤、殺生物剤、殺虫剤、除草剤、及び他の生物活性物質の担体として、並びに水及び水溶性物質、例えばサリチル酸、グリセロール、酵素、及びグリコール酸を疎水系に組み込むために用いることもできる。
膨潤エラストマーの製造方法
以下の手順を(表1に挙げる材料で置き換えて)行い、膨潤エラストマーを有するシリコーンゲルを作成した。すべての工程を周囲実験室温度で完了した。
1.以下の成分:3.53gの、成分(A)、MA−PDMS(8,000g/molの数平均分子量を有するメタクリロキシプロピルジメチルシロキシ末端ポリジメチルシロキサン)中の成分(B)、TNBB−MOPA(トリ−n−ブチルボランと1.3モル当量の3−メトキシプロピルアミンとの錯体)の4.3重量%溶液、及び16.52gの成分(C)、デカメチルシクロペンタシロキサン(D5)を20秒間Max 20 SpeedMixerカップ中で混合し、混合物Aを形成した。
2.以下の材料:3.51gの成分(A)、MA−PDMS中の成分(D)の4.3重量%溶液、及び16.61gの成分(C)、デカメチルシクロペンタシロキサンを20秒間第2のMax 20 SpeedMixerカップ中で混合し、混合物Bを形成した。
3.磁気撹拌棒を含有する8オンスガラス瓶中、19.41gの混合物Bを19.19gの混合物Aに添加し、窒素パージ雰囲気中、磁気撹拌棒で継続的に撹拌した。
4.材料を撹拌棒で混合し続けられないほど粘性になる(硬化する)まで混合し続け、膨潤エラストマーを形成した。この硬化は約30分後に起こった。
5.必要に応じて、追加のD5(又は代替の混和性流体)を添加し、所望の最終エラストマー含有量(FEC)を達成した。
ON−RC=有機窒素反応性化合物
IPDI=イソホロンジイソシアネート
D5=デカメチルシクロペンタシロキサン
IDD=イソドデカン
APTES=3−アミノプロピルトリエトキシシラン
膨潤非球状エラストマー粒子のエラストマーペーストの製造方法
以下の手順を、記載する材料及び量で適当に置き換えて行い、実施例1に記載した膨潤非球状エラストマー粒子のエラストマーペーストを作成した。
1.12.97gの組成物E(実施例1)の膨潤エラストマーをMax 20 SpeedMixerカップに入れた。
2.約1〜2グラムのドライアイスを、ドライアイスのいずれかの蒸発からの圧力を緩和するため蓋に小さな穴を開けたMax 20 Speedmixerカップに添加した。容器を間にへら混合サイクルを有する2回の30秒サイクルで混合した。
3.ブレンドの目視検査が粒径の減少を示すまで工程2を繰り返した。
4.粒径減少後、試料を追加のD5で所望の最終エラストマー含有量(FEC)までさらに希釈した。5.40gのD5を添加間に混合しながら少しずつ添加した。これは12.4%の最終エラストマー含有量をもたらした。
5.得られたエラストマーペーストは、10rad/s及び5%歪みで測定された48.5Pa・sのη’値を有した。
弾性率のレオロジー試験
試料の弾性率測定値は、Rheometrics Dynamic Analyzer RDA IIレオメーター上で平行平板形状を用いる周波数掃引モードで得た。報告する弾性率は5%歪み及び10rad/sの周波数での動的保存弾性率(G’)である。この値は、エラストマー材料に関連するもっとも代表的なプラトー圧G’として選択した。試料厚さは一般的には1〜3mmの範囲内とした。分析中に集めたデータをTA Orchestrator Version V7.1.2.3を用いて処理した。すべての試験は室温で行った。
制汗剤
以下の成分:(i)3.79gの組成物Sのエラストマーペースト;(ii)0.30gの安息香酸C12〜15アルキル(Finsolv TN);(iii)2.506gのアルミニウム−ジルコニウムテトラクロロヒドレン−Gly、USP(Summit AAZG−7167);(iv)0.10gのシリコーンエラストマーパウダー(9506パウダー);並びに(v)3.36gのジメチコーン及びトリシロキサンの混合物(2−1184)を空のMax 20 Hauschildカップに添加した。成分をHauschildミキサー中、最大速度で30秒間混合した。へらを用い、試料材料をカップ中でじっくり混合し、側面及び底面の材料が均一に組み込まれるようにした。材料を再度Hauschildミキサー中、最大速度で30秒間混合した。得られた材料を均一な外観について目視検査した。
フェイシャルモイスチャライザー
フェイシャルモイスチャライザーを以下のように調製した。混合物Aは:(i)1.01gのエラストマーペースト(D5中に7%FECまで希釈した組成物S);(ii)0.52gのオクチルメトキシシンナメート;及び(iii)0.33gのポリアクリルアミド(及び)C13〜C14イソパラフィン(及び)ラウレス−7(Sepigel 305)をHauschildミキサー中で30秒間組み合わせることにより形成した。混合物Bは:(i)0.40gのグリセロール;(ii)0.04gのDMDMヒダントイン;及び(iii)7.84gのDI水をHauschildミキサー中で30秒間組み合わせることにより形成した。混合物A及び混合物BをHauschildミキサー中、30秒間組み合わせ、混合した。
親水性変性シリコーンエラストマーを含むゲル化溶媒
以下の手順を行い、膨潤エラストマーを作成した。すべての工程を周囲実験室温度下で完了させた。
1.混合物Aは、Max 10 Speedmixerカップ中、1.21gのMA−PDMS中のTNBB−MOPAの4重量%溶液及び4.805gのD5を20秒間混合することにより調製した。
2.混合物Bは、第2のMax 10 Speedmixerカップ中、1.21gのMA−PDMS中の4重量%IPDI及び10重量%ポリプロピレングリコールモノメタクリレート溶液並びに4.80gのD5を20秒間混合することにより調製した。
3.磁気撹拌棒を含有する8オンスガラス瓶中、5.61gの混合物Bを5.69gの混合物Aに添加し、窒素パージ雰囲気中、磁気撹拌棒で継続的に撹拌した。
4.材料を撹拌棒で混合し続けられないほど粘性になる(硬化する)まで混合し続け、膨潤エラストマーを形成した。この硬化は約35分後に起こった。
5.2.41gの追加のD5を4.51gの膨潤エラストマーを添加し、13%の所望の最終エラストマー含有量(FEC)を達成した。実施例2の補法を用い、これらの非球状エラストマー粒子のペーストを生成した。最終生成物はゲル化溶媒だった。
Claims (5)
- 分子当たりの平均で少なくとも2つのフリーラジカル重合性基を有する少なくとも1つのオルガノポリシロキサンである成分(A)を、少なくとも1つの有機ボランフリーラジカル開始剤である成分(B)、成分(A)との少なくとも1つの混和性流体である成分(C)、及び酸素と混合して反応混合物を形成する工程と、
該反応混合物をゲル化して実質的に均質な膨潤シリコーンゲルを形成する工程であって、該ゲル化する工程は、成分(A)を、成分(B)、成分(C)、及び酸素の存在下、5℃〜95℃の温度を維持しながら重合させ、実質的に均質な膨潤シリコーンゲルを形成する工程を含む、ゲル化する工程と、を含み、
該実質的に均質な膨潤シリコーンゲルの50(重量)%〜90(重量)%は成分(C)であり、
該実質的に均質な膨潤シリコーンゲルは、実質的にモノリシックであることを特徴とする、シリコーン組成物の調製方法。 - 前記重合させる間、前記温度が10℃〜35℃で維持され、前記膨潤シリコーンゲルが不希釈状態の膨潤シリコーンゲルのエラストマー成分の固有のプラトーせん断弾性率の1/2以下のプラトーせん断弾性率を有する、請求項1に記載の方法。
- 請求項1〜2のいずれか1項に記載の方法によってシリコーン組成物を調製し、得られた膨潤シリコーンゲルをせん断し、該膨潤シリコーンゲルのエラストマー成分及び成分(C)と相溶性である少なくとも1つの混和性流体によって任意に希釈し、膨潤シリコーン微粒子を含むシリコーンペーストを形成する方法であって、該任意の混和性流体が、成分(C)と同じか、成分(C)と異なるか、又は、その組み合わせの1つである工程を含む、方法。
- 前記希釈のための任意の混和性流体が、シリコーンから選択される、請求項1〜3のいずれか1項に記載の方法。
- 成分(A)が、アクリレート及びメタクリレート官能性ポリジメチルシロキサン及び樹脂、メタクリロキシプロピルジメチルシロキシ末端ポリジメチルシロキサン、メタクリロキシメチルシロキシ末端ポリジメチルシロキサン、アクリロキシプロピルジメチルシロキシ末端ポリジメチルシロキサン、アクリロキシメチルジメチルシロキシ末端ポリジメチルシロキサン、ポリジメチルシロキサン−ポリメチル−メタクリロキシプロピルシロキサンコポリマー、及びポリジメチルシロキサン−ポリメチル−アクリロキシプロピルシロキサンコポリマーから選択される少なくとも1種であり;成分(B)が、トリアルキルボラン−有機窒素錯体であり、該トリアルキルボランがトリエチルボラン、トリ−n−ブチルボラン、トリ−n−オクチルボラン、トリ−sec−ブチルボラン、及びトリドデシルボランから選択される少なくとも1種であり;重合が、イソホロンジイソシアネート、酢酸、及びカルボキシル末端ポリジメチルシロキサンから選択される少なくとも1つの有機窒素反応性化合物である成分(D)の存在下、アクリレート、メタクリレート、及びこれらのいずれかの組み合わせから選択される少なくとも1つのフリーラジカル重合性有機コモノマーである成分(E)の存在下、並びに/又は、ビタミン、サンスクリーン、植物抽出物、芳香剤又は香料、局所薬剤活性物質、タンパク質、酵素、制汗剤、デオドラント、保湿剤、抗真菌剤、及び抗菌剤から選択される少なくとも1種である、パーソナルケア及びヘルスケア製品に用いるのに適した少なくとも1つの活性成分である成分(F)の存在下で行われるか、形成された前記膨潤シリコーンゲルがこれらによって処理される、請求項1〜4のいずれか1項に記載の方法。
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- 2010-10-19 EP EP10821448.7A patent/EP2490663B1/en active Active
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EP2490663A2 (en) | 2012-08-29 |
JP2013508374A (ja) | 2013-03-07 |
WO2011049896A2 (en) | 2011-04-28 |
US9243113B2 (en) | 2016-01-26 |
JP2016094399A (ja) | 2016-05-26 |
CN102666665A (zh) | 2012-09-12 |
CN102666665B (zh) | 2015-07-22 |
WO2011049896A3 (en) | 2011-08-11 |
US20120219517A1 (en) | 2012-08-30 |
KR20120102053A (ko) | 2012-09-17 |
KR101884772B1 (ko) | 2018-08-03 |
EP2490663B1 (en) | 2017-09-20 |
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