JP2013520530A - 改質表面を有するヒドロゲルおよびヒドロゲル微小粒子 - Google Patents
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子 Download PDFInfo
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- JP2013520530A JP2013520530A JP2012554020A JP2012554020A JP2013520530A JP 2013520530 A JP2013520530 A JP 2013520530A JP 2012554020 A JP2012554020 A JP 2012554020A JP 2012554020 A JP2012554020 A JP 2012554020A JP 2013520530 A JP2013520530 A JP 2013520530A
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- hydrogel
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- extract
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Classifications
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- 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
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- 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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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D183/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D183/04—Polysiloxanes
- C09D183/06—Polysiloxanes containing silicon bound to oxygen-containing groups
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- 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
- C08J3/12—Powdering or granulating
- C08J3/126—Polymer particles coated by polymer, e.g. core shell structures
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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
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- C08L33/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D133/00—Coating compositions based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Coating compositions based on derivatives of such polymers
- C09D133/02—Homopolymers or copolymers of acids; Metal or ammonium salts thereof
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D143/00—Coating compositions based on 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; Coating compositions based on derivatives of such polymers
- C09D143/04—Homopolymers or copolymers of monomers containing silicon
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- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
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Abstract
Description
様々な実施形態において、ヒドロゲルおよびヒドロゲルの微小粒子の表面を改質する方法を提供する。提供されている方法によって、既知のヒドロゲルおよびヒドロゲル微小粒子の表面を改質することができる。また、未処理のヒドロゲルおよびヒドロゲル微小粒子の調製方法も既知であり、それらの種類および使用に応じて異なる。良好な結果が、カーボポール(登録商標)ポリアクリル酸ゲルおよび微小粒子の使用で得られるが、当業者は本明細書に記載の方法および組成物がこのようなゲルおよび微小粒子を制限されるものではないと評価している。
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の調製において、成分(A)は、少なくとも1つの水に相溶性のある有機ポリマー、アルコールに相溶性のある有機ポリマーおよびその組み合わせから選択される。ポリマーは、ホモポリマーであってもへテロポリマー(制限されるものではないが、あらゆるコモノマー分布のクロスポリマーまたは共重合体)であってもよく、あらゆる範囲で、線状、分岐、超分岐、デンドリマーまたは架橋とすることができる。適切なポリマーの例としては、特に制限されるものではないが、ゼラチン、メチルセルロース、ヒドロキシエチルメチルセルロース、ヒドロキシプロピルメチルセルロース、ポリエチレンオキシド、ポリアクリルアイド、ポリアクリル酸、ポリメタクリル酸、ポリアクリル酸の塩、ポリメタクリル酸の塩、ポリ(2−ヒドロキシエチルメタクリレート)、ポリ乳酸、ポリグリコール酸、ポリビニルアルコール、ポリ無水物(例えばポリ(メタクリル)無水物、ポリ(アクリル酸)無水物、ポリセバシン酸無水物)、コラーゲン、ポリ(ヒアルロン酸)、ヒアルロン酸を含有するポリマーおよび共重合体、ポリペプチド、デキストラン、硫酸デキストラン、キトサン、キチン、アガロースゲル、ファイブリンゲル、大豆由来ヒドロゲルおよびアルギン酸系ヒドロゲル(例えばポリ(アルギン酸ナトリウム))およびその組み合わせが挙げられる。
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の調製において、成分(B)は水、水に相溶性のあるアルコールまたはその組み合わせに不溶性である、少なくとも1つのフリーラジカル重合性化合物から選択される。いくつかの実施形態において、フリーラジカル重合性化合物は、有機モノマー、オリゴマーおよびポリマー;有機ポリシロキサン;およびその組み合わせとすることができる。
(1)R1 3SiO(R1 2SiO)a(R1R2SiO)bSiR1 3;
aは0〜20,000、bは1〜20,000であり;それぞれR1基は独立して水素、ハロゲンまたは一価の有機基であり、それぞれR2基は独立して一価の不飽和有機基であり、
(2)R3 2R4SiO(R3 2SiO)c(R3R4SiO)dSiR3 2R4;
cは0〜20,000、dは0〜20,000であり;それぞれR3基は独立して水素、ハロゲンまたは一価の有機基であり、それぞれR4基は独立して一価の不飽和有機基である
から選択される式で表され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。
いくつかの実施形態において、改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の双方の調製は、適切な溶媒の存在下、成分(B)を任意に処理する工程を伴う。いくつかの実施形態において、成分(B)に適切な溶媒としては、水に不溶性な溶媒、例えばシリコーン、有機化合物および“環境に配慮した”溶媒、例えばイオン液体および臨界超過の流体;およびその混合物から選択することができる。溶媒の適切な例としては、特に制限されるものではないが、線状、分岐、超分岐および環状オルガノシロキサン流体、例えばヘキサメチルジシロキサン、オクタメチルトリシロキサン、デカメチルテトラシロキサンおよび25℃で1000cP未満の粘度を有するトリメチルシリル末端ポリジメチルシロキサン流体またはその混合物;カプリリルメチルトリシロキサン;オクタメチルシクロテトラシロキサン;デカメチルシクロペンタシロキサン;およびより高いシクロシロキサンならびにその混合物が挙げられる。いくつかの実施形態において、トリメチルシリル末端ポリジメチルシロキサン流体が、成分(B)の溶媒として適している。いくつかの実施形態において、適切なトリメチルシリル末端ポリジメチルシロキサン流体は25℃で約0.5〜約100cPの粘度を有する。他の適切な溶媒としては、特に制限されるものではないが、水に不溶性の有機溶媒、例えばペンタン、ヘキサン、ヘプタン、オクタン、シクロヘキサン、トルエン、キシレン、酢酸エチルが挙げられる。さらに、成分(B)に適切な溶媒の例としては、特に制限されるものではないが、1−エテニル−3−エチル−イミダゾリウムヘキサフルオロフォスフェートおよびテトラプロピルアンモニウムテトラシアノホウ酸を含む有機油、例えばイソドデカン、イソヘキサデカン、イソデシルネオペンタノエート、イソノニルイソノナノエート、イソパラフィン、イソアルカンおよびイオン液体ならびに超臨界流体、例えば超臨界二酸化炭素が挙げられる。
表面処理したヒドロゲルおよびヒドロゲル微小粒子の双方の調製において、成分(C)はフリーラジカルを生成し、フリーラジカル付加重合を開始および/または架橋することができる、少なくとも1つの有機ボラン化合物である。環境条件で自然発火性でない有機ボランを生成する、安定した有機ボラン化合物を使用することができる。いくつかの実施形態において、成分(C)は、有機ボランおよび適切な有機窒素(例えばアミン)から形成された複合体であって、環境条件で安定性のある複合体を生じ、フリーラジカルは酸素の存在下、有機窒素の反応性化合物の導入に応じて生成される(そして重合が開始される)。いくつかの実施形態において、成分(C)は、有機ボラン化合物であって、フリーラジカルは、加熱によって生成される(そして重合が開始される)。いくつかの実施形態において、成分(C)は、溶媒安定性の有機ボラン(例えばTHF中のトリアルキルボランの溶液)であって、溶媒を蒸発し、ボランを活性化することで、ラジカルが生成される。
R6、R7およびR8は独立して水素、シクロアルキル基、骨格に1〜12個の炭素原子を有する線状または分岐アルキル基、アルキルアリール基、オルガノシラン基、例えばアルキルシラン基またはアリールシラン基、オルガノシロキサン基、他のホウ素原子の共有ブリッジとして機能することができるアルキレン基、他のホウ素原子の共有ブリッジとして機能することができる二価のオルガノシロキサン基またはそのハロゲン置換ホモログから選択され;R9、R10およびR11はホウ素を用いて複合体を形成することができるアミン化合物またはポリアミン化合物が得られる基であり、独立して水素、1〜10個の炭素原子を含むアルキル基、1〜10個の炭素原子を含むハロゲン置換アルキル基または有機ケイ素官能基から選択され、少なくとも1つのR6基、R7基およびR8基ならびに少なくとも2つのR9基、R10基およびR11基を組み合わせて、複素環構造を形成し、但し2つの組み合わせの基からの原子数の合計は11以下である)で表される複合体から選択することができる有機ボラン−有機窒素の複合体である。
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の調製において、成分(D)はヒドロゲルまたはヒドロゲル微小粒子により吸収することができる、少なくとも一つの溶媒である。いくつかの実施形態において、吸収性溶媒は、水、水に相溶性のアルコール、ジオール、ポリオールおよびその組み合わせから選択することができる。適切なアルコールの例としては、特に制限されるものではないが、メタノール、エタノール、イソプロピルアルコール、エチレングリコール、ポリエチレングリコールおよびその組み合わせが挙げられる。いくつかの実施形態において、吸収性溶媒は、1以上の水に相溶性のアルコールと水との組み合わせとすることができる。
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の両方の調製において、任意成分(E)は、少なくとも1つの有機窒素反応性化合物を、成分(C)の有機ボラン−有機窒素の複合体と組み合わせ、酸化環境にさらしたとき、有機ボラン−有機窒素の複合体の解離が生じ、これにより、フリーラジカル重合および/または架橋が開始される。このような有機窒素反応性化合物の存在は、重合および/または架橋が室温条件を含む解離温度以下の温度で迅速に生じることを可能とする。
改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の調製において、任意成分(F)は少なくとも1つのパーソナルケアおよびヘルスケアの有効成分、または少なくとも1つの農業上の有効成分から選択される。いくつかの実施形態において、成分(F)をin situでのカプセル化のため、ヒドロゲルまたはヒドロゲル微小粒子に添加することができ、添加はヒドロゲルまたはヒドロゲル微小粒子を成分(B)および(C)を用いて処理する前、成分(B)および(C)を用いて処理した後、成分(B)および(C)を用いて処理している間、またはその組み合わせとすることができる。いくつかの実施形態において、熱感受性の有効成分を、熱応答または熱分解の閾値温度以下でヒドロゲルまたはヒドロゲル微小粒子に取り入れることができる。いくつかの実施形態において、ヒドロゲルまたはヒドロゲル微小粒子中に懸濁された有効成分を、必須ではないが、微粒子型とすることができる。有効成分がカプセル化の条件で微粒子型である場合、その粒子のサイズ、分布または形は特に制限されるものではない。ヒドロゲルまたはヒドロゲル微小粒子の他の成分を厳選することによって、有効成分の放出の所望の機能を達成できる。放出機能の例としては、熱、機械的もしくは化学的な抽出、溶解、膨張、溶融、軟化、分解、研磨、絞りまたはクラッキングまたは放射線誘導性のストレスが挙げられる。
いくつかの実施形態によると、少なくとも1つの界面活性剤を、本明細書に記載の方法によるヒドロゲルおよびヒドロゲル粒子の処理の際、任意に添加することができる。原則としては、使用される界面活性剤は、あらゆる既知の界面活性剤とすることができ、カチオン、アニオン、非イオンおよび/または両性とすることができる。さらに、界面活性剤は水性、非水および/または希釈または薄められていない形とすることができる。
組成物は、任意に付加的な成分を提供することができる。特に制限されるものではないが、かかる任意付加成分の例としては、界面活性剤、乳化剤;分散剤;レオロジー重合調整剤、例えば増粘剤;密度調整剤;アジリジン安定剤;ポリマー;希釈剤;酸受容体;抗酸化物質;熱安定剤;難燃剤;除去剤;シリル化剤;気泡安定剤;溶媒;希釈剤;可塑剤;充填剤および無機粒子、顔料、染料ならびに防湿剤が挙げられる。
様々な実施形態において、改質表面を有するヒドロゲルおよびヒドロゲル微小粒子を提供する。このようなヒドロゲルおよび微小粒子は、(i)成分(B);および(ii)成分(C)とともに、成分(A)を含むヒドロゲルおよび微小粒子を処理する工程を含む方法によって調製され、前記処理は、酸素の存在下で行われ、少なくとも1つの改質表面は処理されたヒドロゲルまたはヒドロゲル微小粒子に形成される。
<ポリアクリル酸ヒドロゲルの製造方法>
ポリアクリル酸ヒドロゲルを下記の方法によって、実験室の環境条件下で調製した:
1. 30部の脱イオン水および10部のアクリル酸を均一になるまでガラスバイアルを手動で振とうした。
2. 振とう後、1部のTNBB−MOPA(1.3モル等量の3−メトキシプロピルアミンとトリ−n−ブチルボランを複合させた)を添加し、サンプルがゲルを形成するまでバイアルを手動で振とうすることによってサンプルをさらに混合した。組成物を非流動性に重合するまで、2分未満の時間で観測した。
<シリコーン改質表面を有するポリアクリル酸ヒドロゲルモノリス>
シリコーンの表面コーティングを用いたヒドロゲルモノリスを、下記の方法によって実験室の環境条件下で調製した:
1. 実施例1からの組成物から形成したヒドロゲルを、ポリスチレン秤量皿に完全にゲルを形成する前に入れた。その後、前記材料が、完全にゲルを形成するまでそのままにした。
2. 72部のヘキサメチルジシロキサン(揮発性溶剤)、24部のMA−PDMS(平均分子量約8,000g/molのメタクリルオ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)および4部のTEB−PDA(トリエチルボラン−1,3−ジアミノプロパン複合体)の混合物を調製した。
3. ヒドロゲルモノリスの表面をシリコーン混合物で覆い、10分間そのままにした。
4. 10分後、過剰量の混合物をデカンテーションにより取り除き、モノリスを付加的なヘキサメチルジシロキサン、その後イソプロピルアルコール(IPA)(Fischer組織学的グレード)を用いて洗浄し、あらゆる未反応の成分を取り除いた。
<シリコーン改質表面を有するポリアクリル酸ヒドロゲルモノリス>
実施例2において使用した方法は、ヘキサメチルシロキサン中の50%および75%のMA−PDMS溶液を用いて繰り返された。実施例2に記載されているようなATR−IRによる分析は、2962cm−1および1258cm−1において、MA−PDMSの上昇した濃度およびより弱い水のピークで、比例して強いPDMSピークを示す。
<シリコーン改質表面を有する部分的に膨張したヒドロゲル粒子>
シリコーン表面を用いたヒドロゲル粒子を、下記の方法によって、実験質の環境条件下でおいて調製した:
1. 4.2部の微小粒子架橋ポリアクリル酸(μPAA−1)[カーボポール(登録商標)ETD 2020(アクリレート/C10−30アルキルアクリレートクロスポリマー粒子]、12.7部のMA−PDMSおよび0.6部のソルビタンモノオレエートを77.9部のヘキサメチルジシロキサンに8oz.の棒瓶中で組み合わせ、均一となるまでマグネチックスターラーで撹拌した。
2. 4.0部の水を滴下すると同時に、10分間以上混合し、撹拌した。
3. 0.7部のTNBB−MOPAを混合物に添加し、15分間以上撹拌した。
4. 生成した物質を0.22ミクロンのテフロンフィルターを経て濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンを用いて洗浄した。
5. 生成した物質を2時間、室温で完全な真空で乾燥した。
6. 生成した物質を脱イオン水に添加し、1重量%の分散剤を形成し、周囲の実験条件において1時間未満でゲルを形成した。
<シリコーン改質表面を有するヒドロゲル粒子を用いたゲル形成した水組成物>
継続的にゲル形成した水組成物を、下記の方法によって実験質の環境条件下で調製した:
1. 実施例4からのシリコーン改質を有するヒドロゲル粒子を、真空オーブン30℃で、2時間の真空で乾燥した。
2. 1部の乾燥したシリコーン改質を有する粒子を、99部の脱イオン水と共に適切なガラスバイアルに配置し、バイアルをリストアクションシェーカーに配置し、定期的に取り外すことによって観測した。
<モノリシックヒドロゲルの耐水性シリコーンコーティング>
染色したヒドロゲルモノリスを下記のように調製した。
1. ガラスバイアル中の73部の脱イオン水に、数滴の黄色の食品着色料および24部のアクリル酸を添加した。バイアルに蓋をして、均一な黄色の溶液になるまで振とうした。
2. 3部のTNBB−MOPAを混合物に添加した。溶液に蓋をして、3−4秒間激しく振とうした。
3. バイアルの中身を2つのポリスチレン秤量皿に入れ、皿で完全に重合させ、染色したヒドロゲルモノリスを形成した。
4. 染色したヒドロゲルモノリスを3回ヘキサメチルジシロキサン、3回IPAで洗浄し、圧縮された空気で乾燥した。
1. ガラスバイアル中で47部のMA−PDMS、47部のヘキサメチルジシロキサンおよび6部のTEB−PDAを混合した。バイアルに蓋をして、手動で均一になるまで振動した。
2. 混合物を硬化した黄色に染色したヒドロゲルモノリスの1つの表面上に入れ、接触部位に迅速に硬化したシリコーンコーティングを形成した。
3. 15分後、過剰量のシリコーン混合物をヒドロゲル表面から静かに入れ、ゲルを3回ヘキサメチルジシロキサン、3回IPAで洗浄し、圧縮された空気で乾燥した。
1. 青い食品着色料で着色した水3滴を、シリコーン処理したヒドロゲルおよび未処理のヒドロゲルモノリスの双方の表面の中央に添加した。
2. 95分後、ティッシュを使用して、青い染色水をヒドロゲルの表面から拭き取った。
<シリコーン改質表面を有するヒドロゲル粒子>
シリコーン改質表面を有するヒドロゲル粒子を、実施例4に記載されているように調製し、疎水改質した微小粒子を架橋したポリアクリル酸の共重合体(μPAA−cp)[カーボポール(登録商標)Ultrez 20(アクリレート/C10−30アルキルアクリレート架橋ポリマー粒子)]をμPAA−1と置換した。改質表面を有するヒドロゲル粒子で、実施例5に記載されている方法と同様に水をゲル化した。
<シリコーン改質表面を有するヒドロゲル粒子>
シリコーン改質表面を有するヒドロゲル粒子を実施例4に記載されているように調製し、異なる勾配の微小粒子と架橋したポリアクリル酸の共重合体(μPAA−2)[カーボポール(登録商標)ETD 2050(Carbomer)]をμPAA−1と置換した。改質表面を有するヒドロゲル粒子で、実施例5に記載された方法と同様に水をゲル化した。
<膨張したシリコーン改質表面を有するヒドロゲル粒子>
より高度に膨張したシリコーン改質表面を有するヒドロゲル粒子を、実施例4に記載されているように調製し、水とμPAA−1の比率を1:1〜2:1および3:1に上昇させた。
<シリコーン改質表面を有するヒドロゲル粒子>
実施例4の方法を、同様の構造を有するが、13,000g/molの平均分子量のMA−PDMSのより高い分子量を用いて繰り返した。それから、サンプルを、実施例5の方法を用いてさらに水和し、水和ゲルを形成した。
<シリコーン改質表面を有するヒドロゲル粒子>
実施例4の方法を、同様の構造を有するが、36,000g/molの分子量を有するMA−PDMSのより高い分子量の置換物を用いて繰り返した。それから、サンプルを実施例5の方法を用いてさらに水和し、水和ゲルを形成した。
<弾性率のレオロジー試験>
異なる水和レベルでを有する様々なヒドロゲルサンプルの弾性率の測定を、Rheometrics Dynamic Analyzer RDA II血流計の平行板の形状を使用した周波数掃引法を用いて行った。報告された弾性率は、1%のひずみ、10rad/sの周波数で測定した、動的貯蔵弾性率(G’)からのプラトー弾性率の値である。この値を、エラストマー物質と関連のあるG’の最も典型的なものとして選択した。より高い濃度のゲルを洗浄後、フィルターから取り外し、8mmまたは25mmのいずれかの直径のプレートに一致する金型を用いて型に合わせて打ち抜いた。通常、サンプルの厚さは、1−3mmである。まず、最も低い濃度のサンプル(G’<103Pa)を脱イオン水で相当する希釈レベルまで希釈し、40mm直径の平行板から打ち抜くことなく前もってせん断し、それから、テフロンのへらを用いて一定のサイズまで整えた。分析の際に集めたデータをTA Orchestrator Version V7.1.2.3を用いて処理した。全ての試験は室温で実施した。
*処理は実施例4と同様であった:5部のμPAA−1、1部のソルビタンモノオレエート、89部のヘキサメチルジシロキサンを組み合わせ、磁器撹拌器を用いて混合した。5部の水を滴下すると同時に最低10分間撹拌した。1部のTNBB−MOPAを混合物に添加し、それから最低15分間継続して混合した。生成した物質を0.22ミクロンのテフロンフィルターを通して真空濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンを用いて洗浄した。物質を2時間、室温、十分な真空(<5mm Hg)で乾燥した。
<シリコーン改質表面を有する部分的に膨張したヒドロゲル粒子>
シリコーン表面とヒドロゲル粒子を下記の方法によって、実験質の環境条件下で調製した:
1. 3.6部の非イオンの高分子量のポリエチレンオキシド水溶性ポリマー(PEO)(Polyox(商標)WSR301 NF品質)、11.5部のMA−PDMSおよび1.8部のソルビタンモノオレエートを、77.0部のヘキサメチルジシロキサンに8oz.の棒瓶中で組み合わせ、手持ち式のホモジナイザーを用いて混合し、十分な混合を達成した。
2. 5.6部の水中の3.7%の塩酸を滴下しながら混合した。
3. 0.5部のTNBB−MOPAを混合物に添加しながら混合した。混合をさらに1分間継続した。
4. 生成した物質を、0.8ミクロンのナイロンフィルターを通して真空濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンで洗浄した。
5. 生成した物質を一晩、実験室の環境条件下で乾燥した。
<シリコーン改質表面を有する部分的に膨張したヒドロゲル粒子>
シリコーン表面とヒドロゲル粒子を下記の方法によって、実験質の環境条件下で調製した:
1. 5.7部のMA−PDMS、90.1部のヘキサメチルジシロキサンと、4部のソルビタンモノオレエート、36.3部の脱イオン水、18.7部のエタノール、3.8部の氷酢酸および37.1部の部分的にヒドロキシプロピル置換されたメチルセルロース(Methocel E50)からなる混合物3.2部とを、8oz.の棒瓶中で組み合わせ、手持ち式のホモジナイザーを用いてかき混ぜた。
2. 1.1部のTNBB−MOPAを混合物に添加した。混合物をさらに数分間均一にした。
3. 生成した物質を、5ミクロンのナイロンフィルターを通して真空濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンで洗浄した。
4. 生成した物質を、2時間、40℃で十分な真空(<5mm Hg)で乾燥した。
<シリコーン改質表面を有する部分的に膨張したヒドロゲル粒子>
シリコーン表面を有するヒドロゲル粒子を、下記の方法によって実験質の環境条件下で調製した:
1. 3.8部のゼラチン(Knox(登録商標)Original Gelatin)および10.8部のソルビタンモノオレエートを79.9部のヘキサメチルジシロキサンに8oz.の棒瓶中で組み合わせ、均一になるまでマグネチックスターラーで撹拌した。
2. 3.3部の5%氷酢酸水溶液を滴下しながら、混合および撹拌を最低10分間継続した。
3. 0.5部のTNBB−MOPAを混合物に添加し、最低15分間撹拌した。
4. 生成した物質を0.8ミクロンのナイロンフィルターを通して真空濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンで洗浄した。
5. 生成した物質を2時間、40℃で十分な真空(<5mm Hg)で乾燥した。
<カプセルに包んだ活性シリコーン改質表面を有する部分的に膨張したヒドロゲル粒子>
シリコーン表面を有するヒドロゲル粒子を下記の方法によって、実験の環境条件下で調製した:
1. 6.5部のμPAA−cp、12.7部のMA−PDMSおよび3.1部のソルビタンモノオレエートを70.0部のヘキサメチルジシロキサンに8oz.の棒瓶中で組み合わせ、均一を達成するまで磁石皿で撹拌した。
2. 82部の3.7%塩酸の水溶液中の18部のリドカインからなる6.6部の混合物を滴下しながら混合した。
3. 1.1部のTNBB−MOPAを混合物に添加し、最短さらに2分間混合した。
4. 生成した物質を0.8ミクロンのナイロンフィルターを通して真空濾過し、ヘキサメチルジシロキサンおよびn−ヘプタンで洗浄した。
5. 生成した物質を2時間、40℃、十分な真空(<5mm Hg)で乾燥した。
1. 工程5からの0.26gの乾燥した生成物質を、1時間、50℃、リストアクションシェーカーによる振とうによって、15mLの1NのHCl中で抽出した。
2. 溶液を10分、1500rpmで遠心分離機にかけた。
3. 1mLの上清を10mLのHPLC品質のメタノールに希釈し、30:70のアセトニトリル:5%HOAc pH3.4(1N NaOHで調整)の、流量0.4mL/mL(検出:PDA254nm)のカラム温度30℃で実施した移動相を用いた、Waters Acquity UPLC(2.1×100mm BEH C18 1.7μmカラム)により分析した。
Claims (20)
- 改質表面を有するヒドロゲルおよびヒドロゲル微小粒子の調製方法であって、
少なくとも1つの水に相溶性のある有機ポリマー、アルコールに相溶性のある有機ポリマーまたはこれらの組み合わせである成分(A)を含む、ヒドロゲルまたはヒドロゲル微小粒子を、(i)水、水に相溶性のあるアルコールまたはこれら組み合わせとは相溶性を有しない、少なくとも1つのフリーラジカル重合性化合物である成分(B)と;(ii)少なくとも1つの有機ボランフリーラジカル開始である成分(C)とによって処理する工程を含み、前記処理工程は酸素の存在下で実施し、
少なくとも1つの改質表面は、処理されたヒドロゲルまたはヒドロゲル微小粒子上に形成される、方法。 - ヒドロゲルまたはヒドロゲル微小粒子は、水、アルコールおよびその組み合わせから選択される少なくとも1つの吸収性溶媒である成分(D)を含むか、成分(D)で処理される、請求項1に記載の方法。
- 成分(A)は、ゼラチン、メチルセルロース、ヒドロキシエチルメチルセルロース、ヒドロキシプロピルメチルセルロース、ポリエチレンオキシド、ポリアクリルアミド、ポリアクリル酸、ポリメタクリル酸、ポリアクリル酸の塩、ポリメタクリル酸の塩、ポリ(2−ヒドロキシエチルメタクリレート)、ポリ乳酸、ポリグリコール酸、ポリビニルアルコール、ポリ無水物、例えばポリ(メタクリル)無水物、ポリ(アクリル)無水物、ポリセバシン無水物、コラーゲン、ポリ(ヒアルロン酸)、ポリペプチド、デキストラン、硫酸デキストラン、キトサン、キチン、アガロースゲル、フィブリンゲル、大豆由来のヒドロゲルならびにアルギン酸系ヒドロゲル、例えばポリ(アルギン酸ナトリウム)およびこれらの組み合わせから選択される、請求項1に記載の方法。
- 成分(A)は、ポリアクリル酸、ポリ(メタ)アクリル酸、ポリアクリル酸の塩、ポリメタクリル酸、ポリメタクリル無水物およびポリアクリル無水物から選択される、請求項3に記載の方法。
- 成分(B)は、フリーラジカル重合性有機モノマー、オリゴマーおよびポリマー;フリーラジカル重合性オルガノポリシロキサン;フリーラジカル重合性シラン;およびこれらの組み合わせから選択される、請求項1に記載の方法。
- 成分(B)は、アクリレート官能性ポリジメチルシロキサン、メタクリレート官能性ポリジメチルシロキサン、シラン、樹脂、アクリルオキシアルキル−アルコキシシラン、メタクリルオキシアルキル−アルコキシシラン、アクリレート末端ポリジメチルシロキサン、テトラメチル、ジメタクリルオキシプロピル−ジシロキサン、3−メタクリルロイプロピルトリメトキシシラン、メタクリルオキシプロピルジメチリウシロキシ末端ポリジメチルシロキサン、メタクリルオキシメチルシロキシ末端ポリジメチルシロキサン、アクリルオ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、アクリルオ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−メタクリルオキシプロピルシロキサン共重合体およびポリジメチルシロキサン−ポリメチルーアクリルオキシプロピルシロキサン共重合体から選択されるフリーラジカル重合性オルガノポリシロキサンである、請求項5に記載の方法。
- 成分(C)は、トリエチルボラン−プロパンジアミン、トリエチルボラン−ブチルイミダゾール、トリエチルボラン−メトキシプロピルアミン、トリ−n−ブチルボラン−メトキシプロピルアミンおよびトリエチルボラン−アミノシランまたはトリエチリウボラン−アミノシロキサンの複合体から選択される、請求項1に記載の方法。
- 成分(D)は水、メタノール、エタノールおよびイソプロピルアルコールから選択される、請求項2に記載の方法。
- ヒドロゲルまたはヒドロゲル微小粒子は、少なくとも1つの有機窒素反応性化合物である成分(E)の存在下で処理される、請求項1に記載の方法。
- 成分(E)は、酸、無水物、イソシアネート、エポキシドおよびアルデヒドから選択される、請求項9に記載の方法。
- ヒドロゲルまたはヒドロゲル微小粒子は、パーソナルケアまたはヘルスケア有効成分および農業上の有効成分から選択される、少なくとも1つの有効成分である成分(F)を含むか、成分(F)で処理される、請求項1に記載の方法。
- 前記有効成分は、ビタミンC、緑茶抽出物、リドカイン、ニコチン、ナイアシンアミド、サリチル酸、ケトプロフェン、ケトコナゾールおよび尿素から選択される、請求項11に記載の方法。
- 前記有効成分は、尿素、硝酸アンモニウム、硝酸カリウム、硝酸ナトリウム、リン酸カリウムおよびリン酸アンモニウムから選択される、請求項11に記載の方法。
- ヒドロゲルまたはヒドロゲル微小粒子は、少なくとも1つの界面活性剤である成分(G)の存在下で処理される、請求項1に記載の方法。
- 界面活性剤は、テルギトール 15−s−3、テルギトール 15−s−40、ソルビタンモノオレエート、ポリリコール修飾したトリメチルシリル化シリケート、ポリグリコール修飾したシロキサン、ポリグリコール修飾したシリカ、エトキシ化第四級アンモニウム塩溶液および塩化セチルトリメチルアンモニウム溶液から選択される、請求項14に記載の方法。
- ヒドロゲルまたはヒドロゲル微小粒子は、ヘキサメチルジシロキサン;オクタメチルトリシロキサン;デカメチルテトラシロキサン;25℃で1000cP未満の粘度を有するトリメチルシリル末端ポリジメチルシロキサン流動体;カプリリルメチルトリシロキサン;オクタメチルシクロテトラシロキサン;デカメチルシクロペンタシロキサン;ペンタン;ヘキサン;ヘプタン;オクタン;シクロヘキサン;トルエン;キシレン;酢酸エチル;イソドデカン;イソヘキサデカン;イソデシルネオペンタノエート;イソノニルイソノナノエート;イソパラフィン;イソアルカン;1−エテニル−3−エチル−イミダゾリウムヘキサフルオロホスファート;テトラプロピル−アンモニウムテトラシアノボレート;超臨界炭酸ガス;およびその組み合わせから選択される少なくとも1つの成分(B)に適切な溶媒の存在下処理される、請求項1に記載の方法。
- 請求項1に記載の方法により調製した改質表面を有するヒドロゲル。
- 請求項1に記載の方法により調製した改質表面を有するヒドロゲル微小粒子。
- 請求項2,3,5,7,9,11,14,15または16に記載の方法により調製した改質表面を有するヒドロゲル。
- 請求項2,3,5,7,9,11,14,15または16に記載の方法により調製した改質表面を有するヒドロゲル微小粒子。
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US9574109B2 (en) | 2017-02-21 |
JP5860819B2 (ja) | 2016-02-16 |
US20120309623A1 (en) | 2012-12-06 |
EP2536786A1 (en) | 2012-12-26 |
KR20130036002A (ko) | 2013-04-09 |
EP2536786B1 (en) | 2015-12-30 |
KR101825607B1 (ko) | 2018-02-05 |
CN102762655B (zh) | 2016-05-11 |
CN102762655A (zh) | 2012-10-31 |
WO2011109174A1 (en) | 2011-09-09 |
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