JP5537954B2 - 新規なpdms−pvpブロックコポリマー - Google Patents
新規なpdms−pvpブロックコポリマー Download PDFInfo
- Publication number
- JP5537954B2 JP5537954B2 JP2009553775A JP2009553775A JP5537954B2 JP 5537954 B2 JP5537954 B2 JP 5537954B2 JP 2009553775 A JP2009553775 A JP 2009553775A JP 2009553775 A JP2009553775 A JP 2009553775A JP 5537954 B2 JP5537954 B2 JP 5537954B2
- Authority
- JP
- Japan
- Prior art keywords
- pyrrolidinone
- diblock copolymer
- compound
- amphiphilic diblock
- butyl
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Fee Related
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- 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
- C08F293/00—Macromolecular compounds obtained by polymerisation on to a macromolecule having groups capable of inducing the formation of new polymer chains bound exclusively at one or both ends of the starting macromolecule
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L15/00—Chemical aspects of, or use of materials for, bandages, dressings or absorbent pads
- A61L15/16—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons
- A61L15/22—Bandages, dressings or absorbent pads for physiological fluids such as urine or blood, e.g. sanitary towels, tampons containing macromolecular materials
- A61L15/26—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds; Derivatives thereof
-
- A—HUMAN NECESSITIES
- A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
- A61L—METHODS OR APPARATUS FOR STERILISING MATERIALS OR OBJECTS IN GENERAL; DISINFECTION, STERILISATION OR DEODORISATION OF AIR; CHEMICAL ASPECTS OF BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES; MATERIALS FOR BANDAGES, DRESSINGS, ABSORBENT PADS OR SURGICAL ARTICLES
- A61L27/00—Materials for grafts or prostheses or for coating grafts or prostheses
- A61L27/14—Macromolecular materials
- A61L27/18—Macromolecular materials obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/10—Acylation
-
- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/14—Esterification
-
- 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
-
- 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
- C08G77/452—Block-or graft-polymers containing polysiloxane sequences containing nitrogen-containing sequences
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L53/00—Compositions of block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Compositions of derivatives of such polymers
-
- 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
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
- G02B1/043—Contact lenses
-
- 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
- C08F2810/00—Chemical modification of a polymer
- C08F2810/40—Chemical modification of a polymer taking place solely at one end or both ends of the polymer backbone, i.e. not in the side or lateral chains
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Physics & Mathematics (AREA)
- Animal Behavior & Ethology (AREA)
- General Chemical & Material Sciences (AREA)
- Veterinary Medicine (AREA)
- Public Health (AREA)
- General Health & Medical Sciences (AREA)
- Epidemiology (AREA)
- Life Sciences & Earth Sciences (AREA)
- General Physics & Mathematics (AREA)
- Materials Engineering (AREA)
- Oral & Maxillofacial Surgery (AREA)
- Dermatology (AREA)
- Optics & Photonics (AREA)
- Hematology (AREA)
- Engineering & Computer Science (AREA)
- Transplantation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Eyeglasses (AREA)
- Materials For Medical Uses (AREA)
- Medicinal Preparation (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Silicon Polymers (AREA)
- Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
Description
の構造を有する両親媒性ジブロックコポリマー化合物である。
の構造を有する両親媒性トリブロックコポリマー化合物である。
の構造を有する、重合性官能基を有する両親媒性ジブロックコポリマー化合物である。
で示される一般的な構造の(メタ)アクリレート化ポリビニルピロリドン化合物も提供する。特定の態様においては、R1はHであり、R3はC(CH3)2−O−CH2−CH2であり、R4はCH3であり、nは10〜1000であるか;或いは、R1はHであり、R3はC(CH3)2であり、R4はHであり、nは10〜1000であるか;或いは、R1はHであり、R3はS−(CH2)3であり、R4はCH3であり、nは10〜1000であるか;或いは、R1はHであり、R3はC(CH3)2−O−C(=O)−NH−(CH2)3であり、R4はCH3であり、nは10〜1000である。この化合物は、コンタクトレンズ配合物における重合性湿潤剤として用いるのに好適である。
当業者に公知の反応を用いて調製したヒドロキシ官能化PVPをメタクリレート化反応することによってメタ(アクリレート)官能化PVPの合成を行う。重合性(メタ)アクリレート化PVPの一般的な構造は、例えば次式:
を有していてよい。
重合性PVPの他の種類を下記に示す。ここでは、重合性官能基は(メタ)アクリルアミド基である。
(メタ)アクリルアミド官能化PVPコポリマーの合成への第1工程は、アゾビス(イソブチロニトリル)(AIBN)などのようなアゾ開始剤を用いて、アミノアルキルメルカプタン連鎖移動剤の存在下、溶媒を用いるか又は用いないで蒸留N−ビニルピロリドンを重合して、10,000〜1,000,000ダルトンの間の異なるMWのアミノ末端PVPを生成させることである。得られるアミノ末端PVPは、メタクリロイルクロリド又は無水メタクリル酸との反応によって(メタ)アクリルアミド末端誘導体に転化させる。この態様の1つの例は、反応式2に示すプロトコールを用いて合成される。
本発明は、また、下式で示される一般的な構造の新規なポリジメチルシロキサン(PDMS)−PVPコポリマー及び他の両親媒性コポリマーの製造方法も提供する。
上記のクラスの物質を製造するための逆合成法は、下記の反応式で示される。
本発明によって与えられる合成方法によれば、下式で示される一般的な構造の新規なPVP−PDMS−PVPトリブロックコポリマー及び他の両親媒性コポリマーの合成も可能である。
上記のクラスの物質を製造するための逆合成アプローチは、下記の反応式で示される。ここでは、実施例3と同様に、最終生成物の前に中間体を、更にその前に出発物質を示している。
本発明の他の態様は、下式で示される重合性官能基を有する一般的な種類の化合物である。
上記のクラスの物質を製造するための逆合成アプローチは反応式5で示される。
Claims (18)
- 請求項1に記載の両親媒性ジブロックコポリマーを含有する、コンタクトレンズ用のレンズケア配合物。
- コンタクトレンズがシリコーンヒドロゲルレンズである、請求項2に記載のレンズケア配合物。
- 請求項1に記載の両親媒性ジブロックコポリマーを含有する、創傷治療具用の酸素透過性で湿潤性の基材として用いるための配合物。
- 請求項1に記載の両親媒性ジブロックコポリマーを含有する、再生医療用の骨格材として用いるための配合物。
- 請求項1に記載の両親媒性ジブロックコポリマーを含有する、制御薬剤放出用配合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3であり;bが1であり;XがOであり;R3がHであり;R4がピロリジノンであり;dが10〜10,000である、請求項1に記載の化合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3−O−(CH2)2であり;bが1であり;XがOであり;R3がHであり;R4がピロリジノンであり;dが10〜10,000である、請求項1に記載の化合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3であり;bが1であり;XがNHであり;R3がHであり;R4がピロリジノンであり;dが10〜10,000である、請求項1に記載の化合物。
- 請求項10に記載の両親媒性ジブロックコポリマーを含有する、シリコーンヒドロゲルレンズの製造において用いるための配合物。
- 請求項10に記載の両親媒性ジブロックコポリマーを含有する、創傷治療具用の酸素透過性で湿潤性の基材の製造において用いるための配合物。
- 請求項10に記載の両親媒性ジブロックコポリマーを含有する、再生医療用の骨格材の製造において用いるための配合物。
- 請求項10に記載の両親媒性ジブロックコポリマーを含有する、制御薬剤放出用の成分の製造において用いるための配合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3であり;bが1であり;XがOであり;R3がHであり;R4がピロリジノンであり;dが1〜10,000であり;R5がC(CH3)2−O−CH2−CH2であり;YがOであり;R6がCH3である、請求項10に記載の化合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3であり;bが1であり;XがOであり;R3がHであり;R4がピロリジノンであり;dが1〜10,000であり;R5がC(CH3)2−O−CH2−CH2であり;YがNHであり;R6がCH3である、請求項10に記載の化合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3であり;bが1であり;XがNHであり;R3がHであり;R4がピロリジノンであり;dが1〜10,000であり;R5がC(CH3)であり;YがOであり;R6がCH3である、請求項10に記載の化合物。
- R1がブチルであり;aが2〜50であり;R2が(CH2)3−O−(CH2)2であり;bが1であり;XがOであり;R3がHであり;R4がピロリジノンであり;dが1〜10,000であり;R5がC(CH3)であり;YがNHであり;R6がCH3である、請求項10に記載の化合物。
Applications Claiming Priority (3)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US89504207P | 2007-03-15 | 2007-03-15 | |
US60/895,042 | 2007-03-15 | ||
PCT/US2008/056825 WO2008112874A1 (en) | 2007-03-15 | 2008-03-13 | Novel pdms-pvp block copolymers |
Related Child Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012157818A Division JP5526376B2 (ja) | 2007-03-15 | 2012-07-13 | 新規なpdms−pvpブロックコポリマー |
Publications (2)
Publication Number | Publication Date |
---|---|
JP2010521561A JP2010521561A (ja) | 2010-06-24 |
JP5537954B2 true JP5537954B2 (ja) | 2014-07-02 |
Family
ID=39760035
Family Applications (2)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2009553775A Expired - Fee Related JP5537954B2 (ja) | 2007-03-15 | 2008-03-13 | 新規なpdms−pvpブロックコポリマー |
JP2012157818A Expired - Fee Related JP5526376B2 (ja) | 2007-03-15 | 2012-07-13 | 新規なpdms−pvpブロックコポリマー |
Family Applications After (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
JP2012157818A Expired - Fee Related JP5526376B2 (ja) | 2007-03-15 | 2012-07-13 | 新規なpdms−pvpブロックコポリマー |
Country Status (7)
Country | Link |
---|---|
US (2) | US8153728B2 (ja) |
EP (1) | EP2132242B1 (ja) |
JP (2) | JP5537954B2 (ja) |
CN (1) | CN101663340B (ja) |
AU (1) | AU2008224989B2 (ja) |
CA (2) | CA2681090C (ja) |
WO (1) | WO2008112874A1 (ja) |
Families Citing this family (17)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US9522980B2 (en) | 2010-05-06 | 2016-12-20 | Johnson & Johnson Vision Care, Inc. | Non-reactive, hydrophilic polymers having terminal siloxanes and methods for making and using the same |
US20130203813A1 (en) | 2011-05-04 | 2013-08-08 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
US20120283381A1 (en) | 2011-05-04 | 2012-11-08 | Ryuta Tamiya | Macroinitiator containing hydrophobic segment |
US9170349B2 (en) | 2011-05-04 | 2015-10-27 | Johnson & Johnson Vision Care, Inc. | Medical devices having homogeneous charge density and methods for making same |
JP5439551B2 (ja) | 2011-08-15 | 2014-03-12 | 一般財団法人川村理化学研究所 | ブロック共重合体の塗膜 |
IN2014DN09503A (ja) | 2012-05-25 | 2015-07-17 | Johnson & Johnson Vision Care | |
US9297929B2 (en) | 2012-05-25 | 2016-03-29 | Johnson & Johnson Vision Care, Inc. | Contact lenses comprising water soluble N-(2 hydroxyalkyl) (meth)acrylamide polymers or copolymers |
US9244196B2 (en) | 2012-05-25 | 2016-01-26 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
US10073192B2 (en) | 2012-05-25 | 2018-09-11 | Johnson & Johnson Vision Care, Inc. | Polymers and nanogel materials and methods for making and using the same |
CA2889891C (en) * | 2012-12-14 | 2017-10-24 | Novartis Ag | Amphiphilic siloxane-containing vinylic monomers and uses thereof |
GB201405066D0 (en) * | 2014-03-21 | 2014-05-07 | Scapa Uk Ltd | Wound dressing and compositions therefor |
CN104592532B (zh) * | 2014-12-18 | 2017-03-22 | 东华大学 | 一种两亲性共聚物网络及其制备方法 |
CN105504151A (zh) * | 2016-02-24 | 2016-04-20 | 湖北大学 | 一种高折射水凝胶型纳米复合材料的制备方法及应用 |
US20190160205A1 (en) * | 2016-07-28 | 2019-05-30 | Toray Industries, Inc. | Medical device and method of manufacturing medical device |
US10676575B2 (en) * | 2016-10-06 | 2020-06-09 | Johnson & Johnson Vision Care, Inc. | Tri-block prepolymers and their use in silicone hydrogels |
US10996491B2 (en) | 2018-03-23 | 2021-05-04 | Johnson & Johnson Vision Care, Inc. | Ink composition for cosmetic contact lenses |
US11891526B2 (en) | 2019-09-12 | 2024-02-06 | Johnson & Johnson Vision Care, Inc. | Ink composition for cosmetic contact lenses |
Family Cites Families (14)
Publication number | Priority date | Publication date | Assignee | Title |
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DE2831335A1 (de) * | 1978-07-17 | 1980-02-07 | Basf Ag | Herstellung modifizierter polymerisate des poly-n-vinylpyrrolidons-2 und ihre verwendung zur herstellung von durch zwischenglieder unterbrochenen polymerisaten |
US5135297A (en) * | 1990-11-27 | 1992-08-04 | Bausch & Lomb Incorporated | Surface coating of polymer objects |
CA2115143C (en) * | 1991-08-19 | 2002-11-19 | Robert R. Gagne | Macromonomers having reactive end groups |
US5310779A (en) * | 1991-11-05 | 1994-05-10 | Bausch & Lomb Incorporated | UV curable crosslinking agents useful in copolymerization |
JPH083254A (ja) * | 1994-06-15 | 1996-01-09 | Showa Highpolymer Co Ltd | シリコーン系ブロック共重合体エマルジョンの製造方法 |
JP3518098B2 (ja) * | 1995-10-04 | 2004-04-12 | 東ソー株式会社 | シリコーン−ビニル系ブロック共重合体の製造方法 |
JPH11305172A (ja) * | 1998-04-16 | 1999-11-05 | Seiko Epson Corp | 含水性ソフトコンタクトレンズ |
JP2000053716A (ja) | 1998-08-05 | 2000-02-22 | Wako Pure Chem Ind Ltd | マクロアゾ化合物 |
JP4456231B2 (ja) * | 2000-05-30 | 2010-04-28 | 株式会社日本触媒 | ポリビニルラクタム変性物 |
US6555619B1 (en) * | 2000-06-29 | 2003-04-29 | The University Of Akron | Physically crosslinked amphiphilic networks, methods of preparation, and uses thereof |
US8101196B2 (en) * | 2001-06-26 | 2012-01-24 | Biointeractions, Ltd. | Polysaccharide biomaterials and methods of use thereof |
GB0207742D0 (en) * | 2002-04-03 | 2002-05-15 | Unilever Plc | Fabric care composition |
US20050181977A1 (en) * | 2003-11-10 | 2005-08-18 | Angiotech International Ag | Medical implants and anti-scarring agents |
US7247692B2 (en) * | 2004-09-30 | 2007-07-24 | Johnson & Johnson Vision Care, Inc. | Biomedical devices containing amphiphilic block copolymers |
-
2008
- 2008-03-13 AU AU2008224989A patent/AU2008224989B2/en not_active Ceased
- 2008-03-13 CA CA2681090A patent/CA2681090C/en not_active Expired - Fee Related
- 2008-03-13 EP EP08732116.2A patent/EP2132242B1/en active Active
- 2008-03-13 WO PCT/US2008/056825 patent/WO2008112874A1/en active Application Filing
- 2008-03-13 US US12/531,200 patent/US8153728B2/en not_active Expired - Fee Related
- 2008-03-13 CN CN2008800130987A patent/CN101663340B/zh not_active Expired - Fee Related
- 2008-03-13 CA CA2783363A patent/CA2783363A1/en not_active Abandoned
- 2008-03-13 JP JP2009553775A patent/JP5537954B2/ja not_active Expired - Fee Related
-
2011
- 2011-12-14 US US13/325,584 patent/US8344090B2/en not_active Expired - Fee Related
-
2012
- 2012-07-13 JP JP2012157818A patent/JP5526376B2/ja not_active Expired - Fee Related
Also Published As
Publication number | Publication date |
---|---|
JP2012246489A (ja) | 2012-12-13 |
AU2008224989B2 (en) | 2011-11-24 |
EP2132242A1 (en) | 2009-12-16 |
CA2681090C (en) | 2013-07-16 |
CN101663340B (zh) | 2011-11-30 |
CA2783363A1 (en) | 2008-09-18 |
CN101663340A (zh) | 2010-03-03 |
US8344090B2 (en) | 2013-01-01 |
JP5526376B2 (ja) | 2014-06-18 |
EP2132242B1 (en) | 2017-01-11 |
US20100099829A1 (en) | 2010-04-22 |
CA2681090A1 (en) | 2008-09-18 |
JP2010521561A (ja) | 2010-06-24 |
US20120083573A1 (en) | 2012-04-05 |
WO2008112874A1 (en) | 2008-09-18 |
US8153728B2 (en) | 2012-04-10 |
EP2132242A4 (en) | 2010-12-01 |
AU2008224989A1 (en) | 2008-09-18 |
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