JP5702603B2 - 重合可能な官能基を含むポリビニルアミドポリマー - Google Patents
重合可能な官能基を含むポリビニルアミドポリマー Download PDFInfo
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- C08F220/32—Esters containing oxygen in addition to the carboxy oxygen containing epoxy radicals
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- C08F220/52—Amides or imides
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- C08F220/54—Amides, e.g. N,N-dimethylacrylamide or N-isopropylacrylamide
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Description
本出願は、2007年8月15日付け出願の米国仮出願第60/955,947号及び2008年6月18日付け出願の米国の仮出願第61/073,535号の優先権を主張し、その内容を参照することによって本出願の開示において組込む。
Q−R−E (式I)
[式Iにおいて、Qはオキシラン、オキセタン、アジリジン、オキサゾリン又はベンゾオキサジンであり、Eは炭素−炭素二重結合を含む重合可能な官能基であり、Rはヘテロ原子を含むか又は含まない脂肪族及び/又は芳香族成分である。]遊離の炭素−炭素二重結合及び/又は遊離のイオン重合可能な官能基をもたらすポリマーに当該モノマーを組み込むことができる。
a)少なくとも一つのN−ビニルアミドモノマー、及び
b)下記式IIIの構造を有する少なくとも一つの2官能モノマーを含む。
Q−R−E (式III)
[式IIIにおいて、Qはオキシラン、オキセタン、アジリジン、オキサゾリン又はベンゾオキサジンであり、Eは炭素−炭素二重結合を含む重合可能な官能基であり、Rはヘテロ原子を含むか又は含まない脂肪族及び/又は芳香族成分である。]遊離の炭素−炭素二重結合及び/又は遊離のイオン重合可能な官能基をもたらすポリマーに当該モノマーを組み込むことができる。
1.0リットルの三口丸底フラスコに錨型撹拌機、熱電対、添加用漏斗及び窒素パージラインを設置した。フラスコに80gの脱イオン水、27gのエタノールSDA40B、80gのVCL及びエタノールを投入した。該システムを3回窒素でパージし、反応の間システムを窒素で覆った。フラスコを80℃に加熱し、その間に添加用漏斗で15gのDMAPMAと、5gのHEMAとを加え、107.5gの脱イオン水と混合した。80℃にて、まず開始剤を1.1gのエタノールSDA40Bと混合することにより、0.208gのVazo−67注入液をフラスコに添加した。開始剤の添加後、DMAPMA/HEMA/水を滴状で連続的に添加し始めた。30分及び60分の間隔でさらに2当量以上の開始剤を添加した。DMAPMA/HEMA/水の添加が完了した後、88gの希釈用脱イオン水を添加した。最終pHを塩酸で調整して6.5〜7.5の範囲にすべきである。pH調整後、エタノールを真空下で留去し、脱イオン水と置換する。エタノール除去が完了した後、3gのGMAを混合物に添加し、60℃で1時間加熱した。反応生成物の代表的な構造を以下式IVに示す。
300mlのガラス製フラスコに頭上式撹拌機及び熱電対を設置した。該フラスコに10gのVP/AA/ラウリルメタクリレート3元重合体(Styleze2000)及び90gの水とエタノール50/50混合物を投入した。pHを水酸化アンモニウムで6〜7に調整した。該システムを3回窒素でパージし、反応の間システムを窒素で覆った。フラスコを60℃に加熱した。該温度に達すると、1.2gのGMAを滴下した。混合物を60℃で1時間加熱した。ポリマー溶液を室温へ冷却し、水とエタノールの蒸発ができるようにガラス製トレイ中に1晩置いた。反応生成物の代表的な構造を以下式Vに示す、ここでx+y+z+a=100である。
2種類のモノマー/溶媒混合物を調製した。ヒール(heal)は10gのVP、4gのGMA及び80gのアセトンの混合物である。完全に混合した。仕込み(feed)1は30gのVP、10gのVA、4gのGMA及び124gのアセトンの混合物である。完全に混合した。磁石式撹拌機、添加用漏斗及び冷却凝縮器を備えた500mlのガラス製反応容器にヒールと5gの仕込み1を投入した。残りの仕込み1を添加用漏斗に投入した。窒素を連続的に流して反応容器のパージを開始した。加熱を開始しておよそ57℃で還流した。もう一つ別の容器において0.40gの2,2‘−アゾビス(2,4−ジメチルペンタンニトリル)(VAZO 52)及び4gのアセトンの混合物(仕込み2)を調製した。反応フラスコが還流温度に到達した際に、反応容器に1gの仕込み2を投入した。次いで、仕込み1の添加を開始し、3時間にわたり連続的に滴下した。1時間後に1gの仕込み2を反応容器に投入した。次の2時間この仕込み2の添加を繰り返した。仕込み2の添加を完了して1時間経過させ、もう1つの開始剤、0.1gのt−ブチルペルオキシピバレート(Lupersol 11)を反応容器に投入した。反応容器をさらに1時間加熱還流し、続いてさらに0.2gのLupersol 11を添加した。開始剤の添加中追加のアセトンを添加してあらゆる揮発分を置換したことを注記する。さらなる1時間の保持終了時に、反応容器を室温まで冷却した。当該反応の代表的な構造を以下式VIに示す、ここでx+y+z=100である。
実施例4〜6は本発明の特定の実施態様の先駆的な実施例である。
1.0リットルの三口丸底フラスコに錨型撹拌機、熱電対、添加用漏斗、冷却凝縮器及び窒素パージラインを設置した。このフラスコに140gのアセトン及び40gのVCLを投入した。該システムを3回窒素でパージし、次いで反応中システムを窒素で覆った。フラスコを加熱しておよそ57℃で還流し、この間に添加用漏斗で20gのVA、5gのGMAを投入し、100gのアセトンと混合した。還流時に、0.208g注入のアゾビスイソブチロニトリルを1.1gのアセトンとまず混合することにより、該開始剤をフラスコに加えた。開始剤の添加後、VAの連続滴下を始めた。さらに5回当量の開始剤を60分の間隔で添加した。生成物を室温まで冷却した。
120gのMANを455gのトルエンに70℃で溶解した。この溶液を添加用漏斗内に静置した。別の添加用漏斗において、30gのGMAを50gのトルエンに加えた。170gのVPと335gのトルエンを反応容器に投入した。該システムを窒素でパージした。反応容器の温度を55℃に昇温し、VAZO開始剤5gを添加した。次いで、MANとGMAを滴下を開始し、2.5時間後に完了した。該システムをさらに1時間撹拌した。沈殿したポリマーをろ過し、ヘプタン中で再度スラリー化し、再度ろ過した。ポリマーを1時間風燥し、次いで35℃で真空乾燥した。
頭上式撹拌機を備えた500mlの丸底フラスコ中で、50gのVP/DMAEMAポリマー(mwおよそ80,000〜150,000g/mol)の粉体を力強く撹拌されている200gの脱イオン水に加えた。粉体が完全に溶媒和するまで溶液を混合した。反応容器を60℃に加熱した。このポリマー溶液に2.5gのGMAを滴下した。混合物を1時間加熱し、次いで室温まで冷却した。
水性UV硬化性塗膜
100%固体のUV硬化性塗膜
膜用の親水性添加剤
米国特許第7,300,022号 B2の教示(その内容をここに参照して援用する)を平坦なシート状膜の製造用案内物として利用して、PVP/VA/GMAを用いてドープ溶液を調製した。
Claims (1)
- a)N−ビニルカプロラクタムと、b)グリシジルメタクリレートと、c)酢酸ビニルとを、8:1:4の重量比率で含む反応混合物中におけるラジカル重合により製造される、ポリマー。
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US95594707P | 2007-08-15 | 2007-08-15 | |
US60/955,947 | 2007-08-15 | ||
US7353508P | 2008-06-18 | 2008-06-18 | |
US61/073,535 | 2008-06-18 | ||
PCT/US2008/073344 WO2009023843A1 (en) | 2007-08-15 | 2008-08-15 | Polyvinylamide polymers containing polymerizable functionalities |
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EP (1) | EP2201051A1 (ja) |
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US20090162359A1 (en) | 2007-12-21 | 2009-06-25 | Christian Klein | Bivalent, bispecific antibodies |
WO2010111607A1 (en) * | 2009-03-27 | 2010-09-30 | Isp Investments Inc. | Premixes suitable for the production of membrane materials |
RU2598248C2 (ru) | 2009-04-02 | 2016-09-20 | Роше Гликарт Аг | Полиспецифичные антитела, включающие антитела полной длины и одноцепочечные фрагменты fab |
EP2417156B1 (en) | 2009-04-07 | 2015-02-11 | Roche Glycart AG | Trivalent, bispecific antibodies |
US9676845B2 (en) | 2009-06-16 | 2017-06-13 | Hoffmann-La Roche, Inc. | Bispecific antigen binding proteins |
RU2573915C2 (ru) | 2009-09-16 | 2016-01-27 | Дженентек, Инк. | Содержащие суперспираль и/или привязку белковые комплексы и их применение |
BR112012012348A2 (pt) * | 2009-11-23 | 2016-04-26 | Isp Investments Inc | solução reativa de polímeros polimerizáveis compreendedo funcionalidades reativas polimerizáveis, processos e composições da mesma |
WO2011079209A1 (en) * | 2009-12-22 | 2011-06-30 | Isp Investments Inc. | Polymerizable lactamic copolymers suitable for the formation of coatings on microencapsulated particles |
TW201138821A (en) | 2010-03-26 | 2011-11-16 | Roche Glycart Ag | Bispecific antibodies |
WO2012025530A1 (en) | 2010-08-24 | 2012-03-01 | F. Hoffmann-La Roche Ag | Bispecific antibodies comprising a disulfide stabilized - fv fragment |
EP2655427B1 (en) | 2010-12-22 | 2019-03-27 | Dentsply DeTrey GmbH | Polymer for a glass ionomer cement |
JP5766296B2 (ja) | 2010-12-23 | 2015-08-19 | エフ.ホフマン−ラ ロシュ アーゲーF. Hoffmann−La Roche Aktiengesellschaft | ポリペプチド−ポリヌクレオチド複合体、およびエフェクター成分の標的化された送達におけるその使用 |
EP2681239B8 (en) | 2011-02-28 | 2015-09-09 | F. Hoffmann-La Roche AG | Antigen binding proteins |
MX342034B (es) | 2011-02-28 | 2016-09-12 | Hoffmann La Roche | Proteinas monovalentes que se unen a antigenos. |
US9464151B2 (en) | 2011-04-28 | 2016-10-11 | Isp Investments Llc | Lactamic polymer containing an acetoacetate moiety |
GB201112389D0 (en) | 2011-07-19 | 2011-08-31 | Fujifilm Mfg Europe Bv | Curable compositions and membranes |
DE102011082042A1 (de) | 2011-09-02 | 2013-03-07 | Beiersdorf Ag | Kationische Terropolymere auf Basis von (Meth)acryloylmorpholin |
MX2014009565A (es) | 2012-02-10 | 2014-11-10 | Genentech Inc | Anticuerpos monocatenarios y otros heteromultimeros. |
MX2014014804A (es) | 2012-06-27 | 2015-02-12 | Hoffmann La Roche | Metodo para la elaboracion de conjugados de la region fc de anticuerpos que comprenden por lo menos una entidad de union que se une especificamente a un objetivo y usos del mismo. |
MX354862B (es) | 2012-06-27 | 2018-03-23 | Hoffmann La Roche | Método para la producción de entidades dirigidas altamente selectivas hechas a la medida y biespecíficas que contienen dos entidades de unión diferentes. |
EP3055329B1 (en) | 2013-10-11 | 2018-06-13 | F. Hoffmann-La Roche AG | Multispecific domain exchanged common variable light chain antibodies |
WO2016087416A1 (en) | 2014-12-03 | 2016-06-09 | F. Hoffmann-La Roche Ag | Multispecific antibodies |
GB2536410A (en) * | 2015-03-06 | 2016-09-21 | The Queen's Univ Of Belfast | Coating composition and uses thereof |
CN109233664A (zh) * | 2018-06-12 | 2019-01-18 | 哈尔滨工业大学无锡新材料研究院 | 一种uv固化型胶粘剂、其制备方法及应用 |
TWI724765B (zh) * | 2020-01-21 | 2021-04-11 | 達興材料股份有限公司 | 可雷射離型的組成物、其積層體和雷射離型方法 |
CN113603826B (zh) * | 2021-06-30 | 2022-06-28 | 浙江大学 | 一种丙烯酰基甘氨酰胺-苯硼酸基糖敏微针的制备方法 |
Family Cites Families (55)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3787380A (en) * | 1971-10-05 | 1974-01-22 | Union Optics Corp | Polymers of n-vinyl or n-allyl hetero-cyclic compounds with monoethyl-enically unsaturated esters and gly-cidyl esters |
US3862091A (en) * | 1972-03-07 | 1975-01-21 | Gaf Corp | Quaternized n-vinyl lactam polymeric compositions and mannich adducts thereof |
FR2239486A1 (en) * | 1973-07-10 | 1975-02-28 | Union Optics Corp | N-vinyl or n-allyl polymers - with unsatd esters and glycidyl esters forming hydrogels |
US4070348A (en) | 1973-07-25 | 1978-01-24 | Rohm Gmbh | Water-swellable, bead copolymer |
DE2444108C2 (de) | 1974-09-14 | 1978-01-19 | Hoechst Ag | Wasserbasische tonspuelung fuer tiefbohrungen und verwendung eines mischpolymerisats fuer solche spuelungen |
US3997306A (en) | 1975-03-31 | 1976-12-14 | Ppg Industries, Inc. | Glass fiber sizing composition for the reinforcement of resin matrices and method of using same |
US4070532A (en) | 1975-05-23 | 1978-01-24 | E. I. Du Pont De Nemours And Company | Ethylene carbon monoxide copolymers containing epoxy side groups |
JPS601335B2 (ja) * | 1977-05-26 | 1985-01-14 | 東レ株式会社 | 医用高分子材料の製造方法 |
FR2477058A1 (fr) * | 1980-02-28 | 1981-09-04 | Medicornea Sa | Procede de fabrication par moulage de lentilles de contact, et lentilles obtenues |
JPS57103649A (en) | 1980-12-18 | 1982-06-28 | Asahi Chemical Ind | Sterilized gamma-globulin fixing column |
US4737544A (en) | 1982-08-12 | 1988-04-12 | Biospecific Technologies, Inc. | Biospecific polymers |
DE3381105D1 (de) | 1982-08-12 | 1990-02-22 | Kanegafuchi Chemical Ind | Aktivierung biovertraeglicher terpolymere mit biologischen stoffen, deren anzubindende komplemente pathologische effektoren sind. |
DE3619129A1 (de) * | 1986-06-06 | 1987-12-10 | Basf Ag | Lichtempfindliches aufzeichnungselement |
US4812541A (en) * | 1987-12-23 | 1989-03-14 | Avery International Corporation | High performance pressure-sensitive adhesive polymers |
JP2709710B2 (ja) * | 1988-01-29 | 1998-02-04 | 日東化学工業株式会社 | ラジカル硬化性水溶性重合体 |
DE3838031A1 (de) | 1988-11-09 | 1990-05-10 | Basf Ag | Neue copolymerisate und ihre verwendung als hilfsmittel und/oder zusatzstoff in formulierungen zur herstellung von polyisocyanat-polyadditionsprodukten |
DE3838030A1 (de) * | 1988-11-09 | 1990-05-10 | Basf Ag | Neue copolymerisate und ihre verwendung als hilfsmittel und/oder zusatzstoff in formulierungen zur herstellung von polyisocyanat-polyadditionsprodukten |
US4989607A (en) | 1989-03-30 | 1991-02-05 | Preston Keusch | Highly conductive non-stringy adhesive hydrophilic gels and medical electrode assemblies manufactured therefrom |
US5159360A (en) | 1990-07-17 | 1992-10-27 | Kingston Technologies, Inc. | Contact lens with pre-determined useful life |
US5283305A (en) * | 1992-10-26 | 1994-02-01 | Isp Investments Inc. | Method of making crosslinked PVP |
US5712356A (en) * | 1993-11-26 | 1998-01-27 | Ciba Vision Corporation | Cross-linkable copolymers and hydrogels |
AU672159B2 (en) * | 1994-06-14 | 1996-09-19 | National Starch And Chemical Investment Holding Corporation | High performance PVOH stabilised EVA adhesives |
JP3661245B2 (ja) * | 1994-11-11 | 2005-06-15 | 大日本インキ化学工業株式会社 | 光重合性樹脂組成物 |
JP3851973B2 (ja) * | 1996-03-12 | 2006-11-29 | 大日本インキ化学工業株式会社 | 樹脂組成物の製造方法 |
GB9816826D0 (en) * | 1998-07-31 | 1998-09-30 | First Water Ltd | Bioadhesive compositions |
US5684105A (en) | 1996-07-23 | 1997-11-04 | Isp Investments Inc. | Process for providing homogeneous copolymers of vinylpyrrolidone and 3-dimethylaminopropyl methacrylamide (DMAPMA) which form clear aqueous solutions having high cloud points |
EP0947350B1 (en) | 1998-03-31 | 2003-06-04 | Oji Paper Co., Ltd. | Ink jet recording material |
JP3573964B2 (ja) | 1998-06-17 | 2004-10-06 | 三洋電機株式会社 | アルカリ電池用水素吸蔵合金電極及びアルカリ蓄電池用水素吸蔵合金電極の製造方法 |
US6649722B2 (en) * | 1999-12-10 | 2003-11-18 | Novartis Ag | Contact lens |
JP2002050022A (ja) * | 2000-05-25 | 2002-02-15 | Fuji Photo Film Co Ltd | 磁気記録媒体 |
US6451952B2 (en) | 2000-05-26 | 2002-09-17 | Nippon Shokubai Co., Ltd. | Production process for allyl ether-based polymer |
US20020048632A1 (en) | 2000-08-24 | 2002-04-25 | Smalley Richard E. | Polymer-wrapped single wall carbon nanotubes |
AUPR143400A0 (en) | 2000-11-13 | 2000-12-07 | Usf Filtration And Separations Group Inc. | Modified membranes |
US6465587B1 (en) | 2000-12-08 | 2002-10-15 | Hercules Incorporated | Polymeric fluid loss additives and method of use thereof |
US6639016B2 (en) | 2000-12-31 | 2003-10-28 | Basf Corporation | Method of making a graft polymer |
US6686425B2 (en) | 2001-06-08 | 2004-02-03 | Adhesives Research, Inc. | High Tg acrylic polymer and epoxy-containing blend therefor as pressure sensitive adhesive |
JP4684498B2 (ja) * | 2001-09-05 | 2011-05-18 | 大阪有機化学工業株式会社 | 化粧料用基剤およびそれからなる化粧料 |
US7008979B2 (en) | 2002-04-30 | 2006-03-07 | Hydromer, Inc. | Coating composition for multiple hydrophilic applications |
US7199249B2 (en) | 2002-07-03 | 2007-04-03 | Henkel Corporation | Free radically polymerizable coupling agents |
US6706835B2 (en) | 2002-07-19 | 2004-03-16 | National Starch And Chemical Investment Holding Corporation | Curable compositions containing thiazole functionality |
US6716992B2 (en) | 2002-07-22 | 2004-04-06 | National Starch And Chemical Investment Holding Corporation | Cycloaliphatic epoxy compounds containing styrenic, cinnamyl, or maleimide functionality |
DE10254432A1 (de) * | 2002-11-21 | 2004-06-03 | Süd-Chemie AG | LCST-Polymere |
US6753434B1 (en) | 2003-05-06 | 2004-06-22 | National Starch And Chemical Investment Holding Corporation | Oxetane compounds containing cinnamyl functionality |
JP2005029774A (ja) * | 2003-06-19 | 2005-02-03 | Nippon Shokubai Co Ltd | 活性エネルギー線硬化用組成物 |
DE10343900A1 (de) | 2003-09-19 | 2005-04-21 | Basf Ag | Verwendung von N-Vinyllactam enthaltenden Copolymeren zur Herstellung von funktionalisierten Membranen |
WO2005076074A2 (en) | 2004-02-02 | 2005-08-18 | Ciba Specialty Chemicals Holding Inc. | Functionalized photoinitiators |
JP2005290209A (ja) * | 2004-03-31 | 2005-10-20 | Nippon Shokubai Co Ltd | 硬化用組成物 |
US20060088675A1 (en) | 2004-10-25 | 2006-04-27 | Hladik Molly I | Radiation curable inkjet coatings for media and systems for processing the media |
US20070049651A1 (en) | 2005-08-23 | 2007-03-01 | Fuji Photo Film Co., Ltd. | Curable composition, ink composition, inkjet recording method, printed material, method of producing planographic printing plate, planographic printing plate, and oxcetane compound |
US20070212556A1 (en) | 2006-03-07 | 2007-09-13 | Musa Osama M | Curable materials containing siloxane |
US7837318B2 (en) | 2007-03-16 | 2010-11-23 | Hewlett-Packard Development Company, L.P. | Photo-curable ink-jet ink compositions, systems, and methods |
US8242224B2 (en) * | 2007-08-15 | 2012-08-14 | Isp Investments Inc. | Polyvinylamide polymers containing polymerizable functionalities |
WO2010111607A1 (en) * | 2009-03-27 | 2010-09-30 | Isp Investments Inc. | Premixes suitable for the production of membrane materials |
BR112012012348A2 (pt) * | 2009-11-23 | 2016-04-26 | Isp Investments Inc | solução reativa de polímeros polimerizáveis compreendedo funcionalidades reativas polimerizáveis, processos e composições da mesma |
US9290721B2 (en) * | 2010-12-09 | 2016-03-22 | Isp Investments Inc. | Visually perceivable image-forming dye scavenging article |
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EP2201051A1 (en) | 2010-06-30 |
WO2009023843A1 (en) | 2009-02-19 |
JP2010536960A (ja) | 2010-12-02 |
JP5993467B2 (ja) | 2016-09-14 |
US20110245409A1 (en) | 2011-10-06 |
AU2008286759B2 (en) | 2014-05-08 |
US10273324B2 (en) | 2019-04-30 |
US20160280826A1 (en) | 2016-09-29 |
JP2015120922A (ja) | 2015-07-02 |
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