RU2012149840A - Силикон-акриловый сополимер - Google Patents
Силикон-акриловый сополимер Download PDFInfo
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- RU2012149840A RU2012149840A RU2012149840/04A RU2012149840A RU2012149840A RU 2012149840 A RU2012149840 A RU 2012149840A RU 2012149840/04 A RU2012149840/04 A RU 2012149840/04A RU 2012149840 A RU2012149840 A RU 2012149840A RU 2012149840 A RU2012149840 A RU 2012149840A
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- Prior art keywords
- acrylic
- silicone
- meth
- functional group
- polymer
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- 229920006243 acrylic copolymer Polymers 0.000 title claims abstract 15
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract 15
- -1 siloxane functional group Chemical group 0.000 claims abstract 13
- 239000000203 mixture Substances 0.000 claims abstract 11
- 239000000178 monomer Substances 0.000 claims abstract 11
- 229920000058 polyacrylate Polymers 0.000 claims abstract 9
- 229920005573 silicon-containing polymer Polymers 0.000 claims abstract 9
- BLRPTPMANUNPDV-UHFFFAOYSA-N Silane Chemical compound [SiH4] BLRPTPMANUNPDV-UHFFFAOYSA-N 0.000 claims abstract 5
- 239000003054 catalyst Substances 0.000 claims abstract 5
- 229910000077 silane Inorganic materials 0.000 claims abstract 5
- 125000001424 substituent group Chemical group 0.000 claims abstract 5
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims abstract 4
- 238000006243 chemical reaction Methods 0.000 claims abstract 4
- 125000000524 functional group Chemical group 0.000 claims abstract 4
- 239000003999 initiator Substances 0.000 claims abstract 3
- 229920001296 polysiloxane Polymers 0.000 claims abstract 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims abstract 2
- 125000003545 alkoxy group Chemical group 0.000 claims abstract 2
- 125000005370 alkoxysilyl group Chemical group 0.000 claims abstract 2
- 239000007795 chemical reaction product Substances 0.000 claims abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract 2
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 claims 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 claims 3
- 239000002904 solvent Substances 0.000 claims 3
- WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 claims 2
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 claims 2
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims 2
- 239000000463 material Substances 0.000 claims 2
- 229920000728 polyester Polymers 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 244000043261 Hevea brasiliensis Species 0.000 claims 1
- 239000002253 acid Substances 0.000 claims 1
- 230000002378 acidificating effect Effects 0.000 claims 1
- 230000001070 adhesive effect Effects 0.000 claims 1
- 239000003963 antioxidant agent Substances 0.000 claims 1
- 230000003078 antioxidant effect Effects 0.000 claims 1
- 238000009835 boiling Methods 0.000 claims 1
- 239000003153 chemical reaction reagent Substances 0.000 claims 1
- 239000004927 clay Substances 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 238000000576 coating method Methods 0.000 claims 1
- 239000000945 filler Substances 0.000 claims 1
- 150000004795 grignard reagents Chemical class 0.000 claims 1
- 238000010438 heat treatment Methods 0.000 claims 1
- 239000003456 ion exchange resin Substances 0.000 claims 1
- 229920003303 ion-exchange polymer Polymers 0.000 claims 1
- 238000004519 manufacturing process Methods 0.000 claims 1
- 229940098779 methanesulfonic acid Drugs 0.000 claims 1
- 229920003052 natural elastomer Polymers 0.000 claims 1
- 229920001194 natural rubber Polymers 0.000 claims 1
- 150000002900 organolithium compounds Chemical class 0.000 claims 1
- 229920002635 polyurethane Polymers 0.000 claims 1
- 239000004814 polyurethane Substances 0.000 claims 1
- 238000010992 reflux Methods 0.000 claims 1
- 239000012945 sealing adhesive Substances 0.000 claims 1
- 239000003566 sealing material Substances 0.000 claims 1
- 229920002050 silicone resin Polymers 0.000 claims 1
- 238000006467 substitution reaction Methods 0.000 claims 1
- 229920003051 synthetic elastomer Polymers 0.000 claims 1
- 239000005061 synthetic rubber Substances 0.000 claims 1
- 239000004034 viscosity adjusting agent Substances 0.000 claims 1
- 125000005369 trialkoxysilyl group Chemical group 0.000 abstract 1
Classifications
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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
- C08G77/04—Polysiloxanes
- C08G77/38—Polysiloxanes modified by chemical after-treatment
-
- 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
- C08F283/00—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G
- C08F283/12—Macromolecular compounds obtained by polymerising monomers on to polymers provided for in subclass C08G on to polysiloxanes
-
- 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
- C08F290/00—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups
- C08F290/02—Macromolecular compounds obtained by polymerising monomers on to polymers modified by introduction of aliphatic unsaturated end or side groups on to polymers modified by introduction of unsaturated end groups
- C08F290/06—Polymers provided for in subclass C08G
-
- 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
- C08F299/00—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers
- C08F299/02—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates
- C08F299/08—Macromolecular compounds obtained by interreacting polymers involving only carbon-to-carbon unsaturated bond reactions, in the absence of non-macromolecular monomers from unsaturated polycondensates from polysiloxanes
-
- 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
- C08G77/20—Polysiloxanes containing silicon bound to unsaturated aliphatic groups
-
- 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
- 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
-
- 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
- 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
-
- 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
- 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
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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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J183/00—Adhesives 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; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K3/00—Materials not provided for elsewhere
- C09K3/10—Materials in mouldable or extrudable form for sealing or packing joints or covers
- C09K3/1006—Materials in mouldable or extrudable form for sealing or packing joints or covers characterised by the chemical nature of one of its constituents
- C09K3/1018—Macromolecular compounds having one or more carbon-to-silicon linkages
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- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Wood Science & Technology (AREA)
- General Chemical & Material Sciences (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Material Composition (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Graft Or Block Polymers (AREA)
- Paints Or Removers (AREA)
Abstract
1. Силикон-акриловый сополимер, содержащий силиконовый полимер и акриловый полимер, которые являются ковалентно связанными через связь -Si-O-, где отношение силиконового полимера и акрилового мономера составляет от 50:1 до 1:50 и акриловый полимер содержит, по меньшей мере, одну силановую или силоксановую функциональную группу.2. Силикон-акриловый сополимер, содержащий продукт реакции:(a) силиконового полимера;(b) (i) смеси акриловых мономеров и радикального инициатора, где, по меньшей мере, один акриловый мономер содержит силан-(мет)акриловый мономер и/или силоксан-(мет)акриловый макромер; или (ii) акрилового полимера, который содержит силановую или силоксановую функциональную группу; и(c) катализатора реакции обмена заместителями;где отношение (a) к (b) составляет от 50:1 до 1:50.3. Силикон-акриловый сополимер по любому из пп.1 или 2, где силиконовый полимер представляет собой полисилоксан, дважды замещенный органическими заместителями, который имеет присоединенную концевую гидроксильную функциональную группу, алкоксильную функциональную группу, гидридную функциональную группу, винильную функциональную группу или их смесь.4. Силикон-акриловый сополимер по п.2, где силан-(мет)акриловый мономер является выбранным из группы, состоящей из диалкоксисилил-(мет)акрилатов, триалкоксилсилил-(мет)акрилатов и их смесей; и где силоксан-(мет)акриловый макромер представляет собой полидиметилсилоксан-моно(мет)акрилат.5. Силикон-акриловый сополимер по любому из пп.1 или 2, где два конца цепи акрилового полимера содержат присоединенную алкоксисилильную функциональную группу, которая является выбранной из триметоксилсилильной группы, диме�
Claims (10)
1. Силикон-акриловый сополимер, содержащий силиконовый полимер и акриловый полимер, которые являются ковалентно связанными через связь -Si-O-, где отношение силиконового полимера и акрилового мономера составляет от 50:1 до 1:50 и акриловый полимер содержит, по меньшей мере, одну силановую или силоксановую функциональную группу.
2. Силикон-акриловый сополимер, содержащий продукт реакции:
(a) силиконового полимера;
(b) (i) смеси акриловых мономеров и радикального инициатора, где, по меньшей мере, один акриловый мономер содержит силан-(мет)акриловый мономер и/или силоксан-(мет)акриловый макромер; или (ii) акрилового полимера, который содержит силановую или силоксановую функциональную группу; и
(c) катализатора реакции обмена заместителями;
где отношение (a) к (b) составляет от 50:1 до 1:50.
3. Силикон-акриловый сополимер по любому из пп.1 или 2, где силиконовый полимер представляет собой полисилоксан, дважды замещенный органическими заместителями, который имеет присоединенную концевую гидроксильную функциональную группу, алкоксильную функциональную группу, гидридную функциональную группу, винильную функциональную группу или их смесь.
4. Силикон-акриловый сополимер по п.2, где силан-(мет)акриловый мономер является выбранным из группы, состоящей из диалкоксисилил-(мет)акрилатов, триалкоксилсилил-(мет)акрилатов и их смесей; и где силоксан-(мет)акриловый макромер представляет собой полидиметилсилоксан-моно(мет)акрилат.
5. Силикон-акриловый сополимер по любому из пп.1 или 2, где два конца цепи акрилового полимера содержат присоединенную алкоксисилильную функциональную группу, которая является выбранной из триметоксилсилильной группы, диметоксиметилсилильной группы, триэтоксилсилильной группы, диэтоксиметилсилильной группы или их смесей.
6. Силикон-акриловый сополимер по п.5, где катализатор реакции обмена заместителями имеет значение рКа, равное или меньшее -6 или равное или большее 15, и данный катализатор реакции обмена заместителями выбран из группы, включающий в себя KOH, NaOH, LiOH, реагенты, представляющие собой литийорганические соединения, реактивы Гриньяра, метансульфоновую кислоту, серную кислоту, кислую глину, кислотные ионообменные смолы и их смеси.
7. Композиция, содержащая силикон-акриловый сополимер, по пп.1-6, дополнительно содержащая вещество, повышающее клейкость, силиконовую смолу, солюбилизаторы, сложный полиэфир, простой полиэфир, полиуретан, натуральный каучук, синтетический каучук, антиоксидант, модификатор вязкости, наполнитель или их смесь.
8. Изделие, содержащее силикон-акриловый сополимер, по пп.1-7.
9. Изделие по п.8, которое представляет собой кроющий материал, уплотнительный материал или адгезивный материал.
10. Способ получения силикон-акрилового сополимера по п.2, включающий в себя комбинирование силиконового полимера, смесей акриловых мономеров с радикальным инициатором или акриловымполимером, катализатора реакции обмена заместителями, растворителя и нагревание, и кипячение с обратным холодильником при температуре кипения растворителя.
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32714110P | 2010-04-23 | 2010-04-23 | |
| US61/327,141 | 2010-04-23 | ||
| PCT/US2011/032609 WO2011133408A2 (en) | 2010-04-23 | 2011-04-15 | Silicone-acrylic copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| RU2012149840A true RU2012149840A (ru) | 2014-05-27 |
| RU2570574C2 RU2570574C2 (ru) | 2015-12-10 |
Family
ID=44834733
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| RU2012149840/04A RU2570574C2 (ru) | 2010-04-23 | 2011-04-15 | Силикон-акриловый сополимер |
Country Status (8)
| Country | Link |
|---|---|
| US (3) | US8664329B2 (ru) |
| EP (1) | EP2561008B1 (ru) |
| JP (1) | JP5826826B2 (ru) |
| KR (2) | KR101535847B1 (ru) |
| CN (1) | CN102947370B (ru) |
| BR (1) | BR112012027110B1 (ru) |
| RU (1) | RU2570574C2 (ru) |
| WO (1) | WO2011133408A2 (ru) |
Families Citing this family (48)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP5609923B2 (ja) * | 2012-06-12 | 2014-10-22 | コニカミノルタ株式会社 | 中間転写体及びそれを有する画像形成装置 |
| CN103045082B (zh) * | 2012-12-16 | 2016-06-29 | 青岛文创科技有限公司 | 一种复合有机硅树脂及其制备方法 |
| US10894904B2 (en) | 2013-04-15 | 2021-01-19 | Nitto Denko Corporation | Pressure-sensitive adhesive sheet and pressure sensitive adhesive composition |
| JP6223836B2 (ja) * | 2013-04-15 | 2017-11-01 | 日東電工株式会社 | 粘着剤組成物および粘着シート |
| EP3004190B1 (en) | 2013-05-30 | 2020-02-12 | Dow Global Technologies LLC | Wood coating composition |
| CN105273667B (zh) * | 2014-06-06 | 2019-02-12 | 上海晶华胶粘新材料股份有限公司 | 耐高温硅丙压敏胶粘剂及其制备方法 |
| CN104263314B (zh) * | 2014-09-23 | 2016-03-02 | 佛山市日丰企业有限公司 | 一种改性硅酮弹性密封胶及其制备方法 |
| WO2016048302A1 (en) | 2014-09-24 | 2016-03-31 | Halliburton Energy Services, Inc. | Silane additives for improved sand strength and conductivity in fracturing applications |
| US10020185B2 (en) | 2014-10-07 | 2018-07-10 | Samsung Sdi Co., Ltd. | Composition for forming silica layer, silica layer, and electronic device |
| EP3034573A1 (en) | 2014-12-16 | 2016-06-22 | ALLNEX AUSTRIA GmbH | Flow modifier for coating compositions |
| KR101837971B1 (ko) | 2014-12-19 | 2018-03-13 | 삼성에스디아이 주식회사 | 실리카계 막 형성용 조성물, 실리카계 막, 및 전자 디바이스 |
| KR101833800B1 (ko) | 2014-12-19 | 2018-03-02 | 삼성에스디아이 주식회사 | 실리카계 막 형성용 조성물, 실리카계 막의 제조방법 및 상기 실리카계 막을 포함하는 전자 소자 |
| CN104531048B (zh) * | 2014-12-30 | 2016-08-24 | 南京信息工程大学 | 一种有机导电胶合剂及其制备方法 |
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-
2011
- 2011-04-15 KR KR1020127029107A patent/KR101535847B1/ko active Active
- 2011-04-15 BR BR112012027110-5A patent/BR112012027110B1/pt not_active IP Right Cessation
- 2011-04-15 WO PCT/US2011/032609 patent/WO2011133408A2/en not_active Ceased
- 2011-04-15 RU RU2012149840/04A patent/RU2570574C2/ru not_active IP Right Cessation
- 2011-04-15 JP JP2013506189A patent/JP5826826B2/ja active Active
- 2011-04-15 CN CN201180030690.XA patent/CN102947370B/zh active Active
- 2011-04-15 EP EP11772467.4A patent/EP2561008B1/en active Active
- 2011-04-15 KR KR1020147032339A patent/KR101644349B1/ko active Active
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- 2014-01-15 US US14/155,452 patent/US8962748B2/en active Active
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| RU2570574C2 (ru) | 2015-12-10 |
| US20140128539A1 (en) | 2014-05-08 |
| US20150119536A1 (en) | 2015-04-30 |
| KR101644349B1 (ko) | 2016-08-01 |
| EP2561008A2 (en) | 2013-02-27 |
| WO2011133408A2 (en) | 2011-10-27 |
| WO2011133408A4 (en) | 2012-04-12 |
| CN102947370B (zh) | 2016-05-11 |
| US20130012653A1 (en) | 2013-01-10 |
| EP2561008A4 (en) | 2013-11-06 |
| JP5826826B2 (ja) | 2015-12-02 |
| BR112012027110A2 (pt) | 2016-07-26 |
| KR20140141724A (ko) | 2014-12-10 |
| BR112012027110B1 (pt) | 2020-05-12 |
| KR101535847B1 (ko) | 2015-07-13 |
| KR20130064066A (ko) | 2013-06-17 |
| JP2013525543A (ja) | 2013-06-20 |
| US8664329B2 (en) | 2014-03-04 |
| EP2561008B1 (en) | 2018-02-28 |
| CN102947370A (zh) | 2013-02-27 |
| US8962748B2 (en) | 2015-02-24 |
| WO2011133408A3 (en) | 2012-02-16 |
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