JPS617315A - シアノエチルアクリレート／アクリル酸共重合体およびその製法 - Google Patents
シアノエチルアクリレート／アクリル酸共重合体およびその製法Info
- Publication number
- JPS617315A JPS617315A JP60116324A JP11632485A JPS617315A JP S617315 A JPS617315 A JP S617315A JP 60116324 A JP60116324 A JP 60116324A JP 11632485 A JP11632485 A JP 11632485A JP S617315 A JPS617315 A JP S617315A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- cyanoethyl acrylate
- acrylate
- acid copolymer
- polymer
- 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.)
- Granted
Links
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 title claims description 35
- 229920002126 Acrylic acid copolymer Polymers 0.000 title claims description 19
- 238000004519 manufacturing process Methods 0.000 title claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 34
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 claims description 27
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 22
- 239000000758 substrate Substances 0.000 claims description 19
- 229920000642 polymer Polymers 0.000 claims description 15
- 239000002904 solvent Substances 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 12
- 239000003431 cross linking reagent Substances 0.000 claims description 11
- 150000003254 radicals Chemical class 0.000 claims description 9
- 229910052751 metal Inorganic materials 0.000 claims description 7
- 239000002184 metal Substances 0.000 claims description 7
- 229920001897 terpolymer Polymers 0.000 claims description 7
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 claims description 6
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 6
- 239000011247 coating layer Substances 0.000 claims description 6
- 239000003999 initiator Substances 0.000 claims description 6
- 238000000034 method Methods 0.000 claims description 6
- 229910003437 indium oxide Inorganic materials 0.000 claims description 5
- PJXISJQVUVHSOJ-UHFFFAOYSA-N indium(iii) oxide Chemical group [O-2].[O-2].[O-2].[In+3].[In+3] PJXISJQVUVHSOJ-UHFFFAOYSA-N 0.000 claims description 5
- 229920000620 organic polymer Polymers 0.000 claims description 5
- 239000004593 Epoxy Substances 0.000 claims description 4
- 239000000178 monomer Substances 0.000 claims description 4
- 239000000126 substance Substances 0.000 claims description 4
- 150000002118 epoxides Chemical class 0.000 claims description 3
- 238000010438 heat treatment Methods 0.000 claims description 3
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical group N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims description 2
- 238000000576 coating method Methods 0.000 claims description 2
- VDFVNEFVBPFDSB-UHFFFAOYSA-N 1,3-dioxane Chemical compound C1COCOC1 VDFVNEFVBPFDSB-UHFFFAOYSA-N 0.000 claims 2
- 239000010410 layer Substances 0.000 claims 2
- 239000002954 polymerization reaction product Substances 0.000 claims 2
- 239000000047 product Substances 0.000 claims 2
- 239000004971 Cross linker Substances 0.000 claims 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 claims 1
- 239000011248 coating agent Substances 0.000 claims 1
- 229920006037 cross link polymer Polymers 0.000 claims 1
- 125000002243 cyclohexanonyl group Chemical group *C1(*)C(=O)C(*)(*)C(*)(*)C(*)(*)C1(*)* 0.000 claims 1
- 238000002360 preparation method Methods 0.000 claims 1
- 238000007348 radical reaction Methods 0.000 claims 1
- 238000006243 chemical reaction Methods 0.000 description 12
- 238000006116 polymerization reaction Methods 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 5
- 239000010408 film Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical group CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 239000012975 dibutyltin dilaurate Substances 0.000 description 3
- 230000000977 initiatory effect Effects 0.000 description 2
- 229910044991 metal oxide Inorganic materials 0.000 description 2
- 150000004706 metal oxides Chemical class 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 229920000058 polyacrylate Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- -1 Alicyclic epoxide Chemical class 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 229920000800 acrylic rubber Polymers 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- PCHJSUWPFVWCPO-UHFFFAOYSA-N gold Chemical compound [Au] PCHJSUWPFVWCPO-UHFFFAOYSA-N 0.000 description 1
- 239000010931 gold Substances 0.000 description 1
- 229910052737 gold Inorganic materials 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- LRDFRRGEGBBSRN-UHFFFAOYSA-N isobutyronitrile Chemical compound CC(C)C#N LRDFRRGEGBBSRN-UHFFFAOYSA-N 0.000 description 1
- 229920005684 linear copolymer Polymers 0.000 description 1
- 150000002690 malonic acid derivatives Chemical class 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
Classifications
-
- 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
- C09D133/04—Homopolymers or copolymers of esters
- C09D133/14—Homopolymers or copolymers of esters of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen
-
- 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
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/04—Acids; Metal salts or ammonium salts thereof
- C08F220/06—Acrylic acid; Methacrylic acid; Metal salts or ammonium salts thereof
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/62—Polymers of compounds having carbon-to-carbon double bonds
- C08G18/6283—Polymers of nitrogen containing compounds having carbon-to-carbon double bonds
-
- 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
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
- C08G59/26—Di-epoxy compounds heterocyclic
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Paints Or Removers (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Polyurethanes Or Polyureas (AREA)
- Epoxy Resins (AREA)
- Coating Of Shaped Articles Made Of Macromolecular Substances (AREA)
- Processes Of Treating Macromolecular Substances (AREA)
- Laminated Bodies (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
- Inorganic Chemistry (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US615191 | 1984-05-30 | ||
| US06/615,191 US4554318A (en) | 1984-05-30 | 1984-05-30 | Cyanoethylacrylate/acrylic acid copolymer |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS617315A true JPS617315A (ja) | 1986-01-14 |
| JPH0553807B2 JPH0553807B2 (OSRAM) | 1993-08-11 |
Family
ID=24464378
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP60116324A Granted JPS617315A (ja) | 1984-05-30 | 1985-05-29 | シアノエチルアクリレート／アクリル酸共重合体およびその製法 |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4554318A (OSRAM) |
| EP (1) | EP0169334B1 (OSRAM) |
| JP (1) | JPS617315A (OSRAM) |
| BR (1) | BR8502552A (OSRAM) |
| CA (1) | CA1269195A (OSRAM) |
| DE (1) | DE3567889D1 (OSRAM) |
| ES (2) | ES8606428A1 (OSRAM) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6370855A (ja) * | 1986-09-12 | 1988-03-31 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| WO2018061393A1 (ja) * | 2016-09-28 | 2018-04-05 | 住友理工株式会社 | 誘電エラストマー材料およびそれを用いたトランスデューサ |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3196361B2 (ja) * | 1991-12-25 | 2001-08-06 | 日立化成工業株式会社 | 塗料用樹脂組成物及び海中構造物用防汚塗料 |
| US5471554A (en) * | 1993-11-12 | 1995-11-28 | Ppg Industries, Inc. | Primer for electrochromic device with plastic substrate |
| US5520851A (en) * | 1993-11-12 | 1996-05-28 | Ppg Industries, Inc. | Iridium oxide film for electrochromic device |
| US5471338A (en) * | 1993-11-12 | 1995-11-28 | Ppg Industries, Inc. | Electrochromic device with plastic substrate |
| US5648149A (en) * | 1994-03-29 | 1997-07-15 | Ppg Industries, Inc. | Adhesion of thermoset polyurethane to rigid transparent substrates |
| EP0675157A1 (en) * | 1994-03-29 | 1995-10-04 | Ppg Industries, Inc. | Primer for adhering conductive films to acrylic or polycarbonate substrates |
| US5798860A (en) * | 1996-01-16 | 1998-08-25 | Ppg Industries, Inc. | Iridium oxide film for electrochromic device |
| US5776548A (en) * | 1996-11-05 | 1998-07-07 | Ppg Industries, Inc. | Primer for promoting adhesion of polyurethane to a metal oxide coating |
| US5994452A (en) * | 1996-11-05 | 1999-11-30 | Ppg Industries Ohio, Inc. | Primer for promoting adhesion of electroconductive metal oxide coating to plastic substrates |
| US5840429A (en) * | 1996-11-05 | 1998-11-24 | Ppg Industries, Inc. | Aircraft transparency |
| US5969847A (en) * | 1997-12-22 | 1999-10-19 | Ppg Industries Ohio, Inc. | Method for sealing a laminated electrochromic device edge |
| US5953150A (en) * | 1997-12-22 | 1999-09-14 | Ppg Industries Ohio, Inc. | Edge design for electrochromic devices |
| US6214261B1 (en) | 1998-03-23 | 2001-04-10 | Ppg Industries Ohio, Inc. | Method for forming a molded edge seal |
| US6924919B2 (en) | 2000-10-17 | 2005-08-02 | Ppg Industries Ohio, Inc. | Polymeric electrochromic devices |
| US6984287B2 (en) | 2001-11-02 | 2006-01-10 | The Dow Chemical Company | Primer composition for promoting adhesion of a urethane adhesive to a polymeric substrate |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4980155A (OSRAM) * | 1972-07-18 | 1974-08-02 |
Family Cites Families (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3242036A (en) * | 1962-12-31 | 1966-03-22 | Du Pont | Coating composition comprising an interpolymer of acrylonitrile, cyanoalkyl acrylate and an unsaturated carboxylic acid |
| DE1520124A1 (de) * | 1963-08-14 | 1969-07-10 | Ici Ltd | Verfahren zur Herstellung von Mischpolymeren |
| US3701758A (en) * | 1967-08-02 | 1972-10-31 | Nat Starch Chem Corp | Pressure-sensitive adhesives of cyanoacrylate polymers |
| US4154914A (en) * | 1976-05-01 | 1979-05-15 | Toyo Seal Kogyo Kabushiki Kaisha (Toyo Seal Industries Co., Ltd.) | Process for producing acrylic rubber by copolymerizing acrylic ester and malonic acid derivative having active methylene group |
| JPS6030348B2 (ja) * | 1978-06-15 | 1985-07-16 | 東レ株式会社 | 塗料用組成物 |
-
1984
- 1984-05-30 US US06/615,191 patent/US4554318A/en not_active Expired - Lifetime
-
1985
- 1985-05-23 DE DE8585106347T patent/DE3567889D1/de not_active Expired
- 1985-05-23 EP EP85106347A patent/EP0169334B1/en not_active Expired
- 1985-05-28 BR BR8502552A patent/BR8502552A/pt not_active IP Right Cessation
- 1985-05-29 JP JP60116324A patent/JPS617315A/ja active Granted
- 1985-05-29 CA CA000482713A patent/CA1269195A/en not_active Expired
- 1985-05-29 ES ES543598A patent/ES8606428A1/es not_active Expired
- 1985-11-29 ES ES549414A patent/ES8701811A1/es not_active Expired
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS4980155A (OSRAM) * | 1972-07-18 | 1974-08-02 |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPS6370855A (ja) * | 1986-09-12 | 1988-03-31 | Fuji Photo Film Co Ltd | ハロゲン化銀カラ−写真感光材料 |
| WO2018061393A1 (ja) * | 2016-09-28 | 2018-04-05 | 住友理工株式会社 | 誘電エラストマー材料およびそれを用いたトランスデューサ |
Also Published As
| Publication number | Publication date |
|---|---|
| ES8701811A1 (es) | 1986-12-01 |
| EP0169334B1 (en) | 1989-01-25 |
| BR8502552A (pt) | 1986-02-04 |
| ES543598A0 (es) | 1986-04-16 |
| DE3567889D1 (de) | 1989-03-02 |
| CA1269195A (en) | 1990-05-15 |
| EP0169334A1 (en) | 1986-01-29 |
| ES8606428A1 (es) | 1986-04-16 |
| US4554318A (en) | 1985-11-19 |
| JPH0553807B2 (OSRAM) | 1993-08-11 |
| ES549414A0 (es) | 1986-12-01 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| LAPS | Cancellation because of no payment of annual fees |