JPS59500132A - エラストマ−ゴムを含有する強化シアノアクリレイト - Google Patents
エラストマ−ゴムを含有する強化シアノアクリレイトInfo
- Publication number
- JPS59500132A JPS59500132A JP83500679A JP50067983A JPS59500132A JP S59500132 A JPS59500132 A JP S59500132A JP 83500679 A JP83500679 A JP 83500679A JP 50067983 A JP50067983 A JP 50067983A JP S59500132 A JPS59500132 A JP S59500132A
- Authority
- JP
- Japan
- Prior art keywords
- ester
- copolymer
- acrylic
- acid alkyl
- rubber
- 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
- 229920001971 elastomer Polymers 0.000 title claims description 27
- 239000005060 rubber Substances 0.000 title claims description 20
- MWCLLHOVUTZFKS-UHFFFAOYSA-N Methyl cyanoacrylate Chemical compound COC(=O)C(=C)C#N MWCLLHOVUTZFKS-UHFFFAOYSA-N 0.000 title claims description 10
- 229920001651 Cyanoacrylate Polymers 0.000 title description 10
- 239000000178 monomer Substances 0.000 claims description 26
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 16
- 229920000642 polymer Polymers 0.000 claims description 14
- 229920001577 copolymer Polymers 0.000 claims description 13
- 229920000058 polyacrylate Polymers 0.000 claims description 13
- 229920000800 acrylic rubber Polymers 0.000 claims description 12
- 150000002148 esters Chemical class 0.000 claims description 11
- -1 acrylic acid alkoxy ester Chemical class 0.000 claims description 10
- FGBJXOREULPLGL-UHFFFAOYSA-N ethyl cyanoacrylate Chemical compound CCOC(=O)C(=C)C#N FGBJXOREULPLGL-UHFFFAOYSA-N 0.000 claims description 10
- 239000003112 inhibitor Substances 0.000 claims description 9
- 239000003973 paint Substances 0.000 claims description 8
- 239000000806 elastomer Substances 0.000 claims description 7
- 150000001336 alkenes Chemical class 0.000 claims description 6
- 239000003381 stabilizer Substances 0.000 claims description 5
- IJVRPNIWWODHHA-UHFFFAOYSA-N 2-cyanoprop-2-enoic acid Chemical compound OC(=O)C(=C)C#N IJVRPNIWWODHHA-UHFFFAOYSA-N 0.000 claims description 4
- 230000002378 acidificating effect Effects 0.000 claims description 3
- 150000003254 radicals Chemical class 0.000 claims description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
- 239000005977 Ethylene Substances 0.000 claims description 2
- 229940053009 ethyl cyanoacrylate Drugs 0.000 claims description 2
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 2
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 2
- 229920000728 polyester Polymers 0.000 claims description 2
- 229920002689 polyvinyl acetate Polymers 0.000 claims description 2
- 239000011118 polyvinyl acetate Substances 0.000 claims description 2
- 229920001519 homopolymer Polymers 0.000 claims 4
- OOLLAFOLCSJHRE-ZHAKMVSLSA-N ulipristal acetate Chemical compound C1=CC(N(C)C)=CC=C1[C@@H]1C2=C3CCC(=O)C=C3CC[C@H]2[C@H](CC[C@]2(OC(C)=O)C(C)=O)[C@]2(C)C1 OOLLAFOLCSJHRE-ZHAKMVSLSA-N 0.000 claims 2
- 229920000459 Nitrile rubber Polymers 0.000 claims 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 claims 1
- 229940096118 ella Drugs 0.000 claims 1
- 229920002239 polyacrylonitrile Polymers 0.000 claims 1
- 229910052710 silicon Inorganic materials 0.000 claims 1
- 239000010703 silicon Substances 0.000 claims 1
- 230000000087 stabilizing effect Effects 0.000 claims 1
- 239000000203 mixture Substances 0.000 description 43
- 239000000853 adhesive Substances 0.000 description 24
- 230000001070 adhesive effect Effects 0.000 description 24
- 239000000945 filler Substances 0.000 description 16
- RAHZWNYVWXNFOC-UHFFFAOYSA-N Sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 9
- 239000004830 Super Glue Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 9
- AFVFQIVMOAPDHO-UHFFFAOYSA-N Methanesulfonic acid Chemical compound CS(O)(=O)=O AFVFQIVMOAPDHO-UHFFFAOYSA-N 0.000 description 8
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 6
- 239000002253 acid Substances 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- 230000009477 glass transition Effects 0.000 description 6
- 125000005907 alkyl ester group Chemical group 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- 229940098779 methanesulfonic acid Drugs 0.000 description 4
- 239000004014 plasticizer Substances 0.000 description 4
- 150000008053 sultones Chemical class 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- 239000002562 thickening agent Substances 0.000 description 4
- LSNNMFCWUKXFEE-UHFFFAOYSA-M Bisulfite Chemical compound OS([O-])=O LSNNMFCWUKXFEE-UHFFFAOYSA-M 0.000 description 3
- MWUXSHHQAYIFBG-UHFFFAOYSA-N Nitric oxide Chemical compound O=[N] MWUXSHHQAYIFBG-UHFFFAOYSA-N 0.000 description 3
- 239000012790 adhesive layer Substances 0.000 description 3
- 230000002411 adverse Effects 0.000 description 3
- 230000000704 physical effect Effects 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 230000008719 thickening Effects 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 229920013646 Hycar Polymers 0.000 description 2
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- 239000004721 Polyphenylene oxide Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 125000003342 alkenyl group Chemical group 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 2
- 229910052782 aluminium Inorganic materials 0.000 description 2
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 2
- 238000004090 dissolution Methods 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 239000012456 homogeneous solution Substances 0.000 description 2
- 239000004615 ingredient Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 229940063557 methacrylate Drugs 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000570 polyether Polymers 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- 150000003460 sulfonic acids Chemical class 0.000 description 2
- AKEJUJNQAAGONA-UHFFFAOYSA-N sulfur trioxide Chemical compound O=S(=O)=O AKEJUJNQAAGONA-UHFFFAOYSA-N 0.000 description 2
- 229920001897 terpolymer Polymers 0.000 description 2
- JHPBZFOKBAGZBL-UHFFFAOYSA-N (3-hydroxy-2,2,4-trimethylpentyl) 2-methylprop-2-enoate Chemical compound CC(C)C(O)C(C)(C)COC(=O)C(C)=C JHPBZFOKBAGZBL-UHFFFAOYSA-N 0.000 description 1
- QLUXVUVEVXYICG-UHFFFAOYSA-N 1,1-dichloroethene;prop-2-enenitrile Chemical compound C=CC#N.ClC(Cl)=C QLUXVUVEVXYICG-UHFFFAOYSA-N 0.000 description 1
- FEWFXBUNENSNBQ-UHFFFAOYSA-N 2-hydroxyacrylic acid Chemical compound OC(=C)C(O)=O FEWFXBUNENSNBQ-UHFFFAOYSA-N 0.000 description 1
- BDEDPKFUFGCVCJ-UHFFFAOYSA-N 3,6-dihydroxy-8,8-dimethyl-1-oxo-3,4,7,9-tetrahydrocyclopenta[h]isochromene-5-carbaldehyde Chemical compound O=C1OC(O)CC(C(C=O)=C2O)=C1C1=C2CC(C)(C)C1 BDEDPKFUFGCVCJ-UHFFFAOYSA-N 0.000 description 1
- REEBWSYYNPPSKV-UHFFFAOYSA-N 3-[(4-formylphenoxy)methyl]thiophene-2-carbonitrile Chemical compound C1=CC(C=O)=CC=C1OCC1=C(C#N)SC=C1 REEBWSYYNPPSKV-UHFFFAOYSA-N 0.000 description 1
- JIGUICYYOYEXFS-UHFFFAOYSA-N 3-tert-butylbenzene-1,2-diol Chemical compound CC(C)(C)C1=CC=CC(O)=C1O JIGUICYYOYEXFS-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-M Butyrate Chemical compound CCCC([O-])=O FERIUCNNQQJTOY-UHFFFAOYSA-M 0.000 description 1
- FERIUCNNQQJTOY-UHFFFAOYSA-N Butyric acid Natural products CCCC(O)=O FERIUCNNQQJTOY-UHFFFAOYSA-N 0.000 description 1
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- KRHYYFGTRYWZRS-UHFFFAOYSA-N Fluorane Chemical compound F KRHYYFGTRYWZRS-UHFFFAOYSA-N 0.000 description 1
- 241001441571 Hiodontidae Species 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920009204 Methacrylate-butadiene-styrene Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- 244000089486 Phragmites australis subsp australis Species 0.000 description 1
- 235000014676 Phragmites communis Nutrition 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- XBDQKXXYIPTUBI-UHFFFAOYSA-M Propionate Chemical compound CCC([O-])=O XBDQKXXYIPTUBI-UHFFFAOYSA-M 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical compound [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 235000018936 Vitellaria paradoxa Nutrition 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 125000005055 alkyl alkoxy group Chemical group 0.000 description 1
- 125000000129 anionic group Chemical group 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical compound C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 description 1
- 239000011575 calcium Substances 0.000 description 1
- 229910052791 calcium Inorganic materials 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 238000010382 chemical cross-linking Methods 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000013626 chemical specie Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000004140 cleaning Methods 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- NLCKLZIHJQEMCU-UHFFFAOYSA-N cyano prop-2-enoate Chemical class C=CC(=O)OC#N NLCKLZIHJQEMCU-UHFFFAOYSA-N 0.000 description 1
- 125000000392 cycloalkenyl group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003479 dental cement Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000010494 dissociation reaction Methods 0.000 description 1
- 230000005593 dissociations Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000013538 functional additive Substances 0.000 description 1
- 238000001879 gelation Methods 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- 229910000040 hydrogen fluoride Inorganic materials 0.000 description 1
- 238000010348 incorporation Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000005923 long-lasting effect Effects 0.000 description 1
- 125000005397 methacrylic acid ester group Chemical group 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 239000012766 organic filler Substances 0.000 description 1
- 125000000962 organic group Chemical group 0.000 description 1
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 238000005191 phase separation Methods 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001289 polyvinyl ether Polymers 0.000 description 1
- 238000011417 postcuring Methods 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 239000010453 quartz Substances 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000012744 reinforcing agent Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 238000007655 standard test method Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 238000003860 storage Methods 0.000 description 1
- 238000006467 substitution reaction Methods 0.000 description 1
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 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
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
- C09J4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00
-
- 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
- C08F291/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds according to more than one of the groups C08F251/00 - C08F289/00
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Paints Or Removers (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US06/339,952 US4440910A (en) | 1982-01-18 | 1982-01-18 | Toughened cyanoacrylates containing elastomeric rubbers |
| US339952CHEDE | 1982-01-18 | ||
| PCT/US1983/000081 WO1983002450A1 (en) | 1982-01-18 | 1983-01-17 | Toughened cyanoacrylates containing elastomers rubbers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS59500132A true JPS59500132A (ja) | 1984-01-26 |
| JPH0475268B2 JPH0475268B2 (enExample) | 1992-11-30 |
Family
ID=23331283
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP83500679A Granted JPS59500132A (ja) | 1982-01-18 | 1983-01-17 | エラストマ−ゴムを含有する強化シアノアクリレイト |
Country Status (7)
| Country | Link |
|---|---|
| US (1) | US4440910A (enExample) |
| EP (1) | EP0098877B1 (enExample) |
| JP (1) | JPS59500132A (enExample) |
| AU (1) | AU565343B2 (enExample) |
| DE (1) | DE3372491D1 (enExample) |
| MX (1) | MX163156B (enExample) |
| WO (1) | WO1983002450A1 (enExample) |
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466764A (en) * | 1993-09-17 | 1995-11-14 | Three Bond Co., Ltd. | Adhesive composition comprising a cyanoacrylate and an epoxy adduct |
| JP2012501361A (ja) * | 2008-09-01 | 2012-01-19 | ロックタイト （アール アンド ディー） リミテッド | 剥離基体上の転写可能な硬化性非液体フィルム |
| JP2012246328A (ja) * | 2011-05-25 | 2012-12-13 | Toagosei Co Ltd | 接着剤組成物 |
| JPWO2016093112A1 (ja) * | 2014-12-12 | 2017-11-09 | 東亞合成株式会社 | 二液型硬化性組成物 |
| WO2019180791A1 (ja) * | 2018-03-19 | 2019-09-26 | 日立化成株式会社 | 接着剤セット及び構造体の製造方法 |
Families Citing this family (100)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4560723A (en) * | 1983-11-14 | 1985-12-24 | Minnesota Mining And Manufacturing Company | Cyanoacrylate adhesive composition having sustained toughness |
| US4718966A (en) * | 1984-01-30 | 1988-01-12 | Loctite (Ireland) Ltd. | Bonding method utilizing cyanoacrylate adhesive having calixarene accelerator |
| US4636539A (en) * | 1984-01-30 | 1987-01-13 | Loctite (Ireland) Limited | Instant adhesive composition utilizing calixarene accelerators |
| US4574097A (en) * | 1984-08-10 | 1986-03-04 | Isopedix Corporation | Reinforced thixotropic gel composition |
| US4646765A (en) * | 1986-02-03 | 1987-03-03 | Cooper Donald E | Nail compositions containing cyanoacrylate and graphite |
| AU634121B1 (en) * | 1991-08-23 | 1993-02-11 | National Starch And Chemical Investment Holding Corporation | Toughened cyanoacrylate adhesive composition containing polyester polymers |
| US5328944A (en) * | 1992-07-14 | 1994-07-12 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties |
| US5424343A (en) * | 1992-10-08 | 1995-06-13 | Loctite Corporation | Thermally resistant cyanoacrylates employing substituted napthasultone additive |
| US5288794A (en) * | 1992-10-23 | 1994-02-22 | Loctite Corporation | Cyanoacrylate adhesives with improved cured thermal properties utilizing substituted aromatic additive |
| JPH0812946A (ja) * | 1994-06-28 | 1996-01-16 | Taoka Chem Co Ltd | 改質されたα−シアノアクリレート系接着剤組成物 |
| US5658415A (en) * | 1994-10-12 | 1997-08-19 | Montemurro; Elizabeth | Composition and process for attaching artificial nails |
| JPH08259899A (ja) * | 1995-03-23 | 1996-10-08 | Three Bond Co Ltd | シアノアクリレート系接着剤組成物 |
| US5922783A (en) * | 1997-02-27 | 1999-07-13 | Loctite Corporation | Radiation-curable, cyanoacrylate-containing compositions |
| US6512023B1 (en) * | 1998-06-18 | 2003-01-28 | Closure Medical Corporation | Stabilized monomer adhesive compositions |
| US6093780A (en) * | 1998-10-02 | 2000-07-25 | Loctite Corporation | Cyanoacrylate adhesive compositions with improved cured thermal properties |
| US20020025993A1 (en) * | 1998-12-11 | 2002-02-28 | Dr. Joachim E. Klee | Dental composition |
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| US2794788A (en) * | 1952-11-01 | 1957-06-04 | Eastman Kodak Co | Adhesive compositions containing alkyl esters of cyanoacrylic acid |
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| JPS6037836B2 (ja) * | 1977-08-05 | 1985-08-28 | 東亞合成株式会社 | 接着剤組成物 |
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-
1982
- 1982-01-18 US US06/339,952 patent/US4440910A/en not_active Expired - Lifetime
-
1983
- 1983-01-17 EP EP83900609A patent/EP0098877B1/en not_active Expired
- 1983-01-17 JP JP83500679A patent/JPS59500132A/ja active Granted
- 1983-01-17 MX MX195933A patent/MX163156B/es unknown
- 1983-01-17 WO PCT/US1983/000081 patent/WO1983002450A1/en not_active Ceased
- 1983-01-17 AU AU11581/83A patent/AU565343B2/en not_active Expired
- 1983-01-17 DE DE8383900609T patent/DE3372491D1/de not_active Expired
Cited By (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5466764A (en) * | 1993-09-17 | 1995-11-14 | Three Bond Co., Ltd. | Adhesive composition comprising a cyanoacrylate and an epoxy adduct |
| JP2012501361A (ja) * | 2008-09-01 | 2012-01-19 | ロックタイト （アール アンド ディー） リミテッド | 剥離基体上の転写可能な硬化性非液体フィルム |
| JP2012246328A (ja) * | 2011-05-25 | 2012-12-13 | Toagosei Co Ltd | 接着剤組成物 |
| JPWO2016093112A1 (ja) * | 2014-12-12 | 2017-11-09 | 東亞合成株式会社 | 二液型硬化性組成物 |
| WO2019180791A1 (ja) * | 2018-03-19 | 2019-09-26 | 日立化成株式会社 | 接着剤セット及び構造体の製造方法 |
Also Published As
| Publication number | Publication date |
|---|---|
| EP0098877B1 (en) | 1987-07-15 |
| MX163156B (es) | 1991-09-13 |
| EP0098877A4 (en) | 1984-07-03 |
| US4440910A (en) | 1984-04-03 |
| AU1158183A (en) | 1983-07-28 |
| WO1983002450A1 (en) | 1983-07-21 |
| EP0098877A1 (en) | 1984-01-25 |
| DE3372491D1 (en) | 1987-08-20 |
| AU565343B2 (en) | 1987-09-10 |
| JPH0475268B2 (enExample) | 1992-11-30 |
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