JPS5887103A - 硬化性組成物、その製法及びそれを使用する方法 - Google Patents
硬化性組成物、その製法及びそれを使用する方法Info
- Publication number
- JPS5887103A JPS5887103A JP57198791A JP19879182A JPS5887103A JP S5887103 A JPS5887103 A JP S5887103A JP 57198791 A JP57198791 A JP 57198791A JP 19879182 A JP19879182 A JP 19879182A JP S5887103 A JPS5887103 A JP S5887103A
- Authority
- JP
- Japan
- Prior art keywords
- methacrylate
- composition according
- component
- composition
- polymerization
- 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
- 239000000203 mixture Substances 0.000 title claims abstract description 37
- 238000004519 manufacturing process Methods 0.000 title claims 2
- 239000000178 monomer Substances 0.000 claims abstract description 18
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 14
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims abstract description 13
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
- 239000003999 initiator Substances 0.000 claims abstract description 10
- 239000002824 redox indicator Substances 0.000 claims abstract description 8
- -1 t-butyl peroxy-2-ethyl Chemical group 0.000 claims description 9
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 6
- RWGFKTVRMDUZSP-UHFFFAOYSA-N isopropyl-benzene Natural products CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 claims description 5
- 239000003505 polymerization initiator Substances 0.000 claims description 5
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 claims description 4
- PDQAZBWRQCGBEV-UHFFFAOYSA-N Ethylenethiourea Chemical compound S=C1NCCN1 PDQAZBWRQCGBEV-UHFFFAOYSA-N 0.000 claims description 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 4
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 claims description 4
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 claims description 4
- FLVIGYVXZHLUHP-UHFFFAOYSA-N N,N'-diethylthiourea Chemical compound CCNC(=S)NCC FLVIGYVXZHLUHP-UHFFFAOYSA-N 0.000 claims description 4
- RSAZYXZUJROYKR-UHFFFAOYSA-N indophenol Chemical compound C1=CC(O)=CC=C1N=C1C=CC(=O)C=C1 RSAZYXZUJROYKR-UHFFFAOYSA-N 0.000 claims description 4
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 claims description 4
- MGSRCZKZVOBKFT-UHFFFAOYSA-N thymol Chemical compound CC(C)C1=CC=C(C)C=C1O MGSRCZKZVOBKFT-UHFFFAOYSA-N 0.000 claims description 4
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 claims description 3
- MNOILHPDHOHILI-UHFFFAOYSA-N Tetramethylthiourea Chemical compound CN(C)C(=S)N(C)C MNOILHPDHOHILI-UHFFFAOYSA-N 0.000 claims description 3
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Natural products NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 3
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 claims description 3
- 150000003839 salts Chemical class 0.000 claims description 3
- QEQBMZQFDDDTPN-UHFFFAOYSA-N (2-methylpropan-2-yl)oxy benzenecarboperoxoate Chemical compound CC(C)(C)OOOC(=O)C1=CC=CC=C1 QEQBMZQFDDDTPN-UHFFFAOYSA-N 0.000 claims description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims description 2
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 claims description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 2
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 claims description 2
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 claims description 2
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 claims description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 claims description 2
- IPCRBOOJBPETMF-UHFFFAOYSA-N N-acetylthiourea Chemical compound CC(=O)NC(N)=S IPCRBOOJBPETMF-UHFFFAOYSA-N 0.000 claims description 2
- 239000005844 Thymol Substances 0.000 claims description 2
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 239000000654 additive Substances 0.000 claims description 2
- MCIYNZNEOWHWNI-UHFFFAOYSA-N chlorosulfinyloxybenzene Chemical compound ClS(=O)OC1=CC=CC=C1 MCIYNZNEOWHWNI-UHFFFAOYSA-N 0.000 claims description 2
- DQSHRNZTQWDMPJ-UHFFFAOYSA-N chlorosulfinyloxymethane Chemical compound COS(Cl)=O DQSHRNZTQWDMPJ-UHFFFAOYSA-N 0.000 claims description 2
- 229910052804 chromium Inorganic materials 0.000 claims description 2
- 239000011651 chromium Substances 0.000 claims description 2
- 239000010941 cobalt Substances 0.000 claims description 2
- 229910017052 cobalt Inorganic materials 0.000 claims description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims description 2
- 229910052802 copper Inorganic materials 0.000 claims description 2
- 239000010949 copper Substances 0.000 claims description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 claims description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 claims description 2
- 229910052742 iron Inorganic materials 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Substances 0.000 claims description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 claims description 2
- 229960000790 thymol Drugs 0.000 claims description 2
- 239000010936 titanium Substances 0.000 claims description 2
- 229910052719 titanium Inorganic materials 0.000 claims description 2
- 229910052720 vanadium Inorganic materials 0.000 claims description 2
- JLTDJTHDQAWBAV-UHFFFAOYSA-N N,N-dimethylaniline Chemical compound CN(C)C1=CC=CC=C1 JLTDJTHDQAWBAV-UHFFFAOYSA-N 0.000 claims 2
- 238000000034 method Methods 0.000 claims 2
- FYELGSIOXSRGGW-UHFFFAOYSA-N (2-aminoacetyl) 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(=O)CN FYELGSIOXSRGGW-UHFFFAOYSA-N 0.000 claims 1
- ZKALVNREMFLWAN-VOTSOKGWSA-N (ne)-n-(4-methylpentan-2-ylidene)hydroxylamine Chemical compound CC(C)C\C(C)=N\O ZKALVNREMFLWAN-VOTSOKGWSA-N 0.000 claims 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 claims 1
- YIVJZNGAASQVEM-UHFFFAOYSA-N Lauroyl peroxide Chemical compound CCCCCCCCCCCC(=O)OOC(=O)CCCCCCCCCCC YIVJZNGAASQVEM-UHFFFAOYSA-N 0.000 claims 1
- KFFQABQEJATQAT-UHFFFAOYSA-N N,N'-dibutylthiourea Chemical compound CCCCNC(=S)NCCCC KFFQABQEJATQAT-UHFFFAOYSA-N 0.000 claims 1
- 125000005595 acetylacetonate group Chemical group 0.000 claims 1
- 229910052783 alkali metal Inorganic materials 0.000 claims 1
- 239000000470 constituent Substances 0.000 claims 1
- 125000002592 cumenyl group Chemical group C1(=C(C=CC=C1)*)C(C)C 0.000 claims 1
- LNCPIMCVTKXXOY-UHFFFAOYSA-N hexyl 2-methylprop-2-enoate Chemical compound CCCCCCOC(=O)C(C)=C LNCPIMCVTKXXOY-UHFFFAOYSA-N 0.000 claims 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 claims 1
- 150000002978 peroxides Chemical class 0.000 claims 1
- QEMXHQIAXOOASZ-UHFFFAOYSA-N tetramethylammonium Chemical class C[N+](C)(C)C QEMXHQIAXOOASZ-UHFFFAOYSA-N 0.000 claims 1
- 229940066528 trichloroacetate Drugs 0.000 claims 1
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 claims 1
- YFTHZRPMJXBUME-UHFFFAOYSA-N tripropylamine Chemical compound CCCN(CCC)CCC YFTHZRPMJXBUME-UHFFFAOYSA-N 0.000 claims 1
- LEONUFNNVUYDNQ-UHFFFAOYSA-N vanadium atom Chemical compound [V] LEONUFNNVUYDNQ-UHFFFAOYSA-N 0.000 claims 1
- 239000000853 adhesive Substances 0.000 description 8
- 230000001070 adhesive effect Effects 0.000 description 8
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
- 239000004615 ingredient Substances 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920000459 Nitrile rubber Polymers 0.000 description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 239000004342 Benzoyl peroxide Substances 0.000 description 2
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- 235000019400 benzoyl peroxide Nutrition 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
- 150000003512 tertiary amines Chemical class 0.000 description 2
- JHNRZXQVBKRYKN-VQHVLOKHSA-N (ne)-n-(1-phenylethylidene)hydroxylamine Chemical compound O\N=C(/C)C1=CC=CC=C1 JHNRZXQVBKRYKN-VQHVLOKHSA-N 0.000 description 1
- POILWHVDKZOXJZ-ARJAWSKDSA-M (z)-4-oxopent-2-en-2-olate Chemical compound C\C([O-])=C\C(C)=O POILWHVDKZOXJZ-ARJAWSKDSA-M 0.000 description 1
- YHMYGUUIMTVXNW-UHFFFAOYSA-N 1,3-dihydrobenzimidazole-2-thione Chemical compound C1=CC=C2NC(S)=NC2=C1 YHMYGUUIMTVXNW-UHFFFAOYSA-N 0.000 description 1
- XHPBLHAZMLPNTF-UHFFFAOYSA-N 1-chlorosulfinyloxypropane Chemical compound CCCOS(Cl)=O XHPBLHAZMLPNTF-UHFFFAOYSA-N 0.000 description 1
- BTOVVHWKPVSLBI-UHFFFAOYSA-N 2-methylprop-1-enylbenzene Chemical compound CC(C)=CC1=CC=CC=C1 BTOVVHWKPVSLBI-UHFFFAOYSA-N 0.000 description 1
- POJNAHKFWBQMED-UHFFFAOYSA-N 3,5-dimethyl-1,3,5-oxadiazinane Chemical compound CN1COCN(C)C1 POJNAHKFWBQMED-UHFFFAOYSA-N 0.000 description 1
- SCWBSTVOWDDYHH-UHFFFAOYSA-N 4-amino-2,6-dichlorophenol;4-aminophenol Chemical compound NC1=CC=C(O)C=C1.NC1=CC(Cl)=C(O)C(Cl)=C1 SCWBSTVOWDDYHH-UHFFFAOYSA-N 0.000 description 1
- DBCAQXHNJOFNGC-UHFFFAOYSA-N 4-bromo-1,1,1-trifluorobutane Chemical compound FC(F)(F)CCCBr DBCAQXHNJOFNGC-UHFFFAOYSA-N 0.000 description 1
- LCKPEFUXKRSTMA-UHFFFAOYSA-N 6-propan-2-yl-7-oxabicyclo[4.1.0]hepta-2,4-diene Chemical compound C1=CC=CC2(C(C)C)C1O2 LCKPEFUXKRSTMA-UHFFFAOYSA-N 0.000 description 1
- 241000951471 Citrus junos Species 0.000 description 1
- VLCDUOXHFNUCKK-UHFFFAOYSA-N N,N'-Dimethylthiourea Chemical compound CNC(=S)NC VLCDUOXHFNUCKK-UHFFFAOYSA-N 0.000 description 1
- OKIZCWYLBDKLSU-UHFFFAOYSA-M N,N,N-Trimethylmethanaminium chloride Chemical compound [Cl-].C[N+](C)(C)C OKIZCWYLBDKLSU-UHFFFAOYSA-M 0.000 description 1
- FBWADIKARMIWNM-UHFFFAOYSA-N N-3,5-dichloro-4-hydroxyphenyl-1,4-benzoquinone imine Chemical group C1=C(Cl)C(O)=C(Cl)C=C1N=C1C=CC(=O)C=C1 FBWADIKARMIWNM-UHFFFAOYSA-N 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 235000013405 beer Nutrition 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- SKOLWUPSYHWYAM-UHFFFAOYSA-N carbonodithioic O,S-acid Chemical compound SC(S)=O SKOLWUPSYHWYAM-UHFFFAOYSA-N 0.000 description 1
- 238000005266 casting Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000002301 combined effect Effects 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Substances CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- LNMQRPPRQDGUDR-UHFFFAOYSA-N hexyl prop-2-enoate Chemical compound CCCCCCOC(=O)C=C LNMQRPPRQDGUDR-UHFFFAOYSA-N 0.000 description 1
- 150000002466 imines Chemical class 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- 230000003647 oxidation Effects 0.000 description 1
- 238000007254 oxidation reaction Methods 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 159000000000 sodium salts Chemical class 0.000 description 1
- FRUIYGAEJNTDCA-UHFFFAOYSA-M sodium;4-[(4-oxocyclohexa-2,5-dien-1-ylidene)amino]phenolate Chemical compound [Na+].C1=CC([O-])=CC=C1N=C1C=CC(=O)C=C1 FRUIYGAEJNTDCA-UHFFFAOYSA-M 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- YMBCJWGVCUEGHA-UHFFFAOYSA-M tetraethylammonium chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC YMBCJWGVCUEGHA-UHFFFAOYSA-M 0.000 description 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical compound [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 description 1
- 238000009736 wetting Methods 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
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polymerization Catalysts (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Dental Preparations (AREA)
- Macromonomer-Based Addition Polymer (AREA)
- Paints Or Removers (AREA)
- Polymerisation Methods In General (AREA)
- Iron Core Of Rotating Electric Machines (AREA)
- Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)
- Metal-Oxide And Bipolar Metal-Oxide Semiconductor Integrated Circuits (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB34288 | 1981-11-13 | ||
| GB8134288 | 1981-11-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS5887103A true JPS5887103A (ja) | 1983-05-24 |
| JPH0240090B2 JPH0240090B2 (en, 2012) | 1990-09-10 |
Family
ID=10525864
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP57198791A Granted JPS5887103A (ja) | 1981-11-13 | 1982-11-12 | 硬化性組成物、その製法及びそれを使用する方法 |
Country Status (13)
| Country | Link |
|---|---|
| US (1) | US4467079A (en, 2012) |
| EP (1) | EP0079703B1 (en, 2012) |
| JP (1) | JPS5887103A (en, 2012) |
| AT (1) | ATE22100T1 (en, 2012) |
| AU (1) | AU9037282A (en, 2012) |
| CA (1) | CA1216994A (en, 2012) |
| DE (1) | DE3273225D1 (en, 2012) |
| DK (1) | DK503182A (en, 2012) |
| ES (1) | ES517356A0 (en, 2012) |
| GR (1) | GR77777B (en, 2012) |
| NZ (1) | NZ202465A (en, 2012) |
| PT (1) | PT75833B (en, 2012) |
| ZA (1) | ZA828280B (en, 2012) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4569976A (en) * | 1984-10-18 | 1986-02-11 | The Kendall Company | Redox cure system for acrylic adhesive compositions |
| JPH066608B2 (ja) | 1985-08-06 | 1994-01-26 | 住友化学工業株式会社 | メタクリル酸エステル系重合体の製造方法 |
| JPH0625204B2 (ja) * | 1985-08-28 | 1994-04-06 | 住友化学工業株式会社 | ビニル系単量体の重合成形方法 |
| FR2630743B1 (fr) * | 1988-04-29 | 1990-08-31 | Gosselin Claude | Procede d'etancheification par injection d'un melange a base d'acrylamide et melange correspondant |
| US6369164B1 (en) | 1993-05-26 | 2002-04-09 | Dentsply G.M.B.H. | Polymerizable compounds and compositions |
| US5998499A (en) | 1994-03-25 | 1999-12-07 | Dentsply G.M.B.H. | Liquid crystalline (meth)acrylate compounds, composition and method |
| US20050043490A1 (en) * | 1993-05-26 | 2005-02-24 | Klee Joachim E. | Polymerizable compounds and compositions |
| US6353061B1 (en) | 1993-05-26 | 2002-03-05 | Dentsply Gmbh | α, ω-methacrylate terminated macromonomer compounds |
| CA2146816A1 (en) * | 1994-04-22 | 1995-10-23 | Joachim E. Klee | Process and composition for preparing a dental polymer product |
| DE19501933A1 (de) * | 1995-01-24 | 1996-07-25 | Henkel Kgaa | Aerob härtbarer Klebstoff |
| US5688883A (en) * | 1995-03-14 | 1997-11-18 | Dentsply Gmbh | Polymerizable composition |
| DE19751953A1 (de) | 1997-11-24 | 1999-05-27 | Henkel Kgaa | Funktionelle Farbstoffe als Indikator in aerob härtenden Zusammensetzungen |
| US6620846B1 (en) | 2000-08-02 | 2003-09-16 | Closure Medical Corporation | Absorbable adhesive compositions |
| US20060202158A1 (en) * | 2005-03-11 | 2006-09-14 | Chii-Shu Chen | Pigmented organic peroxides having disappearing red color |
| US9522099B2 (en) * | 2010-11-04 | 2016-12-20 | Kerr Corporation | Dental compositions having special functionality and a tri-barrel packaging and delivery system therefor |
| US9399004B2 (en) | 2010-11-04 | 2016-07-26 | Kerr Corporation | Dental composition having a redox indicator and method of using same |
| KR20150130450A (ko) | 2013-03-15 | 2015-11-23 | 쓰리엠 이노베이티브 프로퍼티즈 컴파니 | 염료로서의 벤조티아졸-2-일아조-페닐 화합물, 이 염료를 포함하는 조성물, 및 이러한 조성물의 경화도를 결정하는 방법 |
| US9889070B2 (en) * | 2013-03-28 | 2018-02-13 | Kuraray Noritake Dental Inc. | Curable composition |
| WO2015102967A1 (en) | 2013-12-30 | 2015-07-09 | 3M Innovative Properties Company | Compositions including a polythiol, an unsaturated compound, and a dye and methods relating to such compositions |
| JP6628726B2 (ja) | 2013-12-30 | 2020-01-15 | スリーエム イノベイティブ プロパティズ カンパニー | 染料、これから製造されたフィラー、該フィラーを含む組成物、及びこのような組成物の硬化度を決定する方法 |
| BR112017028509A2 (pt) | 2015-06-29 | 2018-08-28 | 3M Innovative Properties Co | composições incluindo um politiol, um composto insaturado e um corante, e métodos relacionados a tais composições |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2400041A (en) * | 1944-08-15 | 1946-05-07 | Shell Dev | Reaction products of tertiary organic hydroperoxides with formaldehyde |
| US3390121A (en) * | 1964-06-16 | 1968-06-25 | Argus Chem | Color indication in polyester resin curing |
| US3382296A (en) * | 1966-04-25 | 1968-05-07 | Eastman Kodak Co | Color indicators for determining degree of cure of polyester resins |
| US4065430A (en) * | 1973-02-13 | 1977-12-27 | Fuji Photo Film Co., Ltd. | Functional group containing polymer and method of preparing the same |
| DE2445715A1 (de) * | 1974-09-25 | 1976-04-08 | Pelikan Werke Wagner Guenther | Klebstoff mit indikatorfarbstoff |
| JPS532543A (en) * | 1976-06-29 | 1978-01-11 | Denki Kagaku Kogyo Kk | Rapid-setting acrylic resin adhesive |
| HU176137B (en) * | 1978-03-06 | 1980-12-28 | Muanyagipari Kutato Intezet | Process for controlled hardening unsaturated polyester r resines |
| DE3031757A1 (de) * | 1979-08-22 | 1981-03-26 | Nippon Oil Co., Ltd., Tokio/Tokyo | Verfahren zur herstellung von kunstharzen und diese kunstharze enthaltende massen |
| GB2061294B (en) * | 1979-10-18 | 1984-02-08 | Bostik Ltd | Adhesives containing azine activators |
-
1982
- 1982-10-28 AT AT82305721T patent/ATE22100T1/de not_active IP Right Cessation
- 1982-10-28 DE DE8282305721T patent/DE3273225D1/de not_active Expired
- 1982-10-28 EP EP82305721A patent/EP0079703B1/en not_active Expired
- 1982-11-10 CA CA000415327A patent/CA1216994A/en not_active Expired
- 1982-11-11 ZA ZA828280A patent/ZA828280B/xx unknown
- 1982-11-11 PT PT75833A patent/PT75833B/pt unknown
- 1982-11-11 AU AU90372/82A patent/AU9037282A/en not_active Abandoned
- 1982-11-11 DK DK503182A patent/DK503182A/da not_active Application Discontinuation
- 1982-11-11 NZ NZ202465A patent/NZ202465A/en unknown
- 1982-11-12 GR GR69807A patent/GR77777B/el unknown
- 1982-11-12 JP JP57198791A patent/JPS5887103A/ja active Granted
- 1982-11-12 ES ES517356A patent/ES517356A0/es active Granted
- 1982-11-12 US US06/441,064 patent/US4467079A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| DE3273225D1 (en) | 1986-10-16 |
| EP0079703B1 (en) | 1986-09-10 |
| GR77777B (en, 2012) | 1984-09-25 |
| JPH0240090B2 (en, 2012) | 1990-09-10 |
| EP0079703A1 (en) | 1983-05-25 |
| PT75833B (en) | 1985-07-26 |
| CA1216994A (en) | 1987-01-20 |
| ES8401510A1 (es) | 1983-12-16 |
| ES517356A0 (es) | 1983-12-16 |
| US4467079A (en) | 1984-08-21 |
| PT75833A (en) | 1982-12-01 |
| DK503182A (da) | 1983-05-14 |
| ATE22100T1 (de) | 1986-09-15 |
| AU9037282A (en) | 1983-05-19 |
| ZA828280B (en) | 1983-07-27 |
| NZ202465A (en) | 1985-02-28 |
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