DE69222071T2 - Luftaktivierbare Polymerzusammensetzung - Google Patents
Luftaktivierbare PolymerzusammensetzungInfo
- Publication number
- DE69222071T2 DE69222071T2 DE69222071T DE69222071T DE69222071T2 DE 69222071 T2 DE69222071 T2 DE 69222071T2 DE 69222071 T DE69222071 T DE 69222071T DE 69222071 T DE69222071 T DE 69222071T DE 69222071 T2 DE69222071 T2 DE 69222071T2
- Authority
- DE
- Germany
- Prior art keywords
- air
- composition
- composition according
- groups
- compound
- 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.)
- Expired - Fee Related
Links
- 239000000203 mixture Substances 0.000 title claims abstract description 206
- 229920000642 polymer Polymers 0.000 title description 8
- 150000001875 compounds Chemical class 0.000 claims abstract description 49
- 239000000178 monomer Substances 0.000 claims abstract description 29
- 239000002253 acid Substances 0.000 claims abstract description 26
- 150000003839 salts Chemical class 0.000 claims abstract description 26
- 150000002978 peroxides Chemical class 0.000 claims abstract description 15
- 239000007859 condensation product Substances 0.000 claims abstract description 13
- 235000013877 carbamide Nutrition 0.000 claims abstract description 12
- 239000001257 hydrogen Substances 0.000 claims abstract description 12
- 229910052739 hydrogen Inorganic materials 0.000 claims abstract description 12
- 229910052757 nitrogen Inorganic materials 0.000 claims abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims abstract description 9
- 239000012190 activator Substances 0.000 claims abstract description 9
- 150000003997 cyclic ketones Chemical class 0.000 claims abstract description 7
- 239000004615 ingredient Substances 0.000 claims abstract description 7
- 238000003860 storage Methods 0.000 claims abstract description 7
- 229910017052 cobalt Inorganic materials 0.000 claims abstract description 6
- 239000010941 cobalt Substances 0.000 claims abstract description 6
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 claims abstract description 6
- 125000004433 nitrogen atom Chemical group N* 0.000 claims abstract description 6
- 239000002243 precursor Substances 0.000 claims abstract description 6
- 125000005842 heteroatom Chemical group 0.000 claims abstract description 5
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims abstract description 5
- 150000002460 imidazoles Chemical class 0.000 claims abstract description 4
- 150000002475 indoles Chemical class 0.000 claims abstract description 4
- 150000003222 pyridines Chemical class 0.000 claims abstract description 4
- 150000003672 ureas Chemical class 0.000 claims abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims abstract description 3
- 150000001716 carbazoles Chemical class 0.000 claims abstract description 3
- 229910052799 carbon Inorganic materials 0.000 claims abstract description 3
- 150000004885 piperazines Chemical class 0.000 claims abstract description 3
- 150000003233 pyrroles Chemical class 0.000 claims abstract description 3
- 150000003530 tetrahydroquinolines Chemical class 0.000 claims abstract description 3
- 238000000034 method Methods 0.000 claims description 27
- 229910052760 oxygen Inorganic materials 0.000 claims description 26
- 239000001301 oxygen Substances 0.000 claims description 26
- IAAASXBHFUJLHW-UHFFFAOYSA-N 3,5-diethyl-1-phenyl-2-propyl-2h-pyridine Chemical compound C1=C(CC)C=C(CC)C(CCC)N1C1=CC=CC=C1 IAAASXBHFUJLHW-UHFFFAOYSA-N 0.000 claims description 23
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 23
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical class [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 claims description 20
- 238000006116 polymerization reaction Methods 0.000 claims description 20
- -1 transition metal salts Chemical class 0.000 claims description 17
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 15
- 239000000758 substrate Substances 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical group N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 12
- 125000001183 hydrocarbyl group Chemical group 0.000 claims description 12
- 229910052742 iron Inorganic materials 0.000 claims description 12
- 125000003118 aryl group Chemical group 0.000 claims description 11
- LBUJPTNKIBCYBY-UHFFFAOYSA-N 1,2,3,4-tetrahydroquinoline Chemical compound C1=CC=C2CCCNC2=C1 LBUJPTNKIBCYBY-UHFFFAOYSA-N 0.000 claims description 10
- 150000003254 radicals Chemical class 0.000 claims description 10
- PAPNRQCYSFBWDI-UHFFFAOYSA-N 2,5-Dimethyl-1H-pyrrole Chemical compound CC1=CC=C(C)N1 PAPNRQCYSFBWDI-UHFFFAOYSA-N 0.000 claims description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims description 8
- 125000000217 alkyl group Chemical group 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 8
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 8
- 229920002554 vinyl polymer Polymers 0.000 claims description 8
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical group [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 7
- 239000000945 filler Substances 0.000 claims description 7
- 229910052717 sulfur Chemical group 0.000 claims description 7
- 239000011593 sulfur Chemical group 0.000 claims description 7
- YNGDWRXWKFWCJY-UHFFFAOYSA-N 1,4-Dihydropyridine Chemical compound C1C=CNC=C1 YNGDWRXWKFWCJY-UHFFFAOYSA-N 0.000 claims description 6
- 239000002262 Schiff base Substances 0.000 claims description 6
- 150000004753 Schiff bases Chemical class 0.000 claims description 6
- 239000002562 thickening agent Substances 0.000 claims description 6
- 125000004432 carbon atom Chemical group C* 0.000 claims description 5
- 238000000576 coating method Methods 0.000 claims description 5
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 5
- 229910052723 transition metal Inorganic materials 0.000 claims description 5
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical class OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000003545 alkoxy group Chemical group 0.000 claims description 4
- 239000003638 chemical reducing agent Substances 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 239000011347 resin Substances 0.000 claims description 4
- 229920005989 resin Polymers 0.000 claims description 4
- 239000003381 stabilizer Substances 0.000 claims description 4
- UXTIXCUXLURDHW-UHFFFAOYSA-N 1-butyl-3,5-diethyl-2-propyl-2h-pyridine Chemical compound CCCCN1C=C(CC)C=C(CC)C1CCC UXTIXCUXLURDHW-UHFFFAOYSA-N 0.000 claims description 3
- OXBLVCZKDOZZOJ-UHFFFAOYSA-N 2,3-Dihydrothiophene Chemical compound C1CC=CS1 OXBLVCZKDOZZOJ-UHFFFAOYSA-N 0.000 claims description 3
- 150000001252 acrylic acid derivatives Chemical group 0.000 claims description 3
- 125000002877 alkyl aryl group Chemical group 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- UNUQCUIGUVIOIK-UHFFFAOYSA-N ethyl 2,4-dimethyl-1,4-dihydropyridine-3-carboxylate Chemical compound CCOC(=O)C1=C(C)NC=CC1C UNUQCUIGUVIOIK-UHFFFAOYSA-N 0.000 claims description 3
- 125000005843 halogen group Chemical group 0.000 claims description 3
- 125000002950 monocyclic group Chemical group 0.000 claims description 3
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 3
- 239000000049 pigment Substances 0.000 claims description 3
- 125000003367 polycyclic group Chemical group 0.000 claims description 3
- 125000003808 silyl group Chemical group [H][Si]([H])([H])[*] 0.000 claims description 3
- KROCHRAIZPBMBP-UHFFFAOYSA-N 1-cyclohexyl-3,5-diethyl-2-propyl-2h-pyridine Chemical compound C1=C(CC)C=C(CC)C(CCC)N1C1CCCCC1 KROCHRAIZPBMBP-UHFFFAOYSA-N 0.000 claims description 2
- PYFVEIDRTLBMHG-UHFFFAOYSA-N 2,3-dimethyl-1h-indole Chemical compound C1=CC=C2C(C)=C(C)NC2=C1 PYFVEIDRTLBMHG-UHFFFAOYSA-N 0.000 claims description 2
- RNIPJYFZGXJSDD-UHFFFAOYSA-N 2,4,5-triphenyl-1h-imidazole Chemical compound C1=CC=CC=C1C1=NC(C=2C=CC=CC=2)=C(C=2C=CC=CC=2)N1 RNIPJYFZGXJSDD-UHFFFAOYSA-N 0.000 claims description 2
- MFFMQGGZCLEMCI-UHFFFAOYSA-N 2,4-dimethyl-1h-pyrrole Chemical compound CC1=CNC(C)=C1 MFFMQGGZCLEMCI-UHFFFAOYSA-N 0.000 claims description 2
- YEWOJJQYLXOPBS-UHFFFAOYSA-N 3,5-diethyl-1-(4-methoxyphenyl)-2-propyl-2h-pyridine Chemical compound C1=C(CC)C=C(CC)C(CCC)N1C1=CC=C(OC)C=C1 YEWOJJQYLXOPBS-UHFFFAOYSA-N 0.000 claims description 2
- ZEBBLOXDLGIMEG-UHFFFAOYSA-N 3-ethyl-2,4-dimethyl-1h-pyrrole Chemical compound CCC=1C(C)=CNC=1C ZEBBLOXDLGIMEG-UHFFFAOYSA-N 0.000 claims description 2
- PSVDLMGPEGPXTR-UHFFFAOYSA-N 4,5,6,9-tetrahydro-3h-carbazole Chemical compound C1CC=CC2=C1C(CCC=C1)=C1N2 PSVDLMGPEGPXTR-UHFFFAOYSA-N 0.000 claims description 2
- GZSTUEGIANKNTE-UHFFFAOYSA-N 5-methoxy-2,3-dimethyl-1h-indole Chemical compound COC1=CC=C2NC(C)=C(C)C2=C1 GZSTUEGIANKNTE-UHFFFAOYSA-N 0.000 claims description 2
- YZPJEXBGWCXBPS-UHFFFAOYSA-N 5-methoxy-3-methyl-2-phenyl-1h-indole Chemical compound CC=1C2=CC(OC)=CC=C2NC=1C1=CC=CC=C1 YZPJEXBGWCXBPS-UHFFFAOYSA-N 0.000 claims description 2
- LPYJYNGQAQWWPJ-UHFFFAOYSA-N 6-benzyl-5-phenyl-2,3,4,5-tetrahydropyridine Chemical compound C=1C=CC=CC=1CC1=NCCCC1C1=CC=CC=C1 LPYJYNGQAQWWPJ-UHFFFAOYSA-N 0.000 claims description 2
- SCZKDJKCKYLDHP-UHFFFAOYSA-N 6-methyl-5-phenyl-2,3,4,5-tetrahydropyridine Chemical compound CC1=NCCCC1C1=CC=CC=C1 SCZKDJKCKYLDHP-UHFFFAOYSA-N 0.000 claims description 2
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical class [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 claims description 2
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 125000004450 alkenylene group Chemical group 0.000 claims description 2
- 125000002947 alkylene group Chemical group 0.000 claims description 2
- 125000000304 alkynyl group Chemical group 0.000 claims description 2
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 2
- 239000011248 coating agent Substances 0.000 claims description 2
- 150000002688 maleic acid derivatives Chemical class 0.000 claims description 2
- 229910052748 manganese Inorganic materials 0.000 claims description 2
- 239000011572 manganese Chemical class 0.000 claims description 2
- FMOUEDXIDMVMJW-UHFFFAOYSA-N n-benzyl-1,4-dihydropyridine-3-carboxamide Chemical compound C=1NC=CCC=1C(=O)NCC1=CC=CC=C1 FMOUEDXIDMVMJW-UHFFFAOYSA-N 0.000 claims description 2
- 230000000379 polymerizing effect Effects 0.000 claims description 2
- WHMCXOWRIWJBIG-UHFFFAOYSA-N trimethyl(4h-pyridin-1-yl)silane Chemical compound C[Si](C)(C)N1C=CCC=C1 WHMCXOWRIWJBIG-UHFFFAOYSA-N 0.000 claims description 2
- 229920006337 unsaturated polyester resin Polymers 0.000 claims description 2
- FSJSYDFBTIVUFD-SUKNRPLKSA-N (z)-4-hydroxypent-3-en-2-one;oxovanadium Chemical compound [V]=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O FSJSYDFBTIVUFD-SUKNRPLKSA-N 0.000 claims 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 claims 1
- UDJZTGMLYITLIQ-UHFFFAOYSA-N 1-ethenylpyrrolidine Chemical compound C=CN1CCCC1 UDJZTGMLYITLIQ-UHFFFAOYSA-N 0.000 claims 1
- 125000003903 2-propenyl group Chemical group [H]C([*])([H])C([H])=C([H])[H] 0.000 claims 1
- MFWFDRBPQDXFRC-UHFFFAOYSA-N 4-hydroxypent-3-en-2-one;vanadium Chemical group [V].CC(O)=CC(C)=O.CC(O)=CC(C)=O.CC(O)=CC(C)=O MFWFDRBPQDXFRC-UHFFFAOYSA-N 0.000 claims 1
- UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 claims 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 claims 1
- REDXJYDRNCIFBQ-UHFFFAOYSA-N aluminium(3+) Chemical compound [Al+3] REDXJYDRNCIFBQ-UHFFFAOYSA-N 0.000 claims 1
- 239000001110 calcium chloride Substances 0.000 claims 1
- 229910001628 calcium chloride Inorganic materials 0.000 claims 1
- 239000012975 dibutyltin dilaurate Substances 0.000 claims 1
- JRMUNVKIHCOMHV-UHFFFAOYSA-M tetrabutylammonium bromide Chemical compound [Br-].CCCC[N+](CCCC)(CCCC)CCCC JRMUNVKIHCOMHV-UHFFFAOYSA-M 0.000 claims 1
- 229910052720 vanadium Chemical class 0.000 claims 1
- GPPXJZIENCGNKB-UHFFFAOYSA-N vanadium Chemical class [V]#[V] GPPXJZIENCGNKB-UHFFFAOYSA-N 0.000 claims 1
- 125000004925 dihydropyridyl group Chemical group N1(CC=CC=C1)* 0.000 abstract description 2
- 150000002505 iron Chemical class 0.000 abstract description 2
- 238000009472 formulation Methods 0.000 description 83
- 239000000853 adhesive Substances 0.000 description 43
- 230000001070 adhesive effect Effects 0.000 description 43
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 37
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 26
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 23
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 19
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 18
- 229910052751 metal Inorganic materials 0.000 description 14
- 239000002184 metal Substances 0.000 description 14
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 9
- 230000004913 activation Effects 0.000 description 9
- 239000007795 chemical reaction product Substances 0.000 description 8
- 150000001299 aldehydes Chemical class 0.000 description 7
- 229910052782 aluminium Chemical class 0.000 description 7
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical class [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 7
- VGVHNLRUAMRIEW-UHFFFAOYSA-N 4-methylcyclohexan-1-one Chemical compound CC1CCC(=O)CC1 VGVHNLRUAMRIEW-UHFFFAOYSA-N 0.000 description 6
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 6
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- ZTQSAGDEMFDKMZ-UHFFFAOYSA-N Butyraldehyde Chemical compound CCCC=O ZTQSAGDEMFDKMZ-UHFFFAOYSA-N 0.000 description 6
- 238000006482 condensation reaction Methods 0.000 description 6
- CDVAIHNNWWJFJW-UHFFFAOYSA-N 3,5-diethoxycarbonyl-1,4-dihydrocollidine Chemical compound CCOC(=O)C1=C(C)NC(C)=C(C(=O)OCC)C1C CDVAIHNNWWJFJW-UHFFFAOYSA-N 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 239000003921 oil Substances 0.000 description 5
- 239000007787 solid Substances 0.000 description 5
- 239000012298 atmosphere Substances 0.000 description 4
- AVWLPUQJODERGA-UHFFFAOYSA-L cobalt(2+);diiodide Chemical compound [Co+2].[I-].[I-] AVWLPUQJODERGA-UHFFFAOYSA-L 0.000 description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
- 229920002681 hypalon Polymers 0.000 description 4
- 239000003999 initiator Substances 0.000 description 4
- 239000000463 material Substances 0.000 description 4
- 238000010526 radical polymerization reaction Methods 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 3
- 235000011054 acetic acid Nutrition 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 238000013019 agitation Methods 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 150000002466 imines Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- 150000002739 metals Chemical class 0.000 description 3
- MQWCXKGKQLNYQG-UHFFFAOYSA-N methyl cyclohexan-4-ol Natural products CC1CCC(O)CC1 MQWCXKGKQLNYQG-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 3
- 150000003624 transition metals Chemical class 0.000 description 3
- HWSSEYVMGDIFMH-UHFFFAOYSA-N 2-[2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOC(=O)C(C)=C HWSSEYVMGDIFMH-UHFFFAOYSA-N 0.000 description 2
- UJBOOUHRTQVGRU-UHFFFAOYSA-N 3-methylcyclohexan-1-one Chemical compound CC1CCCC(=O)C1 UJBOOUHRTQVGRU-UHFFFAOYSA-N 0.000 description 2
- OYPRJOBELJOOCE-UHFFFAOYSA-N Calcium Chemical compound [Ca] OYPRJOBELJOOCE-UHFFFAOYSA-N 0.000 description 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 2
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 2
- WHNWPMSKXPGLAX-UHFFFAOYSA-N N-Vinyl-2-pyrrolidone Chemical compound C=CN1CCCC1=O WHNWPMSKXPGLAX-UHFFFAOYSA-N 0.000 description 2
- GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 2
- 239000004698 Polyethylene Substances 0.000 description 2
- KAESVJOAVNADME-UHFFFAOYSA-N Pyrrole Chemical compound C=1C=CNC=1 KAESVJOAVNADME-UHFFFAOYSA-N 0.000 description 2
- 239000000443 aerosol Substances 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- 229910052791 calcium Inorganic materials 0.000 description 2
- 239000011575 calcium Substances 0.000 description 2
- 150000001735 carboxylic acids Chemical class 0.000 description 2
- 239000000460 chlorine Substances 0.000 description 2
- 229910052801 chlorine Inorganic materials 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 239000007789 gas Substances 0.000 description 2
- 238000010348 incorporation Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 2
- 230000007246 mechanism Effects 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 238000005065 mining Methods 0.000 description 2
- 238000000465 moulding Methods 0.000 description 2
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 2
- 229920000573 polyethylene Polymers 0.000 description 2
- 239000004848 polyfunctional curative Substances 0.000 description 2
- 239000004926 polymethyl methacrylate Substances 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- CVHZOJJKTDOEJC-UHFFFAOYSA-N saccharin Chemical compound C1=CC=C2C(=O)NS(=O)(=O)C2=C1 CVHZOJJKTDOEJC-UHFFFAOYSA-N 0.000 description 2
- 229940081974 saccharin Drugs 0.000 description 2
- 235000019204 saccharin Nutrition 0.000 description 2
- 239000000901 saccharin and its Na,K and Ca salt Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N sulfuryl dichloride Chemical compound ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- 230000002195 synergetic effect Effects 0.000 description 2
- YNJBWRMUSHSURL-UHFFFAOYSA-N trichloroacetic acid Chemical compound OC(=O)C(Cl)(Cl)Cl YNJBWRMUSHSURL-UHFFFAOYSA-N 0.000 description 2
- 150000003673 urethanes Chemical class 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 125000006527 (C1-C5) alkyl group Chemical group 0.000 description 1
- 125000004169 (C1-C6) alkyl group Chemical group 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- MFWFDRBPQDXFRC-LNTINUHCSA-N (z)-4-hydroxypent-3-en-2-one;vanadium Chemical compound [V].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O MFWFDRBPQDXFRC-LNTINUHCSA-N 0.000 description 1
- WBYWAXJHAXSJNI-VOTSOKGWSA-M .beta-Phenylacrylic acid Natural products [O-]C(=O)\C=C\C1=CC=CC=C1 WBYWAXJHAXSJNI-VOTSOKGWSA-M 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
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- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
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- HPXRVTGHNJAIIH-UHFFFAOYSA-N cyclohexanol Chemical compound OC1CCCCC1 HPXRVTGHNJAIIH-UHFFFAOYSA-N 0.000 description 1
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 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
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- GUJOJGAPFQRJSV-UHFFFAOYSA-N dialuminum;dioxosilane;oxygen(2-);hydrate Chemical compound O.[O-2].[O-2].[O-2].[Al+3].[Al+3].O=[Si]=O.O=[Si]=O.O=[Si]=O.O=[Si]=O GUJOJGAPFQRJSV-UHFFFAOYSA-N 0.000 description 1
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- VZCYOOQTPOCHFL-OWOJBTEDSA-L fumarate(2-) Chemical compound [O-]C(=O)\C=C\C([O-])=O VZCYOOQTPOCHFL-OWOJBTEDSA-L 0.000 description 1
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- SGGOJYZMTYGPCH-UHFFFAOYSA-L manganese(2+);naphthalene-2-carboxylate Chemical compound [Mn+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 SGGOJYZMTYGPCH-UHFFFAOYSA-L 0.000 description 1
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- WBYWAXJHAXSJNI-UHFFFAOYSA-N methyl p-hydroxycinnamate Natural products OC(=O)C=CC1=CC=CC=C1 WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
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- 150000002763 monocarboxylic acids Chemical class 0.000 description 1
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- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
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- 239000002685 polymerization catalyst Substances 0.000 description 1
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- 239000000047 product Substances 0.000 description 1
- KOODSCBKXPPKHE-UHFFFAOYSA-N propanethioic s-acid Chemical compound CCC(S)=O KOODSCBKXPPKHE-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- IUVKMZGDUIUOCP-BTNSXGMBSA-N quinbolone Chemical compound O([C@H]1CC[C@H]2[C@H]3[C@@H]([C@]4(C=CC(=O)C=C4CC3)C)CC[C@@]21C)C1=CCCC1 IUVKMZGDUIUOCP-BTNSXGMBSA-N 0.000 description 1
- 150000004053 quinones Chemical class 0.000 description 1
- 230000002829 reductive effect Effects 0.000 description 1
- 230000004044 response Effects 0.000 description 1
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- 239000000565 sealant Substances 0.000 description 1
- 229910000077 silane Inorganic materials 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- 230000009974 thixotropic effect Effects 0.000 description 1
- 239000012207 thread-locking agent Substances 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 230000000699 topical effect Effects 0.000 description 1
- HTSABYAWKQAHBT-UHFFFAOYSA-N trans 3-methylcyclohexanol Natural products CC1CCCC(O)C1 HTSABYAWKQAHBT-UHFFFAOYSA-N 0.000 description 1
- 229910001428 transition metal ion Inorganic materials 0.000 description 1
- 125000004665 trialkylsilyl group Chemical group 0.000 description 1
- UORVGPXVDQYIDP-UHFFFAOYSA-N trihydridoboron Substances B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 1
- 238000009827 uniform distribution Methods 0.000 description 1
- HGBOYTHUEUWSSQ-UHFFFAOYSA-N valeric aldehyde Natural products CCCCC=O HGBOYTHUEUWSSQ-UHFFFAOYSA-N 0.000 description 1
- 150000003681 vanadium Chemical class 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
Classifications
-
- 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
- C08F210/00—Copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J5/00—Manufacture of articles or shaped materials containing macromolecular substances
- C08J5/12—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives
- C08J5/124—Bonding of a preformed macromolecular material to the same or other solid material such as metal, glass, leather, e.g. using adhesives using adhesives based on a macromolecular component
-
- 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
- C08F4/00—Polymerisation catalysts
-
- 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
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2327/00—Characterised by the use of 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 a halogen; Derivatives of such polymers
- C08J2327/02—Characterised by the use of 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 a halogen; Derivatives of such polymers not modified by chemical after-treatment
- C08J2327/04—Characterised by the use of 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 a halogen; Derivatives of such polymers not modified by chemical after-treatment containing chlorine atoms
- C08J2327/06—Homopolymers or copolymers of vinyl chloride
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Polymers & Plastics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Materials Engineering (AREA)
- Engineering & Computer Science (AREA)
- Manufacturing & Machinery (AREA)
- Polymerisation Methods In General (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Polymerization Catalysts (AREA)
- Paints Or Removers (AREA)
- Sealing Material Composition (AREA)
- Agricultural Chemicals And Associated Chemicals (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
- Graft Or Block Polymers (AREA)
- Medicinal Preparation (AREA)
- Laminated Bodies (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| IE74291 | 1991-03-06 | ||
| IE74191A IE910741A1 (en) | 1991-03-06 | 1991-03-06 | Air activatable polymerisable compositions |
| IE920471 | 1992-02-13 |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69222071D1 DE69222071D1 (de) | 1997-10-16 |
| DE69222071T2 true DE69222071T2 (de) | 1998-02-05 |
Family
ID=27270327
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69222071T Expired - Fee Related DE69222071T2 (de) | 1991-03-06 | 1992-03-05 | Luftaktivierbare Polymerzusammensetzung |
Country Status (14)
| Country | Link |
|---|---|
| US (2) | US5523347A (index.php) |
| EP (1) | EP0502733B1 (index.php) |
| JP (1) | JP2952103B2 (index.php) |
| KR (1) | KR0178057B1 (index.php) |
| AT (1) | ATE157993T1 (index.php) |
| AU (1) | AU646148B2 (index.php) |
| BR (1) | BR9200743A (index.php) |
| CA (1) | CA2062400A1 (index.php) |
| DE (1) | DE69222071T2 (index.php) |
| DK (1) | DK0502733T3 (index.php) |
| ES (1) | ES2106824T3 (index.php) |
| MX (1) | MX9200971A (index.php) |
| NO (1) | NO300693B1 (index.php) |
| TW (1) | TW218883B (index.php) |
Families Citing this family (20)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5506326A (en) * | 1991-03-06 | 1996-04-09 | Loctite (Ireland) Limited | Air-activatable polymerizable compositions containing onium salts |
| CA2115607A1 (en) * | 1993-02-18 | 1994-08-19 | Brendan Kneafsey | Air-activatable polymerisable compositions containing onium salts |
| DE4420151A1 (de) * | 1994-06-09 | 1995-12-14 | Henkel Kgaa | Einkomponentiger Reaktionsklebstoff |
| IE941002A1 (en) * | 1994-12-22 | 1996-06-26 | Loctite Ireland Ltd | Air-activatable polymerisable compositions containing¹tetrazoles |
| JPH1060114A (ja) * | 1996-05-28 | 1998-03-03 | Loctite Ireland Ltd | 鉄化合物を用いるポリチオールおよびポリエンの貯蔵−安定性の１パーツ系空気活性化される配合組成物 |
| IE980775A1 (en) * | 1998-09-17 | 2000-03-22 | Loctite R & D Ltd | Auto-oxidation systems for air-activatable polymerisable compositions |
| FR2804121A1 (fr) | 2000-01-24 | 2001-07-27 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant une charge blanche renforcante et un systeme de couplage ( charge blanche/elastomere) |
| FR2804120A1 (fr) | 2000-01-24 | 2001-07-27 | Michelin Soc Tech | Composition de caoutchouc pour pneumatique comportant une charge blanche renforcante et un systeme de couplage (charge blanche/elstomere) |
| IE20000440A1 (en) * | 2000-05-31 | 2003-04-02 | Loctite R & D Ltd | Semi-Solid one- or two-part compositions |
| US6767356B2 (en) * | 2000-09-01 | 2004-07-27 | Angiolink Corporation | Advanced wound site management systems and methods |
| US6673440B2 (en) | 2000-11-06 | 2004-01-06 | Sterling Medivations, Inc. | Subcutaneous injection set tubing with solvent bonding |
| WO2003042311A1 (en) * | 2001-11-14 | 2003-05-22 | Loctite (R & D) Limited | Activator compositions for cyanoacrylate adhesives |
| WO2006026588A2 (en) * | 2004-08-30 | 2006-03-09 | Illinois Tool Works Inc. | Thixotropic anaerobic adhesive |
| CA2703865C (en) | 2007-10-29 | 2016-01-05 | Henkel Corporation | Thermally resistant anaerobically curable compositions |
| US20090288771A1 (en) * | 2008-05-23 | 2009-11-26 | Loctite (R&D) Limited | Surface-promoted cure of one-part radically curable compositions |
| US20090288770A1 (en) * | 2008-05-23 | 2009-11-26 | Loctite (R&D) Limited | Surface-promoted cure of one-part cationically curable compositions |
| US8399099B1 (en) * | 2008-05-23 | 2013-03-19 | Henkel Ireland Limited | Coating compositions |
| AU2009267786A1 (en) * | 2008-07-09 | 2010-01-14 | University Of Wollongong | Prepolymer composition |
| WO2010094634A1 (en) | 2009-02-17 | 2010-08-26 | Loctite (R & D) Limited | Cationically curable compositions and a primer therefor |
| WO2020100832A1 (ja) * | 2018-11-15 | 2020-05-22 | デンカ株式会社 | 組成物 |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| DE287796C (index.php) * | ||||
| US1780334A (en) * | 1926-02-12 | 1930-11-04 | Du Pont | Aldehyde amine condensation products |
| US2478066A (en) * | 1944-04-20 | 1949-08-02 | Shell Dev | Polymerization of olefins in the presence of nitrogen compounds |
| US2601293A (en) * | 1950-04-01 | 1952-06-24 | Du Pont | Polymerization initiation systems comprising a hydrazone, a peroxy compound, and cupric ion |
| AT335196B (de) * | 1974-07-26 | 1977-02-25 | Philips Nv | Markiervorrichtung fur ein aufzeichnungs- und/oder wiedergabegerat |
| DE2442000C2 (de) * | 1974-09-02 | 1983-11-24 | Henkel KGaA, 4000 Düsseldorf | Anaerob härtende Klebstoffe und Dichtungsmassen |
| DE2442001A1 (de) * | 1974-09-02 | 1976-03-18 | Henkel & Cie Gmbh | Anaerob haertende klebstoffe und dichtungsmassen |
| DE2441963A1 (de) * | 1974-09-02 | 1976-03-18 | Henkel & Cie Gmbh | Anaerob haertende klebstoffe und dichtungsmassen |
| US4343921A (en) * | 1978-11-06 | 1982-08-10 | Usm Corporation | Adhesive composition |
| US4287255A (en) * | 1979-09-06 | 1981-09-01 | Avery International Corporation | Reinforced adhesive tapes |
| GB2061294B (en) * | 1979-10-18 | 1984-02-08 | Bostik Ltd | Adhesives containing azine activators |
| DE3041904C2 (de) * | 1980-11-06 | 1984-11-22 | Henkel KGaA, 4000 Düsseldorf | Borverbindungen enthaltende lagerstabile Reaktionsklebstoffe |
| IE50442B1 (en) * | 1980-11-21 | 1986-04-16 | Loctite Corp | Two part adhesive composition |
| US4395361A (en) * | 1981-08-07 | 1983-07-26 | The Procter & Gamble Company | Catalysts for oxygen-initiated free-radical polymerization reactions |
| US4401793A (en) * | 1981-09-04 | 1983-08-30 | National Starch And Chemical Corporation | Polymeric adducts with pendant polymerizable double bonds, their preparation and use as reactive thickeners in improved anaerobic compositions |
| US4452955A (en) * | 1981-09-16 | 1984-06-05 | Minnesota Mining & Manufacturing Company | Novel adhesive compositions |
| JPS5915469A (ja) * | 1982-07-20 | 1984-01-26 | Semedain Kk | 室温硬化型二液性組成物 |
| CA1261538A (en) * | 1984-07-19 | 1989-09-26 | Ronald W. Novak | Aldehyde or imine oxygen scavengers for vinyl polymerizations |
| US4950701A (en) * | 1986-07-02 | 1990-08-21 | Cemedine Company, Ltd. | Bonding method and adhesive useful for the method |
| US4855373A (en) * | 1988-11-07 | 1989-08-08 | The Dow Chemical Company | Multi-sited hydrazone initiators of vinyl polymerization |
| US5045614A (en) * | 1989-04-07 | 1991-09-03 | The Dow Chemical Company | Process for polymerizing vinyl monomers using amine containing compounds which simultaneously act as initiators and crosslinking agents as part of a redox initiator system |
-
1992
- 1992-03-05 TW TW081101690A patent/TW218883B/zh active
- 1992-03-05 NO NO920871A patent/NO300693B1/no unknown
- 1992-03-05 AT AT92301899T patent/ATE157993T1/de not_active IP Right Cessation
- 1992-03-05 AU AU11439/92A patent/AU646148B2/en not_active Ceased
- 1992-03-05 DE DE69222071T patent/DE69222071T2/de not_active Expired - Fee Related
- 1992-03-05 EP EP92301899A patent/EP0502733B1/en not_active Expired - Lifetime
- 1992-03-05 ES ES92301899T patent/ES2106824T3/es not_active Expired - Lifetime
- 1992-03-05 DK DK92301899.8T patent/DK0502733T3/da active
- 1992-03-05 CA CA002062400A patent/CA2062400A1/en not_active Abandoned
- 1992-03-05 MX MX9200971A patent/MX9200971A/es unknown
- 1992-03-05 BR BR929200743A patent/BR9200743A/pt not_active IP Right Cessation
- 1992-03-06 KR KR1019920003716A patent/KR0178057B1/ko not_active Expired - Fee Related
- 1992-03-06 JP JP4084533A patent/JP2952103B2/ja not_active Expired - Lifetime
-
1993
- 1993-12-23 US US08/173,267 patent/US5523347A/en not_active Expired - Fee Related
-
1995
- 1995-06-02 US US08/460,252 patent/US5610251A/en not_active Expired - Fee Related
Also Published As
| Publication number | Publication date |
|---|---|
| KR0178057B1 (ko) | 1999-05-15 |
| US5610251A (en) | 1997-03-11 |
| ATE157993T1 (de) | 1997-09-15 |
| US5523347A (en) | 1996-06-04 |
| JP2952103B2 (ja) | 1999-09-20 |
| CA2062400A1 (en) | 1992-09-07 |
| NO920871L (no) | 1992-09-07 |
| BR9200743A (pt) | 1992-11-10 |
| EP0502733A1 (en) | 1992-09-09 |
| KR920018096A (ko) | 1992-10-21 |
| JPH05105846A (ja) | 1993-04-27 |
| MX9200971A (es) | 1992-09-01 |
| TW218883B (index.php) | 1994-01-11 |
| AU1143992A (en) | 1992-09-10 |
| DK0502733T3 (da) | 1997-12-29 |
| EP0502733B1 (en) | 1997-09-10 |
| AU646148B2 (en) | 1994-02-10 |
| NO920871D0 (no) | 1992-03-05 |
| DE69222071D1 (de) | 1997-10-16 |
| ES2106824T3 (es) | 1997-11-16 |
| NO300693B1 (no) | 1997-07-07 |
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