DE2622875C2 - Härtbare Zusammensetzungen - Google Patents
Härtbare ZusammensetzungenInfo
- Publication number
- DE2622875C2 DE2622875C2 DE2622875A DE2622875A DE2622875C2 DE 2622875 C2 DE2622875 C2 DE 2622875C2 DE 2622875 A DE2622875 A DE 2622875A DE 2622875 A DE2622875 A DE 2622875A DE 2622875 C2 DE2622875 C2 DE 2622875C2
- Authority
- DE
- Germany
- Prior art keywords
- radical
- carbon atoms
- methacrylate
- accelerator
- alkyl
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 18
- 239000000853 adhesive Substances 0.000 claims description 25
- 230000001070 adhesive effect Effects 0.000 claims description 25
- 239000003999 initiator Substances 0.000 claims description 16
- 150000002148 esters Chemical class 0.000 claims description 11
- 125000005396 acrylic acid ester group Chemical group 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 150000001875 compounds Chemical class 0.000 claims description 5
- 238000007789 sealing Methods 0.000 claims description 3
- 150000002429 hydrazines Chemical class 0.000 claims description 2
- -1 cycloalkenyl radical Chemical class 0.000 description 35
- 125000004432 carbon atom Chemical group C* 0.000 description 34
- 150000003254 radicals Chemical class 0.000 description 23
- 239000000178 monomer Substances 0.000 description 15
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 11
- 239000003085 diluting agent Substances 0.000 description 10
- 125000000217 alkyl group Chemical group 0.000 description 9
- 238000006243 chemical reaction Methods 0.000 description 9
- 239000011550 stock solution Substances 0.000 description 9
- 125000003118 aryl group Chemical group 0.000 description 8
- 239000000565 sealant Substances 0.000 description 8
- 125000003277 amino group Chemical group 0.000 description 7
- 125000000753 cycloalkyl group Chemical group 0.000 description 7
- 238000012360 testing method Methods 0.000 description 7
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 6
- 239000003112 inhibitor Substances 0.000 description 6
- FRIBMENBGGCKPD-UHFFFAOYSA-N 3-(2,3-dimethoxyphenyl)prop-2-enal Chemical compound COC1=CC=CC(C=CC=O)=C1OC FRIBMENBGGCKPD-UHFFFAOYSA-N 0.000 description 5
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 5
- 229920002125 Sokalan® Polymers 0.000 description 5
- 239000013466 adhesive and sealant Substances 0.000 description 5
- 125000003342 alkenyl group Chemical group 0.000 description 5
- 150000005840 aryl radicals Chemical class 0.000 description 5
- 239000004584 polyacrylic acid Substances 0.000 description 5
- 229920001223 polyethylene glycol Polymers 0.000 description 5
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 239000002202 Polyethylene glycol Substances 0.000 description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 4
- 239000011521 glass Substances 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 239000012948 isocyanate Substances 0.000 description 4
- 150000002513 isocyanates Chemical class 0.000 description 4
- 229920001228 polyisocyanate Polymers 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- MZGMQAMKOBOIDR-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCO MZGMQAMKOBOIDR-UHFFFAOYSA-N 0.000 description 3
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 3
- GNSFRPWPOGYVLO-UHFFFAOYSA-N 3-hydroxypropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCO GNSFRPWPOGYVLO-UHFFFAOYSA-N 0.000 description 3
- KSPIHGBHKVISFI-UHFFFAOYSA-N Diphenylcarbazide Chemical compound C=1C=CC=CC=1NNC(=O)NNC1=CC=CC=C1 KSPIHGBHKVISFI-UHFFFAOYSA-N 0.000 description 3
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 3
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M acrylate group Chemical group C(C=C)(=O)[O-] NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000002318 adhesion promoter Substances 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 125000000392 cycloalkenyl group Chemical group 0.000 description 3
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- STVZJERGLQHEKB-UHFFFAOYSA-N ethylene glycol dimethacrylate Chemical compound CC(=C)C(=O)OCCOC(=O)C(C)=C STVZJERGLQHEKB-UHFFFAOYSA-N 0.000 description 3
- 229930195733 hydrocarbon Natural products 0.000 description 3
- 150000003949 imides Chemical class 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000003381 stabilizer Substances 0.000 description 3
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 2
- BEWCNXNIQCLWHP-UHFFFAOYSA-N 2-(tert-butylamino)ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCNC(C)(C)C BEWCNXNIQCLWHP-UHFFFAOYSA-N 0.000 description 2
- WFUGQJXVXHBTEM-UHFFFAOYSA-N 2-hydroperoxy-2-(2-hydroperoxybutan-2-ylperoxy)butane Chemical compound CCC(C)(OO)OOC(C)(CC)OO WFUGQJXVXHBTEM-UHFFFAOYSA-N 0.000 description 2
- VHSHLMUCYSAUQU-UHFFFAOYSA-N 2-hydroxypropyl methacrylate Chemical compound CC(O)COC(=O)C(C)=C VHSHLMUCYSAUQU-UHFFFAOYSA-N 0.000 description 2
- KWOLFJPFCHCOCG-UHFFFAOYSA-N Acetophenone Chemical compound CC(=O)C1=CC=CC=C1 KWOLFJPFCHCOCG-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- RWGFKTVRMDUZSP-UHFFFAOYSA-N cumene Chemical compound CC(C)C1=CC=CC=C1 RWGFKTVRMDUZSP-UHFFFAOYSA-N 0.000 description 2
- 239000012933 diacyl peroxide Substances 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 238000001879 gelation Methods 0.000 description 2
- 229910052736 halogen Inorganic materials 0.000 description 2
- 125000005843 halogen group Chemical group 0.000 description 2
- 150000002367 halogens Chemical class 0.000 description 2
- 150000002432 hydroperoxides Chemical class 0.000 description 2
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 2
- 230000007774 longterm Effects 0.000 description 2
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- CXXPSOUBODTKJI-UHFFFAOYSA-N n'-(4-methylphenyl)acetohydrazide Chemical compound CC(=O)NNC1=CC=C(C)C=C1 CXXPSOUBODTKJI-UHFFFAOYSA-N 0.000 description 2
- CKLPECFHCLIYKN-UHFFFAOYSA-N n'-phenylbenzohydrazide Chemical compound C=1C=CC=CC=1C(=O)NNC1=CC=CC=C1 CKLPECFHCLIYKN-UHFFFAOYSA-N 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 150000002976 peresters Chemical class 0.000 description 2
- 239000004014 plasticizer Substances 0.000 description 2
- 230000002028 premature Effects 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- CIHOLLKRGTVIJN-UHFFFAOYSA-N tert‐butyl hydroperoxide Chemical compound CC(C)(C)OO CIHOLLKRGTVIJN-UHFFFAOYSA-N 0.000 description 2
- MRIKSZXJKCQQFT-UHFFFAOYSA-N (3-hydroxy-2,2-dimethylpropyl) prop-2-enoate Chemical compound OCC(C)(C)COC(=O)C=C MRIKSZXJKCQQFT-UHFFFAOYSA-N 0.000 description 1
- QUPKOUOXSNGVLB-UHFFFAOYSA-N 1,8-diisocyanatooctane Chemical compound O=C=NCCCCCCCCN=C=O QUPKOUOXSNGVLB-UHFFFAOYSA-N 0.000 description 1
- MCWMYICYUGCRDY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOCCOCCO MCWMYICYUGCRDY-UHFFFAOYSA-N 0.000 description 1
- QUASZQPLPKGIJY-UHFFFAOYSA-N 2-[2-[2-(2-hydroxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound OCCOCCOCCOCCOC(=O)C=C QUASZQPLPKGIJY-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QLIBJPGWWSHWBF-UHFFFAOYSA-N 2-aminoethyl methacrylate Chemical compound CC(=C)C(=O)OCCN QLIBJPGWWSHWBF-UHFFFAOYSA-N 0.000 description 1
- GLVYLTSKTCWWJR-UHFFFAOYSA-N 2-carbonoperoxoylbenzoic acid Chemical compound OOC(=O)C1=CC=CC=C1C(O)=O GLVYLTSKTCWWJR-UHFFFAOYSA-N 0.000 description 1
- SZTBMYHIYNGYIA-UHFFFAOYSA-M 2-chloroacrylate Chemical compound [O-]C(=O)C(Cl)=C SZTBMYHIYNGYIA-UHFFFAOYSA-M 0.000 description 1
- GPOGMJLHWQHEGF-UHFFFAOYSA-N 2-chloroethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCl GPOGMJLHWQHEGF-UHFFFAOYSA-N 0.000 description 1
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- UVJFHVAXZILJFX-UHFFFAOYSA-N 2-methylprop-2-enoic acid propane-1,2,3-triol Chemical compound CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.CC(=C)C(O)=O.OCC(O)CO UVJFHVAXZILJFX-UHFFFAOYSA-N 0.000 description 1
- RUMACXVDVNRZJZ-UHFFFAOYSA-N 2-methylpropyl 2-methylprop-2-enoate Chemical compound CC(C)COC(=O)C(C)=C RUMACXVDVNRZJZ-UHFFFAOYSA-N 0.000 description 1
- SNCMCDMEYCLVBO-UHFFFAOYSA-N 3-aminopropyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCN SNCMCDMEYCLVBO-UHFFFAOYSA-N 0.000 description 1
- QZPSOSOOLFHYRR-UHFFFAOYSA-N 3-hydroxypropyl prop-2-enoate Chemical compound OCCCOC(=O)C=C QZPSOSOOLFHYRR-UHFFFAOYSA-N 0.000 description 1
- XOJWAAUYNWGQAU-UHFFFAOYSA-N 4-(2-methylprop-2-enoyloxy)butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCOC(=O)C(C)=C XOJWAAUYNWGQAU-UHFFFAOYSA-N 0.000 description 1
- ZPQAKYPOZRXKFA-UHFFFAOYSA-N 6-Undecanone Chemical compound CCCCCC(=O)CCCCC ZPQAKYPOZRXKFA-UHFFFAOYSA-N 0.000 description 1
- OCIFJWVZZUDMRL-UHFFFAOYSA-N 6-hydroxyhexyl prop-2-enoate Chemical compound OCCCCCCOC(=O)C=C OCIFJWVZZUDMRL-UHFFFAOYSA-N 0.000 description 1
- YPMOAQISONSSNL-UHFFFAOYSA-N 8-hydroxyoctyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCCCCCCCO YPMOAQISONSSNL-UHFFFAOYSA-N 0.000 description 1
- 239000004925 Acrylic resin Substances 0.000 description 1
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical class C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- 239000004641 Diallyl-phthalate Substances 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 1
- UIHCLUNTQKBZGK-UHFFFAOYSA-N Methyl isobutyl ketone Natural products CCC(C)C(C)=O UIHCLUNTQKBZGK-UHFFFAOYSA-N 0.000 description 1
- DXCPEDGVEJWXRB-UHFFFAOYSA-N N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C Chemical compound N=C=O.N=C=O.CC1=CC(C)=C(C)C=C1C DXCPEDGVEJWXRB-UHFFFAOYSA-N 0.000 description 1
- 229930192627 Naphthoquinone Natural products 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- AVKHCKXGKPAGEI-UHFFFAOYSA-N Phenicarbazide Chemical compound NC(=O)NNC1=CC=CC=C1 AVKHCKXGKPAGEI-UHFFFAOYSA-N 0.000 description 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical group ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001253 acrylic acids Chemical class 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 125000003710 aryl alkyl group Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 1
- 239000012965 benzophenone Substances 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 239000004305 biphenyl Substances 0.000 description 1
- QUDWYFHPNIMBFC-UHFFFAOYSA-N bis(prop-2-enyl) benzene-1,2-dicarboxylate Chemical compound C=CCOC(=O)C1=CC=CC=C1C(=O)OCC=C QUDWYFHPNIMBFC-UHFFFAOYSA-N 0.000 description 1
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 1
- NDYYKTSANBCBBB-UHFFFAOYSA-N butan-1-ol;2-methylprop-2-enoic acid Chemical compound CCCCO.CC(=C)C(O)=O NDYYKTSANBCBBB-UHFFFAOYSA-N 0.000 description 1
- 229910052793 cadmium Inorganic materials 0.000 description 1
- BDOSMKKIYDKNTQ-UHFFFAOYSA-N cadmium atom Chemical compound [Cd] BDOSMKKIYDKNTQ-UHFFFAOYSA-N 0.000 description 1
- 238000001354 calcination Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000003857 carboxamides Chemical class 0.000 description 1
- 239000004359 castor oil Substances 0.000 description 1
- 235000019438 castor oil Nutrition 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 230000006378 damage Effects 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 150000002169 ethanolamines Chemical class 0.000 description 1
- UHESRSKEBRADOO-UHFFFAOYSA-N ethyl carbamate;prop-2-enoic acid Chemical class OC(=O)C=C.CCOC(N)=O UHESRSKEBRADOO-UHFFFAOYSA-N 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- ZEMPKEQAKRGZGQ-XOQCFJPHSA-N glycerol triricinoleate Natural products CCCCCC[C@@H](O)CC=CCCCCCCCC(=O)OC[C@@H](COC(=O)CCCCCCCC=CC[C@@H](O)CCCCCC)OC(=O)CCCCCCCC=CC[C@H](O)CCCCCC ZEMPKEQAKRGZGQ-XOQCFJPHSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 229940042795 hydrazides for tuberculosis treatment Drugs 0.000 description 1
- 150000002430 hydrocarbons Chemical class 0.000 description 1
- MHAJPDPJQMAIIY-UHFFFAOYSA-M hydroperoxide group Chemical group [O-]O MHAJPDPJQMAIIY-UHFFFAOYSA-M 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 235000021190 leftovers Nutrition 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- QIWOKEQEGOOGGH-UHFFFAOYSA-N n-anilinoformamide Chemical compound O=CNNC1=CC=CC=C1 QIWOKEQEGOOGGH-UHFFFAOYSA-N 0.000 description 1
- 150000002791 naphthoquinones Chemical class 0.000 description 1
- 125000004957 naphthylene group Chemical group 0.000 description 1
- 230000001590 oxidative effect Effects 0.000 description 1
- 125000000864 peroxy group Chemical group O(O*)* 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- DGTNSSLYPYDJGL-UHFFFAOYSA-N phenyl isocyanate Chemical compound O=C=NC1=CC=CC=C1 DGTNSSLYPYDJGL-UHFFFAOYSA-N 0.000 description 1
- 125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- FAIDIRVMPHBRLT-UHFFFAOYSA-N propane-1,2,3-triol;prop-2-enoic acid Chemical compound OC(=O)C=C.OC(=O)C=C.OCC(O)CO FAIDIRVMPHBRLT-UHFFFAOYSA-N 0.000 description 1
- 150000003152 propanolamines Chemical class 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- PYWVYCXTNDRMGF-UHFFFAOYSA-N rhodamine B Chemical compound [Cl-].C=12C=CC(=[N+](CC)CC)C=C2OC2=CC(N(CC)CC)=CC=C2C=1C1=CC=CC=C1C(O)=O PYWVYCXTNDRMGF-UHFFFAOYSA-N 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 239000002195 soluble material Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000000547 substituted alkyl group Chemical group 0.000 description 1
- 125000003107 substituted aryl group Chemical group 0.000 description 1
- 239000001384 succinic acid Substances 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- 239000011701 zinc 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
- 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)
- Sealing Material Composition (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US05/580,267 US4287330A (en) | 1975-05-23 | 1975-05-23 | Accelerator for curable compositions |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE2622875A1 DE2622875A1 (de) | 1976-12-09 |
| DE2622875C2 true DE2622875C2 (de) | 1985-05-30 |
Family
ID=24320406
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE2622875A Expired DE2622875C2 (de) | 1975-05-23 | 1976-05-21 | Härtbare Zusammensetzungen |
Country Status (9)
| Country | Link |
|---|---|
| US (1) | US4287330A (en:Method) |
| JP (1) | JPS6031872B2 (en:Method) |
| AU (1) | AU512342B2 (en:Method) |
| CA (1) | CA1062846A (en:Method) |
| DE (1) | DE2622875C2 (en:Method) |
| FR (1) | FR2311832A1 (en:Method) |
| GB (1) | GB1546468A (en:Method) |
| IT (1) | IT1069275B (en:Method) |
| NL (1) | NL188295C (en:Method) |
Families Citing this family (96)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4650845A (en) * | 1984-07-10 | 1987-03-17 | Minnesota Mining And Manufacturing Company | Ultra-violet light curable compositions for abrasion resistant articles |
| US4749592A (en) * | 1984-09-28 | 1988-06-07 | Minnesota Mining And Manufacturing Company | Grouting composition |
| US4764239A (en) * | 1985-07-24 | 1988-08-16 | Loctite Corporation | Substituted saccharin compounds and curable compositions containing same |
| US5021487A (en) * | 1988-05-27 | 1991-06-04 | Loctite Corporation | Thermally stabilized acrylic adhesive compositions and novel methacrylated malemide compounds useful therein |
| FR2658831B1 (fr) * | 1990-02-23 | 1992-05-15 | Ceca Sa | Compositions adhesives anaeorobies perfectionnees. |
| US5217760A (en) * | 1990-07-20 | 1993-06-08 | Loctite Corporation | Free radically curable formulations employing dithiolate catalysts |
| US5411998A (en) * | 1992-07-24 | 1995-05-02 | Loctite Limited | Curing anaerobic compositions through thick bondlines |
| US6043327A (en) * | 1997-07-03 | 2000-03-28 | Loctite Corporation | Anaerobic adhesive compositions of acrylates coreactants and maleimides curable under ambient conditions |
| CA2299417C (en) | 1997-07-03 | 2009-12-08 | Loctite Corporation | High temperature, controlled strength anaerobic adhesive compositions curable under ambient environmental conditions |
| US6150479A (en) * | 1998-11-23 | 2000-11-21 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
| US6342545B1 (en) | 1998-11-23 | 2002-01-29 | Loctite Corporation | Radical-curable adhesive compositions, reaction products of which demonstrate superior resistance to thermal degradation |
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| US6894082B2 (en) * | 2002-09-16 | 2005-05-17 | Henkel Corporation | Foamable compositions |
| US6627762B1 (en) | 2002-10-23 | 2003-09-30 | John G. Woods | Acetal and hemiacetal ester linked propylene carbonate functional (meth)acrylic esters and method of making same |
| JP2005002147A (ja) * | 2003-06-09 | 2005-01-06 | Yazaki Corp | 嫌気性接着剤組成物および嫌気性接着剤を使った電線の止水方法 |
| US7411025B1 (en) | 2003-12-22 | 2008-08-12 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| US6897277B1 (en) | 2003-12-22 | 2005-05-24 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| US7728092B1 (en) | 2006-04-13 | 2010-06-01 | Henkel Corporation | Anaerobically curable compositions |
| WO2008085286A1 (en) * | 2006-12-19 | 2008-07-17 | Henkel Corporation | (meth)acrylate compositions containing dispersions of core shell rubbers in (meth)acrylates |
| JP5566882B2 (ja) * | 2007-05-22 | 2014-08-06 | ヘンケル コーポレイション | 嫌気硬化性組成物 |
| WO2008153883A1 (en) * | 2007-06-08 | 2008-12-18 | Henkel Corporation | Room temperature curing adhesive composition having high temperature properties |
| US20090022894A1 (en) * | 2007-07-16 | 2009-01-22 | Henkel Corporation | Thermally Resistant Anaerobically Curable Compositions |
| US8598279B2 (en) | 2007-07-23 | 2013-12-03 | Henkel IP US LLC | Adducts useful as cure components for anaerobic curable compositions |
| MX2010004765A (es) | 2007-10-29 | 2010-07-02 | Henkel Corp | Composiciones curables anaerobicamente termicamente resistentes. |
| US20090188269A1 (en) | 2008-01-25 | 2009-07-30 | Henkel Corporation | High pressure connection systems and methods for their manufacture |
| US8106141B2 (en) * | 2008-05-07 | 2012-01-31 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| US8609881B2 (en) * | 2008-05-07 | 2013-12-17 | Henkel IP US LCC | Cure accelerators for anaerobic curable compositions |
| US20090278084A1 (en) * | 2008-05-07 | 2009-11-12 | Henkel Corporation | Cure accelerators for anaerobic curable compositions |
| DE102008023276A1 (de) * | 2008-05-13 | 2009-11-19 | Henkel Ag & Co. Kgaa | Verbinden von Rohren mit thermisch härtbaren Klebstoffen |
| WO2010080795A2 (en) | 2009-01-07 | 2010-07-15 | Henkel Corporation | Hydrogen peroxide complexes and their use in the cure system of anaerobic adhesives |
| WO2010090826A2 (en) | 2009-01-21 | 2010-08-12 | Henkel Corporation | Fast curing, two part anaerobic adhesive composition |
| US8188161B1 (en) | 2009-01-23 | 2012-05-29 | Henkel Corporation | Anaerobic cure systems for anaerobic curable compositions, and anaerobic curable compositions containing same |
| US7951884B1 (en) | 2009-03-31 | 2011-05-31 | Loctite (R&D) Limited | Cure accelerators for anaerobic adhesive compositions |
| CN102428152B (zh) | 2009-04-08 | 2013-07-31 | 汉高公司 | 膜状厌氧粘合剂和密封剂组合物、包含其的卷筒组合装置，及其在可配合的部件上的预涂物 |
| MX2011011029A (es) | 2009-05-01 | 2011-11-04 | Loctite R & D Ltd | Aceladores de curacion para composiciones curables anaerobias. |
| JP5620978B2 (ja) | 2009-05-01 | 2014-11-05 | ヘンケル コーポレイションＨｅｎｋｅｌ Ｃｏｒｐｏｒａｔｉｏｎ | 嫌気硬化性組成物用の硬化促進剤 |
| AU2010306807A1 (en) | 2009-10-15 | 2012-05-03 | Henkel Corporation | Anaerobically curable compositions |
| US9371473B2 (en) | 2012-06-27 | 2016-06-21 | Henkel IP & Holding GmbH | Accelerators for two step adhesive systems |
| US10590311B2 (en) | 2012-06-27 | 2020-03-17 | Henkel IP & Holding GmbH | Accelerators for two part curable compositions |
| US8986847B2 (en) | 2012-06-27 | 2015-03-24 | Henkel IP & Holding GmbH | Accelerator/oxidant/proton source combinations for two part curable compositions |
| US9365750B2 (en) | 2012-06-27 | 2016-06-14 | Henkel IP & Holding GmbH | Accelerators for curable compositions |
| CN102993990B (zh) * | 2012-10-31 | 2014-04-23 | 安徽东方金河精密机械制造有限公司 | 一种厌氧胶黏剂 |
| US10457762B2 (en) * | 2014-07-02 | 2019-10-29 | Mitsubishi Gas Chemical Company, Inc. | Diacrylate compound, composition thereof, and cured product thereof |
| WO2016018553A1 (en) | 2014-07-30 | 2016-02-04 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
| JP6695332B2 (ja) * | 2014-09-30 | 2020-05-20 | スリーエム イノベイティブ プロパティズ カンパニー | フリーラジカル重合方法及びそれによる物品 |
| WO2016054124A1 (en) | 2014-10-01 | 2016-04-07 | Henkel IP & Holding GmbH | Cure accelerators for anaerobic curable compositions |
| CA2964572C (en) * | 2014-10-22 | 2022-01-18 | Henkel IP & Holding GmbH | Phenylhydrazine/anhydride adducts and anaerobic curable compositions using same |
| GB2531717B (en) | 2014-10-24 | 2016-10-05 | Henkel IP & Holding GmbH | Anaerobic curable compositions |
| US10968310B1 (en) | 2015-04-28 | 2021-04-06 | Adhesive R&D, Inc. | Polymerizable materials, anaerobically curable compositions, and related methods and products |
| GB2538498B (en) | 2015-05-15 | 2017-12-20 | Henkel IP & Holding GmbH | Anaerobically curable (meth) acrylate compositions characterised by stabilisers with at least one glycinate group |
| EP3144073A1 (en) | 2015-09-17 | 2017-03-22 | Henkel AG & Co. KGaA | Dispenser, kit and method for applying an activator for a curable material |
| GB2543756B (en) | 2015-10-22 | 2017-10-18 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
| GB2546320B (en) | 2016-01-15 | 2018-02-14 | Henkel IP & Holding GmbH | Cure of anaerobic compositions |
| GB2548918B (en) | 2016-04-01 | 2020-07-15 | Henkel IP & Holding GmbH | Anaerobically curable (meth)acrylate compositions |
| GB201617938D0 (en) | 2016-10-24 | 2016-12-07 | Henkel IP & Holding GmbH | Sealant material |
| MX2019008294A (es) | 2017-01-20 | 2019-09-06 | Henkel IP & Holding GmbH | Sellador lubricante anaerobico. |
| GB2567875B (en) | 2017-10-27 | 2021-08-18 | Henkel IP & Holding GmbH | A pack for anaerobically curable compositions |
| WO2019123260A2 (en) * | 2017-12-19 | 2019-06-27 | 3M Innovative Properties Company | Multi-part composition having staged viscosity prior to hardening |
| WO2019231875A1 (en) | 2018-05-29 | 2019-12-05 | Henkel IP & Holding GmbH | Anaerobic paste compositions |
| GB201812113D0 (en) | 2018-07-25 | 2018-09-05 | Henkel IP & Holding GmbH | Anerobically curable compositions |
| GB2576002B (en) | 2018-07-31 | 2022-08-17 | Henkel Ag & Co Kgaa | Anaerobically curable compositions containing alpha-methylene-lactones |
| GB2576703B (en) | 2018-08-16 | 2022-07-13 | Henkel IP & Holding GmbH | Two step adhesive systems |
| KR102684589B1 (ko) | 2018-12-13 | 2024-07-15 | 헨켈 아이피 앤드 홀딩 게엠베하 | (메트)아크릴레이트-관능화된 왁스 및 그로 제조된 경화성 조성물 |
| GB2582919B (en) | 2019-04-05 | 2022-07-13 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
| GB2582957B (en) | 2019-04-11 | 2022-08-17 | Henkel IP & Holding GmbH | Anaerobically curable compositions |
| GB2583920B (en) | 2019-05-10 | 2023-09-27 | Henkel Ag & Co Kgaa | Method for bonding three-dimensional articles made by additive manufacturing |
| GB2584348B (en) | 2019-05-31 | 2023-01-04 | Henkel Ag & Co Kgaa | Curative free joint sealant |
| GB2585003B (en) | 2019-06-21 | 2022-09-28 | Henkel Ag & Co Kgaa | Anaerobically curable compositions |
| EP4061864B1 (en) | 2019-11-18 | 2023-10-18 | Henkel AG & Co. KGaA | One component (1k) anaerobic curable composition |
| GB2593754B (en) | 2020-04-01 | 2022-12-28 | Henkel Ag & Co Kgaa | Redox curable compositions and methods of manufacture thereof |
| GB2593752B (en) | 2020-04-01 | 2023-06-14 | Henkel Ag & Co Kgaa | Anaerobically curable compositions |
| ES3027607T3 (en) | 2020-08-18 | 2025-06-16 | Henkel Ag & Co Kgaa | Cure accelerators for anaerobic curable compositions |
| GB2606002B (en) | 2021-04-21 | 2023-06-14 | Henkel Ag & Co Kgaa | Anaerobically curable compositions |
| EP4269462A1 (en) | 2022-04-26 | 2023-11-01 | Henkel AG & Co. KGaA | Two component (2k) acrylic composition comprising a thermoplastic polyurethane |
| EP4269518A1 (en) | 2022-04-26 | 2023-11-01 | Henkel AG & Co. KGaA | Two component (2k) acrylic composition comprising a bio-renewable monomer |
| GB2622079A (en) | 2022-09-01 | 2024-03-06 | Henkel Ag & Co Kgaa | Anaerobically curable compositions |
| EP4567085A1 (en) | 2023-12-08 | 2025-06-11 | Henkel AG & Co. KGaA | Electrochemically debondable adhesive film |
| GB2638999A (en) | 2024-03-05 | 2025-09-10 | Henkel Ag & Co Kgaa | A dual curable composition |
Family Cites Families (9)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3043820A (en) * | 1960-10-14 | 1962-07-10 | Robert H Krieble | Anaerobic curing sealant composition having extended shelf stability |
| US3203941A (en) * | 1961-06-30 | 1965-08-31 | Loctite Corp | Accelerated anaerobic curing compositions containing a catalyst system of peroxides and polyamino compounds |
| US3297745A (en) * | 1962-04-05 | 1967-01-10 | Robertson Co H H | Ethylenically unsaturated di-and tetra-urethane monomers |
| US3218305A (en) * | 1963-12-26 | 1965-11-16 | Loctite Corp | Accelerated anaerobic compositions and method of using same |
| US3425988A (en) * | 1965-01-27 | 1969-02-04 | Loctite Corp | Polyurethane polyacrylate sealant compositions |
| US3532652A (en) * | 1966-07-14 | 1970-10-06 | Ppg Industries Inc | Polyisocyanate-acrylate polymer adhesives |
| US3491076A (en) * | 1967-08-08 | 1970-01-20 | Broadview Chem Corp | Accelerated sealant composition |
| US3591438A (en) * | 1968-03-04 | 1971-07-06 | Loctite Corp | Polymerizable acrylate composition and curing accelerator therefor |
| US3694415A (en) * | 1970-07-15 | 1972-09-26 | Kiyoshi Honda | Coating resinous composition |
-
1975
- 1975-05-23 US US05/580,267 patent/US4287330A/en not_active Expired - Lifetime
-
1976
- 1976-05-13 CA CA252,461A patent/CA1062846A/en not_active Expired
- 1976-05-21 FR FR7615436A patent/FR2311832A1/fr active Granted
- 1976-05-21 NL NLAANVRAGE7605439,A patent/NL188295C/xx not_active IP Right Cessation
- 1976-05-21 GB GB21046/76A patent/GB1546468A/en not_active Expired
- 1976-05-21 DE DE2622875A patent/DE2622875C2/de not_active Expired
- 1976-05-22 JP JP51059563A patent/JPS6031872B2/ja not_active Expired
- 1976-05-22 AU AU14116/76A patent/AU512342B2/en not_active Expired
- 1976-05-24 IT IT49623/76A patent/IT1069275B/it active
Non-Patent Citations (1)
| Title |
|---|
| NICHTS-ERMITTELT |
Also Published As
| Publication number | Publication date |
|---|---|
| IT1069275B (it) | 1985-03-25 |
| US4287330A (en) | 1981-09-01 |
| FR2311832B1 (en:Method) | 1980-02-15 |
| DE2622875A1 (de) | 1976-12-09 |
| NL188295B (nl) | 1991-12-16 |
| NL188295C (nl) | 1992-05-18 |
| FR2311832A1 (fr) | 1976-12-17 |
| AU512342B2 (en) | 1980-10-09 |
| AU1411676A (en) | 1977-11-24 |
| CA1062846A (en) | 1979-09-18 |
| JPS51144438A (en) | 1976-12-11 |
| GB1546468A (en) | 1979-05-23 |
| NL7605439A (nl) | 1976-11-25 |
| JPS6031872B2 (ja) | 1985-07-24 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8110 | Request for examination paragraph 44 | ||
| D2 | Grant after examination | ||
| 8364 | No opposition during term of opposition |