DE69609616T2 - Initiatorsystem und daraus hergestellte klebstoffzusammensetzung - Google Patents
Initiatorsystem und daraus hergestellte klebstoffzusammensetzungInfo
- Publication number
- DE69609616T2 DE69609616T2 DE69609616T DE69609616T DE69609616T2 DE 69609616 T2 DE69609616 T2 DE 69609616T2 DE 69609616 T DE69609616 T DE 69609616T DE 69609616 T DE69609616 T DE 69609616T DE 69609616 T2 DE69609616 T2 DE 69609616T2
- Authority
- DE
- Germany
- Prior art keywords
- acrylic
- organoborane
- acrylic monomer
- polymerization
- amine
- 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 - Lifetime
Links
- 239000000203 mixture Substances 0.000 title claims description 89
- 239000003999 initiator Substances 0.000 title claims description 29
- 239000000853 adhesive Substances 0.000 title description 57
- 230000001070 adhesive effect Effects 0.000 title description 57
- 239000003795 chemical substances by application Substances 0.000 claims description 62
- NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims description 56
- 239000000178 monomer Substances 0.000 claims description 49
- -1 hydroxyl compound Chemical class 0.000 claims description 36
- 150000001412 amines Chemical class 0.000 claims description 32
- 238000006116 polymerization reaction Methods 0.000 claims description 32
- 239000002904 solvent Substances 0.000 claims description 27
- 125000000217 alkyl group Chemical group 0.000 claims description 23
- 229920000768 polyamine Polymers 0.000 claims description 19
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 14
- 239000000758 substrate Substances 0.000 claims description 13
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 11
- 230000000977 initiatory effect Effects 0.000 claims description 11
- 238000000034 method Methods 0.000 claims description 11
- 239000003522 acrylic cement Substances 0.000 claims description 8
- 239000007795 chemical reaction product Substances 0.000 claims description 8
- 238000002156 mixing Methods 0.000 claims description 7
- 239000005056 polyisocyanate Substances 0.000 claims description 7
- 229920001228 polyisocyanate Polymers 0.000 claims description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 125000004430 oxygen atom Chemical group O* 0.000 claims description 6
- 125000001309 chloro group Chemical group Cl* 0.000 claims description 4
- 239000003505 polymerization initiator Substances 0.000 claims description 4
- 229910052801 chlorine Inorganic materials 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- 239000002131 composite material Substances 0.000 claims 2
- 125000005395 methacrylic acid group Chemical group 0.000 claims 1
- 125000004432 carbon atom Chemical group C* 0.000 description 22
- 239000000463 material Substances 0.000 description 21
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 20
- 150000001875 compounds Chemical class 0.000 description 16
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 12
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 12
- 150000003254 radicals Chemical class 0.000 description 11
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 description 10
- 239000010408 film Substances 0.000 description 10
- 239000011521 glass Substances 0.000 description 10
- 239000007787 solid Substances 0.000 description 10
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 10
- 239000012190 activator Substances 0.000 description 9
- 125000003277 amino group Chemical group 0.000 description 9
- 239000000499 gel Substances 0.000 description 9
- 150000003141 primary amines Chemical class 0.000 description 9
- 239000000654 additive Substances 0.000 description 8
- 150000001408 amides Chemical class 0.000 description 8
- CQEYYJKEWSMYFG-UHFFFAOYSA-N butyl acrylate Chemical compound CCCCOC(=O)C=C CQEYYJKEWSMYFG-UHFFFAOYSA-N 0.000 description 8
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 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 8
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 7
- ZOXJGFHDIHLPTG-UHFFFAOYSA-N Boron Chemical group [B] ZOXJGFHDIHLPTG-UHFFFAOYSA-N 0.000 description 7
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 7
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- 150000001336 alkenes Chemical class 0.000 description 6
- 150000004985 diamines Chemical class 0.000 description 6
- XFNJVJPLKCPIBV-UHFFFAOYSA-N trimethylenediamine Chemical compound NCCCN XFNJVJPLKCPIBV-UHFFFAOYSA-N 0.000 description 6
- 229920002818 (Hydroxyethyl)methacrylate Polymers 0.000 description 5
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 5
- 239000005058 Isophorone diisocyanate Substances 0.000 description 5
- 239000004698 Polyethylene Substances 0.000 description 5
- 239000002313 adhesive film Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 229910052796 boron Inorganic materials 0.000 description 5
- 230000000052 comparative effect Effects 0.000 description 5
- 238000009472 formulation Methods 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 229920000573 polyethylene Polymers 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- 239000004810 polytetrafluoroethylene Substances 0.000 description 5
- 229920001343 polytetrafluoroethylene Polymers 0.000 description 5
- 239000011347 resin Substances 0.000 description 5
- 229920005989 resin Polymers 0.000 description 5
- 238000012360 testing method Methods 0.000 description 5
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 4
- NDWUBGAGUCISDV-UHFFFAOYSA-N 4-hydroxybutyl prop-2-enoate Chemical compound OCCCCOC(=O)C=C NDWUBGAGUCISDV-UHFFFAOYSA-N 0.000 description 4
- SOGAXMICEFXMKE-UHFFFAOYSA-N Butylmethacrylate Chemical compound CCCCOC(=O)C(C)=C SOGAXMICEFXMKE-UHFFFAOYSA-N 0.000 description 4
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 4
- 239000003054 catalyst Substances 0.000 description 4
- 239000003153 chemical reaction reagent Substances 0.000 description 4
- JQVDAXLFBXTEQA-UHFFFAOYSA-N dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 4
- 239000012975 dibutyltin dilaurate Substances 0.000 description 4
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 4
- 239000001257 hydrogen Substances 0.000 description 4
- 229910052739 hydrogen Inorganic materials 0.000 description 4
- 238000004519 manufacturing process Methods 0.000 description 4
- 229920005862 polyol Polymers 0.000 description 4
- 150000003077 polyols Chemical class 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 239000010409 thin film Substances 0.000 description 4
- AZYRZNIYJDKRHO-UHFFFAOYSA-N 1,3-bis(2-isocyanatopropan-2-yl)benzene Chemical compound O=C=NC(C)(C)C1=CC=CC(C(C)(C)N=C=O)=C1 AZYRZNIYJDKRHO-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 3
- 238000012644 addition polymerization Methods 0.000 description 3
- 230000000996 additive effect Effects 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 125000005250 alkyl acrylate group Chemical group 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- HUMNYLRZRPPJDN-UHFFFAOYSA-N benzaldehyde Chemical compound O=CC1=CC=CC=C1 HUMNYLRZRPPJDN-UHFFFAOYSA-N 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 239000011258 core-shell material Substances 0.000 description 3
- 125000004386 diacrylate group Chemical group 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 3
- 239000012948 isocyanate Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 229920006295 polythiol Polymers 0.000 description 3
- 150000003335 secondary amines Chemical class 0.000 description 3
- LALRXNPLTWZJIJ-UHFFFAOYSA-N triethylborane Chemical compound CCB(CC)CC LALRXNPLTWZJIJ-UHFFFAOYSA-N 0.000 description 3
- VOBUAPTXJKMNCT-UHFFFAOYSA-N 1-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound CCCCCC(OC(=O)C=C)OC(=O)C=C VOBUAPTXJKMNCT-UHFFFAOYSA-N 0.000 description 2
- XFCMNSHQOZQILR-UHFFFAOYSA-N 2-[2-(2-methylprop-2-enoyloxy)ethoxy]ethyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OCCOCCOC(=O)C(C)=C XFCMNSHQOZQILR-UHFFFAOYSA-N 0.000 description 2
- YXYJVFYWCLAXHO-UHFFFAOYSA-N 2-methoxyethyl 2-methylprop-2-enoate Chemical compound COCCOC(=O)C(C)=C YXYJVFYWCLAXHO-UHFFFAOYSA-N 0.000 description 2
- KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- NLZUEZXRPGMBCV-UHFFFAOYSA-N Butylhydroxytoluene Chemical compound CC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 NLZUEZXRPGMBCV-UHFFFAOYSA-N 0.000 description 2
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical compound CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 description 2
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 2
- BAPJBEWLBFYGME-UHFFFAOYSA-N Methyl acrylate Chemical compound COC(=O)C=C BAPJBEWLBFYGME-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical class O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- LCXXNKZQVOXMEH-UHFFFAOYSA-N Tetrahydrofurfuryl methacrylate Chemical compound CC(=C)C(=O)OCC1CCCO1 LCXXNKZQVOXMEH-UHFFFAOYSA-N 0.000 description 2
- 150000003926 acrylamides Chemical class 0.000 description 2
- 230000002411 adverse Effects 0.000 description 2
- 150000001299 aldehydes Chemical class 0.000 description 2
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- UORVGPXVDQYIDP-UHFFFAOYSA-N borane Chemical compound B UORVGPXVDQYIDP-UHFFFAOYSA-N 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- OIWOHHBRDFKZNC-UHFFFAOYSA-N cyclohexyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC1CCCCC1 OIWOHHBRDFKZNC-UHFFFAOYSA-N 0.000 description 2
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- SUPCQIBBMFXVTL-UHFFFAOYSA-N ethyl 2-methylprop-2-enoate Chemical compound CCOC(=O)C(C)=C SUPCQIBBMFXVTL-UHFFFAOYSA-N 0.000 description 2
- 229920000578 graft copolymer Polymers 0.000 description 2
- 229920002681 hypalon Polymers 0.000 description 2
- 150000002596 lactones Chemical class 0.000 description 2
- 125000005647 linker group Chemical group 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 239000001301 oxygen Substances 0.000 description 2
- 229910052760 oxygen Inorganic materials 0.000 description 2
- NWVVVBRKAWDGAB-UHFFFAOYSA-N p-methoxyphenol Chemical compound COC1=CC=C(O)C=C1 NWVVVBRKAWDGAB-UHFFFAOYSA-N 0.000 description 2
- PNJWIWWMYCMZRO-UHFFFAOYSA-N pent‐4‐en‐2‐one Natural products CC(=O)CC=C PNJWIWWMYCMZRO-UHFFFAOYSA-N 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001223 polyethylene glycol Polymers 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 2
- AZIQALWHRUQPHV-UHFFFAOYSA-N prop-2-eneperoxoic acid Chemical compound OOC(=O)C=C AZIQALWHRUQPHV-UHFFFAOYSA-N 0.000 description 2
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- 239000002562 thickening agent Substances 0.000 description 2
- PAPBSGBWRJIAAV-UHFFFAOYSA-N ε-Caprolactone Chemical compound O=C1CCCCCO1 PAPBSGBWRJIAAV-UHFFFAOYSA-N 0.000 description 2
- LGPAKRMZNPYPMG-UHFFFAOYSA-N (3-hydroxy-2-prop-2-enoyloxypropyl) prop-2-enoate Chemical compound C=CC(=O)OC(CO)COC(=O)C=C LGPAKRMZNPYPMG-UHFFFAOYSA-N 0.000 description 1
- PCHXZXKMYCGVFA-UHFFFAOYSA-N 1,3-diazetidine-2,4-dione Chemical compound O=C1NC(=O)N1 PCHXZXKMYCGVFA-UHFFFAOYSA-N 0.000 description 1
- 239000005059 1,4-Cyclohexyldiisocyanate Substances 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- SBJCUZQNHOLYMD-UHFFFAOYSA-N 1,5-Naphthalene diisocyanate Chemical compound C1=CC=C2C(N=C=O)=CC=CC2=C1N=C=O SBJCUZQNHOLYMD-UHFFFAOYSA-N 0.000 description 1
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 description 1
- IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 description 1
- YSFBEAASFUWWHU-UHFFFAOYSA-N 2,4-dichlorobenzaldehyde Chemical compound ClC1=CC=C(C=O)C(Cl)=C1 YSFBEAASFUWWHU-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 description 1
- KSJBMDCFYZKAFH-UHFFFAOYSA-N 2-(2-sulfanylethylsulfanyl)ethanethiol Chemical compound SCCSCCS KSJBMDCFYZKAFH-UHFFFAOYSA-N 0.000 description 1
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 description 1
- DPBJAVGHACCNRL-UHFFFAOYSA-N 2-(dimethylamino)ethyl prop-2-enoate Chemical compound CN(C)CCOC(=O)C=C DPBJAVGHACCNRL-UHFFFAOYSA-N 0.000 description 1
- GOXQRTZXKQZDDN-UHFFFAOYSA-N 2-Ethylhexyl acrylate Chemical compound CCCCC(CC)COC(=O)C=C GOXQRTZXKQZDDN-UHFFFAOYSA-N 0.000 description 1
- NHFHIOZDNXRYFF-UHFFFAOYSA-N 2-[2-(2-hydroxyethoxy)ethoxy]ethanol;prop-1-ene Chemical group CC=C.OCCOCCOCCO NHFHIOZDNXRYFF-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- HCZMHWVFVZAHCR-UHFFFAOYSA-N 2-[2-(2-sulfanylethoxy)ethoxy]ethanethiol Chemical compound SCCOCCOCCS HCZMHWVFVZAHCR-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
- AEPWOCLBLLCOGZ-UHFFFAOYSA-N 2-cyanoethyl prop-2-enoate Chemical compound C=CC(=O)OCCC#N AEPWOCLBLLCOGZ-UHFFFAOYSA-N 0.000 description 1
- WDQMWEYDKDCEHT-UHFFFAOYSA-N 2-ethylhexyl 2-methylprop-2-enoate Chemical compound CCCCC(CC)COC(=O)C(C)=C WDQMWEYDKDCEHT-UHFFFAOYSA-N 0.000 description 1
- VAYMIYBJLRRIFR-UHFFFAOYSA-N 2-tolyl isocyanate Chemical compound CC1=CC=CC=C1N=C=O VAYMIYBJLRRIFR-UHFFFAOYSA-N 0.000 description 1
- JCEZOHLWDIONSP-UHFFFAOYSA-N 3-[2-[2-(3-aminopropoxy)ethoxy]ethoxy]propan-1-amine Chemical compound NCCCOCCOCCOCCCN JCEZOHLWDIONSP-UHFFFAOYSA-N 0.000 description 1
- JVUAYVUZADWJBK-UHFFFAOYSA-N 3-cyanopropyl prop-2-enoate Chemical compound C=CC(=O)OCCCC#N JVUAYVUZADWJBK-UHFFFAOYSA-N 0.000 description 1
- XDLMVUHYZWKMMD-UHFFFAOYSA-N 3-trimethoxysilylpropyl 2-methylprop-2-enoate Chemical compound CO[Si](OC)(OC)CCCOC(=O)C(C)=C XDLMVUHYZWKMMD-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
- ZEYHEAKUIGZSGI-UHFFFAOYSA-N 4-methoxybenzoic acid Chemical compound COC1=CC=C(C(O)=O)C=C1 ZEYHEAKUIGZSGI-UHFFFAOYSA-N 0.000 description 1
- BXRFQSNOROATLV-UHFFFAOYSA-N 4-nitrobenzaldehyde Chemical compound [O-][N+](=O)C1=CC=C(C=O)C=C1 BXRFQSNOROATLV-UHFFFAOYSA-N 0.000 description 1
- YYROPELSRYBVMQ-UHFFFAOYSA-N 4-toluenesulfonyl chloride Chemical compound CC1=CC=C(S(Cl)(=O)=O)C=C1 YYROPELSRYBVMQ-UHFFFAOYSA-N 0.000 description 1
- HRPVXLWXLXDGHG-UHFFFAOYSA-N Acrylamide Chemical compound NC(=O)C=C HRPVXLWXLXDGHG-UHFFFAOYSA-N 0.000 description 1
- 239000005711 Benzoic acid Substances 0.000 description 1
- 239000004322 Butylated hydroxytoluene Substances 0.000 description 1
- YNDZLBYYUYXQED-UHFFFAOYSA-N CC=C.C(COCCO)O Chemical group CC=C.C(COCCO)O YNDZLBYYUYXQED-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- OQSSNGKVNWXYOE-UHFFFAOYSA-N N=C=O.N=C=O.CCC(C)CC(C)(C)C Chemical compound N=C=O.N=C=O.CCC(C)CC(C)(C)C OQSSNGKVNWXYOE-UHFFFAOYSA-N 0.000 description 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 description 1
- 101150020251 NR13 gene Proteins 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000002202 Polyethylene glycol Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004743 Polypropylene Substances 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- OKKRPWIIYQTPQF-UHFFFAOYSA-N Trimethylolpropane trimethacrylate Chemical compound CC(=C)C(=O)OCC(CC)(COC(=O)C(C)=C)COC(=O)C(C)=C OKKRPWIIYQTPQF-UHFFFAOYSA-N 0.000 description 1
- 239000004699 Ultra-high molecular weight polyethylene Substances 0.000 description 1
- IAXXETNIOYFMLW-COPLHBTASA-N [(1s,3s,4s)-4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl] 2-methylprop-2-enoate Chemical compound C1C[C@]2(C)[C@@H](OC(=O)C(=C)C)C[C@H]1C2(C)C IAXXETNIOYFMLW-COPLHBTASA-N 0.000 description 1
- HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- KXBFLNPZHXDQLV-UHFFFAOYSA-N [cyclohexyl(diisocyanato)methyl]cyclohexane Chemical compound C1CCCCC1C(N=C=O)(N=C=O)C1CCCCC1 KXBFLNPZHXDQLV-UHFFFAOYSA-N 0.000 description 1
- WETWJCDKMRHUPV-UHFFFAOYSA-N acetyl chloride Chemical compound CC(Cl)=O WETWJCDKMRHUPV-UHFFFAOYSA-N 0.000 description 1
- 239000012346 acetyl chloride Substances 0.000 description 1
- XECAHXYUAAWDEL-UHFFFAOYSA-N acrylonitrile butadiene styrene Chemical compound C=CC=C.C=CC#N.C=CC1=CC=CC=C1 XECAHXYUAAWDEL-UHFFFAOYSA-N 0.000 description 1
- 239000004676 acrylonitrile butadiene styrene Substances 0.000 description 1
- 229920000122 acrylonitrile butadiene styrene Polymers 0.000 description 1
- 238000007259 addition reaction Methods 0.000 description 1
- PWAXUOGZOSVGBO-UHFFFAOYSA-N adipoyl chloride Chemical compound ClC(=O)CCCCC(Cl)=O PWAXUOGZOSVGBO-UHFFFAOYSA-N 0.000 description 1
- 125000003342 alkenyl group Chemical group 0.000 description 1
- 150000003973 alkyl amines Chemical class 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 150000005840 aryl radicals Chemical group 0.000 description 1
- 239000012298 atmosphere Substances 0.000 description 1
- CSKNSYBAZOQPLR-UHFFFAOYSA-N benzenesulfonyl chloride Chemical compound ClS(=O)(=O)C1=CC=CC=C1 CSKNSYBAZOQPLR-UHFFFAOYSA-N 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- OHJMTUPIZMNBFR-UHFFFAOYSA-N biuret Chemical compound NC(=O)NC(N)=O OHJMTUPIZMNBFR-UHFFFAOYSA-N 0.000 description 1
- 238000006664 bond formation reaction Methods 0.000 description 1
- 229910000085 borane Inorganic materials 0.000 description 1
- 230000005587 bubbling Effects 0.000 description 1
- QDHFHIQKOVNCNC-UHFFFAOYSA-N butane-1-sulfonic acid Chemical compound CCCCS(O)(=O)=O QDHFHIQKOVNCNC-UHFFFAOYSA-N 0.000 description 1
- 235000010354 butylated hydroxytoluene Nutrition 0.000 description 1
- 229940095259 butylated hydroxytoluene Drugs 0.000 description 1
- 150000001718 carbodiimides Chemical class 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 239000000919 ceramic Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 239000008139 complexing agent Substances 0.000 description 1
- 239000004567 concrete Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000012937 correction Methods 0.000 description 1
- 125000004093 cyano group Chemical group *C#N 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- GTBGXKPAKVYEKJ-UHFFFAOYSA-N decyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCOC(=O)C(C)=C GTBGXKPAKVYEKJ-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- GMSCBRSQMRDRCD-UHFFFAOYSA-N dodecyl 2-methylprop-2-enoate Chemical compound CCCCCCCCCCCCOC(=O)C(C)=C GMSCBRSQMRDRCD-UHFFFAOYSA-N 0.000 description 1
- 239000013536 elastomeric material Substances 0.000 description 1
- 239000008393 encapsulating agent Substances 0.000 description 1
- 150000002148 esters Chemical class 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
- 238000000605 extraction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000011491 glass wool Substances 0.000 description 1
- 235000011187 glycerol Nutrition 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000001746 injection moulding Methods 0.000 description 1
- 229940119545 isobornyl methacrylate Drugs 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 125000001261 isocyanato group Chemical group *N=C=O 0.000 description 1
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000011159 matrix material Substances 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
- QARBMVPHQWIHKH-UHFFFAOYSA-N methanesulfonyl chloride Chemical compound CS(Cl)(=O)=O QARBMVPHQWIHKH-UHFFFAOYSA-N 0.000 description 1
- 238000013508 migration Methods 0.000 description 1
- 230000005012 migration Effects 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- 239000002808 molecular sieve Substances 0.000 description 1
- QRWZCJXEAOZAAW-UHFFFAOYSA-N n,n,2-trimethylprop-2-enamide Chemical compound CN(C)C(=O)C(C)=C QRWZCJXEAOZAAW-UHFFFAOYSA-N 0.000 description 1
- YRDNVESFWXDNSI-UHFFFAOYSA-N n-(2,4,4-trimethylpentan-2-yl)prop-2-enamide Chemical compound CC(C)(C)CC(C)(C)NC(=O)C=C YRDNVESFWXDNSI-UHFFFAOYSA-N 0.000 description 1
- OMNKZBIFPJNNIO-UHFFFAOYSA-N n-(2-methyl-4-oxopentan-2-yl)prop-2-enamide Chemical compound CC(=O)CC(C)(C)NC(=O)C=C OMNKZBIFPJNNIO-UHFFFAOYSA-N 0.000 description 1
- SNPAMTGUOWHTMN-UHFFFAOYSA-N n-decyl-2-methylprop-2-enamide Chemical compound CCCCCCCCCCNC(=O)C(C)=C SNPAMTGUOWHTMN-UHFFFAOYSA-N 0.000 description 1
- YPHQUSNPXDGUHL-UHFFFAOYSA-N n-methylprop-2-enamide Chemical compound CNC(=O)C=C YPHQUSNPXDGUHL-UHFFFAOYSA-N 0.000 description 1
- XFHJDMUEHUHAJW-UHFFFAOYSA-N n-tert-butylprop-2-enamide Chemical compound CC(C)(C)NC(=O)C=C XFHJDMUEHUHAJW-UHFFFAOYSA-N 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- ANISOHQJBAQUQP-UHFFFAOYSA-N octyl prop-2-enoate Chemical compound CCCCCCCCOC(=O)C=C ANISOHQJBAQUQP-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 150000007524 organic acids Chemical class 0.000 description 1
- 235000005985 organic acids Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- RPQRDASANLAFCM-UHFFFAOYSA-N oxiran-2-ylmethyl prop-2-enoate Chemical compound C=CC(=O)OCC1CO1 RPQRDASANLAFCM-UHFFFAOYSA-N 0.000 description 1
- 150000002924 oxiranes Chemical class 0.000 description 1
- WWFIYJKRQSPBLK-UHFFFAOYSA-N oxolan-2-ylmethyl 2-chloroprop-2-enoate Chemical compound ClC(=C)C(=O)OCC1CCCO1 WWFIYJKRQSPBLK-UHFFFAOYSA-N 0.000 description 1
- FXLOVSHXALFLKQ-UHFFFAOYSA-N p-tolualdehyde Chemical compound CC1=CC=C(C=O)C=C1 FXLOVSHXALFLKQ-UHFFFAOYSA-N 0.000 description 1
- 239000003973 paint Substances 0.000 description 1
- QNGNSVIICDLXHT-UHFFFAOYSA-N para-ethylbenzaldehyde Natural products CCC1=CC=C(C=O)C=C1 QNGNSVIICDLXHT-UHFFFAOYSA-N 0.000 description 1
- 239000002245 particle Substances 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 150000002978 peroxides Chemical class 0.000 description 1
- 150000002989 phenols Chemical class 0.000 description 1
- 235000011007 phosphoric acid Nutrition 0.000 description 1
- DOIRQSBPFJWKBE-UHFFFAOYSA-N phthalic acid di-n-butyl ester Natural products CCCCOC(=O)C1=CC=CC=C1C(=O)OCCCC DOIRQSBPFJWKBE-UHFFFAOYSA-N 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 239000004926 polymethyl methacrylate Substances 0.000 description 1
- 229920001155 polypropylene Polymers 0.000 description 1
- 238000004382 potting Methods 0.000 description 1
- 230000002028 premature Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- ZJLMKPKYJBQJNH-UHFFFAOYSA-N propane-1,3-dithiol Chemical compound SCCCS ZJLMKPKYJBQJNH-UHFFFAOYSA-N 0.000 description 1
- 238000010526 radical polymerization reaction Methods 0.000 description 1
- 239000000376 reactant Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007665 sagging Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 150000004756 silanes Chemical class 0.000 description 1
- 239000002002 slurry Substances 0.000 description 1
- URGAHOPLAPQHLN-UHFFFAOYSA-N sodium aluminosilicate Chemical compound [Na+].[Al+3].[O-][Si]([O-])=O.[O-][Si]([O-])=O URGAHOPLAPQHLN-UHFFFAOYSA-N 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 125000005504 styryl group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- LXEJRKJRKIFVNY-UHFFFAOYSA-N terephthaloyl chloride Chemical compound ClC(=O)C1=CC=C(C(Cl)=O)C=C1 LXEJRKJRKIFVNY-UHFFFAOYSA-N 0.000 description 1
- SJMYWORNLPSJQO-UHFFFAOYSA-N tert-butyl 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OC(C)(C)C SJMYWORNLPSJQO-UHFFFAOYSA-N 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- UWHCKJMYHZGTIT-UHFFFAOYSA-N tetraethylene glycol Chemical compound OCCOCCOCCOCCO UWHCKJMYHZGTIT-UHFFFAOYSA-N 0.000 description 1
- RUELTTOHQODFPA-UHFFFAOYSA-N toluene 2,6-diisocyanate Chemical compound CC1=C(N=C=O)C=CC=C1N=C=O RUELTTOHQODFPA-UHFFFAOYSA-N 0.000 description 1
- 238000001721 transfer moulding Methods 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
- 229920000785 ultra high molecular weight polyethylene Polymers 0.000 description 1
- MWOOGOJBHIARFG-UHFFFAOYSA-N vanillin Chemical compound COC1=CC(C=O)=CC=C1O MWOOGOJBHIARFG-UHFFFAOYSA-N 0.000 description 1
- FGQOOHJZONJGDT-UHFFFAOYSA-N vanillin Natural products COC1=CC(O)=CC(C=O)=C1 FGQOOHJZONJGDT-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000002023 wood Substances 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
- C08F4/00—Polymerisation catalysts
- C08F4/42—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors
- C08F4/44—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides
- C08F4/52—Metals; Metal hydrides; Metallo-organic compounds; Use thereof as catalyst precursors selected from light metals, zinc, cadmium, mercury, copper, silver, gold, boron, gallium, indium, thallium, rare earths or actinides selected from boron, aluminium, gallium, indium, thallium or rare earths
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
- C08F220/10—Esters
-
- 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)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
- Laminated Bodies (AREA)
- Polymerization Catalysts (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US51518795A | 1995-08-11 | 1995-08-11 | |
| PCT/US1996/010341 WO1997007171A1 (en) | 1995-08-11 | 1996-06-13 | Initiator system and adhesive composition made therewith |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69609616D1 DE69609616D1 (de) | 2000-09-07 |
| DE69609616T2 true DE69609616T2 (de) | 2001-04-12 |
Family
ID=24050306
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69609616T Expired - Lifetime DE69609616T2 (de) | 1995-08-11 | 1996-06-13 | Initiatorsystem und daraus hergestellte klebstoffzusammensetzung |
Country Status (9)
| Country | Link |
|---|---|
| US (2) | US5872197A (enExample) |
| EP (1) | EP0843708B1 (enExample) |
| JP (1) | JPH11512123A (enExample) |
| CN (1) | CN1089104C (enExample) |
| AU (1) | AU6177796A (enExample) |
| BR (1) | BR9609934A (enExample) |
| CA (1) | CA2229134A1 (enExample) |
| DE (1) | DE69609616T2 (enExample) |
| WO (1) | WO1997007171A1 (enExample) |
Families Citing this family (52)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5690780A (en) | 1995-02-22 | 1997-11-25 | Minnesota Mining And Manufacturing Company | Polymerizable compositions made with polymerization initiator systems based on organoborane amine complexes |
| US6383655B1 (en) | 1998-06-12 | 2002-05-07 | 3M Innovative Properties Company | Low odor polymerizable compositions useful for bonding low surface energy substrates |
| US6812308B2 (en) | 2000-11-21 | 2004-11-02 | 3M Innovative Properties Company | Initiator systems and adhesive compositions made therewith |
| US20020022588A1 (en) * | 1998-06-23 | 2002-02-21 | James Wilkie | Methods and compositions for sealing tissue leaks |
| US6799966B1 (en) | 1999-03-04 | 2004-10-05 | 3M Innovative Properties Company | Fluoropolymeric orthodontic article |
| US6252023B1 (en) | 1999-03-19 | 2001-06-26 | 3M Innovative Properties Company | Organoborane amine complex inatator systems and polymerizable compositions made therewith |
| DE19919581A1 (de) * | 1999-04-29 | 2000-11-02 | Espe Dental Ag | Dentalmaterialien, Verfahren zu ihrer Aushärtung und deren Verwendung |
| DE19925385A1 (de) * | 1999-06-02 | 2000-12-07 | Oxeno Olefinchemie Gmbh | Verfahren zur katalytischen Durchführung von Mehrphasenreaktionen, insbesondere Vinylierungen von Carbonsäuren |
| US6486090B1 (en) | 1999-11-04 | 2002-11-26 | 3M Innovative Properties Company | Initiator/hydroxide and initiator/alkoxide complexes, systems comprising the complexes, and polymerized compositions made therewith |
| US6410667B1 (en) | 1999-11-04 | 2002-06-25 | 3M Innovative Properties Company | Initiator/amidine complexes, systems comprising the complexes, and polymerized compositions made therewith |
| US6806330B1 (en) | 1999-12-17 | 2004-10-19 | Dow Global Technologies Inc. | Amine organoborane complex polymerization initiators and polymerizable compositions |
| US6479602B1 (en) | 2000-03-15 | 2002-11-12 | 3M Innovative Properties | Polymerization initiator systems and bonding compositions comprising vinyl aromatic compounds |
| EP1201722A1 (en) | 2000-10-23 | 2002-05-02 | Loctite (R & D) Limited | Polymerisation initiators, polymerisable compositions, and uses thereof |
| US6740716B2 (en) | 2001-10-30 | 2004-05-25 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
| US6849569B2 (en) | 2001-12-31 | 2005-02-01 | 3M Innovative Properties Company | Initiator systems comprising β-ketone compounds |
| US6762260B2 (en) | 2002-03-05 | 2004-07-13 | Dow Global Technologies Inc. | Organoborane amine complex polymerization initiators and polymerizable compositions |
| US6632908B1 (en) | 2002-03-12 | 2003-10-14 | Henkel Loctite Corporation | Bonding system having adherence to low energy surfaces |
| AU2003225512A1 (en) * | 2002-04-19 | 2003-11-03 | Loctite (R And D) Limited | Polymerisation initiators based on ammonium tetraalkyl boranes, polymerisable compositions, and uses thereof for bonding low surface energy substrates |
| US7098279B2 (en) * | 2002-10-22 | 2006-08-29 | Loctite (R&D) Limited | Non-flammable and non-combustible adhesive bonding systems having adherence to low energy surfaces |
| US6777512B1 (en) | 2003-02-28 | 2004-08-17 | Dow Global Technologies Inc. | Amine organoborane complex initiated polymerizable compositions containing siloxane polymerizable components |
| EP1648944A1 (en) | 2003-06-09 | 2006-04-26 | The Dow Global Technologies Inc. | Stabilized organoborane polymerization initiators and polymerizable compositions |
| US20040259990A1 (en) * | 2003-06-18 | 2004-12-23 | Sonnenschein Mark F. | Paint formulation for a low surface energy substrate |
| WO2005017005A1 (en) * | 2003-08-13 | 2005-02-24 | Dow Global Technologies Inc. | Method for joining substrates and objects |
| CN1835992B (zh) | 2003-08-13 | 2010-10-06 | 陶氏环球技术公司 | 使基材与物体接合的方法 |
| WO2005019365A2 (en) | 2003-08-20 | 2005-03-03 | Koninklijke Philips Electronics N.V. | Non-leaching adhesive system and its use in a liquid immersion objective |
| GB0326286D0 (en) | 2003-11-11 | 2003-12-17 | Vantico Gmbh | Initiator systems for polymerisable compositions |
| WO2005063480A1 (en) * | 2003-12-22 | 2005-07-14 | Dow Global Technologies Inc. | Accelerated organoborane amine complex initiated polymerizable compositions |
| US8501886B2 (en) * | 2003-12-22 | 2013-08-06 | Dow Global Technologies Llc | Accelerated organoborane amine complex initiated polymerizable compositions |
| US8202932B2 (en) * | 2004-12-03 | 2012-06-19 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| JP5039567B2 (ja) | 2005-02-16 | 2012-10-03 | ダウ・コーニング・コーポレイション | ポリマー粒子、および、有機ボランアミン錯体を用いた封入（ｅｎｃａｐｓｕｌａｔｅｄ）組成物 |
| US7408012B1 (en) | 2005-04-18 | 2008-08-05 | Loctite (R&D) Limited | Adhesive bonding systems having adherence to low energy surfaces |
| CN101267949A (zh) * | 2005-09-21 | 2008-09-17 | 陶氏康宁公司 | 使用有机基硼烷胺络合物的环境平版印刷方法 |
| CN101501043A (zh) | 2005-10-07 | 2009-08-05 | 陶氏环球技术公司 | 酰胺-有机硼酸酯引发剂体系 |
| US7682663B2 (en) * | 2006-02-23 | 2010-03-23 | Bowling Green State University | Remote curing of polymer coating by gaseous, vaporous or aerosol initiating agent |
| US20080103274A1 (en) * | 2006-10-12 | 2008-05-01 | Jialanella Gary L | Accelerated organoborane initiated polymerizable compositions |
| US7524907B2 (en) * | 2006-10-12 | 2009-04-28 | Dow Global Technologies, Inc. | Accelerated organoborane initiated polymerizable compositions |
| US20140262189A1 (en) * | 2008-01-25 | 2014-09-18 | Henkel US IP LLC | Curable compositions and fluid connections made therewith |
| US8742050B2 (en) | 2008-03-28 | 2014-06-03 | Henkel US IP LLC | Two part hybrid adhesive |
| US10052853B2 (en) | 2009-12-09 | 2018-08-21 | Lifeport, Inc. | Durable polymeric panels and devices exhibiting antiballistic capacity made therefrom |
| RU2537130C2 (ru) * | 2009-11-20 | 2014-12-27 | Митсуи Кемикалс, Инк. | Композиция для восстановления твердой ткани |
| CN104870573A (zh) | 2012-12-20 | 2015-08-26 | 3M创新有限公司 | 三有机硼烷-氨基官能化纳米粒子、组合物和方法 |
| EP3013868B1 (en) | 2013-06-28 | 2017-10-18 | 3M Innovative Properties Company | Acid-modified nanoparticles, dual part polymerizable compositions, and methods |
| WO2015081068A1 (en) | 2013-11-26 | 2015-06-04 | Basf Se | Polyurethane elastomeric composition and method of preparing the same |
| JP6694823B2 (ja) * | 2014-03-27 | 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 | 有機ホウ素を含む組成物、及びその使用方法 |
| JP2017149789A (ja) * | 2014-07-03 | 2017-08-31 | 株式会社イーテック | ２液混合型接着剤 |
| EP3183311A1 (en) | 2014-08-18 | 2017-06-28 | LORD Corporation | Method for low temperature bonding of elastomers |
| CN108602320B (zh) * | 2016-01-15 | 2021-01-12 | 巴斯夫欧洲公司 | 复合制品 |
| US11274233B2 (en) | 2016-08-09 | 2022-03-15 | Emulsion Technology Co., Ltd. | Two-component adhesive |
| EP3556804A4 (en) | 2016-12-16 | 2019-11-13 | Denka Company Limited | COMPOSITION |
| WO2019116201A1 (en) | 2017-12-13 | 2019-06-20 | 3M Innovative Properties Company | Optically clear adhesives containing a trialkyl borane complex initiator and photoacid |
| US20220025232A1 (en) | 2018-11-27 | 2022-01-27 | Emulsion Technology Co., Ltd. | Two-component adhesive |
| FR3098818B1 (fr) * | 2019-07-18 | 2021-06-25 | Bostik Sa | Composition adhésive bi-composante comprenant un complexe organoborane-amine |
Family Cites Families (53)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CA664459A (en) * | 1963-06-04 | Jennes Gert | Process for the polymerisation of unsaturated compounds | |
| US2985633A (en) * | 1958-10-30 | 1961-05-23 | Union Carbide Corp | Polymerization of ethylene with organoboron compounds treated with oxygen |
| US3275611A (en) * | 1960-12-30 | 1966-09-27 | Monsanto Co | Process for polymerizing unsaturated monomers with a catalyst comprising an organoboron compound, a peroxygen compound and an amine |
| US3340193A (en) * | 1960-12-30 | 1967-09-05 | Monsanto Co | Mineral oil containing alkyl polymethacrylate antifoamant |
| US3141862A (en) * | 1961-03-01 | 1964-07-21 | Exxon Research Engineering Co | Graft copolymerization using boron alkyls in the presence of oxygen as catalysts |
| BE602558A (enExample) * | 1961-03-14 | |||
| US3257360A (en) * | 1961-07-27 | 1966-06-21 | Monsanto Co | Terpolymers and processes for making same |
| US3306809A (en) * | 1961-08-21 | 1967-02-28 | Union Carbide Corp | Curable polyepoxide and glycol polyamine compositions |
| GB1113722A (en) * | 1964-05-21 | 1968-05-15 | Minnesota Mining & Mfg | Aerobically polymerisable compositions |
| BE674405A (enExample) * | 1965-01-06 | 1966-06-28 | ||
| US3425988A (en) * | 1965-01-27 | 1969-02-04 | Loctite Corp | Polyurethane polyacrylate sealant compositions |
| JPS4214318Y1 (enExample) * | 1965-02-26 | 1967-08-15 | ||
| BE524840A (enExample) * | 1965-12-17 | |||
| US3418260A (en) * | 1966-01-20 | 1968-12-24 | Du Pont | Imidazole-borane polymers |
| JPS4529195Y1 (enExample) * | 1967-04-13 | 1970-11-10 | ||
| US3527737A (en) * | 1967-09-15 | 1970-09-08 | G C Kagaku Kogyo Kk | Adhesive compositions |
| JPS4616888Y1 (enExample) * | 1968-02-15 | 1971-06-12 | ||
| JPS4818928B1 (enExample) * | 1969-12-13 | 1973-06-09 | ||
| JPS5137092B2 (enExample) * | 1972-04-28 | 1976-10-13 | ||
| JPS53102394A (en) * | 1977-02-18 | 1978-09-06 | Hitachi Ltd | Two-pack type resin composition |
| US4167616A (en) * | 1977-08-22 | 1979-09-11 | Rohm And Haas Company | Polymerization with diborane adducts or oligomers of boron-containing monomers |
| DE3041904C2 (de) * | 1980-11-06 | 1984-11-22 | Henkel KGaA, 4000 Düsseldorf | Borverbindungen enthaltende lagerstabile Reaktionsklebstoffe |
| DE3207263A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Organo-borverbindungen enthaltende stoffgemische, verfahren zu ihrer herstellung und ihre verwendung |
| DE3201731A1 (de) * | 1982-01-21 | 1983-07-28 | Henkel KGaA, 4000 Düsseldorf | "aerob haertende kunststoffmassen" |
| DE3201780A1 (de) * | 1982-01-21 | 1983-08-25 | Henkel KGaA, 4000 Düsseldorf | Neue polymere organo-borverbindungen und ihre verwendung |
| US4379728A (en) * | 1982-02-04 | 1983-04-12 | W. R. Grace & Co. | Cyanourea compounds or polymers thereof as epoxy resin curing agents |
| DE3207264A1 (de) * | 1982-03-01 | 1983-09-08 | Henkel KGaA, 4000 Düsseldorf | Neue boralkylverbindungen, verfahren zu ihrer herstellung und ihre verwendung |
| US4524181A (en) * | 1983-08-11 | 1985-06-18 | Minnesota Mining And Manufacturing Company | Curable epoxy compositions and cured resins obtained therefrom |
| US4485229A (en) * | 1984-02-15 | 1984-11-27 | Texaco Inc. | Epoxy resin containing a combination of high and low molecular weight polyoxyalkylene polyamine curing agents |
| US4731416A (en) * | 1984-10-01 | 1988-03-15 | The Dow Chemical Company | Polyurethane-type adhesives containing nonaqueous solutions of acrylate polymers |
| DE3518965A1 (de) * | 1985-05-25 | 1986-11-27 | Henkel KGaA, 40589 Düsseldorf | Schmelzbare und dabei aerob aushaertende kunststoffmassen und verfahren zu ihrer herstellung |
| US4874814A (en) * | 1985-07-02 | 1989-10-17 | Monsanto Company | Cross-linked polyvinyl butyral |
| US4656229A (en) * | 1985-12-02 | 1987-04-07 | National Starch And Chemical Corporation | Anaerobic adhesive compositions |
| US4684538A (en) * | 1986-02-21 | 1987-08-04 | Loctite Corporation | Polysiloxane urethane compounds and adhesive compositions, and method of making and using the same |
| US5021507A (en) * | 1986-05-05 | 1991-06-04 | National Starch And Chemical Investment Holding Corporation | Arcylic modified reactive urethane hot melt adhesive compositions |
| JP2528098B2 (ja) * | 1986-06-06 | 1996-08-28 | 三井石油化学工業株式会社 | セラミックス用接着剤 |
| US4904360A (en) * | 1986-09-12 | 1990-02-27 | Minnesota Mining And Manufacturing Company | Water-compatible coating composition |
| CA1292591C (en) * | 1986-10-30 | 1991-11-26 | Takeshi Sakashita | Curable composition |
| US4721751A (en) * | 1987-03-26 | 1988-01-26 | Ppg Industries, Inc. | Polyurea-polyurethane acrylate dispersions |
| JPH075680B2 (ja) * | 1987-07-03 | 1995-01-25 | 三井石油化学工業株式会社 | 硬化性組成物 |
| US4775734A (en) * | 1987-08-12 | 1988-10-04 | Ashland Oil, Inc. | Non-nucleophilic acid salts of amines as cure accelerators |
| JP2811839B2 (ja) * | 1989-12-06 | 1998-10-15 | 三井化学株式会社 | 歯科用チタンまたはその合金用硬化性接着剤組成物 |
| JP2812527B2 (ja) * | 1990-03-15 | 1998-10-22 | 三井化学株式会社 | 歯科接着剤用触媒ペースト状組成物 |
| US5106928A (en) * | 1991-04-29 | 1992-04-21 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5143884A (en) * | 1991-04-29 | 1992-09-01 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| JPH05235089A (ja) * | 1992-02-26 | 1993-09-10 | Fujitsu Ltd | フェイスダウン実装用半導体チップ |
| US5286821A (en) * | 1992-03-17 | 1994-02-15 | National Starch And Chemical Investment Holding Corporation | Acrylic adhesive composition and organoboron initiator system |
| US5401805A (en) * | 1992-04-06 | 1995-03-28 | The Penn State Research Foundation | Olefin graft copolymers prepared using borane-containing olefin backbone polymers |
| US5310835A (en) * | 1993-09-30 | 1994-05-10 | National Starch And Chemical Investment Holding Corporation | Transparent two-part acrylic adhesive composition and the method of use thereof |
| CN1054136C (zh) * | 1994-02-22 | 2000-07-05 | 美国3M公司 | 可聚合的丙烯酸组合物和将两个基材粘合在一起的方法 |
| US5621143A (en) * | 1995-04-14 | 1997-04-15 | Minnesota Mining And Manufacturing Company | Organoborane polyoxyalkylenepolyamine complexes and adhesive compositions made therewith |
| US5616796A (en) * | 1995-04-14 | 1997-04-01 | Minnesota Mining And Manufacturing Company | Organoborane polyamine complexes and adhesive composition made therewith |
| CN1106411C (zh) * | 1995-11-07 | 2003-04-23 | 美国3M公司 | 引发剂系统和由其制成的粘合剂组合物 |
-
1996
- 1996-06-13 JP JP9509256A patent/JPH11512123A/ja not_active Withdrawn
- 1996-06-13 AU AU61777/96A patent/AU6177796A/en not_active Abandoned
- 1996-06-13 DE DE69609616T patent/DE69609616T2/de not_active Expired - Lifetime
- 1996-06-13 BR BR9609934A patent/BR9609934A/pt not_active IP Right Cessation
- 1996-06-13 CA CA002229134A patent/CA2229134A1/en not_active Abandoned
- 1996-06-13 WO PCT/US1996/010341 patent/WO1997007171A1/en not_active Ceased
- 1996-06-13 CN CN96196178.3A patent/CN1089104C/zh not_active Expired - Fee Related
- 1996-06-13 EP EP96919431A patent/EP0843708B1/en not_active Expired - Lifetime
-
1997
- 1997-06-23 US US08/880,317 patent/US5872197A/en not_active Expired - Fee Related
- 1997-10-07 US US08/947,729 patent/US5990036A/en not_active Expired - Lifetime
Also Published As
| Publication number | Publication date |
|---|---|
| CA2229134A1 (en) | 1997-02-27 |
| CN1192769A (zh) | 1998-09-09 |
| DE69609616D1 (de) | 2000-09-07 |
| WO1997007171A1 (en) | 1997-02-27 |
| EP0843708B1 (en) | 2000-08-02 |
| BR9609934A (pt) | 1999-06-08 |
| AU6177796A (en) | 1997-03-12 |
| MX9800918A (es) | 1998-05-31 |
| US5990036A (en) | 1999-11-23 |
| JPH11512123A (ja) | 1999-10-19 |
| US5872197A (en) | 1999-02-16 |
| EP0843708A1 (en) | 1998-05-27 |
| CN1089104C (zh) | 2002-08-14 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69609616T2 (de) | Initiatorsystem und daraus hergestellte klebstoffzusammensetzung | |
| DE69613387T2 (de) | Initiator system und klebstoff zusammensetzung diesen enthaltend | |
| DE69607953T2 (de) | Organoboran-polyoxyalkylenpolyamin-komplexe und damit hergestellte klebstoffzusammensetzungen | |
| DE69220216T2 (de) | Durch strahlung härtbare druckempfindliche klebemittelzusammensetzung auf basis von acrylaten und syloxanen | |
| DE69613378T2 (de) | Organoboran-polyamin-komplex initiator systeme sowie damit hergestellte polymerisierbare zusammensetzungen | |
| DE69716630T2 (de) | Organoboran-aminkomplex initiatorsysteme und daraus hergestellte polymerisierbare zusammensetzungen | |
| DE60112255T2 (de) | Polymerisationsinitiator-systeme und haftzusammensetzungen, die vinylaromatische verbindungen enthalten | |
| DE60010761T2 (de) | Initiator/amidine komplexe, solche komplexe enthaltende systeme, und damit hergestellte polymerisierte zusammensetzungen | |
| DE69710910T2 (de) | Durch feuchtigkeit härtbare schmelzklebstoff-zusammensetzung | |
| DE69607952T2 (de) | Organoboran-polyaminkomplexe und damit hergestellte klebstoffzusammensetzungen | |
| DE69924302T2 (de) | Organoboran-amin-komplex-initiatorsysteme und damit hergestellte polymerisierbarezusammensetzungen | |
| DE69420131T2 (de) | Blockpolymer, thermoplastisches additionspolymer, ihr herstellungsverfahren und verwendung | |
| DE60307113T3 (de) | STRAHLUNGSHûRTBARER, LÖSUNGSMITTELFREIER UND AUFDRUCKBARER VORGûNGER EINES HAFTKLEBEMITTELS | |
| DE68907397T2 (de) | Flüssige photopolymerisierbare Zusammensetzung, viskoelastisches Produkt, erhalten aus dieser Zusammensetzung und Verfahren zur Herstellung dieses viskoelastischen Produktes. | |
| DE69312970T2 (de) | Strahlenhaertbarer, permanent entfernbarer acrylat/silikon-haftkleber | |
| DE60220831T2 (de) | beta-KETONVERBINDUNGEN ENTHALTENDE INITIATORSYSTEME UND DAMIT HERGESTELLTE ZUSAMMENSETZUNGEN | |
| DE69821265T2 (de) | Geruchsarme polymerisierbare zusammensetzungen zum binden von substraten mit niedriger oberflächenenergie | |
| DE69413885T2 (de) | Silikonmodifiziertes Acrylcopolymer und Klebstoff davon | |
| DE102015222028A1 (de) | Kationisch polymerisierbare Polyacrylate enthaltend Alkoxysilangruppen und deren Verwendung | |
| EP0343477B1 (de) | Harnstoffgruppen enthaltende Dispersionspolymerisate auf Basis ethylenisch ungesättigter Monomerer, Verfahren zu ihrer Herstellung und ihre Verwendung | |
| EP3080223B1 (de) | Vorbehandlung von substraten, die ungesättigte einheiten aufweisen | |
| EP1294783B1 (de) | Verfahren zur herstellung vernetzbarer acrylathaftklebemassen | |
| DE69113230T2 (de) | Vinylpolymer mit (Meth)Acryloyl-Gruppen in die Seitenketten und Verfahren zu seiner Herstellung. | |
| EP3107944B1 (de) | Uv-vernetzbare polymerzusammensetzung | |
| DE102019219167A1 (de) | Bimodaler struktureller Haftklebstoff |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition |