DE69920248T2 - Strahlenhärtbares klebemittel - Google Patents
Strahlenhärtbares klebemittel Download PDFInfo
- Publication number
- DE69920248T2 DE69920248T2 DE69920248T DE69920248T DE69920248T2 DE 69920248 T2 DE69920248 T2 DE 69920248T2 DE 69920248 T DE69920248 T DE 69920248T DE 69920248 T DE69920248 T DE 69920248T DE 69920248 T2 DE69920248 T2 DE 69920248T2
- Authority
- DE
- Germany
- Prior art keywords
- radiation
- adhesive composition
- weight
- composition according
- curable
- 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
- 239000000853 adhesive Substances 0.000 title claims abstract description 61
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 61
- 229920001400 block copolymer Polymers 0.000 claims abstract description 45
- 230000005855 radiation Effects 0.000 claims abstract description 42
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 claims abstract description 38
- 229920005989 resin Polymers 0.000 claims abstract description 27
- 239000011347 resin Substances 0.000 claims abstract description 27
- 239000003381 stabilizer Substances 0.000 claims abstract description 26
- 229920002554 vinyl polymer Polymers 0.000 claims abstract description 13
- 229920006395 saturated elastomer Polymers 0.000 claims abstract description 10
- 230000009477 glass transition Effects 0.000 claims abstract description 6
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 4
- 239000000203 mixture Substances 0.000 claims description 67
- 239000003963 antioxidant agent Substances 0.000 claims description 17
- 125000004432 carbon atom Chemical group C* 0.000 claims description 15
- 125000000217 alkyl group Chemical group 0.000 claims description 12
- 230000003078 antioxidant effect Effects 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 8
- 238000010168 coupling process Methods 0.000 claims description 8
- 229910052739 hydrogen Inorganic materials 0.000 claims description 8
- 230000008878 coupling Effects 0.000 claims description 7
- 238000005859 coupling reaction Methods 0.000 claims description 7
- 239000001257 hydrogen Substances 0.000 claims description 7
- -1 phenolic acrylates Chemical class 0.000 claims description 7
- 239000003795 chemical substances by application Substances 0.000 claims description 6
- 239000007822 coupling agent Substances 0.000 claims description 6
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 claims description 6
- 125000001511 cyclopentyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C1([H])[H] 0.000 claims description 6
- 230000001965 increasing effect Effects 0.000 claims description 6
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 125000001973 tert-pentyl group Chemical group [H]C([H])([H])C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 claims description 6
- 239000012943 hotmelt Substances 0.000 claims description 5
- 150000004945 aromatic hydrocarbons Chemical class 0.000 claims description 4
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 4
- 239000004215 Carbon black (E152) Substances 0.000 claims description 3
- 229930195733 hydrocarbon Natural products 0.000 claims description 3
- 150000002430 hydrocarbons Chemical class 0.000 claims description 3
- 150000002734 metacrylic acid derivatives Chemical class 0.000 claims description 3
- 238000005510 radiation hardening Methods 0.000 claims description 3
- 125000003342 alkenyl group Chemical group 0.000 claims description 2
- 238000000465 moulding Methods 0.000 claims description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims 2
- 125000000753 cycloalkyl group Chemical group 0.000 claims 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims 1
- 239000013032 Hydrocarbon resin Substances 0.000 abstract description 9
- 229920006270 hydrocarbon resin Polymers 0.000 abstract description 9
- 239000003999 initiator Substances 0.000 abstract 1
- 239000004831 Hot glue Substances 0.000 description 13
- 238000009472 formulation Methods 0.000 description 9
- KWVGIHKZDCUPEU-UHFFFAOYSA-N 2,2-dimethoxy-2-phenylacetophenone Chemical compound C=1C=CC=CC=1C(OC)(OC)C(=O)C1=CC=CC=C1 KWVGIHKZDCUPEU-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 229920002633 Kraton (polymer) Polymers 0.000 description 5
- RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 5
- 238000001723 curing Methods 0.000 description 5
- 238000010894 electron beam technology Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 5
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 4
- 241000765083 Ondina Species 0.000 description 4
- JKIJEFPNVSHHEI-UHFFFAOYSA-N Phenol, 2,4-bis(1,1-dimethylethyl)-, phosphite (3:1) Chemical compound CC(C)(C)C1=CC(C(C)(C)C)=CC=C1OP(OC=1C(=CC(=CC=1)C(C)(C)C)C(C)(C)C)OC1=CC=C(C(C)(C)C)C=C1C(C)(C)C JKIJEFPNVSHHEI-UHFFFAOYSA-N 0.000 description 4
- 239000012965 benzophenone Substances 0.000 description 4
- 238000004132 cross linking Methods 0.000 description 4
- 238000005227 gel permeation chromatography Methods 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229920000728 polyester Polymers 0.000 description 4
- 229910001220 stainless steel Inorganic materials 0.000 description 4
- 239000010935 stainless steel Substances 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- WXPWZZHELZEVPO-UHFFFAOYSA-N (4-methylphenyl)-phenylmethanone Chemical compound C1=CC(C)=CC=C1C(=O)C1=CC=CC=C1 WXPWZZHELZEVPO-UHFFFAOYSA-N 0.000 description 3
- LWRBVKNFOYUCNP-UHFFFAOYSA-N 2-methyl-1-(4-methylsulfanylphenyl)-2-morpholin-4-ylpropan-1-one Chemical compound C1=CC(SC)=CC=C1C(=O)C(C)(C)N1CCOCC1 LWRBVKNFOYUCNP-UHFFFAOYSA-N 0.000 description 3
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 3
- VSVVZZQIUJXYQA-UHFFFAOYSA-N [3-(3-dodecylsulfanylpropanoyloxy)-2,2-bis(3-dodecylsulfanylpropanoyloxymethyl)propyl] 3-dodecylsulfanylpropanoate Chemical compound CCCCCCCCCCCCSCCC(=O)OCC(COC(=O)CCSCCCCCCCCCCCC)(COC(=O)CCSCCCCCCCCCCCC)COC(=O)CCSCCCCCCCCCCCC VSVVZZQIUJXYQA-UHFFFAOYSA-N 0.000 description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 description 3
- 125000003118 aryl group Chemical group 0.000 description 3
- 238000001879 gelation Methods 0.000 description 3
- 150000002431 hydrogen Chemical class 0.000 description 3
- 239000003607 modifier Substances 0.000 description 3
- HPAFOABSQZMTHE-UHFFFAOYSA-N phenyl-(2,4,6-trimethylphenyl)methanone Chemical compound CC1=CC(C)=CC(C)=C1C(=O)C1=CC=CC=C1 HPAFOABSQZMTHE-UHFFFAOYSA-N 0.000 description 3
- 229920000642 polymer Polymers 0.000 description 3
- 150000003512 tertiary amines Chemical class 0.000 description 3
- MGMXGCZJYUCMGY-UHFFFAOYSA-N tris(4-nonylphenyl) phosphite Chemical compound C1=CC(CCCCCCCCC)=CC=C1OP(OC=1C=CC(CCCCCCCCC)=CC=1)OC1=CC=C(CCCCCCCCC)C=C1 MGMXGCZJYUCMGY-UHFFFAOYSA-N 0.000 description 3
- DHKHKXVYLBGOIT-UHFFFAOYSA-N 1,1-Diethoxyethane Chemical compound CCOC(C)OCC DHKHKXVYLBGOIT-UHFFFAOYSA-N 0.000 description 2
- VPBZZPOGZPKYKX-UHFFFAOYSA-N 1,2-diethoxypropane Chemical compound CCOCC(C)OCC VPBZZPOGZPKYKX-UHFFFAOYSA-N 0.000 description 2
- IKVYHNPVKUNCJM-UHFFFAOYSA-N 4-propan-2-ylthioxanthen-9-one Chemical compound S1C2=CC=CC=C2C(=O)C2=C1C(C(C)C)=CC=C2 IKVYHNPVKUNCJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000005062 Polybutadiene Substances 0.000 description 2
- 239000004793 Polystyrene Substances 0.000 description 2
- 238000003848 UV Light-Curing Methods 0.000 description 2
- IORUEKDKNHHQAL-UHFFFAOYSA-N [2-tert-butyl-6-[(3-tert-butyl-2-hydroxy-5-methylphenyl)methyl]-4-methylphenyl] prop-2-enoate Chemical compound CC(C)(C)C1=CC(C)=CC(CC=2C(=C(C=C(C)C=2)C(C)(C)C)OC(=O)C=C)=C1O IORUEKDKNHHQAL-UHFFFAOYSA-N 0.000 description 2
- 125000003545 alkoxy group Chemical group 0.000 description 2
- 125000004414 alkyl thio group Chemical group 0.000 description 2
- 239000012298 atmosphere Substances 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 230000015556 catabolic process Effects 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 238000004891 communication Methods 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000006731 degradation reaction Methods 0.000 description 2
- 150000001983 dialkylethers Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 235000011389 fruit/vegetable juice Nutrition 0.000 description 2
- 230000004927 fusion Effects 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000002245 particle Substances 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 2
- 229920002857 polybutadiene Polymers 0.000 description 2
- 229920002223 polystyrene Polymers 0.000 description 2
- 238000001228 spectrum Methods 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 238000009281 ultraviolet germicidal irradiation Methods 0.000 description 2
- NVZWEEGUWXZOKI-UHFFFAOYSA-N 1-ethenyl-2-methylbenzene Chemical compound CC1=CC=CC=C1C=C NVZWEEGUWXZOKI-UHFFFAOYSA-N 0.000 description 1
- QEDJMOONZLUIMC-UHFFFAOYSA-N 1-tert-butyl-4-ethenylbenzene Chemical compound CC(C)(C)C1=CC=C(C=C)C=C1 QEDJMOONZLUIMC-UHFFFAOYSA-N 0.000 description 1
- HBKBEZURJSNABK-MWJPAGEPSA-N 2,3-dihydroxypropyl (1r,4ar,4br,10ar)-1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylate Chemical compound C([C@@H]12)CC(C(C)C)=CC1=CC[C@@H]1[C@]2(C)CCC[C@@]1(C)C(=O)OCC(O)CO HBKBEZURJSNABK-MWJPAGEPSA-N 0.000 description 1
- GHNBXRQAFVCOJI-UHFFFAOYSA-N 2-[2-[1-[2-hydroxy-3,5-bis(2-methylbutan-2-yl)phenyl]ethyl]-4,6-bis(2-methylbutan-2-yl)phenyl]prop-2-enoic acid Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(C(C)C=2C(=C(C=C(C=2)C(C)(C)CC)C(C)(C)CC)C(=C)C(O)=O)=C1O GHNBXRQAFVCOJI-UHFFFAOYSA-N 0.000 description 1
- SCVJRXQHFJXZFZ-KVQBGUIXSA-N 2-amino-9-[(2r,4s,5r)-4-hydroxy-5-(hydroxymethyl)oxolan-2-yl]-3h-purine-6-thione Chemical class C1=2NC(N)=NC(=S)C=2N=CN1[C@H]1C[C@H](O)[C@@H](CO)O1 SCVJRXQHFJXZFZ-KVQBGUIXSA-N 0.000 description 1
- KTALPKYXQZGAEG-UHFFFAOYSA-N 2-propan-2-ylthioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC(C(C)C)=CC=C3SC2=C1 KTALPKYXQZGAEG-UHFFFAOYSA-N 0.000 description 1
- WPMYUUITDBHVQZ-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoic acid Chemical compound CC(C)(C)C1=CC(CCC(O)=O)=CC(C(C)(C)C)=C1O WPMYUUITDBHVQZ-UHFFFAOYSA-N 0.000 description 1
- JLBJTVDPSNHSKJ-UHFFFAOYSA-N 4-Methylstyrene Chemical compound CC1=CC=C(C=C)C=C1 JLBJTVDPSNHSKJ-UHFFFAOYSA-N 0.000 description 1
- APMOEFCWQRJOPS-UHFFFAOYSA-N 5-ethenyl-1,5-dimethylcyclohexa-1,3-diene Chemical compound CC1=CC=CC(C)(C=C)C1 APMOEFCWQRJOPS-UHFFFAOYSA-N 0.000 description 1
- RSWGJHLUYNHPMX-UHFFFAOYSA-N Abietic-Saeure Natural products C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 1
- VIZORQUEIQEFRT-UHFFFAOYSA-N Diethyl adipate Chemical compound CCOC(=O)CCCCC(=O)OCC VIZORQUEIQEFRT-UHFFFAOYSA-N 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- UDSFAEKRVUSQDD-UHFFFAOYSA-N Dimethyl adipate Chemical compound COC(=O)CCCCC(=O)OC UDSFAEKRVUSQDD-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000002879 Lewis base Substances 0.000 description 1
- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 1
- 229910003902 SiCl 4 Inorganic materials 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- STLLXWLDRUVCHL-UHFFFAOYSA-N [2-[1-[2-hydroxy-3,5-bis(2-methylbutan-2-yl)phenyl]ethyl]-4,6-bis(2-methylbutan-2-yl)phenyl] prop-2-enoate Chemical compound CCC(C)(C)C1=CC(C(C)(C)CC)=CC(C(C)C=2C(=C(C=C(C=2)C(C)(C)CC)C(C)(C)CC)OC(=O)C=C)=C1O STLLXWLDRUVCHL-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 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
- 150000001412 amines Chemical class 0.000 description 1
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 description 1
- 239000002585 base Substances 0.000 description 1
- 230000005540 biological transmission Effects 0.000 description 1
- 150000001728 carbonyl compounds Chemical class 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 239000008199 coating composition Substances 0.000 description 1
- 150000001993 dienes Chemical class 0.000 description 1
- 238000009826 distribution Methods 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 239000000374 eutectic mixture Substances 0.000 description 1
- 230000007717 exclusion Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 239000011261 inert gas Substances 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 230000005865 ionizing radiation Effects 0.000 description 1
- 150000007527 lewis bases Chemical class 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- 229910052760 oxygen Inorganic materials 0.000 description 1
- 239000001301 oxygen Substances 0.000 description 1
- 239000002530 phenolic antioxidant Substances 0.000 description 1
- AQSJGOWTSHOLKH-UHFFFAOYSA-N phosphite(3-) Chemical class [O-]P([O-])[O-] AQSJGOWTSHOLKH-UHFFFAOYSA-N 0.000 description 1
- OJMIONKXNSYLSR-UHFFFAOYSA-N phosphorous acid Chemical compound OP(O)O OJMIONKXNSYLSR-UHFFFAOYSA-N 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 238000003847 radiation curing Methods 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000000979 retarding effect Effects 0.000 description 1
- 238000012552 review Methods 0.000 description 1
- 239000000565 sealant Substances 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- FDNAPBUWERUEDA-UHFFFAOYSA-N silicon tetrachloride Chemical compound Cl[Si](Cl)(Cl)Cl FDNAPBUWERUEDA-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000009987 spinning Methods 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920000468 styrene butadiene styrene block copolymer Polymers 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 150000003464 sulfur compounds Chemical class 0.000 description 1
- NUMQCACRALPSHD-UHFFFAOYSA-N tert-butyl ethyl ether Chemical compound CCOC(C)(C)C NUMQCACRALPSHD-UHFFFAOYSA-N 0.000 description 1
- LFQCEHFDDXELDD-UHFFFAOYSA-N tetramethyl orthosilicate Chemical compound CO[Si](OC)(OC)OC LFQCEHFDDXELDD-UHFFFAOYSA-N 0.000 description 1
- 229920002725 thermoplastic elastomer Polymers 0.000 description 1
- KHPCPRHQVVSZAH-UHFFFAOYSA-N trans-cinnamyl beta-D-glucopyranoside Natural products OC1C(O)C(O)C(CO)OC1OCC=CC1=CC=CC=C1 KHPCPRHQVVSZAH-UHFFFAOYSA-N 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
- C09J153/00—Adhesives based on block copolymers containing at least one sequence of a polymer obtained by reactions only involving carbon-to-carbon unsaturated bonds; Adhesives based on derivatives of such polymers
- C09J153/02—Vinyl aromatic monomers and conjugated dienes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/02—Organic macromolecular compounds, natural resins, waxes or and bituminous materials
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Adhesive Tapes (AREA)
Applications Claiming Priority (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| EP98308255 | 1998-10-09 | ||
| EP98308255 | 1998-10-09 | ||
| PCT/EP1999/007759 WO2000022062A1 (en) | 1998-10-09 | 1999-10-08 | Radiation-curable adhesive |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| DE69920248D1 DE69920248D1 (de) | 2004-10-21 |
| DE69920248T2 true DE69920248T2 (de) | 2005-01-27 |
Family
ID=8235096
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE69920248T Expired - Lifetime DE69920248T2 (de) | 1998-10-09 | 1999-10-08 | Strahlenhärtbares klebemittel |
Country Status (6)
| Country | Link |
|---|---|
| EP (1) | EP1123362B1 (https=) |
| JP (1) | JP2002527568A (https=) |
| AT (1) | ATE276326T1 (https=) |
| AU (1) | AU6472099A (https=) |
| DE (1) | DE69920248T2 (https=) |
| WO (1) | WO2000022062A1 (https=) |
Families Citing this family (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP1360258B1 (en) | 2000-01-31 | 2007-03-14 | H.B. Fuller Licensing & Financing, Inc. | Radiation curable adhesive compositions comprising block copolymers having vinyl functionalized polydiene blocks |
| DE10212049A1 (de) | 2002-03-19 | 2003-10-02 | Tesa Ag | Haftklebemasse und Verfahren zur Herstellung hierzu |
| DE10234369A1 (de) | 2002-07-27 | 2004-02-12 | Henkel Kgaa | Strahlungsvernetzbare Schmelzhaftklebstoffe |
| US7262242B2 (en) | 2004-02-18 | 2007-08-28 | Eastman Chemical Company | Aromatic/acrylate tackifier resin and acrylic polymer blends |
| US7332540B2 (en) | 2004-02-18 | 2008-02-19 | Eastman Chemical Company | Aromatic-acrylate tackifier resins |
| US7238732B2 (en) | 2004-02-18 | 2007-07-03 | Eastman Chemical Company | Radiation-curable adhesive compositions |
| DE102005006282A1 (de) | 2005-02-10 | 2006-08-24 | Henkel Kgaa | Strahlungsvernetzbare Schmelzhaftklebstoffe |
| JP5129556B2 (ja) * | 2007-12-14 | 2013-01-30 | サンスター技研株式会社 | 接着剤組成物 |
| DE102008056980A1 (de) * | 2008-11-12 | 2010-05-20 | Tesa Se | Strahlenchemisch vernetzbare, geschäumte Selbstklebemasse basierend auf Vinylaromatenblockcopolymeren |
| EP3357968B1 (en) | 2015-09-30 | 2025-10-15 | Zeon Corporation | Block copolymer composition and hot melt adhesive composition |
| CN107057618B (zh) * | 2017-06-05 | 2018-10-26 | 湖北大学 | 一种辐照交联的医用压敏胶及其制备方法 |
| DE102018204463A1 (de) * | 2018-03-23 | 2019-09-26 | Tesa Se | Witterungsbeständige Klebemasse mit gutem Auffließvermögen und darauf basierende Klebebänder |
| FR3098520B1 (fr) * | 2019-07-10 | 2022-07-22 | Bostik Sa | HMPSA réticulable sous irradiation UV |
| DE102021201094A1 (de) | 2021-02-05 | 2022-08-11 | Tesa Se | Polyvinylaromat-Polydien-Blockcopolymer basierende Haftklebemassen mit gesteigerter Wärmescherfestigkeit |
| JP2024018177A (ja) * | 2022-07-29 | 2024-02-08 | アイカ工業株式会社 | 光硬化型ホットメルト組成物 |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4792584A (en) * | 1986-05-02 | 1988-12-20 | Asahi Kasei Kogyo Kabushiki Kaisha | Adhesive compositions |
| US5104921A (en) * | 1988-02-17 | 1992-04-14 | Shell Oil Company | Radiation cured polymer composition |
| TW274086B (https=) * | 1992-06-04 | 1996-04-11 | Shell Internat Res Schappej Bv | |
| US5804663A (en) * | 1995-03-16 | 1998-09-08 | Shell Oil Company | Radiation sensitive vinyl aromatic block copolymers and compositions containing them |
| US5777039A (en) * | 1996-02-09 | 1998-07-07 | Shell Oil Company | Vinyl aromatic block copolymers and compositions containing them |
| US5916959A (en) * | 1996-03-29 | 1999-06-29 | H.B. Fuller Licensing & Financing, Inc. | Radial styrene-isoprene-styrene based hot melt pressure sensitive adhesive |
| US6172156B1 (en) * | 1996-07-03 | 2001-01-09 | H. B. Fuller Licensing & Financing, Inc. | Cohesively failing hot melt pressure sensitive adhesive |
| EP1091998B1 (en) * | 1998-06-29 | 2004-08-04 | KRATON Polymers Research B.V. | Photo-curable polymer composition and flexographic printing plates containing the same |
-
1999
- 1999-10-08 AT AT99952572T patent/ATE276326T1/de not_active IP Right Cessation
- 1999-10-08 JP JP2000575958A patent/JP2002527568A/ja active Pending
- 1999-10-08 EP EP99952572A patent/EP1123362B1/en not_active Expired - Lifetime
- 1999-10-08 WO PCT/EP1999/007759 patent/WO2000022062A1/en not_active Ceased
- 1999-10-08 DE DE69920248T patent/DE69920248T2/de not_active Expired - Lifetime
- 1999-10-08 AU AU64720/99A patent/AU6472099A/en not_active Abandoned
Also Published As
| Publication number | Publication date |
|---|---|
| DE69920248D1 (de) | 2004-10-21 |
| EP1123362B1 (en) | 2004-09-15 |
| ATE276326T1 (de) | 2004-10-15 |
| JP2002527568A (ja) | 2002-08-27 |
| EP1123362A1 (en) | 2001-08-16 |
| AU6472099A (en) | 2000-05-01 |
| WO2000022062A1 (en) | 2000-04-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| DE69920248T2 (de) | Strahlenhärtbares klebemittel | |
| DE69304328T2 (de) | Vinylaromatische blockcopolymere, die bei strahlenvernetzung hochempfindlich sind und diese enthaltende zusammensetzungen | |
| DE602005001556T2 (de) | Strahlungshärtbare klebstoffzusammensetzung | |
| DE60033159T2 (de) | Mittels energie härtbare zusammensetzung zur herstellung eines druckempfindlichen klebstoffs | |
| DE60127306T2 (de) | Strahlungshärtbare klebstoffzusammensetzungen enthaltend blockcopolymere mit vinylfunktionalisierten polybutadienblöcken | |
| DE69434507T2 (de) | Haftklebstoffzusammensetzung und Klebeband, das diese verwendet | |
| DE3851094T2 (de) | Ein thermoplastisches Polymer, ein verträgliches, härtbares Urethanpolyalkylenpolyol-Prepolymer und einen Klebrigmacher enthaltende wärmebeständige reaktive Urethan-Schmelzklebstoff-Zusammensetzung. | |
| DE69408474T2 (de) | Hydrierte multiblockpolymere für klebemittel | |
| DE10008842C1 (de) | Polymerblends | |
| DE69403775T2 (de) | Blockcopolymer mit Endblöcken verschiedenen Molekulargewichts | |
| DE68907397T2 (de) | Flüssige photopolymerisierbare Zusammensetzung, viskoelastisches Produkt, erhalten aus dieser Zusammensetzung und Verfahren zur Herstellung dieses viskoelastischen Produktes. | |
| DE69919172T2 (de) | Photohärtbare polymerzusammensetzung und diese enthaltende flexodruckplatten | |
| JP3675842B2 (ja) | ビニル芳香族ブロックコポリマー並びにそれらを含有する組成物 | |
| DE69833800T2 (de) | Schmelzklebstoffe aus blockcopolymeren, verfahren zu ihrer herstellung und gegenstände daraus | |
| DE3015463C2 (de) | Verfahren zur Herstellung von Haftschmelzkleberbeschichtungen auf Substraten | |
| DE112008001404T5 (de) | Photohärtbare Haftklebstoffzusammensetzung | |
| DE3105343A1 (de) | "photoaktives gemisch aus acryl-monomeren und chromophor-substituiertem halogenmethyl-s-triazin und hieraus hergestellte erzeugnisse und verfahren zu deren herstellung | |
| DE69931817T2 (de) | Photohärtbare polymer-zusammensetzung und diese enthaltende flexodruckplatten | |
| DE102007063021A1 (de) | Corona-behandelte Klebemassen | |
| EP0258719A2 (de) | Zweischichtensystem | |
| DE102015217131A1 (de) | Klebharz-modifizierte Haftklebemasse | |
| DE69016406T2 (de) | Klebstoffzusammensetzung. | |
| EP1370590B1 (de) | Verfahren zur herstellung von vernetzten acrylatschmelzhaftklebemassen | |
| DE2813544A1 (de) | Durch bestrahlen aushaertbare, druckempfindliche klebstoffzusammensetzungen | |
| DE3134157C2 (de) | Polycarbonatkörper mit einem Überzug und Verfahren zu ihrer Herstellung |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| 8364 | No opposition during term of opposition | ||
| 8328 | Change in the person/name/address of the agent |
Representative=s name: STOLMAR SCHEELE & PARTNER, 80331 MUENCHEN |