JPH0582855B2 - - Google Patents
Info
- Publication number
- JPH0582855B2 JPH0582855B2 JP21925485A JP21925485A JPH0582855B2 JP H0582855 B2 JPH0582855 B2 JP H0582855B2 JP 21925485 A JP21925485 A JP 21925485A JP 21925485 A JP21925485 A JP 21925485A JP H0582855 B2 JPH0582855 B2 JP H0582855B2
- Authority
- JP
- Japan
- Prior art keywords
- vinyl acetate
- ethylene
- acetate copolymer
- eva
- monofunctional
- 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
- 239000005038 ethylene vinyl acetate Substances 0.000 claims description 20
- 239000000203 mixture Substances 0.000 claims description 20
- 229920001200 poly(ethylene-vinyl acetate) Polymers 0.000 claims description 20
- 230000001070 adhesive effect Effects 0.000 claims description 15
- 229920001577 copolymer Polymers 0.000 claims description 13
- -1 maleimide compound Chemical class 0.000 claims description 13
- 239000000853 adhesive Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 claims description 10
- 239000005977 Ethylene Substances 0.000 claims description 10
- 125000001651 cyanato group Chemical group [*]OC#N 0.000 claims description 9
- 239000004643 cyanate ester Substances 0.000 claims description 8
- 239000003054 catalyst Substances 0.000 claims description 5
- 238000004132 cross linking Methods 0.000 claims description 5
- 238000012986 modification Methods 0.000 claims description 4
- 230000004048 modification Effects 0.000 claims description 4
- DQXBYHZEEUGOBF-UHFFFAOYSA-N but-3-enoic acid;ethene Chemical class C=C.OC(=O)CC=C DQXBYHZEEUGOBF-UHFFFAOYSA-N 0.000 claims 1
- 230000001737 promoting effect Effects 0.000 claims 1
- 229920006163 vinyl copolymer Polymers 0.000 claims 1
- 229910052751 metal Inorganic materials 0.000 description 6
- 239000002184 metal Substances 0.000 description 6
- 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 4
- XEEYBQQBJWHFJM-UHFFFAOYSA-N Iron Chemical compound [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 4
- 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 4
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 4
- 229910052782 aluminium Inorganic materials 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011888 foil Substances 0.000 description 4
- 239000012188 paraffin wax Substances 0.000 description 4
- 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 4
- XMNIXWIUMCBBBL-UHFFFAOYSA-N 2-(2-phenylpropan-2-ylperoxy)propan-2-ylbenzene Chemical compound C=1C=CC=CC=1C(C)(C)OOC(C)(C)C1=CC=CC=C1 XMNIXWIUMCBBBL-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 description 3
- 238000000465 moulding Methods 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- 239000000243 solution Substances 0.000 description 3
- VTYYLEPIZMXCLO-UHFFFAOYSA-L Calcium carbonate Chemical compound [Ca+2].[O-]C([O-])=O VTYYLEPIZMXCLO-UHFFFAOYSA-L 0.000 description 2
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 2
- 239000004831 Hot glue Substances 0.000 description 2
- UQSXHKLRYXJYBZ-UHFFFAOYSA-N Iron oxide Chemical compound [Fe]=O UQSXHKLRYXJYBZ-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- AHZMUXQJTGRNHT-UHFFFAOYSA-N [4-[2-(4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1C(C)(C)C1=CC=C(OC#N)C=C1 AHZMUXQJTGRNHT-UHFFFAOYSA-N 0.000 description 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 2
- 125000003118 aryl group Chemical group 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 238000000576 coating method Methods 0.000 description 2
- 239000010941 cobalt Substances 0.000 description 2
- 229910017052 cobalt Inorganic materials 0.000 description 2
- GUTLYIVDDKVIGB-UHFFFAOYSA-N cobalt atom Chemical compound [Co] GUTLYIVDDKVIGB-UHFFFAOYSA-N 0.000 description 2
- XLJMAIOERFSOGZ-UHFFFAOYSA-N cyanic acid Chemical class OC#N XLJMAIOERFSOGZ-UHFFFAOYSA-N 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 238000004898 kneading Methods 0.000 description 2
- KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- VNWKTOKETHGBQD-UHFFFAOYSA-N methane Chemical compound C VNWKTOKETHGBQD-UHFFFAOYSA-N 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000000962 organic group Chemical group 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 239000000843 powder Substances 0.000 description 2
- 238000002407 reforming Methods 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000001993 wax Substances 0.000 description 2
- UFKLQICEQCIWNE-UHFFFAOYSA-N (3,5-dicyanatophenyl) cyanate Chemical compound N#COC1=CC(OC#N)=CC(OC#N)=C1 UFKLQICEQCIWNE-UHFFFAOYSA-N 0.000 description 1
- YDCUTCGACVVRIQ-UHFFFAOYSA-N (3,6-dicyanatonaphthalen-1-yl) cyanate Chemical compound N#COC1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 YDCUTCGACVVRIQ-UHFFFAOYSA-N 0.000 description 1
- GUGZCSAPOLLKNG-UHFFFAOYSA-N (4-cyanatophenyl) cyanate Chemical compound N#COC1=CC=C(OC#N)C=C1 GUGZCSAPOLLKNG-UHFFFAOYSA-N 0.000 description 1
- OFIWROJVVHYHLQ-UHFFFAOYSA-N (7-cyanatonaphthalen-2-yl) cyanate Chemical compound C1=CC(OC#N)=CC2=CC(OC#N)=CC=C21 OFIWROJVVHYHLQ-UHFFFAOYSA-N 0.000 description 1
- KCFXNGDHQPMIAQ-UHFFFAOYSA-N 1-(4-methylphenyl)pyrrole-2,5-dione Chemical compound C1=CC(C)=CC=C1N1C(=O)C=CC1=O KCFXNGDHQPMIAQ-UHFFFAOYSA-N 0.000 description 1
- 150000003923 2,5-pyrrolediones Chemical class 0.000 description 1
- 239000004342 Benzoyl peroxide Substances 0.000 description 1
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 description 1
- VYZAMTAEIAYCRO-UHFFFAOYSA-N Chromium Chemical compound [Cr] VYZAMTAEIAYCRO-UHFFFAOYSA-N 0.000 description 1
- QPLDLSVMHZLSFG-UHFFFAOYSA-N Copper oxide Chemical compound [Cu]=O QPLDLSVMHZLSFG-UHFFFAOYSA-N 0.000 description 1
- 239000005751 Copper oxide Substances 0.000 description 1
- 239000001293 FEMA 3089 Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- PWHULOQIROXLJO-UHFFFAOYSA-N Manganese Chemical compound [Mn] PWHULOQIROXLJO-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 229920002367 Polyisobutene Polymers 0.000 description 1
- 244000181025 Rosa gallica Species 0.000 description 1
- 235000000533 Rosa gallica Nutrition 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- GWEVSGVZZGPLCZ-UHFFFAOYSA-N Titan oxide Chemical compound O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
- BZHJMEDXRYGGRV-UHFFFAOYSA-N Vinyl chloride Chemical compound ClC=C BZHJMEDXRYGGRV-UHFFFAOYSA-N 0.000 description 1
- GXFRMDVUWJDFAI-UHFFFAOYSA-N [2,6-dibromo-4-[2-(3,5-dibromo-4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C(Br)=C(OC#N)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(OC#N)C(Br)=C1 GXFRMDVUWJDFAI-UHFFFAOYSA-N 0.000 description 1
- YKONYNBAMHVIMF-UHFFFAOYSA-N [2,6-dichloro-4-[2-(3,5-dichloro-4-cyanatophenyl)propan-2-yl]phenyl] cyanate Chemical compound C=1C(Cl)=C(OC#N)C(Cl)=CC=1C(C)(C)C1=CC(Cl)=C(OC#N)C(Cl)=C1 YKONYNBAMHVIMF-UHFFFAOYSA-N 0.000 description 1
- SNYVZKMCGVGTKN-UHFFFAOYSA-N [4-(4-cyanatophenoxy)phenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OC1=CC=C(OC#N)C=C1 SNYVZKMCGVGTKN-UHFFFAOYSA-N 0.000 description 1
- HEJGXMCFSSDPOA-UHFFFAOYSA-N [4-(4-cyanatophenyl)phenyl] cyanate Chemical group C1=CC(OC#N)=CC=C1C1=CC=C(OC#N)C=C1 HEJGXMCFSSDPOA-UHFFFAOYSA-N 0.000 description 1
- CNUHQZDDTLOZRY-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfanylphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1SC1=CC=C(OC#N)C=C1 CNUHQZDDTLOZRY-UHFFFAOYSA-N 0.000 description 1
- BUPOATPDNYBPMR-UHFFFAOYSA-N [4-(4-cyanatophenyl)sulfonylphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1S(=O)(=O)C1=CC=C(OC#N)C=C1 BUPOATPDNYBPMR-UHFFFAOYSA-N 0.000 description 1
- PPZSVSGWDQKBIW-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphanyloxyphenyl] cyanate Chemical compound C1=CC(OC#N)=CC=C1OP(OC=1C=CC(OC#N)=CC=1)OC1=CC=C(OC#N)C=C1 PPZSVSGWDQKBIW-UHFFFAOYSA-N 0.000 description 1
- HYAOCWBXRFEHDV-UHFFFAOYSA-N [4-bis(4-cyanatophenoxy)phosphoryloxyphenyl] cyanate Chemical compound C=1C=C(OC#N)C=CC=1OP(OC=1C=CC(OC#N)=CC=1)(=O)OC1=CC=C(OC#N)C=C1 HYAOCWBXRFEHDV-UHFFFAOYSA-N 0.000 description 1
- 239000006096 absorbing agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- 239000002313 adhesive film Substances 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- WNROFYMDJYEPJX-UHFFFAOYSA-K aluminium hydroxide Chemical compound [OH-].[OH-].[OH-].[Al+3] WNROFYMDJYEPJX-UHFFFAOYSA-K 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- UHHXUPJJDHEMGX-UHFFFAOYSA-K azanium;manganese(3+);phosphonato phosphate Chemical compound [NH4+].[Mn+3].[O-]P([O-])(=O)OP([O-])([O-])=O UHHXUPJJDHEMGX-UHFFFAOYSA-K 0.000 description 1
- IRERQBUNZFJFGC-UHFFFAOYSA-L azure blue Chemical compound [Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Na+].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[Al+3].[S-]S[S-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-].[O-][Si]([O-])([O-])[O-] IRERQBUNZFJFGC-UHFFFAOYSA-L 0.000 description 1
- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 229910000019 calcium carbonate Inorganic materials 0.000 description 1
- AXCZMVOFGPJBDE-UHFFFAOYSA-L calcium dihydroxide Chemical compound [OH-].[OH-].[Ca+2] AXCZMVOFGPJBDE-UHFFFAOYSA-L 0.000 description 1
- 239000000920 calcium hydroxide Substances 0.000 description 1
- 229910001861 calcium hydroxide Inorganic materials 0.000 description 1
- 239000006229 carbon black Substances 0.000 description 1
- 235000019241 carbon black Nutrition 0.000 description 1
- 125000003178 carboxy group Chemical class [H]OC(*)=O 0.000 description 1
- 229910052804 chromium Inorganic materials 0.000 description 1
- 239000011651 chromium Substances 0.000 description 1
- 239000004927 clay Substances 0.000 description 1
- 229910052570 clay Inorganic materials 0.000 description 1
- 239000003426 co-catalyst Substances 0.000 description 1
- 235000013495 cobalt Nutrition 0.000 description 1
- 229910000152 cobalt phosphate Inorganic materials 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 239000011889 copper foil Substances 0.000 description 1
- 229910000431 copper oxide Inorganic materials 0.000 description 1
- XCJYREBRNVKWGJ-UHFFFAOYSA-N copper(II) phthalocyanine Chemical compound [Cu+2].C12=CC=CC=C2C(N=C2[N-]C(C3=CC=CC=C32)=N2)=NC1=NC([C]1C=CC=CC1=1)=NC=1N=C1[C]3C=CC=CC3=C2[N-]1 XCJYREBRNVKWGJ-UHFFFAOYSA-N 0.000 description 1
- 230000006866 deterioration Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 239000003822 epoxy resin Substances 0.000 description 1
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- 125000000524 functional group Chemical class 0.000 description 1
- JMANVNJQNLATNU-UHFFFAOYSA-N glycolonitrile Natural products N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 description 1
- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- RBTKNAXYKSUFRK-UHFFFAOYSA-N heliogen blue Chemical compound [Cu].[N-]1C2=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=NC([N-]1)=C(C=CC=C3)C3=C1N=C([N-]1)C3=CC=CC=C3C1=N2 RBTKNAXYKSUFRK-UHFFFAOYSA-N 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000011256 inorganic filler Substances 0.000 description 1
- 229910003475 inorganic filler Inorganic materials 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- LZKLAOYSENRNKR-LNTINUHCSA-N iron;(z)-4-oxoniumylidenepent-2-en-2-olate Chemical compound [Fe].C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O.C\C(O)=C\C(C)=O LZKLAOYSENRNKR-LNTINUHCSA-N 0.000 description 1
- 229910000464 lead oxide Inorganic materials 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- VTHJTEIRLNZDEV-UHFFFAOYSA-L magnesium dihydroxide Chemical compound [OH-].[OH-].[Mg+2] VTHJTEIRLNZDEV-UHFFFAOYSA-L 0.000 description 1
- 239000000347 magnesium hydroxide Substances 0.000 description 1
- 229910001862 magnesium hydroxide Inorganic materials 0.000 description 1
- 229910052748 manganese Inorganic materials 0.000 description 1
- 239000011572 manganese Substances 0.000 description 1
- WPBNNNQJVZRUHP-UHFFFAOYSA-L manganese(2+);methyl n-[[2-(methoxycarbonylcarbamothioylamino)phenyl]carbamothioyl]carbamate;n-[2-(sulfidocarbothioylamino)ethyl]carbamodithioate Chemical compound [Mn+2].[S-]C(=S)NCCNC([S-])=S.COC(=O)NC(=S)NC1=CC=CC=C1NC(=S)NC(=O)OC WPBNNNQJVZRUHP-UHFFFAOYSA-L 0.000 description 1
- 229910044991 metal oxide Inorganic materials 0.000 description 1
- 150000004706 metal oxides Chemical class 0.000 description 1
- 239000010445 mica Substances 0.000 description 1
- 229910052618 mica group Inorganic materials 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 239000003607 modifier Substances 0.000 description 1
- QUSFOLYSOPZYIK-UHFFFAOYSA-N naphthalen-1-yl cyanate Chemical compound C1=CC=C2C(OC#N)=CC=CC2=C1 QUSFOLYSOPZYIK-UHFFFAOYSA-N 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- 229920003986 novolac Polymers 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- 150000002902 organometallic compounds Chemical class 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N oxolead Chemical compound [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- CWHFDTWZHFRTAB-UHFFFAOYSA-N phenyl cyanate Chemical compound N#COC1=CC=CC=C1 CWHFDTWZHFRTAB-UHFFFAOYSA-N 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 239000000049 pigment Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920001084 poly(chloroprene) Polymers 0.000 description 1
- 229920002492 poly(sulfone) Polymers 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006289 polycarbonate film Polymers 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920001721 polyimide Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- 235000013799 ultramarine blue Nutrition 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- CHJMFFKHPHCQIJ-UHFFFAOYSA-L zinc;octanoate Chemical compound [Zn+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O CHJMFFKHPHCQIJ-UHFFFAOYSA-L 0.000 description 1
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Adhesives Or Adhesive Processes (AREA)
Description
〔産業上の利用分野〕
本発明は、改質されたエチレン・酢酸ビニル共
重合体組成物であり、機械的特性に優れ、接着性
の改良されものであり、成形体、接着剤や接着用
のシート、溶液等として好適に使用されるもので
ある。
〔従来の技術およびその問題点〕
エチレン・酢酸ビニル共重合体（以下、EVA
と適宜略記する）は、柔軟性、ゴム弾性、低温特
性に優れた熱可塑性樹脂であり、ワツクスへのブ
レンド、ホツトメルト接着剤用ベース樹脂、成形
品として広く利用されている。EVAとロジン類、
テレピン油、ポリイソブチレン、パチフインなど
の粘着剤やワツクス類と混合して作られるホツト
メルト接着剤は、必ずしも接着力は充分ではな
く、又高温で接着力が弱い欠点がある。
本発明は、高強度で接着力の著しく優れたエチ
レン・酢酸ビニル共重合体組成物を見出したもの
である。
〔問題点を解決するための手段〕
本発明は、シアナト基（−Ｏ−Ｃ≡Ｎ）を有す
る化合物のシアナト基のユニークな性質の利用に
ついて種々検討した結果、EVAにシアナト基を
有する化合物を添加することにより、EVAの機
械的特性と接着性を大幅に向上させることが出来
ることを見出し、完成したものである。
すなわち、本発明は、エチレン・酢酸ビニル共
重合体に、分子中にシアナト基を１個以上含有す
る単官能性もしくは多官能性シアン酸エステル化
合物を0.1〜20重量％混合してなる接着性の改質
されたエチレン・酢酸ビニル共重合体組成物であ
り、好ましくは実施態様においては該シアン酸エ
ステル化合物による接着性の改質を促進する改質
用助剤として、該エチレン・酢酸ビニル共重合体
の架橋触媒又は単官能若しくは多官能性マレイミ
ド化合物を該エチレン・酢酸ビニル共重合体を基
準としてそれぞれ0.1〜５重量％併用混合してな
る改質されたエチレン・酢酸ビニル共重合体であ
る。
以下、本発明について説明する。
本発明のエチレン・酢酸ビニル共重合体とは、
公知のエチレンと酢酸ビニルとの共重合体類（＝
EVA）であるが、通常のEVAと塩化ビニル、ポ
リエチレン、ポリカーボネート、エチレン・プロ
ピレンゴムなどの公知のプラスチツクスとの混合
物や通常のEVAとロジン、パラフイン、塩素化
ジフエニル、ネオプレン、ニトリルゴム等の粘着
剤、ワツクス類との混合物として、また、炭酸カ
ルシウム、水酸化マグネシウム、水酸化アルミニ
ウム、水酸化カルシウム、タルク、クレイ、マイ
カ、ウオラストナイトなどの無機充填剤、銅、
鉄、コバルト、ニツケル、クロム、マンガン、ア
ルミニウム、マンガン又はこれら金属の合金など
の粉体、繊維、薄片など金属、酸化銅、酸化鉄、
三酸化アンチモン、酸化鉛などの粉体、繊維、薄
片など金属酸化物、銅フタロシアニン（＝フタロ
シアニンブルー）などの有機金属化合物、黄鉛、
ミネラルバイオレツト、カーボンブラツク、べん
がら、群青、コバルトブルー、コバルトバイオレ
ツト、チタン白などの顔料、その他可塑剤、難燃
剤、紫外線吸収剤、安定剤等を添加した組成物と
して、更にエポキシ樹脂などの熱硬化性樹脂を添
加した組成物としても効果を奏するものであり、
これら組成物も含まれる。
以上の成分からなるEVA組成物に改質剤とし
て添加する本発明の分子中にシアナト基を１個以
上含有する単官能性もしくは多官能性シアン酸エ
ステル化合物として好適なものは、下記一般式(1)
一般式(1)：
Ｒ（OCN）ｍ …(1)
（式中のｍは１以上、通常５以下の整数であり、
Ｒは芳香族の有機基であつて、上記シアナト基は
該有機基の芳香環に結合しているもの）
で表される化合物である。具体的に例示すればモ
ノシアナトベンゼン、Ｐ−tert−ブチルシアナト
ベンゼンなどのアルキルシアナトベンゼン、モノ
シアナトナフタレン、１，３−又は１，４−ジシ
アナトベンゼン、１，３，５−トリシアナトベン
ゼン、１，３−、１，４−、１，６−、１，８
−、２，６−又は２，７−ジシアナトナフタレ
ン、１，３，６−トリシアナトナフタレン、４，
4′−ジシアナトビフエニル、ビス（４−ジシアナ
トフエニル）メタン、２，２−ビス（４−シアナ
トフエニル）プロパン、２，２−ビス（３，５−
ジクロロ−４−シアナトフエニル）プロパン、
２，２−ビス（３，５−ジブロモ−４−シアナト
フエニル）プロパン、ビス（４−シアナトフエニ
ル）エーテル、ビス（４−シアナトフエニル）チ
オエーテル、ビス（４−シアナトフエニル）スル
ホン、トリス（４−シアナトフエニル）ホスフア
イト、トリス（４−シアナトフエニル）ホスフエ
ート、およびノボラツクとハロゲン化シアンとの
反応により得られるシアン酸エステルなどであ
る。これらのほかに特公昭41−1928、同43−
18468、同44−4791、同45−11712、同46−41112、
同47−26853および特開昭51−63149などに記載の
シアン酸エステルも用い得る。
又、上述した多官能性シアン酸エステルをその
まま、又は鉱酸、ルイス酸、炭酸ナトリウム或い
は塩化リチウム等の塩類、トリブチルホスフイン
等のリン酸エステル類、有機金属塩類などの存在
下に重合させて得られる分子中にシアナト基を有
するプレポリマーとして使用出来し、後記する改
質用助剤である単官能若しくは多官能性マレイミ
ド化合物との予備混合物もしくは予備反応物（＝
プレポリマー）として使用出来し、さらに後記す
るマレイミド化合物の原料であるアミンとのプレ
ポリマーとしても使用出来る。
以上説明した本発明のシアン酸エステル化合物
のEVAに対する配合量は、特に限定はないが、
効果の点から0.1〜20重量％の範囲から適宜選択
する。添加量が0.1％未満では、特性向上効果が
不充分であり、20重量％を超えて使用した場合、
安定性などの劣化防止には顕著な効果を示すが、
接着力の低下やEVAの伸びの低下などのその他
の特性が損なわれるので好ましくない。また前記
に説明した如く、本発明の効果にはシアナト基が
必要であるので、この官能基と反応する添加剤類
−例えば、−OH、−COOH、−NH2、−COOM、−
SH等（Ｍ＝金属原子）−を有する化合物を添加す
る必要のある場合には、シアン酸エステル化合物
とこれらの化合物を予め混合して添加することな
どは避けた方が好ましい。
本発明の改質用助剤として使用するEVAを架
橋する架橋触媒とは、例えば、ジクミルパーオキ
サイドなどの公知の有機過酸化物や硫黄及びこれ
ら公知の触媒とその助触媒であるアセチルアセト
ン鉄やオクチル酸亜鉛などの公知の金属キレート
や有機金属塩との併用物が例示され、使用量は、
EVA組成物に対して、通常0.1〜５重量％が好適
である。
又、本発明のEVA組成物を基準として0.1〜５
重量％の単官能若しくは多官能性マレイミド化合
物も単独で又は上記の架橋触媒と併用して改質用
助剤として好適に用いることができる。
このような単官能若しくは多官能性マレイミド
化合物として好ましい化合物は下記一般式(2)、
一般式(2)：
[Industrial Application Field] The present invention is a modified ethylene/vinyl acetate copolymer composition, which has excellent mechanical properties and improved adhesive properties, and is suitable for use in molded objects, adhesives, and adhesives. It is suitably used as a sheet, solution, etc. [Conventional technology and its problems] Ethylene-vinyl acetate copolymer (hereinafter referred to as EVA)
(abbreviated as appropriate) is a thermoplastic resin with excellent flexibility, rubber elasticity, and low-temperature properties, and is widely used as a blend into wax, a base resin for hot melt adhesives, and molded products. EVA and rosin,
Hot-melt adhesives made by mixing adhesives and waxes such as turpentine oil, polyisobutylene, and patifine do not necessarily have sufficient adhesive strength, and also have the drawback of weak adhesive strength at high temperatures. The present invention is based on the discovery of an ethylene/vinyl acetate copolymer composition that has high strength and excellent adhesive strength. [Means for Solving the Problems] As a result of various studies on the use of the unique properties of cyanato groups in compounds having cyanato groups (-O-C≡N), the present invention has developed a method of incorporating a compound having a cyanato group into EVA. This was completed after discovering that the mechanical properties and adhesive properties of EVA can be significantly improved by adding it. That is, the present invention provides an adhesive product made by mixing an ethylene/vinyl acetate copolymer with 0.1 to 20% by weight of a monofunctional or polyfunctional cyanate ester compound containing one or more cyanato groups in the molecule. It is a modified ethylene/vinyl acetate copolymer composition, and preferably in an embodiment, the ethylene/vinyl acetate copolymer is used as a modification aid to promote adhesive modification by the cyanate ester compound. This is a modified ethylene/vinyl acetate copolymer obtained by co-mixing a crosslinking catalyst or a monofunctional or polyfunctional maleimide compound in an amount of 0.1 to 5% by weight based on the ethylene/vinyl acetate copolymer. The present invention will be explained below. The ethylene/vinyl acetate copolymer of the present invention is
Known copolymers of ethylene and vinyl acetate (=
EVA), but it is a mixture of ordinary EVA and known plastics such as vinyl chloride, polyethylene, polycarbonate, and ethylene/propylene rubber, and adhesives such as ordinary EVA and rosin, paraffin, chlorinated diphenyl, neoprene, and nitrile rubber. Inorganic fillers such as calcium carbonate, magnesium hydroxide, aluminum hydroxide, calcium hydroxide, talc, clay, mica, wollastonite, copper,
Metals such as powders, fibers, flakes, etc. of iron, cobalt, nickel, chromium, manganese, aluminum, manganese or alloys of these metals, copper oxide, iron oxide,
Metal oxides such as powders, fibers and flakes such as antimony trioxide and lead oxide, organometallic compounds such as copper phthalocyanine (=phthalocyanine blue), yellow lead,
A composition containing pigments such as mineral violet, carbon black, red rose, ultramarine blue, cobalt blue, cobalt violet, and titanium white, as well as other plasticizers, flame retardants, ultraviolet absorbers, stabilizers, etc., and epoxy resins, etc. It is also effective as a composition containing a thermosetting resin,
These compositions are also included. Suitable monofunctional or polyfunctional cyanate ester compounds containing one or more cyanato groups in the molecule of the present invention to be added as a modifier to the EVA composition consisting of the above components are of the following general formula ( 1) General formula (1): R(OCN)m...(1) (m in the formula is an integer of 1 or more and usually 5 or less,
R is an aromatic organic group, and the cyanato group is bonded to the aromatic ring of the organic group. Specific examples include monocyanatobenzene, alkylcyanatobenzene such as P-tert-butylcyanatobenzene, monocyanatonaphthalene, 1,3- or 1,4-dicyanatobenzene, 1,3,5- Tricyanatobenzene, 1,3-, 1,4-, 1,6-, 1,8
-, 2,6- or 2,7-dicyanatonaphthalene, 1,3,6-tricyanatonaphthalene, 4,
4'-dicyanatobiphenyl, bis(4-dicyanatophenyl)methane, 2,2-bis(4-cyanatophenyl)propane, 2,2-bis(3,5-
dichloro-4-cyanatophenyl)propane,
2,2-bis(3,5-dibromo-4-cyanatophenyl)propane, bis(4-cyanatophenyl)ether, bis(4-cyanatophenyl)thioether, bis(4-cyanatophenyl)sulfone, tris(4-cyanatophenyl)phosphite, These include tris(4-cyanatophenyl) phosphate and cyanic acid esters obtained by reacting novolak with cyanogen halides. In addition to these, Tokuko Shou 41-1928, Sho 43-
18468, 44-4791, 45-11712, 46-41112,
Cyanic acid esters described in JP-A No. 47-26853 and JP-A No. 51-63149 can also be used. Alternatively, the above-mentioned polyfunctional cyanate ester may be polymerized as it is or in the presence of mineral acids, Lewis acids, salts such as sodium carbonate or lithium chloride, phosphoric acid esters such as tributylphosphine, organic metal salts, etc. The resulting molecule can be used as a prepolymer having a cyanato group, and can be used as a premix or prereactant with a monofunctional or polyfunctional maleimide compound (=
It can be used as a prepolymer), and can also be used as a prepolymer with an amine, which is a raw material for the maleimide compound described later. The amount of the cyanate ester compound of the present invention explained above in EVA is not particularly limited, but
The content is appropriately selected from the range of 0.1 to 20% by weight in terms of effectiveness. If the amount added is less than 0.1%, the property improvement effect will be insufficient, and if it is used in excess of 20% by weight,
It shows remarkable effects in preventing deterioration such as stability, but
This is undesirable because other properties such as a decrease in adhesive strength and a decrease in the elongation of EVA are impaired. Furthermore, as explained above, since a cyanato group is necessary for the effect of the present invention, additives that react with this functional group such as -OH, -COOH, -NH 2 , -COOM, -
When it is necessary to add a compound having - (M=metal atom) such as SH, it is preferable to avoid mixing the cyanate ester compound and these compounds in advance before adding them. The cross-linking catalyst for cross-linking EVA used as a reforming aid in the present invention includes, for example, known organic peroxides such as dicumyl peroxide, sulfur, these known catalysts and their co-catalysts such as iron acetylacetonate, Examples include combinations with known metal chelates and organic metal salts such as zinc octylate, and the usage amount is as follows:
Usually 0.1 to 5% by weight, based on the EVA composition, is suitable. Also, based on the EVA composition of the present invention, 0.1 to 5
% by weight of a monofunctional or polyfunctional maleimide compound can also be suitably used as a reforming aid alone or in combination with the above-mentioned crosslinking catalyst. Preferred compounds as such monofunctional or polyfunctional maleimide compounds are the following general formula (2) and general formula (2):
以下、実施例によつて本発明を説明する。尚、
実施例等中の部、％は重量基準である。
実施例 １
EVA（三井ポリケミカル(株)製、商品名；エバフ
レツクス＃250、酢酸ビニル含有率28％、メルト
インデツクス（＝MFR、ASTM D1238法）15
ｇ／10min）を90℃のロールで混合した後、
EVA100部に対して第１表に記載の如く、２，２
−ビス（４−シアナトフエニル）プロパン（以
下、BPA−CNと記す）、ビス（４−マレイミド
フエニルメタン（以下、BMと記す）、ロジン、
固形パラフイン（日本精蝋(株)性、145・Ｆパラフ
インワツクス）又はジクミルパーオキサイド（以
下、DCPOと記す）を加え、10分間ロールで混練
して得た混合物をプレスで温度100℃、30Kg／cm2、
１分間の条件で成形し、厚み0.3mmのフイルムを
製造した。
このフイルムを厚み100μｍのポリエチレンテ
レフタレートフイルムで挟み、30Kg／cm2、180℃、
３分間プレス成形しフイルム間を接着した。
この接着したフイルムの接着面の180゜方向の引
剥し強度（σs,180、単位Kg／25mm）を測定した結
果を第１表に示した。
The present invention will be explained below with reference to Examples. still,
Parts and percentages in Examples and the like are based on weight. Example 1 EVA (manufactured by Mitsui Polychemical Co., Ltd., trade name: Evaflex #250, vinyl acetate content 28%, melt index (=MFR, ASTM D1238 method) 15
g/10min) on a roll at 90°C,
As shown in Table 1 for 100 copies of EVA, 2,2
-Bis(4-cyanatophenyl)propane (hereinafter referred to as BPA-CN), bis(4-maleimidophenylmethane (hereinafter referred to as BM)), rosin,
Solid paraffin (manufactured by Nippon Seiro Co., Ltd., 145 F paraffin wax) or dicumyl peroxide (hereinafter referred to as DCPO) was added, and the mixture obtained by kneading with a roll for 10 minutes was heated in a press at a temperature of 100°C. 30Kg/ cm2 ,
Molding was performed for 1 minute to produce a film with a thickness of 0.3 mm. This film was sandwiched between 100 μm thick polyethylene terephthalate films, 30Kg/cm 2 , 180℃,
Press molding was performed for 3 minutes to bond the films together. Table 1 shows the results of measuring the peel strength (σ s,180 , unit: Kg/25 mm) of the bonded surface of the bonded film in the 180° direction.
【表】
実施例 ２
EVA（三井ポリケミカル(株)製、商品名；エバフ
レツクス＃40、酢酸ビニル含有率40％、MFR55
ｇ／10min）100部に、第２表に記載のBPA−
CN90部とBM10部とを140℃で２時間加熱予備反
応させた重量平均分子量1500のプレポリマー（以
下、BT−15と記す）、ジクミルパーオキサイド
（以下、DCPOと記す）を添加し、80℃のロール
で10分間混練し、次いで80℃のプレスで１分間、
５Kg／cm2で成形し、厚み150μｍのフイルムとし
た。
厚み100μｍのポリエチレンテレフタレートフ
イルムの間にそれぞれ上記で製造したフイルムを
挟み、５Kg／cm2、180℃、３分間プレス成形しフ
イルム間を接着し、フイルムの接着面の引剥し強
度を実施例１と同様にして測定した結果を第２表
に示した。[Table] Example 2 EVA (manufactured by Mitsui Polychemical Co., Ltd., product name: Evaflex #40, vinyl acetate content 40%, MFR55
g/10min) to 100 copies, add BPA- listed in Table 2.
A prepolymer with a weight average molecular weight of 1500 (hereinafter referred to as BT-15) prepared by pre-reacting 90 parts of CN and 10 parts of BM by heating at 140°C for 2 hours, dicumyl peroxide (hereinafter referred to as DCPO) was added, and 80 Knead for 10 minutes with a roll at 80℃, then knead for 1 minute with a press at 80℃.
It was molded at 5 kg/cm 2 to form a film with a thickness of 150 μm. The films produced above were sandwiched between polyethylene terephthalate films with a thickness of 100 μm, and press-molded at 5 kg/cm 2 at 180°C for 3 minutes to adhere the films. The results measured in the same manner are shown in Table 2.
【表】
実施例 ３
実施例２の試験No.と同様にして得たロール混
練組成物を80℃のトルエン中で溶解し、固形分濃
度25％の溶液とした。
この溶液を厚み100μｍのアルミニウム箔の片
面に塗布し130℃で５分間乾燥し厚み60μｍの塗
膜を形成した。この箔の塗膜面側に厚み100μｍ
のアルミニウム箔を重ね160℃、圧力５Kg／cm2で
15分間プレスした後、引剥し強度を実施例１と同
様にして測定したところ、11Kg／25mmであつた。
実施例 ４
EVA（三井ポリケミカル(株)製、商品名；エバフ
レツクス＃220、酢酸ビニル含有率28％、
MFR150ｇ／10min）に、実施例１で使用したと
同様のロジン、固形パラフイン、実施例２で使用
したと同様のBT−15、DCPOを第３表の如く添
加し、70℃のロールで10分間混練して得た混合物
を180℃のＴダイより厚み60μｍで押し出し、厚
み50μｍの鉄箔上にのせて厚み60μｍの層を形成
し、直ちに厚み50μｍの鉄箔を重ね、180℃の25
Kg／cmのロール間を１ｍ／minの速度で通過させ
室温下に放置した。
引剥し強度を実施例１と同様にして測定した結
果を第３表に示した。[Table] Example 3 A roll-kneaded composition obtained in the same manner as Test No. of Example 2 was dissolved in toluene at 80°C to form a solution with a solid content concentration of 25%. This solution was applied to one side of aluminum foil with a thickness of 100 μm and dried at 130° C. for 5 minutes to form a coating film with a thickness of 60 μm. The coating side of this foil has a thickness of 100 μm.
layered with aluminum foil at 160℃ and pressure 5Kg/ cm2.
After pressing for 15 minutes, the peel strength was measured in the same manner as in Example 1 and found to be 11 kg/25 mm. Example 4 EVA (manufactured by Mitsui Polychemical Co., Ltd., trade name: Evaflex #220, vinyl acetate content 28%,
MFR150g/10min), rosin similar to that used in Example 1, solid paraffin, BT-15 similar to that used in Example 2, and DCPO were added as shown in Table 3, and heated with a roll at 70℃ for 10 minutes. The mixture obtained by kneading was extruded to a thickness of 60 μm through a T-die at 180°C, placed on a 50 μm thick iron foil to form a 60 μm thick layer, immediately overlaid with a 50 μm thick iron foil, and heated to a temperature of 25°C at 180°C.
The sample was passed between rolls of kg/cm at a speed of 1 m/min and left at room temperature. The peel strength was measured in the same manner as in Example 1, and the results are shown in Table 3.
【表】
実施例 ５
EVA（商品名；エバフレツクス＃150）100部
に、第４表に記載のBPA−CN90部とBM10部と
を140℃で４時間加熱予備反応させた重量平均分
子量2000のプレポリマー（以下、BT−20と記
す）及びベンゾイルパーオキサイド（以下、
BPOと記す）を添加し、80℃のロールで８分間
混練し、次いで80℃のプレスで１分間、20Kg／cm2
で成形し、厚み150μｍのフイルムとした。
厚み100μｍのアルミニウム箔、厚み50μｍの銅
箔、ポリカーボネートフイルム、ポリスルホンフ
イルム及びポリイミドフイルムの間にそれぞれ上
記で製造したフイルムを挟み、20Kg／cm2、160℃、
３分間プレス成形しフイルム間を接着した。
実施例１と同様に引剥し強度を測定した結果を
第４表に示した。[Table] Example 5 100 parts of EVA (trade name: Evaflex #150) was heated and pre-reacted with 90 parts of BPA-CN and 10 parts of BM listed in Table 4 at 140°C for 4 hours to prepare a preform with a weight average molecular weight of 2000. Polymer (hereinafter referred to as BT-20) and benzoyl peroxide (hereinafter referred to as
20Kg/cm 2
It was molded into a film with a thickness of 150 μm. The films produced above were sandwiched between 100 μm thick aluminum foil, 50 μm thick copper foil, polycarbonate film, polysulfone film, and polyimide film, respectively, at 20 kg/cm 2 at 160°C.
Press molding was performed for 3 minutes to bond the films together. The peel strength was measured in the same manner as in Example 1, and the results are shown in Table 4.
以上、詳細な説明および実施例等から明らかな
如く、本発明の組成物は、機械的物性や熱的物性
の向上の他、特に、接着用フイルムとして使用し
た場合、極めて優れた接着力を示すことなど、実
用上極めて優れた組成物であることがわかる。
As is clear from the above detailed description and examples, the composition of the present invention not only has improved mechanical properties and thermal properties, but also exhibits extremely excellent adhesive strength especially when used as an adhesive film. It can be seen that the composition is extremely excellent in practical use.
Claims (1)
シアナト基を１個以上含有する単官能性もしくは
多官能性シアン酸エステル化合物を0.1〜20重量
％混合してなる接着性の改質されたエチレン・酢
酸ビニル共重合体組成物。 ２ 該シアン酸エステル化合物による接着性の改
質を促進する改質用助剤として、該エチレン・酢
酸ビニル共重合体組成物の架橋触媒又は単官能性
もしくは多官能性マレイミド化合物を該エチレ
ン・酢酸ビニル共重合体を基準として0.1〜５重
量％併用する特許請求の範囲第１項記載のエチレ
ン・酢酸ビニル共重合体組成物。[Claims] 1. Adhesive properties obtained by mixing ethylene/vinyl acetate copolymer with 0.1 to 20% by weight of a monofunctional or polyfunctional cyanate ester compound containing one or more cyanato groups in the molecule. A modified ethylene-vinyl acetate copolymer composition. 2. A crosslinking catalyst for the ethylene/vinyl acetate copolymer composition or a monofunctional or polyfunctional maleimide compound is used as a modification aid for promoting adhesive modification by the cyanate ester compound. The ethylene/vinyl acetate copolymer composition according to claim 1, wherein the ethylene/vinyl acetate copolymer composition is used in an amount of 0.1 to 5% by weight based on the vinyl copolymer.
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21925485A JPS6279245A (en) | 1985-10-03 | 1985-10-03 | Ethylene-vinyl acetate copolymer composition |
| DE3633777A DE3633777C2 (en) | 1985-10-03 | 1986-10-03 | Hot melt adhesive composition |
| US07/118,910 US4820769A (en) | 1985-10-03 | 1987-11-10 | Hot melt adhesive composition |
| US07/235,814 US4871811A (en) | 1985-10-03 | 1988-08-23 | Hot melt adhesive composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP21925485A JPS6279245A (en) | 1985-10-03 | 1985-10-03 | Ethylene-vinyl acetate copolymer composition |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| JPS6279245A JPS6279245A (en) | 1987-04-11 |
| JPH0582855B2 true JPH0582855B2 (en) | 1993-11-22 |
Family
ID=16732636
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP21925485A Granted JPS6279245A (en) | 1985-10-03 | 1985-10-03 | Ethylene-vinyl acetate copolymer composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS6279245A (en) |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP2007031515A (en) * | 2005-07-25 | 2007-02-08 | Yokohama Rubber Co Ltd:The | Manufacturing method of adhesive composition |
-
1985
- 1985-10-03 JP JP21925485A patent/JPS6279245A/en active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS6279245A (en) | 1987-04-11 |
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