CN114045145A - Adhesive composition - Google Patents
Adhesive composition Download PDFInfo
- Publication number
- CN114045145A CN114045145A CN202111368795.8A CN202111368795A CN114045145A CN 114045145 A CN114045145 A CN 114045145A CN 202111368795 A CN202111368795 A CN 202111368795A CN 114045145 A CN114045145 A CN 114045145A
- Authority
- CN
- China
- Prior art keywords
- adhesive composition
- acid
- copolyester
- mol
- laminate
- 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.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 99
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 99
- 239000000203 mixture Substances 0.000 title claims abstract description 92
- 229920001634 Copolyester Polymers 0.000 claims abstract description 64
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 23
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 22
- 150000002009 diols Chemical class 0.000 claims abstract description 21
- 229920001515 polyalkylene glycol Polymers 0.000 claims abstract description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims abstract description 13
- 239000002253 acid Substances 0.000 claims abstract description 12
- 239000000243 solution Substances 0.000 description 29
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 27
- -1 polyethylene terephthalate Polymers 0.000 description 22
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 18
- 230000000052 comparative effect Effects 0.000 description 15
- 239000010410 layer Substances 0.000 description 14
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical group OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 13
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 12
- 239000010408 film Substances 0.000 description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 11
- 239000002904 solvent Substances 0.000 description 11
- 230000009477 glass transition Effects 0.000 description 10
- 229910052751 metal Inorganic materials 0.000 description 10
- 239000002184 metal Substances 0.000 description 10
- 239000003960 organic solvent Substances 0.000 description 10
- 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 10
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 9
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- 239000012948 isocyanate Substances 0.000 description 9
- 238000006068 polycondensation reaction Methods 0.000 description 8
- 239000012790 adhesive layer Substances 0.000 description 7
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 7
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 150000002513 isocyanates Chemical class 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 5
- 150000001875 compounds Chemical class 0.000 description 5
- 238000005886 esterification reaction Methods 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 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 5
- 238000004519 manufacturing process Methods 0.000 description 5
- 150000002739 metals Chemical class 0.000 description 5
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- 239000011889 copper foil Substances 0.000 description 4
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 4
- 239000012046 mixed solvent Substances 0.000 description 4
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 4
- 239000002994 raw material Substances 0.000 description 4
- 229920005989 resin Polymers 0.000 description 4
- 239000011347 resin Substances 0.000 description 4
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 4
- FKTHNVSLHLHISI-UHFFFAOYSA-N 1,2-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=CC=C1CN=C=O FKTHNVSLHLHISI-UHFFFAOYSA-N 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 229940035437 1,3-propanediol Drugs 0.000 description 3
- GHKOFFNLGXMVNJ-UHFFFAOYSA-N Didodecyl thiobispropanoate Chemical compound CCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCC GHKOFFNLGXMVNJ-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000005058 Isophorone diisocyanate Substances 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000003963 antioxidant agent Substances 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 238000000576 coating method Methods 0.000 description 3
- 229910052802 copper Inorganic materials 0.000 description 3
- 239000010949 copper Substances 0.000 description 3
- 239000003063 flame retardant Substances 0.000 description 3
- 125000000524 functional group Chemical group 0.000 description 3
- 239000012760 heat stabilizer Substances 0.000 description 3
- ZFSLODLOARCGLH-UHFFFAOYSA-N isocyanuric acid Chemical compound OC1=NC(O)=NC(O)=N1 ZFSLODLOARCGLH-UHFFFAOYSA-N 0.000 description 3
- 229920001225 polyester resin Polymers 0.000 description 3
- 239000004645 polyester resin Substances 0.000 description 3
- 229920001223 polyethylene glycol Polymers 0.000 description 3
- 229920000139 polyethylene terephthalate Polymers 0.000 description 3
- 239000005020 polyethylene terephthalate Substances 0.000 description 3
- 238000006116 polymerization reaction Methods 0.000 description 3
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 3
- 239000007787 solid Substances 0.000 description 3
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 2
- KBPLFHHGFOOTCA-UHFFFAOYSA-N 1-Octanol Chemical compound CCCCCCCCO KBPLFHHGFOOTCA-UHFFFAOYSA-N 0.000 description 2
- PAZZVPKITDJCPV-UHFFFAOYSA-N 10-hydroxyoctadecanoic acid Chemical compound CCCCCCCCC(O)CCCCCCCCC(O)=O PAZZVPKITDJCPV-UHFFFAOYSA-N 0.000 description 2
- RNFJDJUURJAICM-UHFFFAOYSA-N 2,2,4,4,6,6-hexaphenoxy-1,3,5-triaza-2$l^{5},4$l^{5},6$l^{5}-triphosphacyclohexa-1,3,5-triene Chemical compound N=1P(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP(OC=2C=CC=CC=2)(OC=2C=CC=CC=2)=NP=1(OC=1C=CC=CC=1)OC1=CC=CC=C1 RNFJDJUURJAICM-UHFFFAOYSA-N 0.000 description 2
- BWLBGMIXKSTLSX-UHFFFAOYSA-N 2-hydroxyisobutyric acid Chemical compound CC(C)(O)C(O)=O BWLBGMIXKSTLSX-UHFFFAOYSA-N 0.000 description 2
- WHBMMWSBFZVSSR-UHFFFAOYSA-N 3-hydroxybutyric acid Chemical compound CC(O)CC(O)=O WHBMMWSBFZVSSR-UHFFFAOYSA-N 0.000 description 2
- REKYPYSUBKSCAT-UHFFFAOYSA-N 3-hydroxypentanoic acid Chemical compound CCC(O)CC(O)=O REKYPYSUBKSCAT-UHFFFAOYSA-N 0.000 description 2
- 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 2
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 description 2
- FMHKPLXYWVCLME-UHFFFAOYSA-N 4-hydroxy-valeric acid Chemical compound CC(O)CCC(O)=O FMHKPLXYWVCLME-UHFFFAOYSA-N 0.000 description 2
- QNVNLUSHGRBCLO-UHFFFAOYSA-N 5-hydroxybenzene-1,3-dicarboxylic acid Chemical compound OC(=O)C1=CC(O)=CC(C(O)=O)=C1 QNVNLUSHGRBCLO-UHFFFAOYSA-N 0.000 description 2
- OZJPLYNZGCXSJM-UHFFFAOYSA-N 5-valerolactone Chemical compound O=C1CCCCO1 OZJPLYNZGCXSJM-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 239000002656 Distearyl thiodipropionate Substances 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- AEMRFAOFKBGASW-UHFFFAOYSA-N Glycolic acid Chemical compound OCC(O)=O AEMRFAOFKBGASW-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 2
- 239000002202 Polyethylene glycol Substances 0.000 description 2
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 2
- 239000007983 Tris buffer Substances 0.000 description 2
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- LJCFOYOSGPHIOO-UHFFFAOYSA-N antimony pentoxide Chemical compound O=[Sb](=O)O[Sb](=O)=O LJCFOYOSGPHIOO-UHFFFAOYSA-N 0.000 description 2
- 230000003078 antioxidant effect Effects 0.000 description 2
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- DKPFZGUDAPQIHT-UHFFFAOYSA-N butyl acetate Chemical compound CCCCOC(C)=O DKPFZGUDAPQIHT-UHFFFAOYSA-N 0.000 description 2
- 239000011248 coating agent Substances 0.000 description 2
- 239000000470 constituent Substances 0.000 description 2
- JHIVVAPYMSGYDF-UHFFFAOYSA-N cyclohexanone Chemical compound O=C1CCCCC1 JHIVVAPYMSGYDF-UHFFFAOYSA-N 0.000 description 2
- MWKFXSUHUHTGQN-UHFFFAOYSA-N decan-1-ol Chemical compound CCCCCCCCCCO MWKFXSUHUHTGQN-UHFFFAOYSA-N 0.000 description 2
- XBDQKXXYIPTUBI-UHFFFAOYSA-N dimethylselenoniopropionate Natural products CCC(O)=O XBDQKXXYIPTUBI-UHFFFAOYSA-N 0.000 description 2
- PWWSSIYVTQUJQQ-UHFFFAOYSA-N distearyl thiodipropionate Chemical compound CCCCCCCCCCCCCCCCCCOC(=O)CCSCCC(=O)OCCCCCCCCCCCCCCCCCC PWWSSIYVTQUJQQ-UHFFFAOYSA-N 0.000 description 2
- 235000019305 distearyl thiodipropionate Nutrition 0.000 description 2
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 238000011156 evaluation Methods 0.000 description 2
- BXWNKGSJHAJOGX-UHFFFAOYSA-N hexadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCO BXWNKGSJHAJOGX-UHFFFAOYSA-N 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- ZXEKIIBDNHEJCQ-UHFFFAOYSA-N isobutanol Chemical compound CC(C)CO ZXEKIIBDNHEJCQ-UHFFFAOYSA-N 0.000 description 2
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- 238000005259 measurement Methods 0.000 description 2
- 150000002762 monocarboxylic acid derivatives Chemical class 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- RPBCDDTWDKYNQY-UHFFFAOYSA-N o-dodecyl propanethioate Chemical compound CCCCCCCCCCCCOC(=S)CC RPBCDDTWDKYNQY-UHFFFAOYSA-N 0.000 description 2
- GLDOVTGHNKAZLK-UHFFFAOYSA-N octadecan-1-ol Chemical compound CCCCCCCCCCCCCCCCCCO GLDOVTGHNKAZLK-UHFFFAOYSA-N 0.000 description 2
- NFHFRUOZVGFOOS-UHFFFAOYSA-N palladium;triphenylphosphane Chemical compound [Pd].C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1.C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 NFHFRUOZVGFOOS-UHFFFAOYSA-N 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 239000005056 polyisocyanate Substances 0.000 description 2
- 229920001228 polyisocyanate Polymers 0.000 description 2
- CYIDZMCFTVVTJO-UHFFFAOYSA-N pyromellitic acid Chemical compound OC(=O)C1=CC(C(O)=O)=C(C(O)=O)C=C1C(O)=O CYIDZMCFTVVTJO-UHFFFAOYSA-N 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- HLZKNKRTKFSKGZ-UHFFFAOYSA-N tetradecan-1-ol Chemical compound CCCCCCCCCCCCCCO HLZKNKRTKFSKGZ-UHFFFAOYSA-N 0.000 description 2
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 2
- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 2
- RSJKGSCJYJTIGS-UHFFFAOYSA-N undecane Chemical compound CCCCCCCCCCC RSJKGSCJYJTIGS-UHFFFAOYSA-N 0.000 description 2
- 239000004246 zinc acetate Substances 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- OQLRBFNNEQUJPK-UHFFFAOYSA-N (3,5-ditert-butyl-4-hydroxyphenyl)methyl diethyl phosphate Chemical compound CCOP(=O)(OCC)OCC1=CC(C(C)(C)C)=C(O)C(C(C)(C)C)=C1 OQLRBFNNEQUJPK-UHFFFAOYSA-N 0.000 description 1
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- AFENDNXGAFYKQO-VKHMYHEASA-N (S)-2-hydroxybutyric acid Chemical compound CC[C@H](O)C(O)=O AFENDNXGAFYKQO-VKHMYHEASA-N 0.000 description 1
- BJEPYKJPYRNKOW-REOHCLBHSA-N (S)-malic acid Chemical compound OC(=O)[C@@H](O)CC(O)=O BJEPYKJPYRNKOW-REOHCLBHSA-N 0.000 description 1
- BZQKBFHEWDPQHD-UHFFFAOYSA-N 1,2,3,4,5-pentabromo-6-[2-(2,3,4,5,6-pentabromophenyl)ethyl]benzene Chemical compound BrC1=C(Br)C(Br)=C(Br)C(Br)=C1CCC1=C(Br)C(Br)=C(Br)C(Br)=C1Br BZQKBFHEWDPQHD-UHFFFAOYSA-N 0.000 description 1
- JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
- DEIGXXQKDWULML-UHFFFAOYSA-N 1,2,5,6,9,10-hexabromocyclododecane Chemical compound BrC1CCC(Br)C(Br)CCC(Br)C(Br)CCC1Br DEIGXXQKDWULML-UHFFFAOYSA-N 0.000 description 1
- YAOMHRRYSRRRKP-UHFFFAOYSA-N 1,2-dichloropropyl 2,3-dichloropropyl 3,3-dichloropropyl phosphate Chemical compound ClC(Cl)CCOP(=O)(OC(Cl)C(Cl)C)OCC(Cl)CCl YAOMHRRYSRRRKP-UHFFFAOYSA-N 0.000 description 1
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- CMQUQOHNANGDOR-UHFFFAOYSA-N 2,3-dibromo-4-(2,4-dibromo-5-hydroxyphenyl)phenol Chemical compound BrC1=C(Br)C(O)=CC=C1C1=CC(O)=C(Br)C=C1Br CMQUQOHNANGDOR-UHFFFAOYSA-N 0.000 description 1
- SPSPIUSUWPLVKD-UHFFFAOYSA-N 2,3-dibutyl-6-methylphenol Chemical compound CCCCC1=CC=C(C)C(O)=C1CCCC SPSPIUSUWPLVKD-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- BVDAXFBFXWOHHU-UHFFFAOYSA-N 2-(4-hydroxyphenyl)octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(C(O)=O)C1=CC=C(O)C=C1 BVDAXFBFXWOHHU-UHFFFAOYSA-N 0.000 description 1
- QSRJVOOOWGXUDY-UHFFFAOYSA-N 2-[2-[2-[3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoyloxy]ethoxy]ethoxy]ethyl 3-(3-tert-butyl-4-hydroxy-5-methylphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C)=CC(CCC(=O)OCCOCCOCCOC(=O)CCC=2C=C(C(O)=C(C)C=2)C(C)(C)C)=C1 QSRJVOOOWGXUDY-UHFFFAOYSA-N 0.000 description 1
- XDZMPRGFOOFSBL-UHFFFAOYSA-N 2-ethoxybenzoic acid Chemical compound CCOC1=CC=CC=C1C(O)=O XDZMPRGFOOFSBL-UHFFFAOYSA-N 0.000 description 1
- SVONRAPFKPVNKG-UHFFFAOYSA-N 2-ethoxyethyl acetate Chemical compound CCOCCOC(C)=O SVONRAPFKPVNKG-UHFFFAOYSA-N 0.000 description 1
- WVQHODUGKTXKQF-UHFFFAOYSA-N 2-ethyl-2-methylhexane-1,1-diol Chemical compound CCCCC(C)(CC)C(O)O WVQHODUGKTXKQF-UHFFFAOYSA-N 0.000 description 1
- MBIQENSCDNJOIY-UHFFFAOYSA-N 2-hydroxy-2-methylbutyric acid Chemical compound CCC(C)(O)C(O)=O MBIQENSCDNJOIY-UHFFFAOYSA-N 0.000 description 1
- JRHWHSJDIILJAT-UHFFFAOYSA-N 2-hydroxypentanoic acid Chemical compound CCCC(O)C(O)=O JRHWHSJDIILJAT-UHFFFAOYSA-N 0.000 description 1
- QOFLTGDAZLWRMJ-UHFFFAOYSA-N 2-methylpropane-1,1-diol Chemical compound CC(C)C(O)O QOFLTGDAZLWRMJ-UHFFFAOYSA-N 0.000 description 1
- QCDWFXQBSFUVSP-UHFFFAOYSA-N 2-phenoxyethanol Chemical compound OCCOC1=CC=CC=C1 QCDWFXQBSFUVSP-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
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- 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
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- 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
- C09J175/00—Adhesives based on polyureas or polyurethanes; Adhesives based on derivatives of such polymers
- C09J175/04—Polyurethanes
- C09J175/06—Polyurethanes from polyesters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/09—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyesters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/40—High-molecular-weight compounds
- C08G18/42—Polycondensates having carboxylic or carbonic ester groups in the main chain
- C08G18/4244—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups
- C08G18/4247—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids
- C08G18/4252—Polycondensates having carboxylic or carbonic ester groups in the main chain containing oxygen in the form of ether groups derived from polyols containing at least one ether group and polycarboxylic acids derived from polyols containing polyether groups and polycarboxylic acids
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/02—Disposition of insulation
- H01B7/0208—Cables with several layers of insulating material
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/04—Flexible cables, conductors, or cords, e.g. trailing cables
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
- H01B7/00—Insulated conductors or cables characterised by their form
- H01B7/08—Flat or ribbon cables
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Laminated Bodies (AREA)
- Insulated Conductors (AREA)
- Adhesive Tapes (AREA)
Abstract
The present invention provides an adhesive composition comprising 100 parts by mass of a copolyester and 0.2 to 15 parts by mass of a curing agent, wherein the content of isophthalic acid in an acid component of the copolyester is 30 mol% or more, the content of a diol having a side chain in a diol component of the copolyester is 30 mol% or more, the content of a polyalkylene glycol having 2 to 4 carbon atoms in a repeating unit is 1 to 20 mol%, and the softening point of the adhesive composition is 90 ℃ or more.
Description
The application is a divisional application of patent application 201780018888.3 (application date: 2017, 04, 13, title of invention: adhesive composition).
Technical Field
The present invention relates to an adhesive composition and a laminate having a layer composed of the adhesive composition.
Background
Polyester resins represented by polyethylene terephthalate and polybutylene terephthalate are widely used in various fields as fibers, films, molding materials, and the like, taking advantage of their excellent mechanical strength, thermal stability, hydrophobicity, and chemical resistance.
Polyester resins are copolymerized with various characteristics by changing the types of dicarboxylic acids and diols as the constituent components.
In general, a copolyester resin is widely used for an adhesive, a coating agent, an ink binder, a paint, and the like because of its excellent adhesion to plastics such as polyester, polycarbonate, and a polyvinyl chloride resin, or metals such as aluminum and copper. For example, patent document 1 discloses a polyester resin excellent in adhesiveness obtained by copolymerizing a specific alkylene glycol.
Further, since the copolyester adhesive is excellent in properties such as electrical insulation, flame retardancy, and flexibility (peeling resistance at a bent portion), it is widely used for flexible flat cables and the like which are widely used as wiring materials for digital home appliances and automobiles, for example.
The flexible flat cable has a structure in which 2 insulating films each composed of 2 layers of a base film and an adhesive layer are bonded to each other with the adhesive layer sides facing each other with a lead wire interposed therebetween. Polyethylene terephthalate films are often used as base films, and metals such as copper or copper with tin-plated surfaces are often used as wires.
In particular, in recent years, in flexible flat cables used for small-sized home appliances and vehicle-mounted components which are thinned and miniaturized, the influence of heat radiation from a backlight of a liquid crystal, a CPU, and the like cannot be ignored, and resistance to heat is becoming a necessary condition, and in some cases, the flexible flat cables are used outdoors, and therefore, an adhesive constituting the flexible flat cables is also required to have moist heat resistance which can maintain adhesion without peeling off an adhesive interface even under high temperature and high humidity.
Documents of the prior art
Patent document
Patent document 1: japanese patent laid-open publication No. 2001-200041
Disclosure of Invention
The purpose of the present invention is to provide an adhesive composition that has excellent adhesion to metals and excellent heat resistance and moist heat resistance, and a laminate having a layer made of the adhesive composition.
The present inventors have made intensive studies to solve the above problems, and as a result, have found that an adhesive composition containing a copolyester having a specific structure and a crosslinking agent is excellent in adhesion to a metal and also excellent in heat resistance and moist heat resistance, and have completed the present invention.
That is, the gist of the present invention is as follows.
(1) An adhesive composition characterized by comprising 100 parts by mass of a copolyester and 0.2 to 15 parts by mass of a curing agent,
the content of isophthalic acid in the acid component of the copolyester is 30 mol% or more,
the content of the diol having a side chain in the diol component of the copolyester is 30 mol% or more, and the content of the polyalkylene glycol having a repeating unit of 2 to 4 carbon atoms is 1 to 20 mol%,
the softening point of the adhesive composition is 90 ℃ or higher.
(2) The adhesive composition according to (1), wherein the polyalkylene glycol is composed of 2 or more species, and at least 1 species has a number average molecular weight of 200 or more.
(3) A laminate comprising a layer composed of the adhesive composition according to the above (1) or (2).
(4) A flexible flat cable comprising the laminate according to the item (3).
According to the present invention, an adhesive composition having excellent adhesion to metals, and having excellent heat resistance and moist heat resistance can be provided. The laminate having the layer composed of the adhesive composition can be used as a constituent member of a flexible flat cable.
Detailed Description
The adhesive composition of the present invention comprises a copolyester having a softening point of 90 ℃ or higher and a curing agent, wherein the copolyester contains isophthalic acid as an acid component, and contains a diol having a side chain and a polyalkylene glycol having 2 to 4 carbon atoms as a repeating unit as a diol component.
The copolyester constituting the adhesive composition of the present invention contains 30 mol% or more of isophthalic acid as an acid component, preferably 40 mol% or more, and more preferably 50 to 80 mol%. If the content of isophthalic acid in the acid component is less than 30 mol%, the obtained adhesive composition tends to have a reduced adhesiveness and a reduced solubility in organic solvents.
Examples of the acid component other than isophthalic acid include terephthalic acid, naphthalenedicarboxylic acid, succinic acid, adipic acid, azelaic acid, sebacic acid, hexahydroterephthalic acid, phthalic acid, 4' -dicarboxybiphenyl, isophthalic acid 5-sodium sulfonate, 5-hydroxy-isophthalic acid, fumaric acid, maleic acid, itaconic acid, mesaconic acid, citraconic acid, 1,3, 4-benzenetricarboxylic acid, 1,2,4, 5-benzenetetracarboxylic acid, oxalic acid, 1, 3-cyclohexanedicarboxylic acid, 1, 2-cyclohexanedicarboxylic acid, and 2, 5-norbornenedicarboxylic acid. These may be used as the monomer raw material or in combination. Among them, terephthalic acid, naphthalenedicarboxylic acid and hexahydroterephthalic acid are preferably used as acid components other than isophthalic acid from the viewpoint of maintaining heat resistance.
In the copolyester, the diol component needs to contain 30 mol% or more of a diol having a side chain, more preferably 40 mol% or more, and still more preferably 50 to 80 mol%. If the content of the diol having a side chain in the diol component is less than 30 mol%, the obtained adhesive composition tends to have reduced adhesiveness and reduced solubility in an organic solvent. On the other hand, if the content of the diol having a side chain exceeds 80 mol%, the adhesive composition tends to have a reduced adhesiveness.
Examples of the diol having a side chain include 1, 2-propanediol, 2-dimethyl-1, 3-propanediol (neopentyl glycol), 2-methylpropanediol, 3-methyl-1, 5-pentanediol, 2-ethyl-2-butylpropanediol, an ethylene oxide adduct of bisphenol a, a propylene oxide adduct of bisphenol a, trimethylolpropane, and the like, and these may be used in combination. Among these, 2-dimethyl-1, 3-propanediol (neopentyl glycol) and an ethylene oxide adduct of bisphenol a are preferable as the diol having a side chain from the viewpoint of improving adhesiveness.
In the copolyester, the diol component preferably contains 1 to 20 mol% of a polyalkylene glycol having 2 to 4 carbon atoms and having a repeating unit, preferably 3 to 15 mol%, more preferably 4 to 10 mol%. When the content of the polyalkylene glycol having a repeating unit of 2 to 4 carbon atoms in the glycol component is less than 1 mol%, the wet heat resistance of the obtained adhesive composition is lowered. Further, the glass transition point of the copolyester tends to be high, and the adhesiveness of the resulting adhesive composition may be lowered. On the other hand, if the content of the polyalkylene glycol having 2 to 4 carbon atoms in the repeating unit exceeds 20 mol%, the softening point of the resulting adhesive composition is lowered and the heat resistance is poor.
The polyalkylene glycol having 2 to 4 carbon atoms as the repeating unit is preferably diethylene glycol, triethylene glycol, tetraethylene glycol, polyethylene glycol, polypropylene glycol, polytrimethylene glycol, or polytetramethylene glycol from the viewpoint of adhesiveness and moist heat resistance.
The copolyester preferably uses a polyalkylene glycol having 2 to 4 carbon atoms and a number average molecular weight of 200 or more as a repeating unit. Among them, polyalkylene glycol having a number average molecular weight of 500 to 10000 is more preferably used, and polyalkylene glycol having a number average molecular weight of 800 to 5000 is further preferably used. The adhesive composition obtained by using a copolyester having a number average molecular weight of 200 or more of a polyalkylene glycol having 2 to 4 carbon atoms as a repeating unit has improved wet heat resistance.
Further, the copolyester preferably contains, as a diol component, 2 or more kinds of polyalkylene glycol having 2 to 4 carbon atoms as a repeating unit. This can improve the adhesiveness of the adhesive composition. Among them, in the case of using 2 kinds of polyalkylene glycols, it is preferable to use polytetramethylene glycol and diethylene glycol in combination, and further, it is preferable to use polytetramethylene glycol and triethylene glycol in combination.
Examples of the diol component other than those described above include ethylene glycol, 1, 3-propanediol, 1, 4-butanediol, 1, 5-pentanediol, 1, 6-hexanediol, 1, 4-cyclohexanedimethanol, and the like, and 2 or more kinds of these may be used in combination.
Further, as other components constituting the copolyester, there may be mentioned tetrahydrophthalic acid, lactic acid, ethylene oxide, glycolic acid, 2-hydroxybutyric acid, 3-hydroxybutyric acid, 4-hydroxybutyric acid, 2-hydroxyisobutyric acid, 2-hydroxy-2-methylbutyric acid, 2-hydroxyvaleric acid, 3-hydroxyvaleric acid, 4-hydroxyvaleric acid, 5-hydroxyvaleric acid, 6-hydroxyhexanoic acid, 10-hydroxystearic acid, hydroxycarboxylic acids such as 4- (. beta. -hydroxy) ethoxybenzoic acid, malic acid, beta-propiolactone, beta-butyrolactone, gamma-butyrolactone, delta-valerolactone, and aliphatic lactones such as. epsilon. -caprolactone, and these components may be contained.
The copolyester may be copolymerized with a monocarboxylic acid and a monohydric alcohol, if necessary. Examples of the monocarboxylic acid include lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, linoleic acid, linolenic acid, benzoic acid, p-tert-butylbenzoic acid, cyclohexanoic acid, and 4-hydroxyphenylstearic acid, and examples of the monohydric alcohol include octanol, decanol, lauryl alcohol, myristyl alcohol, cetyl alcohol, stearyl alcohol, and 2-phenoxyethanol.
The above-mentioned monomers constituting the copolyester may be used in combination in a plurality of kinds depending on the properties to be imparted.
The copolyester may be used in a mixture of 2 or more, and may be phase-separated or uniformly mixed.
The glass transition point of the copolyester is preferably 50 ℃ or lower, more preferably 40 ℃ or lower, and further preferably 30 ℃ or lower. When the glass transition point of the copolyester exceeds 50 ℃, the adhesion of the resulting adhesive composition to metal may be reduced.
The glass transition point is preferably-40 ℃ or higher, more preferably-20 ℃ or higher, and still more preferably 0 ℃ or higher. When the glass transition point of the copolyester is less than-40 ℃, the copolyester may have strong adhesiveness and may be difficult to handle.
The adhesive composition of the present invention needs to contain a curing agent in an amount of 0.2 to 15 parts by mass, preferably 0.4 to 10 parts by mass, and more preferably 0.4 to 5.0 parts by mass, based on 100 parts by mass of the copolyester. By adding the curing agent, heat resistance and moist heat resistance can be improved. If the content of the curing agent is less than 0.2 parts by mass, the heat resistance and the moist heat resistance of the obtained adhesive composition are lowered, while if the content exceeds 15 parts by mass, the adhesiveness of the obtained adhesive composition is lowered.
The adhesive composition of the present invention is formed into a layer composed of an adhesive composition by applying a liquid or paste adhesive to an adherend 1, bonding the same or different kinds of adherends 2, and then scattering a solvent or water to cure (harden) the adhesive component. Depending on the application, there is a case where the adherend 2 is bonded by heat treatment after the adherend 1 is formed with a layer made of the adhesive composition (embodiment 1); and a case where the adherend 2 is bonded without heat treatment after the adherend 1 is formed with the layer made of the adhesive composition (embodiment 2). The adhesive composition of the present invention is excellent in adhesiveness particularly when used in embodiment 2. When used in the embodiment 1, the content of the curing agent is preferably 0.4 to 5.0 parts by mass per 100 parts by mass of the copolyester.
The content of the curing agent is preferably 0.2 to 2, more preferably 0.4 to 1.5, and still more preferably 0.5 to 0.9 in terms of the equivalent ratio of the functional groups of the curing agent to the total of the functional groups (carboxyl group and hydroxyl group) of the copolyester. When the equivalent ratio is less than 0.2, the heat resistance of the adhesive composition is lowered, and when the equivalent ratio exceeds 2, the adhesiveness may be lowered.
The curing agent is a substance having a functional group capable of reacting with a hydroxyl group or a carboxyl group of the copolyester, and examples thereof include an isocyanate compound, an epoxy compound, a carbodiimide compound, a carboxyl group, a carboxyl,
Oxazoline compounds and the like, these compounds may be appropriately combined, and isocyanate compounds are preferably used from the viewpoint of reactivity and handling property.
As the isocyanate compound, aromatic diisocyanates such as Tolylene Diisocyanate (TDI), diphenylmethane diisocyanate (MDI) and Xylylene Diisocyanate (XDI), and aliphatic or alicyclic diisocyanates such as hydrogenated TDI, hydrogenated MDI, hydrogenated XDI, Hexamethylene Diisocyanate (HDI) and isophorone diisocyanate (IPDI) are useful in having both adhesiveness to metal and heat resistance. These diisocyanates may be used as derivatives such as polyisocyanates having an isocyanurate, biuret or adduct structure, polymethylene polyphenyl polyisocyanates, and carbodiimide modified products.
Among them, Tolylene Diisocyanate (TDI), Hexamethylene Diisocyanate (HDI) and isophorone diisocyanate (IPDI) are preferably used, and 2 or more of them may be used in combination.
The adhesive composition of the present invention is required to have a softening point of 90 ℃ or higher, preferably 100 ℃ or higher, more preferably 110 ℃ or higher, and most preferably 120 ℃ or higher. When the softening point of the adhesive composition is less than 90 ℃, the heat resistance is lowered. The flexible flat cable containing the adhesive composition having reduced heat resistance may be as follows: in a high-temperature environment, the resin starts to flow and the metal peels off, causing dielectric breakdown. On the other hand, the upper limit of the softening point is preferably a temperature at which thermal decomposition of the copolyester resin does not occur, and is preferably less than 400 ℃.
In order to set the softening point of the adhesive composition of the present invention within the above range, the number average molecular weight of the adhesive composition is preferably 20000 to 100000, more preferably 30000 to 100000, and still more preferably 40000 to 100000. If the number average molecular weight of the adhesive composition is less than 20000, the softening point is lowered and the heat resistance is liable to be lowered. On the other hand, if the number average molecular weight of the adhesive composition exceeds 100000, the adhesiveness tends to decrease, which is not preferable.
In order to set the number average molecular weight of the adhesive composition of the present invention within the above range, the number average molecular weight of the copolyester of the present invention is preferably 5000 to 30000, and more preferably 10000 to 25000.
The adhesive composition of the present invention may contain a heat stabilizer, an antioxidant, a flame retardant, and the like as necessary.
Examples of the heat stabilizer include phosphoric acid, phosphoric acid esters, dibutyl hydroxytoluene tetrakis [ 3- (3 ', 5 ' -di-t-butyl-4 ' -hydroxyphenyl) propionic acid ] pentaerythritol ester, n-octadecyl 3- (3 ', 5 ' -di-t-butyl-4 ' -hydroxyphenyl) propionate, 3 ', 5,5 ' -hexa-t-butyl-a, a ' - (mesitylene-2, 4, 6-triyl) tri-p-cresol, 1, 3-tris (2-methyl-4-hydroxy-5-t-butylphenyl) butane, 1,3, 5-trimethyl-2, 4, 6-tris (3, 5-di-t-butyl-4-hydroxybenzyl) benzene, 3, 9-bis { 2- [ 3- (3-t-butyl-4-hydroxy-5-methylphenyl) propionyloxy ] -1, 1-dimethylethyl } -2, 4,8, 10-tetraoxaspiro [5, phosphorus-based or hindered phenol-based heat stabilizers such as 5] undecane, 1,3, 5-tris (4-tert-butyl-3-hydroxy-2, 6-dimethylbenzene) isophthalic acid, triethylene glycol-bis [ 3- (3-tert-butyl-5-methyl-4-hydroxyphenyl) propionate ], 1, 6-hexanediol-bis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], 2-thio-diethylene-bis [ 3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], octadecyl-3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionate ], diethyl [ [3, 5-bis (1, 1-dimethylethyl) -4-hydroxyphenyl ] methyl ] phosphate, and the like.
Examples of the antioxidant include hindered amine compounds, dioctylthiodipropionate, didodecylthiodipropionate (didodecylthiodipropionate), distearylthiodipropionate, dimyristylthiodipropionate, didecylthiodipropionate, didodecylthiodibutyrate, distearylthiodibutyrate, pentaerythritol-tetrakis (dodecylthiopropionate), pentaerythritol-tetrakis (dodecylthioacetate), pentaerythritol-tetrakis (dodecylthiobutyrate), pentaerythritol-tetrakis (octadecylthiopropionate), pentaerythritol-tetrakis (laurylthiopropionate), dilauryl-3, 3' -thiodipropionate, distearylthiodipropionate, ditridecyl 3, antioxidants such as 3' -thiodipropionate and tetrakis [ methylene-3- (dodecylthio) propionate ].
Examples of the flame retardant include halides such as decabromodiphenyl ether, bis (pentabromophenyl) ethane, tetrabromobisphenol, hexabromocyclododecane and hexabromobenzene, phosphorus compounds such as triphenyl phosphate, tricresyl phosphate, 1, 3-phenylene bis (diphenyl phosphate), ammonium polyphosphate, polyphosphoric acid amide and guanidine phosphate, halogen-containing phosphates such as tris (chloroethyl) phosphate and tris (dichloropropyl) phosphate, nitrogen-based flame retardants such as red phosphorus and triazine, melamine cyanurate and ethylene dimelamine, tin dioxide, antimony pentoxide and antimony trioxide.
In addition, conventionally known additives such as lubricants such as talc and silica, pigments such as titanium oxide and carbon black, fillers, antistatic agents, and foaming agents may be contained.
Next, a method for producing the adhesive composition of the present invention will be described.
In the production of a copolyester constituting an adhesive composition, a required raw material is charged into a reaction tank, an esterification reaction is carried out at a temperature of 180 ℃ or higher for 3 hours or longer, and then a polyalkylene glycol is added to carry out the esterification reaction by a known method. Then, for example, a polycondensation reaction is carried out at a temperature of 220 to 280 ℃ under a reduced pressure of 130Pa or less until a desired molecular weight is reached, whereby a copolyester can be obtained.
In the esterification reaction and polycondensation reaction, titanium compounds such as tetrabutyl titanate, metal acetates such as zinc acetate, magnesium acetate and zinc acetate, antimony trioxide and hydroxyAn organotin compound such as butyltin oxide or tin octylate is polymerized. The amount of the catalyst used in this case is preferably 0.1 to 20X 10 relative to 1 mole of the acid component－4And (3) mol.
After the above polycondensation reaction is completed, a predetermined amount of a polybasic acid component, an anhydride thereof, or the like is added to perform a reaction, whereby a terminal hydroxyl group can be modified into a carboxyl group, or a carboxyl group can be introduced into a molecule by a transesterification reaction, whereby an appropriate acid value can be imparted.
Then, the copolyester is dissolved in an appropriate organic solvent to prepare a solution having a solid content concentration of about 20 to 60 mass%, and a curing agent is added to the solution to prepare a solution of the adhesive composition. The adhesive composition can be obtained by removing the organic solvent from the solution of the adhesive composition.
Examples of the organic solvent include aromatic solvents such as toluene, xylene, solvent naphtha and aromatic oil solvents, ketone solvents such as methyl ethyl ketone, methyl isobutyl ketone and cyclohexanone, alcohol solvents such as methanol, ethanol, isopropanol and isobutanol, ester solvents such as ethyl acetate and n-butyl acetate, acetate solvents such as cellosolve acetate and methoxyacetate, and mixed solvents composed of 2 or more of these (for example, mixed solvents of toluene and methyl ethyl ketone). The organic solvent is preferably methyl ethyl ketone or ethyl acetate having a low boiling point from the viewpoints of handling properties and environment.
The laminate of the present invention has a layer composed of the adhesive composition.
As a method for producing a laminate having a layer composed of the adhesive composition (hereinafter, may be simply referred to as an adhesive layer) using the adhesive composition of the present invention, there is a method in which the adhesive composition is dissolved in an organic solvent to obtain a solution (hereinafter, may be simply referred to as an adhesive solution), and the solution is applied to a base film and dried. As the adhesive solution, a solution prepared by adding a curing agent to an organic solvent solution of a copolyester in the production of the above adhesive composition can be used. The concentration of the solid content in the binder solution is preferably 10 mass% or more, more preferably 20 mass% or more, and still more preferably 30 mass% or more.
A laminate in which adhesive layers are laminated can be obtained by applying an adhesive solution to a base material by a known application method and drying the adhesive solution. As the coater, for example, a bar coater, a comma coater, a die coater, a roll coater, a reverse roll coater, a gravure coater, a reverse gravure coater, a flow coater, or the like can be used. The coating method using these coaters can arbitrarily control the thickness of the adhesive layer. Alternatively, the coating may be applied to the substrate by a plurality of coating methods.
The flexible flat cable of the present invention includes the laminate, and can be produced, for example, by the following method.
That is, a laminate (insulating film) in which an adhesive layer is laminated on a base film is produced by using a base film having a thickness of about 20 to 50 μm and made of polyester such as polyethylene terephthalate, applying an adhesive solution to the base film so as to have a dry thickness of about 1 to 50 μm, and drying the adhesive solution at 80 to 150 ℃. A copper wire having a thickness of 20 to 100 [ mu ] m and a line width of 0.1 to 1mm is sandwiched between adhesive layers of 2 insulating films, and the copper wire is laminated by a heat sealer at a temperature of 150 to 180 ℃ and a line pressure of 20 to 40N/cm, thereby manufacturing a flexible flat cable.
The obtained laminated body and/or flexible flat cable can be heated and cured at 40-80 ℃ for about 12-96 h. In addition, a primer layer may be provided on the insulating film as needed.
Examples
The present invention will be described in detail with reference to examples.
1. Using raw materials
(1) Polyalkylene glycol
PTMG: polytetramethylene glycol (number average molecular weight 1000)
PEG: polyethylene glycol (number average molecular weight 1000)
TEG: triethylene glycol (molecular weight 150.17)
DEG: diethylene glycol (molecular weight 106.12)
(2) Curing agent
TDI: toluene-2, 4-diisocyanate/toluene-2, 6-diisocyanate (8/2) (containing 48% isocyanate)
TDI-A: tolylene diisocyanate adduct (containing 13% isocyanate)
IPDI: isophorone diisocyanate (containing 38% isocyanate)
IPDI-N: isophorone diisocyanate isocyanurate (containing 12% isocyanate)
HDI: hexamethylene-1, 6-diisocyanate (isocyanate 50%)
HDI-N: hexamethylene-1, 6-diisocyanate isocyanurate (containing 22% isocyanate)
(3) Organic solvent
Solvent 1: toluene/methyl ethyl ketone (8/2 (mass ratio)) mixed solvent
Solvent 2: methyl ethyl ketone
Solvent 3: ethyl acetate
2. Measurement method
(1) Composition of copolyester
Was carried out using an NMR measuring apparatus (JNM-LA 400 model manufactured by Nippon electronic Co., Ltd.)1The composition was determined from the peak intensities of the respective copolymerization components by H-NMR measurement. As a measurement solvent, deuterated trifluoroacetic acid was used.
(2) Number average molecular weight of copolyester and adhesive composition
The number average molecular weight was determined by using GPC analyzers (liquid delivery cell LC-10 ADvp type manufactured by Shimadzu corporation and ultraviolet-visible spectrophotometer SPD-6 AV type, detection wavelength 254nm, solvent tetrahydrofuran, and polystyrene conversion). The adhesive composition is "insoluble" in that it is not soluble in tetrahydrofuran and the number average molecular weight cannot be measured.
(3) Glass transition Point (Tg) of copolyester
The glass transition point (extrapolated glass transition onset temperature) was determined in accordance with JIS-K7121 using an input offset differential scanning calorimetry (Diamond DSC, Perkin Elmer Co., Ltd.).
(4) Softening point
The laminates obtained in examples and comparative examples were heat-treated at 50 ℃ for 96 hours, and then the softening point was measured according to JIS-K7196 using a thermomechanical analyzer (TMA manufactured by TAInstructions Co., Ltd.) to evaluate the heat resistance.
(5) Adhesion Property
(adhesiveness 1)
The laminates obtained in examples and comparative examples were heat-treated at 50 ℃ for 96 hours, then rolled copper foil was superimposed on the adhesive composition layer of the laminate, and laminated under conditions of an upper roll 170 ℃, a line pressure of 40N/cm, and a speed of 1 m/min to produce a laminate sheet 1.
From the obtained laminate sheet 1, a 15mm wide sample was prepared, and a T-peel test was performed at 20 ℃ to measure the peel strength and evaluate the adhesiveness 1.
(adhesiveness 2)
A copper foil was laminated on the adhesive composition layer of the laminate obtained in examples and comparative examples, and the laminate was laminated at a top roll temperature of 170 ℃, a line pressure of 40N/cm, and a speed of 1 m/min, and then heat-treated at 50 ℃ for 96 hours to prepare a laminate sheet 2.
From the obtained laminate sheet 2, a 15mm wide sample was prepared, and a T-peel test was performed at 20 ℃ to measure the peel strength and evaluate the adhesiveness 2.
In any of the evaluations of adhesiveness 1 and adhesiveness 2, when the peel strength was 13N/15mm or more, it was judged that there was no problem in practical use and it was judged as a pass.
(6) Moisture and heat resistance
The laminate sheet 2 produced by the method described in the adhesiveness 2 of (5) above was subjected to a moist heat treatment by keeping it at a temperature of 85 ℃ and a relative humidity of 85% for 1000 hours in a constant temperature and humidity tank (model LH-30-13M manufactured by Nakatsu scientific machinist).
A15 mm wide sample was prepared from the laminate sheet 2 after the wet heat treatment, and a T-peel test was conducted at 20 ℃ to measure the peel strength and evaluate the wet heat resistance. When the peel strength was 6N/15mm or more, it was judged that there was no problem in practical use and it was judged to be acceptable.
(7) Heat resistance
A sample having a width of 15mm was prepared from the laminate 2 prepared by the method described in the adhesiveness 2 of (5) above, and a T-peel test was performed at 80 ℃ to measure the peel strength and evaluate the heat resistance. When the peel strength was 3N/15mm or more, it was judged that there was no problem in practical use and it was judged to be acceptable.
Example 1
The raw materials were charged into an esterification reaction tank so that the acid component was 50 mol% of terephthalic acid and 50 mol% of isophthalic acid, and the glycol components were 44 mol% of ethylene glycol, 50 mol% of neopentyl glycol, 5 mol% of polytetramethylene glycol (PTMG) having a number average molecular weight of 1000, and 1 mol% of diethylene glycol (DEG), and the esterification reaction was carried out at 250 ℃ for 5 hours under a pressure of 0.25MPa while stirring at a rotation speed of 100rpm by an anchor blade stirrer to prepare an esterified product. Thereafter, the resulting polymer was transferred to a polycondensation pot, and a polymerization catalyst was charged into the pot, and the pressure was gradually reduced to 1.3hPa for 60 minutes, and a polycondensation reaction was carried out at 250 ℃ until a predetermined molecular weight was reached to obtain a copolyester A. The number average molecular weight of the resulting copolyester A was 20000, the hydroxyl value was 5mgKOH/g, and the glass transition point was 15 ℃.
An adhesive composition solution was prepared by dissolving 100 parts by mass of the copolyester a in a mixed solvent (solvent 1) of toluene/methyl ethyl ketone (8/2 (mass ratio)) so that the solid content concentration was 30 mass%, and adding 0.6 part by mass of the curing agent (TDI).
The solution was applied to a rolled copper foil (thickness: 30 μm) by a bar coater, and heat treatment was carried out at 120 ℃ for 1 minute to obtain a laminate in which an adhesive composition layer having a dry thickness of 20 μm was laminated on the copper foil.
Examples 2 to 3
Copolyesters B and C were obtained in the same manner as in example 1, except that the polymerization time in the polycondensation reaction using the esterified compound was changed and adjusted to the number average molecular weight shown in table 1.
An adhesive composition solution was obtained in the same manner as in example 1, except that the copolyester B, C thus obtained was used and the amount of the curing agent (TDI) added was changed to the amount shown in table 1. Then, a laminate was obtained in the same manner as in example 1.
Examples 4 to 16 and comparative examples 4 to 7
Copolyesters D to P, R to U were obtained in the same manner as in example 1, except that the composition of the copolyester was changed as shown in tables 1,2, and 4, and the polymerization time in the polycondensation reaction using the esterified product was changed so that the number average molecular weight reached the value shown in tables 1,2, and 4.
A solution of an adhesive composition was obtained in the same manner as in example 1, except that the obtained copolyesters D to P, R to U were used. Then, a laminate was obtained in the same manner as in example 1.
Example 17
An adhesive composition solution was obtained in the same manner as in example 1, except that the copolyester a (80 parts by mass) obtained in example 1 and the copolyester R (20 parts by mass) obtained in comparative example 4 were used as the copolyesters. Then, a laminate was obtained in the same manner as in example 1.
Examples 18 to 19
An adhesive composition solution was obtained in the same manner as in example 1, except that the kind of the solvent used in obtaining the adhesive composition solution was changed to the kind shown in table 3. Then, a laminate was obtained in the same manner as in example 1.
Examples 20 to 23 and comparative examples 1 to 2
An adhesive composition solution was obtained in the same manner as in example 1, except that the amount of the curing agent added to the copolyester a was changed to the amounts shown in tables 3 and 4. Then, a laminate was obtained in the same manner as in example 1.
Example 24 and comparative example 3
An adhesive composition solution was obtained in the same manner as in example 1, except that the addition amount of the curing agent to the copolyester B was changed to the addition amounts shown in tables 3 and 4. Then, a laminate was obtained in the same manner as in example 1.
Example 25
A copolyester Q was obtained in the same manner as in example 1, except that the composition of the copolyester was changed as shown in table 3, and the polymerization time in the polycondensation reaction using an esterified compound was changed so that the number average molecular weight became the value shown in table 3.
An adhesive composition solution was obtained in the same manner as in example 1, except that the amount of the curing agent added to the copolyester Q was changed to the amount shown in table 3. Then, a laminate was obtained in the same manner as in example 1.
Examples 26 to 28
An adhesive composition solution was obtained in the same manner as in example 1, except that the kind and the addition amount of the curing agent in the case of obtaining the adhesive composition solution were changed to those shown in table 3. Then, a laminate was obtained in the same manner as in example 1.
Examples 29 to 32
An adhesive composition solution was obtained in the same manner as in example 1, except that 2 kinds of curing agents were used when obtaining the adhesive composition solution, and the kind and the addition amount were changed to those shown in table 4. Then, a laminate was obtained in the same manner as in example 1.
The characteristics of the copolyester, the adhesive composition and the laminate obtained in examples and comparative examples are shown in tables 1 to 4.
[ Table 1]
[ Table 2]
[ Table 3]
[ Table 4]
The adhesive compositions obtained in examples 1 to 32 satisfy the constitution specified in the present invention, and therefore, are excellent in adhesion to metals and also excellent in heat resistance and moist heat resistance. Therefore, the laminates obtained using these adhesive compositions were excellent in the evaluation results of their performances.
The adhesive composition of comparative example 1 had a softening point as low as 55 ℃ and poor heat resistance because the content of the curing agent was as low as 0.1 part by mass.
The adhesive composition of comparative example 2 had poor adhesiveness because the content of the curing agent was as high as 15.7 parts by mass.
The adhesive composition of comparative example 3 had a low number average molecular weight of 16000 and a low softening point of 85 ℃.
The adhesive composition of comparative example 4 has poor adhesion and moist heat resistance because the content of polyalkylene glycol having a repeating unit of 2 to 4 carbon atoms in the glycol component of the copolyester is as low as 0.5 mol%, and the glass transition point of the copolyester is as high as 65 ℃.
The adhesive composition of comparative example 5 has a softening point as low as 80 ℃ and poor heat resistance because the content of the polyalkylene glycol having a repeating unit of 2 to 4 carbon atoms in the glycol component of the copolyester is as high as 25 mol%.
The adhesive composition of comparative example 6 was poor in both adhesiveness because the content of neopentyl glycol as a diol having a side chain in the copolyester was as low as 20 mol% in the diol component, and the content of isophthalic acid in the copolyester was as low as 20 mol% in the acid component in the adhesive composition of comparative example 7. In addition, the solubility of any adhesive composition in an organic solvent is poor.
Claims (3)
1. An adhesive composition characterized by comprising 100 parts by mass of a copolyester and 0.2 to 15 parts by mass of a curing agent,
the content of isophthalic acid in the acid component of the copolyester is 30 mol% or more,
the content of the diol having a side chain in the diol component of the copolyester is 30 mol% or more, the content of the polyalkylene glycol having 2 to 4 carbon atoms in the repeating unit, 2 or more species and at least 1 species having a number average molecular weight of 200 or more is 1 to 20 mol%,
the softening point of the adhesive composition is 90 ℃ or higher.
2. A laminate comprising a layer composed of the adhesive composition according to claim 1.
3. A flexible flat cable comprising the laminate of claim 2.
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| CN202111368795.8A CN114045145B (en) | 2016-04-15 | 2017-04-13 | Adhesive composition |
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| PCT/JP2017/015085 WO2017179645A1 (en) | 2016-04-15 | 2017-04-13 | Adhesive composition |
| CN202111368795.8A CN114045145B (en) | 2016-04-15 | 2017-04-13 | Adhesive composition |
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| KR (1) | KR102320463B1 (en) |
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| CN113881361B (en) * | 2021-10-29 | 2023-07-04 | 苏州赛伍应用技术股份有限公司 | Hot-pressing insulating film for FFC and FFC containing same |
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| WO2015083626A1 (en) * | 2013-12-02 | 2015-06-11 | ユニチカ株式会社 | Polyester resin composition, and adhesive containing same |
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| DE4121703A1 (en) * | 1991-07-01 | 1993-01-07 | Huels Chemische Werke Ag | FILM-FORMING, RADIATION-HARDENABLE AND HUMIDITY-HARDENING LAMINATING ADHESIVE, METHOD FOR LAMINATING TEXTILE LAYERS WITH THIS LAMINATING ADHESIVE, AND TEXTILE MATERIAL FROM TEXTILE LAYERS AND FOILS OF THE CASE |
| JPH07268308A (en) * | 1994-03-30 | 1995-10-17 | Toyobo Co Ltd | Polyester-based adhesive |
| JP2000063643A (en) * | 1998-08-20 | 2000-02-29 | Mitsubishi Rayon Co Ltd | Metal laminating polyester resin composition, metal laminating polyester film using same and laminated metallic material |
| JP4409023B2 (en) | 2000-01-17 | 2010-02-03 | ユニチカ株式会社 | Copolymerized polyester resin for adhesive and adhesive using the same |
| JP2004250484A (en) * | 2003-02-18 | 2004-09-09 | Nippon Ester Co Ltd | Polyester resin for adhesive, adhesive, and laminate |
| JP5124903B2 (en) * | 2005-02-04 | 2013-01-23 | 東洋紡株式会社 | Polyester resin, aqueous dispersion and adhesive using the same |
| JP5643144B2 (en) * | 2011-03-31 | 2014-12-17 | ユニチカ株式会社 | adhesive |
| JP5187468B1 (en) * | 2011-09-30 | 2013-04-24 | 東洋紡株式会社 | Adhesive composition, laminate and polyester polyol |
| WO2014103994A1 (en) * | 2012-12-26 | 2014-07-03 | Dic株式会社 | Polyester resin composition, adhesive, and film |
| CN106661312B (en) * | 2014-08-15 | 2019-07-05 | 尤尼吉可株式会社 | Polyester resin, coating fluid and laminated body |
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| CN114045145B (en) | 2024-01-23 |
| KR20180132609A (en) | 2018-12-12 |
| KR102320463B1 (en) | 2021-11-02 |
| JPWO2017179645A1 (en) | 2019-02-21 |
| CN108779378A (en) | 2018-11-09 |
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| JP6955768B2 (en) | 2021-10-27 |
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