WO2018030050A1 - ポリオレフィン系接着剤組成物 - Google Patents
ポリオレフィン系接着剤組成物 Download PDFInfo
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- WO2018030050A1 WO2018030050A1 PCT/JP2017/025066 JP2017025066W WO2018030050A1 WO 2018030050 A1 WO2018030050 A1 WO 2018030050A1 JP 2017025066 W JP2017025066 W JP 2017025066W WO 2018030050 A1 WO2018030050 A1 WO 2018030050A1
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- Prior art keywords
- epoxy resin
- parts
- mass
- type epoxy
- acid
- Prior art date
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- 229910052700 potassium Inorganic materials 0.000 description 2
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- 238000002360 preparation method Methods 0.000 description 2
- BBEAQIROQSPTKN-UHFFFAOYSA-N pyrene Chemical compound C1=CC=C2C=CC3=CC=CC4=CC=C1C2=C43 BBEAQIROQSPTKN-UHFFFAOYSA-N 0.000 description 2
- 239000011734 sodium Substances 0.000 description 2
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- RYYKJJJTJZKILX-UHFFFAOYSA-M sodium octadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCC([O-])=O RYYKJJJTJZKILX-UHFFFAOYSA-M 0.000 description 2
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- GGXKEBACDBNFAF-UHFFFAOYSA-M sodium;hexadecanoate Chemical compound [Na+].CCCCCCCCCCCCCCCC([O-])=O GGXKEBACDBNFAF-UHFFFAOYSA-M 0.000 description 2
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- UUQQGGWZVKUCBD-UHFFFAOYSA-N [4-(hydroxymethyl)-2-phenyl-1h-imidazol-5-yl]methanol Chemical compound N1C(CO)=C(CO)N=C1C1=CC=CC=C1 UUQQGGWZVKUCBD-UHFFFAOYSA-N 0.000 description 1
- YXIKKCKBKTYHMU-UHFFFAOYSA-L [Ca++].[O-]C(=O)c1ccc2ccccc2c1C([O-])=O Chemical compound [Ca++].[O-]C(=O)c1ccc2ccccc2c1C([O-])=O YXIKKCKBKTYHMU-UHFFFAOYSA-L 0.000 description 1
- CQQXCSFSYHAZOO-UHFFFAOYSA-L [acetyloxy(dioctyl)stannyl] acetate Chemical compound CCCCCCCC[Sn](OC(C)=O)(OC(C)=O)CCCCCCCC CQQXCSFSYHAZOO-UHFFFAOYSA-L 0.000 description 1
- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 1
- XQBCVRSTVUHIGH-UHFFFAOYSA-L [dodecanoyloxy(dioctyl)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCCCCCC)(CCCCCCCC)OC(=O)CCCCCCCCCCC XQBCVRSTVUHIGH-UHFFFAOYSA-L 0.000 description 1
- KXKVLQRXCPHEJC-UHFFFAOYSA-N acetic acid trimethyl ester Natural products COC(C)=O KXKVLQRXCPHEJC-UHFFFAOYSA-N 0.000 description 1
- HDYRYUINDGQKMC-UHFFFAOYSA-M acetyloxyaluminum;dihydrate Chemical compound O.O.CC(=O)O[Al] HDYRYUINDGQKMC-UHFFFAOYSA-M 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 150000007933 aliphatic carboxylic acids Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 229910045601 alloy Inorganic materials 0.000 description 1
- 239000000956 alloy Substances 0.000 description 1
- BJEPYKJPYRNKOW-UHFFFAOYSA-N alpha-hydroxysuccinic acid Natural products OC(=O)C(O)CC(O)=O BJEPYKJPYRNKOW-UHFFFAOYSA-N 0.000 description 1
- 229940009827 aluminum acetate Drugs 0.000 description 1
- 229960004050 aminobenzoic acid Drugs 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 1
- 239000003125 aqueous solvent Substances 0.000 description 1
- 229940116226 behenic acid Drugs 0.000 description 1
- KKEYFWRCBNTPAC-UHFFFAOYSA-N benzene-dicarboxylic acid Natural products OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 1
- 125000003785 benzimidazolyl group Chemical class N1=C(NC2=C1C=CC=C2)* 0.000 description 1
- 235000010233 benzoic acid Nutrition 0.000 description 1
- QRUDEWIWKLJBPS-UHFFFAOYSA-N benzotriazole Chemical compound C1=CC=C2N[N][N]C2=C1 QRUDEWIWKLJBPS-UHFFFAOYSA-N 0.000 description 1
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- 235000019400 benzoyl peroxide Nutrition 0.000 description 1
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 description 1
- QZUNEQNSDLPXCA-UHFFFAOYSA-N butan-2-one;pentan-2-one Chemical compound CCC(C)=O.CCCC(C)=O QZUNEQNSDLPXCA-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 1
- 229940078456 calcium stearate Drugs 0.000 description 1
- FYPVXEILSNEKOO-UHFFFAOYSA-L calcium;butanoate Chemical compound [Ca+2].CCCC([O-])=O.CCCC([O-])=O FYPVXEILSNEKOO-UHFFFAOYSA-L 0.000 description 1
- NDWWLJQHOLSEHX-UHFFFAOYSA-L calcium;octanoate Chemical compound [Ca+2].CCCCCCCC([O-])=O.CCCCCCCC([O-])=O NDWWLJQHOLSEHX-UHFFFAOYSA-L 0.000 description 1
- SHZIWNPUGXLXDT-UHFFFAOYSA-N caproic acid ethyl ester Natural products CCCCCC(=O)OCC SHZIWNPUGXLXDT-UHFFFAOYSA-N 0.000 description 1
- 239000004202 carbamide Substances 0.000 description 1
- 150000004649 carbonic acid derivatives Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000012295 chemical reaction liquid Substances 0.000 description 1
- ZCDOYSPFYFSLEW-UHFFFAOYSA-N chromate(2-) Chemical compound [O-][Cr]([O-])(=O)=O ZCDOYSPFYFSLEW-UHFFFAOYSA-N 0.000 description 1
- HNEGQIOMVPPMNR-IHWYPQMZSA-N citraconic acid Chemical compound OC(=O)C(/C)=C\C(O)=O HNEGQIOMVPPMNR-IHWYPQMZSA-N 0.000 description 1
- 229940018557 citraconic acid Drugs 0.000 description 1
- 235000015165 citric acid Nutrition 0.000 description 1
- HHZAIOOQYMFSFC-UHFFFAOYSA-L cobalt(2+);3-oxobutanoate Chemical compound [Co+2].CC(=O)CC([O-])=O.CC(=O)CC([O-])=O HHZAIOOQYMFSFC-UHFFFAOYSA-L 0.000 description 1
- 239000000470 constituent Substances 0.000 description 1
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- 229940120693 copper naphthenate Drugs 0.000 description 1
- SEVNKWFHTNVOLD-UHFFFAOYSA-L copper;3-(4-ethylcyclohexyl)propanoate;3-(3-ethylcyclopentyl)propanoate Chemical compound [Cu+2].CCC1CCC(CCC([O-])=O)C1.CCC1CCC(CCC([O-])=O)CC1 SEVNKWFHTNVOLD-UHFFFAOYSA-L 0.000 description 1
- 230000007797 corrosion Effects 0.000 description 1
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- AYOHIQLKSOJJQH-UHFFFAOYSA-N dibutyltin Chemical compound CCCC[Sn]CCCC AYOHIQLKSOJJQH-UHFFFAOYSA-N 0.000 description 1
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- 239000000539 dimer Substances 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
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- BXKDSDJJOVIHMX-UHFFFAOYSA-N edrophonium chloride Chemical compound [Cl-].CC[N+](C)(C)C1=CC=CC(O)=C1 BXKDSDJJOVIHMX-UHFFFAOYSA-N 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 150000002118 epoxides Chemical class 0.000 description 1
- DPUOLQHDNGRHBS-KTKRTIGZSA-N erucic acid Chemical compound CCCCCCCC\C=C/CCCCCCCCCCCC(O)=O DPUOLQHDNGRHBS-KTKRTIGZSA-N 0.000 description 1
- 150000002168 ethanoic acid esters Chemical class 0.000 description 1
- IIEWJVIFRVWJOD-UHFFFAOYSA-N ethyl cyclohexane Natural products CCC1CCCCC1 IIEWJVIFRVWJOD-UHFFFAOYSA-N 0.000 description 1
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000003063 flame retardant Substances 0.000 description 1
- GVEPBJHOBDJJJI-UHFFFAOYSA-N fluoranthrene Natural products C1=CC(C2=CC=CC=C22)=C3C2=CC=CC3=C1 GVEPBJHOBDJJJI-UHFFFAOYSA-N 0.000 description 1
- 239000007789 gas Substances 0.000 description 1
- VANNPISTIUFMLH-UHFFFAOYSA-N glutaric anhydride Chemical compound O=C1CCCC(=O)O1 VANNPISTIUFMLH-UHFFFAOYSA-N 0.000 description 1
- 238000010559 graft polymerization reaction Methods 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- 150000002429 hydrazines Chemical class 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 125000004435 hydrogen atom Chemical class [H]* 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 150000002460 imidazoles Chemical class 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 230000000977 initiatory effect Effects 0.000 description 1
- 229910052742 iron Inorganic materials 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 238000003475 lamination Methods 0.000 description 1
- 239000010410 layer Substances 0.000 description 1
- 229910052745 lead Inorganic materials 0.000 description 1
- XIXADJRWDQXREU-UHFFFAOYSA-M lithium acetate Chemical compound [Li+].CC([O-])=O XIXADJRWDQXREU-UHFFFAOYSA-M 0.000 description 1
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- 230000007774 longterm Effects 0.000 description 1
- UEGPKNKPLBYCNK-UHFFFAOYSA-L magnesium acetate Chemical compound [Mg+2].CC([O-])=O.CC([O-])=O UEGPKNKPLBYCNK-UHFFFAOYSA-L 0.000 description 1
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- 229940069446 magnesium acetate Drugs 0.000 description 1
- WWRYOAYBSQIWNU-UHFFFAOYSA-L magnesium;decanoate Chemical compound [Mg+2].CCCCCCCCCC([O-])=O.CCCCCCCCCC([O-])=O WWRYOAYBSQIWNU-UHFFFAOYSA-L 0.000 description 1
- OFUAIAKLWWIPTC-UHFFFAOYSA-L magnesium;naphthalene-2-carboxylate Chemical compound [Mg+2].C1=CC=CC2=CC(C(=O)[O-])=CC=C21.C1=CC=CC2=CC(C(=O)[O-])=CC=C21 OFUAIAKLWWIPTC-UHFFFAOYSA-L 0.000 description 1
- LUYZTDPLLWFWQU-UHFFFAOYSA-L magnesium;terephthalate Chemical compound [Mg+2].[O-]C(=O)C1=CC=C(C([O-])=O)C=C1 LUYZTDPLLWFWQU-UHFFFAOYSA-L 0.000 description 1
- 239000002075 main ingredient Substances 0.000 description 1
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 1
- 239000011976 maleic acid Substances 0.000 description 1
- 239000001630 malic acid Substances 0.000 description 1
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- 229910052748 manganese Inorganic materials 0.000 description 1
- 150000002739 metals Chemical class 0.000 description 1
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- VYKXQOYUCMREIS-UHFFFAOYSA-N methylhexahydrophthalic anhydride Chemical compound C1CCCC2C(=O)OC(=O)C21C VYKXQOYUCMREIS-UHFFFAOYSA-N 0.000 description 1
- 239000011259 mixed solution Substances 0.000 description 1
- UICBCXONCUFSOI-UHFFFAOYSA-N n'-phenylacetohydrazide Chemical compound CC(=O)NNC1=CC=CC=C1 UICBCXONCUFSOI-UHFFFAOYSA-N 0.000 description 1
- GYVGXEWAOAAJEU-UHFFFAOYSA-N n,n,4-trimethylaniline Chemical compound CN(C)C1=CC=C(C)C=C1 GYVGXEWAOAAJEU-UHFFFAOYSA-N 0.000 description 1
- GEMHFKXPOCTAIP-UHFFFAOYSA-N n,n-dimethyl-n'-phenylcarbamimidoyl chloride Chemical compound CN(C)C(Cl)=NC1=CC=CC=C1 GEMHFKXPOCTAIP-UHFFFAOYSA-N 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- LPXPSTWBTULMJE-UHFFFAOYSA-N n-phenylbutan-1-imine Chemical compound CCCC=NC1=CC=CC=C1 LPXPSTWBTULMJE-UHFFFAOYSA-N 0.000 description 1
- 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 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 1
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 235000021313 oleic acid Nutrition 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- IGALFTFNPPBUDN-UHFFFAOYSA-N phenyl-[2,3,4,5-tetrakis(oxiran-2-ylmethyl)phenyl]methanediamine Chemical compound C=1C(CC2OC2)=C(CC2OC2)C(CC2OC2)=C(CC2OC2)C=1C(N)(N)C1=CC=CC=C1 IGALFTFNPPBUDN-UHFFFAOYSA-N 0.000 description 1
- LFSXCDWNBUNEEM-UHFFFAOYSA-N phthalazine Chemical class C1=NN=CC2=CC=CC=C21 LFSXCDWNBUNEEM-UHFFFAOYSA-N 0.000 description 1
- 150000004885 piperazines Chemical class 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
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- 229920005990 polystyrene resin Polymers 0.000 description 1
- RWMKSKOZLCXHOK-UHFFFAOYSA-M potassium;butanoate Chemical compound [K+].CCCC([O-])=O RWMKSKOZLCXHOK-UHFFFAOYSA-M 0.000 description 1
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- YLLIGHVCTUPGEH-UHFFFAOYSA-M potassium;ethanol;hydroxide Chemical compound [OH-].[K+].CCO YLLIGHVCTUPGEH-UHFFFAOYSA-M 0.000 description 1
- 230000008569 process Effects 0.000 description 1
- 230000001737 promoting effect Effects 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
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- 125000001042 pteridinyl group Chemical class N1=C(N=CC2=NC=CN=C12)* 0.000 description 1
- 125000000561 purinyl group Chemical class N1=C(N=C2N=CNC2=C1)* 0.000 description 1
- 150000003216 pyrazines Chemical class 0.000 description 1
- 150000003217 pyrazoles Chemical class 0.000 description 1
- 150000004892 pyridazines Chemical class 0.000 description 1
- 150000003230 pyrimidines Chemical class 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 125000002294 quinazolinyl group Chemical class N1=C(N=CC2=CC=CC=C12)* 0.000 description 1
- 230000009257 reactivity Effects 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 229960004249 sodium acetate Drugs 0.000 description 1
- WXMKPNITSTVMEF-UHFFFAOYSA-M sodium benzoate Chemical compound [Na+].[O-]C(=O)C1=CC=CC=C1 WXMKPNITSTVMEF-UHFFFAOYSA-M 0.000 description 1
- 239000004299 sodium benzoate Substances 0.000 description 1
- 235000010234 sodium benzoate Nutrition 0.000 description 1
- BYKRNSHANADUFY-UHFFFAOYSA-M sodium octanoate Chemical compound [Na+].CCCCCCCC([O-])=O BYKRNSHANADUFY-UHFFFAOYSA-M 0.000 description 1
- CVYDEWKUJFCYJO-UHFFFAOYSA-M sodium;docosanoate Chemical compound [Na+].CCCCCCCCCCCCCCCCCCCCCC([O-])=O CVYDEWKUJFCYJO-UHFFFAOYSA-M 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 239000008117 stearic acid Substances 0.000 description 1
- RINCXYDBBGOEEQ-UHFFFAOYSA-N succinic anhydride Chemical group O=C1CCC(=O)O1 RINCXYDBBGOEEQ-UHFFFAOYSA-N 0.000 description 1
- 239000011975 tartaric acid Substances 0.000 description 1
- 235000002906 tartaric acid Nutrition 0.000 description 1
- ROEHNQZQCCPZCH-UHFFFAOYSA-N tert-butyl 2-tert-butylperoxycarbonylbenzoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1C(=O)OC(C)(C)C ROEHNQZQCCPZCH-UHFFFAOYSA-N 0.000 description 1
- GJBRNHKUVLOCEB-UHFFFAOYSA-N tert-butyl benzenecarboperoxoate Chemical compound CC(C)(C)OOC(=O)C1=CC=CC=C1 GJBRNHKUVLOCEB-UHFFFAOYSA-N 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- TUNFSRHWOTWDNC-HKGQFRNVSA-N tetradecanoic acid Chemical compound CCCCCCCCCCCCC[14C](O)=O TUNFSRHWOTWDNC-HKGQFRNVSA-N 0.000 description 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 1
- 229920005992 thermoplastic resin Polymers 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 230000008719 thickening Effects 0.000 description 1
- 229910052718 tin Inorganic materials 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 238000004448 titration Methods 0.000 description 1
- 231100000331 toxic Toxicity 0.000 description 1
- 230000002588 toxic effect Effects 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- PWBHRVGYSMBMIO-UHFFFAOYSA-M tributylstannanylium;acetate Chemical compound CCCC[Sn](CCCC)(CCCC)OC(C)=O PWBHRVGYSMBMIO-UHFFFAOYSA-M 0.000 description 1
- HFFZSMFXOBHQLV-UHFFFAOYSA-M tributylstannyl dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)CCCC HFFZSMFXOBHQLV-UHFFFAOYSA-M 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical group OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
- 229940057977 zinc stearate Drugs 0.000 description 1
- WDHVIZKSFZNHJB-UHFFFAOYSA-L zinc;butanoate Chemical compound [Zn+2].CCCC([O-])=O.CCCC([O-])=O WDHVIZKSFZNHJB-UHFFFAOYSA-L 0.000 description 1
- JDLYKQWJXAQNNS-UHFFFAOYSA-L zinc;dibenzoate Chemical compound [Zn+2].[O-]C(=O)C1=CC=CC=C1.[O-]C(=O)C1=CC=CC=C1 JDLYKQWJXAQNNS-UHFFFAOYSA-L 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
- C09J123/30—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment by oxidation
-
- 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
- B32B15/085—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 polyolefins
-
- 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
-
- 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
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
-
- 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
- C09J123/00—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers
- C09J123/26—Adhesives based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Adhesives based on derivatives of such polymers modified by chemical after-treatment
-
- 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
- C09J163/00—Adhesives based on epoxy resins; Adhesives based on derivatives of epoxy resins
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- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M10/00—Secondary cells; Manufacture thereof
- H01M10/05—Accumulators with non-aqueous electrolyte
- H01M10/052—Li-accumulators
- H01M10/0525—Rocking-chair batteries, i.e. batteries with lithium insertion or intercalation in both electrodes; Lithium-ion batteries
-
- H—ELECTRICITY
- H01—ELECTRIC ELEMENTS
- H01M—PROCESSES OR MEANS, e.g. BATTERIES, FOR THE DIRECT CONVERSION OF CHEMICAL ENERGY INTO ELECTRICAL ENERGY
- H01M50/00—Constructional details or processes of manufacture of the non-active parts of electrochemical cells other than fuel cells, e.g. hybrid cells
- H01M50/10—Primary casings; Jackets or wrappings
- H01M50/116—Primary casings; Jackets or wrappings characterised by the material
- H01M50/124—Primary casings; Jackets or wrappings characterised by the material having a layered structure
-
- 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
- B32B2457/00—Electrical equipment
- B32B2457/18—Fuel cells
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
- Y02E60/00—Enabling technologies; Technologies with a potential or indirect contribution to GHG emissions mitigation
- Y02E60/10—Energy storage using batteries
Definitions
- the present invention relates to an adhesive composition for bonding a polyolefin resin substrate and a metal substrate. More specifically, the present invention relates to an adhesive composition containing a crystalline acid-modified polyolefin, an epoxy resin and an organic solvent, and further containing any one of an acid anhydride monomer and a heterocyclic compound having two or more nitrogen atoms.
- a solvent dispersion-type modified polyolefin resin is mixed with a base adhesive in which a thermosetting resin such as a phenol resin, a melamine resin, or an epoxy resin or a thermoplastic resin is dissolved in an organic solvent.
- a thermosetting resin such as a phenol resin, a melamine resin, or an epoxy resin or a thermoplastic resin is dissolved in an organic solvent.
- the pot life after blending with the acid-modified polyolefin solution may be poor, and even if the pot life is not so problematic, the adhesion and chemical resistance with the metal base material are not sufficient. . That is, there was nothing that satisfied pot life, adhesiveness and chemical resistance.
- a polypropylene (hereinafter also referred to as PP) substrate is used, there is no adhesive that can be bonded and aged (cured) at a low temperature of 80 ° C. or less, which is less affected by heat shrinkage.
- the pot life property refers to the stability of the solution immediately after the compounding or after a certain period of time when a crosslinking agent or a curing agent is compounded with the acid-modified polyolefin.
- a laminate of a polyolefin resin base material and a metal base material a laminate in which a polypropylene film and an aluminum foil are bonded together with an adhesive has recently been actively used as an exterior body for a lithium ion battery.
- the laminate is required to have chemical resistance (hereinafter also referred to as “electrolytic solution resistance”) to the electrolytic solution as the contents.
- the electrolyte solution of a lithium ion battery is obtained, for example, by dissolving lithium salts such as LiPF 6 and LiBF 4 as an electrolyte in a non-aqueous solvent such as carbonates.
- a lithium salt used as an electrolyte is hydrolyzed by moisture to generate hydrogen fluoride. For this reason, when hydrogen fluoride is generated, the metal members constituting the battery may corrode or the adhesiveness between layers of the laminated film type packaging material used as the exterior body may be deteriorated. is there.
- the present invention has been made in view of the above-described conventional problems, and as a result of intensive studies on the adhesive between a polyolefin resin substrate and a metal substrate, the present inventors have found that a crystalline acid-modified polyolefin (hereinafter, Simply referred to as an acid-modified polyolefin), an adhesive composition containing an epoxy resin and an organic solvent, and further containing either an acid anhydride monomer or a heterocyclic compound having two or more nitrogen atoms. And bonding at 80 ° C. or lower, adhesiveness and chemical resistance in aging, particularly resistance to electrolytic solution mixed with moisture, and the present invention has been completed.
- an acid-modified polyolefin an adhesive composition containing an epoxy resin and an organic solvent, and further containing either an acid anhydride monomer or a heterocyclic compound having two or more nitrogen atoms.
- the present invention has good pot life properties after blending a crystalline acid-modified polyolefin, a curing agent and a curing accelerator, and both a polyolefin resin substrate and a metal substrate in low temperature bonding and aging.
- An object of the present invention is to provide an adhesive composition having good adhesion and chemical resistance.
- the glycidylamine type epoxy resin (B1) is preferably an epoxy resin having two or more glycidyl groups in one molecule.
- the glycidylamine type epoxy resin (B1) is preferably a compound represented by the general formula (1).
- R is an aryl group which may have a substituent
- X1 and X2 are each independently an alkylene group having 1 to 5 carbon atoms which may have a substituent
- m is 1 or 2
- n is 1 or 2.
- the glycidyl ether type epoxy resin (B2) is preferably an epoxy resin having two or more glycidyl groups in one molecule and containing no nitrogen atom.
- the acid anhydride monomer (C) is preferably a compound having one or more acid anhydride rings in one molecule and an acid value of 100 mgKOH / g or more.
- the heterocyclic compound (D) having two or more nitrogen atoms is preferably a 5-membered aromatic heterocyclic compound having two or more nitrogen atoms.
- glycidylamine type epoxy resin (B1) 0.01 to 20 parts by mass of glycidylamine type epoxy resin (B1), 1 to 50 parts by mass of glycidyl ether type epoxy resin (B2), and 100% by mass of crystalline acid-modified polyolefin (A) It is preferable to contain 1 to 50 parts by mass of the monomer (C), 0.01 to 5 parts by mass of the heterocyclic compound (D) having two or more nitrogen atoms, and 80 to 1000 parts by mass of the organic solvent (E).
- the organic solvent (E) is a mixed liquid of the solvent (E1) and the solvent (E2), and the solvent (E1) is composed of an aromatic hydrocarbon, an aliphatic hydrocarbon, an alicyclic hydrocarbon, and a halogenated hydrocarbon.
- a packaging material for a lithium ion battery comprising the laminate as a constituent member.
- the adhesive composition according to the present invention contains a crystalline acid-modified polyolefin, two types of epoxy resins, and an organic solvent, and further includes any one of an acid anhydride monomer and a heterocyclic compound having two or more nitrogen atoms. Even if it contains and preserve
- the crystalline acid-modified polyolefin (A) used in the present invention is not limited, but at least one of polyethylene, polypropylene and propylene- ⁇ -olefin copolymer includes ⁇ , ⁇ -unsaturated carboxylic acid and acid anhydride thereof. Those obtained by grafting at least one of the above are preferred.
- the propylene- ⁇ -olefin copolymer is a copolymer in which ⁇ -olefin is copolymerized mainly with propylene.
- ⁇ -olefin for example, ethylene, 1-butene, 1-heptene, 1-octene, 4-methyl-1-pentene, vinyl acetate or the like can be used. Of these ⁇ -olefins, ethylene and 1-butene are preferred.
- the ratio of the propylene component to the ⁇ -olefin component of the propylene- ⁇ -olefin copolymer is not limited, but the propylene component is preferably 50 mol% or more, and more preferably 70 mol% or more.
- Examples of at least one of ⁇ , ⁇ -unsaturated carboxylic acid and acid anhydrides thereof include maleic acid, itaconic acid, citraconic acid, and acid anhydrides thereof.
- acid anhydrides are preferable, and maleic anhydride is more preferable.
- Specific examples include maleic anhydride-modified polypropylene, maleic anhydride-modified propylene-ethylene copolymer, maleic anhydride-modified propylene-butene copolymer, maleic anhydride-modified propylene-ethylene-butene copolymer, and the like.
- These crystalline acid-modified polyolefins can be used alone or in combination of two or more.
- a maleic anhydride-modified propylene-butene copolymer is preferable.
- the propylene component / 1-butene component (molar ratio) of the maleic anhydride-modified propylene-butene copolymer is preferably 90 to 50/10 to 50, more preferably 85 to 60/15 to 40. It is preferably 80 to 55/20 to 45, more preferably 75 to 60/25 to 40.
- the acid value of the crystalline acid-modified polyolefin (A) should be at least 5 mgKOH / g-resin, preferably 10 mgKOH, from the viewpoint of pot life and adhesion between the polyolefin resin substrate and the metal substrate.
- / G-resin or more more preferably 14 mgKOH / g-resin or more, still more preferably 16 mgKOH / g-resin or more, particularly preferably 18 mgKOH / g-resin or more, most preferably 20 mgKOH / g. More than -resin.
- the upper limit needs to be 50 mgKOH / g-resin or less, preferably 48 mgKOH / g-resin or less, more preferably 46 mgKOH / g-resin or less, still more preferably 44 mgKOH / g-resin or less. Preferably it is 42 mgKOH / g-resin or less, Most preferably, it is 40 mgKOH / g-resin or less.
- the acid value can be controlled by the amount (addition amount) of at least one kind of ⁇ , ⁇ -unsaturated carboxylic acid and acid anhydride thereof.
- the weight average molecular weight (Mw) of the crystalline acid-modified polyolefin (A) is preferably in the range of 40,000 to 180,000. More preferably, it is in the range of 50,000 to 160,000, more preferably in the range of 60,000 to 150,000, particularly preferably in the range of 70,000 to 140,000, and most preferably 80. , 13,000 to 130,000. If it is less than the above value, the cohesive force becomes weak and the adhesiveness may be inferior. On the other hand, when the above value is exceeded, there may be a problem in operability when bonding due to low fluidity. If it is in the said range, since hardening reaction with an epoxy resin is utilized, it is preferable.
- the crystallinity in the crystalline acid-modified polyolefin (A) means that the temperature is raised from ⁇ 100 ° C. to 250 ° C. at 20 ° C./min using a differential scanning calorimeter (DSC), and a clear melting is performed in the temperature raising process. This refers to the peak.
- DSC differential scanning calorimeter
- the melting point (Tm) of the crystalline acid-modified polyolefin (A) is preferably in the range of 50 ° C to 120 ° C. More preferably, it is in the range of 60 ° C to 100 ° C, and most preferably in the range of 70 ° C to 90 ° C. If it is less than the above value, the cohesive force derived from crystals becomes weak, and the adhesiveness and chemical resistance may be inferior. On the other hand, when the above value is exceeded, the solution stability and fluidity are low, and there may be a problem in operability when bonding.
- the heat of fusion ( ⁇ H) of the crystalline acid-modified polyolefin (A) is preferably in the range of 5 J / g to 60 J / g.
- a range of 10 J / g to 50 J / g is more preferable, and a range of 20 J / g to 40 J / g is most preferable. If it is less than the above value, the cohesive force derived from crystals becomes weak, and the adhesiveness and chemical resistance may be inferior. On the other hand, when the above value is exceeded, the solution stability and fluidity are low, and there may be a problem in operability when bonding.
- the production method of the crystalline acid-modified polyolefin (A) is not particularly limited.
- a radical graft reaction that is, a radical species is generated with respect to a polymer to be a main chain, and the radical species is used as a polymerization initiation point to produce an unsaturated carboxylic acid. Reaction for graft polymerization of acid and acid anhydride), and the like.
- organic peroxide is not particularly limited, but di-tert-butyl peroxyphthalate, tert-butyl hydroperoxide, dicumyl peroxide, benzoyl peroxide, tert-butyl peroxybenzoate, tert-butyl peroxy- Peroxides such as 2-ethylhexanoate, tert-butyl peroxypivalate, methyl ethyl ketone peroxide, di-tert-butyl peroxide, lauroyl peroxide; azobisisobutyronitrile, azobisisopropionitrile, etc. Examples thereof include azonitriles.
- the glycidylamine type epoxy resin (B1) used for this invention will not be specifically limited if it is an epoxy resin which has a 1 or more glycidyl group in 1 molecule. It is preferable to have two or more glycidyl groups in one epoxy resin molecule, more preferably three or more glycidyl groups in one molecule of epoxy resin, and four or more glycidyl groups in one molecule of epoxy resin. More preferably, it has.
- R is an aryl group which may have a substituent, and preferably a phenyl group which may have a substituent.
- the substituent of the aryl group is not particularly limited, but is an alkyl group having 1 to 5 carbon atoms, an alkoxy group having 1 to 5 carbon atoms, a hydroxyl group, an amino group, a glycidyl group, a glycidylamino group, or a glycidyl ether group. Is mentioned.
- X1 and X2 are each independently a linear alkylene group which may have a substituent having 1 to 5 carbon atoms, preferably 4 or less, more preferably 3 or less, and still more preferably Is 2 or less. Although it does not specifically limit as a substituent of the said alkylene group, A C1-C5 alkyl group, a C1-C5 alkoxy group, or an amino group is mentioned.
- m is 1 or 2
- n is 1 or 2.
- n is 1 or 2.
- either m or n is 2, more preferably m and n are both 2.
- glycidylamine type epoxy resin (B1) are not particularly limited, but include tetraglycidyldiaminodiphenylmethane, triglycidylparaaminophenol, tetraglycidylbisaminomethylcyclohexanone, N, N, N ′, N′-tetraglycidyl-m.
- -Glycidylamine type such as xylenediamine. Of these, N, N, N ′, N′-tetraglycidyl-m-xylenediamine is preferred.
- These glycidylamine type epoxy resins (B1) can be used alone or in combination of two or more.
- the blending amount of the glycidylamine type epoxy resin (B1) is preferably 0.01 parts by mass or more, and 0.05 parts by mass or more with respect to 100 parts by mass of the crystalline acid-modified polyolefin (A). More preferably, it is more preferably 0.1 parts by mass or more, particularly preferably 1 part by mass or more, and most preferably 2 parts by mass or more. If it is less than the above range, the catalytic action is not exhibited, and there are cases where adhesion at 80 ° C. or lower and aging adhesion and chemical resistance are low.
- the crosslinking reaction proceeds excessively, the rigidity becomes high, and the adhesiveness tends to be lowered. Further, the crosslinking reaction tends to proceed during storage of the adhesive composition solution, and the pot life tends to be reduced.
- the glycidyl ether type epoxy resin (B2) used for this invention will not be specifically limited if it is an epoxy resin which has a glycidyl ether group in a molecule
- it is an epoxy resin having two or more glycidyl groups in one molecule of the epoxy resin, and more preferably an epoxy resin having two or more glycidyl groups in one molecule of the epoxy resin and containing no nitrogen atom. .
- the blending amount of the glycidyl ether type epoxy resin (B2) is preferably 1 part by mass or more, more preferably 2 parts by mass or more, relative to 100 parts by mass of the crystalline acid-modified polyolefin (A). More preferably, it is more preferably 4 parts by mass or more, and most preferably 5 parts by mass or more. Further, it is preferably 50 parts by mass or less, more preferably 40 parts by mass or less, further preferably 30 parts by mass or less, particularly preferably 25 parts by mass or less, and 20 parts by mass or less. Most preferably it is. By setting it in the above range, excellent adhesiveness and chemical resistance can be expressed.
- glycidyl ether type epoxy resin (B2) are not particularly limited, and examples thereof include phenol novolac type epoxy resins and cresol novolac type epoxy resins, and these are viewpoints of adhesion to metal substrates and chemical resistance. To preferred. These glycidyl ether type epoxy resins (B2) can be used alone or in combination of two or more.
- the glycidylamine type epoxy resin (B1) and the glycidyl ether type epoxy resin (B2) are used in combination as essential components.
- the glycidylamine type epoxy resin (B1) and the glycidyl ether type epoxy resin (B2) are used in combination as essential components.
- excellent adhesiveness and chemical resistance can be expressed. That is, the glycidylamine type epoxy resin (B1) has a reaction and curing action between the crystalline acid-modified polyolefin (A) and the glycidyl ether type epoxy resin (B2).
- the glycidylamine type epoxy resin (B1) is composed of crystalline acid-modified polyolefin (A) and glycidylamine type epoxy resin (B1), glycidylamine type epoxy resin (B1), and glycidyl ether type epoxy resin (B2), Since it has a reaction and curing catalytic action of the glycidylamine type epoxy resin (B1) and the glycidyl ether type epoxy resin (B2), it is bonded at 80 ° C. or lower by adhesion, and adhesion to a metal substrate in aging And chemical resistance can be improved.
- the total amount of the glycidylamine type epoxy resin (B1) and the glycidyl ether type epoxy resin (B2) is preferably 2 to 70 parts by mass with respect to 100 parts by mass of the crystalline acid-modified polyolefin (A).
- the amount is more preferably 5 to 50 parts by mass, and most preferably 10 to 30 parts by mass. If the amount is less than the above range, sufficient curing effect may not be obtained and the adhesiveness and chemical resistance may be low, and if it exceeds the above range, it is not preferable from the viewpoints of pot life and reduced adhesion between the olefin substrate and cost.
- the blending amount of the glycidylamine type epoxy resin (B1) is preferably 1 to 50% by mass, more preferably 2 to 30% by mass, and most preferably 3 to 10% by mass of the entire epoxy resin. . If the blending amount is less than the above, the catalytic action does not appear and the adhesion and chemical resistance in low temperature bonding and aging may be low. If it exceeds the above, the crosslinking reaction proceeds excessively and the rigidity becomes high. The adhesiveness tends to decrease. Further, the crosslinking reaction tends to proceed during storage of the adhesive composition solution, and the pot life tends to be reduced.
- epoxy resins can be used in combination as the epoxy resin used in the present invention.
- glycidyl ester type such as hexahydrophthalic acid glycidyl ester, dimer acid glycidyl ester, triglycidyl isocyanurate, or 3,4-epoxycyclohexylmethylcarboxylate, epoxidized polybutadiene, epoxidized soybean oil, etc.
- Group epoxides and the like and may be used alone or in combination of two or more.
- the acid anhydride monomer (C) used in the present invention is not particularly limited as long as it is a compound having one or more acid anhydride rings in one molecule.
- the crosslinking density is reduced. For example, even when water is mixed in the electrolytic solution, the chemical resistance (electrolytic solution resistance) of the adhesive composition does not decrease, and a good state can be maintained.
- the acid value of the acid anhydride monomer is preferably 100 mgKOH / g or more, more preferably 150 mgKOH / g or more, and further preferably 200 mgKOH / g or more. If it is less than the above value, the curing accelerating effect is not exhibited, and the chemical resistance of the adhesive composition may be lowered. Moreover, it is preferable that an acid value is 1000 mgKOH / g or less, It is more preferable that it is 900 mgKOH / g or less, It is further more preferable that it is 800 mgKOH / g or less. If it exceeds the above value, pot life may be lowered.
- the compounding amount of the acid anhydride monomer (C) used in the present invention is preferably 1 part by mass or more and more preferably 2 parts by mass or more with respect to 100 parts by mass of the crystalline acid-modified polyolefin (A). It is preferably 3 parts by mass or more, more preferably 4 parts by mass or more, and most preferably 5 parts by mass or more. Further, it is preferably 50 parts by mass or less, more preferably 48 parts by mass or less, further preferably 45 parts by mass or less, particularly preferably 40 parts by mass or less, and 35 parts by mass or less. Most preferably it is. By setting it in the above range, excellent adhesiveness and chemical resistance can be expressed.
- the heterocyclic compound (D) having two or more nitrogen atoms used in the present invention is a heterocyclic compound having two or more nitrogen atoms in one molecule, and has two nitrogen atoms as a ring component of the heterocyclic ring. It is preferable that there is more.
- the heterocyclic compound (D) having two or more nitrogen atoms is an excellent curing accelerating action between the crystalline polyolefin (A) and the glycidylamine type epoxy resin (B1) and / or the glycidyl ether type epoxy resin (B2) ( Catalytic action).
- the chemical resistance (electrolytic solution resistance) of the adhesive composition Does not decrease, and a good state can be maintained. Furthermore, by using together with the said acid anhydride monomer (C), a crosslinking density can be raised efficiently and very outstanding adhesiveness and chemical resistance can be expressed. For example, even when moisture is mixed in the electrolytic solution, the chemical resistance (electrolytic solution resistance) of the adhesive composition does not decrease, and an extremely good state can be maintained.
- the heterocyclic compound (D) having two or more nitrogen atoms is not particularly limited, and aliphatic heterocyclic compounds such as piperazine compounds, 5-membered aromatic heterocyclic compounds such as imidazole compounds and pyrazole compounds, and pyrimidine compounds.
- aliphatic heterocyclic compounds such as piperazine compounds, 5-membered aromatic heterocyclic compounds such as imidazole compounds and pyrazole compounds, and pyrimidine compounds.
- Pyridazine compounds, pyrazine compounds, 6-membered aromatic heterocyclic compounds such as triazine compounds, quinazoline compounds, phthalazine compounds, pteridine compounds, benzimidazole compounds, purine compounds, and other polycyclic aromatic heterocyclic compounds
- an imidazole compound is preferable from the viewpoint of catalytic effect and chemical resistance.
- the compounding quantity of the heterocyclic compound (D) which has two or more nitrogen is 0.01 mass part or more with respect to 100 mass parts of crystalline acid-modified polyolefin (A), and 0.02 mass part More preferably, it is more preferably 0.05 parts by mass or more, particularly preferably 0.1 parts by mass or more, and most preferably 0.2 parts by mass or more. If it is less than the above range, the curing promoting (catalytic) action may not be exhibited, and bonding at 80 ° C. or lower may be difficult. For example, when the aging is performed at about 40 ° C.
- the adhesiveness and chemical resistance may be lowered, or it may be necessary to provide a long aging time.
- it is preferably 5 parts by mass or less, more preferably 4 parts by mass or less, further preferably 3 parts by mass or less, particularly preferably 2 parts by mass or less, and 1 part by mass or less. Most preferably it is.
- the crosslinking reaction proceeds excessively, the rigidity becomes high, and the adhesiveness tends to be lowered. Further, the crosslinking reaction tends to proceed during storage of the adhesive composition solution, and the pot life tends to be reduced. Moreover, it is not preferable also from a viewpoint of manufacturing cost.
- the compounding amount of the heterocyclic compound (D) having two or more nitrogen is 1 to 100% by mass with respect to the total compounding amount of the glycidylamine type epoxy resin (B1) and the glycidyl ether type epoxy resin (B2). It is preferably 2 to 70% by mass, more preferably 3 to 50% by mass.
- the blending amount is less than the above, the catalytic action is not exhibited, and there are cases where adhesion and chemical resistance at low temperature bonding and aging are low. If it exceeds the above range, the crosslinking reaction proceeds excessively, the rigidity becomes high and the adhesiveness tends to decrease, and the crosslinking reaction tends to proceed during solution storage of the adhesive composition, and the pot life tends to decrease. Moreover, it is not preferable also from a viewpoint of manufacturing cost.
- the heterocyclic compound (D) having two or more nitrogen atoms may be blended alone, a plurality of compounds may be used in combination, or a combination with other curing accelerators.
- Other curing accelerators include carboxylic acid metal salts, tertiary amines, quaternary ammonium salts, organic peroxides, hydrazine compounds, metal chelate compounds, thioureas, phosphorus-containing compounds, basic vulcanizing agents, and the like. Can be mentioned.
- Examples of the carboxylic acid metal salt include metal salts of carboxylic acids having 1 to 30 carbon atoms.
- Examples of the carboxylic acid constituting the carboxylic acid metal salt include acetic acid, butyric acid, octanoic acid, decanoic acid, lauric acid, myristic acid, palmitic acid, stearic acid, oleic acid, behenic acid, octenoic acid, erucic acid, and elaidin.
- Acids adipic acid, malonic acid, succinic acid, glutaric acid, citric acid, tartaric acid, malic acid, diglycolic acid and other aliphatic carboxylic acids; benzoic acid, chlorobenzoic acid, anisic acid, aminobenzoic acid, phthalic acid, terephthalic acid Aromatic carboxylic acids such as acid, naphthoic acid, naphthalenedicarboxylic acid, and benzenetricarboxylic acid; naphthenic acid; acetone acid and the like.
- a metal which comprises the said carboxylic acid metal salt Li, Na, K, Mg, Ca, Zn, Al, Cu, Pb, Co, Fe, Mn, Sn, Ti etc. are mentioned, for example.
- Specific examples of the carboxylic acid metal salt include lithium acetate, sodium acetate, magnesium acetate, aluminum acetate, potassium butyrate, calcium butyrate, zinc butyrate, sodium octoate, calcium octoate, potassium decanoate, magnesium decanoate, and decane.
- Zinc oxide lithium laurate, sodium laurate, calcium laurate, aluminum laurate, potassium myristate, sodium myristate, aluminum myristate, sodium palmitate, zinc palmitate, magnesium palmitate, sodium stearate, potassium stearate, Calcium stearate, zinc stearate, sodium oleate, sodium behenate, sodium benzoate, zinc benzoate, sodium phthalate, phthalic acid Minium, magnesium terephthalate, calcium naphthalenedicarboxylate, dibutyltin laurate, tributyltin laurate, dioctyltin laurate, tributyltin acetate, dibutyltin diacetate, dioctyltin diacetate, dibutyltin 2-ethylhexoate, tetrabutyl titanate, tetraisobutyl Examples thereof include titanate, tetra-2-ethylhexyl titanate, co
- lithium laurate, sodium laurate, calcium laurate, aluminum laurate, potassium myristate, sodium myristate, aluminum myristate, sodium palmitate, zinc palmitate, magnesium palmitate, sodium stearate examples include potassium stearate, calcium stearate, zinc stearate, and sodium oleate.
- a polymer having a metal salt structure of carboxylic acid can also be used. Such polymers include ethylene and radically polymerizable carboxylic acid group IA, IIA, IIB, and IIIB metal (eg, Li, Na, K, Mg, Ca, Zn, Al, etc.) salts.
- Examples thereof include those having a polymerized structure; those having a structure in which ethylene, a metal salt of a radically polymerizable carboxylic acid and other radically polymerizable carboxylic acid and / or a derivative thereof are copolymerized in a multi-component system.
- Examples of the tertiary amines include dimethylaniline, triethanolamine, dimethyl-p-toluidine, and the like.
- the hydrazine compound include 1-acetyl-2-phenylhydrazine.
- vanadium acetylacetonate etc. are mentioned, for example.
- Examples of the thioureas include dimethylphosphine and triphenylphosphine.
- Examples of the phosphorus-containing compound include dimethylphosphine and triphenylphosphine.
- Examples of the basic vulcanizing agent include hexamethylenetetraamine, n-butyraldehyde-aniline condensate, and the like.
- Organic solvent (E) used in the present invention contains crystalline acid-modified polyolefin (A), glycidylamine type epoxy resin (B1), glycidyl ether type epoxy resin (B2), acid anhydride monomer (C), and nitrogen. It will not be specifically limited if it dissolves the heterocyclic compound (D) which has one or more.
- aromatic hydrocarbons such as benzene, toluene and xylene
- aliphatic hydrocarbons such as hexane, heptane, octane and decane
- alicyclic carbons such as cyclohexane, cyclohexene, methylcyclohexane and ethylcyclohexane
- Halogenated hydrocarbons such as hydrogen, trichloroethylene, dichloroethylene, chlorobenzene, chloroform, alcohol solvents such as methanol, ethanol, isopropyl alcohol, butanol, pentanol, hexanol, propanediol, phenol, acetone, methyl isobutyl ketone, Ketone solvents such as methyl ethyl ketone pentanone, hexanone, cyclohexanone, isophorone, acetophenone, cellsolves such as methyl cellosolve
- the organic solvent (E) is preferably 80 parts by mass or more, more preferably 90 parts by mass or more, and 100 parts by mass or more with respect to 100 parts by mass of the crystalline acid-modified polyolefin (A). Is more preferable, and 110 parts by mass or more is particularly preferable. If it is less than the said range, a solution state and pot life property may fall. Further, it is preferably 1000 parts by mass or less, more preferably 900 parts by mass or less, still more preferably 800 parts by mass or less, and particularly preferably 700 parts by mass or less. Exceeding the above range may be disadvantageous in terms of production cost and transportation cost.
- the organic solvent (E) is selected from the group consisting of aromatic hydrocarbons, aliphatic hydrocarbons, alicyclic hydrocarbons and halogenated hydrocarbons from the viewpoint of the solution state and pot life properties of the adhesive composition.
- a mixed solution of at least one solvent (E2) selected from the group consisting of at least one solvent (E1), an alcohol solvent, a ketone solvent, an ester solvent, and a glycol ether solvent is preferable.
- the solution state and pot life of the adhesive composition may be lowered.
- the solvent (C1) is an aromatic hydrocarbon or an alicyclic hydrocarbon
- the solvent (E2) is a ketone solvent.
- An adhesive composition according to the present invention contains the crystalline acid-modified polyolefin (A), a glycidylamine type epoxy resin (B1), a glycidyl ether type epoxy resin (B2), and an organic solvent (E), and further an acid. It is a composition containing any one of an anhydride monomer (C) and a heterocyclic compound (D) having two or more nitrogen atoms.
- It is a composition containing a heterocyclic compound (D).
- Crystalline acid-modified polyolefin (A), glycidylamine type epoxy resin (B1), glycidyl ether type epoxy resin (B2), acid anhydride monomer (C), and heterocyclic compound (D) having two or more nitrogen atoms are It may be dissolved or dispersed in the organic solvent (E). It is preferably dissolved from the viewpoint of pot life.
- the adhesive composition according to the present invention includes the modified polyolefin (A), glycidylamine type epoxy resin (B1), glycidyl ether type epoxy resin (B2), acid anhydride monomer (C) as long as the performance of the present invention is not impaired.
- various additives can be blended and used. Although it does not specifically limit as an additive, It is preferable to use a flame retardant, a pigment, an antiblocking agent, etc.
- the laminate of the present invention is obtained by laminating a polyolefin resin substrate and a metal substrate with the adhesive composition according to the present invention.
- the adhesive composition is applied to the surface of the metal substrate using an appropriate application means such as a roll coater or a bar coater, and dried. After drying, while the adhesive layer formed on the surface of the metal substrate is in a molten state, a laminate structure can be obtained by laminating and bonding a polyolefin resin substrate to the coated surface.
- the thickness of the adhesive layer formed by the adhesive composition is not particularly limited, but is preferably 0.5 to 10 ⁇ m, more preferably 0.8 to 9.5 ⁇ m, and 1 to 9 ⁇ m. More preferably.
- ⁇ Polyolefin resin substrate> What is necessary is just to select suitably from a conventionally well-known polyolefin resin as a polyolefin resin base material.
- a conventionally well-known polyolefin resin for example, although not particularly limited, polyethylene, polypropylene, ethylene-propylene copolymer, and the like can be used. Among these, the use of an unstretched polypropylene film (hereinafter also referred to as CPP) is preferable.
- the thickness is not particularly limited, but is preferably 20 to 100 ⁇ m, more preferably 25 to 95 ⁇ m, and even more preferably 30 to 90 ⁇ m. In addition, you may mix
- Metal base material Although it does not specifically limit as a metal base material, various metals, such as aluminum, copper, steel, zinc, duralumin, die-casting, and its alloy can be used. Moreover, as the shape, arbitrary shapes, such as metal foil, a rolled steel plate, a panel, a pipe, a can, and a cap, can be taken. In general, aluminum foil is preferable from the viewpoint of workability and the like. Although it varies depending on the purpose of use, it is generally used in the form of a sheet having a thickness of 0.01 to 10 mm, preferably 0.02 to 5 mm. Moreover, about these metal base materials, it is desirable to use what surface-treated in advance from a viewpoint of corrosion resistance and adhesiveness, and specifically includes chromate treatment.
- the liquid containing the resin was centrifuged to separate and purify an acid-modified propylene-butene copolymer grafted with maleic anhydride, (poly) maleic anhydride and a low molecular weight product. Thereafter, by drying at 70 ° C. under reduced pressure for 5 hours, a maleic anhydride-modified propylene-butene copolymer (PO-1, acid value 48 mgKOH / g-resin, weight average molecular weight 50,000, Tm 75 ° C., ⁇ H25J / g) was obtained.
- PO-1 acid value 48 mgKOH / g-resin, weight average molecular weight 50,000, Tm 75 ° C., ⁇ H25J / g
- Production Example 2 A maleic anhydride-modified propylene-butene copolymer (PO-2, acid value 25 mgKOH / g-resin, weight average) was obtained in the same manner as in Production Example 1 except that the amount of maleic anhydride charged was changed to 20 parts by mass. Molecular weight 80,000, Tm 75 ° C., ⁇ H 30 J / g) was obtained.
- Production Example 3 A maleic anhydride-modified propylene-butene copolymer (with the same procedure as in Production Example 1 except that the amount of maleic anhydride charged was changed to 3 parts by mass and the amount of di-tert-butyl peroxide was changed to 0.5 parts by mass ( PO-3, acid value 5 mg KOH / g-resin, weight average molecular weight 180,000, Tm 80 ° C., ⁇ H 25 J / g).
- Production Example 4 A maleic anhydride-modified propylene-butene copolymer (PO-4, acid value 55 mgKOH / g-resin, weight average) was obtained in the same manner as in Production Example 1 except that the amount of maleic anhydride charged was changed to 30 parts by mass. Molecular weight 40,000, Tm 70 ° C., ⁇ H 25 J / g) was obtained.
- Production Example 5 A maleic anhydride-modified propylene-butene copolymer was prepared in the same manner as in Production Example 1 except that the amount of maleic anhydride charged was changed to 2 parts by mass and the amount of di-tert-butyl peroxide was changed to 0.5 parts by mass.
- PO-5 acid value 3 mg KOH / g-resin, weight average molecular weight 200,000, Tm 80 ° C., ⁇ H 25 J / g).
- Example 1 500 parts by mass of main agent 1, 20 parts by mass of jER (registered trademark) 152 as glycidyl ether type epoxy resin (B2) as a curing agent, and 2 of TETRAD (registered trademark) -X as glycidylamine type epoxy resin (B1) 20 parts by mass of Guatemalacid (registered trademark) DDSA which is an acid anhydride monomer (C) as an additive was blended to obtain an adhesive composition.
- Table 2 shows the evaluation results of pot life, adhesiveness and chemical resistance.
- Examples 2 to 69, Comparative Examples 1 to 7 The main agents 1 to 12 and the curing agents were changed as shown in Tables 2 to 5, and Examples 2 to 69 and Comparative Examples 1 to 7 were carried out in the same manner as in Example 1. The blending amounts, pot life properties, adhesiveness and chemical resistance are shown in Tables 2 to 5.
- the curing agents used in Tables 2 to 5 are as follows.
- the acid value (mgKOH / g-resin) of the crystalline acid-modified polyolefin (A) in the present invention is the amount of KOH required to neutralize 1 g of the acid-modified polyolefin (A). JIS K0070 ( 1992).
- the acid value (mgKOH / g) of the acid anhydride monomer (C) in the present invention is a value calculated by the following formula using the molecular weight (M) of the acid anhydride monomer and the number of succinic anhydride groups (n). .
- Acid value (mgKOH / g-resin) [Molecular weight of succinic anhydride (M) ⁇ (n) ⁇ 2 ⁇ Molecular weight of potassium hydroxide ⁇ 1000 (mg) / Molecular weight of succinic anhydride] Molecular weight of succinic anhydride: 100.07, molecular weight of potassium hydroxide: 56.11
- the melting point and heat of fusion in the present invention are increased at a rate of 20 ° C./minute using a differential scanning calorimeter (hereinafter DSC, manufactured by TA Instruments Japan, Q-2000). It is a value measured from the top temperature and area of the melting peak when heated and melted into a cooled resin and then heated and melted again.
- DSC differential scanning calorimeter
- Pot life property refers to the stability of the solution immediately after compounding or after a certain time has elapsed after compounding a crystalline acid-modified polyolefin with a crosslinking agent or curing agent. If the pot life is good, it means that the viscosity of the solution is small and can be stored for a long time. If the pot life is poor, the viscosity of the solution increases (thickens). It means that gelation occurs, application to a substrate becomes difficult, and long-term storage is impossible.
- the pot life properties of the adhesive compositions obtained in Examples 1 to 69 and Comparative Examples 1 to 7 were stored at 25 ° C. and 40 ° C. for 24 hours, and then the solution viscosity at 25 ° C.
- the polyolefin resin substrate is a metal substrate that is an aluminum foil (manufactured by Sumi Light Aluminum Foil Co., Ltd., 8079-0, 40 ⁇ m thick) chromated.
- An unstretched polypropylene film (Pyrene (registered trademark) film CT manufactured by Toyobo Co., Ltd., thickness 40 ⁇ m) (hereinafter also referred to as CPP) was used.
- the adhesive compositions obtained in Examples 1 to 69 and Comparative Examples 1 to 7 were applied to a metal substrate using a bar coater so that the thickness of the adhesive layer after drying was adjusted to 3 ⁇ m.
- the coated surface was dried for 1 minute at 100 ° C. using a hot air dryer to obtain an adhesive layer having a thickness of 3 ⁇ m.
- a polyolefin resin base material is superposed on the surface of the adhesive layer, and bonded at 80 ° C., 0.3 MPa, 1 m / min using a small desktop test laminator (SA-1010-S) manufactured by Tester Sangyo Co., Ltd., and 40 ° C.
- SA-1010-S small desktop test laminator manufactured by Tester Sangyo Co., Ltd., and 40 ° C.
- the laminate was obtained by curing for 120 hours at 50% RH.
- the laminate obtained as described above was evaluated by the following method.
- ⁇ T-type peel test> Based on the test method of ASTM-D1876-61, the peel strength at a tensile speed of 50 mm / min was measured in a 25 ° C environment using Tensilon RTM-100 manufactured by Orientec Corporation. The peel strength (N / cm) between the metal substrate / polyolefin resin substrate was the average of five test values.
- material breakage material breakage means that peeling does not occur at the metal substrate / CPP interface, The metal base or CPP is destroyed.
- electrolytic solution resistance Chemical resistance by an electrolytic solution test (hereinafter also referred to as electrolytic solution resistance) in order to examine the utility as a packaging material of a lithium ion battery which is one of the usage forms of an aluminum foil and a CPP laminate. ) was evaluated.
- the sample was added at 300 ppm for 3 days at 85 ° C., or immersed in an electrolyte solution added with 500 ppm of water at 85 ° C. for 5 days.
- the laminate was taken out, washed with ion-exchanged water, wiped with water with a paper wiper, sufficiently dried in water, cut into a size of 100 mm ⁇ 15 mm, and evaluated for chemical resistance by a T-type peel test.
- the adhesive composition according to the present invention contains any one of an acid-modified polyolefin, an epoxy resin, an organic solvent, an acid anhydride monomer, and a heterocyclic compound having two or more nitrogen atoms, and thickens even when stored for a long period of time. It is possible to maintain good pot life without causing gelation and to achieve both good adhesion between the metal substrate and the polyolefin resin substrate. Therefore, the laminated structure of the polyolefin resin substrate and the metal substrate formed from the adhesive composition of the present invention is not only used in the fields of home appliance outer panels, furniture materials, building interior members, etc. It can also be widely used as a packaging material (pouch form) for lithium batteries used in telephones, video cameras and the like.
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Abstract
Description
本発明で用いる結晶性酸変性ポリオレフィン(A)は限定的ではないが、ポリエチレン、ポリプロピレン及びプロピレン-α-オレフィン共重合体の少なくとも1種に、α,β-不飽和カルボン酸及びその酸無水物の少なくとも1種をグラフトすることにより得られるものが好ましい。
本発明に用いるグリシジルアミン型エポキシ樹脂(B1)は、1分子中に1個以上のグリシジル基を有するエポキシ樹脂であれば特に限定されない。エポキシ樹脂1分子中に2個以上のグリシジル基を有することが好ましく、エポキシ樹脂1分子中に3個以上のグリシジル基を有することがより好ましく、エポキシ樹脂1分子中に4個以上のグリシジル基を有することがさらに好ましい。
本発明に用いるグリシジルエーテル型エポキシ樹脂(B2)は、分子内にグリシジルエーテル基を有するエポキシ樹脂であれば特に限定されない。好ましくはエポキシ樹脂1分子中に2個以上のグリシジル基を有するエポキシ樹脂であり、さらに好ましくはエポキシ樹脂1分子中に2個以上のグリシジル基を有し、かつ窒素原子を含有しないエポキシ樹脂である。
本発明で用いる酸無水物モノマー(C)は、1分子中に1個以上の酸無水物環を有する化合物であれば特に限定されず、無水フタル酸、無水トリメリット酸、テトラヒドロ無水フタル酸、メチルテトラヒドロ無水フタル酸、メチルペンタヒドロ無水フタル酸、メチルトリヒドロ無水フタル酸、トリアルキルテトラヒドロ無水フタル酸、メチルシクロヘキセンジカルボン酸無水物、無水ヘット酸、テトラブロモ無水フタル酸などの脂環構造、または芳香環構造を有するものや、無水コハク酸、無水マレイン酸、無水グルタル酸、ブチルコハク酸無水物、ヘキシルコハク酸無水物、オクチルコハク酸無水物、ドデシルコハク酸無水物、ドデセニルコハク酸無水物、テトラプロペニルコハク酸無水物、ブチルマレイン酸無水物、ペンチルマレイン酸無水物、ヘキシルマレイン酸無水物、オクチルマレイン酸無水物、デシルマレイン酸無水物、ドデシルマレイン酸無水物、ブチルグルタミン酸無水物、ヘキシルグルタミン酸無水物、ヘプチルグルタミン酸無水物、オクチルグルタミン酸無水物、デシルグルタミン酸無水物、ドデシルグルタミン酸無水物などのアルキル鎖と酸無水物を有するものが挙げられ、一種のみを単独で用いてもよいし、複数を併用しても良い。具体的には、新日本理化(株)製のリカシッド(登録商標)などが上市されており使用できる。
本発明で用いる窒素を2つ以上有する複素環式化合物(D)は、1分子中に2個以上の窒素原子を有する複素環式化合物であり、複素環の環構成成分として窒素原子が2個以上あることが好ましい。窒素を2つ以上有する複素環式化合物(D)は、結晶性ポリオレフィン(A)と、グリシジルアミン型エポキシ樹脂(B1)および/またはグリシジルエーテル型エポキシ樹脂(B2)との優れた硬化促進作用(触媒作用)を有する。そのため、窒素を2つ以上有する複素環式化合物(D)を含有することで、例えば、電解液に水分が混入した場合であっても、接着剤組成物の耐薬品性(耐電解液性)が低下することはなく、良好な状態を維持することができる。さらに、前記酸無水物モノマー(C)と併用することによって、架橋密度を効率的に高めることができ、極めて優れた接着性および耐薬品性を発現することができる。例えば、電解液に水分が混入した場合であっても、接着剤組成物の耐薬品性(耐電解液性)が低下することはなく、極めて良好な状態を維持することができる。
本発明で用いる有機溶剤(E)は、結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、酸無水物モノマー(C)、および窒素を2つ以上有する複素環式化合物(D)を溶解させるものであれば、特に限定されない。具体的には、例えば、ベンゼン、トルエン、キシレン等の芳香族炭化水素、ヘキサン、ヘプタン、オクタン、デカン等の脂肪族系炭化水素、シクロヘキサン、シクロヘキセン、メチルシクロヘキサン、エチルシクロへキサン等の脂環族炭化水素、トリクロルエチレン、ジクロルエチレン、クロルベンゼン、クロロホルム等のハロゲン化炭化水素、メタノール、エタノール、イソプロピルアルコール、ブタノール、ペンタノール、ヘキサノール、プロパンジオール、フェノール等のアルコール系溶剤、アセトン、メチルイソブチルケトン、メチルエチルケトンペンタノン、ヘキサノン、シクロヘキサノン、イソホロン、アセトフェノン等のケトン系溶剤、メチルセルソルブ、エチルセルソルブ等のセルソルブ類、酢酸メチル、酢酸エチル、酢酸ブチル、プロピオン酸メチル、ギ酸ブチル等のエステル系溶剤、エチレングリコールモノ-n-ブチルエーテル、エチレングリコールモノ-iso-ブチルエーテル、エチレングリコールモノ-tert-ブチルエーテル、ジエチレングリコールモノ-n-ブチルエーテル、ジエチレングリコールモノ-iso-ブチルエーテル、トリエチレングリコールモノ-n-ブチルエーテル、テトラエチレングリコールモノ-n-ブチルエーテル等のグリコールエーテル系溶剤等を使用することができ、これら1種または2種以上を併用することができる。
本発明にかかる接着剤組成物は、前記結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、および有機溶剤(E)を含有し、さらに酸無水物モノマー(C)および窒素を2つ以上有する複素環式化合物(D)のいずれか一方を含有する組成物である。好ましくは結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、および有機溶剤(E)、酸無水物モノマー(C)および窒素を2つ以上有する複素環式化合物(D)を含有する組成物である。結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、酸無水物モノマー(C)、および窒素を2つ以上有する複素環式化合物(D)は有機溶剤(E)に溶解しても良いし、分散しても良い。ポットライフ性の観点から溶解していることが好ましい。
本発明の積層体は、ポリオレフィン樹脂基材と金属基材を本発明にかかる接着剤組成物で積層したものである。
前記接着剤組成物により形成される接着剤層の厚みは、特に限定されないが、0.5~10μmにすることが好ましく、0.8~9.5μmにすることがより好ましく、1~9μmにすることがさらに好ましい。
ポリオレフィン樹脂基材としては、従来から公知のポリオレフィン樹脂の中から適宜選択すればよい。例えば、特に限定されないが、ポリエチレン、ポリプロピレン、エチレン-プロピレン共重合体などを用いることができる。中でも、ポリプロピレンの無延伸フィルム(以下、CPPともいう。)の使用が好ましい。その厚さは、特に限定されないが、20~100μmであることが好ましく、25~95μmであることがより好ましく、30~90μmであることがさらに好ましい。なお、ポリオレフィン樹脂基材には必要に応じて顔料や種々の添加物を配合してもよい。
金属基材としては、特に限定されないが、例えばアルミニウム、銅、鉄鋼、亜鉛、ジュラルミン、ダイカストなどの各種金属およびその合金を使用することができる。また、その形状としては、金属箔、圧延鋼板、パネル、パイプ、カン、キャップなど任意の形状を取り得ることができる。一般的には、加工性等の観点からアルミ二ウム箔が好ましい。また、使用目的によっても異なるが、一般的には0.01~10mm、好ましくは0.02~5mmの厚みのシートの形で使用される。
また、また、これら金属基材については、耐腐食性、接着性の観点から表面を予め表面処理を施したものを用いることが望ましく、具体的にはクロメート処理などが挙げられる。
製造例1
1Lオートクレーブに、プロピレン-ブテン共重合体(三井化学社製「タフマー(登録商標)XM7080」)100質量部、トルエン150質量部及び無水マレイン酸25質量部、ジ-tert-ブチルパーオキサイド6質量部を加え、140℃まで昇温した後、更に3時間撹拌した。その後、得られた反応液を冷却後、多量のメチルエチルケトンが入った容器に注ぎ、樹脂を析出させた。その後、当該樹脂を含有する液を遠心分離することにより、無水マレイン酸がグラフト重合した酸変性プロピレン-ブテン共重合体と(ポリ)無水マレイン酸および低分子量物とを分離、精製した。その後、減圧下70℃で5時間乾燥させることにより、無水マレイン酸変性プロピレン-ブテン共重合体(PO-1、酸価48mgKOH/g-resin、重量平均分子量50,000、Tm75℃、△H25J/g)を得た。
無水マレイン酸の仕込み量を20質量部に変更した以外は製造例1と同様にすることにより、無水マレイン酸変性プロピレン-ブテン共重合体(PO-2、酸価25mgKOH/g-resin、重量平均分子量80,000、Tm75℃、△H30J/g)を得た。
無水マレイン酸の仕込み量を3質量部、ジ-tert-ブチルパーオキサイドを0.5質量部に変更した以外は製造例1と同様にすることにより、無水マレイン酸変性プロピレン-ブテン共重合体(PO-3、酸価5mgKOH/g-resin、重量平均分子量180,000、Tm80℃、△H25J/g)を得た。
無水マレイン酸の仕込み量を30質量部に変更した以外は製造例1と同様にすることにより、無水マレイン酸変性プロピレン-ブテン共重合体(PO-4、酸価55mgKOH/g-resin、重量平均分子量40,000、Tm70℃、△H25J/g)を得た。
無水マレイン酸の仕込み量を2質量部、ジ-tert-ブチルパーオキサイドを0.5質量部に変更した以外は製造例1と同様にすることにより、無水マレイン酸変性プロピレン-ブテン共重合体(PO-5、酸価3mgKOH/g-resin、重量平均分子量200,000、Tm80℃、△H25J/g)を得た。
水冷還流凝縮器と撹拌機を備えた500mlの四つ口フラスコに、製造例1で得られた無水マレイン酸変性プロピレン-ブテン共重合体(PO-1)を100質量部、メチルシクロヘキサンを280質量部およびメチルエチルケトンを120質量部仕込み、撹拌しながら80℃まで昇温し、撹拌を1時間続けることで主剤1を得た。溶液状態を表1に示す。
結晶性酸変性ポリオレフィンおよび有機溶剤を表1に示すとおりに変更し、主剤1と同様な方法で主剤2~12を作製した。配合量、溶液状態を表1に示す。
主剤1を500質量部、硬化剤としてグリシジルエーテル型エポキシ樹脂(B2)であるjER(登録商標)152を20質量部、グリシジルアミン型エポキシ樹脂(B1)であるTETRAD(登録商標)-Xを2質量部、添加剤として酸無水物モノマー(C)であるリカシッド(登録商標)DDSAを20質量部配合し、接着剤組成物を得た。ポットライフ性、接着性および耐薬品性の評価結果を表2に示す。
主剤1~12および各硬化剤を表2~5に示すとおりに変更し、実施例1と同様な方法で実施例2~69、比較例1~7を行った。配合量、ポットライフ性、接着性および耐薬品性を表2~5に示す。
<グリシジルアミン型エポキシ樹脂(B1)>
N,N,N’,N’-テトラグリシジル-m-キシレンジアミン:TETRAD(登録商標)-X(三菱ガス化学社製)
<グリシジルエーテル型エポキシ樹脂(B2)>
フェノールノボラック型エポキシ樹脂:jER(登録商標)152(三菱化学社製)
o-クレゾールノボラック型エポキシ樹脂:YDCN-700-3(新日鉄住金化学社製)
<その他の硬化剤>
ポリイソシアネート:デュラネート(登録商標)TPA-100(旭化成社製)
シランカップリング剤:KBM-403(信越シリコーン社製)
<酸無水物モノマー(C)>
テトラプロペニル無水コハク酸:リカシッド(登録商標)DDSA
テトラヒドロ無水フタル酸:リカシッド(登録商標)TH
<窒素を2つ以上有する複素環式化合物(D)>
1-ベンジル-2-メチルイミダゾール:キュアゾール(登録商標)1B2MZ(四国化成社製)
酸価の測定
<結晶性酸変性ポリオレフィン(A)>
本発明における結晶性酸変性ポリオレフィン(A)の酸価(mgKOH/g-resin)は、1gの酸変性ポリオレフィン(A)を中和するのに必要とするKOH量のことであり、JIS K0070(1992)の試験方法に準じて、測定した。具体的には、100℃に温度調整したキシレン100gに、酸変性ポリオレフィン1gを溶解させた後、同温度でフェノールフタレインを指示薬として、0.1mol/L水酸化カリウムエタノール溶液[商品名「0.1mol/Lエタノール性水酸化カリウム溶液」、和光純薬(株)製]で滴定を行った。この際、滴定に要した水酸化カリウム量をmgに換算して酸価(mgKOH/g-resin)を算出した。
本発明における酸無水物モノマー(C)の酸価(mgKOH/g)は、酸無水物モノマーの分子量(M)、無水コハク酸基の数(n)を用いて下記式により算出した値である。酸価(mgKOH/g-resin)=[無水コハク酸の分子量(M)×(n)×2×水酸化カリウムの分子量×1000(mg)/無水コハク酸の分子量]
無水コハク酸の分子量:100.07、水酸化カリウムの分子量:56.11
本発明における重量平均分子量は日本ウォーターズ社製ゲルパーミエーションクロマトグラフAlliance e2695(以下、GPC、標準物質:ポリスチレン樹脂、移動相:テトラヒドロフラン、カラム:Shodex KF-806 + KF-803、カラム温度:40℃、流速:1.0ml/分、検出器:フォトダイオードアレイ検出器(波長254nm = 紫外線))によって測定した値である。
本発明における融点、融解熱量は示差走査熱量計(以下、DSC、ティー・エー・インスツルメント・ジャパン製、Q-2000)を用いて、20℃/分の速度で昇温融解、冷却樹脂化して、再度昇温融解した際の融解ピークのトップ温度および面積から測定した値である。
主剤1~12の溶液状態について、東機産業社製のブルックフィールド型粘度計TVB-10M(以下、B型粘度計ともいう)を用いて25℃の溶液粘度を測定することで評価した。
<評価基準>
○(実用上優れる):500mPa・s未満
△(実用可能):500mPa・s以上1000mPa・s未満
×(実用不可能):1000mPa・s以上またはゲル化により粘度測定不可
ポットライフ性とは、結晶性酸変性ポリオレフィンに架橋剤または硬化剤を配合し、その配合直後または配合後一定時間経過後の該溶液の安定性を指す。ポットライフ性が良好な場合は、溶液の粘度上昇が少なく長期間保存が可能であることを指し、ポットライフ性が不良な場合は、溶液の粘度が上昇(増粘)し、ひどい場合にはゲル化現象を起こし、基材への塗布が困難となり、長期間保存が不可能であることを指す。
実施例1~69および比較例1~7で得られた接着剤組成物のポットライフ性を、25℃および40℃雰囲気で24時間貯蔵した後に、B型粘度計を用いて25℃の溶液粘度を測定することで評価した。評価結果を表2~5に示す。
<評価基準>
○(実用上優れる):500mPa・s未満
△(実用可能):500mPa・s以上1000mPa・s未満
×(実用不可能):1000mPa・s以上またはゲル化により粘度測定不可
金属基材にはアルミニウム箔(住軽アルミ箔社製、8079-0、厚さ40μm)をクロメート処理したものを使用し、ポリオレフィン樹脂基材には無延伸ポリプロピレンフィルム(東洋紡社製パイレン(登録商標)フィルムCT、厚さ40μm)(以下、CPPともいう。)を使用した。
実施例1~69および比較例1~7で得られた接着剤組成物を金属基材にバーコータを用いて乾燥後の接着剤層の膜厚が3μmになるように調整して塗布した。塗布面を温風乾燥機を用いて100℃雰囲気で1分間乾燥させ、膜厚3μmの接着剤層を得た。前記接着剤層表面にポリオレフィン樹脂基材を重ね合わせ、テスター産業社製の小型卓上テストラミネーター(SA-1010-S)を用いて80℃、0.3MPa、1m/分にて貼り合わせ、40℃、50%RHにて120時間養生することで積層体を得た。
前記積層体を100mm×15mm大きさに切断し、T型剥離試験により接着性の評価を行った。評価結果を表2、3に示す。
ASTM-D1876-61の試験法に準拠し、オリエンテックコーポレーション社製のテンシロンRTM-100を用いて、25℃環境下で、引張速度50mm/分における剥離強度を測定した。金属基材/ポリオレフィン樹脂基材間の剥離強度(N/cm)は5回の試験値の平均値とした。
☆(実用上特に優れる):8.0N/cm以上またはCPPが材破する(以下、単に「材破」ともいう。)材破とは、金属基材/CPPの界面で剥離が生じず、金属基材またはCPPが破壊されることをいう。
◎(実用上優れる):7.5N/cm以上8.0N/cm未満
○(実用可能):7.0N/cm以上7.5N/cm未満
×(実用不可能):7.0N/cm未満
アルミ箔とCPPの積層体の使用形態の1つであるリチウムイオン電池の包装材としての利用性を検討するため電解液試験による耐薬品性(以下、耐電解液性ともいう)の評価を行った。前記積層体を、100mm×15mm大きさに切断し、電解液[エチレンカーボネート/ジエチルカーボネート/ジメチルカーボネート=1/1/1(容積比)に6フッ化リン酸リチウムを添加したもの]に水を300ppm添加したものに85℃で3日間、または電解液に水を500ppm添加したものに85℃で5日間浸漬させた。その後、積層体を取り出しイオン交換水で洗浄、ペーパーワイパーで水を拭き取り、十分に水分を乾燥させ、100mm×15mm大きさに切断し、T型剥離試験により耐薬品性の評価を行った。
☆(実用上特に優れる):8.0N/cm以上または材破
◎(実用上優れる):7.5N/cm以上8.0N/cm未満
○(実用可能):7.0N/cm以上7.5N/cm未満
×(実用不可能):7.0N/cm未満
Claims (13)
- 酸価が5~50mgKOH/g-resinである結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、および有機溶剤(E)を含有し、さらに酸無水物モノマー(C)および窒素を2つ以上有する複素環式化合物(D)のいずれか一方を含有する接着剤組成物。
- 前記グリシジルアミン型エポキシ樹脂(B1)が、1分子中2個以上のグリシジル基を有するエポキシ樹脂である請求項1に記載の接着剤組成物。
- 前記グリシジルエーテル型エポキシ樹脂(B2)が、1分子中に2個以上のグリシジル基を有し、かつ窒素原子を含有しないエポキシ樹脂である請求項1~3のいずれかに記載の接着剤組成物。
- 前記酸無水物モノマー(C)が、1分子中に1個以上の酸無水物環を有し、酸価が100mgKOH/g以上の化合物である請求項1~4のいずれかに記載の接着剤組成物。
- 窒素を2つ以上有する複素環式化合物(D)が、窒素を2つ以上有する5員環芳香族複素環式化合物である請求項1~5のいずれかに記載の接着剤組成物。
- 結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、酸無水物モノマー(C)および有機溶剤(E)を含有し、結晶性酸変性ポリオレフィン(A)100質量部に対して、グリシジルアミン型エポキシ樹脂(B1)を0.01~20質量部、グリシジルエーテル型エポキシ樹脂(B2)を1~50質量部、酸無水物モノマー(C)を1~50質量部、有機溶剤(E)を80~1000質量部含有する請求項1~6のいずれかに記載の接着剤組成物。
- 結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、窒素を2つ以上有する複素環式化合物(D)および有機溶剤(E)を含有し、結晶性酸変性ポリオレフィン(A)100質量部に対して、グリシジルアミン型エポキシ樹脂(B1)を0.01~20質量部、グリシジルエーテル型エポキシ樹脂(B2)を1~50質量部、窒素を2つ以上有する複素環式化合物(D)を0.01~5質量部、有機溶剤(E)を80~1000質量部含有する請求項1~6のいずれかに記載の接着剤組成物。
- 結晶性酸変性ポリオレフィン(A)、グリシジルアミン型エポキシ樹脂(B1)、グリシジルエーテル型エポキシ樹脂(B2)、酸無水物モノマー(C)、窒素を2つ以上有する複素環式化合物(D)および有機溶剤(E)を含有し、結晶性酸変性ポリオレフィン(A)100質量部に対して、グリシジルアミン型エポキシ樹脂(B1)を0.01~20質量部、グリシジルエーテル型エポキシ樹脂(B2)を1~50質量部、酸無水物モノマー(C)を1~50質量部、窒素を2つ以上有する複素環式化合物(D)を0.01~5質量部、有機溶剤(E)を80~1000質量部含有する請求項1~6のいずれかに記載の接着剤組成物。
- 有機溶剤(E)が、溶剤(E1)と溶剤(E2)の混合液であって、溶剤(E1)が芳香族炭化水素、脂肪族炭化水素、脂環族炭化水素およびハロゲン化炭化水素からなる群より選択された1種以上の溶剤であり、溶剤(E2)がアルコール系溶媒、ケトン系溶媒、エステル系溶媒およびグリコールエーテル系溶剤からなる群より選択された1種以上の溶剤であり、溶剤(E1)/溶剤(E2)=50~97/50~3(質量比)である請求項1~9のいずれかに記載の接着剤組成物。
- ポリオレフィン樹脂基材と金属基材との接着に用いられる請求項1~10のいずれかに記載の接着剤組成物。
- 請求項1~11のいずれかに記載の接着剤組成物によって接着されたポリオレフィン樹脂基材と金属基材の積層体。
- 請求項12に記載の積層体を構成部材として含むリチウムイオン電池用包装材料。
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CN109476969B (zh) | 2021-11-02 |
TWI722223B (zh) | 2021-03-21 |
KR102301875B1 (ko) | 2021-09-15 |
CN109476969A (zh) | 2019-03-15 |
KR20190038844A (ko) | 2019-04-09 |
JP6278167B1 (ja) | 2018-02-14 |
JPWO2018030050A1 (ja) | 2018-08-09 |
TW201823406A (zh) | 2018-07-01 |
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