TWI775959B - Adhesive, laminate, battery member, and battery - Google Patents
Adhesive, laminate, battery member, and battery Download PDFInfo
- Publication number
- TWI775959B TWI775959B TW107134953A TW107134953A TWI775959B TW I775959 B TWI775959 B TW I775959B TW 107134953 A TW107134953 A TW 107134953A TW 107134953 A TW107134953 A TW 107134953A TW I775959 B TWI775959 B TW I775959B
- Authority
- TW
- Taiwan
- Prior art keywords
- resin
- adhesive
- acid group
- epoxy
- compound
- Prior art date
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 66
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 53
- 229920005989 resin Polymers 0.000 claims abstract description 84
- 239000011347 resin Substances 0.000 claims abstract description 84
- 239000002253 acid Substances 0.000 claims abstract description 74
- 239000004593 Epoxy Substances 0.000 claims abstract description 53
- 150000001875 compounds Chemical class 0.000 claims abstract description 48
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 28
- 125000003118 aryl group Chemical group 0.000 claims abstract description 22
- 229940126062 Compound A Drugs 0.000 claims abstract description 20
- NLDMNSXOCDLTTB-UHFFFAOYSA-N Heterophylliin A Natural products O1C2COC(=O)C3=CC(O)=C(O)C(O)=C3C3=C(O)C(O)=C(O)C=C3C(=O)OC2C(OC(=O)C=2C=C(O)C(O)=C(O)C=2)C(O)C1OC(=O)C1=CC(O)=C(O)C(O)=C1 NLDMNSXOCDLTTB-UHFFFAOYSA-N 0.000 claims abstract description 20
- 229920005749 polyurethane resin Polymers 0.000 claims abstract description 9
- 239000010410 layer Substances 0.000 claims description 30
- 229910052751 metal Inorganic materials 0.000 claims description 19
- 239000002184 metal Substances 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 claims description 17
- 238000006243 chemical reaction Methods 0.000 claims description 17
- 125000001424 substituent group Chemical group 0.000 claims description 11
- 238000003475 lamination Methods 0.000 claims description 9
- 125000002723 alicyclic group Chemical group 0.000 claims description 7
- 125000003700 epoxy group Chemical group 0.000 claims description 7
- 229920003023 plastic Polymers 0.000 claims description 7
- 239000004033 plastic Substances 0.000 claims description 7
- 239000012790 adhesive layer Substances 0.000 claims description 5
- 229910044991 metal oxide Inorganic materials 0.000 claims description 5
- 150000004706 metal oxides Chemical class 0.000 claims description 5
- 150000002739 metals Chemical class 0.000 claims description 5
- 125000001931 aliphatic group Chemical group 0.000 claims description 4
- 125000000217 alkyl group Chemical group 0.000 claims description 4
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 4
- 238000002156 mixing Methods 0.000 claims description 4
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 claims description 3
- 229920000058 polyacrylate Polymers 0.000 claims description 3
- 238000013329 compounding Methods 0.000 claims description 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 239000004925 Acrylic resin Substances 0.000 abstract description 9
- 125000002947 alkylene group Chemical group 0.000 abstract description 8
- 229910052799 carbon Inorganic materials 0.000 abstract description 4
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract description 3
- -1 β-carboxyethyl Chemical group 0.000 description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 36
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 36
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 27
- 239000003822 epoxy resin Substances 0.000 description 26
- 229920000647 polyepoxide Polymers 0.000 description 26
- 238000000034 method Methods 0.000 description 25
- 239000000243 solution Substances 0.000 description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 22
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
- 238000002360 preparation method Methods 0.000 description 17
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 16
- 239000002904 solvent Substances 0.000 description 15
- 239000002966 varnish Substances 0.000 description 15
- 238000001723 curing Methods 0.000 description 14
- 229920003986 novolac Polymers 0.000 description 14
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical group C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 13
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 12
- 239000000178 monomer Substances 0.000 description 12
- 239000003795 chemical substances by application Substances 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical group C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 10
- 150000002440 hydroxy compounds Chemical class 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- 239000000047 product Substances 0.000 description 10
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 9
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 9
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 9
- 239000004305 biphenyl Substances 0.000 description 9
- 239000003054 catalyst Substances 0.000 description 9
- 238000003756 stirring Methods 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 8
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 8
- 238000000576 coating method Methods 0.000 description 8
- 229920001577 copolymer Polymers 0.000 description 8
- 239000008151 electrolyte solution Substances 0.000 description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 229920000098 polyolefin Polymers 0.000 description 8
- 238000001816 cooling Methods 0.000 description 7
- 150000002989 phenols Chemical class 0.000 description 7
- 238000007789 sealing Methods 0.000 description 7
- 239000007787 solid Substances 0.000 description 7
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 6
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 6
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 6
- 238000012986 modification Methods 0.000 description 6
- 230000004048 modification Effects 0.000 description 6
- 239000011255 nonaqueous electrolyte Substances 0.000 description 6
- 239000005011 phenolic resin Substances 0.000 description 6
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 6
- 229910052782 aluminium Inorganic materials 0.000 description 5
- 235000010290 biphenyl Nutrition 0.000 description 5
- 238000007334 copolymerization reaction Methods 0.000 description 5
- 239000003792 electrolyte Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 5
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004743 Polypropylene Substances 0.000 description 4
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 4
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 4
- 238000002835 absorbance Methods 0.000 description 4
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 4
- 230000015572 biosynthetic process Effects 0.000 description 4
- 239000011248 coating agent Substances 0.000 description 4
- 229910052731 fluorine Inorganic materials 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 239000011229 interlayer Substances 0.000 description 4
- 150000002576 ketones Chemical class 0.000 description 4
- 238000005259 measurement Methods 0.000 description 4
- 125000001624 naphthyl group Chemical group 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 239000003495 polar organic solvent Substances 0.000 description 4
- 239000004848 polyfunctional curative Substances 0.000 description 4
- 235000013824 polyphenols Nutrition 0.000 description 4
- 229920001155 polypropylene Polymers 0.000 description 4
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 4
- 238000003786 synthesis reaction Methods 0.000 description 4
- 229920001187 thermosetting polymer Polymers 0.000 description 4
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 3
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 3
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 3
- 229930185605 Bisphenol Natural products 0.000 description 3
- RGSFGYAAUTVSQA-UHFFFAOYSA-N Cyclopentane Chemical compound C1CCCC1 RGSFGYAAUTVSQA-UHFFFAOYSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 239000004840 adhesive resin Substances 0.000 description 3
- 229920006223 adhesive resin Polymers 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 229910052786 argon Inorganic materials 0.000 description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 238000009820 dry lamination Methods 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- VXNZUUAINFGPBY-UHFFFAOYSA-N ethyl ethylene Natural products CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 3
- 239000011888 foil Substances 0.000 description 3
- 238000005227 gel permeation chromatography Methods 0.000 description 3
- DMEGYFMYUHOHGS-UHFFFAOYSA-N heptamethylene Natural products C1CCCCCC1 DMEGYFMYUHOHGS-UHFFFAOYSA-N 0.000 description 3
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- 238000006116 polymerization reaction Methods 0.000 description 3
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- 230000001681 protective effect Effects 0.000 description 3
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- 239000004711 α-olefin Substances 0.000 description 3
- LTVUCOSIZFEASK-MPXCPUAZSA-N (3ar,4s,7r,7as)-3a-methyl-3a,4,7,7a-tetrahydro-4,7-methano-2-benzofuran-1,3-dione Chemical compound C([C@H]1C=C2)[C@H]2[C@H]2[C@]1(C)C(=O)OC2=O LTVUCOSIZFEASK-MPXCPUAZSA-N 0.000 description 2
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- SSUJUUNLZQVZMO-UHFFFAOYSA-N 1,2,3,4,8,9,10,10a-octahydropyrimido[1,2-a]azepine Chemical compound C1CCC=CN2CCCNC21 SSUJUUNLZQVZMO-UHFFFAOYSA-N 0.000 description 2
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 2
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 description 2
- KJCVRFUGPWSIIH-UHFFFAOYSA-N 1-naphthol Chemical compound C1=CC=C2C(O)=CC=CC2=C1 KJCVRFUGPWSIIH-UHFFFAOYSA-N 0.000 description 2
- PTBDIHRZYDMNKB-UHFFFAOYSA-N 2,2-Bis(hydroxymethyl)propionic acid Chemical compound OCC(C)(CO)C(O)=O PTBDIHRZYDMNKB-UHFFFAOYSA-N 0.000 description 2
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- KNDQHSIWLOJIGP-UHFFFAOYSA-N 826-62-0 Chemical compound C1C2C3C(=O)OC(=O)C3C1C=C2 KNDQHSIWLOJIGP-UHFFFAOYSA-N 0.000 description 2
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- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 2
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- 238000005481 NMR spectroscopy Methods 0.000 description 2
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- 239000000806 elastomer Substances 0.000 description 2
- 238000005538 encapsulation Methods 0.000 description 2
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 125000001153 fluoro group Chemical group F* 0.000 description 2
- 125000003709 fluoroalkyl group Chemical group 0.000 description 2
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- AAAQKTZKLRYKHR-UHFFFAOYSA-N triphenylmethane Chemical compound C1=CC=CC=C1C(C=1C=CC=CC=1)C1=CC=CC=C1 AAAQKTZKLRYKHR-UHFFFAOYSA-N 0.000 description 1
- RYFMWSXOAZQYPI-UHFFFAOYSA-K trisodium phosphate Chemical compound [Na+].[Na+].[Na+].[O-]P([O-])([O-])=O RYFMWSXOAZQYPI-UHFFFAOYSA-K 0.000 description 1
- 229920006337 unsaturated polyester resin Polymers 0.000 description 1
- 238000007740 vapor deposition Methods 0.000 description 1
- PXXNTAGJWPJAGM-UHFFFAOYSA-N vertaline Natural products C1C2C=3C=C(OC)C(OC)=CC=3OC(C=C3)=CC=C3CCC(=O)OC1CC1N2CCCC1 PXXNTAGJWPJAGM-UHFFFAOYSA-N 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
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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
- 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
- H01M50/102—Primary casings; Jackets or wrappings characterised by their shape or physical structure
- H01M50/105—Pouches or flexible bags
-
- 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
- B32B15/092—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 epoxy resins
-
- 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
-
- 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
- C09J133/00—Adhesives based on homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by only one carboxyl radical, or of salts, anhydrides, esters, amides, imides, or nitriles thereof; Adhesives based on derivatives of such polymers
-
- 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
-
- 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
-
- 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
- C09J201/00—Adhesives based on unspecified macromolecular compounds
- C09J201/02—Adhesives based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
-
- 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
- H01M50/183—Sealing members
- H01M50/19—Sealing members characterised by the material
- H01M50/193—Organic material
-
- 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
- H01M50/183—Sealing members
- H01M50/19—Sealing members characterised by the material
- H01M50/198—Sealing members characterised by the material characterised by physical properties, e.g. adhesiveness or hardness
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Electrochemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Sealing Battery Cases Or Jackets (AREA)
- Primary Cells (AREA)
Abstract
本發明提供一種接著劑,其特徵在於包含:含酸基樹脂;及環氧化合物A,所述環氧化合物A含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基。另外,提供含酸基樹脂為含酸基聚丙烯酸酯樹脂、含酸基聚胺基甲酸酯樹脂、及/或含酸基聚烯烴樹脂的所述接著劑。另外,本發明提供一種使用該接著劑的積層體、含有該積層體的電池用構件、及包括該電池用構件的電池。The present invention provides an adhesive, which is characterized by comprising: an acid group-containing resin; and an epoxy compound A, wherein the epoxy compound A contains an aromatic ring, an alkylene chain with a carbon number of 4-10, and two or more epoxy compounds base. In addition, the adhesive agent in which the acid group-containing resin is an acid group-containing polyacrylate resin, an acid group-containing polyurethane resin, and/or an acid group-containing polyolefin resin is provided. In addition, the present invention provides a laminate using the adhesive, a battery member containing the laminate, and a battery including the battery member.
Description
本發明是有關於一種接著劑、積層體、電池用構件及電池。The present invention relates to an adhesive, a laminate, a battery member, and a battery.
以鋰離子電池等二次電池為代表的電池具有正極、負極及於該些之間封入電解液等的構成。另外,作為用於封入導線的封入袋,使用將鋁箔等金屬箔或金屬蒸鍍層與塑膠貼合的積層體,所述導線用於將正極與負極的電取出至外部。A battery typified by a secondary battery such as a lithium ion battery has a positive electrode, a negative electrode, and a structure in which an electrolyte solution or the like is sealed between these. In addition, as an encapsulation bag for enclosing a lead wire for taking out electricity from the positive electrode and the negative electrode to the outside, a laminate in which a metal foil such as aluminum foil or a metal vapor deposition layer is bonded to a plastic is used.
例如,專利文獻1中提出有一種封入袋,其中積層體的最內層使用馬來酸改質聚烯烴樹脂,且由同樣的馬來酸改質聚烯烴樹脂構成熱封部,藉此而提升密封可靠性。馬來酸改質聚烯烴樹脂因與金屬的接著性及熱封性優異,故一般被用作接著性樹脂。但是,若用作如上所述的電池的密封膜,則於高溫下的積層後即刻顯示優異的接著力,但耐電解液性低,隨時間經過而產生層間剝離,無法用作密封膜。For example, Patent Document 1 proposes an encapsulation bag in which maleic acid-modified polyolefin resin is used for the innermost layer of the laminate, and the heat-sealing portion is formed of the same maleic acid-modified polyolefin resin, thereby improving the Seal reliability. Maleic acid-modified polyolefin resins are generally used as adhesive resins because they are excellent in adhesion to metals and heat-sealability. However, when used as a sealing film for such a battery, it exhibits excellent adhesion immediately after lamination at high temperature, but has low electrolyte resistance, and interlayer peeling occurs over time, so it cannot be used as a sealing film.
專利文獻2中記載有電池電解液密封膜用積層體或電池電極部保護膜用積層體,其包括:金屬層、形成於金屬層的表面的表面處理層、及形成於表面處理層上的包含羧酸基或其衍生物改質的聚烯烴的接著性樹脂層。Patent Document 2 describes a laminate for a battery electrolyte sealing film or a laminate for a battery electrode portion protective film, which includes a metal layer, a surface-treated layer formed on the surface of the metal layer, and a metal layer formed on the surface-treated layer. An adhesive resin layer of a polyolefin modified with a carboxylic acid group or a derivative thereof.
專利文獻3中記載有一種接著性樹脂組成物,其包含:具有選自由酸酐基、羧基及羧酸金屬鹽所組成的群組中的至少一種官能基的聚烯烴系樹脂;及具有兩個以上的環氧基,且分子量為3000以下的環氧化植物油,環氧化植物油成分相對於聚烯烴成分100質量份的調配量為0.01質量份~5質量份。Patent Document 3 describes an adhesive resin composition comprising: a polyolefin-based resin having at least one functional group selected from the group consisting of an acid anhydride group, a carboxyl group, and a metal carboxylate; and two or more In the epoxidized vegetable oil with a molecular weight of 3000 or less, the compounding amount of the epoxidized vegetable oil component relative to 100 parts by mass of the polyolefin component is 0.01 to 5 parts by mass.
專利文獻4中記載有一種二次電池電極用黏合劑用樹脂組成物,其特徵在於含有酸改質聚烯烴樹脂及聚胺基甲酸酯樹脂,且相對於聚烯烴樹脂100質量份,聚胺基甲酸酯樹脂為0.5質量份~100質量份。 [現有技術文獻] [專利文獻]Patent Document 4 describes a resin composition for a binder for secondary battery electrodes, which is characterized in that it contains an acid-modified polyolefin resin and a polyurethane resin, and a polyamine is added to 100 parts by mass of the polyolefin resin. The carboxylate resin is 0.5 parts by mass to 100 parts by mass. [Prior Art Document] [Patent Document]
[專利文獻1]日本專利特開平09-283101號公報 [專利文獻2]WO2007/017043號公報 [專利文獻3]日本專利特開平08-193148號公報 [專利文獻4]日本專利特開2010-277959號公報[Patent Document 1] Japanese Patent Laid-Open No. 09-283101 [Patent Document 2] WO2007/017043 No. [Patent Document 3] Japanese Patent Laid-Open No. 08-193148 [Patent Document 4] Japanese Patent Laid-Open No. 2010-277959 Bulletin No.
[發明所欲解決之課題] 本發明的課題在於提供一種接著強度優異,而且耐電解液性亦優異的接著劑。另外,提供一種使用該接著劑的積層體、含有該積層體的電池用構件、及包括該電池用構件的電池。 [解決課題之手段]THE PROBLEM TO BE SOLVED BY THE INVENTION The subject of this invention is to provide the adhesive agent which is excellent in adhesive strength and also excellent in electrolyte solution resistance. In addition, a laminate using the adhesive, a battery member containing the laminate, and a battery including the battery member are provided. [Means of Solving Problems]
本發明者等人進行努力研究,結果發現含有含酸基樹脂及具有特定結構的環氧樹脂的接著劑可解決所述課題。 [發明的效果]As a result of intensive research conducted by the present inventors, it was found that an adhesive containing an acid group-containing resin and an epoxy resin having a specific structure can solve the above-mentioned problems. [Effect of invention]
即,本發明提供一種接著劑,其特徵在於包含:含酸基樹脂;及環氧化合物A,所述環氧化合物A含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基。That is, the present invention provides an adhesive characterized by comprising: an acid group-containing resin; and an epoxy compound A, wherein the epoxy compound A contains an aromatic ring, an alkylene chain having 4 to 10 carbon atoms, and two or more epoxy group.
進而,提供一種積層體,其特徵在於在中間層具有該接著劑層。Furthermore, there is provided a laminated body characterized by having the adhesive layer in the intermediate layer.
進而,提供一種電池用構件,其包括該積層體。Furthermore, there is provided a battery member including the laminate.
<含酸基樹脂> 本發明的接著劑的特徵在於包含:含酸基樹脂;及環氧化合物A,所述環氧化合物A含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基。<Acid group-containing resin> The adhesive of the present invention is characterized by comprising: an acid group-containing resin; and an epoxy compound A containing an aromatic ring, an alkylene chain having 4 to 10 carbon atoms, and two the above epoxy groups.
所謂含酸基樹脂是指樹脂中具有酸基的樹脂。作為酸基,可列舉羧基、羧酸酐基、磺酸基、磷酸基等。作為含酸基樹脂,若酸價為1 mgKOH/g~200 mgKOH/g,則與金屬的密接性提升,因而較佳。特佳為5 mgKOH/g~165 mgKOH/g。若為200 mgKOH/g以下,則柔軟性優異因而接著強度變高,若為1 mgKOH/g以上,則耐熱性良好。The so-called acid group-containing resin refers to a resin having an acid group in the resin. As an acid group, a carboxyl group, a carboxylic acid anhydride group, a sulfonic acid group, a phosphoric acid group, etc. are mentioned. As the acid group-containing resin, when the acid value is 1 mgKOH/g to 200 mgKOH/g, the adhesiveness with the metal is improved, and thus it is preferable. Particularly preferred is 5 mgKOH/g to 165 mgKOH/g. When it is 200 mgKOH/g or less, since flexibility is excellent, the adhesive strength becomes high, and when it is 1 mgKOH/g or more, heat resistance is favorable.
(酸價測定方法) 所謂酸價,是指用於中和試樣1 g中存在的含酸量而所需的氫氧化鉀的毫克(mg)數。具體而言,可藉由下述方法進行測定,即,將所秤量的試樣溶於以體積比計為甲苯/甲醇=70/30的溶媒中,預先滴加數滴1%酚酞醇溶液,並於其中滴加0.1 mol/L的氫氧化鉀醇溶液,確認變色點,且可利用下述計算式而求出。(Method for Measuring Acid Value) The acid value refers to the number of milligrams (mg) of potassium hydroxide required to neutralize the acid content present in 1 g of the sample. Specifically, the measurement can be carried out by dissolving the weighed sample in a solvent whose volume ratio is toluene/methanol=70/30, and adding several drops of a 1% phenolphthalein alcohol solution in advance, A 0.1 mol/L potassium hydroxide alcohol solution was added dropwise thereto to confirm the discoloration point, which can be determined by the following formula.
酸價測定方法-1 酸價(mgKOH/g)=(V×F×5.61)/S V:0.1 mol/L氫氧化鉀醇溶液的使用量(mL) F:0.1 mol/L氫氧化鉀醇溶液的滴定度 S:試樣的採集量(g) 5.61:0.1 mol/L氫氧化鉀醇溶液1 mL中的氫氧化鉀相當量(mg)Acid value determination method-1 Acid value (mgKOH/g) = (V×F×5.61)/S V: 0.1 mol/L potassium hydroxide alcohol solution usage (mL) F: 0.1 mol/L potassium hydroxide alcohol solution The titer of S: the amount of sample collected (g) 5.61: the equivalent amount of potassium hydroxide in 1 mL of 0.1 mol/L potassium hydroxide alcohol solution (mg)
於試樣為樹脂溶液的情況下,可利用下述計算式來求出樹脂酸價(mgKOH/g)。When the sample is a resin solution, the resin acid value (mgKOH/g) can be determined by the following formula.
樹脂酸價(mgKOH/g)=樹脂溶液的酸價(mgKOH/g)/NV(%)×100 NV:不揮發成分(%)Resin acid value (mgKOH/g) = acid value of resin solution (mgKOH/g)/NV (%) × 100 NV: non-volatile content (%)
另外,於試樣對有機溶媒的溶解性低、析出等而難以測定的情況下,亦可藉由以下方法來測定酸價。In addition, when the solubility of a sample to an organic solvent is low, precipitation, etc. make it difficult to measure, the acid value can also be measured by the following method.
酸價測定方法-2 所謂酸價(mgKOH/g-樹脂),是指利用傅立葉轉換紅外光譜儀(Fourier transform-infrared spectrometer,FT-IR)(日本分光公司製造,FT-IR4200),使用馬來酸酐的根據由氯仿溶液所製成的校準曲線而獲得的係數(f)、馬來酸酐改質聚烯烴溶液中馬來酸酐的無水環的伸縮峰值(1780 cm-1 )的吸光度(I)及馬來酸的羰基的伸縮峰值(1720 cm-1 )的吸光度(II),藉由下述式而算出的值。 酸價(mgKOH/g-樹脂)=[(吸光度(I)×(f)×2×氫氧化鉀的分子量×1000(mg)+吸光度(II)×(f)×氫氧化鉀的分子量×1000(mg))/馬來酸酐的分子量] 馬來酸酐的分子量:98.06,氫氧化鉀的分子量:56.11Acid value measurement method-2 The acid value (mgKOH/g-resin) refers to the use of a Fourier transform-infrared spectrometer (FT-IR) (manufactured by JASCO Corporation, FT-IR4200) using maleic anhydride The coefficient (f) obtained from the calibration curve made from the chloroform solution, the absorbance (I) of the stretching peak (1780 cm -1 ) of the anhydrous ring of maleic anhydride in the maleic anhydride-modified polyolefin solution, and the The absorbance (II) of the stretch peak (1720 cm −1 ) of the carbonyl group of leucic acid was calculated by the following formula. Acid value (mgKOH/g-resin) = [(absorbance (I) × (f) × 2 × molecular weight of potassium hydroxide × 1000 (mg) + absorbance (II) × (f) × molecular weight of potassium hydroxide × 1000 (mg))/Molecular weight of maleic anhydride] Molecular weight of maleic anhydride: 98.06, molecular weight of potassium hydroxide: 56.11
作為含酸基樹脂,樹脂骨架並無特別限定,可列舉含酸基聚丙烯酸酯樹脂、含酸基聚胺基甲酸酯樹脂及/或含酸基聚烯烴樹脂等作為較佳樹脂。The resin skeleton is not particularly limited as the acid group-containing resin, and preferred resins include acid group-containing polyacrylate resin, acid group-containing polyurethane resin, and/or acid group-containing polyolefin resin.
(含酸基聚丙烯酸酯樹脂) 作為所述含酸基聚丙烯酸酯樹脂,例如可列舉具有(甲基)丙烯醯基及羧基的聚合性單量體的共聚物。具體而言,作為具有(甲基)丙烯醯基及羧基的聚合性單量體,可列舉:(甲基)丙烯酸;β-羧基乙基(甲基)丙烯酸酯、2-丙烯醯氧基乙基丁二酸酯、2-丙烯醯氧基乙基鄰苯二甲酸酯、2-丙烯醯氧基乙基六氫鄰苯二甲酸酯及該些的內酯改質物等具有酯鍵的不飽和單羧酸;馬來酸等。(Acid group-containing polyacrylate resin) Examples of the acid group-containing polyacrylate resin include copolymers of polymerizable monomers having a (meth)acryloyl group and a carboxyl group. Specifically, as a polymerizable monomer having a (meth)acryloyl group and a carboxyl group, (meth)acrylic acid; β-carboxyethyl (meth)acrylate, 2-acryloyloxyethyl Ethyl succinate, 2-acryloyloxyethyl phthalate, 2-acryloyloxyethyl hexahydrophthalate, and lactone modified products of these, etc. having an ester bond Unsaturated monocarboxylic acid; maleic acid, etc.
作為視需要與具有(甲基)丙烯醯基及羧基的單量體聚合的其他聚合性不飽和單量體,例如可列舉以下聚合性單量體等。As another polymerizable unsaturated monomer polymerized with the monomer which has a (meth)acryloyl group and a carboxyl group as needed, the following polymerizable monomer etc. are mentioned, for example.
可列舉:(1)(甲基)丙烯酸甲酯、(甲基)丙烯酸乙酯、(甲基)丙烯酸丙酯、(甲基)丙烯酸正丁酯、(甲基)丙烯酸第三丁酯、(甲基)丙烯酸己酯、(甲基)丙烯酸庚酯、(甲基)丙烯酸辛酯、(甲基)丙烯酸壬酯、(甲基)丙烯酸癸酯、(甲基)丙烯酸十二烷基酯、(甲基)丙烯酸十四烷基酯、(甲基)丙烯酸十六烷基酯、(甲基)丙烯酸硬脂酯、(甲基)丙烯酸十八烷基酯、(甲基)丙烯酸二十二烷基酯等具有碳數1~22的烷基的(甲基)丙烯酸酯類;(1) methyl (meth)acrylate, ethyl (meth)acrylate, propyl (meth)acrylate, n-butyl (meth)acrylate, tert-butyl (meth)acrylate, ( Hexyl (meth)acrylate, heptyl (meth)acrylate, octyl (meth)acrylate, nonyl (meth)acrylate, decyl (meth)acrylate, dodecyl (meth)acrylate, tetradecyl (meth)acrylate, cetyl (meth)acrylate, stearyl (meth)acrylate, octadecyl (meth)acrylate, behenyl (meth)acrylate (Meth)acrylates having an alkyl group having 1 to 22 carbon atoms, such as alkyl esters;
(2)(甲基)丙烯酸環己酯、(甲基)丙烯酸異冰片酯、(甲基)丙烯酸二環戊基酯、(甲基)丙烯酸二環戊烯氧基乙酯等具有脂式烷基的(甲基)丙烯酸酯類;(2) Cyclohexyl (meth)acrylate, isobornyl (meth)acrylate, dicyclopentyl (meth)acrylate, dicyclopentenyloxyethyl (meth)acrylate, etc. based (meth)acrylates;
(3)(甲基)丙烯酸苯甲醯氧基乙酯、(甲基)丙烯酸苄酯、(甲基)丙烯酸苯基乙酯、(甲基)丙烯酸苯氧基乙酯、(甲基)丙烯酸苯氧基二乙二醇、(甲基)丙烯酸2-羥基-3-苯氧基丙酯等具有芳香環的(甲基)丙烯酸酯類;(3) Benzyloxyethyl (meth)acrylate, benzyl (meth)acrylate, phenylethyl (meth)acrylate, phenoxyethyl (meth)acrylate, (meth)acrylic acid (meth)acrylates with aromatic rings such as phenoxydiethylene glycol and 2-hydroxy-3-phenoxypropyl (meth)acrylate;
(4)(甲基)丙烯酸羥基乙酯;(甲基)丙烯酸羥基丙酯、(甲基)丙烯酸羥基丁酯、甘油(甲基)丙烯酸酯;內酯改質(甲基)丙烯酸羥基乙酯、(甲基)丙烯酸聚乙二醇、(甲基)丙烯酸聚丙二醇等具有聚伸烷基二醇基的(甲基)丙烯酸酯等具有羥基烷基的丙烯酸酯類;(4) Hydroxyethyl (meth)acrylate; hydroxypropyl (meth)acrylate, hydroxybutyl (meth)acrylate, glycerol (meth)acrylate; lactone-modified hydroxyethyl (meth)acrylate , (meth)acrylic acid polyethylene glycol, (meth)acrylic acid polypropylene glycol and other (meth)acrylic acid esters with polyalkylene glycol groups and other acrylates with hydroxyalkyl groups;
(5)富馬酸二甲酯、富馬酸二乙酯、富馬酸二丁酯、衣康酸二甲酯、衣康酸二丁酯、富馬酸甲基乙酯、富馬酸甲基丁酯、衣康酸甲基乙酯等不飽和二羧酸酯類;(5) Dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl itaconate, dibutyl itaconate, methyl ethyl fumarate, methyl fumarate Unsaturated dicarboxylates such as methyl butyl ester and methyl ethyl itaconic acid;
(6)苯乙烯、α-甲基苯乙烯、氯苯乙烯等苯乙烯衍生物類;(6) Styrene derivatives such as styrene, α-methylstyrene, and chlorostyrene;
(7)丁二烯、異戊二烯、戊間二烯(piperylene)、二甲基丁二烯等二烯系化合物類;(7) Diene compounds such as butadiene, isoprene, piperylene and dimethyl butadiene;
(8)氯乙烯、溴乙烯等鹵化乙烯基或鹵化亞乙烯類;(8) Vinyl halide or vinylidene halide such as vinyl chloride and vinyl bromide;
(9)甲基乙烯基酮、丁基乙烯基酮等不飽和酮類;(9) Unsaturated ketones such as methyl vinyl ketone and butyl vinyl ketone;
(10)乙酸乙烯酯、丁酸乙烯酯等乙烯酯類;(10) Vinyl esters such as vinyl acetate and vinyl butyrate;
(11)甲基乙烯基醚、丁基乙烯基醚等乙烯基醚類;(11) Vinyl ethers such as methyl vinyl ether and butyl vinyl ether;
(12)丙烯腈、甲基丙烯腈、氰化亞乙烯等氰化乙烯基類;(12) Vinyl cyanide such as acrylonitrile, methacrylonitrile, vinylidene cyanide;
(13)丙烯醯胺或其醇酸取代醯胺類;(13) Acrylamide or its alkyd-substituted amides;
(14)N-苯基馬來醯亞胺、N-環己基馬來醯亞胺等N-取代馬來醯亞胺類;(14) N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide;
(15)氟乙烯、偏二氟乙烯、三氟乙烯、氯三氟乙烯、溴三氟乙烯、五氟丙烯或六氟丙烯般的含氟α-烯烴類;或者三氟甲基三氟乙烯醚、五氟乙基三氟乙烯醚或七氟丙基三氟乙烯醚般的(全)氟烷基的碳數為1至18的(全)氟烷基·全氟乙烯醚類;2,2,2-三氟乙基(甲基)丙烯酸酯、2,2,3,3-四氟丙基(甲基)丙烯酸酯、1H,1H,5H-八氟戊基(甲基)丙烯酸酯、1H,1H,2H,2H-十七氟癸基(甲基)丙烯酸酯或全氟乙基氧基乙基(甲基)丙烯酸酯般的(全)氟烷基的碳數為1至18的(全)氟烷基(甲基)丙烯酸酯類等含氟乙烯性不飽和單量體類;(15) Fluorine-containing α-olefins such as vinyl fluoride, vinylidene fluoride, trifluoroethylene, chlorotrifluoroethylene, bromotrifluoroethylene, pentafluoropropylene or hexafluoropropylene; or trifluoromethyl trifluoroethylene ether , Pentafluoroethyl trifluorovinyl ether or heptafluoropropyl trifluorovinyl ether (per)fluoroalkyl carbon number of 1 to 18 (per)fluoroalkyl perfluorovinyl ethers; 2,2 , 2-trifluoroethyl (meth)acrylate, 2,2,3,3-tetrafluoropropyl (meth)acrylate, 1H,1H,5H-octafluoropentyl (meth)acrylate, 1H, 1H, 2H, 2H-heptadecafluorodecyl (meth)acrylate or perfluoroethyloxyethyl (meth)acrylate such as (per)fluoroalkyl with a carbon number of 1 to 18 (per)fluoroalkyl (meth)acrylates and other fluorine-containing ethylenically unsaturated monomers;
(16)γ-甲基丙烯醯氧基丙基三甲氧基矽烷等含矽烷基的(甲基)丙烯酸酯類;(16) Silyl-containing (meth)acrylates such as γ-methacryloyloxypropyltrimethoxysilane;
(17)N,N-二甲基胺基乙基(甲基)丙烯酸酯、N,N-二乙基胺基乙基(甲基)丙烯酸酯或N,N-二乙基胺基丙基(甲基)丙烯酸酯等N,N-二烷基胺基烷基(甲基)丙烯酸酯等。(17) N,N-dimethylaminoethyl (meth)acrylate, N,N-diethylaminoethyl (meth)acrylate or N,N-diethylaminopropyl N,N-dialkylaminoalkyl (meth)acrylates such as (meth)acrylates and the like.
製備該些含酸基聚丙烯酸酯時使用的其他聚合性不飽和單量體可單獨使用,亦可併用兩種以上。Other polymerizable unsaturated monomers used in the preparation of these acid group-containing polyacrylates may be used alone or in combination of two or more.
所述含酸基聚丙烯酸酯若使用公知慣用的方法進行聚合(共聚)即可獲得,其共聚形態並無特別限制。可於觸媒(聚合起始劑)的存在下藉由加成聚合而製造,可為無規共聚物、嵌段共聚物、接枝共聚物等任一種。另外共聚方法亦可使用塊狀聚合法、溶液聚合法、懸浮聚合法、乳化聚合法等公知的聚合方法。The acid group-containing polyacrylate can be obtained by performing polymerization (copolymerization) by a known and conventional method, and the copolymerization form thereof is not particularly limited. It can be produced by addition polymerization in the presence of a catalyst (polymerization initiator), and can be any of random copolymers, block copolymers, and graft copolymers. In addition, a known polymerization method, such as a block polymerization method, a solution polymerization method, a suspension polymerization method, and an emulsion polymerization method, can also be used for the copolymerization method.
(含酸基聚胺基甲酸酯樹脂) 作為所述含酸基聚胺基甲酸酯樹脂,可列舉使下述式(1)所表示的化合物B、與下述式(2)所表示的化合物C反應而獲得的樹脂。(Acid group-containing polyurethane resin) Examples of the acid group-containing polyurethane resin include compound B represented by the following formula (1) and compound B represented by the following formula (2). The resin obtained by the reaction of compound C.
[化1]…(1)[hua 1] …(1)
(式(1)中,X1 表示芳香環或脂環結構,n1及n2分別獨立地表示0~3的整數)(In formula (1), X 1 represents an aromatic ring or an alicyclic structure, and n1 and n2 each independently represent an integer of 0 to 3)
[化2]…(2)[hua 2] …(2)
(式(2)中,R1 表示氫原子或碳數1~3的烴基或羰基,m1~m3分別獨立地表示0~3的整數)(In formula (2), R 1 represents a hydrogen atom, a hydrocarbon group having 1 to 3 carbon atoms, or a carbonyl group, and m1 to m3 each independently represent an integer of 0 to 3)
<化合物B> 化合物B為所述式(1)所表示的具有異氰酸酯基的化合物。化合物B中,X1 表示芳香環或脂環結構。<Compound B> Compound B is a compound having an isocyanate group represented by the above formula (1). In compound B, X 1 represents an aromatic ring or an alicyclic structure.
作為芳香環結構,較佳為碳數6~18的芳香環,可列舉苯環、萘環、菲環、蒽環等。作為所述芳香環,可經至少一個氟原子取代,作為經至少一個氟原子取代的芳香環,可列舉全氟苯基等。 另外,作為脂環結構,較佳為碳數3~20的脂環,可為單環亦可為稠環。作為單環,環烷烴有環丙烷、環丁烷、環戊烷、環己烷、環庚烷、環辛烷、環壬烷、環癸烷、環十一烷、環十二烷等。另外,單環的環烯烴可列舉環丙烯、環丁烯、環戊烯、環己烯、環庚烯、環辛烯等。作為稠環,有雙環十一烷或十氫萘、降冰片烯或降冰片二烯等。 另外多環式化合物可列舉立方烷、籃烷(basketane)、房烷(housane)等。 另外,亦可為芳香環與脂環組合而成的環結構。The aromatic ring structure is preferably an aromatic ring having 6 to 18 carbon atoms, and examples thereof include a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring. The aromatic ring may be substituted with at least one fluorine atom, and examples of the aromatic ring substituted with at least one fluorine atom include a perfluorophenyl group and the like. In addition, as an alicyclic structure, an alicyclic ring having 3 to 20 carbon atoms is preferable, and a single ring may be used or a condensed ring may be used. Examples of the monocyclic cycloalkane include cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, cyclododecane, and the like. Moreover, cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, etc. are mentioned as a monocyclic cycloolefin. As the condensed ring, there are bicycloundecane, decalin, norbornene, norbornadiene, and the like. In addition, a cubic alkane, a basketane (basketane), a house alkane (housane), etc. are mentioned as a polycyclic compound. In addition, it may be a ring structure in which an aromatic ring and an alicyclic ring are combined.
化合物B中,X1 較佳為苯環或萘環。 另外,n1及n2較佳為分別獨立地為0~1。In compound B, X 1 is preferably a benzene ring or a naphthalene ring. Moreover, it is preferable that n1 and n2 are each independently 0-1.
作為化合物B的更佳的結構,可列舉以下結構。As a more preferable structure of compound B, the following structures are mentioned.
[化3]…(3)[hua 3] …(3)
[化4]…(4)[hua 4] …(4)
[化5]…(5)[hua 5] …(5)
[化6]…(6)[hua 6] …(6)
[化7]…(7)[hua 7] …(7)
<化合物C> 化合物C為所述式(2)所表示的具有羧基的二醇化合物。<Compound C> Compound C is a diol compound having a carboxyl group represented by the above formula (2).
關於化合物C,較佳為m3為0的化合物,進而佳為R1 為碳數1~3的烴基的情況。The compound C is preferably a compound in which m3 is 0, and more preferably a case where R1 is a hydrocarbon group having 1 to 3 carbon atoms.
作為化合物C的更佳的結構,可列舉二羥甲基丙酸、及二羥甲基丁酸。As a more preferable structure of compound C, dimethylol propionic acid and dimethylol butyric acid are mentioned.
(含酸基聚烯烴樹脂) 作為所述含酸基聚烯烴樹脂的骨架,具體而言例如可列舉:高密度聚乙烯(HDPE)、低密度聚乙烯(LDPE)、線狀低密度聚乙烯樹脂等聚乙烯、聚丙烯、聚異丁烯、聚(1-丁烯)、聚4-甲基戊烯、聚乙烯基環己烷、聚苯乙烯、聚(對甲基苯乙烯)、聚(α-甲基苯乙烯)、乙烯·丙烯嵌段共聚物、乙烯·丙烯無規共聚物、乙烯·丁烯-1-共聚物、乙烯·4-甲基-1-戊烯共聚物、乙烯·己烯共聚物等α-烯烴共聚物、乙烯·乙酸乙烯酯共聚物、乙烯·丙烯酸共聚物、乙烯·甲基丙烯酸甲酯共聚物、乙烯·乙酸乙烯酯·甲基丙烯酸甲酯共聚物、離子聚合物樹脂等。進而,亦可使用將該些聚烯烴氯化而得的氯化聚烯烴。(Acid group-containing polyolefin resin) Specific examples of the skeleton of the acid group-containing polyolefin resin include high-density polyethylene (HDPE), low-density polyethylene (LDPE), and linear low-density polyethylene resins. Polyethylene, polypropylene, polyisobutylene, poly(1-butene), poly4-methylpentene, polyvinylcyclohexane, polystyrene, poly(p-methylstyrene), poly(α- Methylstyrene), ethylene-propylene block copolymer, ethylene-propylene random copolymer, ethylene-butene-1-copolymer, ethylene-4-methyl-1-pentene copolymer, ethylene-hexene α-olefin copolymers such as copolymers, ethylene-vinyl acetate copolymers, ethylene-acrylic acid copolymers, ethylene-methyl methacrylate copolymers, ethylene-vinyl acetate-methyl methacrylate copolymers, ionic polymers resin, etc. Furthermore, chlorinated polyolefins obtained by chlorinating these polyolefins can also be used.
為了於樹脂中導入酸基,只要使用公知慣用的方法即可。可將含酸基單體聚合而合成樹脂,亦可之後於樹脂中加成酸基。較佳為利用不飽和羧酸或其衍生物將聚烯烴改質來進行合成的方法。作為該改質方法,可利用接枝改質或共聚合化。In order to introduce an acid group into a resin, a well-known and usual method should just be used. The acid group-containing monomer can be polymerized to synthesize the resin, or the acid group can be added to the resin later. A method in which a polyolefin is modified and synthesized with an unsaturated carboxylic acid or a derivative thereof is preferred. As this modification method, graft modification or copolymerization can be utilized.
較佳的酸改質聚烯烴樹脂是使至少一個能夠聚合的乙烯性不飽和羧酸或其衍生物與改質前的聚烯烴樹脂進行接枝改質或共聚合化而成的接枝改質聚烯烴。作為改質前的聚烯烴樹脂,可列舉以上所述的聚烯烴樹脂,其中較佳為丙烯的均聚物、丙烯與α-烯烴的共聚物等。該些可單獨使用一種,亦可組合使用兩種以上。The preferred acid-modified polyolefin resin is a graft-modified product obtained by graft-modifying or copolymerizing at least one polymerizable ethylenically unsaturated carboxylic acid or its derivative with the polyolefin resin before modification. polyolefin. Examples of the polyolefin resin before modification include the above-mentioned polyolefin resins, and among them, a homopolymer of propylene, a copolymer of propylene and an α-olefin, and the like are preferred. These may be used individually by 1 type, and may be used in combination of 2 or more types.
作為與改質前的聚烯烴樹脂進行接枝改質或共聚合化的乙烯性不飽和羧酸或其衍生物,例如可列舉:丙烯酸、甲基丙烯酸、馬來酸、衣康酸、檸康酸、中康酸、馬來酸酐、4-甲基環己-4-烯-1,2-二羧酸酐、雙環[2.2.2]辛-5-烯-2,3-二羧酸酐、1,2,3,4,5,8,9,10-八氫萘-2,3-二羧酸酐、2-辛-1,3-二酮螺[4.4]酮-7-烯、雙環[2.2.1]庚-5-烯-2,3-二羧酸酐、馬來海松酸(maleopimaric acid)、四氫鄰苯二甲酸酐、甲基-雙環[2.2.1]庚-5-烯-2,3-二羧酸酐、甲基-降冰片-5-烯-2,3-二羧酸酐、降冰片-5-烯-2,3-二羧酸酐等。較佳為使用馬來酸酐。該些可單獨使用,或者一併使用兩種以上。Examples of ethylenically unsaturated carboxylic acids or derivatives thereof to be graft-modified or copolymerized with the polyolefin resin before modification include acrylic acid, methacrylic acid, maleic acid, itaconic acid, and citraconic acid. acid, mesaconic acid, maleic anhydride, 4-methylcyclohex-4-ene-1,2-dicarboxylic acid anhydride, bicyclo[2.2.2]oct-5-ene-2,3-dicarboxylic acid anhydride, 1 ,2,3,4,5,8,9,10-octahydronaphthalene-2,3-dicarboxylic anhydride, 2-oct-1,3-dionespiro[4.4]one-7-ene, bicyclo[2.2 .1] Hept-5-ene-2,3-dicarboxylic anhydride, maleopimaric acid, tetrahydrophthalic anhydride, methyl-bicyclo[2.2.1]hept-5-ene-2 , 3-dicarboxylic acid anhydride, methyl-norbornan-5-ene-2,3-dicarboxylic acid anhydride, norbornan-5-ene-2,3-dicarboxylic acid anhydride, etc. Preferably maleic anhydride is used. These can be used alone or in combination of two or more.
為了使選自乙烯性不飽和羧酸或其衍生物的接枝單體與改質前的聚烯烴樹脂接枝,可採用各種方法。例如可列舉:將聚烯烴樹脂熔融,於其中添加接枝單體而進行接枝反應的方法;將聚烯烴樹脂溶解於溶媒中而製成溶液,於其中添加接枝單體而進行接枝反應的方法;將溶解於有機溶劑中的聚烯烴樹脂與所述不飽和羧酸等混合,以所述聚烯烴樹脂的軟化溫度或融點以上的溫度加熱而以熔融狀態同時進行自由基聚合及脫氫反應的方法等。為了於任一情況下均使所述接枝單體效率良好地進行接枝共聚,較佳為於自由基起始劑的存在下實施接枝反應。接枝反應通常於60℃~350℃的條件下進行。相對於改質前的聚烯烴樹脂100重量份,自由基起始劑的使用比例通常為0.001重量份~1重量份的範圍。In order to graft the graft monomer selected from ethylenically unsaturated carboxylic acids or derivatives thereof to the polyolefin resin before modification, various methods can be employed. For example, a method of melting a polyolefin resin, adding a graft monomer to it, and carrying out a graft reaction; dissolving a polyolefin resin in a solvent to prepare a solution, adding a graft monomer to the solution, and carrying out a graft reaction method; the polyolefin resin dissolved in the organic solvent is mixed with the unsaturated carboxylic acid, etc., and heated at the softening temperature of the polyolefin resin or the temperature above the melting point to carry out radical polymerization and dehydration simultaneously in a molten state. The method of hydrogen reaction, etc. In any case, in order to efficiently carry out the graft copolymerization of the graft monomer, it is preferable to carry out the graft reaction in the presence of a radical initiator. The grafting reaction is usually carried out under the conditions of 60°C to 350°C. The use ratio of the radical initiator is usually in the range of 0.001 part by weight to 1 part by weight with respect to 100 parts by weight of the polyolefin resin before modification.
作為該些酸改質聚烯烴樹脂,例如可列舉:馬來酸酐改質聚丙烯、乙烯-(甲基)丙烯酸共聚物、乙烯-丙烯酸酯-馬來酸酐三元共聚物、或乙烯-甲基丙烯酸酯-馬來酸酐三元共聚物。具體而言,市售有三菱化學(股)製造的「莫迪奇(MODIC)」、三井化學(股)製造的「阿德莫(ADMER)」、「尤尼斯托(UNISTOLE)」、東洋紡(股)製造的「東洋塔克(TOYO-TAC)」、三洋化成(股)製造的「尤邁克斯(UMEX)」、日本聚乙烯(股)製造的「萊克斯珀(REXPEARL)EAA」、「萊克斯珀(REXPEARL)ET」、陶氏化學(股)製造的「普力馬克(PRIMACOR)」、三井杜邦寶理化學製造的「紐克萊爾(NUCREL)」、阿科瑪(ARKEMA)製造的「邦定(BONDINE)」。Examples of these acid-modified polyolefin resins include maleic anhydride-modified polypropylene, ethylene-(meth)acrylic acid copolymers, ethylene-acrylate-maleic anhydride terpolymers, or ethylene-methyl Acrylate-maleic anhydride terpolymer. Specifically, “MODIC” manufactured by Mitsubishi Chemical Co., Ltd., “ADMER” manufactured by Mitsui Chemicals Co., Ltd., “UNISTOLE”, Toyobo ( "TOYO-TAC" made by Sanyo Chemical Co., Ltd., "UMEX" made by Sanyo Chemical Co., Ltd., "REXPEARL EAA" made by Japan Polyethylene Co., Ltd., " Rexper (REXPEARL) ET", "PRIMACOR" manufactured by Dow Chemical Co., Ltd., "NUCREL" manufactured by Mitsui DuPont Polychemicals, "Bonan" manufactured by Arkema (ARKEMA) BONDINE".
(其他含酸基樹脂) 作為其他含酸基樹脂,含酸彈性體例如可列舉旭化成股份有限公司製造的塔弗泰(Tuftec)M系列或日本科騰聚合物(Kraton polumer Japan)股份有限公司製造的科騰(Kraton)FG系列等。(Other acid group-containing resins) As other acid group-containing resins, acid-containing elastomers include, for example, Tuftec M series manufactured by Asahi Kasei Co., Ltd. or Kraton Polumer Japan Co., Ltd. The Kraton FG series, etc.
<含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基的環氧化合物A> 本發明的接著劑亦包含含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基的環氧化合物A。<Epoxy compound A containing an aromatic ring, an alkylene chain having 4 to 10 carbon atoms, and two or more epoxy groups> The adhesive of the present invention also includes an aromatic ring and an alkylene chain having 4 to 10 carbon atoms. And the epoxy compound A of two or more epoxy groups.
作為芳香環,可列舉:可具有取代基的苯環、可具有取代基的萘環、可具有取代基的雙酚結構、可具有取代基的聯苯結構等,例如可列舉:於o-、m-、p-位上分別具有鍵結部位的伸苯基、4,4'-伸聯苯基、2,2',6,6'-四甲基-4,4'-聯苯基、亞甲基二伸苯基、2,2-丙烷-二苯基、1,6-萘基、2,7-萘基、1,4-萘基、1,5-萘基、2,3-萘基、及下述結構式Examples of the aromatic ring include a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, a bisphenol structure which may have a substituent, a biphenyl structure which may have a substituent, and the like, for example, o-, phenylene, 4,4'-biphenylene, 2,2',6,6'-tetramethyl-4,4'-biphenylene, Methylenediphenylene, 2,2-propane-diphenyl, 1,6-naphthyl, 2,7-naphthyl, 1,4-naphthyl, 1,5-naphthyl, 2,3-naphthyl Naphthyl, and the following structural formula
[化8] [hua 8]
所表示的基等,就所獲得的硬化物的柔軟性與強韌性的平衡優異的觀點而言,較佳為亞甲基二伸苯基、2,2-丙烷-二苯基。The groups and the like represented are preferably methylenediphenylene and 2,2-propane-diphenyl from the viewpoint of excellent balance between flexibility and toughness of the obtained cured product.
作為環氧化合物A,具體而言較佳為由以下式(8)所表示的環氧化合物(A1)。Specifically as the epoxy compound A, an epoxy compound (A1) represented by the following formula (8) is preferable.
[化9]…(8)[Chemical 9] …(8)
(式中,Ar1 、Ar2 、Ar3 、Ar4 為可相同亦可不同的可具有取代基的芳香環,X1 、X2 為脂肪族烴基,R1 、R2 、R3 為可相同亦可不同的氫原子或碳數1~4的烷基,p、q、r以重複數的平均值計p為0.5~5.0,q為0.5~5.0,r為0.05~0.5)(In the formula, Ar 1 , Ar 2 , Ar 3 and Ar 4 are the same or different aromatic rings which may have substituents, X 1 and X 2 are aliphatic hydrocarbon groups, and R 1 , R 2 , and R 3 are optionally substituted. The same or different hydrogen atoms or alkyl groups having 1 to 4 carbon atoms, p, q and r are calculated as the average of the repeating numbers, p is 0.5 to 5.0, q is 0.5 to 5.0, and r is 0.05 to 0.5)
關於環氧化合物(A1),就所獲得的硬化物的交聯密度適當且可兼具柔軟強韌性與耐熱性的觀點而言,較佳為環氧當量為150 g/eq~900 g/eq者。另外,就作業性良好且硬化物的柔軟性及密接性優異的觀點而言,較佳為所述環氧化合物(A1)的25℃下的黏度為2,000 Pa·s~20,000 Pa·s者,特佳為2,000 Pa·s~15,000 Pa·s。Regarding the epoxy compound (A1), the epoxy equivalent is preferably 150 g/eq to 900 g/eq from the viewpoint that the obtained cured product has an appropriate crosslinking density and can have both flexibility, toughness, and heat resistance. By. In addition, from the viewpoint of good workability and excellent flexibility and adhesion of the cured product, it is preferable that the epoxy compound (A1) has a viscosity at 25° C. of 2,000 Pa·s to 20,000 Pa·s, Particularly preferred is 2,000 Pa·s to 15,000 Pa·s.
所述式(1)中的X1 、X2 中至少一者為碳數4~10的直鏈狀伸烷基鏈。其原因在於,若碳數過短,則有損柔軟性,接著力降低,若過長,則反應性下降,接著力降低。較佳為X1 、X2 的兩者為碳數4~10的直鏈狀伸烷基鏈的情況。另外,於重視所獲得的硬化物的耐熱性或硬度、耐濕性的情況下,作為所述式(1)中的X1 、X2 ,亦可使用含有脂環結構者。At least one of X 1 and X 2 in the formula (1) is a linear alkylene chain having 4 to 10 carbon atoms. The reason for this is that when the number of carbon atoms is too short, the flexibility is impaired and the adhesive force is lowered, and when the carbon number is too long, the reactivity is lowered and the adhesive force is lowered. Preferably, both of X 1 and X 2 are a linear alkylene chain having 4 to 10 carbon atoms. Moreover, when the heat resistance, hardness, and moisture resistance of the hardened|cured material obtained are important, those containing an alicyclic structure can also be used as X1 and X2 in the said formula ( 1 ).
作為所述式(1)中的Ar1 、Ar2 、Ar3 、Ar4 ,可使用所述芳香環。即,可列舉:可具有取代基的苯環、可具有取代基的萘環、可具有取代基的雙酚結構、可具有取代基的聯苯結構等,例如可列舉:於o-、m-、p-位上分別具有鍵結部位的伸苯基、4,4'-伸聯苯基、2,2',6,6'-四甲基-4,4'-聯苯基、亞甲基二伸苯基、2,2-丙烷-二苯基、1,6-萘基、2,7-萘基、1,4-萘基、1,5-萘基、2,3-萘基、及下述結構式As Ar 1 , Ar 2 , Ar 3 , and Ar 4 in the formula (1), the aromatic ring can be used. That is, a benzene ring which may have a substituent, a naphthalene ring which may have a substituent, a bisphenol structure which may have a substituent, a biphenyl structure which may have a substituent, etc. are mentioned, for example, o-, m- , phenylene, 4,4'-biphenylene, 2,2',6,6'-tetramethyl-4,4'-biphenylene, methylene Diphenylene, 2,2-propane-diphenyl, 1,6-naphthyl, 2,7-naphthyl, 1,4-naphthyl, 1,5-naphthyl, 2,3-naphthyl , and the following structural formula
[化10] [Chemical 10]
所表示的基等,就所獲得的硬化物的柔軟性與強韌性的平衡優異的觀點而言,較佳為亞甲基二伸苯基、2,2-丙烷-二苯基。The groups and the like represented are preferably methylenediphenylene and 2,2-propane-diphenyl from the viewpoint of excellent balance between flexibility and toughness of the obtained cured product.
作為環氧化合物(A1),可列舉以下(A1-1)至(A1-9)的結構作為較佳結構。As the epoxy compound (A1), the following structures (A1-1) to (A1-9) can be mentioned as preferable structures.
[化11] [Chemical 11]
[化12] [Chemical 12]
[化13] [Chemical 13]
所述各結構式中,G為縮水甘油基,p、q、r為重複數的平均值且p為0.5~5.0,q為0.5~5.0,r為0.05~0.5。另外,各芳香環上亦可具有碳數1~4的烷基、鹵素原子等作為取代基。該些中,就所獲得的硬化物的物性平衡優異的觀點而言,最佳為使用所述結構式(A1-3)、(A1-4)所表示者。In each of the above structural formulas, G is a glycidyl group, p, q, and r are average values of repeating numbers, p is 0.5 to 5.0, q is 0.5 to 5.0, and r is 0.05 to 0.5. In addition, each aromatic ring may have an alkyl group having 1 to 4 carbon atoms, a halogen atom, or the like as a substituent. Among these, it is preferable to use those represented by the above-mentioned structural formulae (A1-3) and (A1-4) from the viewpoint of excellent physical property balance of the obtained cured product.
環氧化合物(A1)的製造方法並無特別限定,就原料獲得或反應容易的觀點而言,較佳為使用以下方法:以莫耳比(c1)/(c2)為1/1.1~1/5.0的範圍使脂肪族系二羥基化合物的縮水甘油醚或脂肪族系酸化合物的二縮水甘油酯(c1)與芳香族系二羥基化合物(c2)反應,並使所獲得的羥基化合物進而與表氯醇類(c3)反應的方法。The production method of the epoxy compound (A1) is not particularly limited, but from the viewpoint of easy availability of raw materials and easy reaction, the following method is preferably used: The molar ratio (c1)/(c2) is 1/1.1 to 1/ In the range of 5.0, the glycidyl ether of the aliphatic dihydroxy compound or the diglycidyl ester (c1) of the aliphatic acid compound is reacted with the aromatic dihydroxy compound (c2), and the obtained hydroxy compound is further reacted with the table. Method for the reaction of chlorohydrins (c3).
<接著劑> 本發明的接著劑包含:含酸基樹脂;及環氧化合物A,所述環氧化合物A含有芳香環及碳數4-10的伸烷基鏈以及兩個以上的環氧基。 本發明的接著劑由於接著強度、特別是初始接著力優異,作為積層體的層壓物柔軟,因此能夠適宜用作層壓用接著劑。另外,本發明的接著劑由於與金屬層良好地接著,因此作為金屬用接著劑亦適宜。另外,硬化後的本接著劑的耐電解液性亦優異,因此作為電池用接著劑亦適宜。<Adhesive> The adhesive of the present invention includes: an acid group-containing resin; and an epoxy compound A containing an aromatic ring, an alkylene chain having 4 to 10 carbon atoms, and two or more epoxy groups . The adhesive of the present invention can be suitably used as an adhesive for lamination because it is excellent in adhesive strength, especially initial adhesive force, and since the laminate as a laminate is soft. Moreover, since the adhesive agent of this invention adheres well to a metal layer, it is suitable also as an adhesive agent for metals. In addition, since the present adhesive after curing is also excellent in electrolyte solution resistance, it is also suitable as an adhesive for batteries.
<其他環氧化合物> 本發明的接著劑中可包含環氧化合物A以外的環氧化合物。例如可列舉:雙酚A型環氧樹脂、雙酚F型環氧樹脂、雙酚S型環氧樹脂、雙酚AD型環氧樹脂、間苯二酚型環氧樹脂、二羥基萘型環氧樹脂、聯苯型環氧樹脂、四甲基聯苯型環氧樹脂、具有蒽、聯苯、雙酚A、雙酚F、雙酚S的結構的三官能以上的環氧化合物、固體雙酚A型環氧樹脂、苯酚酚醛清漆型環氧樹脂、甲酚酚醛清漆型環氧樹脂、三苯基甲烷型環氧樹脂、四苯基乙烷型環氧樹脂、二環戊二烯-苯酚加成反應型環氧樹脂、苯酚芳烷基型環氧樹脂、萘酚酚醛清漆型環氧樹脂、萘酚芳烷基型環氧樹脂、萘酚-苯酚共縮合酚醛清漆型環氧樹脂、萘酚-甲酚共縮合酚醛清漆型環氧樹脂、芳香族烴甲醛樹脂改質苯酚樹脂型環氧樹脂、聯苯改質酚醛清漆型環氧樹脂等。 <Other epoxy compounds> The adhesive agent of this invention may contain epoxy compounds other than epoxy compound A. For example, bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD type epoxy resin, resorcinol type epoxy resin, dihydroxynaphthalene type ring Oxygen resin, biphenyl type epoxy resin, tetramethyl biphenyl type epoxy resin, trifunctional or higher epoxy compound having the structure of anthracene, biphenyl, bisphenol A, bisphenol F, bisphenol S, solid bisphenol Phenol A type epoxy resin, phenol novolak type epoxy resin, cresol novolac type epoxy resin, triphenylmethane type epoxy resin, tetraphenylethane type epoxy resin, dicyclopentadiene-phenol Addition reaction type epoxy resin, phenol aralkyl type epoxy resin, naphthol novolak type epoxy resin, naphthol aralkyl type epoxy resin, naphthol-phenol co-condensation novolak type epoxy resin, naphthalene Phenol-cresol co-condensation novolak type epoxy resin, aromatic hydrocarbon formaldehyde resin modified phenol resin type epoxy resin, biphenyl modified novolak type epoxy resin, etc.
作為環氧化合物,可單獨使用一種環氧化合物,亦可組合使用多種環氧化合物。 As the epoxy compound, one kind of epoxy compound may be used alone, or a plurality of kinds of epoxy compounds may be used in combination.
本發明中,環氧化合物A與其他環氧化合物的比率以莫耳比計較佳為100:0~5:95。作為層壓用接著劑,就柔軟性的方面而言特佳為100:0~10:90。 In the present invention, the ratio of the epoxy compound A to the other epoxy compounds is preferably 100:0 to 5:95 in terms of molar ratio. The adhesive agent for lamination is particularly preferably 100:0 to 10:90 in terms of flexibility.
<調配比> <mixing ratio>
為了製備接著劑,較佳為以所述含酸基樹脂所含有的酸基、與包含環氧化合物A的環氧化合物所含有的環氧基的當量比(環氧/酸價)成為0.01~10的方式進行調配。更佳為以成為0.1~5的方式進行調配。 In order to prepare an adhesive, it is preferable that the equivalent ratio (epoxy/acid value) of the acid group contained in the acid group-containing resin to the epoxy group contained in the epoxy compound containing the epoxy compound A (epoxy/acid value) be 0.01 to 0.01 10 ways to deploy. More preferably, it mixes so that it may become 0.1-5.
其原因在於,若當量比為0.01以上,則耐熱性優異,若為10以下,則接著力優異。 The reason for this is that when the equivalence ratio is 0.01 or more, the heat resistance is excellent, and when it is 10 or less, the adhesive force is excellent.
<其他樹脂> <Other resins>
另外,本發明的接著劑亦可於無損發明的效果的範圍內含有含酸基樹脂與環氧化合物以外的樹脂。作為樹脂,可使用熱硬化性樹脂或熱塑性樹脂。 Moreover, the adhesive agent of this invention may contain resin other than an acid group-containing resin and an epoxy compound in the range which does not impair the effect of this invention. As the resin, a thermosetting resin or a thermoplastic resin can be used.
所謂熱硬化性樹脂,是指具有當藉由加熱或放射線或觸媒等手段使其硬化時實質上不溶且可變化為不融性的特性的樹脂。作為其具體例,可列舉:苯酚樹脂、脲樹脂、三聚氰胺樹脂、苯并胍胺樹脂、醇酸樹脂、不飽和聚酯樹脂、乙烯酯樹脂、對苯二甲酸二烯丙酯樹脂、矽酮樹脂、胺基甲酸酯樹脂、呋喃樹脂、酮樹脂、二甲苯樹脂、熱硬化性聚醯胺樹脂、苯并噁嗪樹脂、活性酯樹脂、苯胺樹脂、氰酸酯基酯樹脂、苯乙烯·馬來酸酐(styrene maleic anhydride,SMA)樹脂等。該些熱硬化性樹脂可使用一種或併用兩種以上。The term "thermosetting resin" refers to a resin having a property of being substantially insoluble and capable of being changed into infusibility when hardened by means such as heating, radiation, or a catalyst. Specific examples thereof include phenol resins, urea resins, melamine resins, benzoguanamine resins, alkyd resins, unsaturated polyester resins, vinyl ester resins, diallyl terephthalate resins, and silicone resins. , urethane resin, furan resin, ketone resin, xylene resin, thermosetting polyamide resin, benzoxazine resin, active ester resin, aniline resin, cyanate ester resin, styrene-polyester resin To the acid anhydride (styrene maleic anhydride, SMA) resin and so on. These thermosetting resins may be used alone or in combination of two or more.
所謂熱塑性樹脂,是指藉由加熱而可熔融成形的樹脂。作為其具體例,可列舉:聚乙烯樹脂、聚丙烯樹脂、聚苯乙烯樹脂、橡膠改質聚苯乙烯樹脂、丙烯腈-丁二烯-苯乙烯(Acrylonitrile Butadiene Styrene,ABS)樹脂、丙烯腈-苯乙烯(Acrylonitrile Styrene,AS)樹脂、聚甲基丙烯酸甲酯樹脂、丙烯酸樹脂、聚氯乙烯樹脂、聚偏二氯乙烯樹脂、聚對苯二甲酸乙二酯樹脂、乙烯乙烯基醇樹脂、乙酸纖維素樹脂、離子聚合物樹脂、聚丙烯腈樹脂、聚醯胺樹脂、聚縮醛樹脂、聚對苯二甲酸丁二酯樹脂、聚乳酸樹脂、聚苯醚樹脂、改質聚苯醚樹脂、聚碳酸酯樹脂、聚碸樹脂、聚苯硫醚樹脂、聚醚醯亞胺樹脂、聚醚碸樹脂、聚丙烯酸酯樹脂、熱塑性聚醯亞胺樹脂、聚醯胺醯亞胺樹脂、聚醚醚酮樹脂、聚酮樹脂、液晶聚酯樹脂、氟樹脂、間規聚苯乙烯樹脂、環狀聚烯烴樹脂等。該些熱塑化性樹脂可使用一種或併用兩種以上。The thermoplastic resin refers to a resin that can be melt-molded by heating. Specific examples thereof include polyethylene resin, polypropylene resin, polystyrene resin, rubber-modified polystyrene resin, acrylonitrile-butadiene-styrene (ABS) resin, acrylonitrile- Styrene (Acrylonitrile Styrene, AS) resin, polymethyl methacrylate resin, acrylic resin, polyvinyl chloride resin, polyvinylidene chloride resin, polyethylene terephthalate resin, ethylene vinyl alcohol resin, acetic acid Cellulose resin, ionomer resin, polyacrylonitrile resin, polyamide resin, polyacetal resin, polybutylene terephthalate resin, polylactic acid resin, polyphenylene ether resin, modified polyphenylene ether resin, Polycarbonate resin, polyimide resin, polyphenylene sulfide resin, polyetherimide resin, polyetherimide resin, polyacrylate resin, thermoplastic polyimide resin, polyimide resin, polyether ether Ketone resin, polyketone resin, liquid crystal polyester resin, fluororesin, syndiotactic polystyrene resin, cyclic polyolefin resin, etc. These thermoplastic resins may be used alone or in combination of two or more.
<硬化觸媒> 本發明的接著劑亦可使用硬化觸媒。 作為硬化觸媒,可利用一般的環氧硬化劑,具體而言可併用胺系硬化劑、醯胺系硬化劑、酸酐系硬化劑、酚系硬化劑、活性酯系硬化劑、含羧基硬化劑、硫醇系硬化劑等各種硬化劑。<Curing catalyst> A curing catalyst may be used for the adhesive of the present invention. As the curing catalyst, a general epoxy curing agent can be used, and specifically, an amine-based curing agent, an amide-based curing agent, an acid anhydride-based curing agent, a phenol-based curing agent, an active ester-based curing agent, and a carboxyl group-containing curing agent can be used in combination , mercaptan-based hardeners and other hardeners.
具體而言,作為胺系硬化劑,可列舉二胺基二苯基甲烷、二胺基二苯基乙烷、二胺基二苯基醚、二胺基二苯基碸、鄰苯二胺、間苯二胺、對苯二胺、間二甲苯二胺、對二甲苯二胺、二乙基甲苯二胺、二乙三胺、三乙四胺、異佛爾酮二胺、咪唑、BF3-胺錯合物、胍衍生物、胍胺衍生物等。Specifically, as the amine-based curing agent, diaminodiphenylmethane, diaminodiphenylethane, diaminodiphenyl ether, diaminodiphenylene, o-phenylenediamine, m-phenylenediamine, p-phenylenediamine, m-xylylenediamine, p-xylylenediamine, diethyltoluenediamine, diethylenetriamine, triethylenetetramine, isophoronediamine, imidazole, BF3- Amine complexes, guanidine derivatives, guanamine derivatives, etc.
作為醯胺系硬化劑,可列舉二氰二醯胺、由次亞麻油酸的二聚體與乙二胺所合成的聚醯胺樹脂等。 作為酸酐系硬化劑,可列舉:鄰苯二甲酸酐、偏苯三甲酸酐、均苯四甲酸酐、馬來酸酐、四氫鄰苯二甲酸酐、甲基四氫鄰苯二甲酸酐、甲基納迪克酸酐(methyl nadic anhydride)、六氫鄰苯二甲酸酐、甲基六氫鄰苯二甲酸酐等。 作為酚系硬化劑,可列舉:雙酚A、雙酚F、雙酚S、間苯二酚、鄰苯二酚、對苯二酚、茀雙酚、4,4'-雙酚、4,4',4''-三羥基三苯基甲烷、萘二酚、1,1,2,2-四(4-羥基苯基)乙烷、杯芳烴(calixarene)、以苯酚酚醛清漆樹脂、甲酚酚醛清漆樹脂、芳香族烴甲醛樹脂改質苯酚樹脂、二環戊二烯苯酚加成型樹脂、苯酚芳烷基樹脂(新酚樹脂)、間苯二酚酚醛清漆樹脂為代表的由多元羥基化合物與甲醛所合成的多元苯酚酚醛清漆樹脂、萘酚芳烷基樹脂、三羥甲基甲烷樹脂、四羥苯基乙烷樹脂、萘酚酚醛清漆樹脂、萘酚-苯酚共縮合酚醛清漆樹脂、萘酚-甲酚共縮合酚醛清漆樹脂、聯苯改質苯酚樹脂(以雙亞甲基連結酚核的多元苯酚化合物)、聯苯改質萘酚樹脂(以雙亞甲基連結酚核的多元萘酚化合物)、胺基三嗪改質苯酚樹脂(以三聚氰胺、苯并胍胺等連結酚核的多元苯酚化合物)或含烷氧基芳香環改質酚醛清漆樹脂(以甲醛連結酚核及含烷氧基芳香環的多元苯酚化合物)等多元苯酚化合物。 該些硬化觸媒可單獨使用亦可併用兩種以上。As the amide-based curing agent, dicyandiamide, a polyamide resin synthesized from a dimer of hypolinoleic acid and ethylenediamine, and the like can be mentioned. As an acid anhydride type hardener, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, maleic anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methyl Nadic anhydride (methyl nadic anhydride), hexahydrophthalic anhydride, methyl hexahydrophthalic anhydride, etc. Examples of the phenol-based curing agent include bisphenol A, bisphenol F, bisphenol S, resorcinol, catechol, hydroquinone, bisphenol, 4,4'-bisphenol, 4,4'-bisphenol, 4',4''-trihydroxytriphenylmethane, naphthalenediol, 1,1,2,2-tetrakis(4-hydroxyphenyl)ethane, calixarene, phenol novolac resin, methyl alcohol Phenol novolac resins, aromatic hydrocarbon formaldehyde resin modified phenol resins, dicyclopentadiene phenol addition resins, phenol aralkyl resins (new phenol resins), resorcinol novolac resins represented by polyvalent hydroxyl compounds Polyhydric phenol novolac resin synthesized with formaldehyde, naphthol aralkyl resin, trimethylolmethane resin, tetrahydroxyphenylethane resin, naphthol novolac resin, naphthol-phenol co-condensation novolac resin, naphthalene Phenol-cresol co-condensed novolac resin, biphenyl-modified phenol resin (polyphenol compound with bis-methylene connecting phenol core), biphenyl-modified naphthol resin (poly-naphthalene with bis-methylene connecting phenol core) phenolic compounds), aminotriazine modified phenol resins (polyvalent phenolic compounds linked with phenolic cores such as melamine and benzoguanamine) or modified novolac resins containing alkoxy aromatic rings (with formaldehyde linked to phenolic cores and alkane-containing phenolic compounds) oxy-aromatic ring polyphenol compounds) and other polyhydric phenol compounds. These hardening catalysts may be used alone or in combination of two or more.
進而,硬化促進劑可單獨使用,或者亦可與所述硬化觸媒併用。作為硬化促進劑,可使用促進環氧化合物的硬化反應的各種化合物,例如可列舉磷系化合物、三級胺化合物、咪唑化合物、有機酸金屬鹽、路易斯酸、胺錯合物鹽等。其中,較佳為使用咪唑化合物、磷系化合物、三級胺化合物,特別是就硬化性、耐熱性、電氣特性、耐濕可靠性等優異的觀點而言,磷系化合物較佳為三苯基膦,三級胺較佳為1,8-二氮雜雙環-[5.4.0]-十一烯(1,8-Diazabicyclo-[5.4.0]-undecene,DBU),咪唑化合物較佳為2-乙基-4-甲基咪唑。Furthermore, a hardening accelerator may be used alone or in combination with the above-mentioned hardening catalyst. As a hardening accelerator, various compounds which accelerate|stimulate the hardening reaction of an epoxy compound can be used, For example, a phosphorus compound, a tertiary amine compound, an imidazole compound, an organic acid metal salt, a Lewis acid, an amine complex salt, etc. are mentioned. Among them, an imidazole compound, a phosphorus-based compound, and a tertiary amine compound are preferably used, and the phosphorus-based compound is preferably triphenyl from the viewpoint of being excellent in curability, heat resistance, electrical properties, moisture resistance reliability, and the like. Phosphine, the tertiary amine is preferably 1,8-diazabicyclo-[5.4.0]-undecene (1,8-Diazabicyclo-[5.4.0]-undecene, DBU), and the imidazole compound is preferably 2 -Ethyl-4-methylimidazole.
硬化觸媒及硬化促進劑可調配亦可不調配,於調配的情況下,相對於接著劑中的總固體成分合計100重量份,較佳為0.001重量份~10重量份。特佳為0.005重量份~5重量份。The hardening catalyst and the hardening accelerator may be mixed without mixing, and in the case of mixing, they are preferably 0.001 to 10 parts by weight relative to 100 parts by weight of the total solid content in the adhesive. It is especially preferable that it is 0.005 weight part - 5 weight part.
<溶劑> 接著劑可根據使用用途而含有溶劑。作為溶劑,可列舉有機溶劑,例如可列舉:甲基乙基酮、丙酮、乙酸乙酯、乙酸丁酯、甲苯、二甲基甲醯胺、丙烯腈、甲基異丁基酮、甲醇、乙醇、甲氧基丙醇、環己酮、甲基賽珞蘇、乙基二甘醇乙酸酯、丙二醇單甲醚乙酸酯、甲基環己酮等。溶劑的種類及使用量只要根據使用用途而適當選擇即可。<Solvent> The adhesive agent may contain a solvent according to the application. Examples of the solvent include organic solvents, for example, methyl ethyl ketone, acetone, ethyl acetate, butyl acetate, toluene, dimethylformamide, acrylonitrile, methyl isobutyl ketone, methanol, and ethanol. , Methoxypropanol, Cyclohexanone, Methyl Siloso, Ethyl Diethylene Glycol Acetate, Propylene Glycol Monomethyl Ether Acetate, Methyl Cyclohexanone, etc. The kind and usage amount of the solvent may be appropriately selected according to the intended use.
特別是於作為乾式層壓用接著劑的情況下,較佳為使用烴系溶劑、酮系溶劑、酯系溶劑或醇系溶媒。In particular, when used as an adhesive for dry lamination, it is preferable to use a hydrocarbon-based solvent, a ketone-based solvent, an ester-based solvent, or an alcohol-based solvent.
於使用溶劑的情況下,可於調配含酸基樹脂及環氧化合物A後調配,亦可將含酸基樹脂或環氧化合物A預先溶解於溶劑中而用作清漆。In the case of using a solvent, it can be prepared after preparing the acid group-containing resin and the epoxy compound A, or the acid group-containing resin or the epoxy compound A can be dissolved in the solvent in advance and used as a varnish.
於使用溶劑的情況下,於接著劑總量100重量份中,溶劑成分較佳為50重量份~90重量份。更佳為以成為60重量份~85重量份的方式調配。In the case of using a solvent, the solvent component is preferably 50 to 90 parts by weight in 100 parts by weight of the total amount of the adhesive. It is more preferable to mix|blend so that it may become 60 weight part - 85 weight part.
接著劑可於無損本發明的效果的範圍內含有各種添加劑。作為添加劑,例如可例示觸媒、界面活性劑、穩定劑(抗氧化劑、熱穩定劑、紫外線吸收劑等)、防蝕劑、反應性彈性體、偶合劑、塑化劑、抗靜電劑、潤滑劑、防黏連劑、著色劑、填料、成核劑、具有氧捕捉功能的化合物、黏著賦予劑等。該些添加劑的含量可於不損及本發明的接著劑的功能的範圍內適當調整而使用。The adhesive agent may contain various additives within a range that does not impair the effects of the present invention. Examples of additives include catalysts, surfactants, stabilizers (antioxidants, heat stabilizers, ultraviolet absorbers, etc.), corrosion inhibitors, reactive elastomers, coupling agents, plasticizers, antistatic agents, and lubricants. , anti-blocking agent, colorant, filler, nucleating agent, compound with oxygen capture function, adhesion imparting agent, etc. The content of these additives can be appropriately adjusted and used within a range that does not impair the function of the adhesive of the present invention.
<積層體> 本發明的積層體的特徵在於在中間層具有本發明的接著劑層。 積層體的上層及下層並無特別限定,只要根據用途而選擇即可。例如,可列舉聚乙烯、聚丙烯、聚對苯二甲酸乙二酯等塑膠;鐵、鋁、銅、銀、鈦等金屬或金屬氧化物、木材、紙、該些的複合材料等。<Laminated body> The layered body of the present invention is characterized by having the adhesive layer of the present invention in the intermediate layer. The upper layer and the lower layer of the laminate are not particularly limited, and may be selected according to the application. Examples include plastics such as polyethylene, polypropylene, and polyethylene terephthalate; metals such as iron, aluminum, copper, silver, and titanium, or metal oxides; wood, paper, and composite materials thereof.
其中,本發明的接著劑對金屬或金屬氧化物層的接著性非常良好,因此作為金屬或金屬氧化物用接著劑而言良好。特佳為用於鋁。Among them, since the adhesive of the present invention has very good adhesiveness to the metal or metal oxide layer, it is good as an adhesive for metals or metal oxides. Especially preferred for aluminum.
積層體的上層及下層的形狀並無特別限定,可為平板、片狀、或者三維形狀整面或一部分具有曲率者等根據目的的任意形狀。另外,基材的硬度、厚度等亦無限制。The shape of the upper layer and the lower layer of the layered body is not particularly limited, and may be any shape according to the purpose, such as a flat plate, a sheet, or a three-dimensional shape having a curvature on the entire surface or a part thereof. In addition, the hardness, thickness, etc. of the base material are also not limited.
關於本發明的積層體,接著劑層的塗敷方法並無特別限定,可列舉:噴霧法、旋塗法、浸漬法、輥塗法、刮塗法、刮刀輥法、刮刀片法、簾塗法、狹縫塗佈法、網版印刷法、噴墨法等。Regarding the layered product of the present invention, the coating method of the adhesive layer is not particularly limited, and examples thereof include spray method, spin coating method, dipping method, roll coating method, blade coating method, doctor roll method, doctor blade method, and curtain coating method. method, slit coating method, screen printing method, inkjet method, etc.
<層壓> 本發明的接著劑由於接著強度非常高,因此能夠適宜用於層壓用途。於作為層壓用接著劑的情況下,乾燥塗佈重量較佳為0.5 g/m2 ~20.0 g/m2 的範圍內。若為0.5 g/m2 以上,則連續均勻塗佈性良好,若為20.0 g/m2 以下,則塗佈後的溶劑脫離性良好,因此作業性與脫溶劑性的平衡優異。<Lamination> The adhesive of the present invention can be suitably used for lamination because the adhesive strength is very high. In the case of the adhesive for lamination, the dry coating weight is preferably in the range of 0.5 g/m 2 to 20.0 g/m 2 . If it is 0.5 g/m 2 or more, the continuous and uniform coating properties are good, and when it is 20.0 g/m 2 or less, the solvent releasability after coating is good, and the balance between workability and solvent removal properties is excellent.
作為層壓方法,可藉由於將本發明的接著劑塗敷於下層後,層疊上層並藉由乾式層壓(乾式積層法)進行貼合,而獲得層壓積層體。層壓輥的溫度較佳為室溫~120℃左右,壓力較佳為3 kg/cm2 ~300 kg/cm2 左右。 另外,本發明的層壓積層體較佳為於製作後進行老化。老化條件的較佳溫度為25℃~100℃,時間為12小時~240小時,於其間產生接著強度。As a lamination method, after apply|coating the adhesive agent of this invention to a lower layer, laminating|stacking an upper layer, and bonding by dry lamination (dry lamination method), a laminated laminated body can be obtained. The temperature of the laminating roll is preferably about room temperature to about 120° C., and the pressure is preferably about 3 kg/cm 2 to 300 kg/cm 2 . In addition, it is preferable to age the laminated layer body of this invention after manufacture. The preferred temperature of the aging conditions is 25°C to 100°C, and the time is 12 hours to 240 hours, during which the bonding strength is generated.
<電池用構件> 包括金屬層與塑膠層的本發明的積層體能夠適宜用作電池的電解液密封膜或電極部保護膜等。該情況下,使極性有機溶媒及/或鹽酸等接觸塑膠層側來使用。特別是藉由以與包含極性有機溶媒及鹽的非水電解質接觸的狀態使用,而可特佳地用作非水電解質電池、固體電池等二次電池電解液密封膜或二次電池電極部保護膜。該情況下,藉由以塑膠層相向的方式折疊來進行熱封,而可用作電池用密封袋。本發明中使用的接著劑的熱封性優異,因而防止非水電解質的洩露,能夠長期用作電池。<Battery member> The laminate of the present invention including a metal layer and a plastic layer can be suitably used as a battery electrolyte sealing film, an electrode portion protective film, or the like. In this case, a polar organic solvent and/or hydrochloric acid, etc. are brought into contact with the plastic layer side for use. In particular, by being used in contact with a non-aqueous electrolyte containing a polar organic solvent and a salt, it can be used particularly preferably as a non-aqueous electrolyte battery, a secondary battery electrolyte solution sealing film such as a solid battery, or a secondary battery electrode portion protection membrane. In this case, it can be used as a sealed bag for batteries by being heat-sealed by folding it so that the plastic layers face each other. The adhesive used in the present invention is excellent in heat-sealability, prevents leakage of the non-aqueous electrolyte, and can be used as a battery for a long period of time.
作為所述極性有機溶媒,可列舉非質子性的極性溶媒,例如碳酸烷基酯、酯、酮等。具體而言,可列舉:碳酸伸乙酯、碳酸伸丙酯、碳酸伸丁酯、碳酸二甲酯、碳酸乙基甲酯、碳酸二乙酯、γ-丁內酯、1,2-二甲氧基乙烷、四氫呋喃、2-甲基四氫呋喃、1,3-二氧雜環戊烷、4-甲基-1,3-二氧雜環戊烷、甲酸甲酯、4-甲基-1,3-二氧代甲酸甲酯、甲基乙酸酯、甲基丙酸酯等。 作為鹽,可列舉鋰鹽、鈉鹽、鉀鹽等鹼金屬鹽。作為電池用途,一般使用LiPF6 、LiBF4 、Li-醯亞胺等鋰鹽。Examples of the polar organic solvent include aprotic polar solvents such as alkyl carbonates, esters, ketones, and the like. Specifically, ethylene carbonate, propylene carbonate, butyl carbonate, dimethyl carbonate, ethyl methyl carbonate, diethyl carbonate, γ-butyrolactone, 1,2-dimethyl carbonate can be mentioned. Oxyethane, tetrahydrofuran, 2-methyltetrahydrofuran, 1,3-dioxolane, 4-methyl-1,3-dioxolane, methyl formate, 4-methyl-1 , 3-Dioxoformate methyl ester, methyl acetate, methyl propionate, etc. Examples of the salt include alkali metal salts such as lithium salts, sodium salts, and potassium salts. For battery applications, lithium salts such as LiPF 6 , LiBF 4 , and Li-imide are generally used.
非水電解質為於環狀碳酸酯、鏈狀碳酸酯、該些的混合物等非質子性極性有機溶媒中溶解有0.5 mmol~3 mmol的所述鹼金屬鹽者。 本發明的積層體即便以與所述極性溶媒及/或鹽類、特別是作為該些的混合物的非水電解質接觸的狀態使用,亦可長期使用而不會產生金屬層、接著層、塑膠層的層間剝離。The non-aqueous electrolyte is obtained by dissolving 0.5 mmol to 3 mmol of the alkali metal salt in an aprotic polar organic solvent such as a cyclic carbonate, a chain carbonate, or a mixture thereof. Even if the layered product of the present invention is used in a state of being in contact with the polar solvent and/or salts, especially the non-aqueous electrolyte which is a mixture of these, it can be used for a long time without generating a metal layer, an adhesive layer and a plastic layer. interlayer peeling.
<電池> 本發明的電池為包括本發明的電池用構件者。作為具有本發明的積層體的電池用構件,可列舉電池電解液密封膜或電池電極部保護膜等。本發明的電池中,所述膜不產生層間剝離,而且可防止非水電解質的洩露,故可長期穩定地用作電池。 [實施例]<Battery> The battery of the present invention includes the battery member of the present invention. As a battery member which has the laminated body of this invention, a battery electrolyte solution sealing film, a battery electrode part protective film, etc. are mentioned. In the battery of the present invention, since the film does not cause interlayer peeling, and can prevent leakage of the nonaqueous electrolyte, it can be used stably as a battery for a long period of time. [Example]
以下,以如下實施例對本發明進行說明,但本發明並不限定於實施例。再者,於並無特別記述的情況下,單位為重量換算。Hereinafter, the present invention will be described with reference to the following examples, but the present invention is not limited to the examples. In addition, when there is no special description, the unit is a weight conversion.
(製備例1)清漆1的製備 將丙烯/1-丁烯共聚物300 g及甲苯1 L於氮氣環境下升溫至145℃,使丙烯/1-丁烯共聚物溶解於甲苯中。進而一邊攪拌一邊歷時4小時於系統中供給馬來酸酐38 g、二-第三丁基過氧化物16 g,繼而於145℃下攪拌2小時。冷卻後,投入大量丙酮,使馬來酸酐改質丙烯/1-丁烯共聚物(1)沈澱並進行過濾,利用丙酮清洗後,進行真空乾燥而獲得白色的固體。將所獲得的固體20份、甲基環己烷72份、乙酸乙酯7份、異丙醇(isopropyl alcohol,IPA)1份充分攪拌,獲得不揮發成分為20.0%的溶液即清漆1。(Preparation Example 1) Preparation of Varnish 1 300 g of propylene/1-butene copolymer and 1 L of toluene were heated to 145°C under nitrogen atmosphere, and the propylene/1-butene copolymer was dissolved in toluene. Furthermore, 38 g of maleic anhydride and 16 g of di-tert-butyl peroxide were supplied to the system over 4 hours while stirring, and the mixture was stirred at 145° C. for 2 hours. After cooling, a large amount of acetone was thrown in, the maleic anhydride-modified propylene/1-butene copolymer (1) was precipitated, filtered, washed with acetone, and then vacuum-dried to obtain a white solid. The obtained 20 parts of solids, 72 parts of methylcyclohexane, 7 parts of ethyl acetate, and 1 part of isopropyl alcohol (IPA) were fully stirred to obtain a solution with a non-volatile content of 20.0%, namely Varnish 1.
(製備例2)清漆2的製備 將GMP7550E(酸改質烯烴樹脂,樂天化學(Lotte Chemical)公司製造)16份、奧蘭(AUROREN)350S(酸改質烯烴樹脂,日本製紙製造)4份、甲基環己烷72份、乙酸乙酯5份、異丙醇(IPA)3份充分攪拌,製備不揮發成分為20.5%的溶液即清漆2。(Preparation Example 2) Preparation of Varnish 2 16 parts of GMP7550E (acid-modified olefin resin, manufactured by Lotte Chemical), 4 parts of AUROREN 350S (acid-modified olefin resin, manufactured by Nippon Paper), a 72 parts of cyclohexane, 5 parts of ethyl acetate, and 3 parts of isopropanol (IPA) were thoroughly stirred to prepare a solution of 20.5% nonvolatile content, namely Varnish 2.
(製備例3)清漆3的製備 加入20份的乙烯-丙烯酸共聚物(Poly(ethylene-co-acrylic acid))、72份的甲苯、8份的異丙醇(IPA)並充分攪拌,製成不揮發成分為19.9%的清漆3。(Preparation Example 3) Preparation of Varnish 3 20 parts of ethylene-co-acrylic acid (Poly(ethylene-co-acrylic acid)), 72 parts of toluene, 8 parts of isopropyl alcohol (IPA) were added and stirred well to prepare Clearcoat 3 with 19.9% non-volatile content.
(製備例4)清漆4的製備 於具備攪拌裝置、冷卻管、滴加漏斗及氮氣導入管的反應裝置中添加甲苯120 g後,於氮氣流下歷時約1小時升溫至系統內溫度到達約100℃,並保溫1小時。繼而,自預先添加有包含苯乙烯117 g、丙烯酸12.6 g、甲基丙烯酸月桂酯50.4 g、過氧化乙基己酸第三丁酯(日產化學股份有限公司製造的帕布吉(Perbutyl)O)3.6 g的混合液的滴加漏斗,於氮氣流下花費約4小時將混合液滴加至系統內,以相同溫度保溫6小時。藉由進行冷卻並加入甲苯90 g,而獲得不揮發成分為46.8%的含酸基丙烯酸酯樹脂(E)的溶液即清漆4。(Preparation Example 4) Preparation of Varnish 4 After adding 120 g of toluene to a reaction device equipped with a stirring device, a cooling pipe, a dropping funnel, and a nitrogen gas introduction pipe, the temperature was raised to about 100° C. in the system over a period of about 1 hour under a nitrogen flow. , and keep warm for 1 hour. Then, since 117 g of styrene, 12.6 g of acrylic acid, 50.4 g of lauryl methacrylate, and 3.6 g of tert-butyl peroxyethylhexanoate (Perbutyl O, manufactured by Nissan Chemical Co., Ltd.) were added in advance g into the dropping funnel of the mixed solution, the mixture was added dropwise to the system over about 4 hours under nitrogen flow, and the mixture was kept at the same temperature for 6 hours. By cooling and adding 90 g of toluene, varnish 4 was obtained as a solution of the acid group-containing acrylate resin (E) having a nonvolatile content of 46.8%.
(製備例5)清漆5的製備 於具備攪拌裝置、冷卻管、滴加漏斗及氮氣導入管的反應裝置中添加甲苯50 mL後,將氬氣起泡(bubbling)30分鐘來對系統內進行置換。將氬導入口自液面提起而變更為流動後,浸漬於浴溫135℃的油浴中,開始攪拌。於系統內到達一定溫度後,歷時1小時滴加將甲基丙烯酸環己酯38.20 g、甲基丙烯酸異冰片酯8.65 g、丙烯酸3.20 g、2,2'-偶氮雙異丁腈118 mg的5 mL甲苯溶液該四種混合的溶液。於氬氣流動下,保持浴溫而加熱攪拌4小時後,滴加2,2'-偶氮雙異丁腈119 mg的5 mL甲苯溶液,再次保持浴溫而加熱攪拌4小時。冷卻至室溫後,將所獲得的略呈白色混濁的均勻的溶液投入至約1.2 L的甲醇中,進行再沈澱。繼而,利用甲醇將沈澱清洗3次,接著於40℃下減壓乾燥一晚,結果獲得48 g的白色的固體。將所獲得的白色固體溶解於甲苯中,獲得含酸基丙烯酸酯樹脂(F)的溶液即清漆5。酸價為11.3 mgKOH/g,不揮發成分為30.0%。(Preparation Example 5) Preparation of Varnish 5 After adding 50 mL of toluene to a reaction device equipped with a stirring device, a cooling tube, a dropping funnel, and a nitrogen gas introduction tube, the inside of the system was replaced by bubbling argon gas for 30 minutes. . After the argon inlet was lifted from the liquid surface and changed to flow, it was immersed in an oil bath with a bath temperature of 135°C, and stirring was started. After reaching a certain temperature in the system, 38.20 g of cyclohexyl methacrylate, 8.65 g of isobornyl methacrylate, 3.20 g of acrylic acid, and 118 mg of 2,2'-azobisisobutyronitrile were added dropwise over 1 hour. 5 mL of toluene solution of the four mixed solutions. Under an argon flow, the bath temperature was maintained with heating and stirring for 4 hours, and a 5 mL toluene solution of 119 mg of 2,2'-azobisisobutyronitrile was added dropwise, and the bath temperature was maintained with heating and stirring for 4 hours again. After cooling to room temperature, the obtained slightly cloudy homogeneous solution was poured into about 1.2 L of methanol to perform reprecipitation. Next, the precipitate was washed three times with methanol, and then dried under reduced pressure at 40° C. overnight to obtain 48 g of white solid. The obtained white solid was dissolved in toluene to obtain varnish 5 which is a solution of acid group-containing acrylate resin (F). The acid value was 11.3 mgKOH/g, and the nonvolatile content was 30.0%.
(製備例6)清漆6的製備 於具備攪拌裝置、溫度計、冷卻管、滴加裝置的玻璃燒瓶中添加DMPA(2,2-二羥甲基丙酸)90重量份、作為溶媒的甲基乙基酮54重量份、四氫呋喃81重量份,於氮氣流下進行攪拌。繼而,添加XDI(二甲苯二異氰酸酯,商品名:塔克耐德(Takenate)500,三井化學製造)56重量份,升溫至60℃。攪拌1小時後,將溫度降至40℃以下,然後進而添加56重量份的XDI,並再次升溫至60℃。繼續進行反應直至藉由紅外光譜法而確認異氰酸酯基消失。繼而,加入作為稀釋溶媒的甲醇148重量份,獲得含有含羧基的胺基甲酸酯樹脂「DMPA/XDI」50重量%的含酸基聚胺基甲酸酯樹脂(G)的溶液即清漆6。(Preparation Example 6) Preparation of Varnish 6 Into a glass flask equipped with a stirring device, a thermometer, a cooling tube, and a dropping device, 90 parts by weight of DMPA (2,2-dimethylolpropionic acid) and methylethyl acetate as a solvent were added. 54 parts by weight of base ketone and 81 parts by weight of tetrahydrofuran were stirred under nitrogen flow. Next, 56 parts by weight of XDI (xylene diisocyanate, trade name: Takenate 500, manufactured by Mitsui Chemicals) was added, and the temperature was raised to 60°C. After stirring for 1 hour, the temperature was lowered to 40°C or lower, and 56 parts by weight of XDI was further added, and the temperature was raised to 60°C again. The reaction was continued until the disappearance of the isocyanate group was confirmed by infrared spectroscopy. Next, 148 parts by weight of methanol was added as a diluent to obtain varnish 6, which is a solution of the acid group-containing polyurethane resin (G) containing 50% by weight of the carboxyl group-containing urethane resin "DMPA/XDI". .
(製備例7)清漆7的製備 加入20份的聚烯烴樹脂希蠟(Hi-wax)NL100(三井化學公司製造)、80份的甲苯,充分攪拌而製成不揮發成分為20.1%的溶液即清漆7。(Preparation Example 7) Preparation of Varnish 7 20 parts of polyolefin resin Hi-wax NL100 (manufactured by Mitsui Chemicals Co., Ltd.) and 80 parts of toluene were added and stirred well to prepare a solution with a non-volatile content of 20.1%. Varnish 7.
關於所準備的含酸基樹脂,將各樹脂的酸價示於以下表1中。再者,作為酸價的測定方法,含酸基聚烯烴樹脂是利用以上所述的酸價測定方法-2,含酸基聚丙烯酸酯樹脂及含酸基聚胺基甲酸酯樹脂是利用酸價測定方法-1。Regarding the prepared acid group-containing resin, the acid value of each resin is shown in Table 1 below. In addition, as a method for measuring the acid value, the acid group-containing polyolefin resin was measured by the above-mentioned acid value measurement method-2, and the acid group-containing polyacrylate resin and the acid group-containing polyurethane resin were measured by using an acid group. Valence Determination Method-1.
[表1]
合成例1 二羥基化合物(Ph-1)的合成 於安裝有溫度計、攪拌機的燒瓶中添加1,6-己二醇的二縮水甘油醚(迪愛生(DIC)股份有限公司製造;商品名艾比克隆(EPICLON)726D,環氧當量124 g/eq)744 g(6當量)及雙酚A(羥基當量114 g/eq)1368 g(12當量),花費30分鐘升溫至140℃後,添加4%氫氧化鈉水溶液5 g。其後,花費30分鐘升溫至150℃,進而於150℃下反應3小時。其後,添加中和量的磷酸鈉,獲得羥基化合物(Ph-1)2090 g。根據核磁共振(nuclear magnetic resonance,NMR)光譜(13 C),另外,根據質譜中獲得相當於所述通式(1)的n為1的理論結構的M+ =687及相當於n為2的理論結構的M+ =1145的峰值,確認到該羥基化合物(Ph-1)含有下述結構式(B-1)所表示的結構的羥基化合物。該羥基化合物(Ph-1)的藉由凝膠滲透層析法(gel permeation chromatography,GPC)而算出的羥基當量為262 g/eq,根據羥基當量算出的結構式(B-1)中的n的平均值為0.6。Synthesis Example 1 Synthesis of dihydroxy compound (Ph-1) Diglycidyl ether of 1,6-hexanediol (manufactured by DIC Co., Ltd.; trade name Abby) was added to a flask equipped with a thermometer and a stirrer Clone (EPICLON) 726D, epoxy equivalent 124 g/eq) 744 g (6 equivalents) and bisphenol A (hydroxyl equivalent 114 g/eq) 1368 g (12 equivalents), took 30 minutes to warm up to 140°C, add 4 5 g of % sodium hydroxide aqueous solution. Then, the temperature was raised to 150°C over 30 minutes, and the reaction was further performed at 150°C for 3 hours. Then, the neutralized amount of sodium phosphate was added, and 2090 g of hydroxy compounds (Ph-1) were obtained. According to the nuclear magnetic resonance (NMR) spectrum ( 13 C), in addition, according to the mass spectrum, M + =687 corresponding to the theoretical structure of the general formula (1) where n is 1 and corresponding to n is 2 It was confirmed that the hydroxy compound (Ph-1) contains the hydroxy compound of the structure represented by the following structural formula (B-1) from the peak of M + =1145 of the theoretical structure. The hydroxyl equivalent of this hydroxyl compound (Ph-1) calculated by gel permeation chromatography (GPC) was 262 g/eq, and n in structural formula (B-1) calculated from the hydroxyl equivalent The average value is 0.6.
[化14] [Chemical 14]
合成例2 環氧化合物(Ep-1)的合成 於安裝有溫度計、滴加漏斗、冷卻管、攪拌機的燒瓶中添加實施例1中獲得的羥基化合物(Ph-1)261 g(羥基當量為261 g/eq.)、表氯醇1110 g(12莫耳)、正丁醇222 g並使其溶解。其後,一邊實施氮氣吹除,一邊升溫至65℃後,減壓至共沸的壓力,且歷時5小時滴加49%氫氧化鈉水溶液122 g(1.5莫耳)。繼而,於該條件下繼續攪拌0.5小時。其間,利用迪恩-斯達克分離器(Dean-Stark trap)將共沸時蒸餾出的餾出份分離,去除水層,將有機層返回至反應系統內進行反應。其後,對未反應的表氯醇進行減壓蒸餾將其蒸餾去除。於此時獲得的粗環氧樹脂中加入甲基異丁基酮1000 g及正丁醇100 g並進行溶解。進而,於該溶液中添加10%氫氧化鈉水溶液20 g並於80℃下反應2小時後,利用300 g的水反覆水洗3次直至清洗液的PH為中性。繼而,藉由共沸而將系統內脫水,經過精密過濾後於減壓下將溶媒蒸餾去除,獲得液狀的環氧樹脂(Ep-1)380 g。根據NMR光譜(13 C),另外,根據質譜中獲得相當於所述結構式(A1-3)中p=1、q=1、r=0的理論結構的M+ =798及相當於p=2、q=2、r=0的理論結構的M+ =1257的峰值,確認到該環氧樹脂(Ep-1)含有所述結構式(A1-3)所表示的結構的環氧樹脂。所獲得的環氧樹脂(Ep-1)包含所述結構式(A1-3)中p=0、q=0、r=0的化合物,且藉由GPC進行確認的結果為該混合物中以29重量%的比例含有p=0、q=0、r=0的化合物。另外,該環氧樹脂(Ep-1)的環氧當量為350 g/eq.,黏度為2000 Pa·s(25℃,E型黏度法),根據環氧當量而算出的所述結構式(A1-3)中的r的平均值為0.1。Synthesis Example 2 Synthesis of Epoxy Compound (Ep-1) To a flask equipped with a thermometer, a dropping funnel, a cooling pipe, and a stirrer, 261 g of the hydroxy compound (Ph-1) obtained in Example 1 (hydroxyl equivalent: 261 g/eq.), 1110 g (12 moles) of epichlorohydrin, and 222 g of n-butanol were dissolved. Then, the temperature was raised to 65° C. while carrying out nitrogen purge, and the pressure was reduced to an azeotropic pressure, and 122 g (1.5 mol) of a 49% aqueous sodium hydroxide solution was added dropwise over 5 hours. Then, stirring was continued under this condition for 0.5 hour. During this time, the distillate fraction distilled during azeotropy was separated by a Dean-Stark trap, the water layer was removed, and the organic layer was returned to the reaction system for reaction. Then, the unreacted epichlorohydrin was distilled off under reduced pressure. To the crude epoxy resin obtained at this time, 1000 g of methyl isobutyl ketone and 100 g of n-butanol were added and dissolved. Furthermore, 20 g of a 10% aqueous sodium hydroxide solution was added to this solution, and the solution was reacted at 80° C. for 2 hours, and then washed with 300 g of water three times until the pH of the washing solution became neutral. Then, the inside of the system was dehydrated by azeotropy, the solvent was distilled off under reduced pressure after fine filtration, and 380 g of a liquid epoxy resin (Ep-1) was obtained. According to the NMR spectrum ( 13 C), in addition, according to the mass spectrum, M + =798 corresponding to the theoretical structure of p=1, q=1, r=0 in the structural formula (A1-3) and corresponding to p= 2. The peak value of M + =1257 in the theoretical structure of q=2 and r=0, it was confirmed that the epoxy resin (Ep-1) contains the epoxy resin of the structure represented by the structural formula (A1-3). The obtained epoxy resin (Ep-1) contains the compound of p=0, q=0, r=0 in the structural formula (A1-3), and the result of confirmation by GPC is that the mixture contains 29. The proportions by weight contain compounds with p=0, q=0, r=0. In addition, the epoxy equivalent of this epoxy resin (Ep-1) was 350 g/eq., the viscosity was 2000 Pa·s (25°C, E-type viscosity method), and the structural formula ( The average value of r in A1-3) is 0.1.
(實施例1)接著劑1的製作 加入100份的清漆1、0.7份的環氧化合物(Ep-1)、0.01份的三苯基膦、3份的乙酸乙酯、1份的異丙醇並進行充分攪拌,製作不揮發成分20%的接著劑1。(Example 1) Preparation of Adhesive 1 100 parts of varnish 1, 0.7 part of epoxy compound (Ep-1), 0.01 part of triphenylphosphine, 3 parts of ethyl acetate, and 1 part of isopropanol were added The mixture was sufficiently stirred to prepare an adhesive 1 with a non-volatile content of 20%.
<積層體的製作> 利用棒塗機將實施例1中製作的接著劑1以5 g/m2 (乾式)塗佈於鋁箔(「1N30H」30 μm,東洋鋁公司製造),以80℃乾燥1分鐘後,於100℃下與CPP膜(聚烯烴膜「ET-20」40 μm,岡本(Okamoto)公司製造)貼合而製作積層體1。 其後,以70℃老化5日後,測定初始接著強度。<Preparation of laminated body> The adhesive agent 1 prepared in Example 1 was coated on aluminum foil (“1N30H” 30 μm, manufactured by Toyo Aluminum Co., Ltd.) at 5 g/m 2 (dry type) using a bar coater, and dried at 80° C. One minute later, it was bonded to a CPP film (polyolefin film "ET-20" 40 μm, manufactured by Okamoto Co., Ltd.) at 100° C. to produce a laminate 1 . Then, after aging at 70°C for 5 days, the initial bonding strength was measured.
<初始接著強度的測定> 於A&D(股)製造的滕喜龍(Tensilon)試驗中,將積層體切割為15 mm的寬度,測定180°剝離強度。<Measurement of Initial Adhesion Strength> In a Tensilon test manufactured by A&D Co., Ltd., the laminate was cut into a width of 15 mm, and the 180° peel strength was measured.
<耐電解液性> 作為電解液,準備於碳酸伸乙酯:碳酸乙基甲酯:碳酸二甲酯=1:1:1(wt%)混合液中添加有LiPF6 :1 mol及碳酸伸乙烯酯:1 wt%的溶液。 將積層體1於電解液35g中以85℃浸漬7日,如下所述根據浸漬前後的接著強度的保持率來實施評價。 接著強度保持率(%)=浸漬後的接著強度(N/15 mm)/浸漬前的接著強度(N/15 mm) ◎:80%以上,○:80%~60%,×:60%以下<Electrolyte solution resistance> As an electrolyte solution, LiPF 6 : 1 mol and ethylene carbonate were added to a mixed solution of ethyl carbonate: ethyl methyl carbonate: dimethyl carbonate = 1: 1: 1 (wt %). Vinyl ester: 1 wt% solution. The layered body 1 was immersed in 35 g of the electrolytic solution at 85° C. for 7 days, and the evaluation was performed based on the retention rate of the adhesive strength before and after the immersion as follows. Adhesion strength retention rate (%) = Adhesion strength after immersion (N/15 mm) / Adhesion strength before immersion (N/15 mm) ◎: 80% or more, ○: 80% to 60%, ×: 60% or less
實施例2~實施例7 以與實施例1中記載的方法相同的方式,依據表2中所示的調配將各成分混合,製作接著劑及積層體。 對各例中獲得的積層體評價接著性能以及耐電解質性,將其結果示於表2中。Examples 2 to 7 In the same manner as in the method described in Example 1, each component was mixed according to the formulation shown in Table 2 to prepare an adhesive and a layered product. The adhesive properties and electrolyte resistance of the laminates obtained in each example were evaluated, and Table 2 shows the results.
[表2]
[表3]
庫來澤(Curezol)2E4MZ(四國化成工業公司製造的咪唑系硬化劑) 不揮發成分100% 艾比克隆(EPICLON)HP-4700(迪愛生(DIC)公司製造的萘型環氧) 不揮發成分100% [產業上之可利用性]Curezol 2E4MZ (Imidazole-based hardener manufactured by Shikoku Chemical Industry Co., Ltd.) Non-volatile content 100% EPICLON HP-4700 (Naphthalene-type epoxy manufactured by DIC Corporation) Non-volatile Ingredients 100% [Industrial Availability]
本發明的接著劑由於接著性、特別是與金屬或金屬氧化物層的接著性優異,進而於低溫固化下亦兼具耐電解質性,不會隨時間經過而產生層間剝離,因此能夠良好地用作層壓用接著劑或電池用接著劑。另外,所獲得的積層體能夠良好地用作電池用構件,且可獲得具有長期的使用穩定性的電池。Since the adhesive of the present invention is excellent in adhesiveness, especially adhesiveness with a metal or metal oxide layer, and also has electrolyte resistance even under low temperature curing, and does not cause interlayer peeling over time, it can be used satisfactorily. As a lamination adhesive or battery adhesive. In addition, the obtained laminate can be favorably used as a battery member, and a battery having long-term use stability can be obtained.
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