JP2020169250A - Adhesive, laminate, battery packaging material, and battery - Google Patents
Adhesive, laminate, battery packaging material, and battery Download PDFInfo
- Publication number
- JP2020169250A JP2020169250A JP2019070533A JP2019070533A JP2020169250A JP 2020169250 A JP2020169250 A JP 2020169250A JP 2019070533 A JP2019070533 A JP 2019070533A JP 2019070533 A JP2019070533 A JP 2019070533A JP 2020169250 A JP2020169250 A JP 2020169250A
- Authority
- JP
- Japan
- Prior art keywords
- resin
- adhesive
- acid
- mass
- base material
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Granted
Links
- 239000000853 adhesive Substances 0.000 title claims abstract description 99
- 230000001070 adhesive effect Effects 0.000 title claims abstract description 99
- 239000005022 packaging material Substances 0.000 title claims abstract description 17
- -1 imidazole compound Chemical class 0.000 claims abstract description 79
- 229920005989 resin Polymers 0.000 claims abstract description 75
- 239000011347 resin Substances 0.000 claims abstract description 74
- 239000002253 acid Substances 0.000 claims abstract description 73
- 150000001875 compounds Chemical class 0.000 claims abstract description 71
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 62
- 239000004593 Epoxy Substances 0.000 claims abstract description 52
- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 claims abstract description 36
- 229910052751 metal Inorganic materials 0.000 claims abstract description 27
- 239000002184 metal Substances 0.000 claims abstract description 27
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 27
- 150000002903 organophosphorus compounds Chemical class 0.000 claims abstract description 16
- 238000002156 mixing Methods 0.000 claims abstract description 15
- 239000000463 material Substances 0.000 claims description 70
- 229920000098 polyolefin Polymers 0.000 claims description 26
- 230000032683 aging Effects 0.000 claims description 20
- 238000000576 coating method Methods 0.000 claims description 17
- 239000011248 coating agent Substances 0.000 claims description 16
- 239000011888 foil Substances 0.000 claims description 15
- 150000008065 acid anhydrides Chemical class 0.000 claims description 13
- 239000012790 adhesive layer Substances 0.000 claims description 13
- 125000000524 functional group Chemical group 0.000 claims description 11
- 238000000465 moulding Methods 0.000 claims description 10
- 238000004519 manufacturing process Methods 0.000 claims description 2
- 239000000758 substrate Substances 0.000 abstract description 10
- 239000002585 base Substances 0.000 description 56
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 49
- 239000000178 monomer Substances 0.000 description 42
- 229920001577 copolymer Polymers 0.000 description 32
- 238000000034 method Methods 0.000 description 26
- 239000003822 epoxy resin Substances 0.000 description 21
- 229920000647 polyepoxide Polymers 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 20
- 229910052757 nitrogen Inorganic materials 0.000 description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 18
- 150000001336 alkenes Chemical class 0.000 description 17
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 15
- 238000006243 chemical reaction Methods 0.000 description 15
- 239000008151 electrolyte solution Substances 0.000 description 15
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 description 14
- 239000002904 solvent Substances 0.000 description 14
- 238000002844 melting Methods 0.000 description 13
- 230000008018 melting Effects 0.000 description 13
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- 239000000243 solution Substances 0.000 description 13
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 12
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 12
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 12
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 12
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 11
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 10
- 239000005977 Ethylene Substances 0.000 description 10
- 229910052782 aluminium Inorganic materials 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 125000003118 aryl group Chemical group 0.000 description 10
- 239000000203 mixture Substances 0.000 description 10
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- 125000003647 acryloyl group Chemical group O=C([*])C([H])=C([H])[H] 0.000 description 9
- 229920001519 homopolymer Polymers 0.000 description 9
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 9
- 235000011007 phosphoric acid Nutrition 0.000 description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 9
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 8
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 8
- 125000002723 alicyclic group Chemical group 0.000 description 8
- 239000010410 layer Substances 0.000 description 8
- 239000006224 matting agent Substances 0.000 description 8
- 239000000126 substance Substances 0.000 description 8
- 229920000178 Acrylic resin Polymers 0.000 description 7
- 239000004925 Acrylic resin Substances 0.000 description 7
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 7
- 230000000052 comparative effect Effects 0.000 description 7
- 229920001225 polyester resin Polymers 0.000 description 7
- 239000004645 polyester resin Substances 0.000 description 7
- 238000003860 storage Methods 0.000 description 7
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 6
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 6
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 6
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 6
- 229940125782 compound 2 Drugs 0.000 description 6
- 238000010438 heat treatment Methods 0.000 description 6
- 238000010030 laminating Methods 0.000 description 6
- 229910052759 nickel Inorganic materials 0.000 description 6
- 229920000642 polymer Polymers 0.000 description 6
- 238000011282 treatment Methods 0.000 description 6
- IMSODMZESSGVBE-UHFFFAOYSA-N 2-Oxazoline Chemical compound C1CN=CO1 IMSODMZESSGVBE-UHFFFAOYSA-N 0.000 description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 5
- HBBGRARXTFLTSG-UHFFFAOYSA-N Lithium ion Chemical compound [Li+] HBBGRARXTFLTSG-UHFFFAOYSA-N 0.000 description 5
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 5
- 239000011247 coating layer Substances 0.000 description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 5
- 238000005227 gel permeation chromatography Methods 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 5
- 201000006747 infectious mononucleosis Diseases 0.000 description 5
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 5
- 229910001416 lithium ion Inorganic materials 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 229920006122 polyamide resin Polymers 0.000 description 5
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 4
- 229910019142 PO4 Inorganic materials 0.000 description 4
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 4
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- 238000002835 absorbance Methods 0.000 description 4
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- 239000000806 elastomer Substances 0.000 description 4
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- LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 4
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- 150000002576 ketones Chemical class 0.000 description 4
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- 239000004702 low-density polyethylene Substances 0.000 description 4
- 238000001819 mass spectrum Methods 0.000 description 4
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 4
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- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
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- 238000005507 spraying Methods 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229920006132 styrene block copolymer Polymers 0.000 description 1
- 229920001935 styrene-ethylene-butadiene-styrene Polymers 0.000 description 1
- 150000003440 styrenes Chemical class 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 238000010557 suspension polymerization reaction Methods 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920006027 ternary co-polymer Polymers 0.000 description 1
- 150000003505 terpenes Chemical class 0.000 description 1
- 235000007586 terpenes Nutrition 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
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- LDHQCZJRKDOVOX-UHFFFAOYSA-N trans-crotonic acid Natural products CC=CC(O)=O LDHQCZJRKDOVOX-UHFFFAOYSA-N 0.000 description 1
- IUCJMVBFZDHPDX-UHFFFAOYSA-N tretamine Chemical compound C1CN1C1=NC(N2CC2)=NC(N2CC2)=N1 IUCJMVBFZDHPDX-UHFFFAOYSA-N 0.000 description 1
- 229950001353 tretamine Drugs 0.000 description 1
- 125000005409 triarylsulfonium group Chemical group 0.000 description 1
- TUQOTMZNTHZOKS-UHFFFAOYSA-N tributylphosphine Chemical compound CCCCP(CCCC)CCCC TUQOTMZNTHZOKS-UHFFFAOYSA-N 0.000 description 1
- JLGLQAWTXXGVEM-UHFFFAOYSA-N triethylene glycol monomethyl ether Chemical compound COCCOCCOCCO JLGLQAWTXXGVEM-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- DQZNLOXENNXVAD-UHFFFAOYSA-N trimethoxy-[2-(7-oxabicyclo[4.1.0]heptan-4-yl)ethyl]silane Chemical compound C1C(CC[Si](OC)(OC)OC)CCC2OC21 DQZNLOXENNXVAD-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
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- 125000003258 trimethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])[*:1] 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- UNXRWKVEANCORM-UHFFFAOYSA-N triphosphoric acid Chemical compound OP(O)(=O)OP(O)(=O)OP(O)(O)=O UNXRWKVEANCORM-UHFFFAOYSA-N 0.000 description 1
- RYXYUARTMQUYKV-UHFFFAOYSA-N tris(4-butylphenyl)phosphane Chemical compound C1=CC(CCCC)=CC=C1P(C=1C=CC(CCCC)=CC=1)C1=CC=C(CCCC)C=C1 RYXYUARTMQUYKV-UHFFFAOYSA-N 0.000 description 1
- WXAZIUYTQHYBFW-UHFFFAOYSA-N tris(4-methylphenyl)phosphane Chemical compound C1=CC(C)=CC=C1P(C=1C=CC(C)=CC=1)C1=CC=C(C)C=C1 WXAZIUYTQHYBFW-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
- 238000007740 vapor deposition Methods 0.000 description 1
- 229920001567 vinyl ester resin Polymers 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
- UKRDPEFKFJNXQM-UHFFFAOYSA-N vinylsilane Chemical class [SiH3]C=C UKRDPEFKFJNXQM-UHFFFAOYSA-N 0.000 description 1
- 239000010457 zeolite Substances 0.000 description 1
- 239000011787 zinc oxide Substances 0.000 description 1
Classifications
-
- 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
- Sealing Battery Cases Or Jackets (AREA)
- Laminated Bodies (AREA)
- Adhesive Tapes (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
Description
本発明は、接着剤、詳しくは樹脂基材と金属基材とを接着するのに好適な接着剤、当該接着剤を用いて得られる積層体、二次電池用外装材及び電池に関する。 The present invention relates to an adhesive, specifically an adhesive suitable for adhering a resin base material and a metal base material, a laminate obtained by using the adhesive, an exterior material for a secondary battery, and a battery.
リチウムイオン電池に代表される二次電池は、正極、負極およびその間に、電解液等を封入した構成をとっている。また、正極と負極の電気を外部に取り出すためのリード線を封入するための封入袋として、オレフィン樹脂からなるヒートシール層と、アルミニウム箔等の金属箔や金属蒸着層からなる金属基材とプラスチックを貼り合せた積層体を用いることが知られている(特許文献1、2)。 A secondary battery represented by a lithium ion battery has a configuration in which a positive electrode, a negative electrode, and an electrolytic solution or the like are sealed between them. Further, as an encapsulation bag for encapsulating lead wires for extracting electricity from the positive electrode and the negative electrode to the outside, a heat seal layer made of an olefin resin, a metal base material made of a metal foil such as an aluminum foil, or a metal vapor deposition layer, and plastic. It is known to use a laminated body obtained by laminating the above (Patent Documents 1 and 2).
接着剤を介してオレフィン樹脂からなるヒートシール層と金属基材とを貼り合せる際には、一般的に加温しながら接着剤の硬化を促進する、いわゆるエージング工程が設けられる。エージング工程におけるエージング温度、エージング時間は適宜選択すればよいが、一例としてオレフィン樹脂の熱収縮影響が小さい80℃以下で行うことが好ましい。一方で、エージング温度が低いほど、またエージング時間が短いほど接着剤の特性が発揮され難くなる傾向がある。 When the heat seal layer made of an olefin resin and the metal base material are bonded to each other via an adhesive, a so-called aging step is generally provided in which the curing of the adhesive is promoted while heating. The aging temperature and aging time in the aging step may be appropriately selected, but as an example, it is preferably performed at 80 ° C. or lower, which has a small effect of heat shrinkage of the olefin resin. On the other hand, the lower the aging temperature and the shorter the aging time, the more difficult it is for the adhesive to exhibit its characteristics.
本発明は、このような状況に鑑みなされたものであって、低温でエージングした場合であってもオレフィン樹脂のような非極性の基材と金属基材との接着性に優れた接着剤を提供することを目的とする。さらに、このような接着剤を用いて得られる積層体、当該積層体を用いて得られる二次電池外装材および電池を提供することを目的とする。 The present invention has been made in view of such a situation, and an adhesive having excellent adhesiveness between a non-polar base material such as an olefin resin and a metal base material even when aged at a low temperature. The purpose is to provide. Further, it is an object of the present invention to provide a laminate obtained by using such an adhesive, a secondary battery exterior material and a battery obtained by using the laminate.
本発明は、第1剤と、第2剤とを含み、第1剤が酸基含有樹脂を含み、第2剤が52℃における粘度が0.05Pa・s以上25Pa・s以下のエポキシ化合物を含み、さらに有機リン系化合物と、イミダゾール化合物と、を含み、有機リン化合物の配合量が樹脂100質量部に対して0.01質量部以上5質量部以下であり、イミダゾール化合物の配合量が樹脂100質量部に対して0.06質量部以上0.35質量部以下である接着剤に関する。 The present invention comprises an epoxy compound containing a first agent and a second agent, the first agent containing an acid group-containing resin, and the second agent having a viscosity of 0.05 Pa · s or more and 25 Pa · s or less at 52 ° C. It further contains an organic phosphorus compound and an imidazole compound, and the amount of the organic phosphorus compound compounded is 0.01 parts by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the resin, and the compounding amount of the imidazole compound is the resin. The present invention relates to an adhesive having a mass of 0.06 parts by mass or more and 0.35 parts by mass or less with respect to 100 parts by mass.
本発明の接着剤は、低温でエージングした場合であってもオレフィン樹脂のような非極性の基材と金属基材との接着性、耐電解液性に優れる。また、本発明の積層体は接着性、耐電解液性に優れる。 The adhesive of the present invention is excellent in adhesiveness and electrolytic solution resistance between a non-polar substrate such as an olefin resin and a metal substrate even when aged at a low temperature. Further, the laminate of the present invention is excellent in adhesiveness and electrolytic solution resistance.
<接着剤>
本発明の接着剤は、酸基含有樹脂(A1)を含む樹脂と、有機リン系化合物と、イミダゾール化合物とを含む第1剤と、52℃における粘度が0.05Pa・s以上25Pa・s以下のエポキシ化合物を含む第2剤とを含む。以下、本発明の接着剤の各成分について詳細に説明する。
<Adhesive>
The adhesive of the present invention contains a resin containing an acid group-containing resin (A1), a first agent containing an organic phosphorus compound, and an imidazole compound, and has a viscosity at 52 ° C. of 0.05 Pa · s or more and 25 Pa · s or less. Includes a second agent containing the epoxy compound of. Hereinafter, each component of the adhesive of the present invention will be described in detail.
(第1剤)
第1剤は、樹脂(A)として酸基含有樹脂(A1)を含む。酸基含有樹脂(A1)が備える酸基としては、カルボキシル基、無水カルボン酸基、スルホン酸基、リン酸基等が挙げられる。酸基含有樹脂はこれらのうち1種のみを備えるものであってもよいし、2種以上を備えるものであってもよい。酸基含有樹脂(A1)の樹脂骨格は、特に限定はないが、アクリル樹脂、ウレタン樹脂、オレフィン樹脂等を好ましく用いることができる。
(1st agent)
The first agent contains an acid group-containing resin (A1) as the resin (A). Examples of the acid group contained in the acid group-containing resin (A1) include a carboxyl group, an anhydrous carboxylic acid group, a sulfonic acid group, and a phosphoric acid group. The acid group-containing resin may include only one of these, or may include two or more of them. The resin skeleton of the acid group-containing resin (A1) is not particularly limited, but acrylic resin, urethane resin, olefin resin and the like can be preferably used.
酸基含有アクリル樹脂としては、例えば、(メタ)アクリロイル基を有する単量体及び酸基を有する重合性単量体を必須成分とし、必要に応じて他の重合性不飽和単量体と重合して得られる共重合体が挙げられる。(メタ)アクリロイル基を有する単量体は酸基を有する重合性単量体を兼ねていてもよく、この場合は酸基含有アクリル樹脂が(メタ)アクリロイル基及び酸基を有する重合性単量体の単独重合体であってもよい。なお、本明細書において「(メタ)アクリロイル基」とはアクリロイル基とメタクリロイル基の一方または両方をいい、「(メタ)アクリル酸」とはアクリル酸とメタクリル酸の一方または両方をいい、「(メタ)アクリレート」とはアクリレートとメタクリレートの一方または両方をいう。 The acid group-containing acrylic resin contains, for example, a monomer having a (meth) acryloyl group and a polymerizable monomer having an acid group as essential components, and polymerizes with other polymerizable unsaturated monomers as necessary. Examples thereof include the copolymer thus obtained. The monomer having a (meth) acryloyl group may also serve as a polymerizable monomer having an acid group. In this case, the acid group-containing acrylic resin is a polymerizable single amount having a (meth) acryloyl group and an acid group. It may be a homopolymer of the body. In the present specification, "(meth) acryloyl group" means one or both of acryloyl group and methacrylic acid group, and "(meth) acrylic acid" means one or both of acrylic acid and methacrylic acid. "Meta) acrylate" refers to one or both of acrylate and methacrylate.
酸基を有する重合性単量体としては、(メタ)アクリル酸;β-カルボキシルエチル(メタ)アクリレート、2−アクリロイルオキシエチルコハク酸、2−アクリロイルオキシエチルフタル酸、2−アクリロイルオキシエチルヘキサヒドロフタル酸及びこれらのラクトン変性物等、(メタ)アクリロイル基及びカルボキシル基を有する化合物;
2−(メタ)アクリロイルオキシエチルアシッドホスフェート、ビス(2−(メタ)アクリロイルオキシエチル)アシッドホスフェート、ポリエチレングリコールモノ(メタ)アクリレートのリン酸エステル、ポリプロピレングリコールモノ(メタ)アクリレートのリン酸エステル、ポリアルキレングリコールモノ(メタ)アクリレートのリン酸エステル、リン酸メチレン(メタ)アクリレート、リン酸トリメチレン(メタ)アクリレート、リン酸プロピレン(メタ)アクリレート、リン酸テトラメチレン(メタ)アクリレート等の(メタ)アクリロイル基及びリン酸基を有する化合物;
2−スルホエチル(メタ)アクリレート、2−スルホプロピル(メタ)アクリレート、2−ヒドロキシ−3−(メタ)アクリロキシプロパンスルホン酸、2−(メタ)アクリルアミド−2−メチルプロパンスルホン酸又はこれらの塩等の(メタ)アクリロイル基及びスルホン酸基を有する化合物;
クロトン酸、マレイン酸、無水マレイン酸、フマル酸、シトラコン酸、グルタコン酸、イタコン酸等が挙げられる。これらは単独で用いてもよいし、2種以上を併用してもよい。
The polymerizable monomer having an acid group includes (meth) acrylic acid; β-carboxyethyl (meth) acrylate, 2-acryloyloxyethyl succinic acid, 2-acryloyloxyethylphthalic acid, 2-acryloyloxyethylhexahydro. Compounds with (meth) acryloyl and carboxyl groups, such as phthalic acid and modified lactones thereof;
2- (Meta) acryloyloxyethyl acid phosphate, bis (2- (meth) acryloyloxyethyl) acid phosphate, polyethylene glycol mono (meth) acrylate phosphate, polypropylene glycol mono (meth) acrylate phosphate, poly (Meta) acryloyl such as phosphate ester of alkylene glycol mono (meth) acrylate, methylene (meth) acrylate, trimethylene (meth) acrylate, propylene (meth) acrylate, tetramethylene (meth) acrylate, etc. Compounds with groups and phosphate groups;
2-Sulfoethyl (meth) acrylate, 2-sulfopropyl (meth) acrylate, 2-hydroxy-3- (meth) acryloxypropanesulfonic acid, 2- (meth) acrylamide-2-methylpropanesulfonic acid or salts thereof, etc. Compound having (meth) acryloyl group and sulfonic acid group;
Examples thereof include crotonic acid, maleic acid, maleic anhydride, fumaric acid, citraconic acid, glutaconic acid, and itaconic acid. These may be used alone or in combination of two or more.
(メタ)アクリロイル基を有する単量体としては、例えば、
メチル(メタ)アクリレート、エチル(メタ)アクリレート、プロピル(メタ)アクリレート、n−ブチル(メタ)アクリレート、t−ブチル(メタ)アクリレート、ペンチル(メタ)アクリレート、ヘキシル(メタ)アクリレート、ヘプチル(メタ)アクリレート、オクチル(メタ)アクリレート、ノニル(メタ)アクリレート、デシル(メタ)アクリレート、ドデシル(メタ)アクリレート、テトラデシル(メタ)アクリレート、ヘキサデシル(メタ)アクリレート、オクタデシル(メタ)アクリレート、ドコシル(メタ)アクリレート等の、炭素原子数が1〜22のアルキル基を有する(メタ)アクリレート;
Examples of the monomer having a (meth) acryloyl group include, for example.
Methyl (meth) acrylate, ethyl (meth) acrylate, propyl (meth) acrylate, n-butyl (meth) acrylate, t-butyl (meth) acrylate, pentyl (meth) acrylate, hexyl (meth) acrylate, heptyl (meth) Acrylate, octyl (meth) acrylate, nonyl (meth) acrylate, decyl (meth) acrylate, dodecyl (meth) acrylate, tetradecyl (meth) acrylate, hexadecyl (meth) acrylate, octadecyl (meth) acrylate, docosyl (meth) acrylate, etc. (Meta) acrylate having an alkyl group having 1 to 22 carbon atoms;
シクロヘキシル(メタ)アクリレート、イソボルニル(メタ)アクリレート、ジシクロペンタニル(メタ)アクリレート、ジシクロペンタニルオキシエチル(メタ)アクリレート等の、シクロアルキル基を有する(メタ)アクリレート; (Meta) acrylates having a cycloalkyl group, such as cyclohexyl (meth) acrylates, isobornyl (meth) acrylates, dicyclopentanyl (meth) acrylates, dicyclopentanyloxyethyl (meth) acrylates;
ベンゾイルオキシエチル(メタ)アクリレート、ベンジル(メタ)アクリレート、フェニルエチル(メタ)アクリレート、フェノキシエチル(メタ)アクリレート、フェノキシジエチレングリコール(メタ)アクリレート、2−ヒドロキシ−3−フェノキシプロピル(メタ)アクリレート等の、芳香環を有する(メタ)アクリレート; Benoxyyloxyethyl (meth) acrylate, benzyl (meth) acrylate, phenylethyl (meth) acrylate, phenoxyethyl (meth) acrylate, phenoxydiethylene glycol (meth) acrylate, 2-hydroxy-3-phenoxypropyl (meth) acrylate, etc. (Meta) acrylate with aromatic ring;
ヒドロキシエチル(メタ)アクリレート、ヒドロキシプロピル(メタ)アクリレート、ヒドロキシブチル(メタ)アクリレート、グリセロール(メタ)アクリレート、ラクトン変性ヒドロキシエチル(メタ)アクリレート、ポリエチレングリコール(メタ)アクリレート、ポリプロピレングリコール(メタ)アクリレート、ポリアルキレングリコール等の、ヒドロキシアルキル基を有する(メタ)アクリレート; Hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, hydroxybutyl (meth) acrylate, glycerol (meth) acrylate, lactone-modified hydroxyethyl (meth) acrylate, polyethylene glycol (meth) acrylate, polypropylene glycol (meth) acrylate, A (meth) acrylate having a hydroxyalkyl group, such as polyalkylene glycol;
2,2,2−トリフルオロエチル(メタ)アクリレート、2,2,3,3−テトラフルオロプロピル(メタ)アクリレート、1H,1H,5H−オクタフルオロペンチル(メタ)アクリレート、1H,1H,2H,2H−ヘプタデカフルオロデシル(メタ)アクリレート、パーフルオロエチルオキシエチル(メタ)アクリレート等の、フルオロアルキル基の炭素の炭素原子数が1から18であるフルオロアルキル(メタ)アクリレート;
γ−メタクリロキシプロピルトリメトキシシラン等のシリル基含有(メタ)アクリレート;
N,N−ジメチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノエチル(メタ)アクリレート、N,N−ジエチルアミノプロピル(メタ)アクリレート等のN,N−ジアルキルアミノアルキル(メタ)アクリレート;
等が挙げられる。
2,2,2-Trifluoroethyl (meth) acrylate, 2,2,3,3-tetrafluoropropyl (meth) acrylate, 1H, 1H, 5H-octafluoropentyl (meth) acrylate, 1H, 1H, 2H, Fluoroalkyl (meth) acrylates such as 2H-heptadecafluorodecyl (meth) acrylate and perfluoroethyloxyethyl (meth) acrylate in which the number of carbon atoms of the carbon of the fluoroalkyl group is 1 to 18;
A silyl group-containing (meth) acrylate such as γ-methacryloxypropyltrimethoxysilane;
N, N-dialkylaminoalkyl (meth) acrylates such as N, N-dimethylaminoethyl (meth) acrylate, N, N-diethylaminoethyl (meth) acrylate, N, N-diethylaminopropyl (meth) acrylate;
And so on.
その他の重合性不飽和単量体としては、マレイン酸ジメチル、マレイン酸ジエチル、マレイン酸ジブチル、フマル酸ジメチル、フマル酸ジエチル、フマル酸ジブチル、イタコン酸ジメチル、イタコン酸ジブチル、フマル酸メチルエチル、フマル酸メチルブチル、イタコン酸メチルエチル等の、不飽和ジカルボン酸エステル類; Other polymerizable unsaturated monomers include dimethyl maleate, diethyl maleate, dibutyl maleate, dimethyl fumarate, diethyl fumarate, dibutyl fumarate, dimethyl itaconic acid, dibutyl itaconic acid, methyl ethyl fumarate, and fumarate. Unsaturated dicarboxylic acid esters such as methylbutyl acid acid and methylethyl itaconic acid;
スチレン、α−メチルスチレン、クロロスチレン等のスチレン誘導体;
ブタジエン、イソプレン、ピペリレン、ジメチルブタジエン等のジエン系化合物;
塩化ビニル、臭化ビニル等のハロゲン化ビニルやハロゲン化ビニリデン;
メチルビニルケトン、ブチルビニルケトン等の不飽和ケトン類;
酢酸ビニル、酪酸ビニル等のビニルエステル類;
Styrene derivatives such as styrene, α-methylstyrene, chlorostyrene;
Diene compounds such as butadiene, isoprene, piperylene, dimethyl butadiene;
Vinyl halides such as vinyl chloride and vinyl bromide and vinylidene halide;
Unsaturated ketones such as methyl vinyl ketone and butyl vinyl ketone;
Vinyl esters such as vinyl acetate and vinyl butyrate;
メチルビニルエーテル、ブチルビニルエーテル等のビニルエーテル類;
アクリロニトリル、メタクリロニトリル、シアン化ビニリデン等のシアン化ビニル類;
アクリルアミドやそのアルキド置換アミド類;
N−フェニルマレイミド、N−シクロヘキシルマレイミド等のN−置換マレイミド類;
Vinyl ethers such as methyl vinyl ether and butyl vinyl ether;
Vinyl cyanide such as acrylonitrile, methacrylonitrile, vinylidene cyanide;
Acrylamide and its alkyd-substituted amides;
N-substituted maleimides such as N-phenylmaleimide and N-cyclohexylmaleimide;
フッ化ビニル、フッ化ビニリデン、トリフルオロエチレン、クロロトリフルオロスチレン、ブロモトリフルオロエチレン、ペンタフルオロプロピレン、ヘキサフルオロプロピレン等のフッ素含有α−オレフィン類;トリフルオロメチルトリフルオロビニルエーテル、ペンタフルオロエチルトリフルオロビニルエーテル、ヘプタフルオロプロピルトリフルオロビニルエーテル等の、パーフルオロアルキル基の炭素原子数が1から18であるパーフルオロアルキル・パーフルオロビニルエーテル類;等のフッ素含有エチレン性不飽和単量体;
等が挙げられる。これらの他の重合性不飽和単量体は単独で用いてもよいし、2種以上を併用してもよい。
Fluorine-containing α-olefins such as vinyl fluoride, vinylidene fluoride, trifluoroethylene, chlorotrifluorostyrene, bromotrifluoroethylene, pentafluoropropylene, hexafluoropropylene; trifluoromethyltrifluorovinyl ether, pentafluoroethyltrifluoro Fluorine-containing ethylenically unsaturated monomers such as vinyl ethers, heptafluoropropyltrifluorovinyl ethers, and other perfluoroalkyl perfluorovinyl ethers having a perfluoroalkyl group having 1 to 18 carbon atoms;
And so on. These other polymerizable unsaturated monomers may be used alone or in combination of two or more.
酸基含有アクリル樹脂は公知慣用の方法を用いて重合(共重合)して得られ、その重合(共重合)形態は特に制限されない。ランダム共重合体、ブロック共重合体、グラフト共重合体等、いずれであってもよい。触媒(重合開始剤)の存在下で付加重合により製造することができる。塊状重合、溶液重合、懸濁重合、乳化重合等の公知の重合方法を使用できる。 The acid group-containing acrylic resin is obtained by polymerizing (copolymerizing) using a known and commonly used method, and the polymerization (copolymerization) form thereof is not particularly limited. It may be any of a random copolymer, a block copolymer, a graft copolymer and the like. It can be produced by addition polymerization in the presence of a catalyst (polymerization initiator). Known polymerization methods such as bulk polymerization, solution polymerization, suspension polymerization, and emulsion polymerization can be used.
酸基含有ウレタン樹脂としては、下記式(3)で表される化合物と、下記式(4)で表される化合物とを含む組成物の反応生成物が挙げられる。 Examples of the acid group-containing urethane resin include reaction products of a composition containing a compound represented by the following formula (3) and a compound represented by the following formula (4).
上記式(3)で表される化合物が有する芳香環構造としては、炭素原子数が6以上18以下の芳香環であることが好ましく、ベンゼン環、ナフタレン環、フェナントレン環、アントラセン環等が挙げられる。また、上記式(3)で表される化合物が有する芳香環は、少なくとも1つのフッ素原子により置換されていてもよく、パーフルオロフェニル基等が挙げられる。 The aromatic ring structure of the compound represented by the above formula (3) is preferably an aromatic ring having 6 or more and 18 or less carbon atoms, and examples thereof include a benzene ring, a naphthalene ring, a phenanthrene ring, and an anthracene ring. .. Further, the aromatic ring of the compound represented by the above formula (3) may be substituted with at least one fluorine atom, and examples thereof include a perfluorophenyl group.
上記式(3)で表される化合物が有する脂環構造としては、炭素原子数が3以上20以下のものが好ましく、単環、多環、縮合環のいずれであってもよい。脂環と芳香環が組み合わさった環構造であってもよい。
単環構造としては、シクロプロパン、シクロブタン、シクロペンタン、シクロヘキサン、シクロヘプタン、シクロオクタン、シクロノナン、シクロデカン、シクロウンデカン、シクロドデカン等のシクロアルカン;シクロプロペン、シクロブテン、シクロペンテン、シクロヘキセン、シクロヘプテン、シクロオクテン等のシクロアルケン;等が挙げられる。多環構造としては、キュバン、バスケタン、ハウサン等が挙げられる。縮合環構造としては、ビシクロウンデカンやデカヒドロナフタレン、ノルボルネンやノルボルナジエン等が挙げられる。
The alicyclic structure of the compound represented by the above formula (3) is preferably one having 3 or more and 20 or less carbon atoms, and may be a monocyclic ring, a polycyclic ring, or a condensed ring. It may have a ring structure in which an alicyclic ring and an aromatic ring are combined.
Examples of the monocyclic structure include cycloalkanes such as cyclopropane, cyclobutane, cyclopentane, cyclohexane, cycloheptane, cyclooctane, cyclononane, cyclodecane, cycloundecane, and cyclododecane; cyclopropene, cyclobutene, cyclopentene, cyclohexene, cycloheptene, cyclooctene, etc. Cycloalkene; etc. Examples of the polycyclic structure include cubane, basketane, and housane. Examples of the fused ring structure include bicycloundecane, decahydronaphthalene, norbornene and norbornadiene.
上記式(3)で表される化合物の好ましい具体例としては、m−キシリレンジイソシアネート、p−キシレンジイソシアネート、2,4−トルエンジイソシアネート、2,6−トルエンジイソシアネート、1,5−ナフタレンジイソシアネート等が挙げられる。 Preferred specific examples of the compound represented by the above formula (3) include m-xylene diisocyanate, p-xylene diisocyanate, 2,4-toluene diisocyanate, 2,6-toluene diisocyanate, 1,5-naphthalene diisocyanate and the like. Can be mentioned.
上記式(4)で表される化合物としては、m3が0であることが好ましい。また、上記式(4)で表される化合物としては、R7が炭素原子数1以上3以下の炭化水素基であることが好ましい。
上記式(4)で表される化合物の好ましい具体例としては、ジメチロールプロピオン酸、ジメチロールブタン酸が挙げられる。
As the compound represented by the above formula (4), m3 is preferably 0. Further, as the compound represented by the above formula (4), it is preferable that R 7 is a hydrocarbon group having 1 or more carbon atoms and 3 or less carbon atoms.
Preferred specific examples of the compound represented by the above formula (4) include dimethylolpropionic acid and trimethylolbutanoic acid.
酸基含有オレフィン樹脂としては、酸基含有モノマーの単独重合体または共重合体、酸基含有モノマーとオレフィン系モノマーとの共重合体、ポリオレフィンの酸基含有モノマー変性体等が挙げられる。 Examples of the acid group-containing olefin resin include homopolymers or copolymers of acid group-containing monomers, copolymers of acid group-containing monomers and olefin-based monomers, and modified acid group-containing monomers of polyolefins.
酸基含有モノマーの単独重合体または共重合体の調整に用いられる酸基含有モノマーとしては、エチレン性不飽和カルボン酸またはエチレン性不飽和カルボン酸無水物が好ましい。具体的には、アクリル酸、メタクリル酸、マレイン酸、イタコン酸、シトラコン酸、メサコン酸、無水マレイン酸、4−メチルシクロヘキセ−4−エン−1,2−ジカルボン酸無水物、ビシクロ[2.2.2]オクト−5−エン−2,3−ジカルボン酸無水物、1,2,3,4,5,8,9,10−オクタヒドロナフタレン−2,3−ジカルボン酸無水物、2−オクタ−1,3−ジケトスピロ[4.4]ノン−7−エン、ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボン酸無水物、マレオピマル酸、テトラヒドロフタル酸無水物、メチル−ビシクロ[2.2.1]ヘプト−5−エン−2,3−ジカルボン酸無水物、メチル―ノルボルネン−5−エン−2,3−ジカルボン酸無水物、ノルボルン−5−エン−2,3−ジカルボン酸無水物等が挙げられる。 As the acid group-containing monomer used for preparing the homopolymer or copolymer of the acid group-containing monomer, ethylenically unsaturated carboxylic acid or ethylenically unsaturated carboxylic acid anhydride is preferable. Specifically, acrylic acid, methacrylic acid, maleic acid, itaconic acid, citraconic acid, mesaconic acid, maleic anhydride, 4-methylcyclohexe-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 acid anhydride, 2- Octa-1,3-diketospiro [4.4] non-7-ene, bicyclo [2.2.1] hept-5-ene-2,3-dicarboxylic acid anhydride, maleopimalic acid, tetrahydrophthalic acid anhydride, Methyl-bicyclo [2.2.1] Hept-5-ene-2,3-dicarboxylic acid anhydride, Methyl-norbornene-5-ene-2,3-dicarboxylic acid anhydride, Norborn-5-ene-2, Examples thereof include 3-dicarboxylic acid anhydride.
酸基含有モノマーとオレフィン系モノマーとの共重合体の調整に用いられる酸基含有モノマーとしては、上述した酸基含有モノマーの単独重合体または共重合体の調整に用いられる酸基含有モノマーと同様のものを用いることができる。単独で用いてもよいし、2種以上を併用してもよい。無水マレイン酸を用いることが好ましい。 The acid group-containing monomer used for preparing the copolymer of the acid group-containing monomer and the olefin-based monomer is the same as the above-mentioned homopolymer of the acid group-containing monomer or the acid group-containing monomer used for preparing the copolymer. Can be used. It may be used alone or in combination of two or more. It is preferable to use maleic anhydride.
酸基含有モノマーとオレフィン系モノマーとの共重合体の調整に用いられるオレフィン系モノマーとしては、炭素原子数が2〜8のオレフィン、例えば、エチレン、プロピレン、イソブチレン、1−ブテン、4−メチル−1−ペンテン、ヘキセン、ビニルシクロヘキサンなどが挙げられる。これらのなかでも特に接着強度が良好なものとなることから炭素原子数3〜8のオレフィンが好ましく、プロピレン、及び1−ブテンがより好ましく、とりわけプロピレンと1−ブテンとを併用することが溶剤に対する耐性に優れ、接着強度に優れる点から好ましい。 Examples of the olefin-based monomer used for preparing the copolymer of the acid group-containing monomer and the olefin-based monomer include olefins having 2 to 8 carbon atoms, such as ethylene, propylene, isobutylene, 1-butene, and 4-methyl-. Examples thereof include 1-pentene, hexene and vinylcyclohexane. Among these, olefins having 3 to 8 carbon atoms are preferable, propylene and 1-butene are more preferable, and propylene and 1-butene are particularly used in combination with respect to the solvent because the adhesive strength is particularly good. It is preferable because it has excellent resistance and adhesive strength.
酸基含有モノマーとオレフィン系モノマーとの共重合体の調整には、上述した酸基含有モノマー、オレフィン系モノマーに加え、その他のエチレン性不飽和基を持つ化合物、例えばスチレン、ブタジエン、イソプレン等を併用してもよい。 In order to prepare the copolymer of the acid group-containing monomer and the olefin-based monomer, in addition to the acid group-containing monomer and the olefin-based monomer described above, other compounds having an ethylenically unsaturated group such as styrene, butadiene, isoprene and the like are used. It may be used together.
ポリオレフィンの酸基含有モノマー変性体の調整に用いられる酸基含有モノマーとしては、上述した酸基含有モノマーの単独重合体または共重合体の調整に用いられる酸基含有モノマーと同様のものを用いることができる。単独で用いてもよいし、2種以上を併用してもよい。無水マレイン酸を用いることが好ましい。 As the acid group-containing monomer used for preparing the modified acid group-containing monomer of polyolefin, the same as the above-mentioned homopolymer of the acid group-containing monomer or the same acid group-containing monomer used for preparing the copolymer should be used. Can be done. It may be used alone or in combination of two or more. It is preferable to use maleic anhydride.
ポリオレフィンの酸基含有モノマー変性体の調整に用いられるポリオレフィンとしては、炭素原子数2〜8のオレフィンの単独重合体や共重合体、炭素原子数2〜8のオレフィンと他のモノマーとの共重合体等が挙げられ、例えば、高密度ポリエチレン(HDPE)、低密度ポリエチレン(LDPE)、線状低密度ポリエチレン樹脂などのポリエチレン、ポリプロピレン、ポリイソブチレン、ポリ(1−ブテン)、ポリ(4−メチル−1−ペンテン)、ポリビニルシクロヘキサン、エチレン・プロピレンブロック共重合体、エチレン・プロピレンランダム共重合体、エチレン・1−ブテン共重合体、エチレン・4−メチル−1−ペンテン共重合体、エチレン・へキセン共重合体、プロピレン・1−ブテン共重合体などのα―オレフィン共重合体、エチレン・酢酸ビニル共重合体、エチレン・メチルメタクリレート共重合体、エチレン・酢酸ビニル・メチルメタクリレート共重合体、アイオノマー樹脂などが挙げられる。これらの中で特に接着強度が良好なものとなる点から炭素原子数3〜8のオレフィンの単独重合体、炭素原子数3〜8のオレフィンの2種以上の共重合体が好ましく、プロピレンの単独重合体、又はプロピレン・1−ブテン共重合体がより好ましく、とりわけプロピレン・1−ブテン共重合体が溶剤に対する耐性に優れ、接着強度に優れる点から好ましい。 Examples of the polyolefin used for preparing the acid group-containing monomer modified product of polyolefin include homopolymers and copolymers of olefins having 2 to 8 carbon atoms, and copolymers of olefins having 2 to 8 carbon atoms and other monomers. Examples thereof include high-density polyethylene (HDPE), low-density polyethylene (LDPE), and polyethylene such as linear low-density polyethylene resin, polypropylene, polyisobutylene, poly (1-butene), and poly (4-methyl-). 1-pentene), polyvinylcyclohexane, ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / 1-butene copolymer, ethylene / 4-methyl-1-pentene copolymer, ethylene / hexene Copolymers, α-olefin copolymers such as propylene / 1-butene copolymers, ethylene / vinyl acetate copolymers, ethylene / methyl methacrylate copolymers, ethylene / vinyl acetate / methyl methacrylate copolymers, ionomer resins And so on. Among these, a homopolymer of an olefin having 3 to 8 carbon atoms and two or more copolymers of an olefin having 3 to 8 carbon atoms are preferable from the viewpoint of particularly good adhesive strength, and propylene alone. A polymer or a propylene / 1-butene copolymer is more preferable, and a propylene / 1-butene copolymer is particularly preferable because it has excellent resistance to a solvent and excellent adhesive strength.
酸基含有モノマーによりポリオレフィンを変性する方法としては、グラフト変性や共重合化が挙げられる。グラフト変性によりポリオレフィンに酸基含有モノマーを反応させるには、具体的には、ポリオレフィンを溶融し、そこに酸基含有モノマー(グラフトモノマー)を添加してグラフト反応させる方法、ポリオレフィンを溶媒に溶解して溶液とし、そこにグラフトモノマーを添加してグラフト反応させる方法、有機溶剤に溶解したポリオレフィンと、グラフトモノマーとを混合し、ポリオレフィンの軟化温度または融点以上の温度で加熱し溶融状態にてラジカル重合と水素引き抜き反応を同時に行う方法等が挙げられる。 Examples of the method for modifying polyolefin with an acid group-containing monomer include graft modification and copolymerization. To react an acid group-containing monomer with a polyolefin by graft modification, specifically, a method of melting the polyolefin and adding an acid group-containing monomer (graft monomer) to the polyolefin for a graft reaction, or dissolving the polyolefin in a solvent. A method of making a solution by adding a graft monomer to the graft reaction, mixing the polyolefin dissolved in an organic solvent and the graft monomer, heating at a temperature higher than the softening temperature of the polyolefin or the melting point, and radical polymerization in a molten state. And a method of simultaneously performing the hydrogen abstraction reaction and the like.
いずれの場合にもグラフトモノマーを効率よくグラフト共重合させるためには、ラジカル開始剤の存在下にグラフト反応を実施することが好ましい。グラフト反応は、通常60〜350℃の条件で行われる。ラジカル開始剤の使用割合は変性前のポリオレフィン100重量部に対して、通常0.001〜1重量部の範囲である。 In either 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 graft reaction is usually carried out under the condition of 60 to 350 ° C. The ratio of the radical initiator used is usually in the range of 0.001 to 1 part by weight with respect to 100 parts by weight of the polyolefin before modification.
接着性を良好なものとするため酸基含有オレフィン樹脂の重量平均分子量は40,000以上であることが好ましい。また、適度な流動性を確保するため酸基含有オレフィン樹脂の重量平均分子量は200,000以下であることが好ましい。 The weight average molecular weight of the acid group-containing olefin resin is preferably 40,000 or more in order to improve the adhesiveness. Further, in order to ensure appropriate fluidity, the weight average molecular weight of the acid group-containing olefin resin is preferably 200,000 or less.
尚、本願発明において、重量平均分子量(Mw)、数平均分子量(Mn)は、下記条件のゲルパーミエーションクロマトグラフィー(GPC)により測定される値である。 In the present invention, the weight average molecular weight (Mw) and the number average molecular weight (Mn) are values measured by gel permeation chromatography (GPC) under the following conditions.
測定装置 ;東ソー株式会社製 HLC−8320GPC
カラム ;東ソー株式会社製 TSKgel 4000HXL、TSKgel 3000HXL、TSKgel 2000HXL、TSKgel 1000HXL
検出器 ;RI(示差屈折計)
データ処理;東ソー株式会社製 マルチステーションGPC−8020modelII
測定条件 ;カラム温度 40℃
溶媒 テトラヒドロフラン
流速 0.35ml/分
標準 ;単分散ポリスチレン
試料 ;樹脂固形分換算で0.2質量%のテトラヒドロフラン溶液をマイクロフィルターでろ過したもの(100μl)
Measuring device; HLC-8320GPC manufactured by Tosoh Corporation
Column; TSKgel 4000HXL, TSKgel 3000HXL, TSKgel 2000HXL, TSKgel 1000HXL manufactured by Tosoh Corporation
Detector; RI (Differential Refractometer)
Data processing; Multi-station GPC-8020modelII manufactured by Tosoh Corporation
Measurement conditions; column temperature 40 ° C
Solvent tetrahydrofuran
Flow velocity 0.35 ml / min Standard; Monodisperse polystyrene sample; 0.2 mass% tetrahydrofuran solution in terms of resin solid content filtered through a microfilter (100 μl)
酸基含有オレフィン樹脂は結晶性であることが好ましい。酸基含有オレフィン樹脂の融点は50℃以上であることが好ましく、60℃以上であることがより好ましく、65℃以上であることがより好ましい。また、酸基含有オレフィン樹脂の融点は120℃以下であることが好ましく、100℃以下であることがより好ましく、90℃以下であることがより好ましい。 The acid group-containing olefin resin is preferably crystalline. The melting point of the acid group-containing olefin resin is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and even more preferably 65 ° C. or higher. The melting point of the acid group-containing olefin resin is preferably 120 ° C. or lower, more preferably 100 ° C. or lower, and even more preferably 90 ° C. or lower.
酸基含有オレフィン樹脂の融点はDSC(示差走査熱量分析)により測定する。具体的には降温到達温度から昇温到達温度まで10℃/minで昇温後、10℃/minで降温到達温度まで冷却して熱履歴を除去した後、再度10℃/minで昇温到達点まで昇温する。2度目に昇温した際のピーク温度を融点とする。また、降温到達温度は結晶化温度よりも50℃以上低い温度に、昇温到達温度は融点温度よりも30℃位以上高い温度に設定する。降温到達温度、昇温到達温度は試測定して決定する。 The melting point of the acid group-containing olefin resin is measured by DSC (Differential Scanning Calorimetry). Specifically, after raising the temperature from the temperature at which the temperature falls to the temperature at which the temperature rises at 10 ° C./min, the temperature is cooled to the temperature at which the temperature falls at 10 ° C./min to remove the heat history, and then the temperature rises again at 10 ° C. The temperature rises to the point. The melting point is the peak temperature when the temperature is raised for the second time. Further, the temperature at which the temperature falls is set to a temperature 50 ° C. or higher lower than the crystallization temperature, and the temperature at which the temperature rises is reached is set to a temperature about 30 ° C. or higher higher than the melting point temperature. The temperature at which the temperature falls and the temperature at which the temperature rises rise are determined by trial measurement.
このような酸基含有オレフィン樹脂の具体例としては、無水マレイン酸変性ポリプロピレン、エチレン−(メタ)アクリル酸共重合体、エチレン−(メタ)アクリレート−無水マレイン酸三元共重合体等が挙げられる。酸基含有オレフィン樹脂の市販品としては、三菱化学(株)製「モディック」シリーズ、三井化学(株)製「アドマー」シリーズ、「ユニストール」シリーズ、東洋紡(株)製「トーヨータック」シリーズ、三洋化成(株)製「ユーメックス」シリーズ、日本ポリエチレン(株)製「レクスパールEAA」シリーズ、「レクスパールET」シリーズ、ダウ・ケミカル(株)製「プリマコール」シリーズ、三井・デュポンポリケミカル製「ニュクレル」シリーズ、アルケマ製「ボンダイン」シリーズ等が挙げられる。 Specific examples of such an acid group-containing olefin resin include maleic anhydride-modified polypropylene, ethylene- (meth) acrylic acid copolymer, ethylene- (meth) acrylate-maleic anhydride ternary copolymer and the like. .. Commercially available acid group-containing olefin resins include "Modic" series manufactured by Mitsubishi Chemicals, Inc., "Admer" series, "Unistor" series, and "Toyotack" series manufactured by Toyobo Co., Ltd. "Umex" series manufactured by Sanyo Kasei Co., Ltd., "Lexpearl EAA" series manufactured by Nippon Polyethylene Co., Ltd., "Lexpearl ET" series, "Primacol" series manufactured by Dow Chemicals Co., Ltd., Mitsui Dupont Polychemical Examples include the "Nucrel" series and the "Bondain" series made by Alchema.
酸基含有樹脂(A1)としては、上述した以外のものを用いることもでき、例えば、旭化成株式会社製のタフテックMシリーズ、クレイトンポリマージャパン株式会社製のクレイトンFGシリーズ等が挙げられる。 As the acid group-containing resin (A1), those other than those described above can be used, and examples thereof include Tough Tech M series manufactured by Asahi Kasei Corporation and Kraton FG series manufactured by Kraton Polymer Japan Co., Ltd.
第1剤は、樹脂(A)として、酸基含有樹脂(A1)に加えて反応性の官能基を有しない樹脂(A2)を含んでいてもよい。樹脂(A2)は結晶性のオレフィン樹脂であることが好ましい。樹脂(A2)が結晶性オレフィン樹脂であると接着剤の硬化塗膜の極性が低下し、電解液に対する耐性が向上する。 The first agent may contain, as the resin (A), a resin (A2) having no reactive functional group in addition to the acid group-containing resin (A1). The resin (A2) is preferably a crystalline olefin resin. When the resin (A2) is a crystalline olefin resin, the polarity of the cured coating film of the adhesive is lowered, and the resistance to the electrolytic solution is improved.
樹脂(A2)はとしては、炭素原子数2〜8のオレフィン、例えば、エチレン、プロピレン、イソブチレン、1−ブテン、4−メチル−1−ペンテン、ヘキセン、ビニルシクロヘキサンなどの単独重合体や共重合体、炭素原子数2〜8のオレフィンと他のモノマーとの共重合体等が挙げられ、具体的には、例えば、高密度ポリエチレン(HDPE)、低密度ポリエチレン(LDPE)、線状低密度ポリエチレン樹脂などのポリエチレン、ポリプロピレン、ポリイソブチレン、ポリ(1−ブテン)、ポリ(4−メチル−1−ペンテン)、ポリビニルシクロヘキサン、エチレン・プロピレンブロック共重合体、エチレン・プロピレンランダム共重合体、エチレン・1−ブテン共重合体、エチレン・4−メチル−1−ペンテン共重合体、エチレン・へキセン共重合体などのα―オレフィン共重合体、エチレン・メチルメタクリレート共重合体、プロピレン・1−ブテン共重合体などが挙げられる。これらの中で特に接着強度が良好なものとなる点から炭素原子数3〜8のオレフィンの単独重合体、炭素原子数3〜8のオレフィンの2種以上の共重合体が好ましく、プロピレンの単独重合体、又は共重合体がより好ましく、プロピレンの単独重合体がより好ましい。 The resin (A2) includes homopolymers and copolymers of olefins having 2 to 8 carbon atoms, such as ethylene, propylene, isobutylene, 1-butene, 4-methyl-1-pentene, hexene, and vinylcyclohexane. , Copolymers of olefins having 2 to 8 carbon atoms and other monomers, and specific examples thereof include high-density polyethylene (HDPE), low-density polyethylene (LDPE), and linear low-density polyethylene resin. Polyethylene, polypropylene, polyisobutylene, poly (1-butene), poly (4-methyl-1-pentene), polyvinylcyclohexane, ethylene / propylene block copolymer, ethylene / propylene random copolymer, ethylene / 1- Butene copolymer, α-olefin copolymer such as ethylene / 4-methyl-1-pentene copolymer, ethylene / hexene copolymer, ethylene / methyl methacrylate copolymer, propylene / 1-butene copolymer And so on. Among these, a homopolymer of an olefin having 3 to 8 carbon atoms and two or more copolymers of an olefin having 3 to 8 carbon atoms are preferable from the viewpoint of particularly good adhesive strength, and propylene alone. Polymers or copolymers are more preferred, and propylene homopolymers are more preferred.
樹脂(A2)は溶剤への溶解性が高く、塗工性が向上することから重量平均分子量が2000〜200,000であることが好ましい。樹脂(A2)の重量平均分子量は20,000〜180,000であることがより好ましく、40,000〜160,000であることがより好ましい。 The resin (A2) is highly soluble in a solvent and has improved coatability. Therefore, the weight average molecular weight is preferably 2000 to 200,000. The weight average molecular weight of the resin (A2) is more preferably 20,000 to 180,000, and even more preferably 40,000 to 160,000.
樹脂(A2)の融点は50℃〜100℃であることが好ましい。融点が50℃以上であることで、耐電解性をより確実に向上させることができ、100℃以下であることで塗工性を良好に保つことができる。樹脂(A2)の融点は60〜95℃であることがより好ましく、70〜90℃であることがより好ましい。 The melting point of the resin (A2) is preferably 50 ° C to 100 ° C. When the melting point is 50 ° C. or higher, the electrolytic resistance can be improved more reliably, and when the melting point is 100 ° C. or lower, the coatability can be kept good. The melting point of the resin (A2) is more preferably 60 to 95 ° C, more preferably 70 to 90 ° C.
第1剤は、酸価が1mgKOH/g以上であることが好ましく、5mgKOH/g以上であることがより好ましく、200mgKOH/g以下であることが好ましく、165mgKOH/g以下であることがより好ましい。200mgKOH/g以下であれば柔軟性に優れ、1mgKOH/g以上であれば耐熱性が良好である。 The acid value of the first agent is preferably 1 mgKOH / g or more, more preferably 5 mgKOH / g or more, preferably 200 mgKOH / g or less, and more preferably 165 mgKOH / g or less. If it is 200 mgKOH / g or less, the flexibility is excellent, and if it is 1 mgKOH / g or more, the heat resistance is good.
なお第1剤の酸価は、FT−IR(日本分光社製、FT−IR4200)を使用し、無水マレイン酸のクロロホルム溶液によって作成した検量線から得られる係数(f)、無水マレイン酸変性ポリオレフィン溶液における無水マレイン酸の無水環の伸縮ピーク(1780cm-1)の吸光度(I)とマレイン酸のカルボニル基の伸縮ピーク(1720cm-1)の吸光度(II)を用いて下記式により算出した値である。下記式において無水マレイン酸の分子量は98.06、水酸化カリウムの分子量は56.11である。 The acid value of the first agent is a coefficient (f) obtained from a calibration curve prepared by using FT-IR (FT-IR4200, manufactured by JASCO Corporation) and a chloroform solution of maleic anhydride, and a maleic anhydride-modified polyolefin. The value calculated by the following formula using the absorbance (I) of the expansion and contraction peak (1780 cm -1 ) of the anhydrous ring of maleic anhydride and the absorbance (II) of the expansion and contraction peak (1720 cm -1 ) of the carbonyl group of maleic anhydride in the solution. is there. In the following formula, maleic anhydride has a molecular weight of 98.06 and potassium hydroxide has a molecular weight of 56.11.
(第2剤)
第2剤は、酸基含有樹脂(A1)と反応性を有する、いわゆる硬化剤(B)として、52℃における粘度が0.05Pa・s以上25Pa・s以下のエポキシ化合物(B1)を含む。エポキシ化合物(B1)の粘度は回転粘度計を用い、コーン・プレート:1°×R25で測定する。エポキシ化合物(B1)は上記の粘度範囲を満足し、分子内にエポキシ基を有する化合物であれば特に限定されず、従来公知のものを用いることができる。一例として、エチレングリコール、プロピレングリコール、ヘキサンジオール、ネオペンチルグリコール、トリメチロールエタン、トリメチロールプロパン、ペンタエリトリトール、グリセリン、ジグリセリン、ソルビトール、スピログリコールもしくは水添ビスフェノールA等の脂肪族ポリオールのポリグリシジルエーテル型エポキシ樹脂;
ビスフェノールA型エポキシ樹脂、ビスフェノールF型エポキシ樹脂、ビスフェノールS型エポキシ樹脂、ビスフェノールAD型エポキシ樹脂等のビスフェノール型エポキシ樹脂;
フェノールノボラック樹脂やクレゾールノボラック樹脂のグリシジルエールであるノボラック型エポキシ樹脂等の芳香族エポキシ樹脂;
ビスフェノールA、ビスフェノールF、ビスフェノールS、ビスフェノールADなどの芳香族系ポリヒドロキシ化合物のエチレンオキシドもしくはプロピレンオキシド付加体であるポリオールのポリグリシジルエーテル;
ポリエチレングリコール、ポリプロピレングリコールもしくはポリテトラメチレングリコール等のポリエーテルポリオールのポリグリシジルエーテル型エポキシ樹脂;ビス(3,4−エポキシシクロヘキシルメチル)アジペート、3,4−エポキシシクロヘキシルメチル−3’,4’−エポキシシクロヘキシルカルボキシレート等の環状脂肪族型ポリエポキシ樹脂;
プロパントリカルボン酸、ブタンテトラカルボン酸、アジピン酸、フタル酸、テレフタル酸もしくはトリメリット酸等のポリカルボン酸のポリグリシジルエステル型エポキシ樹脂;
ブタジエン、ヘキサジエン、オクタジエン、ドデカジエン、シクロオクタジエン、α−ピネンもしくはビニルシクロヘキセン等の炭化水素系ジエンのビスエポキシ樹脂;
ポリブタジエンもしくはポリイソプレン等のジエンポリマーのエポキシ樹脂;
テトラグリシジルジアミノジフェニルメタン、トリグリシジルパラアミノフェノール、テトラグリシジルビスアミノメチルシクロヘキサン、ジグリシジルアニリン、テトラグリシジルメタキシリレンジアミン等のグリシジルアミン型エポキシ樹脂;
トリアジン、ヒダントイン等の複素環を含有するエポキシ樹脂が挙げられる。
これらのエポキシ樹脂は単独で用いてもよいし、2種以上組み合わせて用いてもよい。
(Second agent)
The second agent contains an epoxy compound (B1) having a viscosity at 52 ° C. of 0.05 Pa · s or more and 25 Pa · s or less as a so-called curing agent (B) having reactivity with the acid group-containing resin (A1). The viscosity of the epoxy compound (B1) is measured on a cone plate: 1 ° x R25 using a rotary viscometer. The epoxy compound (B1) is not particularly limited as long as it satisfies the above viscosity range and has an epoxy group in the molecule, and conventionally known compounds can be used. As an example, polyglycidyl ether of an aliphatic polyol such as ethylene glycol, propylene glycol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, glycerin, diglycerin, sorbitol, spiroglycol or hydrogenated bisphenol A. Mold epoxy resin;
Bisphenol type epoxy resin such as bisphenol A type epoxy resin, bisphenol F type epoxy resin, bisphenol S type epoxy resin, bisphenol AD type epoxy resin;
Aromatic epoxy resins such as phenol novolac resin and novolac type epoxy resin which is glycidyl ale of cresol novolak resin;
Ethylene oxide of aromatic polyhydroxy compounds such as bisphenol A, bisphenol F, bisphenol S, bisphenol AD, or polyglycidyl ether of polyol which is an adduct of propylene oxide;
Polyglycidyl ether type epoxy resin of polyether polyol such as polyethylene glycol, polypropylene glycol or polytetramethylene glycol; bis (3,4-epoxycyclohexylmethyl) adipate, 3,4-epoxycyclohexylmethyl-3', 4'-epoxy Cyclic aliphatic polyepoxy resin such as cyclohexylcarboxylate;
Polyglycidyl ester type epoxy resin of polycarboxylic acid such as propanetricarboxylic acid, butanetetracarboxylic acid, adipic acid, phthalic acid, terephthalic acid or trimellitic acid;
Hydrocarbon diene bisepoxy resins such as butadiene, hexadiene, octadiene, dodecadien, cyclooctadiene, α-pinene or vinylcyclohexene;
Diene polymer epoxy resin such as polybutadiene or polyisoprene;
Glycidylamine type epoxy resins such as tetraglycidyldiaminodiphenylmethane, triglycidylparaaminophenol, tetraglycidylbisaminomethylcyclohexane, diglycidylaniline, and tetraglycidylmethoxylylenediamine;
Epoxy resins containing a heterocycle such as triazine and hydantoin can be mentioned.
These epoxy resins may be used alone or in combination of two or more.
エポキシ化合物(B1)は、52℃における粘度が0.05Pa・s以上5Pa・s以下であることがより好ましく、0.05Pa・s以上2Pa・s以下であることがより好ましい。また、本発明に用いられるエポキシ化合物(B1)は、1分子中に2つ以上のエポキシ基と1つ以上の水酸基を備え、重量平均分子量が3000以下であるエポキシ化合物であることが好ましい。 The epoxy compound (B1) preferably has a viscosity at 52 ° C. of 0.05 Pa · s or more and 5 Pa · s or less, and more preferably 0.05 Pa · s or more and 2 Pa · s or less. Further, the epoxy compound (B1) used in the present invention is preferably an epoxy compound having two or more epoxy groups and one or more hydroxyl groups in one molecule and having a weight average molecular weight of 3000 or less.
第2剤は後述するエポキシ化合物(B2)や酸基含有樹脂(A1)と反応性を有する化合物(B3)を含んでいてもよいが、その場合も第2剤に含まれる硬化剤(B)に占めるエポキシ化合物(B1)の割合が4割以上であることが好ましい。これにより、低温でエージングを行った場合でも接着性、耐電解液性が良好な接着剤とすることができる。硬化剤(B)に占めるエポキシ化合物(B1)の割合は5割以上であることがより好ましく、8割以上であることがより好ましい。硬化剤(B)の全量がエポキシ化合物(B1)であってもよい。 The second agent may contain a compound (B3) reactive with an epoxy compound (B2) or an acid group-containing resin (A1) described later, but even in that case, the curing agent (B) contained in the second agent. The ratio of the epoxy compound (B1) to the total is preferably 40% or more. As a result, an adhesive having good adhesiveness and electrolytic solution resistance can be obtained even when aging is performed at a low temperature. The ratio of the epoxy compound (B1) to the curing agent (B) is more preferably 50% or more, and more preferably 80% or more. The total amount of the curing agent (B) may be the epoxy compound (B1).
第2剤は、エポキシ化合物(B1)以外のエポキシ化合物(B2)を含んでいてもよい。エポキシ化合物(B2)の構造としては、エポキシ化合物(B1)と同様のものが挙げられる。またエポキシ化合物(B1)に加えてエポキシ化合物(B2)を用いる場合、エポキシ化合物(B2)の配合量は硬化剤(B)の6割以下であることが好ましく、5割以下であることが好ましく、2割以下であることがより好ましい。 The second agent may contain an epoxy compound (B2) other than the epoxy compound (B1). Examples of the structure of the epoxy compound (B2) include those similar to those of the epoxy compound (B1). When the epoxy compound (B2) is used in addition to the epoxy compound (B1), the blending amount of the epoxy compound (B2) is preferably 60% or less, preferably 50% or less of the curing agent (B). It is more preferably 20% or less.
第2剤は、エポキシ化合物(B1)以外の、酸基含有樹脂(A1)と反応性を有する化合物(B3)を併用してもよい。エポキシ化合物(B1)と併用可能な他の化合物(B3)としては、多官能イソシアネート化合物、アジリジン基含有化合物、カルボジイミド、オキサゾリン、アミノ樹脂などが挙げられる。 As the second agent, a compound (B3) having reactivity with the acid group-containing resin (A1) other than the epoxy compound (B1) may be used in combination. Examples of the other compound (B3) that can be used in combination with the epoxy compound (B1) include a polyfunctional isocyanate compound, an aziridine group-containing compound, a carbodiimide, an oxazoline, and an amino resin.
多官能イソシアネート化合物としては、2,4−トリレンジイソシアネート、2,6−トリレンジイソシアネート、キシリレンジイソシアネート、ジフェニルメタンジイソシアネート、イソホロンジイソシアネート、1,5−ナフタレンジイソシアネート、ヘキサメチレンジイソシアネート、ビス(4−イソシアネートシクロヘキシル)メタン、若しくは水添化ジフェニルメタンジイソシアネート等のジイソシアネートおよびこれらから誘導された化合物、即ち、前記ジイソシアネートのイソシアヌレート体、アダクト体、ビウレット型、ウレトジオン体、アロファネート体、イソシアネート残基を有するプレポリマー(ジイソシアネートとポリオールから得られる低重合体)、若しくはこれらの複合体等が挙げられる。 Examples of the polyfunctional isocyanate compound include 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, xylylene diisocyanate, diphenylmethane diisocyanate, isophorone diisocyanate, 1,5-naphthalenedi isocyanate, hexamethylene diisocyanate, and bis (4-isocyanate cyclohexyl). ) Diisocyanates such as methane or hydrogenated diphenylmethane diisocyanates and compounds derived from them, that is, prepolymers (diisocyanates) having isocyanurates, adducts, biuret types, uretdiones, allophanates, and isocyanate residues of the diisocyanates. And a low polymer obtained from polyol), or a complex thereof and the like.
上述したような多官能イソシアネート化合物の一部のイソシアネート基を、イソシアネート基と反応性を有する化合物と反応させて得られる化合物を硬化剤として使用してもよい。イソシアネート基と反応性を有する化合物としては、ブチルアミン、ヘキシルアミン、オクチルアミン、2−エチルヘキシルアミン、ジブチルアミン、エチレンジアミン、ベンジルアミン、アニリン等のアミノ基を含有する化合物類:メタノール、エタノール、プロパノール、イソプロパノール、ブタノール、ヘキサノール、オクタノール、2−エチルヘキシルアルコール、ドデシルアルコール、エチレングリコール、プロピレングリコール、ベンジルアルコール、フェノール等の水酸基を含有する化合物類:アリルグリシジルエーテル、2−エチルヘキシルグリシジルエーテル、フェニルグリシジルエーテル、ネオペンチルグリコールジグリシジルエーテル、1,6−ヘキサンジオールグリシジルエーテル、シクロヘキサンジメタノールジグリシジルエーテル等のエポキシ基を有する化合物類:酢酸、ブタン酸、ヘキサン酸、オクタン酸、コハク酸、アジピン酸、セバシン酸、フタル酸等のカルボン酸を含有する化合物等が挙げられる。 A compound obtained by reacting a part of the isocyanate groups of the above-mentioned polyfunctional isocyanate compound with a compound having reactivity with the isocyanate group may be used as a curing agent. Compounds that have reactivity with isocyanate groups include amino group-containing compounds such as butylamine, hexylamine, octylamine, 2-ethylhexylamine, dibutylamine, ethylenediamine, benzylamine, and aniline: methanol, ethanol, propanol, and isopropanol. , Butanol, Hexanol, Octanol, 2-ethylhexyl alcohol, dodecyl alcohol, ethylene glycol, propylene glycol, benzyl alcohol, phenol and other compounds containing hydroxyl groups: allyl glycidyl ether, 2-ethylhexyl glycidyl ether, phenyl glycidyl ether, neopentyl Compounds having an epoxy group such as glycol diglycidyl ether, 1,6-hexanediol glycidyl ether, cyclohexanedimethanol diglycidyl ether: acetic acid, butanoic acid, hexanoic acid, octanoic acid, succinic acid, adipic acid, sebacic acid, phthal Examples thereof include compounds containing carboxylic acids such as acids.
アジリジン基含有化合物としては、例えば、N,N´−ヘキサメチレン−1,6−ビス(1−アジリジンカルボキシアミド)、N,N´−ジフェニルメタン−4,4´−ビス(1−アジリジンカルボキシアミド)、トリメチロールプロパン−トリ−β−アジリジニルプロピオネート)、N,N´−トルエン−2,4−ビス(1−アジリジンカルボキシアミド)、トリエチレンメラミン、トリメチロールプロパン−トリ−β(2−メチルアジリジン)プロピオネート、ビスイソフタロイル−1−2−メチルアジリジン、トリ−1−アジリジニルフォスフィンオキサイド、トリス−1−2−メチルアジリジンフォスフィンオキサイド等が挙げられる。 Examples of the aziridine group-containing compound include N, N'-hexamethylene-1,6-bis (1-aziridinecarboxyamide) and N, N'-diphenylmethane-4,4'-bis (1-aziridinecarboxyamide). , Trimethylolpropan-tri-β-aziridinyl propionate), N, N'-toluene-2,4-bis (1-aziridinecarboxyamide), triethylenemelamine, trimethylalopropan-tri-β (2) -Methylaziridine) propionate, bisisophthaloyl-2-methylaziridine, tri-1-aziridinylphosphine oxide, tris-1--2-methylaziridinephosphine oxide and the like can be mentioned.
カルボジイミドとしては、N,N’−ジ−o−トルイルカルボジイミド、N,N’−ジフェニルカルボジイミド、N,N’−ジ−2,6−ジメチルフェニルカルボジイミド、N,N’―ビス(2,6−ジイソプロピルフェニル)カルボジイミド、N,N’−ジオクチルデシルカルボジイミド、N−トリイル−N’−シクロヘキシルカルボジイミド、N,N’−ジ−2,2−tert.−ブチルフェニルカルボジイミド、N−トリイル−N’−フェニルカルボジイミド、N,N’−ジ−p−アミノフェニルカルボジイミド、N,N’−ジ−p−ヒドロキシフェニルカルボジイミド、N,N’−ジ−シクロヘキシルカルボジイミド、N,N’−ジ−p−トルイルカルボジイミド等が挙げられる。 Examples of carbodiimides include N, N'-di-o-toluyl carbodiimide, N, N'-diphenylcarbodiimide, N, N'-di-2,6-dimethylphenylcarbodiimide, and N, N'-bis (2,6-bis). Diisopropylphenyl) carbodiimide, N, N'-dioctyldecylcarbodiimide, N-triyl-N'-cyclohexylcarbodiimide, N, N'-di-2,2-tert. -Butylphenylcarbodiimide, N-triyl-N'-phenylcarbodiimide, N, N'-di-p-aminophenylcarbodiimide, N, N'-di-p-hydroxyphenylcarbodiimide, N, N'-di-cyclohexylcarbodiimide , N, N'-di-p-toluyl carbodiimide and the like.
オキサゾリンとしては、2−オキサゾリン、2−メチル−2−オキサゾリン、2−フェニル−2−オキサゾリン、2,5−ジメチル−2−オキサゾリン、2,4−ジフェニル−2−オキサゾリンなどのモノオキサゾリン化合物、2,2’−(1,3−フェニレン)−ビス(2−オキサゾリン)、2,2’−(1,2−エチレン)−ビス(2−オキサゾリン)、2,2’−(1,4ブチレン)−ビス(2−オキサゾリン)、2,2’−(1,4−フェニレン)−ビス(2−オキサゾリン)などが挙げられる。 Examples of the oxazoline include monooxazoline compounds such as 2-oxazoline, 2-methyl-2-oxazoline, 2-phenyl-2-oxazoline, 2,5-dimethyl-2-oxazoline and 2,4-diphenyl-2-oxazoline, 2. , 2'-(1,3-phenylene) -bis (2-oxazoline), 2,2'-(1,2-ethylene) -bis (2-oxazoline), 2,2'-(1,4 butylene) -Bis (2-oxazoline), 2,2'-(1,4-phenylene) -bis (2-oxazoline) and the like can be mentioned.
アミノ樹脂としては、メラミン樹脂、ベンゾグアナミン樹脂、尿素樹脂等が挙げられる。 Examples of the amino resin include melamine resin, benzoguanamine resin, urea resin and the like.
第2剤が酸基含有樹脂(A1)と反応性を有する化合物(B3)を含む場合、その配合量は硬化剤(B)の6割以下であることが好ましく、5割以下であることが好ましく、2割以下であることがより好ましい。 When the second agent contains a compound (B3) reactive with the acid group-containing resin (A1), the blending amount thereof is preferably 60% or less of the curing agent (B), and preferably 50% or less. It is preferably 20% or less, and more preferably 20% or less.
硬化剤(B)の配合量は、第1剤に含まれる反応性の官能基(A)と、第2剤に含まれ、第1剤の官能基(A)と反応可能な反応性の官能基(B)との当量比(官能基(A)/官能基(B))が0.01以上10以下となる範囲で調整されることが好ましく、より好ましくは0.1以上5.0以下である。これにより、接着性、耐電解液性に優れた接着剤とすることができる。 The blending amount of the curing agent (B) is the reactive functional group (A) contained in the first agent and the reactive functional group contained in the second agent and capable of reacting with the functional group (A) of the first agent. The equivalent ratio with the group (B) (functional group (A) / functional group (B)) is preferably adjusted in the range of 0.01 or more and 10 or less, more preferably 0.1 or more and 5.0 or less. Is. As a result, an adhesive having excellent adhesiveness and electrolytic solution resistance can be obtained.
(有機リン系化合物)
本発明の接着剤は、さらに有機リン系化合物(C)を含む。有機リン系化合物(C)としては、トリブチルホスフィン、メチルジフェニルホスフィン、トリフェニルホスフィン、トリス(4−メチルフェニル)ホスフィン、トリス(4−ブチルフェニル)ホスフィン、ジフェニルホスフィン、フェニルホスフィン等の有機ホスフィン化合物などが挙げられ、単独または2種以上を併用することができる。
(Organophosphorus compounds)
The adhesive of the present invention further contains an organic phosphorus compound (C). Examples of the organophosphorus compound (C) include organic phosphine compounds such as tributylphosphine, methyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris (4-butylphenyl) phosphine, diphenylphosphine, and phenylphosphine. Can be mentioned alone or in combination of two or more.
有機リン系化合物(C)の配合量は、第1剤の樹脂100質量部に対し、0.01質量部以上5質量部以下である。これにより、低温でエージングを行った際にも良好な接着強度、耐電解液性を備える接着剤とすることができる。有機リン系化合物(C)の配合量は、ある程度の量に達するとその効果が飽和し始めるため、第1剤の樹脂100質量部に対して0.01質量部以上0.5質量部以下であることがより好ましく、0.01質量部以上0.1質量部以下であることがより好ましい。 The blending amount of the organic phosphorus compound (C) is 0.01 part by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the resin of the first agent. As a result, it is possible to obtain an adhesive having good adhesive strength and electrolytic solution resistance even when aging is performed at a low temperature. Since the effect of the organophosphorus compound (C) begins to saturate when it reaches a certain amount, it should be 0.01 part by mass or more and 0.5 part by mass or less with respect to 100 parts by mass of the resin of the first agent. It is more preferable that the amount is 0.01 parts by mass or more and 0.1 parts by mass or less.
有機リン系化合物(C)は、第1剤または第2剤に予め配合されていてもよいし、第1剤と第2剤を混合する際に添加してもよい。 The organic phosphorus compound (C) may be premixed with the first agent or the second agent, or may be added when the first agent and the second agent are mixed.
(イミダゾール化合物)
本発明の接着剤は、さらにイミダゾール化合物(D)を含む。イミダゾール化合物(D)としては、2−メチルイミダゾール、1,2−ジメチルイミダゾール、2−フェニル−4−メチルイミダゾール、2−エチル−4−メチルイミダゾール、1−ベンジル−2−メチルイミダゾール、1−シアノエチル−2−エチル−4−メチルイミダゾール等が挙げられ、単独または、2種以上を併用することができる。
(Imidazole compound)
The adhesive of the present invention further comprises an imidazole compound (D). Examples of the imidazole compound (D) include 2-methylimidazole, 1,2-dimethylimidazole, 2-phenyl-4-methylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, and 1-cyanoethyl. Examples thereof include -2-ethyl-4-methylimidazole, and these can be used alone or in combination of two or more.
イミダゾール化合物(D)の配合量は、第1剤の樹脂100質量部に対し、0.06質量部以上0.35質量部以下である。これにより、低温でエージングを行った際にも良好な接着強度、耐電解液性を備える接着剤とすることができる。イミダゾール化合物(D)の配合量は、第1剤の樹脂100質量部に対して0.06質量部以上0.30質量部以下であることがより好ましく、0.06質量部以上0.25質量部以下であることがより好ましい。 The blending amount of the imidazole compound (D) is 0.06 parts by mass or more and 0.35 parts by mass or less with respect to 100 parts by mass of the resin of the first agent. As a result, it is possible to obtain an adhesive having good adhesive strength and electrolytic solution resistance even when aging is performed at a low temperature. The blending amount of the imidazole compound (D) is more preferably 0.06 parts by mass or more and 0.30 parts by mass or less, and 0.06 parts by mass or more and 0.25 parts by mass with respect to 100 parts by mass of the resin of the first agent. More preferably, it is less than or equal to a part.
イミダゾール化合物(D)は、第1剤に予め配合されていてもよいし、第1剤と第2剤とを混合する際に添加してもよい。 The imidazole compound (D) may be pre-blended in the first agent, or may be added when the first agent and the second agent are mixed.
本発明の接着剤が特に低温でエージングした際にも接着強度、耐電解液性に優れる理由については定かではないが、以下のように推測される。上記粘度範囲にあることでエポキシ化合物(B1)は有機溶剤(E)を乾燥させた後のエージング中の塗膜において、溶液状態で樹脂(A)中に均質に分散できる。ここに存在する適当量の有機リン系化合物(C)とイミダゾール化合物(D)とが極めて好適に酸基含有樹脂(A1)と硬化剤(B)との反応を促進し、耐電解液性に優れる硬化塗膜となると考えられる。
一方、粘度が低すぎるとエポキシ化合物(B1)は樹脂(A)中に分散できずに偏在してしまい、酸基含有樹脂(A1)を適切に架橋できず接着強度や耐電解液性に影響し、エポキシ化合物(B2)の粘度が高すぎると低温域では接着剤が基材に十分濡れ広がらず、さらに有機リン系化合物(C)とイミダゾール化合物(D)の存在下でも十分には反応が促進されないと推測される。イミダゾール化合物(D)が多すぎると余剰のイミダゾール化合物(D)が硬化塗膜に悪影響を及ぼしたり、ポットライフの短縮、接着剤の保存安定性低下を引き起こしたりするおそれがある。
The reason why the adhesive of the present invention is excellent in adhesive strength and electrolytic solution resistance even when aged at a particularly low temperature is not clear, but it is presumed as follows. Within the above viscosity range, the epoxy compound (B1) can be uniformly dispersed in the resin (A) in a solution state in the coating film during aging after the organic solvent (E) has been dried. The appropriate amount of the organophosphorus compound (C) and the imidazole compound (D) present here promotes the reaction between the acid group-containing resin (A1) and the curing agent (B) extremely preferably, and makes the electrolytic solution resistant. It is considered to be an excellent cured coating film.
On the other hand, if the viscosity is too low, the epoxy compound (B1) cannot be dispersed in the resin (A) and is unevenly distributed, and the acid group-containing resin (A1) cannot be appropriately crosslinked, which affects the adhesive strength and the electrolyte resistance. However, if the viscosity of the epoxy compound (B2) is too high, the adhesive will not spread sufficiently on the substrate in the low temperature range, and the reaction will be sufficient even in the presence of the organic phosphorus compound (C) and the imidazole compound (D). It is presumed that it will not be promoted. If the amount of the imidazole compound (D) is too large, the excess imidazole compound (D) may adversely affect the cured coating film, shorten the pot life, and reduce the storage stability of the adhesive.
(有機溶剤)
本発明の接着剤は、上記各成分に加え、さらに有機溶剤(E)を配合することにより流動性を確保し、適正な塗工性を発現させることができる。このような有機溶剤(E)としては、接着剤塗工時の乾燥工程における過熱により揮発させて除去できるものであれば特に限定されず、例えば、トルエン、キシレン等の芳香族系有機溶剤;n−ヘキサン、n−ヘプタン等の脂肪族系有機溶剤;シクロヘキサン、メチルシクロヘキサン等の脂環族系有機溶剤;トリクロロエチレン、ジクロロエチレン、クロロベンゼン、クロロホルム等のハロゲン系有機溶剤;メチルエチルケトン、メチルイソブチルケトン、シクロヘキサノンなどのケトン系溶剤;酢酸エチル、酢酸ブチル等のエステル系溶剤;エタノール、メタノール、n−プロパノール、2−プロパノール(イソプロピルアルコール)、ブタノール、ヘキサノール等のアルコール系溶剤;ジイソプロピルエーテル、ブチルセロソルブ、テトラヒドロフラン、ジオキサン、ブチルカルビトール等のエーテル系溶剤;ジエチレングリコールモノメチルエーテル、トリエチレングルコールモノメチルエーテル、プロピレングリコールモノメチルエーテル等のグリコールエーテル系溶剤;エチレングリコールモノメチルエーテルアセテート、プロプレングリコールモノメチルエーテルアセテート、ジエチレングリコールモノエチルエーテルアセテート等のグリコールエステル系溶剤等が挙げられ、これらは単独で使用しても良いし、2種以上を併用しても良い。
(Organic solvent)
The adhesive of the present invention can secure fluidity and exhibit appropriate coatability by further blending an organic solvent (E) in addition to the above components. The organic solvent (E) is not particularly limited as long as it can be volatilized and removed by overheating in the drying step at the time of coating the adhesive. For example, an aromatic organic solvent such as toluene or xylene; n An aliphatic organic solvent such as −hexane and n-heptane; an alicyclic organic solvent such as cyclohexane and methylcyclohexane; a halogen organic solvent such as trichloroethylene, dichloroethylene, chlorobenzene and chloroform; and methylethylketone, methylisobutylketone and cyclohexanone. Ketone solvent; ester solvent such as ethyl acetate, butyl acetate; alcohol solvent such as ethanol, methanol, n-propanol, 2-propanol (isopropyl alcohol), butanol, hexanol; diisopropyl ether, butyl cellosolve, tetrahydrofuran, dioxane, butyl Ether-based solvents such as carbitol; glycol ether-based solvents such as diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, and propylene glycol monomethyl ether; ethylene glycol monomethyl ether acetate, proprene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate, etc. Examples thereof include glycol ester-based solvents, and these may be used alone or in combination of two or more.
酸基含有樹脂(A1)の溶解性に優れることから、脂環族系有機溶剤と、エステル系溶剤との混合溶媒を用いることが好ましい。特に、酸基含有樹脂(A1)として酸基又は酸無水物基を有するオレフィン樹脂を用いた場合にはその溶解性に優れることからメチルシクロヘキサンと酢酸エチルとの混合溶媒を用いることが好ましい。さらに酸基含有樹脂(A1)の溶解性を向上させるために脂環族系有機溶剤と、エステル系溶剤と、アルコール系溶剤の混合溶媒を用いてもよい。このとき、アルコール系溶剤としてはイソプロピルアルコールや2−ブタノール等が好ましい。 Since the acid group-containing resin (A1) is excellent in solubility, it is preferable to use a mixed solvent of an alicyclic organic solvent and an ester solvent. In particular, when an olefin resin having an acid group or an acid anhydride group is used as the acid group-containing resin (A1), it is preferable to use a mixed solvent of methylcyclohexane and ethyl acetate because of its excellent solubility. Further, in order to improve the solubility of the acid group-containing resin (A1), a mixed solvent of an alicyclic organic solvent, an ester solvent and an alcohol solvent may be used. At this time, the alcohol solvent is preferably isopropyl alcohol, 2-butanol or the like.
また、エポキシ化合物(B1)の溶解性を向上させるために、脂環族系有機溶剤と、エステル系溶剤との混合溶媒に、さらに芳香族系有機溶剤やケトン系溶剤を併用してもよい。このとき、芳香族系有機溶剤としてはトルエンが好ましく挙げられ、ケトン系溶剤としてはメチルエチルケトンが好ましく挙げられる。 Further, in order to improve the solubility of the epoxy compound (B1), an aromatic organic solvent or a ketone solvent may be used in combination with the mixed solvent of the alicyclic organic solvent and the ester solvent. At this time, toluene is preferably mentioned as the aromatic organic solvent, and methyl ethyl ketone is preferably mentioned as the ketone solvent.
有機溶剤(E)の使用量としては、樹脂(A)と有機溶剤(E)との合計質量に対する、樹脂(A)の割合が5〜30質量%となる割合であることが好ましい。これにより、塗工性、金属フィルムへの濡れ性に優れた接着剤とすることができる。 The amount of the organic solvent (E) used is preferably such that the ratio of the resin (A) to the total mass of the resin (A) and the organic solvent (E) is 5 to 30% by mass. This makes it possible to obtain an adhesive having excellent coatability and wettability to a metal film.
本発明の接着剤は、必要に応じて酸無水物、接着促進剤、粘着付与剤、可塑剤、熱可塑性エラストマー、反応性エラストマー、リン酸化合物、シランカップリング剤等の各種添加剤を用いることができる。これらの添加剤の含有量は、本発明の接着剤の機能を損なわない範囲内で適宜調整すればよい。 As the adhesive of the present invention, various additives such as acid anhydride, adhesion accelerator, tackifier, plasticizer, thermoplastic elastomer, reactive elastomer, phosphoric acid compound, silane coupling agent and the like are used as needed. Can be done. The content of these additives may be appropriately adjusted within a range that does not impair the function of the adhesive of the present invention.
酸無水物としては、環状脂肪族酸無水物、芳香族酸無水物、不飽和カルボン酸無水物等が挙げられ、1種または2種以上を組み合わせて用いることができる。より具体的には、例えば、フタル酸無水物、トリメリット酸無水物、ピロメリット酸無水物、ベンゾフェノンテトラカルボン酸無水物、ドデセニルコハク酸無水物、ポリアジピン酸無水物、ポリアゼライン酸無水物、ポリセバシン酸無水物、ポリ(エチルオクタデカン二酸)無水物、ポリ(フェニルヘキサデカン二酸)無水物、テトラヒドロフタル酸無水物、メチルテトラヒドロフタル酸無水物、メチルヘキサヒドロフタル酸無水物、ヘキサヒドロフタル酸無水物、メチルハイミック酸無水物、トリアルキルテトラヒドロフタル酸無水物、メチルシクロヘキセンジカルボン酸無水物、メチルシクロヘキセンテトラカルボン酸無水物、エチレングリコールビストリメリテート二無水物、ヘット酸無水物、ナジック酸無水物、メチルナジック酸無水物、5−(2,5−ジオキソテトラヒドロ−3−フラニル)−3−メチル−3−シクロヘキサン−1,2−ジカルボン酸無水物、3,4−ジカルボキシ−1,2,3,4−テトラヒドロ−1−ナフタレンコハク酸二無水物、1−メチル−ジカルボキシ−1,2,3,4−テトラヒドロ−1−ナフタレンコハク酸二無水物等が挙げられる。 Examples of the acid anhydride include cyclic aliphatic acid anhydride, aromatic acid anhydride, unsaturated carboxylic acid anhydride and the like, and one type or a combination of two or more types can be used. More specifically, for example, phthalic anhydride, trimellitic anhydride, pyromellitic anhydride, benzophenone tetracarboxylic acid anhydride, dodecenyl succinic anhydride, polyazipic acid anhydride, polyazereic acid anhydride, polysevacinic acid. Anhydrous, poly (ethyloctadecanedioic acid) anhydride, poly (phenylhexadecanedioic acid) anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride , Methyl hymic acid anhydride, trialkyltetrahydrophthalic acid anhydride, methylcyclohexene dicarboxylic acid anhydride, methylcyclohexene tetracarboxylic acid anhydride, ethylene glycol bistrimericate dianhydride, het acid anhydride, nadic acid anhydride, Methylnadic acid anhydride, 5- (2,5-dioxotetrahydro-3-furanyl) -3-methyl-3-cyclohexane-1,2-dicarboxylic acid anhydride, 3,4-dicarboxy-1,2, Examples thereof include 3,4-tetrahydro-1-naphthalene succinic anhydride, 1-methyl-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic anhydride and the like.
また、酸無水物として上述した化合物をグリコールで変性したものを用いてもよい。変性に用いることができるグリコールとしては、エチレングリコール、プロピレングリコール、ネオペンチルグリコール等のアルキレングリコール類;ポリエチレングリコール、ポリプロピレングリコール、ポチテトラメチレンエーテルグリコール等のポリエーテルグリコール類等が挙げられる。更には、これらのうちの2種類以上のグリコール及び/又はポリエーテルグリコールの共重合ポリエーテルグリコールを用いることもできる。 Moreover, you may use the above-mentioned compound modified with glycol as an acid anhydride. Examples of glycols that can be used for modification include alkylene glycols such as ethylene glycol, propylene glycol and neopentyl glycol; and polyether glycols such as polyethylene glycol, polypropylene glycol and potitetramethylene ether glycol. Furthermore, copolymerized polyether glycols of two or more kinds of these glycols and / or polyether glycols can also be used.
酸無水物の配合量は、樹脂(A)100質量部に対して0.01質量部以上であることが好ましく、0.8質量部以上であることがより好ましい。また、酸無水物の配合量は、樹脂(A)100質量部に対して10質量部以下であることが好ましく、8質量部以下であることがより好ましく、1.5質量部以下であることがより好ましい。これにより、接着剤と金属との密着性が向上し、初期接着強度やヒートシール後の接着強度に優れた接着剤とすることができる。 The blending amount of the acid anhydride is preferably 0.01 part by mass or more, and more preferably 0.8 part by mass or more with respect to 100 parts by mass of the resin (A). The blending amount of the acid anhydride is preferably 10 parts by mass or less, more preferably 8 parts by mass or less, and 1.5 parts by mass or less with respect to 100 parts by mass of the resin (A). Is more preferable. As a result, the adhesiveness between the adhesive and the metal is improved, and it is possible to obtain an adhesive having excellent initial adhesive strength and adhesive strength after heat sealing.
酸無水物を用いることにより接着剤が接着性、耐熱性に優れる理由は定かではないが、次のように推測される。酸無水物は極性基を備え、金属基材への親和性に優れる。また、比較的分子量が小さいために、相対的に移動が容易である。塗工した接着剤が完全に硬化するまでに間に金属基材側に移動し、いわゆるアンカー剤のような役割を果たすことで接着性、耐熱性の向上に寄与していると考えられる。 The reason why the adhesive is excellent in adhesiveness and heat resistance by using the acid anhydride is not clear, but it is presumed as follows. The acid anhydride has a polar group and has an excellent affinity for a metal substrate. Moreover, since the molecular weight is relatively small, it is relatively easy to move. It is considered that the applied adhesive moves to the metal base material side before it is completely cured and plays a role like a so-called anchoring agent, thereby contributing to the improvement of adhesiveness and heat resistance.
接着促進剤としては、トリエチルアミン、トリエチレンジアミン、N’−メチル−N−(2−ジメチルアミノエチル)ピペラジン、1,8−ジアザビシクロ[5.4.0]ウンデセン(DBU)、1,5−ジアザビシクロ[4.3.0]−ノネン、6−ジブチルアミノ−1,8−ジアザビシクロ[5.4.0]ウンデセン、下記構造式(5)〜(15)で表される化合物等の3級アミン類及びこれら3級アミン類をフェノール、オクチル酸、4級化テトラフェニルボレート塩等でアミン塩にした化合物、トリアリルスルホニウムヘキサフルオロアンチモネート、ジアリルヨードニウムヘキサフルオロアンチモネート等のカチオン触媒などが挙げられる。これらは単独で使用しても良いし、2種以上を併用しても良い。なお下記構造式(5)〜(15)において炭素原子に結合している水素原子は省略されている。 Adhesion promoters include triethylamine, triethylenediamine, N'-methyl-N- (2-dimethylaminoethyl) piperazine, 1,8-diazabicyclo [5.4.0] undecene (DBU), 1,5-diazabicyclo [ 4.3.0] -Nonene, 6-dibutylamino-1,8-diazabicyclo [5.4.0] undecene, tertiary amines such as compounds represented by the following structural formulas (5) to (15) and Examples thereof include compounds obtained by converting these tertiary amines into amine salts with phenol, octyl acid, quaternized tetraphenylborate salt and the like, and cationic catalysts such as triarylsulfonium hexafluoroantimonate and diallyliodonium hexafluoroantimonate. These may be used alone or in combination of two or more. In the following structural formulas (5) to (15), the hydrogen atom bonded to the carbon atom is omitted.
粘着付与剤としては、例えば、ロジン系又はロジンエステル系粘着付与剤、テルペン系又はテルペンフェノール系粘着付与剤、飽和炭化水素樹脂、クマロン系粘着付与剤、クマロンインデン系粘着付与剤、スチレン樹脂系粘着付与剤、キシレン樹脂系粘着付与剤、フェノール樹脂系粘着付与剤、石油樹脂系粘着付与剤などが挙げられる。これらはそれぞれ単独で用いても良いし、二種類以上を併用しても良い。 Examples of the tackifier include a rosin-based or rosin ester-based tackifier, a terpene-based or terpene-phenol-based tackifier, a saturated hydrocarbon resin, a kumaron-based tackifier, a kumaron-inden-based tackifier, and a styrene resin-based tackifier. Examples thereof include a tackifier, a xylene resin-based tackifier, a phenol resin-based tackifier, and a petroleum resin-based tackifier. Each of these may be used alone, or two or more types may be used in combination.
可塑剤としては、ポリイソプレン、ポリブテン、プロセルオイル等が挙げられ、熱可塑性エラストマーとしてはスチレン・ブタジエン共重合物(SBS)、スチレン・ブタジエン共重合の水素添加物(SEBS)、SBBS、スチレン・イソプレン共重合の水素添加物(SEPS)、スチレンブロック共重合体(TPS)、オレフィン系エラストマー(TPO)等が、反応性エラストマーはこれらのエラストマーを酸変性したものが挙げられる。 Examples of the plasticizer include polyisoprene, polybutene, procel oil and the like, and examples of the thermoplastic elastomer include a styrene-butadiene copolymer (SBS), a hydrogenated product of a styrene-butadiene copolymer (SEBS), SBBS, and a styrene-isoprene. Examples of the copolymerized hydrogen additive (SEPS), styrene block copolymer (TPS), olefin elastomer (TPO) and the like are examples of the reactive elastomer obtained by acid-modifying these elastomers.
リン酸化合物としては、例えば次亜リン酸、亜リン酸、オルトリン酸、次リン酸等のリン酸類、例えばメタリン酸、ピロリン酸、トリポリリン酸、ポリリン酸、ウルトラリン酸等の縮合リン酸類、例えばオルトリン酸モノメチル、オルトリン酸モノエチル、オルトリン酸モノプロピル、オルトリン酸モノブチル、オルトリン酸モノ−2−エチルヘキシル、オルトリン酸モノフェニル、亜リン酸モノメチル、亜リン酸モノエチル、亜リン酸モノプロピル、亜リン酸モノブチル、亜リン酸モノ−2−エチルヘキシル、亜リン酸モノフェニル、オルトリン酸ジ−2−エチルヘキシル、オルトリン酸ジフェニル亜リン酸ジメチル、亜リン酸ジエチル、亜リン酸ジプロピル、亜リン酸ジブチル、亜リン酸ジ−2−エチルヘキシル、亜リン酸ジフェニル等のモノ、ジエステル化物、縮合リン酸とアルコール類とからのモノ、ジエステル化物、例えば前記のリン酸類に、例えばエチレンオキシド、プロピレンオキシド等のエポキシ化合物を付加させたもの、例えば脂肪族又は芳香族のジグリシジルエーテルに前記のリン酸類を付加させて得られるエポキシリン酸エステル類等が挙げられる。 Examples of the phosphoric acid compound include phosphoric acids such as hypophosphoric acid, phosphoric acid, orthophosphoric acid and hypophosphoric acid, and condensed phosphoric acids such as metaphosphoric acid, pyrophosphoric acid, tripolyphosphoric acid, polyphosphoric acid and ultraphosphoric acid, for example. Monomethyl orthophosphate, monoethyl orthophosphate, monopropyl orthophosphate, monobutyl orthophosphate, mono-2-ethylhexyl orthophosphate, monophenyl orthophosphate, monomethyl phosphite, monoethyl phosphite, monopropyl phosphite, monobutyl phosphite , Mono-2-ethylhexyl phosphite, monophenyl phosphite, di-2-ethylhexyl orthophosphate, dimethyl diphenyl phosphite, diethyl phosphite, dipropyl phosphite, dibutyl phosphite, phosphite Monos such as di-2-ethylhexyl and diphenyl phosphite, diesterates, monos from condensed phosphoric acid and alcohols, diesterates, for example, the above phosphoric acids are added with epoxy compounds such as ethylene oxide and propylene oxide. Examples thereof include epoxy phosphoric acid esters obtained by adding the above-mentioned phosphoric acids to an aliphatic or aromatic diglycidyl ether.
シランカップリング剤としては例えば、γ−アミノプロピルトリエトキシシラン、γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)−γ−アミノプロピルトリメトキシシラン、N−β(アミノエチル)−γ−アミノプロピルトリメチルジメトキシシラン、N−フェニル−γ−アミノプロピルトリメトキシシラン等のアミノシラン;β−(3,4−エポキシシクロヘキシル)エチルトリメトキシシラン、γ−グリシドキシプロピルトリメトキシシラン、γ−グリシドキシプロピルトリエトキシシラン等のエポキシシラン;ビニルトリス(β−メトキシエトキシ)シラン、ビニルトリエトキシシラン、ビニルトリメトキシシラン、γ−メタクリロキシプロピルトリメトキシシラン等のビニルシラン;ヘキサメチルジシラザン、γ−メルカプトプロピルトリメトキシシラン等を挙げることが出来る。 Examples of the silane coupling agent include γ-aminopropyltriethoxysilane, γ-aminopropyltrimethoxysilane, N-β (aminoethyl) -γ-aminopropyltrimethoxysilane, and N-β (aminoethyl) -γ-. Aminosilanes such as aminopropyltrimethyldimethoxysilane, N-phenyl-γ-aminopropyltrimethoxysilane; β- (3,4-epoxycyclohexyl) ethyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycid Epoxysilanes such as xypropyltriethoxysilane; vinylsilanes such as vinyltris (β-methoxyethoxy) silane, vinyltriethoxysilane, vinyltrimethoxysilane, γ-methacryloxypropyltrimethoxysilane; hexamethyldisilazane, γ-mercaptopropyl Examples thereof include trimethoxysilane.
上述した各成分を混合することにより本発明の接着剤を調整することができる。この際、各成分は同時に混合して接着剤としてもよいし、例えば硬化剤(B)以外の成分を予め混合してプレミクスチャーを調整しておき、接着剤の使用時に硬化剤(B)を混合する2液型、樹脂(A)を主成分とする第1剤と、硬化剤(B)を主成分とする第2剤と、その他の成分(例えば有機リン系化合物(C)とイミダゾール化合物(D))を含む第3剤とを接着剤の使用直前に混合して用いる3液型(あるいはそれ以上)の接着剤とすることが接着剤の安定性、作業性に優れることから好ましい。本明細書では2液型接着剤、3液型(あるいはそれ以上)接着剤を総称して多液型接着剤とする。 The adhesive of the present invention can be prepared by mixing each of the above-mentioned components. At this time, each component may be mixed at the same time to form an adhesive. For example, components other than the curing agent (B) may be mixed in advance to adjust the premixure, and the curing agent (B) may be used when the adhesive is used. A two-component type to be mixed, a first agent containing a resin (A) as a main component, a second agent containing a curing agent (B) as a main component, and other components (for example, an organic phosphorus compound (C) and an imidazole compound). It is preferable to use a third agent containing (D)) as a three-component (or more) adhesive mixed immediately before the use of the adhesive because the adhesive is excellent in stability and workability. In the present specification, two-component adhesives and three-component (or more) adhesives are collectively referred to as multi-component adhesives.
本発明の接着剤は、オレフィン樹脂のような非極性の基材と金属基材との接着性、耐熱性に優れる。 The adhesive of the present invention is excellent in adhesiveness and heat resistance between a non-polar substrate such as an olefin resin and a metal substrate.
<積層体>
本発明の積層体は、第1の基材と、第2の基材と、第1の基材と第2の基材との間に配置され、第1の基材と第2の基材とを貼り合せる接着層とを含む。接着層は、上述した接着剤の硬化塗膜である。第1の基材、第2の基材に加えてさらに他の基材を含んでいてもよい。第1の基材と他の基材、第2の基材と他の基材とを貼り合せる接着層は、本発明の接着剤の硬化塗膜であってもよいし、そうでなくてもよい。
<Laminated body>
The laminate of the present invention is arranged between the first base material, the second base material, the first base material and the second base material, and the first base material and the second base material are arranged. Includes an adhesive layer to bond with. The adhesive layer is a cured coating film of the above-mentioned adhesive. In addition to the first base material and the second base material, other base materials may be contained. The adhesive layer for bonding the first base material to the other base material and the second base material to the other base material may or may not be a cured coating film of the adhesive of the present invention. Good.
第1の基材、第2の基材、他の基材としては、例えば、紙、オレフィン系樹脂、アクリロニトリル−ブタジエン−スチレン共重合体(ABS樹脂)、ポリ塩化ビニル系樹脂、フッ素系樹脂、ポリ(メタ)アクリル系樹脂、カーボネート系樹脂、ポリアミド系樹脂、ポリイミド系樹脂、ポリフェニレンエーテル系樹脂、ポリフェニレンスルフィド系樹脂やポリエステル系樹脂から得られた合成樹脂フィルム、銅箔、アルミニウム箔の様な金属箔等を用いることが出来る。 Examples of the first base material, the second base material, and other base materials include paper, olefin resin, acrylonitrile-butadiene-styrene copolymer (ABS resin), polyvinyl chloride resin, and fluororesin. Metals such as poly (meth) acrylic resin, carbonate resin, polyamide resin, polyimide resin, polyphenylene ether resin, synthetic resin film obtained from polyphenylene sulfide resin or polyester resin, copper foil, aluminum foil Foil or the like can be used.
本発明の接着剤は、オレフィン樹脂のような非極性の基材と、金属基材との接着性に優れるため、第1の基材と第2の基材のうち一方が非極性の基材であり、他方が金属基材であることが好ましいが、これに限定されない。 Since the adhesive of the present invention has excellent adhesiveness between a non-polar base material such as an olefin resin and a metal base material, one of the first base material and the second base material is a non-polar base material. The other is preferably, but is not limited to, a metal base material.
本発明の積層体は、第1の基材と第2の基材の一方に本発明の接着剤を塗布し、次いで他方を積層し、接着剤を硬化させて得られる。接着剤を塗布した後、第1の基材と第2の基材とを積層するまでの間に乾燥工程を設けることが好ましい。
接着剤の塗工方式としては、グラビアコーター方式、マイクログラビアコーター方式、リバースコーター方式、バーコーター方式、ロールコーター方式、ダイコーター方式等を用いることが出来る。接着剤の塗布量は、乾燥後の塗布重量が0.5〜20.0g/m2となるよう調整することが好ましい。0.5g/m2を下回ると連続均一塗布性が低下し易くなり、20.0g/m2を上回ると塗布後における溶剤離脱性も低下し、作業性の低下や残留溶剤の問題が生じ易くなる。
The laminate of the present invention is obtained by applying the adhesive of the present invention to one of the first base material and the second base material, then laminating the other, and curing the adhesive. It is preferable to provide a drying step between the application of the adhesive and the laminating of the first base material and the second base material.
As the adhesive coating method, a gravure coater method, a microgravure coater method, a reverse coater method, a bar coater method, a roll coater method, a die coater method and the like can be used. The amount of the adhesive applied is preferably adjusted so that the applied weight after drying is 0.5 to 20.0 g / m 2 . If it is less than 0.5 g / m 2 , the continuous uniform coating property is likely to be lowered, and if it is more than 20.0 g / m 2 , the solvent releasability after coating is also lowered, and the workability is easily lowered and the problem of residual solvent is likely to occur. Become.
第1の基材と第2の基材とを積層する際のラミネートロールの温度は25〜120℃、圧力は3〜300kg/cm2であることが好ましい。
第1の基材と第2の基材とを貼り合せた後、エージング工程を設けることが好ましい。エージング条件は、25〜100℃、12〜240時間であることが好ましい。
The temperature of the laminating roll when laminating the first base material and the second base material is preferably 25 to 120 ° C., and the pressure is preferably 3 to 300 kg / cm 2 .
It is preferable to provide an aging step after laminating the first base material and the second base material. The aging conditions are preferably 25 to 100 ° C. and 12 to 240 hours.
特に、本発明の接着剤はエージング温度が60℃以下、さらには55℃以下と通常の酸とエポキシの反応温度よりも相当に低い場合にも優れた効果を発揮し、良好な初期接着強度、耐電解液性を示す。60℃以下でエージングを行う場合は、エージング時間は24時間以上であることが好ましい。エージング時間の上限は特に限定されないが、168時間程度で十分な効果を発揮する。エージング温度とエージング時間のバランスの観点からは、40〜60℃で24〜168時間でエージング工程を行うことが好ましい。 In particular, the adhesive of the present invention exerts an excellent effect even when the aging temperature is 60 ° C. or lower, further 55 ° C. or lower, which is considerably lower than the reaction temperature of a normal acid and epoxy, and has good initial adhesive strength. Shows electrolytic solution resistance. When aging is performed at 60 ° C. or lower, the aging time is preferably 24 hours or more. The upper limit of the aging time is not particularly limited, but a sufficient effect is exhibited in about 168 hours. From the viewpoint of the balance between the aging temperature and the aging time, it is preferable to carry out the aging step at 40 to 60 ° C. for 24 to 168 hours.
<電池用包装材>
本発明の電池用包装材は、一例として、第1の基材と、第2の基材と、第3の基材と、第1の基材と第2の基材を貼り合せる第1の接着層と、第2の基材と第3の基材とを貼り合せる第2の接着層とを含む。第1の基材はポリオレフィンフィルムであり、第2の基材は金属箔である。第3の基材はナイロン、ポリエステル等の樹脂フィルムである。第1の接着層は本発明の接着剤の硬化塗膜である。第2の接着層は本発明の接着剤の硬化塗膜であってもよいし、そうでなくてもよい。第3の基材の第2の接着層が設けられるのとは反対側に、さらに接着層を介して、または介さずに他の基材を配置してもよいし、コーティング層を設けてもよい。他の基材やコーティング層を設けなくてもよい。
<Battery packaging material>
As an example, the packaging material for a battery of the present invention has a first base material, a second base material, a third base material, a first base material, and a second base material bonded together. It includes an adhesive layer and a second adhesive layer for bonding the second base material and the third base material. The first base material is a polyolefin film, and the second base material is a metal foil. The third base material is a resin film such as nylon or polyester. The first adhesive layer is a cured coating film of the adhesive of the present invention. The second adhesive layer may or may not be a cured coating of the adhesive of the present invention. Another substrate may be placed on the opposite side of the third substrate from which the second adhesive layer is provided, with or without an adhesive layer, or a coating layer may be provided. Good. It is not necessary to provide another base material or coating layer.
ポリオレフィンフィルムとしては、従来から公知の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。無延伸フィルムであることが好ましい。ポリオレフィンフィルムの膜厚は、特に限定されないが、10μm以上であることが好ましく、20μm以上であることがより好ましく、25μm以上であることがさらに好ましい。また、100μm以下であることが好ましく、95μm以下であることがより好ましく、90μm以下であることがさらに好ましい。
第1の基材は、後述する電池を製造する際に、本発明の電池用包装材同士をヒートシールして貼り合せる際のシーラント層として機能する。
The polyolefin film may be appropriately selected from conventionally known olefin resins. For example, although not particularly limited, polyethylene, polypropylene, ethylene propylene copolymer and the like can be used. It is preferably a non-stretched film. The film thickness of the polyolefin film is not particularly limited, but is preferably 10 μm or more, more preferably 20 μm or more, and further preferably 25 μm or more. Further, it is preferably 100 μm or less, more preferably 95 μm or less, and further preferably 90 μm or less.
The first base material functions as a sealant layer when the battery packaging materials of the present invention are heat-sealed and bonded to each other when the battery described later is manufactured.
金属箔としては、アルミニウム、銅、ニッケル等が挙げられる。これらの金属箔は、サンドブラスト処理、研磨処理、脱脂処理、エッチング処理、防錆剤浸漬又はスプレーによる表面処理、3価クロム化成処理、リン酸塩化成処理、硫化物化成処理、陽極酸化被膜形成、フッ素樹脂コーティング等の表面処理を施したものであってもよい。これらのなかでも3価クロム化成処理を施したものが密着性保持性能(耐環境劣化性)、防食性に優れる点から好ましい。また、この金属フィルムの厚みは腐食防止の観点から10〜100μmの範囲であることが好ましい。 Examples of the metal foil include aluminum, copper, nickel and the like. These metal foils are sandblasted, polished, degreased, etched, surface-treated by rust preventive immersion or spraying, trivalent chromium chemical conversion treatment, phosphate chemical conversion treatment, sulfide chemical conversion treatment, anodic oxide film formation, etc. It may be surface-treated such as a fluororesin coating. Among these, those subjected to trivalent chromium chemical conversion treatment are preferable because they are excellent in adhesion retention performance (environmental deterioration resistance) and corrosion resistance. Further, the thickness of this metal film is preferably in the range of 10 to 100 μm from the viewpoint of corrosion prevention.
第3の基材として用いることができる樹脂フィルムとしては、ポリエステル樹脂、ポリアミド樹脂、エポキシ樹脂、アクリル樹脂、フッ素樹脂、ポリウレタン樹脂、珪素樹脂、フェノール樹脂、及びこれらの混合物や共重合物等の樹脂フィルムが挙げられる。これらの中でも、好ましくはポリエステル樹脂、ポリアミド樹脂が挙げられ、より好ましくは2軸延伸ポリエステル樹脂、2軸延伸ポリアミド樹脂が挙げられる。ポリエステル樹脂としては、具体的には、ポリエチレンテレフタレート、ポリブチレンテレフタレート、ポリエチレンナフタレート、ポリブチレンナフタレート、共重合ポリエステル、ポリカーボネート等が挙げられる。また、ポリアミド樹脂としては、具体的には、ナイロン6、ナイロン6,6、ナイロン6とナイロン6,6との共重合体、ナイロン6,10、ポリメタキシリレンアジパミド(MXD6)等が挙げられる。 Examples of the resin film that can be used as the third base material include polyester resin, polyamide resin, epoxy resin, acrylic resin, fluororesin, polyurethane resin, silicon resin, phenol resin, and resins such as mixtures and copolymers thereof. Film is mentioned. Among these, polyester resin and polyamide resin are preferable, and biaxially stretched polyester resin and biaxially stretched polyamide resin are more preferable. Specific examples of the polyester resin include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, polybutylene naphthalate, copolymerized polyester, and polycarbonate. Specific examples of the polyamide resin include nylon 6, nylon 6, 6, a copolymer of nylon 6 and nylon 6, 6, nylon 6, 10, and polymethoxylylen adipamide (MXD6). Be done.
コーティング層は、例えばポリ塩化ビニリデン、ポリエステル樹脂、ウレタン樹脂、アクリル樹脂、エポキシ樹脂などにより形成することができる。2液硬化型樹脂により形成することが好ましい。コーティング層を形成する2液硬化型樹脂としては、例えば、2液硬化型ウレタン樹脂、2液硬化型ポリエステル樹脂、2液硬化型エポキシ樹脂などが挙げられる。また、コーティング層には、マット化剤を配合してもよい。 The coating layer can be formed of, for example, polyvinylidene chloride, polyester resin, urethane resin, acrylic resin, epoxy resin, or the like. It is preferably formed of a two-component curable resin. Examples of the two-component curable resin forming the coating layer include a two-component curable urethane resin, a two-component curable polyester resin, and a two-component curable epoxy resin. Moreover, you may mix the matting agent in the coating layer.
マット化剤としては、例えば、粒径が0.5nm〜5μm程度の微粒子が挙げられる。マット化剤の材質については、特に制限されないが、例えば、金属、金属酸化物、無機物、有機物等が挙げられる。また、マット化剤の形状についても、特に制限されないが、例えば、球状、繊維状、板状、不定形、バルーン状等が挙げられる。マット化剤として、具体的には、タルク,シリカ,グラファイト、カオリン、モンモリロイド、モンモリロナイト、合成マイカ、ハイドロタルサイト、シリカゲル、ゼオライト、水酸化アルミニウム、水酸化マグネシウム、酸化亜鉛,酸化マグネシウム,酸化アルミニウム,酸化ネオジウム,酸化アンチモン、酸化チタン、酸化セリウム、硫酸カルシウム,硫酸バリウム、炭酸カルシウム,ケイ酸カルシウム、炭酸リチウム、安息香酸カルシウム,シュウ酸カルシウム,ステアリン酸マグネシウム、カーボンブラック、カーボンナノチューブ類、高融点ナイロン、架橋アクリル、架橋スチレン、架橋ポリエチレン、ベンゾグアナミン、金、アルミニウム、銅、ニッケル等が挙げられる。これらのマット化剤は、1種単独で使用してもよく、また2種以上を組み合わせて使用してもよい。これらのマット化剤の中でも、分散安定性やコスト等の観点から、好ましくはりシリカ、硫酸バリウム、酸化チタンが挙げられる。また、マット化剤には、表面に絶縁処理、高分散性処理等の各種表面処理を施しておいてもよい。 Examples of the matting agent include fine particles having a particle size of about 0.5 nm to 5 μm. The material of the matting agent is not particularly limited, and examples thereof include metals, metal oxides, inorganic substances, and organic substances. The shape of the matting agent is also not particularly limited, and examples thereof include a spherical shape, a fibrous shape, a plate shape, an amorphous shape, and a balloon shape. Specific examples of the matting agent include talc, silica, graphite, kaolin, montmoriloid, montmorillonite, synthetic mica, hydrotalcite, silica gel, zeolite, aluminum hydroxide, magnesium hydroxide, zinc oxide, magnesium oxide, and aluminum oxide. , Neodium oxide, Antimon oxide, Titanium oxide, Serium oxide, Calcium sulfate, Barium sulfate, Calcium carbonate, Calcium silicate, Lithium carbonate, Calcium benzoate, Calcium silicate, Magnesium stearate, Carbon black, Carbon nanotubes, High melting point Examples thereof include nylon, crosslinked acrylic, crosslinked styrene, crosslinked polyethylene, benzoguanamine, gold, aluminum, copper and nickel. These matting agents may be used alone or in combination of two or more. Among these matting agents, preferably silica, barium sulfate, and titanium oxide are mentioned from the viewpoint of dispersion stability and cost. Further, the matting agent may be subjected to various surface treatments such as an insulating treatment and a highly dispersible treatment on the surface.
このような積層体を、電池とした際に第1の基材であるポリオレフィンフィルムが第3の基材よりも内側になるようにして成型し、本発明の二次電池外装材となる。成型方法としては、特に制限はなく、一例として以下のような方法が挙げられる。 Such a laminate is molded so that the polyolefin film, which is the first base material, is inside the third base material when it is used as a battery, and becomes the secondary battery exterior material of the present invention. The molding method is not particularly limited, and examples thereof include the following methods.
・加熱圧空成型法:電池用包装材を高温、高圧のエアーが供給される孔を有する下型と、ポケット形状の凹部を有する上型に挟み、加熱軟化させながらエアーを供給して凹部を形成する方法。
・プレヒーター平板式圧空成型法:電池用包装材を加熱軟化させた後、高圧のエアーが供給される孔を有する下型と、ポケット形状の凹部を有する上型に挟み、エアーを供給して凹部を形成する方法。
・ドラム式真空成型法:電池用包装材を加熱ドラムで部分的に加熱軟化後、ポケット形状の凹部を有するドラムの該凹部を真空引きして凹部を成型する方法。
・ピン成型法:底材シートを加熱軟化後ポケット形状の凹凸金型で圧着する方法。
・プレヒータープラグアシスト圧空成型法:電池用包装材を加熱軟化させた後、高圧のエアーが供給される孔を有する下型と、ポケット形状の凹部を有する上型に挟み、エアーを供給して凹部を形成する方法であって、成型の際に、凸形状のプラグを上昇及び降下をさせて成型を補助する方法。
-Heat-compressed air molding method: The packaging material for batteries is sandwiched between a lower mold with holes for supplying high-temperature and high-pressure air and an upper mold with pocket-shaped recesses, and air is supplied while being heated and softened to form recesses. how to.
-Preheater flat plate type compressed air molding method: After heating and softening the packaging material for batteries, air is supplied by sandwiching it between a lower mold with holes for supplying high-pressure air and an upper mold with pocket-shaped recesses. A method of forming a recess.
-Drum type vacuum forming method: A method in which a battery packaging material is partially heated and softened with a heating drum, and then the concave portion of a drum having a pocket-shaped concave portion is evacuated to form the concave portion.
-Pin molding method: A method in which the bottom material sheet is heat-softened and then crimped with a pocket-shaped uneven mold.
-Preheater plug assist compressed air molding method: After heating and softening the packaging material for batteries, air is supplied by sandwiching it between a lower mold with holes for supplying high-pressure air and an upper mold with pocket-shaped recesses. A method of forming a concave portion, which assists molding by raising and lowering a convex plug at the time of molding.
成型後の底材の肉厚が均一であることから、加熱真空成型法であるプレヒータープラグアシスト圧空成型法が好ましい。
このようにして得られた本発明の電池用包装材は、正極、負極、電解質等の電池素子を密封して収容する電池用容器として好適に使用することができる。
Since the wall thickness of the bottom material after molding is uniform, the preheater plug assist compressed air molding method, which is a heating vacuum forming method, is preferable.
The battery packaging material of the present invention thus obtained can be suitably used as a battery container for sealing and accommodating battery elements such as a positive electrode, a negative electrode, and an electrolyte.
<電池>
本発明の電池は、正極、負極、及び電解質を備えた電池素子を、本発明の電池用包装材で、前記正極及び負極の各々に接続された金属端子が外側に突出させた状態で、電池素子の周縁にフランジ部(シーラント層同士が接触する領域)が形成できるようにして被覆し、前記フランジ部のシーラント層同士をヒートシールして密封させることによって得られる。
<Battery>
The battery of the present invention is a battery in which a battery element including a positive electrode, a negative electrode, and an electrolyte is projected outward from the metal terminals connected to each of the positive electrode and the negative electrode in the battery packaging material of the present invention. It is obtained by covering the peripheral edge of the element so that a flange portion (a region where the sealant layers come into contact with each other) can be formed, and heat-sealing the sealant layers of the flange portion with each other.
本発明の電池用包装材を用いて得られる電池としては、一次電池、二次電池のいずれであってもよいが、好ましくは二次電池である。二次電池としては特に制限されず、例えば、リチウムイオン電池、リチウムイオンポリマー電池、鉛蓄電池、ニッケル・水素蓄電池、ニッケル・カドミウム蓄電池、ニッケル・鉄蓄電池、ニッケル・亜鉛蓄電池、酸化銀・亜鉛蓄電池、金属空気電池、多価カチオン電池、コンデンサー、キャパシター等が挙げられる。これらの二次電池の中でも、本発明の電池用包装材の好適な適用対象として、リチウムイオン電池及びリチウムイオンポリマー電池が挙げられる。 The battery obtained by using the battery packaging material of the present invention may be either a primary battery or a secondary battery, but is preferably a secondary battery. The secondary battery is not particularly limited, and for example, a lithium ion battery, a lithium ion polymer battery, a lead storage battery, a nickel / hydrogen storage battery, a nickel / cadmium storage battery, a nickel / iron storage battery, a nickel / zinc storage battery, a silver oxide / zinc storage battery, etc. Examples thereof include metal air batteries, multivalent cation batteries, capacitors, and capacitors. Among these secondary batteries, lithium ion batteries and lithium ion polymer batteries can be mentioned as suitable application targets of the battery packaging material of the present invention.
以下、実施例と比較例により本発明を説明するが、本発明はこれに限定されるものではない。配合組成その他の数値は特記しない限り質量基準である。 Hereinafter, the present invention will be described with reference to Examples and Comparative Examples, but the present invention is not limited thereto. The composition and other values are based on mass unless otherwise specified.
<エポキシ化合物の合成>
(エポキシ化合物1の合成)
温度計、撹拌機を取り付けたフラスコにビスフェノールA228g(1.00モル)とトリエチレングリコールジビニルエーテル(ISP社製:商品名Rapi−Cure DVE−3)172g(0.85モル)を仕込み、120℃まで1時間要して昇温した後、さらに120℃で6時間反応させて透明半固形の変性多価フェノール類400gを得た。
得られた変性多価フェノール類(ph−1a)は、NMRスペクトル(13C)と、マススペクトルでn=1、n=2の理論構造に相当するM+=658,M+=1088のピークが得られたことから下記構造式Ep1’で表される構造をもつであることが確認された。変性多価フェノール類の水酸基当量は364g/eq.、粘度は40mPa・s(150℃,ICI粘度計)、水酸基当量より算出される下記構造式Ep1’中のmの平均値は、m≧1の成分で3.21、及びm≧0の成分で1.16であった。
<Synthesis of epoxy compounds>
(Synthesis of Epoxy Compound 1)
A flask equipped with a thermometer and a stirrer was charged with 228 g (1.00 mol) of bisphenol A and 172 g (0.85 mol) of triethylene glycol divinyl ether (manufactured by ISP: trade name Rapi-Cure DVE-3) at 120 ° C. After 1 hour to raise the temperature, the mixture was further reacted at 120 ° C. for 6 hours to obtain 400 g of transparent semi-solid modified polyhydric phenols.
The obtained modified polyhydric phenols (ph-1a) have peaks of M + = 658 and M + = 1088 corresponding to the theoretical structure of n = 1 and n = 2 in the NMR spectrum (13C) and the mass spectrum. Therefore, it was confirmed that the structure was represented by the following structural formula Ep1'. The hydroxyl equivalent of the modified polyhydric phenols is 364 g / eq. The viscosity is 40 mPa · s (150 ° C., ICI viscometer), and the average value of m in the following structural formula Ep1'calculated from the hydroxyl group equivalent is 3.21 for the component m ≧ 1 and the component m ≧ 0. It was 1.16.
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに得られた変性多価フェノール類400g(水酸基当量364g/eq.)、エピクロルヒドリン925g(10モル)、n−ブタノール185gを仕込み溶解させた。その後、窒素ガスパージを施しながら65℃に昇温した後に共沸する圧力までに減圧し、49%水酸化ナトリウム水溶液122g(1.5モル)を5時間かけて滴下した。滴下終了後0.5時間撹拌を続けた。この間、共沸で留出してきた留出分をディーンスタークトラップで分離して水層を除去し、有機層を反応系内に戻しながら反応させた。その後、未反応のエピクロルヒドリンを減圧蒸留して留去させた。得られた粗エポキシ樹脂にメチルイソブチルケトン1000gとn−ブタノール100gを加え溶解させ、更にこの溶液に10%水酸化ナトリウム水溶液20gを添加して80℃で2時間反応させた後に洗浄液のPHが中性となるまで水300gで水洗を3回繰り返した。次いで共沸によって系内を脱水し精密濾過を経た後に溶媒を減圧下で留去して透明液体のエポキシ化合物457gを得た。エポキシ化合物は、NMRスペクトル(13C)と、マススペクトルでn=1、n=2の理論構造に相当するM+=770,M+=1200のピークが得られたことから下記構造式Ep1で表される構造のエポキシ化合物1を含有することが確認された。 400 g (hydroxyl equivalent 364 g / eq.) Of modified polyhydric phenols, 925 g (10 mol) of epichlorohydrin, and 185 g of n-butanol obtained in a flask equipped with a thermometer, a dropping funnel, a cooling tube, and a stirrer were charged and dissolved. .. Then, the temperature was raised to 65 ° C. while purging with nitrogen gas, the pressure was reduced to an azeotropic pressure, and 122 g (1.5 mol) of a 49% sodium hydroxide aqueous solution was added dropwise over 5 hours. Stirring was continued for 0.5 hours after the completion of the dropping. During this period, the distillate distilled off by azeotrope was separated by a Dean-Stark trap to remove the aqueous layer, and the organic layer was reacted while being returned to the reaction system. Then, unreacted epichlorohydrin was distilled under reduced pressure and distilled off. To the obtained crude epoxy resin, 1000 g of methyl isobutyl ketone and 100 g of n-butanol were added and dissolved, and 20 g of a 10% aqueous sodium hydroxide solution was further added to this solution and reacted at 80 ° C. for 2 hours, after which the pH of the washing solution was medium. Washing with 300 g of water was repeated 3 times until it became sex. Then, the inside of the system was dehydrated by azeotropic filtration, and after microfiltration, the solvent was distilled off under reduced pressure to obtain 457 g of a transparent liquid epoxy compound. The epoxy compound is represented by the following structural formula Ep1 because peaks of M + = 770 and M + = 1200 corresponding to the theoretical structure of n = 1 and n = 2 were obtained in the NMR spectrum (13C) and the mass spectrum. It was confirmed that the epoxy compound 1 of the structure was contained.
得られたエポキシ化合物1は、上記構造式Ep1においてn=0の化合物と、n=1以上の化合物との混合物であり、GPCで確認したところ該混合物中n=0の化合物を20質量%の割合で含有するものであった。また、このエポキシ化合物1のエポキシ当量は462g/eq.、粘度は12000mPa・s(25℃,キャノンフェンスケ法)、エポキシ当量から算出される前記構造式Ea−1中のnの平均値は、n≧1の成分で2.97、及びn≧0の成分で1.35であった。 The obtained epoxy compound 1 is a mixture of a compound having n = 0 in the above structural formula Ep1 and a compound having n = 1 or more, and when confirmed by GPC, 20% by mass of the compound having n = 0 in the mixture was obtained. It was contained in proportion. The epoxy equivalent of this epoxy compound 1 is 462 g / eq. The viscosity is 12000 mPa · s (25 ° C., Canon Fenceke method), and the average value of n in the structural formula Ea-1 calculated from the epoxy equivalent is 2.97 for the component of n ≧ 1, and n ≧ 0. The component of was 1.35.
(エポキシ化合物2の合成)
温度計、撹拌機を取り付けたフラスコに1,6−ヘキサンジオールのジグリシジルエーテル(DIC株式会社製:商品名EPICLON 726D、エポキシ当量124g/eq)744g(6当量)とビスフェノールA(水酸基当量114g/eq)1368g(12当量)を仕込み、140℃まで30分間要して昇温した後、4%水酸化ナトリウム水溶液5gを仕込んだ。その後、30分間要して150℃まで昇温し、さらに150℃で3時間反応させた。その後、中和量のリン酸ソーダを添加し、ヒドロキシ化合物2090gを得た。NMRスペクトル(13C)、マススペクトルでoが1の理論構造に相当するM+=687、及びoが2の理論構造に相当するM+=1145のピークが得られたことから下記構造式(EP2’)で表される構造のヒドロキシ化合物を含有することが確認された。このヒドロキシ化合物のGPCより算出した水酸基当量は262g/eq、水酸基当量から算出した下記構造式(EP2’)中のoの平均値は0.6であった。
(Synthesis of Epoxy Compound 2)
Diglycidyl ether of 1,6-hexanediol (manufactured by DIC Co., Ltd .: trade name EPICLON 726D, epoxy equivalent 124 g / eq) 744 g (6 equivalents) and bisphenol A (hydroxyl equivalent 114 g /) in a flask equipped with a thermometer and a stirrer. 1368 g (12 equivalents) of eq) was charged, and the temperature was raised to 140 ° C. for 30 minutes, and then 5 g of a 4% sodium hydroxide aqueous solution was charged. Then, it took 30 minutes to raise the temperature to 150 ° C., and further reacted at 150 ° C. for 3 hours. Then, a neutralized amount of sodium phosphate was added to obtain 2090 g of a hydroxy compound. Since the peaks of M + = 687 corresponding to the theoretical structure of o in the NMR spectrum (13C) and the mass spectrum and M + = 1145 corresponding to the theoretical structure of o of 2 were obtained, the following structural formula (EP2) was obtained. It was confirmed that it contained a hydroxy compound having a structure represented by'). The hydroxyl group equivalent calculated from GPC of this hydroxy compound was 262 g / eq, and the average value of o in the following structural formula (EP2') calculated from the hydroxyl group equivalent was 0.6.
温度計、滴下ロート、冷却管、撹拌機を取り付けたフラスコに上記で得られたヒドロキシ化合物261g(水酸基当量261g/eq.)、エピクロルヒドリン1110g(12モル)、n−ブタノール222gを仕込み溶解させた。その後、窒素ガスパージを施しながら、65℃に昇温した後に、共沸する圧力までに減圧して、49%水酸化ナトリウム水溶液122g(1.5モル)を5時間かけて滴下した。次いでこの条件下で0.5時間撹拌を続けた。この間、共沸で留出してきた留出分をディーンスタークトラップで分離して、水層を除去し、有機層を反応系内に戻しながら反応した。その後、未反応のエピクロルヒドリンを減圧蒸留して留去させた。得られた粗エポキシ樹脂にメチルイソブチルケトン1000gとn−ブタノール100gを加え溶解した。更にこの溶液に10%水酸化ナトリウム水溶液20gを添加して80℃で2時間反応させた後に洗浄液のPHが中性となるまで水300gで水洗を3回繰り返した。次いで共沸によって系内を脱水し精密濾過を経た後に溶媒を減圧下で留去して380gの液状のエポキシ化合物2を得た。このエポキシ化合物2は、NMRスペクトル(13C)、マススペクトルからp=1、q=1、r=0の理論構造に相当するM+=798、p=2、q=2、r=0の理論構造に相当するM+=1257のピークが得られたことから下記構造式(Ep2)で表される構造のエポキシ化合物2を含有することが確認された。得られたエポキシ化合物2は、下記構造式(Ep2)においてp=0、q=0、r=0の化合物を含んでおり、GPCで確認したところ該混合物中p=0、q=0、r=0の化合物を29重量%の割合で含有するものであった。また、このエポキシ化合物2のエポキシ当量は350g/eq.、粘度は2000Pa・s(25℃,E型粘度法)、エポキシ当量から算出される下記構造式(Ep2)中のrの平均値は0.1であった。 261 g (hydroxyl equivalent 261 g / eq.) Of the hydroxy compound obtained above, 1110 g (12 mol) of epichlorohydrin, and 222 g of n-butanol were charged and dissolved in a flask equipped with a thermometer, a dropping funnel, a cooling tube, and a stirrer. Then, while performing nitrogen gas purging, the temperature was raised to 65 ° C., the pressure was reduced to an azeotropic pressure, and 122 g (1.5 mol) of a 49% sodium hydroxide aqueous solution was added dropwise over 5 hours. Then, stirring was continued for 0.5 hours under this condition. During this period, the distillate distilled off by azeotrope was separated by a Dean-Stark trap, the aqueous layer was removed, and the organic layer was returned to the reaction system for reaction. Then, unreacted epichlorohydrin was distilled under reduced pressure and distilled off. To the obtained crude epoxy resin, 1000 g of methyl isobutyl ketone and 100 g of n-butanol were added and dissolved. Further, 20 g of a 10% aqueous sodium hydroxide solution was added to this solution and reacted at 80 ° C. for 2 hours, and then washing with water was repeated 3 times with 300 g of water until the pH of the washing liquid became neutral. Then, the inside of the system was dehydrated by azeotrope, and after undergoing microfiltration, the solvent was distilled off under reduced pressure to obtain 380 g of liquid epoxy compound 2. This epoxy compound 2 has a theoretical structure of M + = 798, p = 2, q = 2, r = 0, which corresponds to the theoretical structure of p = 1, q = 1, r = 0 from the NMR spectrum (13C) and the mass spectrum. Since the peak of M + = 1257 corresponding to the above was obtained, it was confirmed that the epoxy compound 2 having the structure represented by the following structural formula (Ep2) was contained. The obtained epoxy compound 2 contains a compound having p = 0, q = 0, r = 0 in the following structural formula (Ep2), and when confirmed by GPC, p = 0, q = 0, r in the mixture. The compound containing = 0 was contained in a proportion of 29% by weight. The epoxy equivalent of this epoxy compound 2 is 350 g / eq. The viscosity was 2000 Pa · s (25 ° C., E-type viscosity method), and the average value of r in the following structural formula (Ep2) calculated from the epoxy equivalent was 0.1.
<接着剤の調整>
(実施例1)
トーヨータックPMA−KE:100部、トリフェニルホスフィン:0.04部、キュアゾール2E4MZ:0.06部、jERキュアYH306:1部を混合溶媒(シクロメチルヘキサン/酢酸エチル=71/8)に溶解させ、不揮発分20%にした。次いでEPICLON TSR−960を5.0部加え、よく攪拌して実施例1の接着剤を調製した。
<Adhesive adjustment>
(Example 1)
Toyotac PMA-KE: 100 parts, triphenylphosphine: 0.04 parts, curesol 2E4MZ: 0.06 parts, jER cure YH306: 1 part are dissolved in a mixed solvent (cyclomethylhexane / ethyl acetate = 71/8). , The non-volatile content was set to 20%. Next, 5.0 parts of EPICLON TSR-960 was added and stirred well to prepare the adhesive of Example 1.
(実施例2〜5)
表2に記載の配合に変更した以外は実施例1と同様にして実施例2〜5の接着剤を調整した。
(比較例1〜4)
表3に記載の配合に変更した以外は実施例1と同様にして比較例1〜4の接着剤を調整した。
(Examples 2 to 5)
The adhesives of Examples 2 to 5 were adjusted in the same manner as in Example 1 except that the formulations shown in Table 2 were changed.
(Comparative Examples 1 to 4)
The adhesives of Comparative Examples 1 to 4 were prepared in the same manner as in Example 1 except that the formulations shown in Table 3 were changed.
なお、実施例、比較例で用いた化合物の詳細は以下の通りである。
トーヨータックPMA−KE:無水マレイン酸変性オレフィン樹脂、酸価:44mgKOH/g、融点:80℃、東洋紡社製
キュアゾール2E4MZ:2−エチル−4−メチル−イミダゾール、四国化成工業株式会社
jERキュアYH−306:トリアルキルテトラヒドロ無水フタル酸、三菱化学社製
EPICLON TSR−960:無溶剤型ゴム変性エポキシ樹脂、DIC株式会社製
DENALEX FCA−061L:ポリブタジエン型エポキシ樹脂、ナガセケムテックス株式会社製
The details of the compounds used in Examples and Comparative Examples are as follows.
Toyo Tuck PMA-KE: Maleic anhydride-modified olefin resin, acid value: 44 mgKOH / g, melting point: 80 ° C., Toyobo Curesol 2E4MZ: 2-ethyl-4-methyl-imidazole, Shikoku Kasei Kogyo Co., Ltd. jER Cure YH- 306: Trialkyltetrahydromaleic anhydride, EPICLON TSR-960 manufactured by Mitsubishi Chemical Corporation, solvent-free rubber-modified epoxy resin, DENALEX FCA-061L manufactured by DIC Corporation, polybutadiene type epoxy resin, manufactured by Nagase ChemteX Corporation
実施例、比較例で用いたエポキシ化合物の52℃における粘度を表1に示す。エポキシ化合物の粘度は測定装置としてBROOKFIELD R/S Plus RHEOMETERを用い、治具としてC50−1を用い、52℃にて測定した。 Table 1 shows the viscosities of the epoxy compounds used in Examples and Comparative Examples at 52 ° C. The viscosity of the epoxy compound was measured at 52 ° C. using BROOKFIELD R / S Plus RHEOMETER as a measuring device and C50-1 as a jig.
オレフィン樹脂の酸価は、FT−IR(日本分光社製、FT−IR4200)を使用し、無水マレイン酸のクロロホルム溶液によって作成した検量線から得られる係数(f)、無水マレイン酸変性ポリオレフィン溶液における無水マレイン酸の無水環の伸縮ピーク(1780cm-1)の吸光度(I)とマレイン酸のカルボニル基の伸縮ピーク(1720cm-1)の吸光度(II)を用いて下記式により算出した値である。下記式において無水マレイン酸の分子量を98.06、水酸化カリウムの分子量は56.11とした。 The acid value of the olefin resin is a coefficient (f) obtained from a calibration curve prepared with a chloroform solution of maleic anhydride using FT-IR (FT-IR4200, manufactured by Nippon Kogaku Co., Ltd.), in a maleic anhydride-modified polyolefin solution. It is a value calculated by the following formula using the absorbance (I) of the expansion and contraction peak (1780 cm -1 ) of the anhydrous ring of maleic anhydride and the absorbance (II) of the expansion and contraction peak (1720 cm -1 ) of the carbonyl group of maleic anhydride. In the following formula, the molecular weight of maleic anhydride was 98.06, and the molecular weight of potassium hydroxide was 56.11.
<積層体>
(実施例1)
実施例1の接着剤をクロメート処理アルミニウム箔(膜厚:40μm)の光沢面にバーコーターで塗布量4g/m2(dry)で塗布し、80℃−1分間乾燥させた後、未延伸ポリオレフィンフィルム(膜厚:40μm)と100℃で貼り合せた。次にアルミニウム箔のマット面に「ディックドライ LX−906」(DIC株式会社製)を主剤とし、「KW−75」(DIC株式会社製)を硬化剤として、重量比が主剤/硬化剤=100/10となるように配合した接着剤をバーコーターで塗布量4g/m2(dry)で塗布した後、厚さ25μmの延伸ポリアミドフィルムを積層した。その後50℃3日間の養生(エージング)を行い、実施例1の積層体を得た。
<Laminated body>
(Example 1)
The adhesive of Example 1 was applied to the glossy surface of a chromate-treated aluminum foil (film thickness: 40 μm) with a bar coater at a coating amount of 4 g / m 2 (dry), dried at 80 ° C. for 1 minute, and then unstretched polyolefin. It was bonded to a film (film thickness: 40 μm) at 100 ° C. Next, on the matte surface of the aluminum foil, "Dick Dry LX-906" (manufactured by DIC Corporation) is used as the main agent, and "KW-75" (manufactured by DIC Corporation) is used as the curing agent, and the weight ratio is the main agent / curing agent = 100. The adhesive blended so as to be 1/10 was applied with a bar coater at a coating amount of 4 g / m 2 (dry), and then a stretched polyamide film having a thickness of 25 μm was laminated. Then, it was cured (aged) at 50 ° C. for 3 days to obtain a laminate of Example 1.
(実施例2〜5)
アルミニウム箔と未延伸ポリオレフィンフィルムの貼り合せに用いる接着剤を変更した以外は実施例1と同様にして接着剤を調整し、ラミネート物を得た。
(Examples 2 to 5)
The adhesive was adjusted in the same manner as in Example 1 except that the adhesive used for bonding the aluminum foil and the unstretched polyolefin film was changed to obtain a laminate.
(比較例1〜4)
アルミニウム箔と未延伸ポリオレフィンフィルムの貼り合せに用いる接着剤を変更した以外は実施例1と同様にして接着剤を調整し、ラミネート物を得た。
(Comparative Examples 1 to 4)
The adhesive was adjusted in the same manner as in Example 1 except that the adhesive used for bonding the aluminum foil and the unstretched polyolefin film was changed to obtain a laminate.
<評価>
(初期接着強度の測定)
株式会社島津製作所の「オートグラフAGS−J」を使用し、ラミネート物のアルミニウム箔と未延伸ポリオレフィンフィルムの界面の接着強度を剥離速度50mm/min、剥離幅15mm、剥離形態T型の条件で評価した。8.0N/15mm以上を合格とした。
<Evaluation>
(Measurement of initial adhesive strength)
Using "Autograph AGS-J" manufactured by Shimadzu Corporation, the adhesive strength at the interface between the aluminum foil of the laminate and the unstretched polyolefin film is evaluated under the conditions of peeling speed 50 mm / min, peeling width 15 mm, and peeling form T type. did. 8.0N / 15mm or more was regarded as acceptable.
(耐電解液性)
電解液として、エチレンカーボネート:エチルメチルカーボネート:ジメチルカーボネート=1:1:1(wt%)混合液に、LiPF6が1mol/l、ビニレンカーボネートが1wt%、水1000ppmとなるようそれぞれを添加した溶液を用意した。エージング後のラミネート物を電解液35gに85℃で7日間浸漬させた。電解液が乾燥する前の状態で、ラミネート物のアルミニウム箔と未延伸ポリオレフィンフィルムの界面の接着強度を剥離速度50mm/min、剥離幅15mm、剥離形態T型の条件で測定した。浸漬前後の接着強度の保持率から以下のように評価した。
〇:60%以上
△:40%以上60%未満
×:40%未満
(Electrolytic resistance)
As the electrolytic solution, a solution obtained by adding each of a mixed solution of ethylene carbonate: ethyl methyl carbonate: dimethyl carbonate = 1: 1: 1 (wt%) so that LiPF6 is 1 mol / l, vinylene carbonate is 1 wt%, and water is 1000 ppm. I prepared it. The aged laminate was immersed in 35 g of an electrolytic solution at 85 ° C. for 7 days. Before the electrolytic solution was dried, the adhesive strength at the interface between the aluminum foil of the laminate and the unstretched polyolefin film was measured under the conditions of a peeling speed of 50 mm / min, a peeling width of 15 mm, and a peeling form of T type. It was evaluated as follows from the retention rate of the adhesive strength before and after immersion.
〇: 60% or more Δ: 40% or more and less than 60% ×: less than 40%
表2、表3から明らかなように、本発明の接着剤は比較例の接着剤よりも初期接着強度、耐電解液性に優れる。 As is clear from Tables 2 and 3, the adhesive of the present invention is superior in initial adhesive strength and electrolytic solution resistance to the adhesives of Comparative Examples.
本発明の接着剤はオレフィン樹脂のような非極性の基材と金属基材との接着性、耐熱性に優れ、本発明の接着剤を用いて得られる積層体は、例えば電池用包装材に好適に用いることができる。また本発明の接着剤の用途としては電池用包装材やそのための積層体に限定されず、家電外板、家具用素材、建築内装用部材など非極性の基材と金属基材との接着性が必要とされる分野に広く利用可能である。 The adhesive of the present invention is excellent in adhesiveness and heat resistance between a non-polar base material such as an olefin resin and a metal base material, and the laminate obtained by using the adhesive of the present invention can be used as a packaging material for batteries, for example. It can be preferably used. Further, the use of the adhesive of the present invention is not limited to the packaging material for batteries and the laminate for that purpose, and the adhesiveness between non-polar base materials such as home appliance outer panels, furniture materials, and building interior members and metal base materials. Is widely available in fields where
Claims (10)
前記第1剤が酸基含有樹脂(A1)を含む樹脂(A)を含み、
前記第2剤が52℃における粘度が0.05Pa・s以上25Pa・s以下のエポキシ化合物(B1)を含み、
さらに有機リン系化合物(C)と、
イミダゾール化合物(D)と、を含み、
前記有機リン化合物(C)の配合量が前記樹脂(A)100質量部に対して0.01質量部以上5質量部以下であり、
前記イミダゾール化合物(D)の配合量が前記樹脂(A)100質量部に対して0.06質量部以上0.35質量部以下である接着剤。 Including the first agent and the second agent,
The first agent contains a resin (A) containing an acid group-containing resin (A1).
The second agent contains an epoxy compound (B1) having a viscosity at 52 ° C. of 0.05 Pa · s or more and 25 Pa · s or less.
Furthermore, with the organic phosphorus compound (C),
Includes imidazole compound (D),
The blending amount of the organic phosphorus compound (C) is 0.01 part by mass or more and 5 parts by mass or less with respect to 100 parts by mass of the resin (A).
An adhesive in which the blending amount of the imidazole compound (D) is 0.06 parts by mass or more and 0.35 parts by mass or less with respect to 100 parts by mass of the resin (A).
前記第1の基材と第2の基材とを、前記接着剤を介して貼り合せる工程と、
25℃以上100℃以下で12時間以上エージングを行う工程と、を有する積層体の製造方法。 The step of applying the adhesive according to any one of claims 1 to 5 to the first base material, and
A step of bonding the first base material and the second base material via the adhesive, and
A method for producing a laminate, which comprises a step of aging at 25 ° C. or higher and 100 ° C. or lower for 12 hours or longer.
樹脂フィルムと、
前記ポリオレフィンフィルムと前記樹脂フィルムとの間に配置された金属箔と、
前記ポリオレフィンフィルムと前記金属箔との間に配置された接着層と、を含み、
前記接着層が請求項1乃至5のいずれか一項に記載の接着剤の硬化塗膜であることを特徴とする電池用包装材。 Polyolefin film and
With resin film
A metal foil arranged between the polyolefin film and the resin film,
Includes an adhesive layer disposed between the polyolefin film and the metal foil.
A packaging material for a battery, wherein the adhesive layer is a cured coating film of the adhesive according to any one of claims 1 to 5.
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JP2017171814A (en) * | 2016-03-25 | 2017-09-28 | 株式会社巴川製紙所 | Adhesive sheet for printed wiring board |
WO2017187904A1 (en) * | 2016-04-27 | 2017-11-02 | Dic株式会社 | Adhesive composition for laminating, laminate, and secondary battery |
WO2017221801A1 (en) * | 2016-06-24 | 2017-12-28 | Dic株式会社 | Adhesive composition for laminating, laminate, and secondary battery |
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WO2024048444A1 (en) * | 2022-08-30 | 2024-03-07 | ユニチカ株式会社 | Coating agent, coating film, and laminate |
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