JP2021102700A - Coating agent, laminate, molded body and packaging material - Google Patents
Coating agent, laminate, molded body and packaging material Download PDFInfo
- Publication number
- JP2021102700A JP2021102700A JP2019234215A JP2019234215A JP2021102700A JP 2021102700 A JP2021102700 A JP 2021102700A JP 2019234215 A JP2019234215 A JP 2019234215A JP 2019234215 A JP2019234215 A JP 2019234215A JP 2021102700 A JP2021102700 A JP 2021102700A
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- Prior art keywords
- acid group
- group
- resin
- compound
- coating agent
- Prior art date
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- 239000011248 coating agent Substances 0.000 title claims abstract description 96
- 239000005022 packaging material Substances 0.000 title claims description 9
- 239000002253 acid Substances 0.000 claims abstract description 108
- 150000001875 compounds Chemical class 0.000 claims abstract description 73
- 229920005989 resin Polymers 0.000 claims abstract description 61
- 239000011347 resin Substances 0.000 claims abstract description 61
- 229920005672 polyolefin resin Polymers 0.000 claims abstract description 57
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 48
- 238000002425 crystallisation Methods 0.000 claims abstract description 48
- 230000008025 crystallization Effects 0.000 claims abstract description 48
- 239000004593 Epoxy Substances 0.000 claims abstract description 29
- 238000000034 method Methods 0.000 claims abstract description 27
- 239000000203 mixture Substances 0.000 claims abstract description 10
- 239000007788 liquid Substances 0.000 claims abstract description 6
- 238000001938 differential scanning calorimetry curve Methods 0.000 claims abstract description 5
- 238000000113 differential scanning calorimetry Methods 0.000 claims abstract description 4
- -1 isocyanate compound Chemical class 0.000 claims description 66
- 229920001577 copolymer Polymers 0.000 claims description 33
- 239000000463 material Substances 0.000 claims description 30
- 238000000576 coating method Methods 0.000 claims description 27
- 239000012948 isocyanate Substances 0.000 claims description 21
- 229910052751 metal Inorganic materials 0.000 claims description 21
- 239000002184 metal Substances 0.000 claims description 21
- VXNZUUAINFGPBY-UHFFFAOYSA-N 1-Butene Chemical compound CCC=C VXNZUUAINFGPBY-UHFFFAOYSA-N 0.000 claims description 14
- 238000002156 mixing Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 12
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 9
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 claims description 9
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 9
- 125000003504 2-oxazolinyl group Chemical group O1C(=NCC1)* 0.000 claims description 8
- 239000010936 titanium Substances 0.000 claims description 7
- 229910052719 titanium Inorganic materials 0.000 claims description 6
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 claims description 5
- 125000003700 epoxy group Chemical group 0.000 claims description 5
- 150000003512 tertiary amines Chemical class 0.000 claims description 5
- 150000001412 amines Chemical class 0.000 claims description 3
- 229920003180 amino resin Polymers 0.000 claims description 3
- 125000004069 aziridinyl group Chemical group 0.000 claims description 3
- IAQRGUVFOMOMEM-UHFFFAOYSA-N butene Natural products CC=CC IAQRGUVFOMOMEM-UHFFFAOYSA-N 0.000 claims description 3
- 150000003003 phosphines Chemical class 0.000 claims description 3
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 claims description 2
- 150000002460 imidazoles Chemical class 0.000 claims description 2
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 claims 1
- 239000013522 chelant Substances 0.000 claims 1
- 229910052698 phosphorus Inorganic materials 0.000 claims 1
- 239000011574 phosphorus Substances 0.000 claims 1
- 150000003839 salts Chemical class 0.000 claims 1
- 230000004888 barrier function Effects 0.000 abstract description 21
- 239000011247 coating layer Substances 0.000 abstract description 19
- 239000010409 thin film Substances 0.000 abstract description 4
- 230000009257 reactivity Effects 0.000 abstract description 3
- 239000010408 film Substances 0.000 description 125
- 239000002585 base Substances 0.000 description 62
- 239000000178 monomer Substances 0.000 description 39
- 239000012790 adhesive layer Substances 0.000 description 33
- 239000002904 solvent Substances 0.000 description 33
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 32
- 239000010410 layer Substances 0.000 description 31
- 238000002844 melting Methods 0.000 description 22
- 230000008018 melting Effects 0.000 description 22
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 22
- 239000000123 paper Substances 0.000 description 21
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 19
- 150000001336 alkenes Chemical class 0.000 description 18
- 239000003822 epoxy resin Substances 0.000 description 17
- 229920000647 polyepoxide Polymers 0.000 description 17
- 239000000565 sealant Substances 0.000 description 16
- 125000004432 carbon atom Chemical group C* 0.000 description 15
- 239000000047 product Substances 0.000 description 15
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
- 239000003960 organic solvent Substances 0.000 description 14
- 229920000098 polyolefin Polymers 0.000 description 14
- 238000007639 printing Methods 0.000 description 14
- 229910052757 nitrogen Inorganic materials 0.000 description 13
- 229920002799 BoPET Polymers 0.000 description 12
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 12
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 12
- 229920001519 homopolymer Polymers 0.000 description 12
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 11
- 239000005977 Ethylene Substances 0.000 description 11
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 11
- 229910052782 aluminium Inorganic materials 0.000 description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 10
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 10
- 150000008065 acid anhydrides Chemical class 0.000 description 10
- 230000032683 aging Effects 0.000 description 10
- XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 10
- 239000000976 ink Substances 0.000 description 10
- 229920000642 polymer Polymers 0.000 description 10
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 9
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 9
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 9
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 9
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical group OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 8
- 239000004743 Polypropylene Substances 0.000 description 8
- 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 8
- 230000000052 comparative effect Effects 0.000 description 8
- XEEYBQQBJWHFJM-UHFFFAOYSA-N iron Substances [Fe] XEEYBQQBJWHFJM-UHFFFAOYSA-N 0.000 description 8
- 235000011007 phosphoric acid Nutrition 0.000 description 8
- 229920001155 polypropylene Polymers 0.000 description 8
- 239000001993 wax Substances 0.000 description 8
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 7
- 235000019441 ethanol Nutrition 0.000 description 7
- 239000000377 silicon dioxide Substances 0.000 description 7
- 239000000126 substance Substances 0.000 description 7
- 229920005992 thermoplastic resin Polymers 0.000 description 7
- WWZKQHOCKIZLMA-UHFFFAOYSA-N Caprylic acid Natural products CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 6
- 239000004952 Polyamide Substances 0.000 description 6
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 6
- 125000002723 alicyclic group Chemical group 0.000 description 6
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 6
- UAEPNZWRGJTJPN-UHFFFAOYSA-N methylcyclohexane Chemical compound CC1CCCCC1 UAEPNZWRGJTJPN-UHFFFAOYSA-N 0.000 description 6
- 229920002647 polyamide Polymers 0.000 description 6
- 229920001296 polysiloxane Polymers 0.000 description 6
- 239000000243 solution Substances 0.000 description 6
- 239000000758 substrate Substances 0.000 description 6
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 5
- NIPNSKYNPDTRPC-UHFFFAOYSA-N N-[2-oxo-2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)ethyl]-2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidine-5-carboxamide Chemical compound O=C(CNC(=O)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)N1CC2=C(CC1)NN=N2 NIPNSKYNPDTRPC-UHFFFAOYSA-N 0.000 description 5
- 239000004721 Polyphenylene oxide Substances 0.000 description 5
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 5
- 239000002635 aromatic organic solvent Substances 0.000 description 5
- 125000003118 aryl group Chemical group 0.000 description 5
- 230000000903 blocking effect Effects 0.000 description 5
- 238000006243 chemical reaction Methods 0.000 description 5
- 238000001035 drying Methods 0.000 description 5
- JBTWLSYIZRCDFO-UHFFFAOYSA-N ethyl methyl carbonate Chemical compound CCOC(=O)OC JBTWLSYIZRCDFO-UHFFFAOYSA-N 0.000 description 5
- 230000004927 fusion Effects 0.000 description 5
- 150000002334 glycols Chemical class 0.000 description 5
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 5
- 229920001903 high density polyethylene Polymers 0.000 description 5
- 239000004700 high-density polyethylene Substances 0.000 description 5
- 239000003112 inhibitor Substances 0.000 description 5
- 150000002576 ketones Chemical class 0.000 description 5
- 238000010030 laminating Methods 0.000 description 5
- 229920001684 low density polyethylene Polymers 0.000 description 5
- 239000004702 low-density polyethylene Substances 0.000 description 5
- 239000011572 manganese Substances 0.000 description 5
- 239000012046 mixed solvent Substances 0.000 description 5
- 230000004048 modification Effects 0.000 description 5
- 238000012986 modification Methods 0.000 description 5
- 150000003016 phosphoric acids Chemical class 0.000 description 5
- 229920000570 polyether Polymers 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 5
- 239000005020 polyethylene terephthalate Substances 0.000 description 5
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 4
- 239000004698 Polyethylene Substances 0.000 description 4
- 241000555081 Stanus Species 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- 230000001070 adhesive effect Effects 0.000 description 4
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 4
- PXKLMJQFEQBVLD-UHFFFAOYSA-N bisphenol F Chemical compound C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 4
- 239000010949 copper Substances 0.000 description 4
- 125000005442 diisocyanate group Chemical group 0.000 description 4
- WSSSPWUEQFSQQG-UHFFFAOYSA-N dimethylbutene Natural products CC(C)CC=C WSSSPWUEQFSQQG-UHFFFAOYSA-N 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- JBKVHLHDHHXQEQ-UHFFFAOYSA-N epsilon-caprolactam Chemical compound O=C1CCCCCN1 JBKVHLHDHHXQEQ-UHFFFAOYSA-N 0.000 description 4
- HQQADJVZYDDRJT-UHFFFAOYSA-N ethene;prop-1-ene Chemical group C=C.CC=C HQQADJVZYDDRJT-UHFFFAOYSA-N 0.000 description 4
- XLLIQLLCWZCATF-UHFFFAOYSA-N ethylene glycol monomethyl ether acetate Natural products COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
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- ZSIAUFGUXNUGDI-UHFFFAOYSA-N hexan-1-ol Chemical compound CCCCCCO ZSIAUFGUXNUGDI-UHFFFAOYSA-N 0.000 description 4
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- YWAKXRMUMFPDSH-UHFFFAOYSA-N pentene Chemical compound CCCC=C YWAKXRMUMFPDSH-UHFFFAOYSA-N 0.000 description 4
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- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 4
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- 238000007740 vapor deposition Methods 0.000 description 4
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- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 239000002518 antifoaming agent Substances 0.000 description 3
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- KHPCPRHQVVSZAH-HUOMCSJISA-N Rosin Natural products O(C/C=C/c1ccccc1)[C@H]1[C@H](O)[C@@H](O)[C@@H](O)[C@@H](CO)O1 KHPCPRHQVVSZAH-HUOMCSJISA-N 0.000 description 2
- 239000006087 Silane Coupling Agent Substances 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 229910052776 Thorium Inorganic materials 0.000 description 2
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- UKLDJPRMSDWDSL-UHFFFAOYSA-L [dibutyl(dodecanoyloxy)stannyl] dodecanoate Chemical compound CCCCCCCCCCCC(=O)O[Sn](CCCC)(CCCC)OC(=O)CCCCCCCCCCC UKLDJPRMSDWDSL-UHFFFAOYSA-L 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- LPQOADBMXVRBNX-UHFFFAOYSA-N ac1ldcw0 Chemical compound Cl.C1CN(C)CCN1C1=C(F)C=C2C(=O)C(C(O)=O)=CN3CCSC1=C32 LPQOADBMXVRBNX-UHFFFAOYSA-N 0.000 description 2
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- 125000004018 acid anhydride group Chemical group 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
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- 239000001361 adipic acid Substances 0.000 description 2
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- 239000012298 atmosphere Substances 0.000 description 2
- TZCXTZWJZNENPQ-UHFFFAOYSA-L barium sulfate Chemical compound [Ba+2].[O-]S([O-])(=O)=O TZCXTZWJZNENPQ-UHFFFAOYSA-L 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052797 bismuth Inorganic materials 0.000 description 2
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- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- 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
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Classifications
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D123/00—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers
- C09D123/26—Coating compositions based on homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Coating compositions based on derivatives of such polymers modified by chemical after-treatment
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- B32B15/00—Layered products comprising a layer of metal
- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/088—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyamides
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- B32B15/04—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B15/08—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
- B32B15/09—Layered products comprising a layer of metal comprising metal as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin comprising polyesters
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- B32B15/00—Layered products comprising a layer of metal
- B32B15/20—Layered products comprising a layer of metal comprising aluminium or copper
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- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
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- B32B27/06—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material
- B32B27/08—Layered products comprising a layer of synthetic resin as the main or only constituent of a layer, which is next to another layer of the same or of a different material of synthetic resin
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/30—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers
- B32B27/304—Layered products comprising a layer of synthetic resin comprising vinyl (co)polymers; comprising acrylic (co)polymers comprising vinyl halide (co)polymers, e.g. PVC, PVDC, PVF, PVDF
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- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B27/00—Layered products comprising a layer of synthetic resin
- B32B27/36—Layered products comprising a layer of synthetic resin comprising polyesters
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B7/00—Layered products characterised by the relation between layers; Layered products characterised by the relative orientation of features between layers, or by the relative values of a measurable parameter between layers, i.e. products comprising layers having different physical, chemical or physicochemical properties; Layered products characterised by the interconnection of layers
- B32B7/04—Interconnection of layers
- B32B7/12—Interconnection of layers using interposed adhesives or interposed materials with bonding properties
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/0427—Coating with only one layer of a composition containing a polymer binder
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J7/00—Chemical treatment or coating of shaped articles made of macromolecular substances
- C08J7/04—Coating
- C08J7/048—Forming gas barrier coatings
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/60—Additives non-macromolecular
- C09D7/63—Additives non-macromolecular organic
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
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- C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
- C09D7/40—Additives
- C09D7/65—Additives macromolecular
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/10—Coating on the layer surface on synthetic resin layer or on natural or synthetic rubber layer
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2255/00—Coating on the layer surface
- B32B2255/26—Polymeric coating
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B32—LAYERED PRODUCTS
- B32B—LAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
- B32B2307/00—Properties of the layers or laminate
- B32B2307/70—Other properties
- B32B2307/724—Permeability to gases, adsorption
- B32B2307/7242—Non-permeable
- B32B2307/7246—Water vapor barrier
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- B—PERFORMING OPERATIONS; TRANSPORTING
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- B32B2553/00—Packaging equipment or accessories not otherwise provided for
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- C08J2377/00—Characterised by the use of polyamides obtained by reactions forming a carboxylic amide link in the main chain; Derivatives of such polymers
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- C08J2423/00—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers
- C08J2423/26—Characterised by the use of homopolymers or copolymers of unsaturated aliphatic hydrocarbons having only one carbon-to-carbon double bond; Derivatives of such polymers modified by chemical after-treatment
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Abstract
Description
本発明は、コーティング剤および該コーティング剤を塗工した積層体、成型体及び包装材に関する。 The present invention relates to a coating agent and a laminate, a molded body and a packaging material coated with the coating agent.
各種食品や薬品等を入れるための包装容器は、ポリエチレンテレフタレート(PET)、ナイロン(Ny)、ポリプロピレン(PP)等の熱可塑性樹脂フィルムや紙を成形または成型加工することにより作製されている。これらの包装容器に、湿気を嫌う製品を梱包する際には、防湿加工を施す必要がある。 Packaging containers for containing various foods, chemicals, etc. are manufactured by molding or molding a thermoplastic resin film such as polyethylene terephthalate (PET), nylon (Ny), polypropylene (PP), or paper. When packing products that dislike moisture in these packaging containers, it is necessary to apply a moisture-proof treatment.
防湿加工法としては、防湿性材料を溶融し基材上に積層する方法や、防湿性材料を含むコート液を塗布(あるいは含浸)する方法があるが、薄膜化が可能であることや、取り扱いが容易であることなどから、後者の方が有利である。防湿性を有する材料としては、特許文献1〜3に記載のようなものが知られている。 As a moisture-proof processing method, there are a method of melting a moisture-proof material and laminating it on a base material, and a method of applying (or impregnating) a coating liquid containing the moisture-proof material. The latter is more advantageous because it is easy to use. As a material having a moisture-proof property, those described in Patent Documents 1 to 3 are known.
しかしながら上記特許文献1〜3記載の発明は、いずれも防湿性が十分ではなく、また、特許文献1、2では、基材への塗布には樹脂組成物の融点以上に加熱しなければならず、特殊な塗布装置や複雑な塗布工程が必要であった。 However, the inventions described in Patent Documents 1 to 3 are not sufficiently moisture-proof, and in Patent Documents 1 and 2, they must be heated to a temperature equal to or higher than the melting point of the resin composition for coating on a substrate. , Special coating equipment and complicated coating process were required.
本発明はこのような状況に鑑みなされたものであって、優れた水蒸気バリア性を付与できるコーティング剤および該コーティング剤を塗布した積層体、成型体及び包装材に関する。 The present invention has been made in view of such a situation, and relates to a coating agent capable of imparting excellent water vapor barrier properties, and a laminate, a molded body, and a packaging material coated with the coating agent.
本発明は、第1剤と、第2剤とを含み、第1剤は酸基含有オレフィン樹脂(A1)を含む樹脂(A)を含み、第2剤は前記酸基含有オレフィン樹脂(A1)が有する酸基と反応性を有する化合物(B)を含み、酸基含有オレフィン樹脂(A1)は、酸基含有オレフィン樹脂(A1)と25℃で液体であるエポキシ化合物とがエポキシ過剰率が0.1以上1.5以下となるよう配合された組成物の硬化物を、JIS−K−7121に記載の結晶化温度の測定方法に従って測定した示差走査熱量測定において描かれるDSC曲線に結晶化ピークが観測されることを特徴とするコーティング剤に関する。 The present invention includes a first agent and a second agent, the first agent contains a resin (A) containing an acid group-containing olefin resin (A1), and the second agent is the acid group-containing olefin resin (A1). The acid group-containing olefin resin (A1) contains the compound (B) that is reactive with the acid group of the acid group, and the acid group-containing olefin resin (A1) and the epoxy compound that is liquid at 25 ° C. have an epoxy excess ratio of 0. The cured product of the composition blended so as to be 1 or more and 1.5 or less has a crystallization peak on the DSC curve drawn in the differential scanning calorimetry measured according to the method for measuring the crystallization temperature described in JIS-K-7121. The present invention relates to a coating agent characterized by being observed.
本発明のコーティング剤によれば、薄膜でありながら水蒸気バリア性に優れたコーティング層を簡便な装置で容易に形成することができる。また、このコーティング剤を塗布した積層体、成型体、包装材は優れた水蒸気バリア性を備えたものとなる。 According to the coating agent of the present invention, a coating layer which is a thin film but has excellent water vapor barrier properties can be easily formed by a simple device. Further, the laminate, the molded body, and the packaging material to which this coating agent is applied have excellent water vapor barrier properties.
<コーティング剤>
本発明のコーティング剤は、酸基含有オレフィン樹脂(A1)を含む第1剤と、酸基含有オレフィン樹脂(A1)が有する酸基と反応性を有する化合物(B)を含む第2剤とからなる2液型コーティング剤である。以下、本発明の剤の各成分について詳細に説明する。
<Coating agent>
The coating agent of the present invention comprises a first agent containing an acid group-containing olefin resin (A1) and a second agent containing a compound (B) reactive with the acid group of the acid group-containing olefin resin (A1). It is a two-component coating agent. Hereinafter, each component of the agent of the present invention will be described in detail.
(第1剤)
第1剤は、樹脂(A)として、酸基含有オレフィン樹脂(A1)を含む。酸基含有オレフィン樹脂(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。
(1st agent)
The first agent contains an acid group-containing olefin resin (A1) as the resin (A). Examples of the acid group contained in the acid group-containing olefin 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.
このような酸基含有オレフィン樹脂(A1)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 such an acid group-containing olefin resin (A1) include homopolymers or copolymers of acid group-containing monomers, copolymers of acid group-containing monomers and olefin-based monomers, modified acid group-containing monomers of polyolefins, and the like. Can be mentioned.
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後述する樹脂フィルムへの密着性や耐溶剤性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、基材への密着性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 are particularly preferable, because they have good adhesion to a resin film and solvent resistance, which will be described later. -It is preferable to use it in combination with butene because it has excellent resistance to solvents and adhesion to the substrate.
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 acid group-containing monomer used for preparing the homopolymer or copolymer of the acid group-containing monomer described above shall 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。これらの中で特に密着性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、密着性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 adhesion, and propylene alone is preferable. 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 adhesion.
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 in which the polyolefin is melted and an acid group-containing monomer (graft monomer) is added thereto to cause a graft reaction, or the polyolefin is dissolved 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 equal to or 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.
本発明で用いられる酸基含有オレフィン樹脂(A1)は、酸基含有オレフィン樹脂(A1)と25℃で液体であるエポキシ化合物とがエポキシ過剰率が0.1以上1.5以下となるよう配合された組成物の硬化物を、JIS−K−7121に記載の結晶化温度の測定方法に従って測定した示差走査熱量測定において描かれるDSC曲線に結晶化ピークが観測されるもの(融解ピーク終了時より30℃高い温度まで加熱し、この温度に10分間保った後、10℃/minで結晶化ピーク終了時より50℃低い温度まで冷却した際に描かれるDSC曲線に結晶化ピークが観測されるもの)を用いる。 The acid group-containing olefin resin (A1) used in the present invention is a mixture of the acid group-containing olefin resin (A1) and an epoxy compound that is liquid at 25 ° C. so that the epoxy excess ratio is 0.1 or more and 1.5 or less. A crystallization peak is observed on the DSC curve drawn in the differential scanning calorimetry of the cured product of the obtained composition measured according to the method for measuring the crystallization temperature described in JIS-K-7121 (from the end of the melting peak). A crystallization peak is observed on the DSC curve drawn when the mixture is heated to a temperature 30 ° C higher, kept at this temperature for 10 minutes, and then cooled to a temperature 50 ° C lower than the end of the crystallization peak at 10 ° C / min. ) Is used.
酸基含有オレフィン樹脂によっては、硬化物自体は結晶性を有していても上記の方法では結晶化ピークが観測されず、再度10℃/minで昇温した際に結晶化ピーク(いわゆる冷結晶化によるもの)が観測されるものもある。本発明では上述の条件にて測定したDCS曲線において結晶化ピークが観測される酸基含有オレフィン樹脂(A1)を用いることで、コーティング剤の硬化塗膜中における結晶化部位の比率を高めてることができ、これにより各種溶剤への耐性に優れたコーティング剤とすることができる。また、コーティング剤の硬化塗膜が溶剤によって侵され難いため、酸やアルカリなどの溶液を内包する場合であっても塗膜がこれらの影響を受けにくく、耐薬品性にも優れたコーティング剤となる。さらに結晶化部位が疑似的にフィラーの役割を果たし、迷路効果により水蒸気バリア性に優れたコーティング剤となっていると推測している。 Depending on the acid group-containing olefin resin, even if the cured product itself has crystallization, a crystallization peak is not observed by the above method, and a crystallization peak (so-called cold crystal) is observed when the temperature is raised again at 10 ° C./min. Some are observed (due to crystallization). In the present invention, the ratio of crystallization sites in the cured coating of the coating agent is increased by using an acid group-containing olefin resin (A1) in which a crystallization peak is observed in the DCS curve measured under the above conditions. This makes it possible to obtain a coating agent having excellent resistance to various solvents. In addition, since the cured coating film of the coating agent is not easily attacked by the solvent, the coating film is not easily affected by these even when a solution such as acid or alkali is included, and the coating agent has excellent chemical resistance. Become. Furthermore, it is speculated that the crystallization site acts as a pseudo-filler, and the maze effect makes it a coating agent with excellent water vapor barrier properties.
上述の硬化物の結晶化温度が高すぎる場合、エージング温度が低いとコーティング剤の硬化塗膜中における結晶化部位の比率が十分にならず、耐溶剤性、耐薬品性が低下するおとれがあり、これを避けるためにはエージング温度を高く設定しなければならない。作業性、省エネルギーの観点から酸基含有オレフィン樹脂(A1)は、上述の硬化物の結晶化温度が10℃以上60℃以下となるものを用いることが好ましく、より好ましくは20℃以上50℃以下である。なお上述の硬化物の結晶化温度は酸基含有オレフィン樹脂(A1)とエポキシ化合物とのエポキシ過剰率により変動するが、0.1以上1.5以下のいずれかの範囲で結晶化温度が10℃以上60℃以下であればよい。 When the crystallization temperature of the above-mentioned cured product is too high, if the aging temperature is low, the ratio of the crystallized portion in the cured coating film of the coating agent is not sufficient, and the solvent resistance and chemical resistance are lowered. Yes, the aging temperature must be set high to avoid this. From the viewpoint of workability and energy saving, the acid group-containing olefin resin (A1) preferably has a crystallization temperature of 10 ° C. or higher and 60 ° C. or lower, more preferably 20 ° C. or higher and 50 ° C. or lower. Is. The crystallization temperature of the cured product described above varies depending on the epoxy excess ratio of the acid group-containing olefin resin (A1) and the epoxy compound, but the crystallization temperature is 10 in any range of 0.1 or more and 1.5 or less. It may be ℃ or more and 60 ℃ or less.
また、酸基含有オレフィン樹脂(A1)として、上述の硬化物の結晶化熱量が1mJ/mg以上、より好ましくは5mJ/mg以上であり、60mJ/mg以下、より好ましくは45mJ/mg以下となるものを用いることが好ましい。これにより、発熱する内容物を内包する用途や、周囲の温度が上昇しやすい環境で使用する場合であっても耐溶剤性、耐薬品性、水蒸気バリア性に優れたコーティング剤とすることができる。なお結晶化熱量は、JIS−K−7122に記載の方法で測定することができる。 Further, as the acid group-containing olefin resin (A1), the calorific value for crystallization of the above-mentioned cured product is 1 mJ / mg or more, more preferably 5 mJ / mg or more, 60 mJ / mg or less, more preferably 45 mJ / mg or less. It is preferable to use one. As a result, it is possible to obtain a coating agent having excellent solvent resistance, chemical resistance, and water vapor barrier property even when it is used for containing heat-generating contents or in an environment where the ambient temperature tends to rise. .. The amount of heat of crystallization can be measured by the method described in JIS-K-7122.
酸基含有オレフィン樹脂(A1)は結晶性である。耐溶剤性の観点から酸基含有オレフィン樹脂(A1)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が高すぎる場合、エージング温度が低いとコーティング剤が濡れ広がり難く、基材密着性が低下するおそれがある。これを避けるためにはエージング温度を高く設定しなければならないことから、酸基含有オレフィン樹脂(A1)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。酸基含有オレフィン樹脂(A1)の融点は、JIS−K−7121に記載の方法で測定することができる。 The acid group-containing olefin resin (A1) is crystalline. From the viewpoint of solvent resistance, the melting point of the acid group-containing olefin resin (A1) is preferably 50 ° C. or higher, more preferably 60 ° C. or higher, and even more preferably 65 ° C. or higher. Further, when the melting point of the acid group-containing olefin resin is too high, if the aging temperature is low, the coating agent is difficult to wet and spread, and the adhesion to the base material may decrease. Since the aging temperature must be set high to avoid this, the melting point of the acid group-containing olefin resin (A1) is preferably 120 ° C. or lower, more preferably 100 ° C. or lower, and 90 ° C. The following is more preferable. The melting point of the acid group-containing olefin resin (A1) can be measured by the method described in JIS-K-7121.
酸基含有オレフィン樹脂(A1)は、融解熱量が1mJ/mg以上、より好ましくは5mJ/mg以上であり、60mJ/mg以下、より好ましくは45mJ/mg以下であることが好ましい。これにより耐溶剤性、耐薬品性、水蒸気バリア性に優れたコーティング剤とすることができる。なお、酸基含有オレフィン樹脂(A1)の融解熱量はJIS−K−7122に記載の方法で測定することができる。 The acid group-containing olefin resin (A1) has a heat of fusion of 1 mJ / mg or more, more preferably 5 mJ / mg or more, and preferably 60 mJ / mg or less, more preferably 45 mJ / mg or less. As a result, a coating agent having excellent solvent resistance, chemical resistance, and water vapor barrier property can be obtained. The amount of heat of fusion of the acid group-containing olefin resin (A1) can be measured by the method described in JIS-K-7122.
基材への密着性を良好なものとするため酸基含有オレフィン樹脂(A1)の重量平均分子量は10,000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(A1)の重量平均分子量は200,000以下であることが好ましい。より好ましくは50,000以上180,000以下である。 The weight average molecular weight of the acid group-containing olefin resin (A1) is preferably 10,000 or more in order to improve the adhesion to the base material. Further, in order to ensure appropriate fluidity, the weight average molecular weight of the acid group-containing olefin resin (A1) is preferably 200,000 or less. More preferably, it is 50,000 or more and 180,000 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(A1)の酸価は、一例として0.1mgKOH/g以上である。オレフィン鎖の構造にもよるが、酸価が高いと硬化塗膜中において架橋点が多いためにオレフィン鎖が結晶化し難くなる傾向にあり、耐溶剤性の観点から50mgKOH/g以下であることが好ましい。より好ましくは5mgKOH/g以上40mgKOH/g以下であり、5mgKOH/g以上30mgKOH/g以下である。 The acid value of the acid group-containing olefin resin (A1) is, for example, 0.1 mgKOH / g or more. Although it depends on the structure of the olefin chain, if the acid value is high, the olefin chain tends to be difficult to crystallize because there are many cross-linking points in the cured coating film, and it is 50 mgKOH / g or less from the viewpoint of solvent resistance. preferable. More preferably, it is 5 mgKOH / g or more and 40 mgKOH / g or less, and 5 mgKOH / g or more and 30 mgKOH / g or less.
第1剤は、樹脂(A)の全量が酸基含有オレフィン樹脂(A1)であってもよいが、酸基含有オレフィン樹脂(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コーティング剤の耐溶剤性が向上する。 The first agent may be an acid group-containing olefin resin (A1) in which the entire amount of the resin (A) is an acid group-containing olefin resin (A1), but a resin (A2) having no reactive functional group in addition to the acid group-containing olefin resin (A1). May include. The resin (A2) is preferably a crystalline olefin resin. When the resin (A2) is a crystalline olefin resin, the solvent resistance of the coating agent is improved.
樹脂(A2)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。これらの中で特に耐溶剤性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。 Examples of the resin (A2) include 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. Examples thereof include copolymers of olefins having 2 to 8 carbon atoms and other monomers. 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 Copolymers, α-olefin copolymers such as ethylene / 4-methyl-1-pentene copolymers, ethylene / hexene copolymers, ethylene / methylmethacrylate copolymers, propylene / 1-butene copolymers, etc. Can be mentioned. Among these, a homopolymer of an olefin having 3 to 8 carbon atoms and a copolymer of two or more kinds of olefins having 3 to 8 carbon atoms are preferable from the viewpoint of particularly good solvent resistance, and propylene is preferable. A homopolymer or copolymer is more preferable, and a propylene homopolymer is more preferable.
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2,000〜200,000であることが好ましい。樹脂(A2)の重量平均分子量は20,000〜190,000であることがより好ましく、40,000〜180,000であることがより好ましい。 Since the resin (A2) has high solubility in a solvent and improves coatability, the weight average molecular weight is preferably 2,000 to 200,000. The weight average molecular weight of the resin (A2) is more preferably 20,000 to 190,000, and even more preferably 40,000 to 180,000.
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.
樹脂(A2)は結晶性が高く、配合量が多すぎると保存中に第1剤の液温が低くなると樹脂(A2)が析出したり、第1剤がゲル化したりして、使用前に加温する必要が生じる場合がある。
酸基含有オレフィン樹脂(A1)と樹脂(A2)との配合比(A1):(A2)は一例として100:0〜10:90であり、他の一態様としては100:1〜15:85であり、他の一態様として75:25〜15:85である。これにより、耐薬品性、耐溶剤性、水蒸気バリア性に加え、保存安定性に優れるコーティング剤とすることができる。
The resin (A2) has high crystallinity, and if the blending amount is too large, the resin (A2) may precipitate or the first agent may gel if the liquid temperature of the first agent becomes low during storage, and the resin (A2) may gel before use. It may be necessary to heat.
The compounding ratio (A1): (A2) of the acid group-containing olefin resin (A1) and the resin (A2) is, for example, 100: 0 to 10:90, and another aspect is 100: 1 to 15:85. And another aspect is 75:25 to 15:85. This makes it possible to obtain a coating agent having excellent storage stability in addition to chemical resistance, solvent resistance, and water vapor barrier property.
(第2剤)
第2剤は、酸基含有オレフィン樹脂(A1)が有する酸基と反応性を有する化合物(B)、いわゆる硬化剤を含む。このような化合物(B)としては、イソシアネート化合物(B1)、エポキシ化合物(B2)、アジリジン基含有化合物(B3)、カルボジイミド基含有化合物(B4)、オキサゾリン基含有化合物(B5)、ヒドラジド基含有化合物(B6)、アミノ樹脂(B7)等が挙げられる。
(Second agent)
The second agent contains a compound (B) that is reactive with the acid group of the acid group-containing olefin resin (A1), that is, a so-called curing agent. Examples of such a compound (B) include an isocyanate compound (B1), an epoxy compound (B2), an aziridine group-containing compound (B3), a carbodiimide group-containing compound (B4), an oxazoline group-containing compound (B5), and a hydrazide group-containing compound. (B6), amino resin (B7) and the like can be mentioned.
イソシアネート化合物(B1)は一分子中に複数のイソシアネート基を有するもの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。具体例としては、ブタン−1,4−ジイソシアネート、ブテンジイソシアネート、1,3−ブタジエン−1,4−ジイソシアネート、ヘキサメチレンジイソシアネート、2,2,4−トリメチルヘキサメチレンジイソシアネート、2,4,4−トリメチルヘキサメチレンジイソシアネート、1,3,6−ヘキサメチレントリイソシアネート、オクタメチレンジイソシアネート、1,8−ジイソシアネート−4−イソシアネートメチルオクタン、1,6,11−ウンデカントリイソシアネート、キシリレンジイソシアネート、m−テトラメチルキシリレンジイソシアネート、リジンジイソシアネート、リジンエステルトリイソシアネート等の脂肪族ジイソシアネート、 The isocyanate compound (B1) is not particularly limited as long as it has a plurality of isocyanate groups in one molecule, and conventionally known compounds can be used. Specific examples include butane-1,4-diisocyanate, butene diisocyanate, 1,3-butadiene-1,4-diisocyanate, hexamethylene diisocyanate, 2,2,4-trimethyl hexamethylene diisocyanate, and 2,4,4-trimethyl. Hexamethylene diisocyanate, 1,3,6-hexamethylene triisocyanate, octamethylene diisocyanate, 1,8-diisocyanate-4-isocyanate methyloctane, 1,6,11-undecantriisocyanate, xylylene diisocyanate, m-tetramethylxyli Aliphatic diisocyanates such as range isocyanate, lysine diisocyanate, and lysine ester triisocyanate
シクロヘキサン−1,4−ジイソシアネート、イソホロンジイソシアネート、ジシクロヘキシルメタン−4,4’−ジイソシアネート、1,3−ビス(イソシアネートメチル)シクロヘキサン、メチルシクロヘキサンジイソシアネート、イソプロピリデンジシクロヘキシル−4,4’−ジイソシアネート、ノルボルナンジイソシアネート等の脂環族ジイソシアネート、 Cyclohexane-1,4-diisocyanate, isophorone diisocyanate, dicyclohexylmethane-4,4'-diisocyanate, 1,3-bis (isocyanatemethyl) cyclohexane, methylcyclohexanediisocyanate, isopropyridene dicyclohexyl-4,4'-diisocyanate, norbornane diisocyanate, etc. Alicyclic diisocyanate,
1,5−ナフチレンジイソシアネート、4,4’−ジフェニルメタンジイソシアネート、4,4’−ジフェニルジメチルメタンジイソシアネート、4,4’−ジベンジルジイソシアネート、ジアルキルジフェニルメタンジイソシアネート、テトラアルキルジフェニルメタンジイソシアネート、1,3−フェニレンジイソシアネート、1,4−フェニレンジイソシアネート、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等の芳香族ジイソシアネートが挙げられる。 1,5-naphthylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 4,4'-diphenyldimethylmethane diisocyanate, 4,4'-dibenzyl diisocyanate, dialkyldiphenylmethane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 1,3-phenylenediocyanate , 1,4-phenylenediocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate and other aromatic diisocyanates.
これらから誘導された化合物、即ち、前記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を用いることもできる。 Compounds derived from these, that is, isocyanurates, adducts, biurets, uretdiones, allophanates, prepolymers having isocyanate residues (low polymers obtained from diisocyanates and polyols), or these A complex or the like can also be used.
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イソシアネート化合物(B1)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 a reactivity with the isocyanate group may be used as the isocyanate compound (B1). 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.
中でも、保存安定性や基材への密着性に優れることからイソホロンジイソシアネート、ヘキサメチレンジイソシアネート等の脂肪族イソシアネート、脂肪族イソシアネートから誘導された化合物を用いることが好ましい。 Among them, it is preferable to use a compound derived from an aliphatic isocyanate such as isophorone diisocyanate or hexamethylene diisocyanate or an aliphatic isocyanate because it is excellent in storage stability and adhesion to a base material.
エポキシ化合物(B2)としては、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テ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;
樹脂骨格中にゴム骨格(例えばポリブタジエン、アクリロニトリルブタジエンゴム、カルボキシル基末端アクリロニトリルブタジエンゴム等)を有するゴム変性エポキシ樹脂やウレタン結合を有するウレタン変性エポキシ樹脂等が挙げられる。
これらは単独で用いてもよいし、2種以上組み合わせて用いてもよい。
Epoxy compounds (B2) include aliphatic compounds such as ethylene glycol, propylene glycol, hexanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, glycerin, diglycerin, sorbitol, spiroglycol or hydrogenated bisphenol A. Polyglycidyl ether type epoxy resin of polyol;
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 a glycidyl ether 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 acids 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 resin containing heterocycles such as triazine and hydantoin;
Examples thereof include a rubber-modified epoxy resin having a rubber skeleton (for example, polybutadiene, acrylonitrile butadiene rubber, carboxyl group-terminated acrylonitrile butadiene rubber, etc.) and a urethane-modified epoxy resin having a urethane bond in the resin skeleton.
These may be used alone or in combination of two or more.
エポキシ化合物(B2)は、流動性が高いものを用いることが好ましい。52℃における粘度が0.05Pa・s以上15Pa・s以下であることが好ましく、0.05Pa・s以上10Pa・s以下であることがより好ましく、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0.5Pa・s以下であることがより好ましい。なおここでの粘度は回転粘度計を用い、コーン・プレート:1°×R25で測定した値をいう。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。 It is preferable to use an epoxy compound (B2) having high fluidity. The viscosity at 52 ° C. is preferably 0.05 Pa · s or more and 15 Pa · s or less, more preferably 0.05 Pa · s or more and 10 Pa · s or less, and 0.05 Pa · s or more and 5 Pa · s or less. It is more preferable, and it is more preferable that it is 0.05 Pa · s or more and 0.5 Pa · s or less. The viscosity here refers to a value measured with a cone plate: 1 ° × R25 using a rotational viscometer. It is preferably an epoxy compound having a weight average molecular weight of 3000 or less.
アジリジン基含有化合物(B3)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 (B3) include N, N'-hexamethylene-1,6-bis (1-aziridinecarboxyamide) and N, N'-diphenylmethane-4,4'-bis (1-aziridine). Carboxamide), Trimethylol Propane-Tri-β-Aziridine Propionate), N, N'-Toluene-2,4-bis (1-aziridine Carboxamide), Triethylene Melamine, Trimethylol Propane-Tri- Examples thereof include β (2-methylaziridine) propionate, bisisophthaloyl-2-methylaziridine, tri-1-aziridinylphosphine oxide, and tris-1--2-methylaziridinphosphine oxide.
カルボジイミド基含有化合物(B4)としては、p−フェニレン−ビス(2,6−キシリルカルボジイミド)、テトラメチレン−ビス(t−ブチルカルボジイミド)、シクロヘキサン−1,4−ビス(メチレン−t−ブチルカルボジイミド)等のカルボジイミド基を有する化合物や、カルボジイミド基を有する重合体であるポリカルボジイミドが挙げられる。ポリカルボジイミドは例えば、イソシアネート化合物の脱二酸化炭素を伴う縮合反応により得られる。ポリカルボジイミドの合成に用いられるイソシアネート化合物は特に限定されず、例えばイソシアネート化合物(B1)として挙げたものを用いることができる。 Examples of the carbodiimide group-containing compound (B4) include p-phenylene-bis (2,6-xylylcarbodiimide), tetramethylene-bis (t-butylcarbodiimide), and cyclohexane-1,4-bis (methylene-t-butylcarbodiimide). ) And other compounds having a carbodiimide group, and polycarbodiimide which is a polymer having a carbodiimide group can be mentioned. Polycarbodiimide is obtained, for example, by a condensation reaction involving decarbonization of an isocyanate compound. The isocyanate compound used for the synthesis of polycarbodiimide is not particularly limited, and for example, those listed as the isocyanate compound (B1) can be used.
オキサゾリン基含有化合物(B5)としては、例えば、2,2’−ビス(2−オキサゾリン)、2,2’−エチレン−ビス(4,4’−ジメチル−2−オキサゾリン)、2,2’−p−フェニレン−ビス(2−オキサゾリン)、ビス(2−オキサゾリニルシクロヘキサン)スルフィド等のオキサゾリン基を有する化合物や、オキサゾリン基含有ポリマー等が挙げられる。オキサゾリン基含有ポリマーは、一般に2−ビニル−2−オキサゾリン、2−ビニル−4−メチル−2−オキサゾリン、2−イソプロペニル−2−オキサゾリン等の付加重合性オキサゾリンを重合させることにより得られる。オキサゾリン基含有ポリマーには、必要に応じて他の単量体が共重合されていてもよい。オキサゾリン基含有ポリマーの重合方法としては、特に限定されず、公知の重合方法を採用することができる。 Examples of the oxazoline group-containing compound (B5) include 2,2'-bis (2-oxazoline), 2,2'-ethylene-bis (4,4'-dimethyl-2-oxazoline), and 2,2'-. Examples thereof include compounds having an oxazoline group such as p-phenylene-bis (2-oxazoline) and bis (2-oxazoline cyclohexane) sulfide, and oxazoline group-containing polymers. The oxazoline group-containing polymer is generally obtained by polymerizing an addition-polymerizable oxazoline such as 2-vinyl-2-oxazoline, 2-vinyl-4-methyl-2-oxazoline and 2-isopropenyl-2-oxazoline. Other monomers may be copolymerized with the oxazoline group-containing polymer, if necessary. The polymerization method of the oxazoline group-containing polymer is not particularly limited, and a known polymerization method can be adopted.
ヒドラジド基含有化合物(B6)としては、アジピン酸ジヒドラジド、シュウ酸ジヒドラジド、マロン酸ジヒドラジド、コハク酸ジヒドラジド、グルタル酸ジヒドラジド、イソフタル酸ジヒドラジド、セバシン酸ジヒドラジド、マレイン酸ジヒドラジド、フマル酸ジヒドラジド、イタコン酸ジヒドラジドなどの2〜10個、特に4〜6個の炭素原子を含有するジカルボン酸ジヒドラジド;エチレン−1,2−ジヒドラジン、プロピレン−1,3−ジヒドラジン、ブチレン−1,4−ジヒドラジンなどの2〜4個の炭素原子を有する脂肪族の水溶性ジヒドラジンなどが挙げられる。 Examples of the hydrazide group-containing compound (B6) include adipic acid dihydrazide, oxalic acid dihydrazide, malonic acid dihydrazide, succi acid dihydrazide, glutarate dihydrazide, isophthalic acid dihydrazide, sebacic acid dihydrazide, maleic acid dihydrazide, and fumaric acid dihydrazide. Dicarboxylic acid dihydrazide containing 2 to 10 carbon atoms, particularly 4 to 6 carbon atoms; 2 such as ethylene-1,2-dihydrazine, propylene-1,3-dihydrazine, butylene-1,4-dihydrazine, etc. Examples thereof include aliphatic water-soluble dihydrazine having up to 4 carbon atoms.
アミノ樹脂(B7)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 (B7) include melamine resin, benzoguanamine resin, urea resin and the like.
これらの化合物は1種または2種以上を併用して用いることができる。化合物(B)としては、ポットライフ、エージング温度の観点から、イソシアネート化合物(B1)、エポキシ化合物(B2)を用いることがより好ましい。 These compounds can be used alone or in combination of two or more. As the compound (B), it is more preferable to use an isocyanate compound (B1) and an epoxy compound (B2) from the viewpoint of pot life and aging temperature.
化合物(B)の配合量は、用いる化合物(B)により適宜調整されるが、例えばイソシアネート化合物(B1)を用いる場合には、第1剤に含まれる酸基と第2剤に含まれるイソシアネート基のモル比(イソシアネート基/酸基)が0.5以上30以下となるよう配合して用いることが好ましい。 The blending amount of the compound (B) is appropriately adjusted depending on the compound (B) to be used. For example, when the isocyanate compound (B1) is used, the acid group contained in the first agent and the isocyanate group contained in the second agent are used. It is preferable to use the compound so that the molar ratio (isocyanate group / acid group) of is 0.5 or more and 30 or less.
また、化合物(B)がエポキシ化合物(B2)である場合には、第1剤に含まれる酸基と第2剤に含まれるエポキシ基のモル比(エポキシ基/酸基)が0.01以上であることが好ましく、0.1以上であることがより好ましく、0.3以上であることがより好ましく、0.6以上であることが好ましく、また1.5以下となるよう配合して用いることが好ましく、1.3以下となるよう配合して用いることが好ましい。 When the compound (B) is an epoxy compound (B2), the molar ratio (epoxy group / acid group) of the acid group contained in the first agent to the epoxy group contained in the second agent is 0.01 or more. It is preferably 0.1 or more, more preferably 0.3 or more, preferably 0.6 or more, and it is blended and used so as to be 1.5 or less. It is preferable to use the mixture so that the content is 1.3 or less.
なお、いずれの場合も酸基含有オレフィン樹脂(A1)が有する酸基が酸無水物基であり第1剤に含まれる酸基の量を酸変性率から算出する場合や、第1剤が後述する酸無水物を含み、第1剤に含まれる酸基の量を酸無水物の配合量から算出する場合(第1剤に含まれる酸基の量を実測しない場合)は酸無水物基1当量を酸基2当量として換算する。イソシアネート当量、エポキシ当量、酸価からこれらの値を算出してもよい。 In either case, the acid group of the acid group-containing olefin resin (A1) is an acid anhydride group, and the amount of the acid group contained in the first agent is calculated from the acid modification rate, or the first agent will be described later. When the amount of acid groups contained in the first agent is calculated from the blending amount of the acid anhydride (when the amount of acid groups contained in the first agent is not actually measured), the acid anhydride groups 1 Equivalents are converted as 2 equivalents of acid groups. These values may be calculated from the isocyanate equivalent, the epoxy equivalent, and the acid value.
(有機溶剤)
本発明のコーティング剤は、上記各成分に加え、さらに有機溶剤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。有機溶剤は第1剤または第2剤のいずれか一方のみに含まれていてもよいし、両方が含んでいてもよい。第1剤と第2剤とを混合する際に添加してもよい。このような有機溶剤としては、コーティング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 coating agent of the present invention can secure fluidity and exhibit appropriate coatability by further blending an organic solvent in addition to the above components. The organic solvent may be contained in only one of the first agent and the second agent, or both may be contained. It may be added when mixing the first agent and the second agent. Such an organic solvent 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 coating agent. For example, an aromatic organic solvent such as toluene or xylene; n-hexane, etc. Alicyclic organic solvents such as n-heptane; alicyclic organic solvents such as cyclohexane and methylcyclohexane; halogen-based organic solvents such as trichloroethylene, dichloroethylene, chlorobenzene and chloroform; ketone solvents such as methylethylketone, methylisobutylketone and cyclohexanone. Ester solvents such as ethyl acetate and butyl acetate; Alcohol solvents such as ethanol, methanol, n-propanol, 2-propanol (isopropyl alcohol), butanol, hexanol; diisopropyl ether, butyl cellosolve, tetrahydrofuran, dioxane, butyl carbitol, etc. Ether-based solvent; glycol ether-based solvent such as diethylene glycol monomethyl ether, triethylene glycol monomethyl ether, propylene glycol monomethyl ether; glycol ester-based solvent such as ethylene glycol monomethyl ether acetate, proprene glycol monomethyl ether acetate, diethylene glycol monoethyl ether acetate Solvents and the like may be mentioned, and these may be used alone or in combination of two or more.
酸基含有オレフィン樹脂(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、特に、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。さらに酸基含有オレフィン樹脂(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 olefin resin (A1) is excellent in solubility, it is preferable to use a mixed solvent of an alicyclic organic solvent and an ester solvent, particularly a mixed solvent of methylcyclohexane and ethyl acetate. Further, in order to improve the solubility of the acid group-containing olefin 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、イソシアネート化合物(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 isocyanate compound (B1), an aromatic organic solvent or a ketone solvent may be further 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.
また、エポキシ化合物(B2)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く、ケトン系溶剤を併用することがより好ましい。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 (B2), an aromatic organic solvent or a ketone solvent may be further used in combination with the mixed solvent of the alicyclic organic solvent and the ester solvent, and the ketone may be used. It is more preferable to use a system solvent in combination. At this time, toluene is preferably mentioned as the aromatic organic solvent, and methyl ethyl ketone is preferably mentioned as the ketone solvent.
有機溶剤の使用量としては、樹脂(A)と有機溶剤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、フィルムへの濡れ性に優れたコーティング剤とすることができる。 The amount of the organic solvent used is preferably such that the ratio of the resin (A) to the total mass of the resin (A) and the organic solvent is 5 to 30% by mass. This makes it possible to obtain a coating agent having excellent coatability and wettability to a film.
(その他の化合物)
本発明のコーティング剤は、必要に応じて酸無水物、硬化促進剤、その他(樹脂(A)以外)の樹脂、可塑剤、滑剤、ブロッキング防止剤、マット剤、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、消泡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、本発明のコーティング剤の機能を損なわない範囲内で適宜調整すればよい。
(Other compounds)
The coating agent of the present invention includes acid anhydrides, curing accelerators, other resins (other than resin (A)), plasticizers, lubricants, antiblocking agents, matting agents, thermoplastic elastomers, reactive elastomers, as required. Various additives such as phosphoric acid compounds, silane coupling agents, and antifoaming agents can be used. The content of these additives may be appropriately adjusted within a range that does not impair the function of the coating agent 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 kind or a combination of two or more kinds can be used. More specifically, for example, phthalic acid anhydride, trimellitic acid anhydride, pyromellitic acid anhydride, benzophenone tetracarboxylic acid anhydride, dodecenyl succinic anhydride, polyazipic acid anhydride, polyazereic acid anhydride, polysevacinic acid. Anhydride, poly (ethyloctadecanedioic acid) anhydride, poly (phenylhexadecanedioic acid) anhydride, tetrahydrophthalic anhydride, methyltetrahydrophthalic anhydride, methylhexahydrophthalic anhydride, hexahydrophthalic anhydride , Methylhymic acid anhydride, trialkyltetrahydrophthalic anhydride, methylcyclohexene dicarboxylic acid anhydride, methylcyclohexene tetracarboxylic acid anhydride, ethylene glycol bistrimeritate 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 succinate dianhydride, 1-methyl-dicarboxy-1,2,3,4-tetrahydro-1-naphthalene succinic hydride 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。 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.
硬化促進剤としては、用いる化合物(B)により適宜選択されるが、一例として化合物(B)がイソシアネート化合物(B1)である場合には、金属系触媒、アミン系触媒、脂肪族環状アミド化合物、チタンキレート錯体、有機リン系化合物等の触媒を用いることができる。 The curing accelerator is appropriately selected depending on the compound (B) to be used. For example, when the compound (B) is an isocyanate compound (B1), a metal-based catalyst, an amine-based catalyst, an aliphatic cyclic amide compound, etc. A catalyst such as a titanium chelate complex or an organic phosphorus compound can be used.
金属系触媒としては、金属錯体系、無機金属系、有機金属系を挙げることができ、金属錯体系として具体的には、Fe(鉄)、Mn(マンガン)、Cu(銅)、Zr(ジルコニウム)、Th(トリウム)、Ti(チタン)、Al(アルミニウム)及びCo(コバルト)からなる群より選ばれる金属のアセチルアセトナート塩であり、例えば、鉄アセチルアセトネート、マンガンアセチルアセトネート、銅アセチルアセトネート、ジルコニアアセチルアセトネート等が挙げられるが、これらのうち、毒性と触媒活性の点から、鉄アセチルアセトネート(Fe(acac)3)又はマンガンアセチルアセトネート(Mn(acac)2)が好ましい。 Examples of the metal-based catalyst include a metal complex system, an inorganic metal system, and an organic metal system. Specific examples of the metal complex system include Fe (iron), Mn (manganese), Cu (copper), and Zr (zirconium). ), Th (thorium), Ti (titanium), Al (aluminum) and Co (cobalt), which are acetylacetonate salts of metals selected from the group, for example, iron acetylacetoneate, manganese acetylacetoneate, copper acetyl. Examples thereof include acetonate and zirconia acetylacetoneate. Of these, iron acetylacetoneate (Fe (acac) 3 ) or manganese acetylacetonate (Mn (acac) 2 ) is preferable from the viewpoint of toxicity and catalytic activity. ..
無機金属系触媒としては、Fe、Mn、Cu、Zr、Th、Ti、Al及びCo等から選ばれる触媒を挙げることができる。 Examples of the inorganic metal-based catalyst include catalysts selected from Fe, Mn, Cu, Zr, Th, Ti, Al, Co and the like.
有機金属系触媒としては、スタナスジアセテート、スタナスジオクトエート、スタナスジオレエート、スタナスジラウレート、ジブチル錫オキサイド、ジブチル錫ジアセテート、ジブチル錫ジラウレート、ジブチル錫ジクロライド、ジオクチル錫ジラウレート、オクチル酸ニッケル、ナフテン酸ニッケル、オクチル酸コバルト、ナフテン酸コバルト、オクチル酸ビスマス、ナフテン酸ビスマス等が挙げられる。これらのうち好ましい化合物としては有機錫触媒であり、更に好ましくはスタナスジオクトエート、ジブチル錫ジラウレートである。 Organic metal catalysts include stanus diacetate, stanus dioctate, stanus dilaurate, stanus dilaurate, dibutyltin oxide, dibutyltin diacetate, dibutyltin dilaurate, dibutyltin dichloride, dioctyltin dilaurate, nickel octylate, etc. Examples thereof include nickel naphthenate, cobalt octylate, cobalt naphthenate, bismuth octylate, and bismuth naphthenate. Of these, preferred compounds are organotin catalysts, more preferably stanas dioctate and dibutyl tin dilaurate.
アミン触媒としては、トリエチレンジアミン、2−メチルトリエチレンジアミン、キヌクリジン、2−メチルキヌクリジン、N,N,N’,N’−テトラメチルエチレンジアミン、N,N,N’,N’−テトラメチルプロピレンジアミン、N,N,N’,N”,N”−ペンタメチルジエチレントリアミン、N,N,N’,N”,N”−ペンタメチル−(3−アミノプロピル)エチレンジアミン、N,N,N’,N”,N”−ペンタメチルジプロピレントリアミン、N,N,N’,N’−テトラメチルヘキサメチレンジアミン、ビス(2−ジメチルアミノエチル)エーテル、ジメチルエタノールアミン、ジメチルイソプロパノールアミン、ジメチルアミノエトキシエタノール、N,N−ジメチル−N’−(2−ヒドロキシエチル)エチレンジアミン、N,N−ジメチル−N’−(2−ヒドロキシエチル)プロパンジアミン、ビス(ジメチルアミノプロピル)アミン、ビス(ジメチルアミノプロピル)イソプロパノールアミン、3−キヌクリジノール、N,N,N’,N’−テトラメチルグアニジン、1,3,5−トリス(N,N−ジメチルアミノプロピル)ヘキサヒドロ−S−トリアジン、1,8−ジアザビシクロ[5.4.0]ウンデセン−7、1,5−ジアザビシクロ[4.3.0]ノネン−5、N−メチル−N’−(2−ジメチルアミノエチル)ピペラジン、N,N’−ジメチルピペラジン、ジメチルシクロヘキシルアミン、N−メチルモルホリン、N−エチルモルホリン、1−メチルイミダゾール、1,2−ジメチルイミダゾール、1−イソブチル−2−メチルイミダゾール、1−ジメチルアミノプロピルイミダゾール、N,N−ジメチルヘキサノールアミン、N−メチル−N’−(2−ヒドロキシエチル)ピペラジン、1−(2−ヒドロキシエチル)イミダゾール、1−(2−ヒドロキシプロピル)イミダゾール、1−(2−ヒドロキシエチル)−2−メチルイミダゾール、1−(2−ヒドロキシプロピル)−2−メチルイミダゾール等の3級アミン及びこれら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等が挙げられる。 As amine catalysts, triethylenediamine, 2-methyltriethylenediamine, quinuclidine, 2-methylquinuclidine, N, N, N', N'-tetramethylethylenediamine, N, N, N', N'-tetramethylpropylene Diamine, N, N, N', N ", N" -pentamethyldiethylenetriamine, N, N, N', N ", N" -pentamethyl- (3-aminopropyl) ethylenediamine, N, N, N', N ", N" -pentamethyldipropylene triamine, N, N, N', N'-tetramethylhexamethylenediamine, bis (2-dimethylaminoethyl) ether, dimethylethanolamine, dimethylisopropanolamine, dimethylaminoethoxyethanol, N, N-dimethyl-N'-(2-hydroxyethyl) ethylenediamine, N, N-dimethyl-N'-(2-hydroxyethyl) propanediamine, bis (dimethylaminopropyl) amine, bis (dimethylaminopropyl) isopropanol Amine, 3-quinucridinol, N, N, N', N'-tetramethylguanidine, 1,3,5-tris (N, N-dimethylaminopropyl) hexahydro-S-triazine, 1,8-diazabicyclo [5. 4.0] Undecene-7, 1,5-diazabicyclo [4.3.0] Nonen-5, N-methyl-N'-(2-dimethylaminoethyl) piperazine, N, N'-dimethylpiperazin, dimethylcyclohexyl Amine, N-methylmorpholin, N-ethylmorpholin, 1-methylimidazole, 1,2-dimethylimidazole, 1-isobutyl-2-methylimidazole, 1-dimethylaminopropyl imidazole, N, N-dimethylhexanolamine, N- Methyl-N'-(2-hydroxyethyl) piperazine, 1- (2-hydroxyethyl) imidazole, 1- (2-hydroxypropyl) imidazole, 1- (2-hydroxyethyl) -2-methylimidazole, 1-( Examples thereof include tertiary amines such as 2-hydroxypropyl) -2-methylimidazole and compounds obtained by converting these tertiary amines into amine salts with phenol, octyl acid, quaternized tetraphenylborate salt and the like.
脂肪族環状アミド化合物は、例えば、δ−バレロラクタム、ε−カプロラクタム、ω−エナントールラクタム、η−カプリルラクタム、β−プロピオラクタム等が挙げられる。これらの中でも硬化促進効果に優れる点からε−カプロラクタムが好ましい。 Examples of the aliphatic cyclic amide compound include δ-valerolactam, ε-caprolactam, ω-enantol lactam, η-caprilactam, β-propiolactam and the like. Among these, ε-caprolactam is preferable because it has an excellent curing promoting effect.
チタンキレート錯体は、紫外線照射により触媒活性が高められる化合物であり、脂肪族又は芳香族ジケトンをリガンドとするチタンキレート錯体であることが硬化促進効果に優れる点から好ましい。また、本発明ではリガンドとして芳香族又は脂肪族ジケトンに加え、炭素原子数2〜10のアルコールを持つものがより本発明の効果が顕著なものとなる点から好ましい。 The titanium chelate complex is a compound whose catalytic activity is enhanced by irradiation with ultraviolet rays, and a titanium chelate complex having an aliphatic or aromatic diketone as a ligand is preferable from the viewpoint of excellent curing promoting effect. Further, in the present invention, a ligand having an alcohol having 2 to 10 carbon atoms in addition to the aromatic or aliphatic diketone is preferable because the effect of the present invention becomes more remarkable.
有機リン系化合物としては、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が挙げられる。 Examples of the organophosphorus compound include tributylphosphine, methyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris (4-butylphenyl) phosphine, diphenylphosphine, phenylphosphine and the like.
化合物(B)がエポキシ化合物である場合の硬化促進剤としては、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、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のイミダゾール化合物、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。有機ホスフィン系化合物およびイミダゾール化合物からなる群から選ばれる少なくとも1種を用いることが好ましい。 When the compound (B) is an epoxy compound, the curing accelerator includes tributylphosphine, methyldiphenylphosphine, triphenylphosphine, tris (4-methylphenyl) phosphine, tris (4-butylphenyl) phosphine, diphenylphosphine, and phenyl. Organic phosphine compounds such as phosphine, 2-methylimidazole, 1,2-dimethylimidazole, 2-phenyl-4-methylimidazole, 2-ethyl-4-methylimidazole, 1-benzyl-2-methylimidazole, 1-cyanoethyl- Imidazole compounds such as 2-ethyl-4-methylimidazole, triethylamine, triethylenediamine, N'-methyl-N- (2-dimethylaminoethyl) piperazine, 1,8-diazabicyclo [5.4.0] undecene (DBU) , 1,5-diazabicyclo [4.3.0] -nonen, 6-dibutylamino-1,8-diazabicyclo [5.4.0] Undecene and other tertiary amines and these tertiary amines are phenol and octyl. Examples thereof include compounds obtained by converting an acid into an amine salt with a quaternized tetraphenylborate salt or the like, and cation catalysts such as triallyl sulfonium hexafluoroantimonate and diallyl iodonium hexafluoroantimonate. These may be used alone or in combination of two or more. It is preferable to use at least one selected from the group consisting of organic phosphine compounds and imidazole compounds.
硬化促進剤の配合量は、第1剤の樹脂(A)100質量部に対し、0.01質量部以上5質量部以下であることが好ましく、より好ましくは0.01質量部以上1質量部以下であることがより好ましく、0.01質量部以上0.5質量部以下であることがより好ましい。 The blending amount of the curing accelerator is preferably 0.01 part by mass or more and 5 parts by mass or less, and more preferably 0.01 part by mass or more and 1 part by mass with respect to 100 parts by mass of the resin (A) of the first agent. It is more preferably 0.01 parts by mass or more and 0.5 parts by mass or less.
その他の樹脂としては、例えば、ロジン系又はロジンエステル系樹脂、テルペン系又はテルペンフェノール系樹脂、飽和炭化水素樹脂、クマロン系樹脂、クマロンインデン系樹脂、スチレン系樹脂、キシレン系樹脂、フェノール系樹脂、石油系樹脂などが挙げられる。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。なかでもスチレン樹脂を用いることが好ましい。 Examples of other resins include rosin-based or rosin ester-based resins, terpene-based or terpene phenol-based resins, saturated hydrocarbon resins, kumaron-based resins, kumaron inden-based resins, styrene-based resins, xylene-based resins, and phenol-based resins. , Petroleum resin and the like. Each of these may be used alone, or two or more types may be used in combination. Of these, it is preferable to use styrene resin.
スチレン樹脂は、スチレンの単独重合体、α−メチルスチレンの単独重合体等のスチレン系モノマーの単独重合体;スチレンとα−メチルスチレンとの共重合体;スチレン及びα−メチルスチレン等のスチレン系モノマーと重合性脂肪族モノマーとの共重合体;スチレン及びα−メチルスチレン等のスチレン系モノマーと重合性芳香族モノマーとの共重合体等が挙げられる。 The styrene resin is a homopolymer of a styrene-based monomer such as a homopolymer of styrene or a homopolymer of α-methylstyrene; a copolymer of styrene and α-methylstyrene; a styrene-based polymer such as styrene and α-methylstyrene. Polymers of monomers and polymerizable aliphatic monomers; examples thereof include copolymers of styrene-based monomers such as styrene and α-methylstyrene and polymerizable aromatic monomers.
スチレン樹脂は、軟化点が80〜150℃の範囲にあるものが好ましく、90〜145℃の範囲にあるものがより好ましい。また重量平均分子量が800〜3,000の範囲にあるものが好ましい。
スチレン樹脂の配合量は、樹脂(A)100質量部に対して0.01〜1.5質量部であることが好ましい。
The styrene resin preferably has a softening point in the range of 80 to 150 ° C., and more preferably in the range of 90 to 145 ° C. Further, those having a weight average molecular weight in the range of 800 to 3,000 are preferable.
The blending amount of the styrene resin is preferably 0.01 to 1.5 parts by mass with respect to 100 parts by mass of the resin (A).
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 thereof include copolymerized hydrogenated products (SEPS), styrene block copolymers (TPS), olefin-based elastomers (TPO), and reactive elastomers obtained by acid-modifying these elastomers.
滑剤としては、オレイン酸アマイド、エルカ酸アマイド、ステアリン酸アマイド、ベヘニン酸アマイド、エチレンビスオレイン酸アマイド、エチレンビスエルカ酸アマイドなどの脂肪酸アマイド系ワックス、ライスワックス、カルナバワックス、キャンデリラワックス、ラノリンワックス、蜜蝋、鯨油、牛脂等の動植物油系ワックス、ワセリン、パラフィンワックス、マイクロクリスタリンワックス、ポリエチレンワックス、ポリプロピレンワックス、PTFEワックス、直鎖状高級アルコール等の石油系ワックス、ジメチルポリシロキサン、ジメチルポリシロキサンの側鎖のメチル基の少なくとも1つがメチル基以外の有機基(カルビノール基、ポリエーテル基、炭素原子数が2以上のアルキル基等)で置換された変性シリコーン等のシリコーン等が挙げられる。 Lubricants include fatty acid amide waxes such as oleic acid amide, erucic acid amide, stearate amide, behenic acid amide, ethylene bisoleic acid amide, and ethylene bis erucate amide, rice wax, carnauba wax, candelilla wax, and lanolin wax. , Beeswax, whale oil, animal and vegetable oil waxes such as beef fat, vaseline, paraffin wax, microcrystallin wax, polyethylene wax, polypropylene wax, PTFE wax, petroleum wax such as linear higher alcohol, dimethylpolysiloxane, dimethylpolysiloxane Examples thereof include silicones such as modified silicones in which at least one of the methyl groups in the side chain is substituted with an organic group other than the methyl group (carbinol group, polyether group, alkyl group having 2 or more carbon atoms, etc.).
ブロッキング防止剤としては、シリカ、アルミナ、酸化カルシウム、炭酸カルシウム、硫酸カルシウム、ケイ酸カルシウム、炭酸マグネシウム、沈降硫酸バリウム、クレー、カーボンブラック等の無機粒子、アクリル樹脂、ウレタン樹脂、スチレン樹脂、エポキシ樹脂、アミド樹脂、またはそれらの架橋物等の有機粒子等が挙げられる。これらは単独で用いてもよいし、複数を併用してもよい。 Examples of the blocking inhibitor include inorganic particles such as silica, alumina, calcium oxide, calcium carbonate, calcium sulfate, calcium silicate, magnesium carbonate, precipitated barium sulfate, clay, and carbon black, acrylic resin, urethane resin, styrene resin, and epoxy resin. , Amido resin, or organic particles such as crosslinked products thereof. These may be used alone or in combination of two or more.
ブロッキング防止剤は平均粒子径が0.5μm〜10μmであることが好ましく、0.5μm〜5μmであることがより好ましい。 The blocking inhibitor preferably has an average particle size of 0.5 μm to 10 μm, and more preferably 0.5 μm to 5 μm.
また、ブロッキング防止剤はコーティング剤の硬化塗膜の光沢を抑えて落ち着いた外観を作りだす、いわばマット剤としても効果を発揮する。 In addition, the blocking inhibitor suppresses the gloss of the cured coating film of the coating agent and creates a calm appearance, so to speak, it is also effective as a matting agent.
ブロッキング防止剤の配合量は、樹脂(A)とブロッキング防止剤との総量に対して50質量%以下とすることが好ましい。 The blending amount of the blocking inhibitor is preferably 50% by mass or less with respect to the total amount of the resin (A) and the blocking inhibitor.
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.
消泡剤としては、シリコーン系、非シリコーン系のいずれも用いることができ、例えばビックケミー社製BYKシリーズ(BYK−051N/052N/053N/054/055/057/063/065/066N/067A/077/081/088/088A/141/354/392/1752/1790/1791/1794/011/012/014/015/017/018/019/021/022/023/024/025/028/038/044/093/094/1610/1615/1650/1710/1711/1730/1740/1770/1780/1785/1798/A530/A555)、共栄社化学株式会社製フローレンシリーズ(AC−202/220F/247/253/265/300/300HF/300VF/303/303HF/324/326F/901/901HF/902/903/903HF/950/970MS/1160/1160HF/1170/1170HF/1190/1190HF/2000/2000HF/2200HF/2230EF/2300C、AO−5/82/98/106/108/108EF)、信越シリコーン社製KF−96、FA−630、X−50−1039A、KS−7708、KS−66、KSP−69、X−50−1105G、KS−602A、KSP−600、KS−508/530/531/537/538/540、東レ・ダウコーニング社製FSアンチフォームシリーズ(DB−110N/EPL/025/92/93/1224/1233/1277/013A)、SH5507、DK Q1−1247、AFE−1530、SM5572F、SM5571、旭化成ワッカーシリコーン社製AKシリーズ(AK−350/12500/60000)、AF98/1000、モメンティブ・パフォーマンス・マテリアルズ社製TSAシリーズ(TSA750/720/750S)等が挙げられる。 As the defoaming agent, both silicone type and non-silicone type can be used. For example, BYK series (BYK-051N / 052N / 053N / 054/055/057/063/065/066N / 067A / 077) manufactured by Big Chemie Co., Ltd. / 081/088/088A / 141/354/392/1752/1790/1791/1794/011/012/014/015/017/018/019/021/022/023/0224/025/028/0838/044 / 093/094/1610/1615/1650/1710/1711/1730/1740/1770/1780/1785/1798/A530/A555, Floren series manufactured by Kyoeisha Chemical Co., Ltd. (AC-202 / 220F / 247/253 / 265/300/300HF / 300VF / 303/303HF / 324/326F / 901/901HF / 902/903/903HF / 950/970MS / 1160/1160HF / 1170/1170HF / 1190/1190HF / 2000/2000HF / 2200HF / 2230EF / 2300C, AO-5 / 82/98/106/108 / 108EF), KF-96, FA-630, X-50-1039A, KS-7708, KS-66, KSP-69, X-50 manufactured by Shinetsu Silicone Co., Ltd. -1105G, KS-602A, KSP-600, KS-508 / 530/531/537/538/540, Toray Dow Corning FS Antifoam Series (DB-110N / EPL / 025/92/93/1224 / 1233/1277 / 013A), SH5507, DK Q1-1247, AFE-1530, SM5572F, SM5571, Asahi Kasei Wacker Silicone AK series (AK-350 / 12500/60000), AF98 / 1000, Momentive Performance Materials Examples include the TSA series manufactured by TSA750 / 720 / 750S.
これらの成分は、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を混合する際に添加してもよい。 These components may be pre-blended in the first agent or the second agent, or may be added when the first agent and the second agent are mixed.
上述した各成分を混合することにより本発明のコーティング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コーティング剤としてもよいが、化合物(B)(第2剤)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、コーティング剤の使用時に硬化剤(B)を混合する2液型のコーティング剤とすることがコーティング剤の安定性、作業性に優れることから好ましい。 The coating agent 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 a coating agent, but components other than the compound (B) (second agent) may be mixed in advance to adjust the mixture, and when the coating agent is used, a curing agent (cure agent) ( It is preferable to use a two-component coating agent in which B) is mixed because the coating agent is excellent in stability and workability.
本発明のコーティング剤は、薄膜でありながら水蒸気バリア性に優れたコーティング層を簡便な装置で容易に形成することができる。 The coating agent of the present invention can easily form a coating layer which is a thin film but has excellent water vapor barrier properties by a simple device.
<積層体>
本発明の積層体は、基材に本発明のコーティング剤を塗布したものである。本発明のコーティング剤は各種基材への塗工性に優れ、紙、合成紙、熱可塑性樹脂フィルム、鋼板、アルミ箔、木材、織布、編布、不織布、石膏ボード、木質ボード等への塗工または含浸に使用でき、溶剤を除去することでコーティング層を形成することができる。中でも、紙、合成紙、熱可塑性樹脂フィルムに用いることが好ましい。
<Laminated body>
The laminate of the present invention is obtained by applying the coating agent of the present invention to a base material. The coating agent of the present invention has excellent coatability on various substrates, and can be applied to paper, synthetic paper, thermoplastic resin film, steel plate, aluminum foil, wood, woven fabric, knitted fabric, non-woven fabric, gypsum board, wood board, etc. It can be used for coating or impregnation, and a coating layer can be formed by removing the solvent. Above all, it is preferably used for paper, synthetic paper, and thermoplastic resin film.
熱可塑性樹脂フィルムとしては、例えば、食品用途として汎用されるポリエチレンテレフタレート(PET)フィルム、ポリスチレンフィルム、ポリアミドフィルム、ポリアクリロニトリルフィルム、ポリエチレンフィルム(LLDPE:低密度ポリエチレンフィルム、HDPE:高密度ポリエチレンフィルム)やポリプロピレンフィルム(CPP:無延伸ポリプロピレンフィルム、OPP:二軸延伸ポリプロピレンフィルム)等のポリオレフィンフィルム、ポリビニルアルコールフィルム、エチレン−ビニルアルコール共重合体フィルム等が挙げられる。これらは延伸処理を施してあってもよい。延伸処理方法としては、押出成膜法等で樹脂を溶融押出してシート状にした後、同時二軸延伸或いは逐次二軸延伸を行うことが一般的である。また、逐次二軸延伸の場合は、はじめに縦延伸処理を行い、次に横延伸を行うことが一般的である。具体的にはロール間の速度差を利用した縦延伸とテンターを用いた横延伸を組み合わせる方法が多く用いられる。更にこれら積層用のフィルムにアルミニウム、ステンレス等の金属、或いはシリカやアルミナ等の金属酸化物の蒸着層を積層したフィルムを用いても良い。 Examples of the thermoplastic resin film include polyethylene terephthalate (PET) film, polystyrene film, polyamide film, polyacrylonitrile film, polyethylene film (LLDPE: low density polyethylene film, HDPE: high density polyethylene film), which are widely used for food applications. Examples thereof include a polyolefin film such as a polypropylene film (CPP: unstretched polypropylene film, OPP: biaxially stretched polypropylene film), a polyvinyl alcohol film, an ethylene-vinyl alcohol copolymer film and the like. These may be stretched. As a stretching treatment method, it is common to melt-extrude the resin by an extrusion film forming method or the like to form a sheet, and then perform simultaneous biaxial stretching or sequential biaxial stretching. Further, in the case of sequential biaxial stretching, it is common to first perform longitudinal stretching treatment and then lateral stretching. Specifically, a method of combining longitudinal stretching using the speed difference between rolls and transverse stretching using a tenter is often used. Further, a film obtained by laminating a vapor-deposited layer of a metal such as aluminum or stainless steel or a metal oxide such as silica or alumina may be used on the film for laminating.
また、産業用途として汎用されるポリカーボネート、ポリエチレンテレフタレート、ポリメチルメタクリレート、ポリスチレン、ポリエステル、ポリオレフィン、エポキシ樹脂、メラミン樹脂、トリアセチルセルロース樹脂、ポリビニルアルコール、ABS樹脂、ノルボルネン系樹脂、環状オレフィン系樹脂、ポリイミド樹脂、ポリフッ化ビニル樹脂、ポリフッ化ビニリデン樹脂、エチレン−酢酸ビニル共重合体等からなるフィルムも挙げられる。
また、基材フィルムの厚さも特に限定されるものではないが、通常は1〜500μmの範囲であればよい。
In addition, polycarbonate, polyethylene terephthalate, polymethyl methacrylate, polystyrene, polyester, polyolefin, epoxy resin, melamine resin, triacetyl cellulose resin, polyvinyl alcohol, ABS resin, norbornene resin, cyclic olefin resin, and polyimide, which are widely used for industrial purposes. Examples thereof include a film made of a resin, a polyvinyl fluoride resin, a vinylidene fluoride resin, an ethylene-vinyl acetate copolymer and the like.
Further, the thickness of the base film is not particularly limited, but usually it may be in the range of 1 to 500 μm.
さらにこれらの基材の2種以上を、接着剤を用いて貼り合せた積層体に本発明のコーティング剤を塗布してもよい。本発明のコーティング剤は、水蒸気バリア性、耐溶剤性に優れるため、例えば基材同士を貼り合せる接着層に水蒸気や溶剤が浸入するのを防ぐことができ、積層体の接着強度を長期にわたって維持することもできる。 Further, the coating agent of the present invention may be applied to a laminate obtained by laminating two or more of these base materials using an adhesive. Since the coating agent of the present invention is excellent in water vapor barrier property and solvent resistance, for example, it is possible to prevent water vapor and solvent from infiltrating into the adhesive layer for bonding the base materials, and maintain the adhesive strength of the laminated body for a long period of time. You can also do it.
より具体的な積層体の構成としては、
(1)基材フィルム1/接着層1/シーラントフィルム
(2)基材フィルム1/接着層1/金属蒸着未延伸フィルム
(3)基材フィルム1/接着層1/金属蒸着延伸フィルム
(4)透明蒸着延伸フィルム/接着層1/シーラントフィルム
(5)基材フィルム1/接着層1/基材フィルム2/接着層2/シーラントフィルム
(6)基材フィルム1/接着層1/金属蒸着延伸フィルム/接着層2/シーラントフィルム
(7)基材フィルム1/接着層1/透明蒸着延伸フィルム/接着層2/シーラントフィルム
(8)基材フィルム1/接着層1/金属層/接着層2/シーラントフィルム
(9)基材フィルム1/接着層1/基材フィルム2/接着層2/金属層/接着層3/シーラントフィルム
(10)基材フィルム1/接着層1/金属層/接着層2/基材フィルム2/接着層3/シーラントフィルム
(11)基材フィルム1/接着層1/基材フィルム2
等が挙げられるがこれに限定されない。
As a more specific structure of the laminated body,
(1) Base film 1 / Adhesive layer 1 / Sealant film (2) Base film 1 / Adhesive layer 1 / Metal vapor deposition unstretched film (3) Base film 1 / Adhesive layer 1 / Metal vapor deposition stretched film (4) Transparent vapor-deposited stretched film / adhesive layer 1 / sealant film (5) Base film 1 / adhesive layer 1 / base film 2 / adhesive layer 2 / sealant film (6) Base film 1 / adhesive layer 1 / metal vapor-deposited stretched film / Adhesive layer 2 / Sealant film (7) Base film 1 / Adhesive layer 1 / Transparent vapor deposition stretched film / Adhesive layer 2 / Sealant film (8) Base film 1 / Adhesive layer 1 / Metal layer / Adhesive layer 2 / Sealant Film (9) Base film 1 / Adhesive layer 1 / Base film 2 / Adhesive layer 2 / Metal layer / Adhesive layer 3 / Sealant film (10) Base film 1 / Adhesive layer 1 / Metal layer / Adhesive layer 2 / Base film 2 / Adhesive layer 3 / Sealant film (11) Base film 1 / Adhesive layer 1 / Base film 2
Etc., but are not limited to this.
構成(1)に用いられる基材フィルム1としては、OPPフィルム、PETフィルム、ポリアミドフィルム等が挙げられる。また、基材フィルム1としてガスバリア性や、後述する印刷層を設ける際のインキ受容性の向上等を目的としたコーティングが施されたものを用いてもよい。コーティングが施された基材フィルム1の市販品としては、K−OPPフィルムやK−PETフィルム等が挙げられる。シーラントフィルムとしては、CPPフィルム、LLDPEフィルム等が挙げられる。基材フィルム1の接着層1側の面(基材フィルム1としてコーティングが施されたものを用いる場合には、コーティング層の接着層1側の面)に、印刷層を設けてもよい。印刷層は、グラビアインキ、フレキソインキ、オフセットインキ、孔版インキ、インクジェットインク等各種印刷インキにより、従来ポリマーフィルムへの印刷に用いられてきた一般的な印刷方法で形成される。 Examples of the base film 1 used in the configuration (1) include an OPP film, a PET film, and a polyamide film. Further, as the base film 1, a film having a gas barrier property and a coating for improving ink acceptability when providing a printing layer described later may be used. Examples of commercially available products of the coated base film 1 include K-OPP film and K-PET film. Examples of the sealant film include a CPP film and an LLDPE film. A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side (when a coated film is used as the base film 1, the surface of the coating layer on the adhesive layer 1 side). The printing layer is formed by various printing inks such as gravure ink, flexo ink, offset ink, stencil ink, and inkjet ink by a general printing method conventionally used for printing on a polymer film.
構成(2)、(3)に用いられる基材フィルム1としては、OPPフィルムやPETフィルム等が挙げられる。金属蒸着未延伸フィルムとしては、CPPフィルムにアルミニウム等の金属蒸着を施したVM−CPPフィルムを、金属蒸着延伸フィルムとしては、OPPフィルムにアルミニウム等の金属蒸着を施したVM−OPPフィルムを用いることができる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 used in the configurations (2) and (3) include an OPP film and a PET film. As the metal-deposited unstretched film, a VM-CPP film in which a metal such as aluminum is vapor-deposited on a CPP film is used, and as a metal-deposited stretched film, a VM-OPP film in which a metal such as aluminum is vapor-deposited on an OPP film is used. Can be done. A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(4)に用いられる透明蒸着延伸フィルムとしては、OPPフィルム、PETフィルム、ポリアミドフィルム等にシリカやアルミナ蒸着を施したフィルムが挙げられる。シリカやアルミナの無機蒸着層の保護等を目的として、蒸着層上にコーティングが施されたフィルムを用いてもよい。シーラントフィルムは構成(1)と同様のものが挙げられる。透明蒸着延伸フィルムの接着層1側の面(無機蒸着層上にコーティングが施されたものを用いる場合には、コーティング層の接着層1側の面)に印刷層を設けてもよい。印刷層の形成方法は構成(1)と同様である。 Examples of the transparent vapor-deposited stretched film used in the configuration (4) include a film obtained by subjecting silica or alumina vapor deposition to an OPP film, PET film, polyamide film or the like. A film coated on the vapor-deposited layer may be used for the purpose of protecting the inorganic vapor-deposited layer of silica or alumina. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the transparent vapor-deposited stretched film on the adhesive layer 1 side (in the case of using a coating on the inorganic thin-film film, the surface on the adhesive layer 1 side of the coating layer). The method of forming the print layer is the same as that of the configuration (1).
構成(5)に用いられる基材フィルム1としては、PETフィルム等が挙げられる。基材フィルム2としては、ポリアミドフィルム等が挙げられる。シーラントフィルムは構成(1)と同様のものが挙げられる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 used in the configuration (5) include a PET film and the like. Examples of the base film 2 include a polyamide film and the like. Examples of the sealant film include those having the same structure (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(6)の基材フィルム1としては、構成(2)、(3)と同様のものが挙げられる。金属蒸着延伸フィルムとしては、OPPフィルムやPETフィルムにアルミニウム等の金属蒸着を施したVM−OPPフィルムやVM−PETフィルムが挙げられる。シーラントフィルムは構成(1)と同様のものが挙げられる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 of the configuration (6) include those similar to the configurations (2) and (3). Examples of the metal-deposited stretched film include a VM-OPP film and a VM-PET film in which a metal such as aluminum is vapor-deposited on an OPP film or a PET film. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(7)の基材フィルム1としては、PETフィルム等が挙げられる。透明蒸着延伸フィルムとしては、構成(4)と同様のものが挙げられる。シーラントフィルムは構成(1)と同様のものが挙げられる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 of the configuration (7) include a PET film and the like. Examples of the transparent vapor-deposited stretched film include those similar to the configuration (4). Examples of the sealant film include those having the same structure (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(8)の基材フィルム1としては、PETフィルム、ポリアミドフィルム等が挙げられる。金属層としては、アルミニウム箔等が挙げられる。シーラントフィルムは構成(1)と同様のものが挙げられる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 of the configuration (8) include a PET film and a polyamide film. Examples of the metal layer include aluminum foil. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(9)、(10)の基材フィルム1としては、PETフィルム等が挙げられる。基材フィルム2としては、ポリアミドフィルム等が挙げられる。金属層としては、アルミニウム箔等が挙げられる。シーラントフィルムは構成(1)と同様のものが挙げられる。構成(1)と同様にして、基材フィルム1の接着層1側の面に印刷層を設けてもよい。 Examples of the base film 1 having the configurations (9) and (10) include a PET film and the like. Examples of the base film 2 include a polyamide film and the like. Examples of the metal layer include aluminum foil. Examples of the sealant film are the same as those in the configuration (1). A printing layer may be provided on the surface of the base film 1 on the adhesive layer 1 side in the same manner as in the configuration (1).
構成(11)の基材フィルム1としては、PETフィルム等が挙げられる。基材フィルム2としては、PETフィルム、ポリフッ化ビニリデンフィルム等が挙げられる。 Examples of the base film 1 of the configuration (11) include a PET film and the like. Examples of the base film 2 include a PET film and a polyvinylidene fluoride film.
これらの構成において、本発明のコーティング剤は例えば基材フィルム1の外側(基材フィルム1のシーラントフィルムが配置されるのとは反対側の面)に塗布されるが、その他の位置にコーティング層が配置されていてもよい。 In these configurations, the coating agent of the present invention is applied, for example, to the outside of the base film 1 (the surface opposite to the side where the sealant film of the base film 1 is arranged), but the coating layer is applied at other positions. May be arranged.
さらに、未延伸フィルムに本発明のコーティング剤を塗布し、そのコートフィルムを延伸する、いわゆるインラインコートを行ってもよい。 Further, the coating agent of the present invention may be applied to the unstretched film and the coated film may be stretched, so-called in-line coating.
また、熱可塑性樹脂フィルムには、コロナ放電処理がされていることが好ましい。シリカ、アルミナ等が蒸着されていてもよく、酸素ガスバリア層等のガスバリアコート層が積層されていてもよい。 Further, it is preferable that the thermoplastic resin film is subjected to a corona discharge treatment. Silica, alumina, etc. may be vapor-deposited, or a gas barrier coat layer such as an oxygen gas barrier layer may be laminated.
基材として紙を用いた場合には、防湿紙とすることができる。基材紙としては、クラフト紙、ライナー紙、アート紙、コート紙、カートン紙等を挙げることができる。 When paper is used as the base material, it can be a moisture-proof paper. Examples of the base paper include kraft paper, liner paper, art paper, coated paper, carton paper and the like.
また、基材として合成紙を用いた場合には、防湿合成紙とすることができる。合成紙の構造は、特に限定されない。したがって、単層構造であっても多層構造であってもよい。多層構造としては、例えば基材層と表面層の2層構造、基材層と表裏面に表面層が存在する3層構造、基材層と表面層の間に他の樹脂フィルム層が存在する多層構造を例示することができる。また、各層は無機や有機のフィラーを含有していてもよいし、含有していなくてもよい。また、微細なボイドを多数有する微多孔性合成紙も使用することができる。 When synthetic paper is used as the base material, it can be a moisture-proof synthetic paper. The structure of the synthetic paper is not particularly limited. Therefore, it may have a single-layer structure or a multi-layer structure. As the multilayer structure, for example, there are a two-layer structure of a base material layer and a surface layer, a three-layer structure in which a base material layer and a surface layer exist on the front and back surfaces, and another resin film layer between the base material layer and the surface layer. A multi-layer structure can be exemplified. Further, each layer may or may not contain an inorganic or organic filler. Further, a microporous synthetic paper having a large number of fine voids can also be used.
本発明のコーティング剤を基材に塗工する方法は特に限定されるものではないが、グラビアロールコーティング、リバースロールコーティング、ワイヤーバーコーティング、リップコーティング、エアナイフコーティング、カーテンフローコーティング、スプレーコーティング、浸漬コーティング、はけ塗り法等が採用できる。コーティング剤の塗布量は基材によって適宜決定すればよい。本発明におけるコーティング層の厚みは、基材が熱可塑性樹脂フィルムの場合、水蒸気バリア性を十分高めるためには少なくとも0.1μmより厚くすることが望ましい。水蒸気バリア性の点からは、コーティング層の厚みは厚いほうがよいが、本発明の特徴はコーティング層の厚みが薄くても水蒸気バリア性を発現する点にあり、そのため本発明のコーティング剤を用いれば、基材の特徴を活かしつつ、水蒸気バリア性を高めることができる。よって本発明のコーティング層の厚みは0.1μ、〜10μmであることが好ましく、0.2μ〜8μmがより好ましく、0.3μ〜7μmが特に好ましい。 The method of applying the coating agent of the present invention to the substrate is not particularly limited, but gravure roll coating, reverse roll coating, wire bar coating, lip coating, air knife coating, curtain flow coating, spray coating, dip coating. , Brush coating method, etc. can be adopted. The amount of the coating agent applied may be appropriately determined depending on the base material. When the base material is a thermoplastic resin film, the thickness of the coating layer in the present invention is preferably at least 0.1 μm or more in order to sufficiently enhance the water vapor barrier property. From the viewpoint of water vapor barrier property, the thickness of the coating layer should be thick, but the feature of the present invention is that the water vapor barrier property is exhibited even if the thickness of the coating layer is thin. Therefore, if the coating agent of the present invention is used, , The water vapor barrier property can be enhanced while taking advantage of the characteristics of the base material. Therefore, the thickness of the coating layer of the present invention is preferably 0.1 μm and 10 μm, more preferably 0.2 μm to 8 μm, and particularly preferably 0.3 μm to 7 μm.
また、基材が紙、織布、編布、不織布等のコーティング剤がしみ込むようなものの場合、塗布量を膜厚で評価することが難しいため、乾燥後の塗布質量で評価する。乾燥後の塗布質量が1〜200g/m2の範囲であればよい。 Further, when the base material is such that a coating agent such as paper, woven fabric, knitted fabric, or non-woven fabric soaks in, it is difficult to evaluate the coating amount by the film thickness, so the evaluation is performed by the coating mass after drying. The coating mass after drying may be in the range of 1 to 200 g / m 2.
本発明のコーティング剤を基材に塗布した後、溶剤を乾燥させる際の乾燥温度は40℃〜150℃が好ましく、40〜130℃がより好ましく、40〜120℃がより好ましい。乾燥後、さらに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時間〜240時間で適宜調整すればよい。 After applying the coating agent of the present invention to the substrate, the drying temperature at which the solvent is dried is preferably 40 ° C. to 150 ° C., more preferably 40 to 130 ° C., and even more preferably 40 to 120 ° C. After drying, it is preferable to further provide an aging step. The aging conditions may be appropriately adjusted from 25 ° C. to 100 ° C. for 12 hours to 240 hours.
エージング温度は酸基含有オレフィン樹脂(A1)の融点よりも5℃以上高いことが好ましく、10℃以上高いことがより好ましい。これにより、コーティング剤がより濡れ広がりやすく、また硬化塗膜中における結晶化部位の比率をより高めることができ、密着性、耐溶剤性、水蒸気バリア性に優れたコーティング剤とすることができる。エージング温度の上限は特に限定されないが、省エネルギーの観点から一例として酸基含有オレフィン樹脂(A1)の融点との差が30℃以下であることが好ましい。 The aging temperature is preferably 5 ° C. or higher, more preferably 10 ° C. or higher, higher than the melting point of the acid group-containing olefin resin (A1). As a result, the coating agent can be more easily wetted and spread, and the ratio of crystallized portions in the cured coating film can be further increased, so that the coating agent can be excellent in adhesion, solvent resistance, and water vapor barrier property. The upper limit of the aging temperature is not particularly limited, but from the viewpoint of energy saving, as an example, the difference from the melting point of the acid group-containing olefin resin (A1) is preferably 30 ° C. or less.
また、本発明のコーティング剤で処理した積層体のコーティング層上に、さらに別の基材を貼り合せてもよい。組み合わせることのできる基材としては、熱可塑性樹脂フィルム、紙、合成紙、木材、織布、編布、不織布など、既述した基材の他、アルミニウム等の金属箔など、適宜選んで使用することができ、同一のものでも異なるものでもよい。また、本発明の積層体同士を組み合わせてもよい。 Further, another base material may be laminated on the coating layer of the laminate treated with the coating agent of the present invention. As the base material that can be combined, in addition to the above-mentioned base materials such as thermoplastic resin film, paper, synthetic paper, wood, woven cloth, knitted cloth, and non-woven fabric, metal foil such as aluminum is appropriately selected and used. It can be the same or different. Further, the laminated bodies of the present invention may be combined with each other.
別の基材の貼り合せる方法としては、接着剤を介してコーティング層と別の基材を貼り合せてもよいし、コーティング層上に押出しラミネート等によって別の基材を積層してもよい。 As a method of laminating another base material, the coating layer and another base material may be bonded to each other via an adhesive, or the other base material may be laminated on the coating layer by extrusion lamination or the like.
<包装材、加工品>
本発明の積層体は水蒸気バリア性に優れるため、例えば、紙コップ、防湿ダンボール、防湿紙、水蒸気バリアフィルム等の用途や水滴や湿気を嫌うものの包装や、ウェットティッシュなど内部の水分が外部に拡散するのを防ぐ必要があるものの包装、太陽電池のフロントシートやバックシートなど長期に亘って使用するため湿気による基材の劣化を防ぐ必要がある用途など、多様な用途に使用することができる。
<Packaging materials, processed products>
Since the laminate of the present invention has excellent water vapor barrier properties, for example, it is used for paper cups, moisture-proof cardboard, moisture-proof paper, water vapor barrier film, packaging of things that dislike water droplets and moisture, and internal moisture such as wet tissue diffuses to the outside. It can be used for various purposes such as packaging for items that need to be prevented from being damaged, and applications that need to prevent deterioration of the base material due to moisture because it is used for a long period of time such as front seats and back sheets of solar cells.
また本発明の積層体は耐溶剤性にも優れるため、シャンプーやリンスなどの包装材にも好ましく用いることができる。このような内容物は接着層を劣化させ、接着強度の低下を招くおそれがあるが、接着層と内容物との間に本発明のコーティング剤によるコーティング層が設けられていれば、接着層の劣化を抑制することができる。 Further, since the laminate of the present invention is also excellent in solvent resistance, it can be preferably used as a packaging material such as shampoo and conditioner. Such contents may deteriorate the adhesive layer and cause a decrease in adhesive strength. However, if a coating layer using the coating agent of the present invention is provided between the adhesive layer and the contents, the adhesive layer can be used. Deterioration can be suppressed.
また、本発明の積層体を成型加工して、例えば食品、医療品、日用品を収容するプレススルーパッケージやストリップパッケージ、電池の外装材用包装材、コンデンサの外装材用包装材等、種々の用途の好適に用いることができる。 Further, the laminate of the present invention is molded and processed into various uses such as press-through packages and strip packages for accommodating foods, medical products, and daily necessities, packaging materials for battery exterior materials, and packaging materials for capacitor exterior materials. Can be preferably used.
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.
<測定方法>
(酸価)
本実施例において、酸基含有オレフィン樹脂(A1)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り、特記しない限り単位はmgKOH/g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。
<Measurement method>
(Acid value)
In this example, the acid value of the acid group-containing olefin resin (A1) is a coefficient obtained from a calibration line prepared by using FT-IR (manufactured by Nippon Kogaku Co., Ltd., FT-IR4200) with a chloroform solution of maleic anhydride. (F), 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 acid in the maleic anhydride-modified polyolefin solution. It is a value calculated by the following formula using the above formula, and the unit is mgKOH / g unless otherwise specified. In the following formula, the molecular weight of maleic anhydride was 98.06, and the molecular weight of potassium hydroxide was 56.11.
(結晶化温度、結晶化熱量)
酸基含有オレフィン樹脂(A1)とエポキシ化合物との硬化物の結晶化温度はJIS−K−7121に、結晶化熱量はJIS−K−7122に従って測定した。特記しない限り結晶化温度の単位は℃であり、結晶化熱量の単位はmJ/mgである。
(Crystallization temperature, calorific value of crystallization)
The crystallization temperature of the cured product of the acid group-containing olefin resin (A1) and the epoxy compound was measured according to JIS-K-7121, and the calorific value of crystallization was measured according to JIS-K-7122. Unless otherwise specified, the unit of crystallization temperature is ° C., and the unit of calorific value for crystallization is mJ / mg.
(融点、融解熱量)
酸基含有オレフィン樹脂の融点はJIS−K−7121に、融解熱量はJIS−K−7122に従って測定した。特記しない限り融点の単位は℃であり、融解熱量の単位はmJ/mgである。
(Melting point, heat of fusion)
The melting point of the acid group-containing olefin resin was measured according to JIS-K-7121, and the amount of heat of fusion was measured according to JIS-K-7122. Unless otherwise specified, the unit of melting point is ° C. and the unit of heat of fusion is mJ / mg.
実際の測定条件は以下の通りである。
装置:X−DSC7000AS−3DX(日立ハイテクサイエンス社製)
容器:オープン型アルミ製容器(カバーあり、日立ハイテクサイエンス社製)
試料:3.5mg
リファレンス:空容器
雰囲気:窒素ガスフロー 20ml/min
測定温度:−50℃(10min保持)→10℃/min→150℃(10min保持)→−10℃/min→−50℃(10min保持)→10℃/min→150℃(10min保持)
The actual measurement conditions are as follows.
Equipment: X-DSC7000AS-3DX (manufactured by Hitachi High-Tech Science)
Container: Open type aluminum container (with cover, manufactured by Hitachi High-Tech Science Corporation)
Sample: 3.5 mg
Reference: Empty container Atmosphere: Nitrogen gas flow 20 ml / min
Measurement temperature: -50 ° C (holding 10 min) → 10 ° C / min → 150 ° C (holding 10 min) → -10 ° C / min → -50 ° C (holding 10 min) → 10 ° C / min → 150 ° C (holding 10 min)
150℃から−50℃に降温する過程で結晶化ピークが観測された場合はその頂点を結晶化温度とし、その後−50℃から150℃に昇温する過程で冷結晶化による結晶化ピークが観測された場合はその頂点を結晶化温度とした。結晶化ピークとベースラインで区切られた面積から結晶化熱量を算出した。
また、−50℃から150℃に昇温する過程で観測された融解ピークの頂点を融解温度とし、融解ピークとベースラインで区切られた面積から融解熱量を算出した。
If a crystallization peak is observed in the process of lowering the temperature from 150 ° C to -50 ° C, the peak is set as the crystallization temperature, and then a crystallization peak due to cold crystallization is observed in the process of raising the temperature from -50 ° C to 150 ° C. If so, the apex was taken as the crystallization temperature. The calorific value of crystallization was calculated from the area separated by the crystallization peak and the baseline.
Further, the apex of the melting peak observed in the process of raising the temperature from −50 ° C. to 150 ° C. was defined as the melting temperature, and the amount of heat of melting was calculated from the area separated by the melting peak and the baseline.
<酸基含有オレフィン樹脂(A1)>
以下の無水マレイン酸変性プロピレン−ブテン共重合体を酸変性オレフィン樹脂(A1−1)〜(A1−4)として用いた。酸変性オレフィン樹脂(A1−1)〜(A1−4)とデナコール(登録商標)EX−321Lとを、エポキシ過剰率をそれぞれ以下の値とした硬化物について結晶化温度、結晶化熱量を測定し、表2にまとめた。なお表2において結晶化温度の数値に括弧を付した値は冷結晶化温度であり、JIS−K−7121に記載の方法では結晶化ピークが観測されず、融点を測定した際に結晶化ピークが観測されたことを意味する。結晶化熱量の数値に括弧を付した値は冷結晶化による結晶化ピークから算出した結晶化熱量であることを意味する。
<Acid group-containing olefin resin (A1)>
The following maleic anhydride-modified propylene-butene copolymers were used as acid-modified olefin resins (A1-1) to (A1-4). The crystallization temperature and calorific value of crystallization were measured for the cured products of the acid-modified olefin resins (A1-1) to (A1-4) and Denacol® EX-321L with the epoxy excess ratio set to the following values, respectively. , Table 2. In Table 2, the values in parentheses in the numerical values of the crystallization temperature are the cold crystallization temperature, and the crystallization peak is not observed by the method described in JIS-K-7121, and the crystallization peak is measured when the melting point is measured. Means that was observed. The value in parentheses in the numerical value of the calorific value of crystallization means that it is the calorific value of crystallization calculated from the crystallization peak by cold crystallization.
<化合物(B)>
以下のイソシアネート化合物(B1)、エポキシ化合物(B2)を化合物(B)として用いた。
(イソシアネート化合物(B1−1))
トルエンジイソシアネートのトリメチロールプロパンアダクト体
(イソシアネート化合物(B1−2))
デスモジュール(登録商標)N3300(住化コベストロウレタン(株)社製、ヌレート型型ヘキサメチレンジイソシアネート)
(エポキシ化合物(B2−1))
デナコール(登録商標)EX−321L(ナガセケムテックス(株)製、トリメチロールプロパンポリグリシジルエーテル、エポキシ当量130)
<Compound (B)>
The following isocyanate compound (B1) and epoxy compound (B2) were used as the compound (B).
(Isocyanate compound (B1-1))
Trimethylolpropane adduct of toluene diisocyanate (isocyanate compound (B1-2))
Death Module (registered trademark) N3300 (Nurate type hexamethylene diisocyanate manufactured by Sumika Cobestro Urethane Co., Ltd.)
(Epoxy compound (B2-1))
Denacol® EX-321L (manufactured by Nagase ChemteX Corporation, trimethylolpropane polyglycidyl ether, epoxy equivalent 130)
<コーティング剤の調整>
(実施例1)
酸変性オレフィン樹脂(A1−1)溶液:70質量部(固形分25%)、脂肪族アマイド(固形分25質量%、メチルシクロヘキサン:酢酸エチル=1:1の混合溶液を使用):1.6質量部、スチレン樹脂(スチレン系モノマーの単独重合体、重量平均分子量1500):2.5質量部、不揮発分100%のヌレート型ヘキサメチレンジイソシアネート:2.0質量部、酢酸エチルをよく撹拌して実施例1のコーティング剤を調整した。
<Adjustment of coating agent>
(Example 1)
Acid-modified olefin resin (A1-1) solution: 70 parts by mass (solid content 25%), aliphatic amide (using a mixed solution of solid content 25% by mass, methylcyclohexane: ethyl acetate = 1: 1): 1.6 By mass, styrene resin (monopolymer of styrene-based monomer, weight average molecular weight 1500): 2.5 parts by mass, 100% non-volatile content nurate-type hexamethylene diisocyanate: 2.0 parts by mass, ethyl acetate is well stirred. The coating agent of Example 1 was prepared.
(実施例2−6)、(比較例1−3)
用いる成分やその配合量を表3、表4に示すように変更した以外は実施例1と同様にして実施例2−6、比較例1−3のコーティング剤を調整した。
(Example 2-6), (Comparative Example 1-3)
The coating agents of Examples 2-6 and Comparative Example 1-3 were prepared in the same manner as in Example 1 except that the components used and the blending amounts thereof were changed as shown in Tables 3 and 4.
なお、表中に記載のうち上記で説明のない化合物の詳細は以下の通りである。
(シリカ)
平均粒子径が1.7μmの湿式シリカ
(カーボネート)
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
The details of the compounds described in the table that are not described above are as follows.
(silica)
Wet silica (carbonate) with an average particle size of 1.7 μm
Ethylene carbonate: Ethylmethyl carbonate: Dimethyl carbonate = 1: 1: 1
<積層体>
(実施例1)
実施例1のコーティング剤を二軸延伸ナイロンフィルム(膜厚:15μm)のコロナ処理面にバーコーターで塗布量3.0g/m2(dry)で塗布し、80℃−1分間で乾燥させた後、40℃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 coating agent of Example 1 was applied to the corona-treated surface of a biaxially stretched nylon film (film thickness: 15 μm) with a bar coater at a coating amount of 3.0 g / m 2 (dry), and dried at 80 ° C. for 1 minute. After that, curing (aging) was carried out at 40 ° C. for 3 days to obtain a laminate of Example 1.
(実施例2−6)、(比較例1−3)
用いるコーティング剤を変更した他は実施例1と同様にして実施例2−6、比較例1−3の積層体を得た。
(Example 2-6), (Comparative Example 1-3)
Laminates of Examples 2-6 and Comparative Example 1-3 were obtained in the same manner as in Example 1 except that the coating agent used was changed.
<評価>
以下のようにして実施例1−6、比較例1−3の積層体を評価し、結果を表3、表4にまとめた。
(基材密着性)
コーティング層にセロハンテープ(ニチバン社製TF−12)を圧着し、テープを一気に剥がした時の剥がれの程度を目視で判断し、3段階で評価した。
〇:剥がれなし
△:一部剥がれた
×:全て剥がれた
<Evaluation>
The laminates of Examples 1-6 and Comparative Example 1-3 were evaluated as follows, and the results are summarized in Tables 3 and 4.
(Adhesion to base material)
Cellophane tape (TF-12 manufactured by Nichiban Co., Ltd.) was pressure-bonded to the coating layer, and the degree of peeling when the tape was peeled off at once was visually judged and evaluated on a three-point scale.
〇: No peeling △: Partially peeled ×: All peeled
(インキ受容性)
寺西化学工業社製マジックインキNo.500(細書き用)を用い、コーティング層に印字した。印字部にセロハンテープを圧着し、1500gの加重で擦った後、剥離した。セロハンテープの剥離前に対する剥離後の印字部の濃度により、以下の3段階で評価した。
〇:80%以上
△:50%以上80%未満
×:50%未満
(Ink acceptability)
Magic Ink No. manufactured by Teranishi Chemical Industry Co., Ltd. Printing was performed on the coating layer using 500 (for fine writing). A cellophane tape was pressure-bonded to the printed portion, rubbed with a load of 1500 g, and then peeled off. The cellophane tape was evaluated in the following three stages according to the density of the printed portion after peeling before peeling.
〇: 80% or more Δ: 50% or more and less than 80% ×: less than 50%
(耐溶剤性)
コーティング層に各種溶剤を数滴滴下し、室温で2時間静置した後表面を拭き取った。拭取り後のコーティング層の状態を目視にて4段階で評価した。
◎:変化なし
〇:積層体に対し60°から観察した場合には液滴縁が視認されないが、観察角度を変えると液滴縁が視認された
△:液滴縁が視認された
×:コーティング層が溶解していた
(Solvent resistance)
A few drops of various solvents were added dropwise to the coating layer, and the mixture was allowed to stand at room temperature for 2 hours and then the surface was wiped off. The state of the coating layer after wiping was visually evaluated on a 4-point scale.
⊚: No change 〇: Droplet edge was not visible when observed from 60 ° to the laminate, but droplet edge was visible when the observation angle was changed Δ: Droplet edge was visible ×: Coating The layer was dissolved
(水蒸気透過率)
Illinois社製水蒸気透過率測定装置7002を用い、伝導度法「ISO−15106−3」に準じ、40℃90%RHの雰囲気下で測定した。単位はcc/m2/day/atmである。
(Water vapor permeability)
The measurement was carried out in an atmosphere of 40 ° C. and 90% RH according to the conductivity method "ISO-15106-3" using a water vapor transmittance measuring device 7002 manufactured by Illinois. The unit is cc / m 2 / day / atm.
表3、4から明らかなように、本発明のコーティング剤は基材密着性、インキ受容性、各種溶剤への耐性、水蒸気バリア性等に優れる。一方比較例のコーティング剤は水蒸気透過率が劣る結果となり、また比較例2はブロッキングしコーティング剤としては適さないものであった。 As is clear from Tables 3 and 4, the coating agent of the present invention is excellent in substrate adhesion, ink acceptability, resistance to various solvents, water vapor barrier property, and the like. On the other hand, the coating agent of Comparative Example had a poor water vapor permeability, and Comparative Example 2 blocked and was not suitable as a coating agent.
Claims (14)
前記第1剤は酸基含有オレフィン樹脂(A1)を含む樹脂(A)を含み、
前記第2剤は前記酸基含有オレフィン樹脂(A1)が有する酸基と反応性を有する化合物(B)を含み、
前記酸基含有オレフィン樹脂(A1)は、前記酸基含有オレフィン樹脂(A1)と25℃で液体であるエポキシ化合物とがエポキシ過剰率が0.1以上1.5以下となるよう配合された組成物の硬化物を、JIS−K−7121に記載の結晶化温度の測定方法に従って測定した示差走査熱量測定において描かれるDSC曲線に結晶化ピークが観測されることを特徴とするコーティング剤。 Including the first agent and the second agent,
The first agent contains a resin (A) containing an acid group-containing olefin resin (A1).
The second agent contains a compound (B) that is reactive with the acid group of the acid group-containing olefin resin (A1).
The acid group-containing olefin resin (A1) has a composition in which the acid group-containing olefin resin (A1) and an epoxy compound that is liquid at 25 ° C. are blended so that the epoxy excess ratio is 0.1 or more and 1.5 or less. A coating agent characterized in that a crystallization peak is observed on a DSC curve drawn in differential scanning calorimetry in which a cured product of a product is measured according to the method for measuring a crystallization temperature described in JIS-K-7121.
前記第1剤に含まれる酸基と前記第2剤に含まれるイソシアネート基とのモル比(イソシアネート基/酸基)が0.5以上30以下である請求項1〜6のいずれか一項に記載のコーティング剤。 The compound (B) is an isocyanate compound (B1).
The item according to any one of claims 1 to 6, wherein the molar ratio (isocyanate group / acid group) of the acid group contained in the first agent to the isocyanate group contained in the second agent is 0.5 or more and 30 or less. The coating agent described.
前記樹脂(A)100質量部に対する前記硬化促進剤の配合量が0.01質量部以上5質量部以下である請求項8に記載のコーティング剤。 It contains at least one curing accelerator selected from the group consisting of metal-based catalysts, amine-based catalysts, aliphatic cyclic amide compounds, titanium chelate complexes, and organic phosphorus-based compounds.
The coating agent according to claim 8, wherein the amount of the curing accelerator blended with respect to 100 parts by mass of the resin (A) is 0.01 part by mass or more and 5 parts by mass or less.
前記第1剤に含まれる酸基と前記第2剤に含まれるエポキシ基とのモル比(エポキシ基/酸基)が0.01以上1.5以下である請求項1〜6のいずれか一項に記載のコーティング剤。 The compound (B) is an epoxy compound (B2).
Any one of claims 1 to 6 in which the molar ratio (epoxy group / acid group) of the acid group contained in the first agent to the epoxy group contained in the second agent is 0.01 or more and 1.5 or less. The coating agent described in the section.
前記樹脂(A)100質量部に対する前記硬化促進剤の配合量が0.01質量部以上5質量部以下である請求項10に記載のコーティング剤。 It contains at least one curing accelerator selected from the group consisting of organic phosphine compounds, imidazole compounds, tertiary amines and salts thereof.
The coating agent according to claim 10, wherein the blending amount of the curing accelerator with respect to 100 parts by mass of the resin (A) is 0.01 part by mass or more and 5 parts by mass or less.
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