JP2017520387A - 化学装置における表面のための被覆方法 - Google Patents
化学装置における表面のための被覆方法 Download PDFInfo
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- JP2017520387A JP2017520387A JP2016564026A JP2016564026A JP2017520387A JP 2017520387 A JP2017520387 A JP 2017520387A JP 2016564026 A JP2016564026 A JP 2016564026A JP 2016564026 A JP2016564026 A JP 2016564026A JP 2017520387 A JP2017520387 A JP 2017520387A
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- 239000000126 substance Substances 0.000 title claims abstract description 95
- 238000000576 coating method Methods 0.000 title claims abstract description 74
- 239000000203 mixture Substances 0.000 claims abstract description 100
- 239000008199 coating composition Substances 0.000 claims abstract description 91
- 239000003822 epoxy resin Substances 0.000 claims abstract description 79
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 79
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 77
- 239000011248 coating agent Substances 0.000 claims abstract description 68
- 150000001412 amines Chemical class 0.000 claims abstract description 57
- 238000000034 method Methods 0.000 claims abstract description 32
- 125000004400 (C1-C12) alkyl group Chemical group 0.000 claims abstract description 22
- 229910052751 metal Inorganic materials 0.000 claims abstract description 21
- 239000002184 metal Substances 0.000 claims abstract description 21
- 239000011247 coating layer Substances 0.000 claims abstract description 20
- 125000003700 epoxy group Chemical group 0.000 claims description 54
- UUODQIKUTGWMPT-UHFFFAOYSA-N 2-fluoro-5-(trifluoromethyl)pyridine Chemical compound FC1=CC=C(C(F)(F)F)C=N1 UUODQIKUTGWMPT-UHFFFAOYSA-N 0.000 claims description 46
- 150000001875 compounds Chemical class 0.000 claims description 36
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 30
- 125000003118 aryl group Chemical group 0.000 claims description 30
- 229910052739 hydrogen Inorganic materials 0.000 claims description 30
- 239000001257 hydrogen Substances 0.000 claims description 30
- 125000004209 (C1-C8) alkyl group Chemical group 0.000 claims description 22
- 125000000217 alkyl group Chemical group 0.000 claims description 18
- 238000003860 storage Methods 0.000 claims description 11
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- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 34
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- BPSIOYPQMFLKFR-UHFFFAOYSA-N trimethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CO[Si](OC)(OC)CCCOCC1CO1 BPSIOYPQMFLKFR-UHFFFAOYSA-N 0.000 description 17
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- 125000000524 functional group Chemical group 0.000 description 8
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 8
- 239000003973 paint Substances 0.000 description 8
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- TZZGHGKTHXIOMN-UHFFFAOYSA-N 3-trimethoxysilyl-n-(3-trimethoxysilylpropyl)propan-1-amine Chemical compound CO[Si](OC)(OC)CCCNCCC[Si](OC)(OC)OC TZZGHGKTHXIOMN-UHFFFAOYSA-N 0.000 description 5
- 238000010539 anionic addition polymerization reaction Methods 0.000 description 5
- 239000002585 base Substances 0.000 description 5
- 229920000768 polyamine Polymers 0.000 description 5
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 5
- 150000003839 salts Chemical class 0.000 description 5
- 238000005507 spraying Methods 0.000 description 5
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- GQHTUMJGOHRCHB-UHFFFAOYSA-N 2,3,4,6,7,8,9,10-octahydropyrimido[1,2-a]azepine Chemical compound C1CCCCN2CCCN=C21 GQHTUMJGOHRCHB-UHFFFAOYSA-N 0.000 description 4
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- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 4
- 239000012038 nucleophile Substances 0.000 description 4
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 4
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 4
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- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 3
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- 229930185605 Bisphenol Natural products 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 3
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 3
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 3
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- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 3
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- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 3
- 239000002253 acid Substances 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
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- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 3
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- 238000010438 heat treatment Methods 0.000 description 3
- 230000007062 hydrolysis Effects 0.000 description 3
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- RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
- 238000010348 incorporation Methods 0.000 description 3
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- 125000000421 1,2-aminoalcohol group Chemical group 0.000 description 2
- NFDXQGNDWIPXQL-UHFFFAOYSA-N 1-cyclooctyldiazocane Chemical compound C1CCCCCCC1N1NCCCCCC1 NFDXQGNDWIPXQL-UHFFFAOYSA-N 0.000 description 2
- YTWBFUCJVWKCCK-UHFFFAOYSA-N 2-heptadecyl-1h-imidazole Chemical compound CCCCCCCCCCCCCCCCCC1=NC=CN1 YTWBFUCJVWKCCK-UHFFFAOYSA-N 0.000 description 2
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- QOHMWDJIBGVPIF-UHFFFAOYSA-N n',n'-diethylpropane-1,3-diamine Chemical compound CCN(CC)CCCN QOHMWDJIBGVPIF-UHFFFAOYSA-N 0.000 description 1
- INJVFBCDVXYHGQ-UHFFFAOYSA-N n'-(3-triethoxysilylpropyl)ethane-1,2-diamine Chemical compound CCO[Si](OCC)(OCC)CCCNCCN INJVFBCDVXYHGQ-UHFFFAOYSA-N 0.000 description 1
- PHQOGHDTIVQXHL-UHFFFAOYSA-N n'-(3-trimethoxysilylpropyl)ethane-1,2-diamine Chemical compound CO[Si](OC)(OC)CCCNCCN PHQOGHDTIVQXHL-UHFFFAOYSA-N 0.000 description 1
- DUWWHGPELOTTOE-UHFFFAOYSA-N n-(5-chloro-2,4-dimethoxyphenyl)-3-oxobutanamide Chemical compound COC1=CC(OC)=C(NC(=O)CC(C)=O)C=C1Cl DUWWHGPELOTTOE-UHFFFAOYSA-N 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- NXPPAOGUKPJVDI-UHFFFAOYSA-N naphthalene-1,2-diol Chemical class C1=CC=CC2=C(O)C(O)=CC=C21 NXPPAOGUKPJVDI-UHFFFAOYSA-N 0.000 description 1
- YZMHQCWXYHARLS-UHFFFAOYSA-N naphthalene-1,2-disulfonic acid Chemical compound C1=CC=CC2=C(S(O)(=O)=O)C(S(=O)(=O)O)=CC=C21 YZMHQCWXYHARLS-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- 150000001282 organosilanes Chemical class 0.000 description 1
- 125000005375 organosiloxane group Chemical group 0.000 description 1
- 235000006408 oxalic acid Nutrition 0.000 description 1
- FJKROLUGYXJWQN-UHFFFAOYSA-N papa-hydroxy-benzoic acid Natural products OC(=O)C1=CC=C(O)C=C1 FJKROLUGYXJWQN-UHFFFAOYSA-N 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- WVDDGKGOMKODPV-ZQBYOMGUSA-N phenyl(114C)methanol Chemical compound O[14CH2]C1=CC=CC=C1 WVDDGKGOMKODPV-ZQBYOMGUSA-N 0.000 description 1
- 239000003279 phenylacetic acid Substances 0.000 description 1
- 229960003424 phenylacetic acid Drugs 0.000 description 1
- QCDYQQDYXPDABM-UHFFFAOYSA-N phloroglucinol Chemical compound OC1=CC(O)=CC(O)=C1 QCDYQQDYXPDABM-UHFFFAOYSA-N 0.000 description 1
- 229960001553 phloroglucinol Drugs 0.000 description 1
- 125000004437 phosphorous atom Chemical group 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- IEQIEDJGQAUEQZ-UHFFFAOYSA-N phthalocyanine Chemical compound N1C(N=C2C3=CC=CC=C3C(N=C3C4=CC=CC=C4C(=N4)N3)=N2)=C(C=CC=C2)C2=C1N=C1C2=CC=CC=C2C4=N1 IEQIEDJGQAUEQZ-UHFFFAOYSA-N 0.000 description 1
- OXNIZHLAWKMVMX-UHFFFAOYSA-N picric acid Chemical compound OC1=C([N+]([O-])=O)C=C([N+]([O-])=O)C=C1[N+]([O-])=O OXNIZHLAWKMVMX-UHFFFAOYSA-N 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002857 polybutadiene Polymers 0.000 description 1
- 239000004848 polyfunctional curative Substances 0.000 description 1
- 229920001296 polysiloxane Polymers 0.000 description 1
- 239000011591 potassium Substances 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- ZNNZYHKDIALBAK-UHFFFAOYSA-M potassium thiocyanate Chemical compound [K+].[S-]C#N ZNNZYHKDIALBAK-UHFFFAOYSA-M 0.000 description 1
- 229940116357 potassium thiocyanate Drugs 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- ULWHHBHJGPPBCO-UHFFFAOYSA-N propane-1,1-diol Chemical compound CCC(O)O ULWHHBHJGPPBCO-UHFFFAOYSA-N 0.000 description 1
- 235000019260 propionic acid Nutrition 0.000 description 1
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical group CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 1
- 239000002994 raw material Substances 0.000 description 1
- 230000003014 reinforcing effect Effects 0.000 description 1
- 238000007142 ring opening reaction Methods 0.000 description 1
- 229960004889 salicylic acid Drugs 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- 235000012239 silicon dioxide Nutrition 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- VGTPCRGMBIAPIM-UHFFFAOYSA-M sodium thiocyanate Chemical compound [Na+].[S-]C#N VGTPCRGMBIAPIM-UHFFFAOYSA-M 0.000 description 1
- 239000000600 sorbitol Substances 0.000 description 1
- 241000894007 species Species 0.000 description 1
- 239000007921 spray Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 125000004434 sulfur atom Chemical group 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- FAGUFWYHJQFNRV-UHFFFAOYSA-N tetraethylenepentamine Chemical compound NCCNCCNCCNCCN FAGUFWYHJQFNRV-UHFFFAOYSA-N 0.000 description 1
- 239000002562 thickening agent Substances 0.000 description 1
- 239000004408 titanium dioxide Substances 0.000 description 1
- BJIOGJUNALELMI-UHFFFAOYSA-N trans-isoeugenol Natural products COC1=CC(C=CC)=CC=C1O BJIOGJUNALELMI-UHFFFAOYSA-N 0.000 description 1
- LGQXXHMEBUOXRP-UHFFFAOYSA-N tributyl borate Chemical compound CCCCOB(OCCCC)OCCCC LGQXXHMEBUOXRP-UHFFFAOYSA-N 0.000 description 1
- CPUDPFPXCZDNGI-UHFFFAOYSA-N triethoxy(methyl)silane Chemical compound CCO[Si](C)(OCC)OCC CPUDPFPXCZDNGI-UHFFFAOYSA-N 0.000 description 1
- JCVQKRGIASEUKR-UHFFFAOYSA-N triethoxy(phenyl)silane Chemical compound CCO[Si](OCC)(OCC)C1=CC=CC=C1 JCVQKRGIASEUKR-UHFFFAOYSA-N 0.000 description 1
- JXUKBNICSRJFAP-UHFFFAOYSA-N triethoxy-[3-(oxiran-2-ylmethoxy)propyl]silane Chemical compound CCO[Si](OCC)(OCC)CCCOCC1CO1 JXUKBNICSRJFAP-UHFFFAOYSA-N 0.000 description 1
- AHZJKOKFZJYCLG-UHFFFAOYSA-K trifluoromethanesulfonate;ytterbium(3+) Chemical compound [Yb+3].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F AHZJKOKFZJYCLG-UHFFFAOYSA-K 0.000 description 1
- ZNOCGWVLWPVKAO-UHFFFAOYSA-N trimethoxy(phenyl)silane Chemical compound CO[Si](OC)(OC)C1=CC=CC=C1 ZNOCGWVLWPVKAO-UHFFFAOYSA-N 0.000 description 1
- YUYCVXFAYWRXLS-UHFFFAOYSA-N trimethoxysilane Chemical compound CO[SiH](OC)OC YUYCVXFAYWRXLS-UHFFFAOYSA-N 0.000 description 1
- WRECIMRULFAWHA-UHFFFAOYSA-N trimethyl borate Chemical compound COB(OC)OC WRECIMRULFAWHA-UHFFFAOYSA-N 0.000 description 1
- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
- 239000002699 waste material Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000010456 wollastonite Substances 0.000 description 1
- 229910052882 wollastonite Inorganic materials 0.000 description 1
- CITILBVTAYEWKR-UHFFFAOYSA-L zinc trifluoromethanesulfonate Chemical compound [Zn+2].[O-]S(=O)(=O)C(F)(F)F.[O-]S(=O)(=O)C(F)(F)F CITILBVTAYEWKR-UHFFFAOYSA-L 0.000 description 1
- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 0.000 description 1
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- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/08—Anti-corrosive paints
- C09D5/082—Anti-corrosive paints characterised by the anti-corrosive pigment
- C09D5/086—Organic or non-macromolecular compounds
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- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/007—After-treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
- B05D3/02—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by baking
- B05D3/0254—After-treatment
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
- B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
- B05D7/14—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials to metal, e.g. car bodies
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- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
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- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
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- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/46—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with organic materials
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- C04B41/00—After-treatment of mortars, concrete, artificial stone or ceramics; Treatment of natural stone
- C04B41/45—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements
- C04B41/50—Coating or impregnating, e.g. injection in masonry, partial coating of green or fired ceramics, organic coating compositions for adhering together two concrete elements with inorganic materials
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- Paints Or Removers (AREA)
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Abstract
Description
−第1のパックはエポキシ樹脂を含み、第2のパックは、エポキシ樹脂のためのアミン硬化剤を含み、被覆組成物は、式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である。)の有機ホウ素化合物をさらに含む、2つのパックの被覆組成物を提供する工程と、
−第1のパックと第2のパックを合わせて被覆組成物を生成する工程と、
−被覆組成物を化学装置の表面に塗布して被覆層を形成する工程と、
−被覆層を0〜50℃の範囲の温度で硬化させる工程とを含む。
−(1つ又はそれ以上の)硬化剤中の活性水素と組成物中に存在するエポキシ基の当量比が1.00:1.00又はそれより大きいとき、組成物中に存在するB−OY2基の数は好ましくは、組成物中に存在するエポキシ基の数の5〜80%、より好ましくは10〜50%、最も好ましくは20〜40%と等しく、
−(1つ又はそれ以上の)硬化剤中の活性水素と組成物中に存在するエポキシ基の当量比が1.00:1.00未満であるとき、組成物中に存在するB−OY2基の数は好ましくは、(1つ又はそれ以上の)硬化剤中の活性水素の数の5〜80%、好ましくは10〜50%、最も好ましくは20〜40%と等しい。
−(1つ又はそれ以上の)硬化剤中の活性水素と組成物中に存在するエポキシ基の当量比が1.00:1.00又はそれより大きいとき、組成物中に存在するB−OY2基の数は好ましくは、組成物中に存在するエポキシ基の数の15〜50%、より好ましくは15〜40%と等しく、
−(1つ又はそれ以上の)硬化剤中の活性水素と組成物中に存在するエポキシ基の当量比が1.00:1.00未満であるとき、組成物中に存在するB−OY2基の数は好ましくは、(1つ又はそれ以上の)硬化剤中の活性水素の数の15〜50%、好ましくは15〜40%と等しい。
式2:Q’−NH−R’1−Si−(OR’2)n’(R’3)2−n’−O[−(Q−NH−R’1)Si(OR’2)n’−1(R’3)2−n’−O−]m’R’2
(式中、Q’は残基−(CH2CH2NH)z’−H又はアミノアリール基を表し、R’1は1〜6個の炭素原子を持つ脂肪族アルキル基を表し、R’2は一価の脂肪族C1−C6アルキル基を表し、R’3は一価の脂肪族C1−C6アルキル基又は一価のC6芳香族基を表し、n’は1又は2であり、m’はゼロより大きいかゼロと等しい整数である。)のものが含まれる。式2において、z’は値0、1又は2を有する。
式1:Q−R1−Si−(OR2)n(R3)2−n−O[−(Q−R1)Si(OR2)n−1(R3)2−n−O−]mR2
(式中、Qはグリシドキシ基
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)2SiO1/2)e及び(C6H5SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)2SiO1/2)e、((CH3)2SiO2/2)f及び(C6H5SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
((CH3)3SiO1/2)e、(R4(CH3)SiO2/2)f及び(C6H5SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)SiO2/2)f及び(C6H5SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)2SiO1/2)e及び(CH3SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)2SiO1/2)e、((CH3)2SiO2/2)f及び(CH3SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
((CH3)3SiO1/2)e、(R4(CH3)SiO2/2)f及び(CH3SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
(R4(CH3)SiO2/2)f及び(CH3SiO3/2)g
次の単位を含むエポキシ官能性ケイ素物質:
((CH3)2SiO2/2)f及び(R4SiO3/2)g。
エポキシ樹脂とアミン硬化剤との硬化反応を速める公知の促進剤の例には以下が含まれる:アルコール、フェノール、カルボン酸、スルホン酸、塩及び三級アミン:
アルコール:適したアルコールの例には、エタノール、1−プロパノール、2−プロパノール、1−ブタノール、2−ブタノール、t−ブタノール、ベンジルアルコール、フルフリルアルコール及び他のアルキルアルコール、プロパンジオール、ブタンジオール、グリセロール及び他の多価アルコール、トリエタノールアミン、トリイソプロパノールアミン、ジメチルアミノエタノール及び他のβ−ヒドロキシ三級アミンが含まれる。
塩:適した塩の例には、硝酸カルシウム、ナフテン酸カルシウム、チオシアン酸アンモニウム、チオシアン酸ナトリウム、チオシアン酸カリウム、チオシアン酸イミダゾリニウム、リチウムテトラフルオロボラート、臭化リチウム、トリフルオロ酢酸リチウム、塩化カルシウム、イッテルビウムトリフラート、過塩素酸リチウム、亜鉛トリフラート、硝酸リチウムが含まれる。これらの塩すべてについて、陽イオンは、リチウム、ナトリウム又はカリウムと交換され得る。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、酢酸ビニル及びエチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂と、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示す。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、酢酸ビニル及びエチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂の混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の80%はエポキシノボラック樹脂に由来し、エポキシ基の20%はエポキシ官能性シラン樹脂に由来し、アミン硬化剤及びトリアルキルボラートエステルで硬化される。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、酢酸ビニル及びエチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂と、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シロキサン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の70%はノボラック樹脂に由来し、エポキシ基の30%はエポキシ官能性シラン樹脂に由来する。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、酢酸ビニル及びエチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂と、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の80%はノボラック樹脂に由来し、エポキシ基の20%はエポキシ官能性シラン樹脂に由来し、ここで、合わせたエポキシ樹脂は着色塗料配合物の一部である。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、エチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂の混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の80%はエポキシノボラック樹脂に由来し、エポキシ基の20%はエポキシ官能性シラン樹脂に由来し、ビス(4−アミノシクロヘキシル)メタンとDynasylan 1124の混合物及びトリアルキルボラートエステルを含むアミン硬化剤で硬化される。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、エチレンジクロリドの取り込み質量%に対するエポキシノボラック樹脂の混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の80%はエポキシノボラック樹脂に由来し、エポキシ基の20%はエポキシ官能性シラン樹脂に由来し、ビス(4−アミノシクロヘキシル)メタンとアミノプロピルトリメトキシシランの混合物及びDynasylan 1124並びにトリアルキルボラートエステルを含むアミン硬化剤で硬化される。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、酢酸ビニル及びエチレンジクロリドの取り込み質量%に対するビスフェノールFエポキシ樹脂と、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の80%はビスフェノールFエポキシ樹脂に由来し、エポキシ基の20%はエポキシ官能性シラン樹脂に由来し、ここで、合わせたエポキシ樹脂は着色塗料配合物の一部である。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、エチレンジクロリドの取り込み質量%に対するビスフェノールFエポキシ樹脂と、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示し、ここで、樹脂の粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の70%はビスフェノールFエポキシ樹脂に由来し、エポキシ基の30%はエポキシ官能性シラン樹脂に由来し、ここで、合わせたエポキシ樹脂は着色塗料配合物の一部である。
本発明によるこの実施例は、レソルシノールジグリシジルエーテルを全く加えないときの、エチレンジクロリドの取り込み質量%に対するフェノールノボラックエポキシ樹脂及びビスフェノールFエポキシ樹脂のブレンドと、アミン硬化剤及びトリアルキルボラートエステルとの混合の影響を示し、ここで、エポキシ樹脂ブレンドの粘度が、エポキシ官能性シラン樹脂とのその組み合わせにより変更されており、したがって、エポキシ基の70%はエポキシノボラック樹脂及びビスフェノールFエポキシ樹脂の混合物に由来し、エポキシ基の30%はエポキシ官能性シラン樹脂に由来し、ここで、合わせたエポキシ樹脂は着色塗料配合物の一部である。
この比較例では、唯一のエポキシ樹脂としてエポキシフェノールノボラック(DEN 431)を用いて調製した被覆内の各種有機液体の比較的高い吸収が示される。
この比較例では、唯一のエポキシ樹脂としてレソルシノールジグリシジルエーテル(RDGE)を用いて調製した被覆内の各種有機液体の低い吸収が示される。
この比較例では、レソルシノールジグリシジルエーテル(RDGE)とエポキシフェノールノボラック(DEN 431)のブレンドを用いて調製した被覆内の各種有機液体の低い吸収が示される。
本願発明には以下の態様が含まれる。
項1.
−第1パックがエポキシ樹脂を含み、第2パックが前記エポキシ樹脂のためのアミン硬化剤を含む、2つのパックの被覆組成物であって、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む2つのパックの被覆組成物を提供する工程と、
−前記第1パックと前記第2パックを合わせて被覆組成物を生成する工程と、
−前記被覆組成物を化学装置の表面に塗布して被覆層を形成する工程と、
−前記被覆層を0〜50℃の範囲の温度で硬化させる工程とを含む、化学装置の金属又はコンクリート表面に被覆を設けるための方法。
項2.
前記被覆層に50℃を超える温度の後硬化工程がさらに施される、項1に記載の方法。
項3.
前記化学装置が、煙突、パイプ又はタンク、例えば、貨物タンク又は貯蔵タンクである、項1又は2に記載の方法。
項4.
前記有機ホウ素化合物が、
−前記硬化剤中の活性水素と前記組成物中に存在するエポキシ基の当量比が1.00:1.00又はそれより大きいとき、前記組成物中に存在するB−OY2基の数が、前記組成物中に存在するエポキシ基の数の5〜80%、より好ましくは10〜50%、最も好ましくは20〜40%と等しく、及び
−前記硬化剤中の活性水素と前記組成物中に存在するエポキシ基の当量比が1.00:1.00未満であるとき、前記組成物中に存在するB−OY2基の数が、前記硬化剤中の活性水素の数の5〜80%、好ましくは10〜50%、最も好ましくは20〜40%と等しい、
ような量で存在する、項1から3のいずれか一項に記載の方法。
項5.
Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、項1から4のいずれか一項に記載の方法。
項6.
Y1及び/又はY2が、C2−C5アルキル基から独立に選択される、項5に記載の方法。
項7.
X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、項1から4のいずれかに記載の方法。
項8.
前記被覆組成物が、10重量%未満のRDGE(レソルシノールジグリシジルエーテル)、特に5重量%未満のRDGE、例えば2重量%未満のRDGEを含む、項1から7のいずれか一項に記載の方法。
項9.
硬化した被覆組成物のライニングを設けた金属又はコンクリート表面を含む化学装置であって、
前記被覆組成物が、エポキシ樹脂及び前記エポキシ樹脂のためのアミン硬化剤を含む被覆組成物から誘導され、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む、
化学装置。
項10.
煙突、パイプ又はタンク、例えば、貨物タンク又は貯蔵タンクである、項9に記載の化学装置。
項11.
Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、項9又は10に記載の化学装置。
項12.
X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、項9から11のいずれか一項に記載の化学装置。
項13.
第1パックがエポキシ樹脂を含み、第2のパックが前記エポキシ樹脂のためのアミン硬化剤を含む、2つのパックの被覆組成物であり、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む、化学装置の金属又はコンクリート表面に被覆を設けるのに適した被覆組成物。
項14.
Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、項13に記載の被覆組成物。
項15.
X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、項14に記載の被覆組成物。
Claims (15)
- −第1パックがエポキシ樹脂を含み、第2パックが前記エポキシ樹脂のためのアミン硬化剤を含む、2つのパックの被覆組成物であって、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む2つのパックの被覆組成物を提供する工程と、
−前記第1パックと前記第2パックを合わせて被覆組成物を生成する工程と、
−前記被覆組成物を化学装置の表面に塗布して被覆層を形成する工程と、
−前記被覆層を0〜50℃の範囲の温度で硬化させる工程とを含む、化学装置の金属又はコンクリート表面に被覆を設けるための方法。 - 前記被覆層に50℃を超える温度の後硬化工程がさらに施される、請求項1に記載の方法。
- 前記化学装置が、煙突、パイプ又はタンク、例えば、貨物タンク又は貯蔵タンクである、請求項1又は2に記載の方法。
- 前記有機ホウ素化合物が、
−前記硬化剤中の活性水素と前記組成物中に存在するエポキシ基の当量比が1.00:1.00又はそれより大きいとき、前記組成物中に存在するB−OY2基の数が、前記組成物中に存在するエポキシ基の数の5〜80%、より好ましくは10〜50%、最も好ましくは20〜40%と等しく、及び
−前記硬化剤中の活性水素と前記組成物中に存在するエポキシ基の当量比が1.00:1.00未満であるとき、前記組成物中に存在するB−OY2基の数が、前記硬化剤中の活性水素の数の5〜80%、好ましくは10〜50%、最も好ましくは20〜40%と等しい、
ような量で存在する、請求項1から3のいずれか一項に記載の方法。 - Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、請求項1から4のいずれか一項に記載の方法。
- Y1及び/又はY2が、C2−C5アルキル基から独立に選択される、請求項5に記載の方法。
- X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、請求項1から4のいずれかに記載の方法。
- 前記被覆組成物が、10重量%未満のRDGE(レソルシノールジグリシジルエーテル)、特に5重量%未満のRDGE、例えば2重量%未満のRDGEを含む、請求項1から7のいずれか一項に記載の方法。
- 硬化した被覆組成物のライニングを設けた金属又はコンクリート表面を含む化学装置であって、
前記被覆組成物が、エポキシ樹脂及び前記エポキシ樹脂のためのアミン硬化剤を含む被覆組成物から誘導され、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む、
化学装置。 - 煙突、パイプ又はタンク、例えば、貨物タンク又は貯蔵タンクである、請求項9に記載の化学装置。
- Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、請求項9又は10に記載の化学装置。
- X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、請求項9から11のいずれか一項に記載の化学装置。
- 第1パックがエポキシ樹脂を含み、第2のパックが前記エポキシ樹脂のためのアミン硬化剤を含む、2つのパックの被覆組成物であり、さらに式BX1X2X3(式中、X1、X2及びX3は、−Y1及び−OY2から独立に選択され、Y1は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、Y2は、一価のC1−C12アルキル基及び一価のC6−C12アリール基から独立に選択され、X1、X2及びX3のうちの少なくとも1つは−OY2基である)の有機ホウ素化合物を含む、化学装置の金属又はコンクリート表面に被覆を設けるのに適した被覆組成物。
- Y1及び/又はY2が、C1−C8アルキル基及びC6−C8アリール基から独立に選択され、特に、Y1及びY2がいずれも、C1−C8アルキル基及びC6−C8アリール基から独立に選択される、請求項13に記載の被覆組成物。
- X1、X2及びX3のすべてが、独立に選択される−OY2基であり、特に前記Y2基が、C1−C8アルキル基及びC6−C8アリール基、とりわけC2−C5アルキル基から独立に選択される、請求項14に記載の被覆組成物。
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EP (1) | EP3137560B1 (ja) |
JP (1) | JP6526713B2 (ja) |
KR (1) | KR102453676B1 (ja) |
CN (1) | CN106232739B (ja) |
AU (1) | AU2015252252A1 (ja) |
BR (1) | BR112016024139A2 (ja) |
CA (1) | CA2960389A1 (ja) |
DK (1) | DK3137560T3 (ja) |
ES (1) | ES2804124T3 (ja) |
RU (1) | RU2016144036A (ja) |
SG (1) | SG11201608930VA (ja) |
TW (1) | TW201546202A (ja) |
WO (1) | WO2015165808A1 (ja) |
Families Citing this family (11)
Publication number | Priority date | Publication date | Assignee | Title |
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EP3490726B1 (en) * | 2016-07-26 | 2022-11-30 | PPG Industries Ohio, Inc. | Multi-layer curable compositions containing 1,1-di-activated vinyl compound products and related processes |
WO2018022792A1 (en) | 2016-07-26 | 2018-02-01 | Ppg Industries Ohio, Inc. | Electrodepositable coating compositions containing 1,1-di-activated vinyl compounds |
US11466159B2 (en) | 2016-07-26 | 2022-10-11 | Ppg Industries Ohio, Inc. | Particles having surfaces functionalized with 1,1-di-activated vinyl compounds |
ES2928648T3 (es) | 2016-07-26 | 2022-11-21 | Ppg Ind Ohio Inc | Procesos de impresión tridimensional mediante el uso de compuestos vinílicos 1,1-di-activados |
US11136469B2 (en) | 2016-07-26 | 2021-10-05 | Ppg Industries Ohio, Inc. | Acid-catalyzed curable coating compositions containing 1,1-di-activated vinyl compounds and related coatings and processes |
ES2932518T3 (es) | 2016-07-26 | 2023-01-20 | Ppg Ind Ohio Inc | Composiciones curables que contienen compuestos vinílicos 1,1-diactivados y recubrimientos y procesos relacionados |
CN109642099B (zh) | 2016-07-26 | 2021-11-30 | Ppg工业俄亥俄公司 | 含有1,1-二活化的乙烯基化合物的聚氨酯涂料组合物和相关的涂料和方法 |
US10934411B2 (en) | 2016-09-30 | 2021-03-02 | Ppg Industries Ohio, Inc. | Curable compositions containing 1,1-di-activated vinyl compounds that cure by pericyclic reaction mechanisms |
WO2019133947A1 (en) * | 2017-12-30 | 2019-07-04 | Saint-Gobain Performance Plastics Corporation | Heterochain polymer composition |
WO2024079077A1 (en) | 2022-10-11 | 2024-04-18 | Akzo Nobel Coatings International B.V. | Low temperature curing coating composition |
CN116218150B (zh) * | 2023-03-31 | 2024-06-14 | 武汉联影医疗科技有限公司 | 一种匹配材料及其应用和制备方法 |
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US3446756A (en) * | 1965-12-06 | 1969-05-27 | Thomas Ramos | Method of making resinous epoxy prepolymers and curing of same |
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EP0458502B1 (en) * | 1990-05-21 | 2003-06-18 | Dow Global Technologies Inc. | Latent catalysts, cure-inhibited epoxy resin compositions and laminates prepared therefrom |
US6641923B2 (en) * | 2001-07-31 | 2003-11-04 | Ppg Industries Ohio, Inc. | Weldable coating compositions having improved intercoat adhesion |
TWI586749B (zh) * | 2010-11-19 | 2017-06-11 | 漢高日本股份有限公司 | 單組分環氧樹脂組成物 |
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CN102174173B (zh) * | 2011-01-21 | 2012-09-05 | 华南理工大学 | 阻燃潜伏性环氧固化剂及其无卤阻燃单组分环氧树脂组合物 |
KR101963720B1 (ko) * | 2011-03-07 | 2019-03-29 | 아크조노벨코팅스인터내셔널비.브이. | 카고 탱크 코팅 |
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- 2015-04-24 BR BR112016024139A patent/BR112016024139A2/pt not_active Application Discontinuation
- 2015-04-24 CN CN201580020931.0A patent/CN106232739B/zh active Active
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- 2015-04-24 AU AU2015252252A patent/AU2015252252A1/en not_active Abandoned
- 2015-04-24 SG SG11201608930VA patent/SG11201608930VA/en unknown
- 2015-04-24 US US15/306,022 patent/US10077377B2/en active Active
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- 2015-04-24 WO PCT/EP2015/058868 patent/WO2015165808A1/en active Application Filing
- 2015-04-24 ES ES15720036T patent/ES2804124T3/es active Active
- 2015-04-24 CA CA2960389A patent/CA2960389A1/en not_active Abandoned
- 2015-04-24 DK DK15720036.1T patent/DK3137560T3/da active
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Patent Citations (5)
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JPH03275773A (ja) * | 1990-03-26 | 1991-12-06 | Nippon Steel Corp | 重防食被覆鋼材 |
JP2002338787A (ja) * | 2001-05-15 | 2002-11-27 | Kawamura Inst Of Chem Res | エポキシ樹脂組成物及びその硬化物 |
WO2012151171A1 (en) * | 2011-05-02 | 2012-11-08 | Dow Global Technologies Llc | Trimethyl borate in epoxy resins |
JP2014523451A (ja) * | 2011-05-02 | 2014-09-11 | ダウ グローバル テクノロジーズ エルエルシー | エポキシ樹脂中のホウ酸トリメチル |
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Also Published As
Publication number | Publication date |
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US10077377B2 (en) | 2018-09-18 |
ES2804124T3 (es) | 2021-02-03 |
AU2015252252A1 (en) | 2016-10-20 |
US20170044396A1 (en) | 2017-02-16 |
CN106232739A (zh) | 2016-12-14 |
KR102453676B1 (ko) | 2022-10-11 |
WO2015165808A1 (en) | 2015-11-05 |
CA2960389A1 (en) | 2015-11-05 |
CN106232739B (zh) | 2019-08-02 |
JP6526713B2 (ja) | 2019-06-05 |
SG11201608930VA (en) | 2016-11-29 |
KR20170003545A (ko) | 2017-01-09 |
DK3137560T3 (da) | 2020-08-17 |
BR112016024139A2 (pt) | 2017-08-15 |
EP3137560B1 (en) | 2020-06-03 |
RU2016144036A (ru) | 2018-05-30 |
EP3137560A1 (en) | 2017-03-08 |
TW201546202A (zh) | 2015-12-16 |
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