CN101133133B - Epoxy coating composition - Google Patents
Epoxy coating composition Download PDFInfo
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- CN101133133B CN101133133B CN2005800488014A CN200580048801A CN101133133B CN 101133133 B CN101133133 B CN 101133133B CN 2005800488014 A CN2005800488014 A CN 2005800488014A CN 200580048801 A CN200580048801 A CN 200580048801A CN 101133133 B CN101133133 B CN 101133133B
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- China
- Prior art keywords
- coating composition
- epoxy
- epoxy coating
- hydrocarbon
- resin
- Prior art date
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- 239000008199 coating composition Substances 0.000 title claims abstract description 34
- 229920006334 epoxy coating Polymers 0.000 title claims abstract description 33
- 239000003795 chemical substances by application Substances 0.000 claims abstract description 30
- 239000003822 epoxy resin Substances 0.000 claims abstract description 30
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 30
- 238000000576 coating method Methods 0.000 claims abstract description 29
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims abstract description 29
- 239000011248 coating agent Substances 0.000 claims abstract description 27
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 claims abstract description 12
- 239000007787 solid Substances 0.000 claims abstract description 4
- 229930195733 hydrocarbon Natural products 0.000 claims description 44
- 150000002430 hydrocarbons Chemical class 0.000 claims description 44
- 239000004215 Carbon black (E152) Substances 0.000 claims description 36
- 239000000203 mixture Substances 0.000 claims description 25
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 12
- 239000002253 acid Substances 0.000 claims description 12
- 150000002989 phenols Chemical class 0.000 claims description 11
- 150000001875 compounds Chemical class 0.000 claims description 10
- 239000000470 constituent Substances 0.000 claims description 9
- 238000006116 polymerization reaction Methods 0.000 claims description 9
- 239000000178 monomer Substances 0.000 claims description 8
- 238000009835 boiling Methods 0.000 claims description 6
- 125000003118 aryl group Chemical group 0.000 claims description 5
- 238000005336 cracking Methods 0.000 claims description 5
- 229920000642 polymer Polymers 0.000 claims 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract description 17
- 238000005260 corrosion Methods 0.000 abstract description 15
- 239000013032 Hydrocarbon resin Substances 0.000 abstract description 14
- 229920006270 hydrocarbon resin Polymers 0.000 abstract description 14
- 239000003973 paint Substances 0.000 abstract description 11
- 238000002156 mixing Methods 0.000 abstract description 5
- 230000001070 adhesive effect Effects 0.000 abstract 1
- 229920005989 resin Polymers 0.000 description 18
- 239000011347 resin Substances 0.000 description 18
- 238000006243 chemical reaction Methods 0.000 description 17
- 238000000034 method Methods 0.000 description 16
- 230000007797 corrosion Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 238000002360 preparation method Methods 0.000 description 12
- 230000000052 comparative effect Effects 0.000 description 9
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- 239000003921 oil Substances 0.000 description 6
- 239000000049 pigment Substances 0.000 description 6
- -1 amide amine Chemical class 0.000 description 5
- 230000037452 priming Effects 0.000 description 5
- 239000004593 Epoxy Substances 0.000 description 4
- RRHGJUQNOFWUDK-UHFFFAOYSA-N Isoprene Chemical compound CC(=C)C=C RRHGJUQNOFWUDK-UHFFFAOYSA-N 0.000 description 4
- 229910001209 Low-carbon steel Inorganic materials 0.000 description 4
- ZSWFCLXCOIISFI-UHFFFAOYSA-N cyclopentadiene Chemical compound C1C=CC=C1 ZSWFCLXCOIISFI-UHFFFAOYSA-N 0.000 description 4
- 238000005238 degreasing Methods 0.000 description 4
- 238000005498 polishing Methods 0.000 description 4
- 229920006122 polyamide resin Polymers 0.000 description 4
- 239000000126 substance Substances 0.000 description 4
- 239000011269 tar Substances 0.000 description 4
- 229930195735 unsaturated hydrocarbon Natural products 0.000 description 4
- RSWGJHLUYNHPMX-UHFFFAOYSA-N 1,4a-dimethyl-7-propan-2-yl-2,3,4,4b,5,6,10,10a-octahydrophenanthrene-1-carboxylic acid Chemical compound C12CCC(C(C)C)=CC2=CCC2C1(C)CCCC2(C)C(O)=O RSWGJHLUYNHPMX-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000007259 addition reaction Methods 0.000 description 3
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000007613 environmental effect Effects 0.000 description 3
- 150000002469 indenes Chemical class 0.000 description 3
- 229920000768 polyamine Polymers 0.000 description 3
- PMJHHCWVYXUKFD-SNAWJCMRSA-N (E)-1,3-pentadiene Chemical compound C\C=C\C=C PMJHHCWVYXUKFD-SNAWJCMRSA-N 0.000 description 2
- LRTOHSLOFCWHRF-UHFFFAOYSA-N 1-methyl-1h-indene Chemical class C1=CC=C2C(C)C=CC2=C1 LRTOHSLOFCWHRF-UHFFFAOYSA-N 0.000 description 2
- VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
- GJYCVCVHRSWLNY-UHFFFAOYSA-N 2-butylphenol Chemical compound CCCCC1=CC=CC=C1O GJYCVCVHRSWLNY-UHFFFAOYSA-N 0.000 description 2
- NIXOWILDQLNWCW-UHFFFAOYSA-N Acrylic acid Chemical compound OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- VZCYOOQTPOCHFL-OWOJBTEDSA-N Fumaric acid Chemical compound OC(=O)\C=C\C(O)=O VZCYOOQTPOCHFL-OWOJBTEDSA-N 0.000 description 2
- NTIZESTWPVYFNL-UHFFFAOYSA-N Methyl isobutyl ketone Chemical compound CC(C)CC(C)=O NTIZESTWPVYFNL-UHFFFAOYSA-N 0.000 description 2
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 2
- 229910000831 Steel Inorganic materials 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000000654 additive Substances 0.000 description 2
- XYLMUPLGERFSHI-UHFFFAOYSA-N alpha-Methylstyrene Chemical compound CC(=C)C1=CC=CC=C1 XYLMUPLGERFSHI-UHFFFAOYSA-N 0.000 description 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 2
- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- LVHBHZANLOWSRM-UHFFFAOYSA-N itaconic acid Chemical compound OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 2
- 239000012046 mixed solvent Substances 0.000 description 2
- QWVGKYWNOKOFNN-UHFFFAOYSA-N o-cresol Chemical compound CC1=CC=CC=C1O QWVGKYWNOKOFNN-UHFFFAOYSA-N 0.000 description 2
- IWDCLRJOBJJRNH-UHFFFAOYSA-N p-cresol Chemical compound CC1=CC=C(O)C=C1 IWDCLRJOBJJRNH-UHFFFAOYSA-N 0.000 description 2
- 238000005120 petroleum cracking Methods 0.000 description 2
- PMJHHCWVYXUKFD-UHFFFAOYSA-N piperylene Natural products CC=CC=C PMJHHCWVYXUKFD-UHFFFAOYSA-N 0.000 description 2
- 230000000379 polymerizing effect Effects 0.000 description 2
- HJWLCRVIBGQPNF-UHFFFAOYSA-N prop-2-enylbenzene Chemical compound C=CCC1=CC=CC=C1 HJWLCRVIBGQPNF-UHFFFAOYSA-N 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000007665 sagging Methods 0.000 description 2
- 239000013535 sea water Substances 0.000 description 2
- 238000005507 spraying Methods 0.000 description 2
- 239000010959 steel Substances 0.000 description 2
- 239000002641 tar oil Substances 0.000 description 2
- 230000000007 visual effect Effects 0.000 description 2
- 238000009736 wetting Methods 0.000 description 2
- 239000008096 xylene Substances 0.000 description 2
- JKTAIYGNOFSMCE-UHFFFAOYSA-N 2,3-di(nonyl)phenol Chemical compound CCCCCCCCCC1=CC=CC(O)=C1CCCCCCCCC JKTAIYGNOFSMCE-UHFFFAOYSA-N 0.000 description 1
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 description 1
- RNLHGQLZWXBQNY-UHFFFAOYSA-N 3-(aminomethyl)-3,5,5-trimethylcyclohexan-1-amine Chemical compound CC1(C)CC(N)CC(C)(CN)C1 RNLHGQLZWXBQNY-UHFFFAOYSA-N 0.000 description 1
- HOSGXJWQVBHGLT-UHFFFAOYSA-N 6-hydroxy-3,4-dihydro-1h-quinolin-2-one Chemical group N1C(=O)CCC2=CC(O)=CC=C21 HOSGXJWQVBHGLT-UHFFFAOYSA-N 0.000 description 1
- 229910015900 BF3 Inorganic materials 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000004606 Fillers/Extenders Substances 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 206010018612 Gonorrhoea Diseases 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- BOTDANWDWHJENH-UHFFFAOYSA-N Tetraethyl orthosilicate Chemical compound CCO[Si](OCC)(OCC)OCC BOTDANWDWHJENH-UHFFFAOYSA-N 0.000 description 1
- 229910021627 Tin(IV) chloride Inorganic materials 0.000 description 1
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 1
- 239000004110 Zinc silicate Substances 0.000 description 1
- FDLQZKYLHJJBHD-UHFFFAOYSA-N [3-(aminomethyl)phenyl]methanamine Chemical compound NCC1=CC=CC(CN)=C1 FDLQZKYLHJJBHD-UHFFFAOYSA-N 0.000 description 1
- 230000002159 abnormal effect Effects 0.000 description 1
- 230000000996 additive effect Effects 0.000 description 1
- 229910052782 aluminium Inorganic materials 0.000 description 1
- VSCWAEJMTAWNJL-UHFFFAOYSA-K aluminium trichloride Chemical compound Cl[Al](Cl)Cl VSCWAEJMTAWNJL-UHFFFAOYSA-K 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 238000005452 bending Methods 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 150000001896 cresols Chemical class 0.000 description 1
- MIHINWMALJZIBX-UHFFFAOYSA-N cyclohexa-2,4-dien-1-ol Chemical class OC1CC=CC=C1 MIHINWMALJZIBX-UHFFFAOYSA-N 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 239000003085 diluting agent Substances 0.000 description 1
- 239000000539 dimer Substances 0.000 description 1
- ZZTCPWRAHWXWCH-UHFFFAOYSA-N diphenylmethanediamine Chemical compound C=1C=CC=CC=1C(N)(N)C1=CC=CC=C1 ZZTCPWRAHWXWCH-UHFFFAOYSA-N 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 239000007888 film coating Substances 0.000 description 1
- 238000009501 film coating Methods 0.000 description 1
- 239000001530 fumaric acid Substances 0.000 description 1
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 1
- 239000004845 glycidylamine epoxy resin Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 230000008676 import Effects 0.000 description 1
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- VENBJVSTINLYEU-UHFFFAOYSA-N phenol;trifluoroborane Chemical compound FB(F)F.OC1=CC=CC=C1 VENBJVSTINLYEU-UHFFFAOYSA-N 0.000 description 1
- 239000005011 phenolic resin Substances 0.000 description 1
- 229920001228 polyisocyanate Polymers 0.000 description 1
- 239000005056 polyisocyanate Substances 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 239000000047 product Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000004062 sedimentation Methods 0.000 description 1
- 230000035939 shock Effects 0.000 description 1
- 238000005480 shot peening Methods 0.000 description 1
- 229910052710 silicon Inorganic materials 0.000 description 1
- 239000010703 silicon Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 235000012222 talc Nutrition 0.000 description 1
- HPGGPRDJHPYFRM-UHFFFAOYSA-J tin(iv) chloride Chemical compound Cl[Sn](Cl)(Cl)Cl HPGGPRDJHPYFRM-UHFFFAOYSA-J 0.000 description 1
- 235000010215 titanium dioxide Nutrition 0.000 description 1
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 1
- 239000010913 used oil Substances 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
- 150000003739 xylenols Chemical class 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
- XSMMCTCMFDWXIX-UHFFFAOYSA-N zinc silicate Chemical compound [Zn+2].[O-][Si]([O-])=O XSMMCTCMFDWXIX-UHFFFAOYSA-N 0.000 description 1
- 235000019352 zinc silicate Nutrition 0.000 description 1
- NDKWCCLKSWNDBG-UHFFFAOYSA-N zinc;dioxido(dioxo)chromium Chemical compound [Zn+2].[O-][Cr]([O-])(=O)=O NDKWCCLKSWNDBG-UHFFFAOYSA-N 0.000 description 1
- 150000007934 α,β-unsaturated carboxylic acids Chemical class 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D163/00—Coating compositions based on epoxy resins; Coating compositions based on derivatives of epoxy resins
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
-
- 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
- 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
-
- 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/16—Antifouling paints; Underwater paints
- C09D5/1656—Antifouling paints; Underwater paints characterised by the film-forming substance
- C09D5/1662—Synthetic film-forming substance
Landscapes
- Chemical & Material Sciences (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Wood Science & Technology (AREA)
- Organic Chemistry (AREA)
- Paints Or Removers (AREA)
- Epoxy Resins (AREA)
Abstract
The invention provides an epoxy coating composition whose workability in coating is improved and which is excellent in an anti-corrosion property, a water-resistant property, an adhesive property and a recoating property, and is especially suitable for coating ships. The epoxy coating composition comprises (A) an epoxy resin, (B) a curing agent and (C) a modified hydrocarbon resin having a hydroxyl group and a carboxyl group in its molecule, wherein the blending amount of the (C) modified hydrocarbon resin is 10 to 500 parts by mass based on 100 parts by mass of the solid content of the (A) epoxy resin, and paint for ships and paint for general structures comprise the epoxy coating composition.
Description
Technical field
The present invention relates to not have the tar oil type epoxy coating composition, say in further detail, the operability when relating to coating is improved, and corrosion, water tolerance, cohesiveness and recoatability are excellent, is particularly suitable for the epoxy coating composition of application boats and ships.
Background technology
Present tar is epoxy coating, and corrosion, water tolerance, chemical resistant properties excellence are so be widely used in scopes such as boats and ships purposes, general works purposes.
Yet, because it contains tar, thus not only aspect environmental safety, there is hidden danger, and also black causes being difficult to carrying out colorize and selects, and use range also is restricted, and has various bad situation.
Therefore, people have developed and used oil is the no tar oil type epoxy coating of hydrocarbon resin, but because oil is a not polar functionalities of hydrocarbon resin, so the consistency of it and epoxy resin and solidifying agent is bad, phenomenons such as cured article gonorrhoea occur, is not suitable as coating.
In recent years; In order to improve the consistency of epoxy resin and solidifying agent; A kind of epoxy coating composition is disclosed in patent documentation 1, patent documentation 2, patent documentation 3, patent documentation 4 and patent documentation 5 etc.; It uses hydroxyl hydrocarbon resin, and said hydroxyl hydrocarbon resin is with unsaturated cut that is obtained by petroleum cracking and phenols polymerization gained.In addition; In patent documentation 6; Enumerated the example that uses the hydroxyl hydrocarbon resin etc., said hydrocarbon resin is 140～220 ℃ the aromatic fraction that is obtained by petroleum cracking, thereby polymerization prepares in the presence of phenols for 60～90% the high purity indenes cut that obtains through distillation.
But, along with the high mechanization of current coating, operability, the corrosion when requiring to be coated with, the water tolerance, also require high-performance such as cohesiveness, recoatability, in above-mentioned open source information scope, also there is not to satisfy the performance of these requirements.
Patent documentation 1: the spy opens clear 53-141361 communique
Patent documentation 2: the spy opens clear 54-43259 communique
Patent documentation 3: the spy opens clear 54-46258 communique
Patent documentation 4: the spy opens clear 61-203111 communique
Patent documentation 5: the spy opens flat 9-263713 communique
Patent documentation 6: the spy opens flat 11-323247 communique
Summary of the invention
The problem that the present invention will solve is to provide aforesaid, the excellent epoxy coating composition such as operability, corrosion, water tolerance, cohesiveness and recoatability when environmental safety, coating.
The inventor is in order to solve above-mentioned problem; Carried out deep research, the result finds that the consistency of the modified hydrocarbon of intramolecularly hydroxyl and carboxyl and epoxy resin, solidifying agent is excellent; And there is not the problem on the environmental safety in the epoxy coating composition that contains this modified hydrocarbon; Tone is a light color, and is excellent with wettability, corrosion, water tolerance, the recoatability of filming and the cohesiveness of pigment, thereby accomplishes the present invention.
Promptly; The invention provides a kind of epoxy coating composition; It is the epoxy coating composition that contains the modified hydrocarbon (C) that has hydroxyl and carboxyl in epoxy resin (A), solidifying agent (B) and the molecule; The use level of this modified hydrocarbon (C) is 10～500 mass parts with respect to the solids component of the epoxy resin (A) of 100 mass parts.
Epoxy coating composition of the present invention, the operability during coating, excellences such as corrosion, water tolerance, cohesiveness and recoatability, the coating that can be used as boats and ships purposes, buildings, bridge and other general works purposes uses.
The modified hydrocarbon (C) that has hydroxyl and carboxyl in the molecule; Excellent with the consistency of epoxy resin and solidifying agent, and the also excellent effect of operability, water tolerance, corrosion, cohesiveness and recoatability when finding to have cooperated the epoxy coating composition coating of this modified hydrocarbon (C).In addition, owing to do not contain tar fully, thus there is not the problem on the environment, and can form light color and film, so mainly can be effectively as the corrosion-proof paint of boats and ships with general works.
Each performance of epoxy coating composition of the present invention; Can have the two modified hydrocarbon (C) of hydroxyl and carboxyl in the molecule and obtain through using; Can think this mainly be because, there are the cause of the wettability improvement of the consistency that makes it and epoxy resin and solidifying agent, pigment in the hydroxyl that hydrophilicity is different and the mixing of carboxyl.Though think that hydroxyl is important for improving consistency, and on the other hand, when hydroxyl was too much, wetting ability increased, the result causes bad influence for water tolerance, the corrosion of coating, and then, also lowly relevant with cohesiveness.Can think that import carboxyl in right amount and can make wetting ability and hydrophobicity proper equilibrium, the result keeps identical with currently available products or better water tolerance, corrosion, cohesiveness and recoatability, and through improving pigment wettability, the operability when making coating improves.
Embodiment
Be elaborated in the face of the present invention down.
Epoxy coating composition of the present invention contains the modified hydrocarbon (C) that has hydroxyl and carboxyl in epoxy resin (A), solidifying agent (B) and the molecule.
The epoxy resin that uses in the epoxy coating composition of the present invention (A) has at least 2 above epoxy group(ing) in 1 molecule, comparatively suitable is that epoxy equivalent (weight) is 150～600, and being more preferably epoxy equivalent (weight) is 180～500.As such resin; For example can enumerate out; Present known epoxy resin such as bisphenol A type epoxy resin, aliphatics type epoxy resin, glycidyl esters type epoxy resin, glycidyl amine epoxy resin, phenol novolac-type epoxy resin, cresols type epoxy resin, dimer acid modified epoxy resin; They can only use a kind, also can use mixing more than 2 kinds.
The solidifying agent that uses in the epoxy coating composition of the present invention (B) can use as the known solidifying agent of epoxy curing agent.Can illustration go out various aliphatics or aromatic amine, polyamide resin, anhydrides, phenol resins, polymeric polyisocyanate etc.They can use a kind, also can mix more than 2 kinds and use.
Special preferred amines is a solidifying agent; For example can enumerate out the epoxy resin affixture of aliphatic polyamine classes such as m-xylene diamine, isophorone diamine, NSC 446, Triethylenetetramine (TETA), diaminodiphenyl-methane, aromatic polyamine class, these polyamines classes, polymeric amide amine, polyamide resin etc.They can only use a kind, also can use mixing more than 2 kinds.
The ratio of above-mentioned epoxy resin (A) and solidifying agent (B) can suitably be selected according to the kind of two compositions.Generally can be from respect to 100 mass parts epoxy resin being the scope selection of the solidifying agent of 10～500 mass parts.When using preferred amine to be solidifying agent as solidifying agent (B), can suitably select to make the equivalence ratio shown in (Ahew of solidifying agent (B))/(epoxy equivalent (weight) in the epoxy resin (A)) usually is 0.5～1.0 scope.
Use in the epoxy coating composition of the present invention, have the modified hydrocarbon (C) of hydroxyl and carboxyl in the molecule, contain 0.1～2.0 phenol property hydroxyl in preferred 1 molecule, be more preferably and contain 0.2～1.0 phenol property hydroxyl.In addition, the acid value of modified hydrocarbon (C), the viewpoint of the well balanced of operability, cohesiveness, water tolerance, corrosion and recoatability when being coated with, preferred 2～50 from giving.
The softening temperature of modified hydrocarbon (C) preferably makes dope viscosity suitable, and resin do not ooze out in film coated surface, does not have residual 40 ℃～150 ℃ of binding property.In addition, the scope of the preferred number average molecular weight of modified hydrocarbon (C) is 400～2500.
The usage quantity of modified hydrocarbon (C) with respect to the epoxy resin (A) of 100 mass parts, is the scope of 10～500 mass parts.Use level is during less than 10 mass parts, and the gained hardness of film is hard, and shock-resistance is bad.On the other hand, during greater than 500 mass parts, though the increase of soft film coating property, water tolerance is bad etc., and is all not preferred.
The method of manufacture of the modified hydrocarbon of using in the epoxy coating composition of the present invention (C) so long as can make the method for above-mentioned modified hydrocarbon (C), does not just have particular determination, for example, can prepare with reference to known method.If preparing method's concrete example is shown; Then can enumerate out, will contain the monoene hydro carbons and have the hydrocarbon mixture of the compounds of conjugated double bond, with the monomer mixture polymerization that contains phenols as principal constituent; With polymkeric substance that obtains and the reaction of organic unsaturated acid, thus preparation.
As the concrete example of monoene hydro carbons, can enumerate out vinylbenzene, alpha-methyl styrene, Beta-methyl vinylbenzene, Vinyl toluene, indenes and methyl indenes etc.
As the concrete example of compound, can enumerate out isoprene, 1,3-pentadiene and cyclopentadiene etc. with conjugated double bond.
As containing the phenols concrete example that contains in the monomer mixture of phenols as principal constituent, can enumerate out monohydric phenols such as phenol, ortho-cresol, meta-cresol, p-cresol, butylphenol and xylenol, and alkyl-substituted phenols such as nonylphenol and dinonyl phenol.In addition, above-mentioned phenol can mix use more than 2 kinds or 2 kinds.
As the concrete example of organic unsaturated acid, can enumerate out α, β unsaturated carboxylic acids such as vinylformic acid, methylacrylic acid, Ba Dousuan, methylene-succinic acid, maleic anhydride and fumaric acid.
Contain the monoene hydro carbons with hydrocarbon mixture, carry out the polymeric reaction conditions with the monomer mixture that contains phenols as principal constituent with compounds of conjugated double bond, can be according to the known method preparation.Specifically, can use aluminum halides such as aluminum trichloride (anhydrous) or its complex compound, boron trifluoride or friedel-crafts type catalyzer such as tin halides such as its complex compound, tin tetrachloride to carry out polymerization.
When the polymkeric substance that obtains and organic unsaturated acid addition are prepared modified hydrocarbon (C),, can carry out through the usual method heating as the concrete example of reaction conditions.
Be used to prepare containing the monoene hydro carbons and having the hydrocarbon mixture of the compounds of conjugated double bond, contain the usage quantity of monomer mixture and organic unsaturated acid of phenols as principal constituent of modified hydrocarbon (C); Because the monoene hydro carbons that contains in the hydrocarbon mixture is different with the content of the compounds with conjugated double bond; What can cause using contains the variation of phenols as the amount of the monomer mixture of principal constituent and organic unsaturated acid, so can not decide without exception.Therefore; The usage quantity of each raw material can be with suitably adjustings such as polymerizing conditions; It is good to make the consistency of gained modified hydrocarbon (C) and epoxy resin and solidifying agent have balance; Be in the scope that can show operability, cohesiveness, water tolerance, corrosion and recoatability etc. when being coated with as coating composition, for example form above-mentioned shown in phenol property hydroxyl value and acid value.
As containing the concrete example of monoene hydro carbons, can enumerate out the cut that contains the unsaturated hydrocarbons that obtains in the oil boom cracking with the hydrocarbon mixture of compounds with conjugated double bond.
In addition; As the concrete example of the cut that contains the unsaturated hydrocarbons that obtains in the oil boom cracking, can enumerate out the hydrocarbon mixture that cut (C 5 fraction) that fatty family by 20～80 ℃ of the monoolefine cut that contains aromatic structure (C9 cut) of 140～200 ℃ of boiling points and boiling points contains conjugated double bond forms.
When preparing ethene, propylene, in the C9 cut that obtains as by product, contain monoolefines such as vinylbenzene, alpha-methyl styrene, Beta-methyl vinylbenzene, Vinyl toluene, indenes and methyl indenes as reacted constituent with the oil boom cracking.In addition, in the reacted constituent of C 5 fraction, contain isoprene, 1,3-pentadiene, cyclopentadiene equiconjugate double bond monomer.
In addition; For example; Only with the C9 cut with contain phenols and carry out the polymkeric substance that polymerization obtains as the monomer mixture of principal constituent because intramolecularly do not have with organic unsaturated acid and do not react enough unsaturated link(age)s, so be difficult to through importing carboxyl with organic unsaturated acid addition.
From give water tolerance as corrosion-proof paint, corrosion, with the viewpoint of the consistency well balanced of epoxy resin and solidifying agent, preferably make with respect to C9 cut 100 mass parts, C5 is that the ratio of 1～500 mass parts is carried out copolymerization.In addition, contain 0.1～2.0 phenol property hydroxyl in preferred 1 molecule, be more preferably 0.2～1.0 phenol property hydroxyl.Suitably adjustment such as the add-on of each raw material, polymerizing condition when this can be according to polymerization.
In epoxy coating composition of the present invention; From giving flexual purpose, can be that the scope below 50 mass parts is added liquid modification agent with epoxy resin with respect to 100 mass parts; For example xylene resin, toluene resin, butyl glycidyl base ether isoreactivity resin; These additives from keeping the water tolerance aspect, preferably use fragrant family material.
In epoxy coating composition of the present invention, so as required pigment class such as proper fit pigment extender, tinting pigment, reactive diluent, organic solvent, anti-sedimentation agent, anti-sagging agent, wetting agent, reaction promotor, tack attach with agent, dewatering agent etc. usually coating with additive etc.
In addition, epoxy coating composition of the present invention preferably uses as the two component type coating that formed by host that contains epoxy resin and solidifying agent, and wherein the solidifying agent preferred amines is a solidifying agent.This two component types coating is coated with on the anti-rust coatings such as being contained in yellow zinc chromate primer paint usually.That is, at first steel plate is carried out shot-peening (shotblast) and handle, remove descaling, inorganic zinc shop primer (shop such as coating ethyl silicate system
Primer), be coated with coating composition of the present invention then.Priming paint is not limited to zinc silicate etc., can use various priming paint.
In addition,, also can carry out application, obtain sufficient corrosion protection result even there is not steel plate of priming paint etc.As coating process, can adopt that spraying, hydraulic spraying, hairbrush are coated with, known method at present such as roller coat, can being coated with aforementioned coating composition, to make dry film thickness be 150～500 μ m.
Embodiment
Below, enumerate embodiment and comparative example, further explain the present invention, but the present invention is not limited by these embodiment.
In addition, part and % represent mass parts and quality % respectively.
Embodiment 1
1) preparation of modified hydrocarbon (C)
At first in the 1st section reaction; The aromatic series C9 cut (containing 55% monoolefine) that the boiling point that the oil boom cracking obtains is 140～200 ℃ is in 100 parts; The fatty family C 5 fraction (contain 30% and have conjugated double bond) that adds 20～80 ℃ of 5 parts of boiling points; And then add 8 parts of phenol, keep 20 ℃ of temperature of reaction, simultaneously with the catalyzer boron trifluoride-phenol complex that dripped 1.0 parts in 1 hour.Under identical temperature, slaking 4 hours finishes reaction then.Then, use the sodium hydroxide solution decomposition catalyst, wash, remove unreacted oil and oligopolymer through underpressure distillation then, obtain containing in the molecule 60 parts of the unsaturated hydrocarbons resins of the hydroxyl of 0.6 hydroxyl.
Then,, in 40 parts of the 1st section resins that reaction obtains, add 0.4 part of maleic anhydride,, carry out reduced pressure treatment then, remove unreacted maleic anhydride 200 ℃ of reactions 3 hours down as the 2nd section reaction.Obtaining the resin acid value is 6, the modified hydrocarbon of hydroxyl and carboxyl (C) in the molecule.In addition, the softening temperature of gained modified hydrocarbon (C) is 98 ℃.
The shape of gained resin is as shown in table 1.
2) coatingization
In container, add 100 parts epoxy resin, 50 parts of titanium whites, 100 parts of talcums, 120 parts of modified hydrocarbon (C), 5 parts of anti-sagging agents and softening agent of 15 parts, 50 parts mixed solvent (MIBK/ YLENE; 25/25),, processes host with stirrer mixing homogeneous.To the 80 parts of polyamide resins (solids component conversion) that wherein add as solidifying agent, mix and stir, obtain epoxy coating composition.Composition and coating assessment result are shown in table 2, table 3.
Embodiment 2～4
According to prescription shown in the table 1, under the condition identical, prepare modified hydrocarbon (C) with embodiment.Its proterties is as shown in table 1.
About coatingization, carry out coatingization with the same method of method shown in the embodiment 1.Composition and coating assessment result are shown in table 2, table 3.
Comparative preparation example 1
1) preparation of resin
Except in the 1st section reaction, using 100 parts of C9 cuts, 8 parts the phenol, all the other to be carrying out polymerization with embodiment 1 identical condition, thereby are not contained the hydrocarbon resin of the hydroxyl of the structural unit that C 5 fraction produces.Do not carry out the addition reaction with maleic anhydride through ensuing the 2nd section reaction.The proterties of gained resin is as shown in table 1.
2) coatingization
About coatingization, use with the identical method of method shown in the embodiment 1 and carry out coatingization.Composition and coating assessment result are shown in table 2, table 3.
Comparative preparation example 2
1) preparation of resin
Except in the 1st section reaction, only using 100 parts of C9 cuts, all the other to be carrying out polymerization with embodiment 1 identical condition, thus do not contained structural unit that C 5 fraction and phenol produces, the hydrocarbon resin of hydroxyl not.
In ensuing the 2nd section reaction, in 40 parts of these resins, add 0.4 part maleic anhydride, attempt to carry out with embodiment 1 same with addition reaction maleic anhydride.But different with embodiment 1, gained resin acid value is low, and value is 1.0.Infer this be because, the resin that obtains in the 1st section reaction does not have the enough unsaturated link(age)s that are used to carry out addition reaction, so reactive bad.
The proterties of gained resin is as shown in table 1.
2) coatingization
About coatingization, use with the same method of method shown in the embodiment 1 and carry out coatingization.Composition and coating assessment result are shown in table 2, table 3.
Comparative preparation example 3
1) preparation of resin
In 40 parts of the hydrocarbon resins of the hydroxyl that comparative example 1 obtains, add 0.4 part of maleic anhydride, attempt carrying out the 2nd section reaction, but same reactive bad with comparative example 2, the resin acid value that obtains is low, and value is 0.7.
Gained resin proterties is as shown in table 1.
2) coatingization
About coatingization, use with method shown in the embodiment 1 and carry out coatingization with quadrat method.Composition and coating assessment result are shown in table 2, table 3.
[table 1]
※ 1) maleic anhydride and acrylic acid numeral be the quality % with respect to the unsaturated hydrocarbons resin of hydroxyl
[table 2]
※ 2) worker ピ コ one ト #1001/#828=50/50 (ジ ャ パ Application worker Port キ シ レ ジ Application society system)
※ 3) the not carboxylic hydroxyl hydrocarbon resin that obtains in the comparative preparation example 1
※ 4) hydrocarbon resin of the not hydroxyl that obtains in the comparative preparation example 2
※ 5) hydrocarbon resin of the hydroxyl that obtains in the comparative preparation example 3
※ 6) ニ カ ノ one Le L xylene resin (the ガ ス of Mitsubishi chemistry society system)
※ 7) デ イ ス パ ロ Application A-630 (nanmu originally changes into society's system)
※ 8) mixed solvent (equal amount of mixture of YLENE/MIBK)
※ 9) polyamide resin; バ one サ ミ De 115 (ヘ Application ケ Le plain boiled water society system)
[table 3]
※ 10) Du Pont's shock test of JISK-5400-1990 regulation
Test piece use degreasing polishing mild steel plate (200 * 100 * 0.6mm) go up with spreadometer coating written treaty 250 μ m thickness, under 20 ℃ * 65%RH atmosphere dry 7 days, thereby the test film of processing.※ 11) carry out cold-resistant thermogravimetric retrial and test according to JISK-5400-1990
The test piece use is silicon-coated phosphate-gallate series priming paint on degreasing polishing mild steel plate, makes thickness be about 20 μ m, after dry 1 day, is coated with the test piece of written treaty 250 μ m film (using 7 days test piece of drying under 20 ℃ * 65%RH) with spreadometer.
※ 12) will the test piece identical with ※ 10, dipping is 6 months in 50 ℃ seawater, its coated surface of visual valuation.
Zero: no abnormal Δ: occur a little bubbling (blister) *: significantly occur bubbling
※ 13) use the test piece of ※ 10, under 20 ℃ of atmosphere, will be coated with towards outer lateral buckling 90 degree, the be full of cracks that the visual valuation bending part is filmed.
Zero: do not have the be full of cracks Δ: have a little *: quite a lot of
※ 14) test piece uses the no priming paint test piece of degreasing polishing mild steel plate, the brushing operability when estimating coating.
Zero: the homogeneous of filming, stretch, operate good Δ: the stretching, extension that homogeneous is filmed, operability are bad a little
※ 15) on degreasing polishing mild steel plate with spreadometer coating written treaty 200 μ m, under 20 ℃ * 65%RH atmosphere dry 7 days, and then be coated with on 1 time the face coating (200 μ m) the 2nd time, dry 3 days.Be made into test piece.
Test piece was flooded in seawater 30 days, peel off adhiesion test (5mm is wide), estimate splitting with cutter.
Zero: good Δ: splitting occurs
Shown in the embodiment 1～3 of table 3, epoxy coating composition of the present invention, excellences such as operability when water tolerance, cohesiveness, corrosion, coating and recoatability.In addition, owing to do not contain tar fully,, and can form light color and film, so be useful as the corrosion-proof paint of boats and ships, general works so there is not the problem on the environment.
Claims (5)
1. epoxy coating composition; It is the epoxy coating composition that contains the modified hydrocarbon (C) that has hydroxyl and carboxyl in epoxy resin (A), solidifying agent (B) and the molecule; This modified hydrocarbon (C) be contain in 1 molecule that 0.1～2.0 phenol property hydroxyl, acid value are 2～50, softening temperature is that 40 ℃～150 ℃ and number-average molecular weight are 400～2500 modified hydrocarbon; The use level of this modified hydrocarbon (C) is 10～500 mass parts with respect to the solids component of the epoxy resin (A) of 100 mass parts.
2. epoxy coating composition as claimed in claim 1; Wherein, Modified hydrocarbon (C) is through containing monoene hydro carbons and the hydrocarbon mixture with compounds of conjugated double bond; With contain the monomer mixture of phenols and carry out polymerization as principal constituent, organic unsaturated acid and resulting polymers are reacted prepare.
3. epoxy coating composition as claimed in claim 2; Wherein, Contain the monoene hydro carbons and have the hydrocarbon mixture of the compounds of conjugated double bond, the monoolefine cut that contains aromatic structure that the boiling point that is obtained by the oil boom cracking is 140～200 ℃ is that the cut that the fatty family of 20～80 ℃ of C9 cut and boiling points contains conjugated double bond is that C 5 fraction constitutes.
4. boats and ships are used coating, contain each described epoxy coating composition of claim 1～3.
5. a general works is used coating, contains each described epoxy coating composition of claim 1～3.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/JP2005/005385 WO2006100778A1 (en) | 2005-03-24 | 2005-03-24 | Epoxy coating composition |
Publications (2)
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| CN101133133A CN101133133A (en) | 2008-02-27 |
| CN101133133B true CN101133133B (en) | 2012-06-27 |
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| CN2005800488014A Expired - Fee Related CN101133133B (en) | 2005-03-24 | 2005-03-24 | Epoxy coating composition |
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| KR (1) | KR101194454B1 (en) |
| CN (1) | CN101133133B (en) |
| HK (1) | HK1118306A1 (en) |
| WO (1) | WO2006100778A1 (en) |
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| KR100934637B1 (en) * | 2009-04-07 | 2009-12-31 | 동해케미칼공업주식회사 | Water epoxy paint composition equipped hydrophobicity |
| JP2012256872A (en) * | 2011-05-12 | 2012-12-27 | Rohm & Haas Electronic Materials Llc | Adhesion promotion of metal to dielectric |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1185799A (en) * | 1996-03-28 | 1998-06-24 | 关西涂料株式会社 | Anticorrosive coating composition |
| CN1272125A (en) * | 1998-05-13 | 2000-11-01 | 日本石油化学株式会社 | Coating composition for corrosion proofing |
| JP2002348515A (en) * | 2001-05-28 | 2002-12-04 | Arakawa Chem Ind Co Ltd | Binder for printing ink, printing ink containing the binder for printing ink, coating agent and coating composition |
| JP2003171611A (en) * | 2001-12-07 | 2003-06-20 | Chugoku Marine Paints Ltd | Epoxy resin composition capable of forming coating film having high extensibility, anticorrosive coating composition, its coating film, base material coated with its film, and method for preventing corrosion of base material |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
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| JP4283642B2 (en) * | 2003-10-06 | 2009-06-24 | 東邦化学工業株式会社 | Epoxy paint composition |
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2005
- 2005-03-24 WO PCT/JP2005/005385 patent/WO2006100778A1/en not_active Application Discontinuation
- 2005-03-24 CN CN2005800488014A patent/CN101133133B/en not_active Expired - Fee Related
- 2005-03-24 KR KR1020077018307A patent/KR101194454B1/en not_active IP Right Cessation
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Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1185799A (en) * | 1996-03-28 | 1998-06-24 | 关西涂料株式会社 | Anticorrosive coating composition |
| CN1272125A (en) * | 1998-05-13 | 2000-11-01 | 日本石油化学株式会社 | Coating composition for corrosion proofing |
| JP2002348515A (en) * | 2001-05-28 | 2002-12-04 | Arakawa Chem Ind Co Ltd | Binder for printing ink, printing ink containing the binder for printing ink, coating agent and coating composition |
| JP2003171611A (en) * | 2001-12-07 | 2003-06-20 | Chugoku Marine Paints Ltd | Epoxy resin composition capable of forming coating film having high extensibility, anticorrosive coating composition, its coating film, base material coated with its film, and method for preventing corrosion of base material |
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| Publication number | Publication date |
|---|---|
| HK1118306A1 (en) | 2009-02-06 |
| WO2006100778A1 (en) | 2006-09-28 |
| CN101133133A (en) | 2008-02-27 |
| KR101194454B1 (en) | 2012-10-24 |
| KR20070118592A (en) | 2007-12-17 |
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