JPS62288667A - Coating compound composition - Google Patents
Coating compound compositionInfo
- Publication number
- JPS62288667A JPS62288667A JP13178786A JP13178786A JPS62288667A JP S62288667 A JPS62288667 A JP S62288667A JP 13178786 A JP13178786 A JP 13178786A JP 13178786 A JP13178786 A JP 13178786A JP S62288667 A JPS62288667 A JP S62288667A
- Authority
- JP
- Japan
- Prior art keywords
- acrylic acid
- component
- resin
- parts
- reaction product
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Pending
Links
- 150000001875 compounds Chemical class 0.000 title claims abstract description 9
- 239000011248 coating agent Substances 0.000 title abstract description 11
- 238000000576 coating method Methods 0.000 title abstract description 11
- 239000000203 mixture Substances 0.000 title abstract description 10
- NIXOWILDQLNWCW-UHFFFAOYSA-N 2-Propenoic acid Natural products OC(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims abstract description 23
- SMZOUWXMTYCWNB-UHFFFAOYSA-N 2-(2-methoxy-5-methylphenyl)ethanamine Chemical compound COC1=CC=C(C)C=C1CCN SMZOUWXMTYCWNB-UHFFFAOYSA-N 0.000 claims abstract description 22
- 229920005989 resin Polymers 0.000 claims abstract description 16
- 239000011347 resin Substances 0.000 claims abstract description 16
- FQYUMYWMJTYZTK-UHFFFAOYSA-N Phenyl glycidyl ether Chemical compound C1OC1COC1=CC=CC=C1 FQYUMYWMJTYZTK-UHFFFAOYSA-N 0.000 claims abstract description 11
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 claims abstract description 10
- 239000003822 epoxy resin Substances 0.000 claims abstract description 9
- 229920000647 polyepoxide Polymers 0.000 claims abstract description 9
- 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 claims abstract description 8
- 229920002037 poly(vinyl butyral) polymer Polymers 0.000 claims abstract description 8
- 239000007795 chemical reaction product Substances 0.000 claims abstract description 7
- 239000003999 initiator Substances 0.000 claims abstract description 6
- 229920001577 copolymer Polymers 0.000 claims abstract description 5
- 229920000191 poly(N-vinyl pyrrolidone) Polymers 0.000 claims abstract description 5
- 229930185605 Bisphenol Natural products 0.000 claims abstract description 3
- 239000008199 coating composition Substances 0.000 claims description 16
- 239000000126 substance Substances 0.000 claims description 8
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 claims description 3
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 abstract description 10
- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 abstract description 8
- ISAOCJYIOMOJEB-UHFFFAOYSA-N benzoin Chemical compound C=1C=CC=CC=1C(O)C(=O)C1=CC=CC=C1 ISAOCJYIOMOJEB-UHFFFAOYSA-N 0.000 abstract description 7
- 238000002156 mixing Methods 0.000 abstract description 6
- 239000003513 alkali Substances 0.000 abstract description 5
- 244000028419 Styrax benzoin Species 0.000 abstract description 4
- 235000000126 Styrax benzoin Nutrition 0.000 abstract description 4
- 235000008411 Sumatra benzointree Nutrition 0.000 abstract description 4
- 229960002130 benzoin Drugs 0.000 abstract description 4
- 235000019382 gum benzoic Nutrition 0.000 abstract description 4
- 230000002265 prevention Effects 0.000 abstract description 4
- 229910000831 Steel Inorganic materials 0.000 description 13
- 239000010959 steel Substances 0.000 description 13
- -1 phosphate ester Chemical class 0.000 description 7
- 239000000047 product Substances 0.000 description 5
- KCTAWXVAICEBSD-UHFFFAOYSA-N prop-2-enoyloxy prop-2-eneperoxoate Chemical compound C=CC(=O)OOOC(=O)C=C KCTAWXVAICEBSD-UHFFFAOYSA-N 0.000 description 5
- 239000012956 1-hydroxycyclohexylphenyl-ketone Substances 0.000 description 4
- OMIGHNLMNHATMP-UHFFFAOYSA-N 2-hydroxyethyl prop-2-enoate Chemical compound OCCOC(=O)C=C OMIGHNLMNHATMP-UHFFFAOYSA-N 0.000 description 4
- MQDJYUACMFCOFT-UHFFFAOYSA-N bis[2-(1-hydroxycyclohexyl)phenyl]methanone Chemical compound C=1C=CC=C(C(=O)C=2C(=CC=CC=2)C2(O)CCCCC2)C=1C1(O)CCCCC1 MQDJYUACMFCOFT-UHFFFAOYSA-N 0.000 description 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- QNODIIQQMGDSEF-UHFFFAOYSA-N (1-hydroxycyclohexyl)-phenylmethanone Chemical compound C=1C=CC=CC=1C(=O)C1(O)CCCCC1 QNODIIQQMGDSEF-UHFFFAOYSA-N 0.000 description 3
- 229920000298 Cellophane Polymers 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
- 239000002253 acid Substances 0.000 description 3
- 150000003839 salts Chemical class 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- 239000004593 Epoxy Substances 0.000 description 2
- WOBHKFSMXKNTIM-UHFFFAOYSA-N Hydroxyethyl methacrylate Chemical compound CC(=C)C(=O)OCCO WOBHKFSMXKNTIM-UHFFFAOYSA-N 0.000 description 2
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000012752 auxiliary agent Substances 0.000 description 2
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 2
- 230000000052 comparative effect Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 239000000463 material Substances 0.000 description 2
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 2
- 229910052753 mercury Inorganic materials 0.000 description 2
- 239000004814 polyurethane Substances 0.000 description 2
- 229920002635 polyurethane Polymers 0.000 description 2
- 230000003449 preventive effect Effects 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- MUTGBJKUEZFXGO-OLQVQODUSA-N (3as,7ar)-3a,4,5,6,7,7a-hexahydro-2-benzofuran-1,3-dione Chemical compound C1CCC[C@@H]2C(=O)OC(=O)[C@@H]21 MUTGBJKUEZFXGO-OLQVQODUSA-N 0.000 description 1
- HQMPQWNDYLFQBX-UHFFFAOYSA-N 2,2-dichloro-2-phenoxy-1-phenylethanone Chemical compound C=1C=CC=CC=1C(=O)C(Cl)(Cl)OC1=CC=CC=C1 HQMPQWNDYLFQBX-UHFFFAOYSA-N 0.000 description 1
- FPKCTSIVDAWGFA-UHFFFAOYSA-N 2-chloroanthracene-9,10-dione Chemical compound C1=CC=C2C(=O)C3=CC(Cl)=CC=C3C(=O)C2=C1 FPKCTSIVDAWGFA-UHFFFAOYSA-N 0.000 description 1
- KMNCBSZOIQAUFX-UHFFFAOYSA-N 2-ethoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OCC)C(=O)C1=CC=CC=C1 KMNCBSZOIQAUFX-UHFFFAOYSA-N 0.000 description 1
- SJEBAWHUJDUKQK-UHFFFAOYSA-N 2-ethylanthraquinone Chemical compound C1=CC=C2C(=O)C3=CC(CC)=CC=C3C(=O)C2=C1 SJEBAWHUJDUKQK-UHFFFAOYSA-N 0.000 description 1
- XPXOSCCUYBNIRN-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenyl-4-propyldodecan-1-one Chemical compound CCCCCCCCC(CCC)CC(C)(O)C(=O)C1=CC=CC=C1 XPXOSCCUYBNIRN-UHFFFAOYSA-N 0.000 description 1
- XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical compound CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 description 1
- 125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
- BQZJOQXSCSZQPS-UHFFFAOYSA-N 2-methoxy-1,2-diphenylethanone Chemical compound C=1C=CC=CC=1C(OC)C(=O)C1=CC=CC=C1 BQZJOQXSCSZQPS-UHFFFAOYSA-N 0.000 description 1
- RZVINYQDSSQUKO-UHFFFAOYSA-N 2-phenoxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC1=CC=CC=C1 RZVINYQDSSQUKO-UHFFFAOYSA-N 0.000 description 1
- ARXVXVOLXMVYIT-UHFFFAOYSA-N 3-methylbutyl 2-(dimethylamino)benzoate Chemical compound CC(C)CCOC(=O)C1=CC=CC=C1N(C)C ARXVXVOLXMVYIT-UHFFFAOYSA-N 0.000 description 1
- 229920005731 JONCRYL® 67 Polymers 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 1
- DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 description 1
- STWYYQVVABMBIZ-UHFFFAOYSA-N [hydroxy(2-hydroxyethoxy)phosphoryl] 2-methylprop-2-enoate Chemical compound CC(=C)C(=O)OP(O)(=O)OCCO STWYYQVVABMBIZ-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 239000004841 bisphenol A epoxy resin Substances 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- QSAWQNUELGIYBC-UHFFFAOYSA-N cyclohexane-1,2-dicarboxylic acid Chemical compound OC(=O)C1CCCCC1C(O)=O QSAWQNUELGIYBC-UHFFFAOYSA-N 0.000 description 1
- 230000002950 deficient Effects 0.000 description 1
- 238000010586 diagram Methods 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- 125000001033 ether group Chemical group 0.000 description 1
- 239000003112 inhibitor Substances 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003014 phosphoric acid esters Chemical class 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 150000003077 polyols Chemical class 0.000 description 1
- HXHCOXPZCUFAJI-UHFFFAOYSA-N prop-2-enoic acid;styrene Chemical compound OC(=O)C=C.C=CC1=CC=CC=C1 HXHCOXPZCUFAJI-UHFFFAOYSA-N 0.000 description 1
- KRIOVPPHQSLHCZ-UHFFFAOYSA-N propiophenone Chemical class CCC(=O)C1=CC=CC=C1 KRIOVPPHQSLHCZ-UHFFFAOYSA-N 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- YRHRIQCWCFGUEQ-UHFFFAOYSA-N thioxanthen-9-one Chemical compound C1=CC=C2C(=O)C3=CC=CC=C3SC2=C1 YRHRIQCWCFGUEQ-UHFFFAOYSA-N 0.000 description 1
- 239000006097 ultraviolet radiation absorber Substances 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 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
- C09D5/00—Coating compositions, e.g. paints, varnishes or lacquers, characterised by their physical nature or the effects produced; Filling pastes
- C09D5/008—Temporary coatings
-
- 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
- C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
- C09D4/06—Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond in combination with a macromolecular compound other than an unsaturated polymer of groups C09D159/00 - C09D187/00
-
- 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
Abstract
Description
【発明の詳細な説明】
（産業上の利用分野）
本発明は鋼材の一時防錆処理に有用で防錆性、密着性と
アルカリによる脱膜性が良好な、紫外線で硬化する塗料
組成物に関するものである。Detailed Description of the Invention (Field of Industrial Application) The present invention relates to a coating composition that cures with ultraviolet light and is useful for temporary rust prevention treatment of steel materials and has good rust prevention, adhesion, and alkali removability. It is something.
（従来の技術） 鋼材とは、例えば、棒鋼、形鋼、圧延鋼板。(Conventional technology) Examples of steel materials include steel bars, shaped steel, and rolled steel plates.
表面処理鋼板、鋼管、線材等があり、これらは通常、製
造水から需要家に至るまでの期間、防錆を目的として防
錆剤で被覆処理されている。There are surface-treated steel plates, steel pipes, wire rods, etc., and these are usually coated with a rust preventive agent for the purpose of rust prevention during the period from produced water to consumers.
近年、短時間で硬化することを利用して、紫外線硬化型
防錆剤が利用されるようになり、各種のものが提案され
ている。例えば、特開昭５２−１１０７３８には、アク
リル系オリゴマーとアクリロイルオキシ基を有す有機リ
ン酸エステルを配合した活性エネルギー線硬化性被覆組
成物が、特開昭５３−６３３６忙は、アクリル系オリゴ
マーとポリビニルブチラール樹脂を配合した光硬化性塗
料組成物が記載されている。In recent years, UV-curable rust preventives have come into use because they cure in a short time, and various types have been proposed. For example, JP-A-52-110738 discloses an active energy ray-curable coating composition containing an acrylic oligomer and an organic phosphate ester having an acryloyloxy group; A photocurable coating composition containing a polyvinyl butyral resin and a polyvinyl butyral resin is described.
（発明が解決しようとする問題点〕
上記の組成物より得られる被膜は、アルカリによる脱膜
に時間がかかったり、密着性に劣り使用する上で問題が
ある。(Problems to be Solved by the Invention) The film obtained from the above composition has problems in use because it takes time to remove the film with alkali and has poor adhesion.
（問題点を解決するための手段）
上記の問題を解決するため、本発明者らは、鋭意研究の
結果、得られた樹脂被膜のアルカリによる脱膜の速度が
速く、密着性、耐塩水性の良好な塗料組成物を提供する
ことに成功し、本発明を完成した。(Means for Solving the Problems) In order to solve the above problems, the inventors of the present invention have conducted extensive research and found that the resulting resin film has a high rate of removal with alkali and has excellent adhesion and salt water resistance. The present invention was completed by successfully providing a good coating composition.
即ち、本発明は、
（１） ポリ−Ｎ−ビニルピロリドン又はスチレンと
（メタ）アクリル酸の共重合物又はポリビニルブチラー
ル樹脂の中より選ばれる樹脂図と、一般式〔Ｉ〕
（式０）中、ＲｓはＨ又はＣＨ３，Ｒ２はで＝〉−又は
Ｄ である。）
で表わされる化合物（Ｂ）とフェニルグリシジルエーテ
ルとアクリル酸の反応物Ｃ）とビスフェノール型エポキ
シ樹脂とアクリル酸の反応物（Ｄｌと光重合開始剤（Ｅ
ｌを含む事を特徴とする塗料組成物に関する。That is, the present invention provides: (1) a resin diagram selected from poly-N-vinylpyrrolidone, a copolymer of styrene and (meth)acrylic acid, or polyvinyl butyral resin; , Rs is H or CH3, R2 is =>- or D. ) A reaction product of compound (B), phenyl glycidyl ether, and acrylic acid C), a reaction product of bisphenol-type epoxy resin, and acrylic acid (Dl, and a photopolymerization initiator (E
The present invention relates to a coating composition characterized in that it contains l.
本発明は樹脂図を使用するが、それらは、市場より容易
に入手することができる。例えば、ポリ−Ｎ−ビニルピ
ロリドンＣＢＡＳＦ社裂、ルビスコールに３０．ルビス
コールに９（１）、スチレンと（メタ）アクリル酸の共
重合物（ジシンンン・ワックス社製、ジョンクリル６７
等）、ポリビニルブチラール樹脂（種水化学工業■裂ニ
スレックスＢＬ−８等）等である。本発明の塗料組成物
において樹脂（５）は組成物中０．５〜１５重量％の範
囲で使用するのが好ましく、特に１〜１０重量％の範囲
で使用するのが好ましい。The present invention uses resin figures, which are readily available on the market. For example, poly-N-vinylpyrrolidone CBASF, Rubiskol has a 9(1) in Rubiscoll, a copolymer of styrene and (meth)acrylic acid (manufactured by Dishinne Wax Co., Ltd., Joncryl 67
etc.), polyvinyl butyral resins (Tanamizu Kagaku Kogyo Nisrex BL-8, etc.), and the like. In the coating composition of the present invention, the resin (5) is preferably used in an amount of 0.5 to 15% by weight, particularly preferably 1 to 10% by weight.
本発明では、一般式ＣＤで表わされる化合物の）を使用
する。化合物（Ｂ）は、フタル酸、ヘキサヒドロフタル
酸又はこれら酸の無水物と２−ヒドロキシエチルメタク
リレート又は２−ヒドロキシエチルアクリレートとを自
体公知の反応をせしめることによって得られる。In the present invention, a compound represented by the general formula CD is used. Compound (B) can be obtained by reacting phthalic acid, hexahydrophthalic acid or anhydrides of these acids with 2-hydroxyethyl methacrylate or 2-hydroxyethyl acrylate in a manner known per se.
化合物（Ｂ）の使用量は、組成物中３〜６０重量％の範
囲で使用するのが好ましく、特に５〜５０重量％の範囲
で使用するのが好ましい。本発明では、フェニルグリシ
ジルエーテルとアクリル酸の反応物（Ｑを使用するが、
これは、容易に市場より入手することができる。（例え
ば、日本化薬１凱ＫＡＹＡＲＡＤＲ−１２８等）。反応
物（Ｑの使用量は、組成物中、１〜５０重量％の範囲で
使用するのが好ましく、特に３〜４０重量％で使用する
のが好ましい。本発明では、ビスフェノール型エポキシ
樹脂（例えば、シェル化学■裂、エピコート８２８．１
００１．１００４等）とアクリル酸の反応物Ｑ））を使
用するが、これは、上記エポキシ樹脂とアクリル酸の自
体公知の付加Ａよって得られる。反応物（Ｄ）の使用量
は、−組成物中０．５〜１５重量％の範囲で使用するの
が好ましく、特に１〜１０重量％で使用するのが好まし
い。又、更に、の）成分の光重合開始剤としては、例え
ば、ベンゾイン、ベンゾインメチルエーテル、ベンゾイ
ンエチルエーテル、ペンゾインイソグロビルエーテルナ
トのベンゾインアルキルエーテル系、２，２−ジェトキ
シアセトフェノン、４−フェノキシ−２，２−ジクロロ
アセトフェノンなどのアセトフェノン系、２−ヒドロキ
シ−２−メチルプロピオフェノン。The amount of compound (B) to be used in the composition is preferably 3 to 60% by weight, particularly preferably 5 to 50% by weight. In the present invention, a reaction product of phenyl glycidyl ether and acrylic acid (Q is used,
This can be easily obtained from the market. (For example, Nippon Kayaku 1kai KAYARADR-128, etc.). The amount of the reactant (Q) used in the composition is preferably 1 to 50% by weight, particularly 3 to 40% by weight.In the present invention, bisphenol type epoxy resin (e.g. , Shell Chemical ■Crack, Epicote 828.1
001.1004, etc.) and acrylic acid is used, which is obtained by the known addition A of the epoxy resin and acrylic acid described above. The amount of reactant (D) to be used is preferably in the range of 0.5 to 15% by weight, particularly preferably 1 to 10% by weight in the composition. Further, as the photopolymerization initiator of component (), for example, benzoin, benzoin methyl ether, benzoin ethyl ether, benzoin alkyl ether type of benzoin isoglobil ether nato, 2,2-jethoxyacetophenone, 4 - Acetophenone series such as phenoxy-2,2-dichloroacetophenone, 2-hydroxy-2-methylpropiophenone.
４′−イソプロビル−２−ヒドロキシ−２−メチルプロ
ピオフェノン、４−ドデシル−２−ヒドロキシ−２−メ
チルプロピオフェノンなどのプロピオフェノン系、ベン
ジルジメチルケタール、１−ヒドロキシシクロへキシル
フェニルケトン及び２−エチルアントラキノン、２−ク
ロルアントラキノン系その他、チオキサントン系光重合
開始剤などがあげられる。Propiophenone series such as 4'-isoprobyl-2-hydroxy-2-methylpropiophenone, 4-dodecyl-2-hydroxy-2-methylpropiophenone, benzyl dimethyl ketal, 1-hydroxycyclohexylphenyl ketone and 2-ethylanthraquinone, 2-chloroanthraquinone, and thioxanthone-based photopolymerization initiators.
特に好ましいものとしては、ｌ−ヒドロキシシクロへキ
シルフェニルケトン、ベンジルジメチルケタール等があ
げられる。その使用量は、通常、組成物の０．１〜ｉｏ
重量％が、特に１〜５重量％が好ましい。Particularly preferred are l-hydroxycyclohexylphenyl ketone, benzyl dimethyl ketal, and the like. The amount used is usually 0.1 to io of the composition.
% by weight, especially 1 to 5% by weight is preferred.
これら光重合開始剤は必要に応じて硬化性を高めるため
Ｎ、Ｎ−ジメチルアミノ安息香酸イソアミルエステル等
の助剤と併用させることもできる。These photopolymerization initiators can be used in combination with an auxiliary agent such as N,N-dimethylaminobenzoic acid isoamyl ester to improve curability, if necessary.
本発明の組成物は、更に必要に応じて、ポリエステルア
クリレート、ポリウレタンアクリレート、例えば分子中
にエーテル基、エステル基を持ったポリオールのポリウ
レタンアクリレートするいは重合性モノマー、例えば、
フェニルオキシポリエトキシアクリレート、フェニルオ
キシエチルアクリレート、トリメチロールプロパントリ
アクリレート、２−ヒドロキシエチル〔メタコアクリレ
ートのリン酸エステル（日本化薬■裂、ＫＡＹＡＭＡ後
Ｍ１．ＰＭ２等）、ヒドロキシヒバリン酸ネオペンチル
グリコールジアクリレート（日本化薬■製、ＫＡＹＡＲ
ＡＤ ＭＡＮＤＡ）等を加えて用いることができる。ま
た、所望により、紫外線吸収剤１重合禁止剤、溶剤、そ
の他の助剤を配合しても良い。本発明の組成物は金属面
に直接に塗布される。塗布は、ロールコータ−１刷毛塗
り、スプレー塗装等により行われる。本発明の塗料組成
物は、紫外線を照射することにより曖時に硬化する。本
発明の塗料組成物の紫外線照射による硬化は常法により
行うことができる。例えば、低圧又は高圧水銀灯、キセ
ノン灯等を用い紫外線を照射すればよい。The composition of the present invention may further include polyester acrylate, polyurethane acrylate, for example, polyurethane acrylate of a polyol having an ether group or ester group in the molecule, or a polymerizable monomer, for example, as necessary.
Phenyloxypolyethoxy acrylate, phenyloxyethyl acrylate, trimethylolpropane triacrylate, 2-hydroxyethyl [phosphoric acid ester of methacrylate (Nippon Kayaku, KAYAMA M1.PM2, etc.), neopentyl glycol dihydroxyhybalate Acrylate (manufactured by Nippon Kayaku, KAYAR)
AD MANDA) etc. can be used in addition. Further, if desired, an ultraviolet absorber 1 polymerization inhibitor, a solvent, and other auxiliary agents may be blended. The compositions of the invention are applied directly to metal surfaces. The coating is performed by brush coating with a roll coater 1, spray coating, or the like. The coating composition of the present invention is cured by irradiation with ultraviolet rays. Curing of the coating composition of the present invention by ultraviolet irradiation can be carried out by a conventional method. For example, ultraviolet rays may be irradiated using a low-pressure or high-pressure mercury lamp, a xenon lamp, or the like.
（実施例）
実施例１゜
ポリ−Ｎ−ビニルピロリドン（ＢＡＳＦ社裂、ルビスコ
ールに一３ｏ）５部、ヘキサヒドロ無水フタル酸と２−
ヒドロキシエチルアクリレートを等モル反応させて得ら
れるカルボキシル基を有するアクリレート（分子量２７
０．１８、酸価２０７、７ ｍｇＫＯＨ／ｇ） ４２部
、フェニルグリシジルエーテル１モルにアクリル酸１モ
ルヲ反応して得たモノアクリレート（日本化薬■製、Ｋ
ＡＹＡＲＡＤ Ｒ−１２８）２９部、フェニルオキシ
ポリエチルアクリレート（日本化薬■製、ＫＡＹＡＲＡ
Ｄ Ｒ−５６４） １８．６部、ビスフェノールＡ型
エポキシ樹脂（シェル化学■裂、エピコート１００４、
分子量１８２０．エポキシ当量９１１）１モルにアクリ
ル酸１．９モルを反応して得１こエポキシアクリレート
５．４部、１−ヒドロキシジークロへキシルフェニルケ
トン（チパ・ガイキー■裂、イルガキュアー１８４）５
部を混合し、塗料組成物Ａを調製した。硬化物の特性を
第１表に示す。(Example) Example 1゜5 parts of poly-N-vinylpyrrolidone (BASF Ltd., Rubiscoll 130%), hexahydrophthalic anhydride and 2-
Acrylate having a carboxyl group obtained by reacting equimolar amounts of hydroxyethyl acrylate (molecular weight 27
0.18, acid value 207, 7 mgKOH/g) 42 parts, monoacrylate obtained by reacting 1 mole of acrylic acid with 1 mole of phenyl glycidyl ether (manufactured by Nippon Kayaku ■, K
AYARAD R-128) 29 parts, phenyloxypolyethyl acrylate (manufactured by Nippon Kayaku ■, KAYARA
DR-564) 18.6 parts, bisphenol A type epoxy resin (Shell Kagaku ■Shitsu, Epicoat 1004,
Molecular weight 1820. 5.4 parts of epoxy acrylate obtained by reacting 1 mole of epoxy equivalent (911) with 1.9 mole of acrylic acid, 5.4 parts of 1-hydroxy dichlorohexyl phenyl ketone (Chipa Geikii, Irgacure 184)
A coating composition A was prepared by mixing the following parts. Table 1 shows the properties of the cured product.
実施例２゜
スチレンとアクリル酸の共重合物（ジョンソン・ワック
ス社■裂、シコンクリル６７）３部。Example 2 3 parts of a copolymer of styrene and acrylic acid (Johnson Wax Co., Ltd., Siconcryl 67).
無水フタル酸と２−ヒドロキシエチルアクリレートを等
モル反応させて得られるカルボキシル基を有するアクリ
レート（分子量２６４．１２、酸価２１２．４４ ｍｇ
ＫＯＨ／ｇ ） ５０部、フェニルグリシジルエーテル
１モルにアクリル酸１モルを反応して得たモノアクリレ
ート（日本化薬■製。Acrylate with carboxyl group obtained by reacting equimolar amounts of phthalic anhydride and 2-hydroxyethyl acrylate (molecular weight 264.12, acid value 212.44 mg)
KOH/g) 50 parts, monoacrylate obtained by reacting 1 mole of phenyl glycidyl ether with 1 mole of acrylic acid (manufactured by Nippon Kayaku ■).
ＫＡＹＡＲＡＤ Ｒ−１２８）４０部、ビス７エ／−
ルＦ型、エポキシ樹脂（シェル化学■製、エピコート８
０７、分子量３４０、エポキシ当量１７ｏ）１モルにア
クリル酸１．９モルを反応して得たエポキシアクリレー
ト７部、１−ヒドロキシシクロへキシルフェニルケトン
５部を混合し、塗料組成物Ｂを調製した。硬化物の特性
を第１表に示す。KAYARAD R-128) 40 parts, screw 7/-
Le F type, epoxy resin (made by Shell Chemical ■, Epicoat 8
Coating composition B was prepared by mixing 7 parts of epoxy acrylate obtained by reacting 1 mole of 07, molecular weight 340, epoxy equivalent weight 17 o) with 1.9 moles of acrylic acid, and 5 parts of 1-hydroxycyclohexyl phenyl ketone. . Table 1 shows the properties of the cured product.
実施例３゜
ポリビニルブチラール樹脂（積木化学工業■製、ニスレ
ックスＢＬ−８） １０ Ｎ、無水フタル酸と２−ヒド
ロキシエチルメタクリレートを等モル反応させて得られ
るカルボキシル基を有するアクリレート１８部、ヘキサ
ヒドロ無水フタル酸と２−ヒドロキシエチルアクリレ−
トラ等モル反応させて得られるカルボキシル基を有する
アクリレート１８部、フェニルグリシジルエーテル１モ
ルにアクリル酸１モルを反応して得たモノアクリレート
２９部、ビフェノールＡ型エポキシ樹脂（シェル化学■
製、エピコート１００４）１モルにアクリル酸１．７モ
ルを反応して得たエポキシアクリレート４部、フェニル
オキシエチルアクリレート（共栄社油脂■製、ＰＯＡ）
２１ 部、１−ヒドロキシシクロへキシルフェニルケ
トン５部を混合し、塗料組成物Ｃを得た。硬化物の特性
を第１表に示す。Example 3 Polyvinyl butyral resin (manufactured by Block Chemical Co., Ltd., Nisrex BL-8) 10 N, 18 parts of acrylate having a carboxyl group obtained by reacting equimolar amounts of phthalic anhydride and 2-hydroxyethyl methacrylate, hexahydro anhydride Phthalic acid and 2-hydroxyethyl acrylate
18 parts of acrylate having a carboxyl group obtained by reacting 1 mole of phenyl glycidyl ether with 1 mole of acrylic acid, 29 parts of monoacrylate obtained by reacting 1 mole of acrylic acid with 1 mole of phenyl glycidyl ether, biphenol A type epoxy resin (Shell Chemical
4 parts of epoxy acrylate obtained by reacting 1.7 mol of acrylic acid with 1 mol of Epicote 1004 (manufactured by Kyoeisha Yushi ■, POA)
21 parts of 1-hydroxycyclohexylphenyl ketone were mixed to obtain a coating composition C. Table 1 shows the properties of the cured product.
比較例１゜
フェニルグリシジルエーテル１モルにアクリル酸１モル
を反応して得たモノアクリレート６５部、２−ヒドロキ
シエチルメタクリロイルホスフェート（日本化薬■製、
ＫＡＹＡＭＡ ＰＭ２）５部、ビスフェノールＡ型エポ
キシ樹脂（シェル化学■製、エピコー） １００４）１
モルにアクリル酸１．９モルを反応して得たエポキシア
クリレート３０部、１−ヒドロキシシクロへキシルフェ
ニルケトン５部を混合し、塗料組成物りを得た。硬化物
の特性を第１表に示す。Comparative Example 1 65 parts of monoacrylate obtained by reacting 1 mole of phenyl glycidyl ether with 1 mole of acrylic acid, 2-hydroxyethyl methacryloyl phosphate (manufactured by Nippon Kayaku ■,
KAYAMA PM2) 5 parts, bisphenol A epoxy resin (Shell Chemical ■, Epicor) 1004) 1
A coating composition was obtained by mixing 30 parts of epoxy acrylate obtained by reacting 1.9 moles of acrylic acid with 5 parts of 1-hydroxycyclohexylphenyl ketone. Table 1 shows the properties of the cured product.
比較例２゜
ポリビニルブチラール樹脂（漬水化学工業■製、ニスレ
ックスＢＬ−８）ｌ ｏ部、フェニルグリシジルエーテ
ル１モルにアクリル酸１モルを反応して得たモノアクリ
レート６０部、ビスフェノールＡ型エポキシ樹脂（シェ
ル化学■製、エビコー） １００４）１モルにアクリル
酸１．９モルを反応して得たエポキシアクリレ−）３０
部。Comparative Example 2 10 parts of polyvinyl butyral resin (manufactured by Tsukisui Kagaku Kogyo ■, Nislex BL-8), 60 parts of monoacrylate obtained by reacting 1 mole of phenyl glycidyl ether with 1 mole of acrylic acid, bisphenol A type epoxy Resin (manufactured by Shell Chemical ■, Ebicor) 1004) Epoxy acrylate obtained by reacting 1 mole of acrylic acid with 1.9 mole) 30
Department.
ｌ−ヒドロキシシクロへキシルフェニルケトン５部を混
合し、塗料組成物Ｅを得た。硬化物の特性を第１表に示
す。Coating composition E was obtained by mixing 5 parts of l-hydroxycyclohexylphenyl ketone. Table 1 shows the properties of the cured product.
第 １ 表
上記第１表において、
塗料組成物を、トルエンで脱脂処理、更にサンドペーパ
ーで表面を磨いた縦２０ｃｒｎ、横７の、肉厚Ｏ０ｌα
の軟質鋼板面にパーコーターを用いて、１５ミクロンの
厚みとなるように塗布した。Table 1 In Table 1 above, the coating composition was degreased with toluene and the surface was polished with sandpaper, measuring 20 crn in length and 7 in width, with a wall thickness of O0lα.
It was applied to the surface of a soft steel plate using a percoater to a thickness of 15 microns.
次いで、この軟質鋼板を高圧水銀灯（２ＫＷ、８０Ｗ／
ｃｒｎ ）下８ｃｒｎの所を、５ｍ７分で走行している
コンベア上にのせて、１回通過したときの塗膜のベタツ
キを調べたところ、ペタツキはなかった。この硬化塗膜
を有する軟質鋼板について次の方法で評価した。Next, this soft steel plate was heated with a high pressure mercury lamp (2KW, 80W/
crn) The bottom 8 crn was placed on a conveyor running at a speed of 5 m and 7 minutes, and the stickiness of the coating film after one pass was examined, and there was no stickiness. The soft steel plate having this hardened coating film was evaluated by the following method.
水酸化ナトリウム溶液を攪拌しながら軟質鋼板を５分間
浸漬し、次いで取り出した後、完全に硬化塗膜が剥離し
ていたもの良好０、塗膜がやや残っていたものやや不良
（ハ）、塗膜か完全に残っていたもの、不良体）とした
。A soft steel plate was immersed in a sodium hydroxide solution for 5 minutes while stirring, and after being taken out, the cured coating film was completely peeled off as 0, and the coating film remained slightly poor (c). If the membrane was completely intact, it was considered defective.
密着性：ｌｌｌ１１１間隔にクロスカットレセロハンテ
ープ剥離テストを行った。Adhesion: A cross-cut cellophane tape peeling test was conducted at 111 intervals.
３回セロテープ剥離テストを行っても、剥離口、目の欠
けも全く生じない０．３回セロテープ剥離テストを行う
と、若干口の欠けがみられる（ハ）、３回セロテープ剥
離テストを行うと、剥離と目の欠けが生じた（×）。Even after performing the cellophane tape peeling test three times, there is no chipping at the opening or the edges.0.When the cellophane tape peeling test is performed three times, there is some chipping at the opening (c). , Peeling and chipping occurred (x).
耐塩水性＝ ６０℃に調整した５％の食塩液中に軟質鋼
板を６時間浸漬後、取り出し、１日室温に放置した後の
軟質鋼板の外観および塗膜の密着性を測定した。なお、
外観は、全く変化がないものを○、わずかな変色または
錆が認められたものをΔ、著しく変色し錆を発生してい
るものをＸとした。Salt water resistance = After immersing a soft steel plate in a 5% saline solution adjusted to 60° C. for 6 hours, it was taken out and left at room temperature for one day, after which the appearance of the soft steel plate and the adhesion of the coating film were measured. In addition,
Regarding the appearance, those with no change at all were rated ○, those with slight discoloration or rust were rated Δ, and those with significant discoloration and rust were rated X.
（発明の効果）
本発明の塗料組成物は、樹脂被膜のアルカリによる脱膜
の速度が速く、密着性、耐塩水性にすぐれており、紫外
線硬化型の一時防錆塗料に適する。(Effects of the Invention) The coating composition of the present invention has a high rate of alkali removal of the resin coating, excellent adhesion and salt water resistance, and is suitable as an ultraviolet curable temporary anticorrosion coating.
Claims (1)
タ）アクリル酸の共重合物又はポリビニルブチラール樹
脂の中より選ばれる樹脂（Ａ）と一般式 ▲数式、化学式、表等があります▼ （式中、Ｒ＿１はＨ又はＣＨ＿３、Ｒ＿２は▲数式、化
学式、表等があります▼又は▲数式、化学式、表等があ
ります▼である。） で表わされる化合物（Ｂ）とフェニルグリシジルエーテ
ルとアクリル酸の反応物（Ｃ）とビスフェノール型エポ
キシ樹脂とアクリル酸の反応物（Ｄ）と光重合開始剤（
Ｅ）を含む事を特徴とする塗料組成物。(1) Resin (A) selected from poly-N-vinylpyrrolidone, a copolymer of styrene and (meth)acrylic acid, or polyvinyl butyral resin and general formula ▲ There are mathematical formulas, chemical formulas, tables, etc. ▼ (in the formula , R_1 is H or CH_3, R_2 is ▲There are mathematical formulas, chemical formulas, tables, etc.▼ or ▲There are mathematical formulas, chemical formulas, tables, etc.▼.) Reaction of compound (B), phenyl glycidyl ether, and acrylic acid (C), a reaction product (D) of bisphenol type epoxy resin and acrylic acid, and a photopolymerization initiator (
A coating composition characterized by containing E).
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13178786A JPS62288667A (en) | 1986-06-09 | 1986-06-09 | Coating compound composition |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| JP13178786A JPS62288667A (en) | 1986-06-09 | 1986-06-09 | Coating compound composition |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| JPS62288667A true JPS62288667A (en) | 1987-12-15 |
Family
ID=15066128
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| JP13178786A Pending JPS62288667A (en) | 1986-06-09 | 1986-06-09 | Coating compound composition |
Country Status (1)
| Country | Link |
|---|---|
| JP (1) | JPS62288667A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01261410A (en) * | 1988-04-13 | 1989-10-18 | Toagosei Chem Ind Co Ltd | Actinic radiation-curable resin composition |
| JPH02153909A (en) * | 1988-12-06 | 1990-06-13 | Nippon Kayaku Co Ltd | Light-polymerizable composition |
| JPH0320315A (en) * | 1989-04-21 | 1991-01-29 | E I Du Pont De Nemours & Co | Donative additives for minimized contraction to photocuring compounds |
| JPH05100423A (en) * | 1991-10-04 | 1993-04-23 | Toagosei Chem Ind Co Ltd | Ultraviolet curing type resin composition |
| JP2009507934A (en) * | 2005-05-27 | 2009-02-26 | ビーエーエスエフ コーティングス アクチェンゲゼルシャフト | COATING MATERIAL, PROCESS FOR PRODUCING THE SAME AND ITS USE FOR PRODUCING ADHESIVE, COLORED AND / OR EFFECTIVE COATING |
| JP2014098088A (en) * | 2012-11-14 | 2014-05-29 | Toagosei Co Ltd | Active energy ray-curable metal anticorrosive coating agent composition |
-
1986
- 1986-06-09 JP JP13178786A patent/JPS62288667A/en active Pending
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH01261410A (en) * | 1988-04-13 | 1989-10-18 | Toagosei Chem Ind Co Ltd | Actinic radiation-curable resin composition |
| JPH02153909A (en) * | 1988-12-06 | 1990-06-13 | Nippon Kayaku Co Ltd | Light-polymerizable composition |
| JPH0320315A (en) * | 1989-04-21 | 1991-01-29 | E I Du Pont De Nemours & Co | Donative additives for minimized contraction to photocuring compounds |
| JPH05100423A (en) * | 1991-10-04 | 1993-04-23 | Toagosei Chem Ind Co Ltd | Ultraviolet curing type resin composition |
| JP2009507934A (en) * | 2005-05-27 | 2009-02-26 | ビーエーエスエフ コーティングス アクチェンゲゼルシャフト | COATING MATERIAL, PROCESS FOR PRODUCING THE SAME AND ITS USE FOR PRODUCING ADHESIVE, COLORED AND / OR EFFECTIVE COATING |
| JP2014098088A (en) * | 2012-11-14 | 2014-05-29 | Toagosei Co Ltd | Active energy ray-curable metal anticorrosive coating agent composition |
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