WO2006100778A1 - エポキシ塗料組成物 - Google Patents
エポキシ塗料組成物 Download PDFInfo
- Publication number
- WO2006100778A1 WO2006100778A1 PCT/JP2005/005385 JP2005005385W WO2006100778A1 WO 2006100778 A1 WO2006100778 A1 WO 2006100778A1 JP 2005005385 W JP2005005385 W JP 2005005385W WO 2006100778 A1 WO2006100778 A1 WO 2006100778A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- epoxy
- coating composition
- resin
- paint
- fraction
- Prior art date
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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
Definitions
- the present invention relates to a non-tar type epoxy coating composition, and more specifically, improves workability during coating, and is excellent in anticorrosion, water resistance, adhesion, and overcoatability.
- the present invention relates to an epoxy paint thread and a composition suitable for coating.
- Patent Document 1 In recent years, in order to improve the compatibility with epoxy resin and hardener, hydrocarbon resin containing hydroxyl group obtained by polymerization of unsaturated fraction obtained by cracking petroleum and phenols has been used.
- Epoxy paint compositions are disclosed in Patent Document 1, Patent Document 2, Patent Document 3, Patent Document 4, Patent Document 5, and the like.
- Patent Document 6 discloses that 60-90% of a high-purity indene fraction obtained by distillation of an aromatic fraction of 140-220 ° C obtained by petroleum cracking is polymerized in the presence of phenols. Examples using the hydroxyl-containing hydrocarbon resin produced are also mentioned.
- Patent Document 1 JP-A-53-141361
- Patent Document 2 JP 54-43259 A Patent Document 3: Japanese Patent Laid-Open No. 54-46258
- Patent Document 4 JP-A-61-203111
- Patent Document 5 JP-A-9-263713
- Patent Document 6 Japanese Patent Laid-Open No. 11 323247
- the problem to be solved by the present invention is to provide an epoxy coating composition excellent in environmental safety, workability during application, anticorrosion, water resistance, adhesion and overcoatability. That's it.
- a modified hydrocarbon resin containing a hydroxyl group and a force lpoxyl group in the molecule is excellent in compatibility with an epoxy resin and a curing agent.
- the epoxy coating composition containing the modified hydrocarbon resin has a light color that does not cause environmental safety problems, wettability with pigments, anticorrosion, water resistance, overcoatability and adhesion of the coating film. The present invention has been found.
- the present invention is an epoxy coating composition containing an epoxy resin (A), a curing agent (B), and a modified hydrocarbon resin (C) having a hydroxyl group and a force lpoxyl group in the molecule.
- An epoxy coating composition in which the amount of the modified hydrocarbon resin (C) is 10 to 500 parts by mass with respect to 100 parts by mass of the epoxy resin (A) solid content is provided.
- the epoxy coating composition of the present invention is excellent in workability at the time of application, corrosion resistance, water resistance, adhesion, recoating property, and the like, and therefore is used as a coating for ships, buildings, bridges and other general structures. Can be used.
- the modified hydrocarbon resin (C) having a hydroxyl group and a carboxyl group in the molecule is excellent in compatibility with an epoxy resin and a curing agent, and an epoxy coating composition containing the modified hydrocarbon resin (C)
- the product is also excellent in workability during application, water resistance, corrosion resistance, adhesion and overcoatability. In addition, it does not contain any tar, so there are no environmental problems and light colors. Because it can form coating films, it is mainly useful as an anticorrosion paint for ships and general structures.
- Various performances of the epoxy coating composition according to the present invention can be obtained by using a modified hydrocarbon resin (C) having both a hydroxyl group and a carboxyl group in the molecule, which is mainly hydrophilic. This is thought to be due to the improved compatibility of the epoxy resin and the curing agent and the wettability of the pigment by the presence of hydroxyl groups and carboxyl groups having different degrees of properties. Hydroxyl groups are thought to be important for improving compatibility, but on the other hand, if there are too many hydroxyl groups, the hydrophilicity increases, resulting in a negative effect on the water resistance and anticorrosion properties of the paint, and further the adhesion. Leading to a decline.
- the epoxy coating composition of the present invention contains an epoxy resin (A), a curing agent (B), and a modified hydrocarbon resin (C) having a hydroxyl group and a carboxyl group in the molecule.
- the epoxy resin (A) used in the epoxy coating composition of the present invention has at least two epoxy groups per molecule, and has an epoxy equivalent of 150-600, more preferably 180. — 500.
- examples of such resins include bisphenol A type epoxy resins, aliphatic type epoxy resins, glycidyl ester type epoxy resins, glycidylamine type epoxy resins, phenol novolac type epoxy resins, and crezo resins.
- Conventionally known ones such as an epoxy resin and a dimer acid-modified epoxy resin can be used, and these can be used alone or in combination of two or more.
- the curing agent (B) used in the epoxy coating composition of the present invention a known curing agent for epoxy resin can be used.
- various aliphatic or aromatic amines, polyamide amide resins, acid anhydrides, phenol resins, polyisocyanates and the like are exemplified. These can be used alone or in combination.
- amine-based curing agents such as meta-xylene diamine and isophorone diamine.
- aliphatic polyamines such as amine, diethylenetriamine, triethylenetetraamine, diaminodiphenol-methane, aromatic polyamines, epoxy resin adducts of these polyamines, polyamidoamines, and polyamide resins. These can be used alone or in combination of two or more.
- the proportions of the epoxy resin (A) and the curing agent (B) can be appropriately selected depending on the types of both components. In general, a range force of 10-500 parts by weight of curing agent per 100 parts by weight of epoxy resin can also be selected.
- the equivalent ratio usually expressed as (active hydrogen equivalent of curing agent (B)) Z (epoxy equivalent in epoxy resin (A)) is 0.5. — It is appropriate to select a value in the range of 1.0.
- the modified hydrocarbon resin (C) having a hydroxyl group and a carboxyl group in the molecule used in the epoxy coating composition of the present invention has 0.1 to 2.0 phenolic hydroxyl groups in one molecule. It is preferable to contain 0.2-1.0 more preferably.
- the acid value of the modified hydrocarbon resin (C) is preferably 2-50 in terms of providing a good balance of workability, adhesion, water resistance, anticorrosion, and overcoatability during coating! / ,.
- the soft hydrocarbon point of the modified hydrocarbon resin (C) is that the viscosity of the paint is appropriate, and the resin does not bleed on the surface of the coating film and remains sticky. — 150 ° C is preferred.
- the modified hydrocarbon resin (C) preferably has a number average molecular weight range of 400-2500.
- the amount of the modified hydrocarbon resin (C) used is in the range of 10 to 500 parts by mass with respect to 100 parts by mass of the epoxy resin (A). If the blending amount is less than 10 parts by mass, the resulting coating film has high hardness and poor impact resistance. On the other hand, if the amount exceeds 500 parts by mass, the softness of the coating film increases, but the water resistance is inferior.
- the method for producing the modified hydrocarbon resin (C) used in the epoxy coating composition of the present invention is not particularly limited as long as the above-described modified hydrocarbon resin (C) can be produced. However, it can be produced with reference to a known method, for example.
- a specific example of the production method is as follows: a hydrocarbon mixture containing monoolefins and compounds having a conjugated double bond and a monomer mixture containing phenols as a main component, and a polymer obtained It can be produced by reacting with an organic unsaturated acid.
- monoolefins include styrene, ⁇ -methylstyrene, and ⁇ -methylstyrene. And butyltoluene, indene and methylindene.
- Specific examples of the compound having a conjugated double bond include isoprene, piperylene and cyclopentagen.
- phenols contained in a monomer mixture containing phenols as a main component include monovalent phenols such as phenol, o-cresol, m-cresol, p-cresol, butylphenol and xylenol. And alkyl-substituted phenols such as norphenol and dinourphenol. Also, two or more of the above-mentioned phenols can be mixed and used.
- organic unsaturated acid examples include ⁇ , ⁇ unsaturated carboxylic acids such as acrylic acid, methacrylic acid, crotonic acid, itaconic acid, maleic anhydride and fumaric acid.
- the reaction conditions for polymerizing a monomer mixture containing a hydrocarbon mixture containing monoolefins and compounds having a conjugated double bond and phenols as main components can be produced according to a known method. Specifically, polymerization is performed using a Friedel-Crafts-type catalyst such as an aluminum halide such as anhydrous trisalt-aluminum or a complex thereof, boron trifluoride or a complex thereof, or a tin halide such as tin tetrachloride. It can be performed.
- a Friedel-Crafts-type catalyst such as an aluminum halide such as anhydrous trisalt-aluminum or a complex thereof, boron trifluoride or a complex thereof, or a tin halide such as tin tetrachloride. It can be performed.
- reaction conditions for producing the modified hydrocarbon resin (C) by adding an organic unsaturated acid to the obtained polymer can be carried out by heating in a conventional manner.
- the amount of unsaturated acid used depends on the content of monoolefins and compounds having conjugated double bonds contained in the hydrocarbon mixture. Since the amount of acid fluctuates, it cannot be generally determined. For this reason, the amount of each raw material used is such that the resulting modified hydrocarbon resin (C) has a good balance of compatibility with the epoxy resin and the curing agent, and the workability and adhesion during application as a coating composition.
- the range is adjusted as appropriate together with the polymerization conditions and the like so that the water resistance, corrosion resistance, overcoatability, and the like, for example, the number and acid value of the phenolic hydroxyl groups described above are obtained.
- Hydrocarbon mixture containing monoolefins and compounds having conjugated double bonds Specific examples thereof include a fraction containing unsaturated hydrocarbons obtained by pyrolysis of petroleum.
- fractions containing unsaturated hydrocarbons obtained by petroleum pyrolysis include monoolefin fin fractions (C9 fraction) containing aromatics with boiling points of 140-200 ° C and boiling points of 20 — Hydrocarbon mixtures consisting of fractions containing aliphatic conjugated double bonds at 80 ° C (C5 fractions).
- the C9 fraction obtained as a by-product contains styrene, ⁇ -methylstyrene, ⁇ -methylstyrene, butrruen, indene, methyl as reaction components. Includes monoolefins such as inden.
- the reaction component of the C5 fraction includes conjugated double bond monomers such as isoprene, piperylene, and cyclopentagen.
- a polymer obtained by polymerizing only a C9 fraction with a monomer mixture containing phenols as a main component has an unsaturated bond in the molecule sufficient to advance the reaction with an organic unsaturated acid. Because of this, it is difficult to introduce carboxyl groups by adding organic unsaturated acids.
- a liquid modifier for example, a reactive resin such as xylene resin, toluene resin, butyldaricidyl ether, These additives may be added in an amount of 50 parts by mass or less with respect to 100 parts by mass of the epoxy resin.
- aromatics such as water resistant maintenance are preferably used.
- pigments such as extender pigments and colored pigments, reactive diluents, organic solvents, anti-settling agents, anti-sagging agents, wetting agents, reaction accelerators
- Ordinary paint additives such as an agent, an adhesion-imparting agent, and a dehydrating agent may be appropriately blended.
- the epoxy coating composition of the present invention is preferably used as a two-pack type coating comprising a main component containing an epoxy resin and a curing agent, preferably an amine curing agent.
- the two-part coating The material is usually applied to a protective coating such as a zinc primer. That is, first, shot blasting is applied to the steel sheet to remove the mill scale, and an inorganic zinc shot primer such as ethyl silicate is applied, and then the coating composition of the present invention is applied.
- Primers are not limited to zinc silicate, and various primers can be used.
- a steel plate without a primer can be painted, and a sufficient anticorrosion effect can be obtained.
- a coating method conventionally known methods such as air spray, airless spray, brush coating, and roller can be adopted, and the coating composition can be applied to a dry film thickness of 150 to 500 ⁇ m. it can.
- a part and% show a mass part and mass%, respectively.
- an aromatic C9 fraction having a boiling point of 140-200 ° C (containing 55% monoolefin) obtained by pyrolysis of petroleum was added to 100 parts of an aliphatic C5 fraction having a boiling point of 20-80 ° C. (Contained 30% conjugated double bond)
- the catalyst was separated with a caustic soda solution, washed with water, unreacted oil and low polymer were removed by distillation under reduced pressure, and 60 parts of a hydroxyl group-containing unsaturated hydrocarbon resin containing 0.6 hydroxyl groups in the molecule was removed. Obtained.
- Table 1 shows the properties of the obtained rosin.
- a modified hydrocarbon resin (C) was produced according to the formulation shown in Table 1 under the same conditions as in Example 1. Their properties are shown in Table 1.
- the first stage reaction was polymerized under the same conditions as in Example 1 except that 100 parts of C9 fraction and 8 parts of phenol were used, and the hydroxyl group-containing hydrocarbon containing no structural unit derived from C5 fraction was used. A fat was obtained. The addition reaction of maleic anhydride by the next second stage reaction was powerful. Table 1 shows the properties of the obtained rosin.
- the first stage reaction was polymerized under the same conditions as in Example 1 except that only 100 parts of the C9 fraction was used, and it did not have C5 fraction and phenol-derived structural units, and had no hydroxyl group. A hydrocarbon resin was obtained.
- Example 2 In the next second stage reaction, 0.4 part of maleic anhydride was added to 40 parts of this resin and an addition reaction of maleic anhydride was attempted in the same manner as in Example 1. However, unlike Example 1, the acid value of the obtained rosin was as low as 1.0. This is because the resin obtained in the first stage reaction does not have an unsaturated bond sufficient to proceed with the addition reaction, and therefore the reactivity is inferior. Inferred.
- Table 1 shows the properties of the obtained rosin.
- Table 1 shows the properties of the obtained rosin.
- Nikanol L xylene resin (Mitsubishi Gas Chemical Co., Ltd.)
- test piece is applied to a degreased polished mild steel plate (200 X 100 X 0.6 mm) with an applicator to a film thickness of about 250 m and dried for 7 days in an atmosphere of 20 ° C X 65% RH. used.
- test piece is applied to a defatted polished mild steel plate with a silicate primer thickness of about 20 ⁇ m, dried for one day, and then applied to an about 250 ⁇ m coating film with an applicator (7 ° C at 65 ° C at 65 ° C). Specimens dried for days were used.)
- ⁇ Uniform coating is extended and work is good
- ⁇ Uniform coating is extended and workability is slightly inferior * 15) Applicable to a degreased polished mild steel plate with an applicator so that it is about 200 ⁇ m, 20 ° CX 65% RH atmosphere Then, after drying for 7 days, a second coating (200 ⁇ m) was applied to the top surface of the coating once and dried for 3 days. This was used as a test piece. Immerse the test piece in seawater for 30 days, and evaluate delamination by peeling test with knife (5mm width).
- the epoxy coating composition of the present invention is excellent in water resistance, adhesion, anticorrosion, workability during coating, and overcoatability. .
- it since it does not contain any tar, it can be used as an anticorrosion paint for ships and general structures because it can form a light-colored film with no environmental problems.
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- 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
Description
Claims
Priority Applications (4)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
CN2005800488014A CN101133133B (zh) | 2005-03-24 | 2005-03-24 | 环氧涂料组合物 |
KR1020077018307A KR101194454B1 (ko) | 2005-03-24 | 2005-03-24 | 에폭시 도료 조성물 |
PCT/JP2005/005385 WO2006100778A1 (ja) | 2005-03-24 | 2005-03-24 | エポキシ塗料組成物 |
HK08109486.4A HK1118306A1 (en) | 2005-03-24 | 2008-08-26 | Epoxy coating composition |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
PCT/JP2005/005385 WO2006100778A1 (ja) | 2005-03-24 | 2005-03-24 | エポキシ塗料組成物 |
Publications (1)
Publication Number | Publication Date |
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WO2006100778A1 true WO2006100778A1 (ja) | 2006-09-28 |
Family
ID=37023475
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
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PCT/JP2005/005385 WO2006100778A1 (ja) | 2005-03-24 | 2005-03-24 | エポキシ塗料組成物 |
Country Status (4)
Country | Link |
---|---|
KR (1) | KR101194454B1 (ja) |
CN (1) | CN101133133B (ja) |
HK (1) | HK1118306A1 (ja) |
WO (1) | WO2006100778A1 (ja) |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012256872A (ja) * | 2011-05-12 | 2012-12-27 | Rohm & Haas Electronic Materials Llc | 誘電体への金属の接着促進 |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
KR100934637B1 (ko) * | 2009-04-07 | 2009-12-31 | 동해케미칼공업주식회사 | 소수성을 부여한 고속건조형 수성 에폭시 도료의 조성물 |
Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002348515A (ja) * | 2001-05-28 | 2002-12-04 | Arakawa Chem Ind Co Ltd | 印刷インキ用バインダーおよび当該印刷インキ用バインダーを含有してなる印刷インキ、コーティング剤ならびに塗料用組成物 |
JP2003171611A (ja) * | 2001-12-07 | 2003-06-20 | Chugoku Marine Paints Ltd | 高伸び率を有する塗膜を形成可能なエポキシ樹脂組成物、防食塗料組成物、その塗膜、その塗膜で被覆された基材、並びに基材の防食方法 |
JP2005113103A (ja) * | 2003-10-06 | 2005-04-28 | Toho Chem Ind Co Ltd | エポキシ塗料組成物 |
Family Cites Families (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN1147545C (zh) * | 1996-03-28 | 2004-04-28 | 关西涂料株式会社 | 防腐蚀涂料组合物 |
JP4150104B2 (ja) * | 1998-05-13 | 2008-09-17 | 新日本石油株式会社 | 防食塗料組成物 |
-
2005
- 2005-03-24 WO PCT/JP2005/005385 patent/WO2006100778A1/ja not_active Application Discontinuation
- 2005-03-24 CN CN2005800488014A patent/CN101133133B/zh not_active Expired - Fee Related
- 2005-03-24 KR KR1020077018307A patent/KR101194454B1/ko not_active IP Right Cessation
-
2008
- 2008-08-26 HK HK08109486.4A patent/HK1118306A1/xx not_active IP Right Cessation
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2002348515A (ja) * | 2001-05-28 | 2002-12-04 | Arakawa Chem Ind Co Ltd | 印刷インキ用バインダーおよび当該印刷インキ用バインダーを含有してなる印刷インキ、コーティング剤ならびに塗料用組成物 |
JP2003171611A (ja) * | 2001-12-07 | 2003-06-20 | Chugoku Marine Paints Ltd | 高伸び率を有する塗膜を形成可能なエポキシ樹脂組成物、防食塗料組成物、その塗膜、その塗膜で被覆された基材、並びに基材の防食方法 |
JP2005113103A (ja) * | 2003-10-06 | 2005-04-28 | Toho Chem Ind Co Ltd | エポキシ塗料組成物 |
Cited By (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JP2012256872A (ja) * | 2011-05-12 | 2012-12-27 | Rohm & Haas Electronic Materials Llc | 誘電体への金属の接着促進 |
Also Published As
Publication number | Publication date |
---|---|
HK1118306A1 (en) | 2009-02-06 |
CN101133133B (zh) | 2012-06-27 |
CN101133133A (zh) | 2008-02-27 |
KR101194454B1 (ko) | 2012-10-24 |
KR20070118592A (ko) | 2007-12-17 |
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