WO1999058618A1 - Composition de revetement pour la protection contre la corrosion - Google Patents

Composition de revetement pour la protection contre la corrosion Download PDF

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Publication number
WO1999058618A1
WO1999058618A1 PCT/JP1999/002489 JP9902489W WO9958618A1 WO 1999058618 A1 WO1999058618 A1 WO 1999058618A1 JP 9902489 W JP9902489 W JP 9902489W WO 9958618 A1 WO9958618 A1 WO 9958618A1
Authority
WO
WIPO (PCT)
Prior art keywords
resin
weight
parts
content
curing agent
Prior art date
Application number
PCT/JP1999/002489
Other languages
English (en)
Japanese (ja)
Inventor
Hisatake Sato
Original Assignee
Nippon Petrochemicals Company, Limited
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by Nippon Petrochemicals Company, Limited filed Critical Nippon Petrochemicals Company, Limited
Priority to KR1019997012470A priority Critical patent/KR100577920B1/ko
Publication of WO1999058618A1 publication Critical patent/WO1999058618A1/fr
Priority to FI20000039A priority patent/FI121995B/fi

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L57/00—Compositions of unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C08L57/02—Copolymers of mineral oil hydrocarbons
    • 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
    • C09D157/00—Coating compositions based on unspecified polymers obtained by reactions only involving carbon-to-carbon unsaturated bonds
    • C09D157/02—Copolymers of mineral oil hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of 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
    • C09D5/08—Anti-corrosive paints
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L2314/00—Polymer mixtures characterised by way of preparation

Definitions

  • the present invention relates to an anticorrosion paint composition which is an alternative paint to a tar-based epoxy paint, and which is particularly useful for painting in a portion in contact with seawater, for example, in a ballast tank of a ship.
  • 9-263713 discloses a divinyltoluene-indene copolymer having a hydroxyl content in one molecule of 1 to: L. 1 mol (softening point 100 °) in Examples.
  • An epoxy resin-based anticorrosive paint using C) is disclosed.
  • the epoxy coatings described in the above publications have a problem in compatibility between the epoxy resin, the curing agent, particularly the cured resin composed of the amine curing agent, and the petroleum-based resin. It is not sufficient for painting areas that come into direct contact with seawater, for example, in ballast tanks on ships. Disclosure of the invention
  • the inventors of the present invention have conducted intensive studies to solve the above-mentioned problems, and as a result, have used a resin starting from an aromatic fraction having a specified indene content and relatively reduced the content of phenolic hydroxyl groups.
  • resin By using resin, it has excellent compatibility with epoxy resins and hardeners, especially amine-based hardeners. As a result, there is no problem in hygiene, corrosion resistance, water resistance, adhesion, etc.
  • the present inventors have found that an anticorrosive coating composition capable of forming a film can be obtained, and have reached the present invention.
  • the first aspect of the present invention is that the epoxy resin (A), the curing agent, preferably the amine-based curing agent (B), and the cracked oil obtained by thermal cracking of petroleums are mainly 140 to 220 ° C. It is obtained by polymerizing a cracked oil fraction with an indene content of 60 to 90% by weight obtained by distillation from a fraction containing components in the boiling range of C with a Friedel-Crafts catalyst in the presence of phenols.
  • An aromatic petroleum resin (C) containing at least 0.1 and less than 1.0 phenolic hydroxyl groups per molecule, wherein the aromatic petroleum resin (C) is added to 100 parts by weight of the epoxy resin. 1 to 500 parts by weight.
  • the second aspect of the present invention relates to the anticorrosion paint composition according to the first aspect of the present invention, wherein the conjugated gen content of the cracked oil fraction is 5% by weight or less.
  • the epoxy resin (A) used in the present invention has at least two or more epoxy groups in one molecule, and suitably has an epoxy equivalent of 150 to 600, preferably 180. 0 to 500.
  • epoxy resins include bisphenol epoxy resins, aliphatic epoxy resins, glycidyl ester epoxy resins, glycidylamine epoxy resins, phenol nopolak epoxy resins, cresol epoxy resins, and dimers.
  • Conventionally known ones such as an acid-modified epoxy resin may be mentioned, and these may be used alone or in combination of two or more.
  • the curing agent (B) used in the present invention a conventionally known curing agent for an epoxy resin is used.
  • various aliphatic or aromatic amines, polyamide resin, acid anhydrides, phenolic resins, polyisocyanates and the like are exemplified. These are 1 They can be used alone or as a mixture of two or more.
  • amine-based curing agents for example, aliphatic polyamines such as metaxylenediamine, holondiamine, diethylenetriamine, triethylenetetramine, diaminodiphenylmethane, alicyclic polyamines, aromatic polyamines, and these polyamines.
  • Epoxy resin adducts, polyamidoamines, and polyamide resins can be used alone or in combination of two or more.
  • the mixing ratio of the epoxy resin (A) and the curing agent (B) can be appropriately selected depending on the types of both components. Generally, it is selected from the range of 1 to 200 parts by weight of hardener per 100 parts by weight of epoxy resin. When a preferred amine-based curing agent is used as the curing agent (B), the active hydrogen equivalent in (B) and the equivalent ratio of epoxy equivalent in (A) are usually 0.5 to 1.0. It is appropriate to select a value within the range.
  • the aromatic petroleum resin (C) used in the present invention is a petroleum resin containing a phenolic hydroxyl group, which is solid at room temperature and has a softening point of 50 to 150 ° C., preferably Use the one of 80 to 110 ° C.
  • the cracking oil mainly produced by cracking of hydrocarbons, such as naphtha and butane, by-produced to produce ethylene, propylene, etc.
  • a fraction containing components in the range of 140 to 220 ° C is used as a raw material.
  • Such fractions include styrene, ⁇ - or i3-methylstyrene, vinyltoluene, indene, methylindene, unsaturated components such as dicyclopentadiene, dimethylcyclopentene, and ethylethyl, trimethylbenzene, Includes saturated components such as indane, methyl indane, and naphthalene.
  • the system produced by the dicyclobe Is also included.
  • a fraction obtained by distillation of the cracked oil and having an indene content of 60 to 90% by weight is used as a raw material.
  • the indene content (% by weight) is defined as (total amount of alkyl indene such as indene and methyl indene Z content of all unsaturated components in cracked oil fraction) X 100 Is defined.
  • a fraction having a conjugated diene content of 5% by weight or less such as cyclopentadiene or methylcyclopentadiene, is used.
  • the content of the conjugated gen is defined as (total amount of conjugated gens Z total content of unsaturated components in the cracked oil fraction) X 100.
  • the above components can be easily analyzed by a known gas chromatography method.
  • the cracked oil fraction having the above composition can be easily obtained by appropriately treating cracked oil produced as a by-product of thermal cracking with a known distillation method.
  • the raw material resin of the present invention comprises 1.0 to 10.0 parts by weight of phenols in 100 parts by weight of the cracked oil fraction and 0.01 to 3 parts by weight based on the cracked oil fraction. % Of Freedell-Crafts catalyst and polymerized in the range of 10 to 10 ° C.
  • phenols examples include, in addition to phenols, alkyl-substituted phenols such as cresol, xylenol, tert-butylphenol, and nonylphenol. These can be used in combination. Preferred is phenol. Phenols can be present in the reaction system as a component of the Friedel Crafts catalyst described below, but usually a predetermined amount of phenol is supplied to the reaction system separately from the catalyst. Many.
  • a metal halide preferably boron trifluoride, or a complex thereof with an oxygen-containing compound such as phenol, ethyl ether, butyl ether, butyl alcohol, or methyl alcohol is used.
  • the polymerization time can be selected from the range of 0.5 to 10 hours in the case of a batch system.
  • a resin having a predetermined softening point can be obtained by charging a predetermined amount of the cracked oil fraction, phenols, Friedel-Crafts catalyst, and the like and polymerizing by a known method. After the polymerization, the catalyst is appropriately deactivated using an alkali or the like, and then the unreacted oil or low polymer is appropriately separated and removed by distillation or the like to obtain the desired resin.
  • the petroleum resin (C) used in the coating composition of the present invention contains at least 0.1 and less than 1.0 phenolic hydroxyl groups in one molecule of the petroleum resin. Preferably, it is 0.5 to 0.9.
  • a resin having an amount of phenolic hydroxyl groups within the above range can be obtained by appropriately adjusting the amount of each raw material, the polymerization conditions, and the like.
  • phenolic hydroxyl groups are present in one molecule of the petroleum resin (C) used in the present invention, it is not preferable as a resin for anticorrosion paint. On the other hand, if it is less than 0.1, the compatibility with the epoxy resin is lowered, which is not preferable.
  • the amount of the phenolic hydroxyl group present in the obtained resin can be measured, for example, by the method described in IE. III. C. Anal. Ed. (1945) p. 394.
  • the softening point of the resin (C) is in the range of 50 to 150 ° (preferably, 80 to 110 ° C as described above. If the softening point is less than 50 ° C, The water resistance of the anti-corrosion coating film is low, and the resin component may be bled on the surface of the coating film and the tackiness may remain.On the other hand, when the temperature exceeds 150 ° C, the viscosity of the coating material increases and the workability decreases.
  • the molecular weight of the resin (C) used in the present invention is in the range of 500 to 300 as a number average molecular weight.
  • the petroleum resin (C) having a phenolic hydroxyl group is added in an amount of 1 to 500 parts by weight, preferably 10 to 100 parts by weight, based on 100 parts by weight of the epoxy resin (A). 300 parts by weight are blended. If the amount is less than 1 part by weight, sufficient water resistance cannot be obtained in the obtained composition, while if it exceeds 500 parts by weight, the coating film becomes brittle and good physical properties cannot be obtained. Not preferred.
  • the anticorrosive coating composition of the present invention may further contain other liquid modifiers such as xylene resin and toluene resin, and reactive diluents such as epoxy compounds such as butyldaricidyl ether to impart flexibility. May be added in a range of 50 parts by weight or less based on 100 parts by weight of the solid content of the cured resin. Of these, aromatic ones are preferably used from the viewpoint of maintaining water resistance.
  • the composition of the present invention may further include, if necessary, an extender pigment> pigments such as an anti-pigment pigment and a color pigment; a reactive diluent; an organic solvent, an anti-settling agent, a sunscreen agent, a wetting agent, and a reaction promoting agent.
  • an extender pigment> pigments such as an anti-pigment pigment and a color pigment
  • a reactive diluent such as an organic solvent, an anti-settling agent, a sunscreen agent, a wetting agent, and a reaction promoting agent.
  • Ordinary paint additives such as a promoter, an adhesion-imparting agent, and a dehydrating agent may be appropriately compounded.
  • the composition of the present invention is a two-pack type paint comprising a main agent containing an epoxy resin and a curing agent, preferably an amine-based curing agent, and is usually applied on a primary anti-reflective coating film such as a zinc primer.
  • a steel plate is first subjected to shot blasting to remove mill scale, and an inorganic zinc shop primer such as ethyl silicate is applied, and then the coating composition of the present invention is applied.
  • the primer is not limited to zinc silicate and the like, and various primers can be used.
  • even a steel plate without a primer can be coated, and a sufficient anticorrosion effect can be obtained.
  • a coating method a conventionally known method such as air spraying, airless spraying, brush coating, and mouth washing can be adopted.
  • the above coating composition is dried to have a dry film thickness of 150 to 500 m. Can be applied.
  • Parts and % indicate “parts by weight” and “% by weight”, respectively.
  • the total unsaturated component content is 51%
  • the indene content is 70%
  • a cracked oil fraction adjusted to 0.5% of synergist content was obtained.
  • the softening point of the obtained resin was 103 ° C., and as a result of analysis, it was confirmed that the molecule had 0.8 phenolic hydroxyl groups per molecule.
  • a cracked oil fraction having an indene content of 20% and a conjugated gen content of 6% was obtained in the same manner as in the above Production Example.
  • compositions were produced in the same manner with the formulations shown in Table 1.
  • the petroleum resin (B) of the comparative production example was used.
  • Table 1 shows the results.
  • Hydrocarbon plasticizer trade name "Hisol S AS LH”, manufactured by Nippon Petrochemical Co., Ltd.
  • each sample was coated on a degreased polished mild steel plate (200 x 100 x 0.6 mm) by an applicator to a dry film thickness of about 250 m, and then dried under an atmosphere of 20 ° C and 65% RH. After drying for 7 days, each test coated plate was prepared.
  • the coated plate was subjected to a DuPont impact test specified in JIS K5400-1990 in an atmosphere of 20 ° C.
  • the degreased polished mild steel sheet was coated with a silica zinc primer to a dry film thickness of about 25 m and dried for one day. On this, each sample was applied to a dry film thickness of about 250 m by means of apriquet overnight and dried for 7 days in an atmosphere of 20 ° C and 65% RH to obtain each test piece.
  • test pieces were subjected to a cold-heat repetition test according to JIS K5400-1990.
  • test piece similar to that prepared in the above (2) cold / heat repetition resistance test was immersed in 50 seawater for 6 months, and then the state of the coated surface was visually evaluated.
  • the criteria for evaluation are as follows.
  • the anticorrosion coating composition of the present invention uses a petroleum resin containing a hydroxyl group-containing hydroxyl group having a specific content of an indene, the compatibility between the epoxy resin and the curing agent, particularly the amine-based curing agent, and the oil resin is improved. It is good, has no hygiene problems, is excellent in corrosion resistance, water resistance, adhesion, etc., and can form a light-colored coating film.It is very useful as an anticorrosion paint for ships and structures. is there.

Abstract

L'invention concerne une composition de revêtement époxydique pour la protection contre la corrosion, qui est constituée d'une résine époxy (A), d'un agent durcissant (B), de préférence un agent durcissant aminé, et d'une résine de pétrole aromatique (C) préparée par polymérisation d'une fraction de distillé pétrolier contenant 60 à 90 % en poids d'indènes, en présence de phénols, et comprenant des groupes hydroxyles phénoliques à raison de moins de 1,0 par molécule. La teneur en résine de pétrole est égale à 1 à 500 parties en poids par rapport à 100 parties en poids de la résine époxy. Ladite composition de revêtement époxydique ne contient pas de goudron et peut donc être appliquée sur une pièce en contact avec l'eau de mer.
PCT/JP1999/002489 1998-05-13 1999-05-13 Composition de revetement pour la protection contre la corrosion WO1999058618A1 (fr)

Priority Applications (2)

Application Number Priority Date Filing Date Title
KR1019997012470A KR100577920B1 (ko) 1998-05-13 1999-05-13 방식도료 조성물
FI20000039A FI121995B (fi) 1998-05-13 2000-01-10 Korroosiosuojaukseen tarkoitettu päällystyskoostumus

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP10/148353 1998-05-13
JP14835398A JP4150104B2 (ja) 1998-05-13 1998-05-13 防食塗料組成物

Publications (1)

Publication Number Publication Date
WO1999058618A1 true WO1999058618A1 (fr) 1999-11-18

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Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP1999/002489 WO1999058618A1 (fr) 1998-05-13 1999-05-13 Composition de revetement pour la protection contre la corrosion

Country Status (5)

Country Link
JP (1) JP4150104B2 (fr)
KR (1) KR100577920B1 (fr)
CN (1) CN1162486C (fr)
FI (1) FI121995B (fr)
WO (1) WO1999058618A1 (fr)

Families Citing this family (13)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR101194454B1 (ko) * 2005-03-24 2012-10-24 도호 가가꾸 고오교 가부시키가이샤 에폭시 도료 조성물
WO2007088889A1 (fr) 2006-02-03 2007-08-09 Asahi Kasei Chemicals Corporation Agent de durcissement de type microcapsule pour resine epoxy, composition d'agent de durcissement de type melange maitre pour resine epoxy, composition de resine epoxy de type en une partie et article traite
JP5255192B2 (ja) * 2006-08-21 2013-08-07 中国塗料株式会社 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
KR101423170B1 (ko) * 2006-10-04 2014-07-25 신닛테츠 수미킨 가가쿠 가부시키가이샤 에폭시 수지, 페놀 수지, 그들의 제조방법, 에폭시 수지 조성물 및 경화물
CN101134867B (zh) * 2007-09-28 2012-05-23 中山大桥化工有限公司 船舶压载舱涂料组合物
CN101880505B (zh) * 2010-07-06 2012-07-18 庞贝捷(涂料)昆山有限公司 厚膜型防锈涂料及其制备方法
EP2881414B1 (fr) 2012-07-31 2018-07-11 Asahi Kasei Kabushiki Kaisha Composition de résine époxy et article durci
KR101775613B1 (ko) * 2014-09-16 2017-09-07 주식회사 메디바이오랩 망고스틴 추출물 또는 알파, 감마 망고스틴을 유효성분으로 포함하는 치주질환 예방 또는 개선용 조성물
JP6712402B2 (ja) 2015-11-13 2020-06-24 味の素株式会社 被覆粒子
CN106349871A (zh) * 2016-08-26 2017-01-25 江苏华夏制漆科技有限公司 一种水性环氧快干防腐涂料及其制备方法
CN114752039A (zh) 2017-03-17 2022-07-15 旭化成株式会社 热固性树脂组合物
WO2019139112A1 (fr) 2018-01-12 2019-07-18 味の素株式会社 Particules enrobées
CN111117418A (zh) * 2018-11-01 2020-05-08 庞贝捷涂料（昆山）有限公司 防腐涂料组合物

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JPS53125461A (en) * 1977-04-11 1978-11-01 Nippon Oil Co Ltd Epoxy resin composition
JPS54131660A (en) * 1978-04-03 1979-10-12 Mitsui Petrochem Ind Ltd Epoxy resin composition
JPH0286644A (ja) * 1988-09-22 1990-03-27 Nippon Steel Chem Co Ltd クマロンインデン樹脂乳化組成物および接着剤
JPH04173889A (ja) * 1990-11-06 1992-06-22 Tosoh Corp ホットメルト接着剤
JPH05105858A (ja) * 1991-10-17 1993-04-27 Nippon Steel Chem Co Ltd ホツトメルト粘着剤組成物
JPH06166800A (ja) * 1992-12-01 1994-06-14 Nippon Petrochem Co Ltd エポキシ樹脂組成物
JPH09263713A (ja) * 1996-03-28 1997-10-07 Kansai Paint Co Ltd 防食塗料組成物
JPH09316294A (ja) * 1996-05-28 1997-12-09 Nippon Petrochem Co Ltd ホットメルト組成物およびそれに用いる変性芳香族石油樹脂

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS53125461A (en) * 1977-04-11 1978-11-01 Nippon Oil Co Ltd Epoxy resin composition
JPS54131660A (en) * 1978-04-03 1979-10-12 Mitsui Petrochem Ind Ltd Epoxy resin composition
JPH0286644A (ja) * 1988-09-22 1990-03-27 Nippon Steel Chem Co Ltd クマロンインデン樹脂乳化組成物および接着剤
JPH04173889A (ja) * 1990-11-06 1992-06-22 Tosoh Corp ホットメルト接着剤
JPH05105858A (ja) * 1991-10-17 1993-04-27 Nippon Steel Chem Co Ltd ホツトメルト粘着剤組成物
JPH06166800A (ja) * 1992-12-01 1994-06-14 Nippon Petrochem Co Ltd エポキシ樹脂組成物
JPH09263713A (ja) * 1996-03-28 1997-10-07 Kansai Paint Co Ltd 防食塗料組成物
JPH09316294A (ja) * 1996-05-28 1997-12-09 Nippon Petrochem Co Ltd ホットメルト組成物およびそれに用いる変性芳香族石油樹脂

Also Published As

Publication number Publication date
JPH11323247A (ja) 1999-11-26
KR20010014326A (ko) 2001-02-26
CN1162486C (zh) 2004-08-18
FI121995B (fi) 2011-07-15
KR100577920B1 (ko) 2006-05-09
JP4150104B2 (ja) 2008-09-17
CN1272125A (zh) 2000-11-01
FI20000039A (fi) 2000-01-10

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