WO2013084824A1 - Siccatif pour peinture et peinture l'utilisant - Google Patents

Siccatif pour peinture et peinture l'utilisant Download PDF

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Publication number
WO2013084824A1
WO2013084824A1 PCT/JP2012/081117 JP2012081117W WO2013084824A1 WO 2013084824 A1 WO2013084824 A1 WO 2013084824A1 JP 2012081117 W JP2012081117 W JP 2012081117W WO 2013084824 A1 WO2013084824 A1 WO 2013084824A1
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WIPO (PCT)
Prior art keywords
paint
acid
fatty acid
dryer
resin
Prior art date
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PCT/JP2012/081117
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English (en)
Japanese (ja)
Inventor
松永　茂樹
中野　宏明
Original Assignee
Dic株式会社
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Publication of WO2013084824A1 publication Critical patent/WO2013084824A1/fr

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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
    • C09D201/00—Coating compositions based on unspecified macromolecular compounds
    • C09D201/02—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups
    • C09D201/06—Coating compositions based on unspecified macromolecular compounds characterised by the presence of specified groups, e.g. terminal or pendant functional groups containing oxygen atoms
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/04—Oxygen-containing compounds
    • C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
    • C08K5/098—Metal salts of carboxylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; OIL DRYING AGENTS, i.e. SICCATIVES; TURPENTINE
    • C09F9/00—Compounds to be used as driers, i.e. siccatives
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J11/00—Recovery or working-up of waste materials
    • C08J11/04—Recovery or working-up of waste materials of polymers
    • C08J11/10—Recovery or working-up of waste materials of polymers by chemically breaking down the molecular chains of polymers or breaking of crosslinks, e.g. devulcanisation
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2367/00—Characterised by the use of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Derivatives of such polymers
    • C08J2367/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
    • Y02W30/00—Technologies for solid waste management
    • Y02W30/50—Reuse, recycling or recovery technologies
    • Y02W30/62—Plastics recycling; Rubber recycling

Definitions

  • the present invention relates to a dryer which is a drying accelerator for a paint using an oxidation polymerization type resin, and a paint using the dryer.
  • a drying accelerator (dryer) for drying the paint is added to the paint containing the oxidation polymerization type resin.
  • the dryer used is generally a metal salt of a heavy metal such as cobalt, manganese, lead, iron or zinc and various carboxylic acids (hereinafter sometimes abbreviated as “metal soap”).
  • metal soaps cobalt metal soap has been used as a main dryer so far because of its excellent drying performance.
  • Cobalt metal soap has excellent drying performance, but is listed in Group 2B, which is listed as “suspected to be carcinogenic to humans” in the list of carcinogenic risks of the International Cancer Institute. There is a point that there is a concern, the supply of metal cobalt is unstable because it is a rare metal, the cost of cobalt metal soap is expensive, etc., while reducing the amount of cobalt metal soap used, it is high There has been a demand for a dryer having curing performance.
  • cobalt metal soap in order to achieve a smaller amount of cobalt metal soap used, cobalt metal soap, manganese metal soap, and at least one amino alcohol selected from diethanolamine, diethylethanolamine, dibutylethanolamine, and n-butyldiethanolamine are contained.
  • the dryer which performs is proposed (for example, refer patent document 1).
  • cobalt metal soap since cobalt metal soap is still used, it has not solved the above-mentioned carcinogenic concerns, raw material supply anxiety and high cost problems.
  • Patent Document 2 As a dryer that does not use cobalt metal, a dryer using manganese soap and bipyridyl in combination has already been proposed before the disclosure of Patent Document 1 (for example, see Patent Document 2).
  • the problem to be solved by the present invention is to provide a paint drier that does not use cobalt metal soap, which is likely to be affected by the human body, and that can shorten the coating interval during repeated coating.
  • the present invention relates to a paint dryer comprising a fatty acid manganese salt (A) and an amino alcohol (B) represented by the following general formula (1), and a paint using the same.
  • R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 1 and X 2 each independently represents an alkylene group having 2 to 6 carbon atoms
  • Y Is —NR 3 — wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or an oxygen atom.
  • the paint dryer of the present invention can provide a paint capable of shortening the interval between coating times while solving the problems of carcinogenicity, uneasy supply of raw materials, and high cost.
  • the paint dryer of the present invention contains a fatty acid manganese salt (A) and an amino alcohol (B) represented by the following general formula (1).
  • R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 1 and X 2 each independently represents an alkylene group having 2 to 6 carbon atoms
  • Y Is —NR 3 — wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or an oxygen atom.
  • the fatty acid manganese salt (A) is a manganese salt of a fatty acid, and as the fatty acid, octylic acid, naphthenic acid, neodecanoic acid, isononanoic acid, tung oil acid, linseed oil acid, soybean oil acid, resin acid, tall oil fatty acid Etc. These fatty acid manganese salts (A) can be used alone or in combination of two or more.
  • the fatty acid manganese salt (A) is obtained by dissolving a fatty acid in water as a water-soluble salt, usually a sodium salt, and adding water-soluble manganese salt thereto to carry out an ion exchange reaction called metathesis, and washing with water. It can be obtained by dehydration and filtration.
  • the amino alcohol (B) is a compound represented by the following general formula (1).
  • an amino alcohol having the structure represented by the following general formula (1) it is possible to exhibit excellent drying performance such that drying time is short and wrinkles and shrinkage due to skinning can be prevented.
  • R 1 and R 2 each independently represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms
  • X 1 and X 2 each independently represents an alkylene group having 2 to 6 carbon atoms
  • Y Is —NR 3 — wherein R 3 represents a hydrogen atom or an alkyl group having 1 to 6 carbon atoms or an oxygen atom.
  • X 1 and X 2 are each an alkylene having 2 to 3 carbon atoms. What is group is preferable.
  • amino alcohol (B) examples include 2-[(2-dimethylaminoethyl) methylamino] ethanol, 2- (2-aminoethyl) aminoethanol, 1- (2-aminoethyl) amino-2- Examples include propanol, 2- (3-aminopropylamino) ethanol, 2- (2-dimethylaminoethoxy) ethanol and the like. These amino alcohols (B) can be used alone or in combination of two or more.
  • the mixing ratio (a) / (B) on the mass basis of the manganese metal (a) and the amino alcohol (B) in the fatty acid manganese salt (A) is 1 /
  • the range is preferably 0.1 to 1/30, more preferably 1 / 0.3 to 1/20, and even more preferably 1 / 0.5 to 1/10. .
  • the nitrogen atom in the amino alcohol (B) coordinates to the metal (manganese), changes the electronic state of the metal, enhances the activity and promotes the oxidation catalytic action of the manganese soap,
  • the present inventors consider that the recoating property and the gloss of the coating film are improved by promoting the drying of the coating film and uniformly curing from the surface of the coating film to the inside, thereby improving the internal drying property. .
  • the paint dryer of the present invention is preferably used as a solution with good handling properties by diluting the fatty acid manganese salt (A) and the amino alcohol (B) with a diluent (C).
  • a diluent examples include hydrocarbon solvents such as toluene, xylene, heptane, hexane, and mineral spirits; alcohol solvents such as methanol, ethanol, propanol, and cyclohexanol; ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • Solvents such as propyl ether, methyl cellosolve, cellosolve, butyl cellosolve, methyl carbitol; fatty acid esters such as caproic acid methyl ester, capric acid methyl ester, lauric acid methyl ester; soybean oil, linseed oil, rapeseed oil, safflower Vegetable oils such as oil; the following general formula (2)
  • R 4 is an alkyl group having 5 to 11 carbon atoms
  • R 5 is an alkyl group having 1 to 3 carbon atoms.
  • the fatty acid ester (C1) is obtained by esterifying a carboxylic acid having 6 to 12 carbon atoms and an alcohol having 1 to 3 carbon atoms.
  • the carbon chain of the carboxylic acid and the alcohol is It may be linear or branched.
  • Examples of the fatty acid ester (C1) include caproic acid methyl ester, enanthic acid methyl ester, caprylic acid methyl ester, pelargonic acid methyl ester, capric acid methyl ester, lauric acid methyl ester, caproic acid ethyl ester, and enanthic acid ethyl ester.
  • These fatty acid esters can be used alone or in combination of two or more.
  • caproic acid methyl ester, capric acid methyl ester, and lauric acid methyl ester are preferred because of their low odor.
  • lauric acid methyl ester is preferable because it can achieve both a reduction in viscosity and a reduction in odor in a printing ink dryer.
  • the mixing ratio of the total amount of the fatty acid manganese salt (A) and amino alcohol (B) and the diluent (C) on a mass basis [ (A) + (B)] / (C) is preferably in the range of 10/90 to 95/5, more preferably in the range of 40/60 to 80/20, and 20/80 to 90. More preferably, the range is / 10.
  • the paint of the present invention is characterized by containing the paint dryer of the present invention and an oxidative polymerization type unsaturated resin.
  • oxidative polymerization type unsaturated resin examples include an oxidative polymerization curable alkyd resin, an oxidative polymerization curable urethane resin, and an oxidative polymerization curable modified epoxy resin.
  • oxidative polymerization curable alkyd resin examples include ester resins mainly composed of a polybasic acid component, a polyhydric alcohol component, and an oil fatty acid.
  • polybasic acid component examples include dibasic acids such as phthalic anhydride, isophthalic acid, terephthalic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, succinic acid, fumaric acid, adipic acid, sebacic acid, and maleic anhydride. And lower alkyl esterified products of these acids are mainly used. Furthermore, if necessary, tribasic or higher polybasic acids such as trimellitic anhydride, methylcyclohexenic carboxylic acid, pyromellitic anhydride; sulfophthalic acid, sulfoisophthalic acid and ammonium salts thereof, sodium salts, lower alkyl esterified products, etc. Can be used.
  • monobasic acids such as benzoic acid, crotonic acid, and pt-butylbenzoic acid can be used in combination for the purpose of adjusting the molecular weight.
  • polyhydric alcohol component examples include ethylene glycol, diethylene glycol, propylene glycol, 1,4-butanediol, neopentyl glycol, 3-methylpentanediol, 1,4-hexanediol, 1,6-hexanediol, and the like.
  • a dihydric alcohol is mentioned.
  • trihydric or higher polyhydric alcohols such as glycerin, trimethylolethane, trimethylolpropane, and pentaerythritol; polyhydric alcohols having a polyoxyethylene group, and the like can be used in combination. These polyhydric alcohols can be used alone or in admixture of two or more.
  • a part of the acid component and alcohol component may be replaced with dimethylolpropionic acid, oxypivalic acid, paraoxybenzoic acid, etc .; lower alkyl esters of these acids; oxyacid components such as lactones such as ⁇ -caprolactone. it can.
  • oil fatty acid examples include coconut oil fatty acid, soybean oil fatty acid, linseed oil fatty acid, safflower oil fatty acid, tall oil fatty acid, dehydrated castor oil fatty acid, and kiri oil fatty acid.
  • the oil length of the alkyd resin is preferably in the range of 5 to 80% by mass, particularly 20 to 70% by mass, from the viewpoints of the curability, toughness, feeling of feeling of the coating film, and the like.
  • an epoxy-modified alkyd resin obtained by partially esterifying an epoxy compound using an epoxy compound as part of an alcohol component a maleated alkyd resin obtained by introducing maleic anhydride into an alkyd resin; a maleated alkyd resin and a hydroxyl group-containing alkyd Grafted alkyd resins obtained by adding a resin; vinyl-modified alkyd resins obtained by graft-polymerizing vinyl monomers such as styrene and (meth) acrylic acid ester to alkyd resins can also be used.
  • polyethylene terephthalate for example, PET bottles
  • polyester products such as polyethylene terephthalate and polybutylene terephthalate that use terephthalic acid as the main raw material (films, fibers, automotive parts)
  • regenerated PES polyester resin mainly made of terephthalic acid regenerated from scraps, etc. generated during the manufacture of electronic components, etc.
  • the regenerated PES is dissolved, depolymerized, and esterified to obtain an alkyd resin, a maleated alkyd resin obtained by reacting the alkyd resin with maleic anhydride, the alkyd Resin and ethylenically unsaturated groups Etc. are modified alkyd resins obtained by reacting an acid anhydride having no may also be used.
  • the oxidative polymerization curable alkyd resin described in detail above preferably has a Gardner viscosity (25 ° C.) of 15 to 60 Stokes from the viewpoint of good curability and coating film properties.
  • the urethane resin is not particularly limited, and for example, a urethane, a urethane resin obtained by reacting a polyol, an oil and fat with a polyhydric alcohol, and a polyisocyanate can be used.
  • polyisocyanate examples include aliphatic isocyanates such as 1,4-tetramethylene diisocyanate, 1,6-hexamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, and 2,8-diisocyanate methyl caproate.
  • Alicyclic disissocyanates such as 3-isocyanate methyl-3,5,5-trimethylcyclohexyl isocyanate and methylcyclohexyl-2,4-diisocyanate; toluylene diisocyanate, diphenylmethane diisocyanate, 1,5-naphthene diisocyanate, diphenylmethyl Aromatic dii such as methane diisocyanate, tetraalkyldiphenylmethane diisocyanate, 4,4-dibenzyl diisocyanate, 1,3-phenylene diisocyanate Cyanates; chlorinated diisocyanates include brominated diisocyanates etc., can be used as these alone, or two or more thereof.
  • polystyrene resins examples include various polyols commonly used in the production of urethane resins, such as diethylene glycol, butanediol, hexanediol, neopentyl glycol, bisphenol A, cyclohexanedimethanol, trimethylolpropane, glycerin, pentaerythritol, and polyethylene glycol.
  • Examples of the polyol obtained by esterifying the fat and the polyhydric alcohol include those obtained by esterifying a fat and oil having an iodine value of 7 to 200 and a polyhydric alcohol such as trimethylolpropane and pentaerythritol.
  • a polyhydric alcohol such as trimethylolpropane and pentaerythritol.
  • Mitsui Chemicals, Inc Commercially available products such as “XP1076E”, “XP1077E”, “XP1580E”, “FB20-50XB” manufactured by the company can also be used.
  • Examples of the oxidative polymerization curable modified epoxy resin include resins obtained by reacting an epoxy resin with an unsaturated fatty acid component and an acid group-containing acrylic component as raw materials.
  • the resin raw material composition is 30 to 50% by weight of the epoxy resin, 25 to 40% by weight of the unsaturated fatty acid component, and 10 to 45% by weight of the acid group-containing acrylic component with respect to the total weight of the raw material of 100% by weight, It is preferable from the viewpoint of excellent physical properties.
  • the iodine value of the oxidative polymerization curable modified epoxy resin is preferably from 30 to 100, particularly preferably from 35 to 90, from the viewpoint of obtaining good curability.
  • the epoxy resin that can be used as a raw material is not particularly limited, but is bisphenol A type epoxy resin, hydrogenated bisphenol A type epoxy resin, bisphenol from the viewpoint of easy modification and excellent performance of the resulting cured coating film.
  • Bisphenol type epoxy resins such as F type epoxy resins are preferred. These may be used alone or in combination of two or more.
  • any natural or synthetic unsaturated fatty acid can be used.
  • it can be obtained from tung oil, linseed oil, castor oil, dehydrated castor oil, safflower oil, tall oil, soybean oil, coconut oil.
  • Unsaturated fatty acids can be used.
  • the acid group-containing acrylic component for example, a mixture of (meth) acrylic acid and an acrylic monomer containing no acid group such as styrene or (meth) acrylic acid ester can be used.
  • an acrylic monomer containing no acid group such as styrene or (meth) acrylic acid ester
  • styrene is preferable because excellent coating film hardness can be obtained.
  • the oxidation polymerization curable modified epoxy resin can be obtained as follows. First, an epoxy ester resin is produced from an epoxy resin and an unsaturated fatty acid component. For example, an epoxy resin and an unsaturated fatty acid component are used in a suitable solvent such as toluene and xylene, using a condensation catalyst, and if necessary, at 150 to 250 ° C. in an inert gas atmosphere such as nitrogen gas, An epoxy ester resin is obtained by reacting until a desired acid value is obtained.
  • the condensation catalyst for example, dibutyltin oxide, tetra n-butylammonium bromide and the like can be used.
  • the obtained epoxy ester resin is reacted with the acid group-containing acrylic component to obtain an oxidative polymerization curable modified epoxy resin.
  • the reaction between the epoxy ester resin and the acid group-containing acrylic component can be carried out in the temperature range of 80 to 150 ° C. in the presence of a polymerization initiator and in an inert gas atmosphere such as nitrogen gas.
  • a polymerization initiator various substances such as peroxides and azo compounds can be used.
  • “Kayabutyl B (alkyl perester type)” manufactured by Kayaku Akzo is used in an amount of 0. It can be used at a ratio of 1 to 20 parts by mass.
  • an oxidative polymerization curable alkyd resin is preferable because it is inexpensive and easily available in the present invention and is excellent in the drying property (practicality) of the paint.
  • the paint of the present invention preferably further contains an organic solvent.
  • organic solvent examples include the hydrocarbon solvents, alcohol solvents, ketone solvents, and ether solvents.
  • the paint of the present invention may further include a colorant, a diluent, a pigment dispersant, a surface conditioner, an ultraviolet absorber, an antifoaming agent, a thickener, an antisettling agent, etc.
  • a colorant e.g., a diluent, a pigment dispersant, a surface conditioner, an ultraviolet absorber, an antifoaming agent, a thickener, an antisettling agent, etc.
  • examples of the colorant include carbon black, phthalocyanine pigment, dial, azo pigment, quinacridone pigment and the like.
  • examples of the diluent include hydrocarbon solvents such as toluene, xylene, heptane, hexane, and mineral spirit; alcohol solvents such as methanol, ethanol, propanol, and cyclohexanol; ketones such as methyl ethyl ketone, methyl isobutyl ketone, and cyclohexanone.
  • Solvents such as propyl ether, methyl cellosolve, cellosolve, butyl cellosolve, methyl carbitol; fatty acid esters such as caproic acid methyl ester, capric acid methyl ester, lauric acid methyl ester; soybean oil, linseed oil, rapeseed oil, sa And vegetable oils such as flower oil.
  • the blending amount of the dryer of the present invention with respect to the paint is not particularly limited, but the total mass of the metal components in the dryer is in the range of 0.005 to 1.5 parts by mass with respect to 100 parts by mass of the oxidation polymerization type unsaturated resin. It is preferable.
  • the coating material of the present invention described in detail above can be applied to an object to be coated, dried and cured by a conventional method to obtain a coating film.
  • a base material (object to be coated) on which the paint of the present invention can be applied for example, steel and the like can be mentioned.
  • drying conditions (curing conditions) after coating there is a normal drying.
  • the coating material of the present invention can exhibit excellent curability even when the coating film is thick, it is particularly useful as a coating material for thick coatings.
  • the range may be 500 ⁇ m. Therefore, the paint of the present invention is useful as an architectural paint.
  • Comparative Example 1 (Preparation of a comparative paint dryer) 12 parts of cobalt naphthenate and 38 parts of zirconium octylate were dissolved in 50 parts of mineral spirit to obtain a comparative coating dryer 1 '. This dryer was made to demonstrate the average level of performance of prior art metal soaps including cobalt metal soaps.
  • Comparative Example 2 (same as above) 56 parts of manganese naphthenate and 18 parts of 2,2′-bipyridyl were dissolved in 26 parts of mineral spirit to obtain a comparative paint dryer 2 ′.
  • Example 6 (Preparation of paint) 1960 g of titanium white pigment (“JR-701” manufactured by Teika Co., Ltd.), resin for paint “Beccosol P-470-70” (manufactured by DIC Co., Ltd., alkyd resin having an oxidation-polymerized unsaturated fatty acid group in the molecule) 3340 g, 280 g of mineral spirit, and 20 g of anti-skinning agent (methyl ethyl ketoxime) in 40 g of the mixture obtained by kneading with three rolls, the ratio of manganese metal content to 0.06% of the coating dryer 1 for 100 parts of resin non-volatile content It added so that the coating material 1 of this invention might be prepared.
  • the drying test of the paint 1, the glossiness of the coating film obtained, and the test of overcoating were conducted by the following methods. The evaluation results are shown in Table 2.
  • ⁇ Testing method for drying properties of paint> ⁇ Method for measuring drying time>
  • the coating material was applied on a glass plate using a 3 mil applicator, and then tested using a drying time recorder (“Model No. 404” manufactured by Dazai Equipment Co., Ltd.). The measurement was performed in a constant temperature and humidity chamber (25 ° C., 50% RH).
  • the drying time of the coating material was the time until the coating material was completely dried and disappeared after the coating material was applied on the glass plate and the coating material was completely dried by the needle of the drying time recorder ( Unit: hours).
  • ⁇ Multi-layer coating test> Using an applicator on a glass plate, draw a 152 ⁇ m coating film and use the applicator after a certain time (4 hours, 8 hours, 1 day, 2 days, and 3 days) at a temperature of 25 degrees and a humidity of 50%. The coating film with a thickness of 152 ⁇ m was applied again at a temperature of 25 ° C. and a humidity of 50%, and after drying for 7 days, the state of the coating film surface was visually observed.
  • Comparative Example 3 A comparison was made in the same manner as in Example 6 except that the paint dryer 1 'for comparison was added so that the ratio of the cobalt metal content to 100 parts of the resin non-volatile content was 0.06% instead of using the paint dryer 1 A control paint 1 'was obtained. The drying time was measured in the same manner as in Example 6, and the results are shown in Table 3.
  • Comparative Example 4 A comparison was made in the same manner as in Example 6 except that instead of using the paint dryer 1, a comparative paint dryer 2 'was added so that the ratio of manganese metal content to 100 parts of the resin non-volatile content was 0.06%. A control paint 2 'was obtained. The drying time was measured in the same manner as in Example 6, and the results are shown in Table 3.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Paints Or Removers (AREA)

Abstract

La présente invention a pour objet : un siccatif pour peinture qui n'utilise pas un savon métallique au cobalt au sujet duquel il y a des inquiétudes concernant son impact sur le corps humain, ledit siccatif pouvant raccourcir le délai de recouvrement lors du recouvrement ; et une peinture l'utilisant. Le siccatif pour peinture de l'invention contient un sel de manganèse d'acide gras (A) et un aminoalcool (B) représenté par la formule générale (1) (dans la formule, R1 et R2 représentent chacun indépendamment un atome d'hydrogène ou un groupe alkyle en C1-6 ; X1 et X2 représentent chacun indépendamment un groupe alkylène en C2-6 ; et Y représente -NR3- (R3 représentant un atome d'hydrogène ou un groupe alkyle en C1-6) ou un atome d'oxygène) ; et la peinture selon l'invention contient ledit siccatif pour peinture.
PCT/JP2012/081117 2011-12-06 2012-11-30 Siccatif pour peinture et peinture l'utilisant WO2013084824A1 (fr)

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JP2011-266763 2011-12-06

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9896603B2 (en) 2013-07-08 2018-02-20 Dic Corporation Curing accelerator for oxidative polymerization-type unsaturated resin, printing ink, and coating material
US10738203B2 (en) 2015-09-08 2020-08-11 Dic Corporation Curing accelerator for oxidatively polymerizable unsaturated resin, printing ink and coating material
JP7183461B1 (ja) 2022-03-15 2022-12-05 中国塗料株式会社 変性（メタ）アクリル樹脂系塗料組成物、積層塗膜、塗膜付き基材およびその製造方法
WO2024057813A1 (fr) * 2022-09-13 2024-03-21 Dic株式会社 Promoteur de durcissement pour résine insaturée de type à polymérisation oxydative et composition de résine durcissable

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001049102A (ja) * 1999-06-03 2001-02-20 Dainippon Ink & Chem Inc 硬化促進剤及び樹脂組成物
JP2003201424A (ja) * 2001-10-26 2003-07-18 Dainippon Ink & Chem Inc 印刷インキ用ドライヤー及び該ドライヤーを含む印刷インキ
JP2007119619A (ja) * 2005-10-28 2007-05-17 Dainippon Ink & Chem Inc 水性塗料用硬化促進剤
WO2011158694A1 (fr) * 2010-06-14 2011-12-22 Dic株式会社 Agent de séchage pour encre d'impression et encre d'impression l'utilisant

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2001049102A (ja) * 1999-06-03 2001-02-20 Dainippon Ink & Chem Inc 硬化促進剤及び樹脂組成物
JP2003201424A (ja) * 2001-10-26 2003-07-18 Dainippon Ink & Chem Inc 印刷インキ用ドライヤー及び該ドライヤーを含む印刷インキ
JP2007119619A (ja) * 2005-10-28 2007-05-17 Dainippon Ink & Chem Inc 水性塗料用硬化促進剤
WO2011158694A1 (fr) * 2010-06-14 2011-12-22 Dic株式会社 Agent de séchage pour encre d'impression et encre d'impression l'utilisant

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US9896603B2 (en) 2013-07-08 2018-02-20 Dic Corporation Curing accelerator for oxidative polymerization-type unsaturated resin, printing ink, and coating material
US10738203B2 (en) 2015-09-08 2020-08-11 Dic Corporation Curing accelerator for oxidatively polymerizable unsaturated resin, printing ink and coating material
JP7183461B1 (ja) 2022-03-15 2022-12-05 中国塗料株式会社 変性（メタ）アクリル樹脂系塗料組成物、積層塗膜、塗膜付き基材およびその製造方法
JP2023135579A (ja) * 2022-03-15 2023-09-28 中国塗料株式会社 変性（メタ）アクリル樹脂系塗料組成物、積層塗膜、塗膜付き基材およびその製造方法
WO2024057813A1 (fr) * 2022-09-13 2024-03-21 Dic株式会社 Promoteur de durcissement pour résine insaturée de type à polymérisation oxydative et composition de résine durcissable

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