WO2020003781A1 - Composition de résine d'uréthane, agent de traitement de surface, et article - Google Patents

Composition de résine d'uréthane, agent de traitement de surface, et article Download PDF

Info

Publication number
WO2020003781A1
WO2020003781A1 PCT/JP2019/019057 JP2019019057W WO2020003781A1 WO 2020003781 A1 WO2020003781 A1 WO 2020003781A1 JP 2019019057 W JP2019019057 W JP 2019019057W WO 2020003781 A1 WO2020003781 A1 WO 2020003781A1
Authority
WO
WIPO (PCT)
Prior art keywords
urethane resin
mass
parts
resin composition
range
Prior art date
Application number
PCT/JP2019/019057
Other languages
English (en)
Japanese (ja)
Inventor
竹村　潔
信也 久野
宏之 千々和
Original Assignee
Dic株式会社
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 Dic株式会社 filed Critical Dic株式会社
Priority to JP2020527266A priority Critical patent/JPWO2020003781A1/ja
Priority to CN201980041789.6A priority patent/CN112313287A/zh
Publication of WO2020003781A1 publication Critical patent/WO2020003781A1/fr
Priority to JP2023175078A priority patent/JP2023171513A/ja

Links

Classifications

    • 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
    • C08K5/20—Carboxylic acid amides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • 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
    • C09D5/02—Emulsion paints including aerosols
    • 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
    • C09D7/00—Features of coating compositions, not provided for in group C09D5/00; Processes for incorporating ingredients in coating compositions
    • C09D7/20—Diluents or solvents

Definitions

  • the present invention relates to a urethane resin composition, a surface treatment agent, and an article having a layer formed by the surface treatment agent.
  • the surface is finished with a surface treatment agent from the viewpoint of imparting chemical resistance and design.
  • the material used for the conventional surface treatment agent is mainly a solvent-based resin composition containing an organic solvent.However, due to the recent rise in environmental regulations, the use of an aqueous surface treatment agent in which the amount of the organic solvent used is limited. Development is underway.
  • aqueous surface treating agent for example, a polyurethane having specific mechanical properties, a carbodiimide crosslinking agent, and an aqueous surface treating agent containing a filler are disclosed (for example, see Patent Document 1).
  • a film-forming auxiliary such as NMP as a countermeasure
  • the problem to be solved by the present invention is to provide a urethane resin composition which can provide a film having excellent chemical resistance in a urethane resin composition containing water.
  • the present invention comprises a urethane resin (A), water (B), and an organic solvent (C), wherein the organic solvent (C) is 3-methoxy-N, N-dimethylpropanamide and / or It is intended to provide a urethane resin composition characterized by being 3-butoxy-N, N-dimethylpropanamide.
  • the present invention also provides a surface treatment agent containing the urethane resin composition, and an article having a layer formed by the surface treatment agent.
  • the urethane resin composition of the present invention can provide a film having excellent chemical resistance. Therefore, the urethane resin composition of the present invention can be suitably used as a surface treatment agent for various articles.
  • the urethane resin composition of the present invention contains a urethane resin (A), water (B), and a specific organic solvent (C).
  • the urethane resin (A) can be dispersed in water (B), and is, for example, a urethane resin having a hydrophilic group such as an anionic group, a cationic group, or a nonionic group; A urethane resin dispersed in B) can be used. These urethane resins (A) may be used alone or in combination of two or more.
  • a method for obtaining the urethane resin having an anionic group for example, a method using one or more compounds selected from the group consisting of a compound having a carboxyl group and a compound having a sulfonyl group as a raw material may be mentioned.
  • Examples of the compound having a carboxyl group include 2,2-dimethylolpropionic acid, 2,2-dimethylolbutanoic acid, 2,2-dimethylolbutyric acid, 2,2-dimethylolpropionic acid, and Herbic acid or the like can be used. These compounds may be used alone or in combination of two or more.
  • Examples of the compound having a sulfonyl group include 3,4-diaminobutanesulfonic acid, 3,6-diamino-2-toluenesulfonic acid, 2,6-diaminobenzenesulfonic acid, and N- (2-aminoethyl)- 2-aminoethylsulfonic acid and the like can be used. These compounds may be used alone or in combination of two or more.
  • the carboxyl group and the sulfonyl group may be partially or entirely neutralized by a basic compound in the resin composition.
  • the basic compound include organic amines such as ammonia, triethylamine, pyridine, and morpholine; alkanolamines such as monoethanolamine and dimethylethanolamine; and metal base compounds including sodium, potassium, lithium, and calcium. Can be.
  • a method for obtaining the urethane resin having a cationic group for example, a method using one or more compounds having an amino group as a raw material may be mentioned.
  • Examples of the compound having an amino group include compounds having a primary and secondary amino group such as triethylenetetramine and diethylenetriamine; N-alkyldialkanolamines such as N-methyldiethanolamine and N-ethyldiethanolamine; Compounds having a tertiary amino group such as N-alkyldiaminoalkylamine such as diaminoethylamine and N-ethyldiaminoethylamine can be used. These compounds may be used alone or in combination of two or more.
  • a method for obtaining the urethane resin having a nonionic group for example, a method using one or more compounds having an oxyethylene structure as a raw material may be mentioned.
  • polyether polyol having an oxyethylene structure such as polyoxyethylene glycol, polyoxyethylene polyoxypropylene glycol, and polyoxyethylene polyoxytetramethylene glycol can be used. These compounds may be used alone or in combination of two or more.
  • the amount of the raw material used for producing the urethane resin having the above hydrophilic group is such that urethane is more excellent in chemical resistance, abrasion resistance, weather resistance, and hydrolysis resistance. It is preferably in the range of 0.1 to 15% by mass, more preferably in the range of 1 to 10% by mass, and even more preferably in the range of 1.5 to 7% by mass of the raw material of the resin (A).
  • Examples of the emulsifier that can be used for obtaining the urethane resin that is forcibly dispersed in water (B) include, for example, polyoxyethylene nonylphenyl ether, polyoxyethylene lauryl ether, polyoxyethylene styryl phenyl ether, polyoxyethylene Nonionic emulsifiers such as ethylene sorbitol tetraoleate and polyoxyethylene / polyoxypropylene copolymers; fatty acid salts such as sodium oleate; alkyl sulfates; alkyl benzene sulfonates; alkyl sulfosuccinates; naphthalene sulfonates; Anionic emulsifiers such as polyoxyethylene alkyl sulfate, sodium alkane sulfonate, sodium salt of alkyl diphenyl ether sulfonate; alkyl amine salt, alkyl trimethyl ammonium Arm salts,
  • urethane resin (A) specifically, for example, a raw material used for producing the above-mentioned urethane resin having a hydrophilic group, polyisocyanate (a1), polyol (a2), and a chain extender ( The reactants of a3) can be used. For these reactions, known urethanation reactions can be used.
  • polyisocyanate (a1) examples include aromatic polyisocyanates such as phenylene diisocyanate, tolylene diisocyanate, diphenylmethane diisocyanate, xylylene diisocyanate, naphthalene diisocyanate, polymethylene polyphenyl polyisocyanate, and carbodiimidated diphenylmethane polyisocyanate; hexamethylene diisocyanate And aliphatic or alicyclic polyisocyanates such as lysine diisocyanate, cyclohexane diisocyanate, isophorone diisocyanate, dicyclohexylmethane diisocyanate, xylylene diisocyanate, tetramethyl xylylene diisocyanate, dimer acid diisocyanate and norbornene diisocyanate. These polyisocyanates may be used alone or in combination of two or more.
  • the polyisocyanate (a1) it is preferable to use an alicyclic polyisocyanate from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance, and at least the nitrogen atom of the isocyanate group is cyclohexane. It is more preferable to use a polyisocyanate having one or more structures directly connected to a ring, and it is more preferable to use isophorone diisocyanate and / or dicyclohexylmethane diisocyanate. Further, the amount of the alicyclic polyisocyanate used is preferably 30% by mass or more in the polyisocyanate (a1) from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance. , 40% by mass or more, more preferably 50% by mass or more.
  • the alicyclic polyisocyanate and the aliphatic polyisocyanate may be used as the polyisocyanate (a1). It is preferable to use an isocyanate in combination, and it is preferable to use hexamethylene diisocyanate as the aliphatic polyisocyanate.
  • the content of the alicyclic polyisocyanate in the polyisocyanate (a1) is preferably 30% by mass or more, more preferably 40% by mass or more, and even more preferably 50% by mass or more.
  • the amount of the polyisocyanate (a1) used is in the range of 5 to 50% by mass in the raw material of the urethane resin (A) from the viewpoint that more excellent chemical resistance, abrasion resistance and weather resistance are obtained. It is preferably in the range of 15 to 40% by mass, more preferably in the range of 20 to 37% by mass.
  • polyether polyol for example, polyether polyol, polyester polyol, polyacryl polyol, polycarbonate polyol, polybutadiene polyol and the like can be used. These polyols may be used alone or in combination of two or more. Among these, it is preferable to use a polycarbonate polyol from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance.
  • polycarbonate polyol for example, a reaction product of a carbonate ester and / or phosgene and a compound having two or more hydroxyl groups can be used.
  • carbonate ester for example, dimethyl carbonate, diethyl carbonate, diphenyl carbonate, ethylene carbonate, propylene carbonate and the like can be used. These compounds may be used alone or in combination of two or more.
  • Examples of the compound having two or more hydroxyl groups include ethylene glycol, propylene glycol, 1,3-propanediol, 1,4-butanediol, 1,3-butanediol, 1,2-butanediol, 2-methyl 1,3-propanediol, 1,5-pentanediol, neopentyl glycol, 1,6-hexanediol, 1,5-hexanediol, 3-methyl-1,5-pentanediol, 1,7-heptanediol 1,8-octanediol, 1,9-nonanediol, 1,8-nonanediol, 2-ethyl-2-butyl-1,3-propanediol, 1,10-decanediol, 1,12-dodecanediol 1,4-cyclohexanedimethanol, 1,3-cyclohexane
  • 1,3-propanediol, 1,4-butanediol, 1,5-pentanediol, 1,6-propanediol, 1,6-pentanediol and 1,6-propanediol are more excellent in chemical resistance, abrasion resistance, and weather resistance. It is preferable to use one or more compounds selected from the group consisting of -hexanediol, 1,4-cyclohexanedimethanol, 3-methylpentanediol, and 1,10-decanediol. More preferred.
  • the amount of the polycarbonate polyol used is preferably 85% by mass or more in the polyol (a2), and more preferably 90% by mass or more from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance. Is more preferable, and 95 mass% or more is still more preferable.
  • the number average molecular weight of the polycarbonate polyol is preferably in the range of 100 to 100,000 from the viewpoint of obtaining more excellent chemical resistance, mechanical strength, abrasion resistance, and weather resistance. It is more preferably in the range of ⁇ 10,000, further preferably in the range of 2002002,500.
  • the number average molecular weight of the polycarbonate polyol indicates a value measured by a gel permeation column chromatography (GPC) method.
  • the number average molecular weight of the polyol (a2) other than the polycarbonate polyol is preferably in the range of 500 to 100,000, and more preferably in the range of 700 to 50,000, from the viewpoint that more excellent weather resistance is obtained. Preferably, the range is 800 to 10,000.
  • the number average molecular weight of the polyol (a2) indicates a value measured by a gel permeation column chromatography (GPC) method.
  • the amount of the polyol (a2) used is preferably in the range of 30 to 80% by mass, more preferably in the range of 40 to 75% by mass, and more preferably in the range of 50 to 70% by mass in the raw material of the urethane resin (A). Is more preferred.
  • Examples of the chain extender (a3) include those having a number average molecular weight in the range of 50 to 450 (excluding the polycarbonate polyol), and specifically include ethylenediamine, 1,2-propanediamine, 6-hexamethylenediamine, piperazine, 2,5-dimethylpiperazine, isophoronediamine, 1,2-cyclohexanediamine, 1,3-cyclohexanediamine, 1,4-cyclohexanediamine, 4,4′-dicyclohexylmethanediamine, 3,
  • a chain extender having an amino group such as 3'-dimethyl-4,4'-dicyclohexylmethanediamine, 1,4-cyclohexanediamine, hydrazine; ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, , 3- Lopandiol, 1,3-butanediol, 1,4-butanediol, hexamethylene glycol, sac
  • chain extender (a3) among those described above, a chain extender having an amino group is used, because more excellent chemical resistance, mechanical strength, abrasion resistance, and weather resistance are obtained. Is preferable, and piperazine and / or hydrazine are more preferable.
  • the total amount of piperazine and hydrazine is preferably 30% by mass or more in the chain extender (a3), more preferably 50% by mass or more, and 60% by mass. The above is more preferable, and the amount is particularly preferably 80% by mass or more.
  • the chain extender (a3) preferably has an average number of functional groups of less than 3, more preferably less than 2.5. Also,
  • the amount of the chain extender (a3) used is 0.5% in the raw material of the urethane resin (A) from the viewpoint that even more excellent chemical resistance, mechanical strength, abrasion resistance, and weather resistance are obtained.
  • the range is preferably from 10 to 10% by mass, more preferably from 0.7 to 5% by mass, and even more preferably from 0.9 to 2.3.
  • the method for producing the urethane resin (A) includes, for example, reacting the polyisocyanate (a1), the polyol (a2), and a raw material used for producing the urethane resin having a hydrophilic group, thereby obtaining an isocyanate group.
  • the molar ratio [(isocyanate group) / (hydroxyl group and amino group)] to the isocyanate group of (a1) is preferably in the range of 0.8 to 1.2, and is preferably in the range of 0.9 to 1.1. More preferably, it is within the range.
  • the urethane resin (A) it is preferable to deactivate the isocyanate groups remaining in the urethane resin (A).
  • an alcohol having one hydroxyl group such as methanol.
  • the amount of the alcohol to be used is preferably in the range of 0.001 to 10 parts by mass with respect to 100 parts by mass of the urethane resin (A).
  • an organic solvent when producing the urethane resin (A), an organic solvent may be used.
  • the organic solvent include ketone compounds such as acetone and methyl ethyl ketone; ether compounds such as tetrahydrofuran and dioxane; acetate compounds such as ethyl acetate and butyl acetate; nitrile compounds such as acetonitrile; dimethylformamide and N-methylpyrrolidone.
  • An amide compound or the like can be used.
  • These organic solvents may be used alone or in combination of two or more. Preferably, the organic solvent is finally removed by a distillation method or the like.
  • the content of the urethane bond in the urethane resin (A) is preferably in the range of 980 to 4,000 mmol / kg, from the viewpoint that more excellent chemical resistance, wear resistance, and weather resistance can be obtained.
  • the range is more preferably from 2,000 to 3,500 mmol / kg, further preferably from 1,100 to 3,000 mmol / kg, and more preferably from 1,150 to 2,500 mmol / kg.
  • the content of the urethane bond in the urethane resin (A) is determined by the following: the polyisocyanate (a1), the polyol (a2), the raw material used for producing the urethane resin having a hydrophilic group, and the chain extender (a3). ) Indicates a value calculated from the charged amount.
  • the content of the urea bond in the urethane resin (A) is preferably in the range of 315 to 850 mmol / kg from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance, The range is more preferably from 350 to 830 mmol / kg, still more preferably from 400 to 800 mmol / kg, even more preferably from 410 to 770 mmol / kg.
  • the content of the urea bond of the urethane resin (A) is based on the polyisocyanate (a1), the polyol (a2), the raw material used for producing the urethane resin having a hydrophilic group, and the chain extender. A value calculated from the charged amount of (a3) is shown.
  • the content of the alicyclic structure of the urethane resin (A) is in the range of 500 to 3,000 mmol / kg from the viewpoint of obtaining more excellent chemical resistance, abrasion resistance, and weather resistance. Is preferably in the range of 600 to 2,900 mmol / kg, and more preferably in the range of 700 to 2,700 mmol / kg.
  • the content of the alicyclic structure of the urethane resin (A) is based on the polyisocyanate (a1), the polyol (a2), the raw material used for producing the urethane resin having a hydrophilic group, and the chain extension. This shows a value calculated from the charged amount of the agent (a3).
  • the content of the urethane resin (A) is preferably in the range of 3 to 50% by mass, and more preferably 5 to 30% by mass in the urethane resin composition from the viewpoint of coating properties, workability and storage stability. The range is more preferable.
  • the water (B) ion-exchanged water, distilled water or the like can be used.
  • the content of the water (B) is preferably in the range of 30 to 95% by mass in the urethane resin composition, from the viewpoint of coatability, workability and storage stability of the urethane resin composition, A range of 90% by mass is more preferable.
  • the organic solvent (C) it is essential to use 3-methoxy-N, N-dimethylpropanamide and / or 3-butoxy-N, N-dimethylpropanamide.
  • these hydrophilic solvents By using these hydrophilic solvents, the film forming temperature of the urethane resin composition can be lowered, so that the film forming property of the dried film is improved, and excellent chemical resistance can be obtained.
  • these solvents are not included in the regulatory lists in Europe and China, they are environmentally friendly.
  • the content of the organic solvent (C) is from 0.1 to 30% by mass, since a more excellent chemical resistance can be obtained by improving the film forming property, the drying property, and the base adhesion. Is preferably in the range of 3 to 20% by mass, more preferably in the range of 5 to 15% by mass.
  • the organic solvent (C) may contain another organic solvent as needed.
  • the other organic solvent for example, the same organic solvent that can be used for producing the urethane resin (A) can be used.
  • the amount of the organic solvent in the urethane resin composition is preferably 5% by mass or less, more preferably 3% by mass or less.
  • the urethane resin composition of the present invention contains the urethane resin (A), water (B), and organic solvent (C) as essential components, but may use other additives as necessary.
  • Examples of the other additives include a filler (D), a crosslinking agent (E), an emulsifier, an antifoaming agent, a leveling agent, a thickener, a viscoelasticity adjusting agent, an antifoaming agent, a wetting agent, a dispersant, and a preservative.
  • Agents, plasticizers, penetrants, fragrances, bactericides, acaricides, fungicides, ultraviolet absorbers, antioxidants, antistatic agents, flame retardants, dyes, pigments (e.g., titanium white, redwood, phthalocyanine, carbon Black, permanent yellow, etc.) can be used.
  • These additives may be used alone or in combination of two or more.
  • a filler (D) for imparting a matte feeling to the coating film, and mechanical properties of the coating film It is preferable to use a crosslinking agent (E) in order to improve the strength.
  • Examples of the filler (D) include silica particles, organic beads, calcium carbonate, magnesium carbonate, barium carbonate, talc, aluminum hydroxide, calcium sulfate, kaolin, mica, asbestos, mica, calcium silicate, and alumina silicate. Can be used. These fillers may be used alone or in combination of two or more.
  • silica particles for example, dry silica, wet silica and the like can be used. Of these, dry silica is preferred because of its high scattering effect and wide adjustment range of gloss value.
  • the average particle size of these silica particles is preferably in the range of 2 to 14 ⁇ m, and more preferably in the range of 3 to 12 ⁇ m.
  • the average particle size of the silica particles indicates the particle size (the particle size at D50 in the particle size distribution) when the integrated amount occupies 50% in the integrated particle amount curve of the particle size distribution measurement result.
  • organic beads for example, acrylic beads, urethane beads, silicon beads, olefin beads and the like can be used.
  • the amount of the filler (D) to be used can be appropriately determined according to the matt feeling to be imparted.
  • the amount is 1 to 30 parts by mass with respect to 100 parts by mass of the urethane resin (A).
  • the range is 3 to 10 parts by mass.
  • crosslinking agent (E) for example, an isocyanate crosslinking agent, an epoxy crosslinking agent, a carbodiimide crosslinking agent, an oxazolidine crosslinking agent, an oxazoline crosslinking agent, a melamine crosslinking agent and the like can be used. These crosslinking agents may be used alone or in combination of two or more.
  • the amount of the crosslinking agent (E) to be used is, for example, preferably in the range of 5 to 40 parts by mass, more preferably 10 to 30 parts by mass, based on 100 parts by mass of the urethane resin (A). .
  • the urethane resin composition of the present invention can provide a film having excellent chemical resistance. Therefore, the urethane resin composition of the present invention is suitably used as a surface treatment agent for various articles such as synthetic leather, polyvinyl chloride (PVC) leather, thermoplastic olefin resin (TPO) leather, dashboard, and instrument panel. be able to.
  • PVC polyvinyl chloride
  • TPO thermoplastic olefin resin
  • the article of the present invention has a layer formed by the surface treatment agent.
  • the article include, for example, synthetic leather, artificial leather, natural leather, automobile interior seats using polyvinyl chloride (PVC) leather, sports shoes, clothing, furniture, thermoplastic olefin (TPO) leather, and dashboard. , Instrument panels and the like.
  • PVC polyvinyl chloride
  • TPO thermoplastic olefin
  • the thickness of the layer made of the surface treatment agent is, for example, in the range of 0.1 to 100 ⁇ m.
  • urethane prepolymer solution in methyl ethyl ketone 6.8 parts by mass of hydrazine and 15 parts by mass of triethylamine were mixed with the methyl ethyl ketone solution of the urethane prepolymer, and then 820 parts by mass of ion-exchanged water was added to disperse the urethane resin (A-1) in water. A liquid was obtained. Next, methyl ethyl ketone was distilled off from the emulsion, and ion-exchanged water was further added to obtain an aqueous dispersion of a urethane resin (A-1) having a nonvolatile content of 30% by mass.
  • the resulting urethane resin (A-1) had a urethane bond content of 2,052 mmol / kg, a urea bond content of 698 mmol / kg, and an alicyclic structure content of 715 mmol / kg.
  • urethane resin (A-2) having a nonvolatile content of 32% by mass.
  • the urethane resin (A-2) obtained had a urethane bond content of 1,278 mmol / kg, a urea bond content of 435 mmol / kg, and an alicyclic structure content of 1,713 mmol / kg.
  • urethane resin (A-3) having a nonvolatile content of 30% by mass.
  • the urethane resin (A-3) obtained had a urethane bond content of 1,747 mmol / kg, a urea bond content of 576 mmol / kg, and an alicyclic structure content of 2,341 mmol / kg.
  • Example 1 25 parts by mass of the aqueous dispersion of the urethane resin (A-1) obtained in Synthesis Example 1, 5 parts by mass of an oxazoline crosslinking agent (Nippon Shokubai "Epocross WS-500"), and a filler ("ACEMATT TS 100" manufactured by Evonik Degussa) , Silica particles produced by a dry method, average particle diameter: 10 ⁇ m), 2 parts by mass, 3-methoxy-N, N-dimethylpropanamide, 10 parts by mass, and water, 58 parts by mass, to give a urethane resin composition.
  • an oxazoline crosslinking agent Nippon Shokubai "Epocross WS-500”
  • a filler ACEMATT TS 100” manufactured by Evonik Degussa
  • Example 2 25 parts by mass of the aqueous dispersion of the urethane resin (A-1) obtained in Synthesis Example 1, 5 parts by mass of an oxazoline crosslinking agent (Nippon Shokubai "Epocross WS-500"), and a filler ("ACEMATT TS 100" manufactured by Evonik Degussa) ") 2 parts by mass, 20 parts by mass of 3-methoxy-N, N-dimethylpropanamide and 48 parts by mass of water were mixed to obtain a urethane resin composition.
  • an oxazoline crosslinking agent Nippon Shokubai "Epocross WS-500
  • a filler ACEMATT TS 100” manufactured by Evonik Degussa
  • Example 3 25 parts by mass of the aqueous dispersion of the urethane resin (A-1) obtained in Synthesis Example 1, 5 parts by mass of an oxazoline crosslinking agent (Nippon Shokubai "Epocross WS-500"), and a filler ("ACEMATT TS 100" manufactured by Evonik Degussa) ") 2 parts by mass, 3 parts by mass of 3-methoxy-N, N-dimethylpropanamide and 63 parts by mass of water were mixed to obtain a urethane resin composition.
  • an oxazoline crosslinking agent Nippon Shokubai "Epocross WS-500
  • a filler ACEMATT TS 100” manufactured by Evonik Degussa
  • Example 4 25 parts by weight of the aqueous dispersion of the urethane resin (A-2) obtained in Synthesis Example 2, 5 parts by weight of an oxazoline cross-linking agent (Nippon Shokubai "Epocross WS-500"), and a filler ("ACEMATT TS 100" manufactured by Evonik Degussa) ") 2 parts by mass, 10 parts by mass of 3-butoxy-N, N-dimethylpropanamide and 58 parts by mass of water were mixed to obtain a urethane resin composition.
  • an oxazoline cross-linking agent Nippon Shokubai "Epocross WS-500
  • a filler (“ACEMATT TS 100" manufactured by Evonik Degussa) ”
  • Example 5 25 parts by mass of the aqueous dispersion of the urethane resin (A-3) obtained in Synthesis Example 3, 5 parts by mass of an oxazoline cross-linking agent (Nippon Shokubai "Epocross WS-500"), and a filler ("ACEMATT TS 100" manufactured by Evonik Degussa) ") 2 parts by mass, 10 parts by mass of 3-butoxy-N, N-dimethylpropanamide and 58 parts by mass of water were mixed to obtain a urethane resin composition.
  • an oxazoline cross-linking agent Nippon Shokubai "Epocross WS-500
  • a filler ACEMATT TS 100” manufactured by Evonik Degussa
  • the number average molecular weights of the polyols and the like used in the synthesis examples are values obtained by gel permeation column chromatography (GPC) under the following conditions.
  • Measuring device High-speed GPC device (“HLC-8220GPC” manufactured by Tosoh Corporation) Column: The following columns manufactured by Tosoh Corporation were connected in series and used. "TSKgel G5000" (7.8 mm ID x 30 cm) x 1 "TSKgel G4000” (7.8 mm ID x 30 cm) x 1 "TSKgel G3000” (7.8 mm ID x 30 cm) x 1 Book “TSKgel G2000” (7.8 mm ID ⁇ 30 cm) ⁇ 1 Detector: RI (differential refractometer) Column temperature: 40 ° C Eluent: tetrahydrofuran (THF) Flow rate: 1.0 mL / min Injection volume: 100 ⁇ L (tetrahydrofuran solution with a sample concentration of 0.4% by mass) Standard sample: A calibration curve was prepared using the following standard polystyrene.
  • the urethane resin composition of the present invention has excellent chemical resistance.
  • Comparative Example 1 is an embodiment in which no specific organic solvent (C) is used
  • Comparative Examples 2 and 3 are embodiments in which an organic solvent other than the specific organic solvent (C) is used. The chemical resistance was poor.

Landscapes

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

Abstract

La présente invention concerne une composition de résine d'uréthane caractérisée en ce qu'elle contient une résine d'uréthane (A), de l'eau (B) et un solvant organique (C), le solvant organique (C) étant le 3-méthoxy-N,N-diméthylpropaneamide et/ou le 3-butoxy-N,N-diméthylpropaneamide. La présente invention concerne également : un agent de traitement de surface caractérisé en ce qu'il contient la composition de résine d'uréthane ; et un article caractérisé en ce qu'il comporte une couche formée de l'agent de traitement de surface. La quantité du solvant organique (C) contenue dans la composition de résine d'uréthane est de préférence située dans la plage allant de 0,1 à 30 % en masse. Dans le cas où la composition de résine d'uréthane est utilisée dans un agent de traitement de surface, la composition de résine d'uréthane contient en outre de préférence une charge (D).
PCT/JP2019/019057 2018-06-27 2019-05-14 Composition de résine d'uréthane, agent de traitement de surface, et article WO2020003781A1 (fr)

Priority Applications (3)

Application Number Priority Date Filing Date Title
JP2020527266A JPWO2020003781A1 (ja) 2018-06-27 2019-05-14 ウレタン樹脂組成物、表面処理剤、及び、物品
CN201980041789.6A CN112313287A (zh) 2018-06-27 2019-05-14 氨基甲酸酯树脂组合物、表面处理剂及物品
JP2023175078A JP2023171513A (ja) 2018-06-27 2023-10-10 ウレタン樹脂組成物、表面処理剤、及び、物品

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2018-121939 2018-06-27
JP2018121939 2018-06-27

Publications (1)

Publication Number Publication Date
WO2020003781A1 true WO2020003781A1 (fr) 2020-01-02

Family

ID=68986313

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2019/019057 WO2020003781A1 (fr) 2018-06-27 2019-05-14 Composition de résine d'uréthane, agent de traitement de surface, et article

Country Status (3)

Country Link
JP (2) JPWO2020003781A1 (fr)
CN (1) CN112313287A (fr)
WO (1) WO2020003781A1 (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115029058A (zh) * 2022-07-20 2022-09-09 黎明化工研究设计院有限责任公司 一种双组分聚氨酯底涂剂及其制备方法和用途

Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010280847A (ja) * 2009-06-05 2010-12-16 Idemitsu Kosan Co Ltd ウレタン組成物及びそれを用いた塗料、接着剤
JP2011068838A (ja) * 2009-09-28 2011-04-07 Idemitsu Kosan Co Ltd 水性インク組成物
JP2012052040A (ja) * 2010-09-02 2012-03-15 Konica Minolta Ij Technologies Inc 水性インク
JP2015054258A (ja) * 2013-09-10 2015-03-23 関西ペイント株式会社 複層塗膜形成方法
WO2016163394A1 (fr) * 2015-04-07 2016-10-13 宇部興産株式会社 Dispersion aqueuse de résine de polyuréthane, procédé pour sa production et son utilisation
JP2017002217A (ja) * 2015-06-12 2017-01-05 株式会社リコー インク、インクジェット記録方法、記録物
WO2018088511A1 (fr) * 2016-11-11 2018-05-17 株式会社カネコ化学 Agent de démoulage pour article durci de résine durcissable, agent lubrifiant pour article durci de résine durcissable, et agent de réduction de volume pour mousse durcie de résine durcissable
JP2018087292A (ja) * 2016-11-29 2018-06-07 宇部興産株式会社 ポリイミド樹脂基材被覆用水性樹脂分散体組成物、それを含むポリイミド樹脂基材被覆用コーティング剤、ポリイミド樹脂基材被覆用塗料及びポリイミド樹脂基材被覆用プライマー組成物
WO2018235921A1 (fr) * 2017-06-22 2018-12-27 トーヨーポリマー株式会社 Dispersion aqueuse de polyuréthane, procédé de production de dispersion aqueuse de polyuréthane, composition de revêtement à base d'eau, et film de revêtement
WO2019000359A1 (fr) * 2017-06-30 2019-01-03 Dow Global Technologies Llc Dispersions de polyuréthane à base d'eau et leur préparation
JP2019056053A (ja) * 2017-09-21 2019-04-11 富士ゼロックス株式会社 粒子分散液、水性インク、インクカートリッジ、記録装置及び記録方法
JP2019070108A (ja) * 2017-08-02 2019-05-09 宇部興産株式会社 水性ポリウレタン樹脂分散体及びその製造方法

Patent Citations (12)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2010280847A (ja) * 2009-06-05 2010-12-16 Idemitsu Kosan Co Ltd ウレタン組成物及びそれを用いた塗料、接着剤
JP2011068838A (ja) * 2009-09-28 2011-04-07 Idemitsu Kosan Co Ltd 水性インク組成物
JP2012052040A (ja) * 2010-09-02 2012-03-15 Konica Minolta Ij Technologies Inc 水性インク
JP2015054258A (ja) * 2013-09-10 2015-03-23 関西ペイント株式会社 複層塗膜形成方法
WO2016163394A1 (fr) * 2015-04-07 2016-10-13 宇部興産株式会社 Dispersion aqueuse de résine de polyuréthane, procédé pour sa production et son utilisation
JP2017002217A (ja) * 2015-06-12 2017-01-05 株式会社リコー インク、インクジェット記録方法、記録物
WO2018088511A1 (fr) * 2016-11-11 2018-05-17 株式会社カネコ化学 Agent de démoulage pour article durci de résine durcissable, agent lubrifiant pour article durci de résine durcissable, et agent de réduction de volume pour mousse durcie de résine durcissable
JP2018087292A (ja) * 2016-11-29 2018-06-07 宇部興産株式会社 ポリイミド樹脂基材被覆用水性樹脂分散体組成物、それを含むポリイミド樹脂基材被覆用コーティング剤、ポリイミド樹脂基材被覆用塗料及びポリイミド樹脂基材被覆用プライマー組成物
WO2018235921A1 (fr) * 2017-06-22 2018-12-27 トーヨーポリマー株式会社 Dispersion aqueuse de polyuréthane, procédé de production de dispersion aqueuse de polyuréthane, composition de revêtement à base d'eau, et film de revêtement
WO2019000359A1 (fr) * 2017-06-30 2019-01-03 Dow Global Technologies Llc Dispersions de polyuréthane à base d'eau et leur préparation
JP2019070108A (ja) * 2017-08-02 2019-05-09 宇部興産株式会社 水性ポリウレタン樹脂分散体及びその製造方法
JP2019056053A (ja) * 2017-09-21 2019-04-11 富士ゼロックス株式会社 粒子分散液、水性インク、インクカートリッジ、記録装置及び記録方法

Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN115029058A (zh) * 2022-07-20 2022-09-09 黎明化工研究设计院有限责任公司 一种双组分聚氨酯底涂剂及其制备方法和用途
CN115029058B (zh) * 2022-07-20 2023-04-14 黎明化工研究设计院有限责任公司 一种双组分聚氨酯底涂剂及其制备方法和用途

Also Published As

Publication number Publication date
JP2023171513A (ja) 2023-12-01
CN112313287A (zh) 2021-02-02
JPWO2020003781A1 (ja) 2021-08-02

Similar Documents

Publication Publication Date Title
JP2023171513A (ja) ウレタン樹脂組成物、表面処理剤、及び、物品
WO2020003779A1 (fr) Composition de résine d'uréthane, agent de traitement de surface et article
WO2020003780A1 (fr) Composition de résine d'uréthanne, agent de traitement de surface et article
JP7342885B2 (ja) ウレタン樹脂組成物、表面処理剤、及び、物品
JP7342884B2 (ja) ウレタン樹脂組成物、表面処理剤、及び、物品
JP2021098912A (ja) 合成皮革
CN113573906B (zh) 表面处理剂及物品
CN113242875B (zh) 氨基甲酸酯树脂组合物、表面处理剂及物品
CN114786948B (zh) 表面处理层和物品
JP7405077B2 (ja) ウレタン樹脂組成物、表面処理剤、及び、物品
JP7342415B2 (ja) 水性樹脂組成物、表面処理剤、及び、物品
JP7342416B2 (ja) 水性樹脂組成物、表面処理剤、及び、物品
JP2021098913A (ja) 合成皮革
WO2020129669A1 (fr) Composition de résine d'uréthanne, agent de traitement de surface et article

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 19825476

Country of ref document: EP

Kind code of ref document: A1

ENP Entry into the national phase

Ref document number: 2020527266

Country of ref document: JP

Kind code of ref document: A

NENP Non-entry into the national phase

Ref country code: DE

122 Ep: pct application non-entry in european phase

Ref document number: 19825476

Country of ref document: EP

Kind code of ref document: A1