JPH101524A - Acryl-urethane copolymer, production thereof, and coating composition containing the same - Google Patents

Abstract

PROBLEM TO BE SOLVED: To obtain an org. -solvent-soluble acryl-urethane copolymer which gives a tough coating film excellent in softness, durability, etc., by reacting a specific high-molecular linear polyurethane prepolymer with a vinyl compd. SOLUTION: A theoretical amt. of a (meth)acrylic ester having an NCO- reactive hydroxyl group is entered into an addition reaction with the NCO groups at both terminals of an NCO-terminalted linear urethane segment to give a high-molecular linear polyurethane prepolymer having ethylenically unsatd. groups at both terminals. The terminal unsatd. groups of the prepolymer and a vinyl compd. component contg. at least one (meth)acrylic ester are subjected to polymn. to give an org.-solvent-soluble acryl-urethane copolymer. Pref. the (meth)acrylic ester is one having an active hydrogen group capable of undergoing cross-linking reaction with a polyisocyanate compd. (e.g. 2- hydroxyethyl acrylate).

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention is applicable to a paint for building exterior which is rich in flexibility, tough and durable, and is hardly affected by temperature and maintains its properties even in a low temperature region. The present invention relates to an organic solvent-soluble acrylic / urethane copolymer suitable for a binder and a method for producing the same.

[0002]

2. Description of the Related Art Conventionally, acrylic / urethane copolymers having the properties of acrylic resin such as gloss and durability and the properties of polyurethane resin such as flexibility and toughness have been used in the field of paints, especially in the environment of the environment. For example, when the coating substrate is concrete or mortar, it has been used as a binder in paints for building exteriors which need to be able to adapt to cracks generated in them, or expansion, expansion and contraction caused by changes in external temperature. One of the typical ones is to make acrylic resin and urethane resin (prepolymer) separately, that is, acrylic resin has multiple hydroxyl groups in one molecule, and based on this, it is colored with pigment and paint The urethane resin does not form a curing agent with a polyisocyanate having a plurality of isocyanate groups capable of reacting with the hydroxyl groups possessed by the acrylic resin in one molecule and binding with the urethane group, or an isocyanate group-terminated polyurethane prepolymer. A binder for a so-called two-pack type paint, in which both the main agent and the curing agent are mixed at the time of use, and after application, the hydroxyl group of the acrylic resin and the isocyanate group of the polyurethane resin react and bond to form a thermosetting crosslinked resin coating film. Resin. In addition, a low-molecular-weight urethane oligomer having an ethylenically unsaturated double bond group at both ends is dissolved in a vinyl monomer containing a (meth) acrylic acid ester, and a crosslinking reaction is caused by irradiation with energy rays to produce a thermosetting acrylic. -There is also a method of forming a urethane copolymer, which is applied to various fields such as surface treatment agents and printing ink binders in addition to various paints.

[0003] These acrylic / urethane copolymers have the respective characteristics of acrylic resin and polyurethane resin, but each is a two-part mixture type in which a main agent and a curing agent are mixed immediately before use. Operations such as manufacturing, coating, and adjustment during use are extremely complicated. Much work has been done to improve and simplify these. For example, various studies have been made as to whether an acrylic resin and a polyurethane resin are separately produced, and both properties can be added by blending them.

Further, an acrylic segment and a polyurethane segment can be chemically bonded to be used as a one-pack type.
Acrylic / urethane copolymerization methods such as acrylic / urethane graft copolymers are also being studied. As an acrylic / urethane graft copolymer, for example, Polym. , Bu
ll. , 8, 239 (1982) discloses a method of synthesizing an acrylic macromonomer having two hydroxyl groups at one molecular end and using this as one of the components to produce a polyurethane. Specifically, thioglycerin (having one mercapto group and two hydroxyl groups) is used as a chain transfer agent, and a radical polymerization reaction of (meth) acrylates is performed in the presence of thioglycerin. Then, an acrylic resin having a hydroxyl group is prepared, and then this is polyadded with a urethane prepolymer having isocyanate groups at both ends to obtain an acrylic graft type segmented polyurethane. The copolymer obtained here has both characteristics of an acrylic resin and a polyurethane resin. As a recent technique belonging to this method, Japanese Patent Application Laid-Open No. 6-100653 discloses an acrylic graft polyurethane compound similar to that described above and a method for producing the same.

[0005]

However, in the above-described method of simply blending an acrylic resin and a polyurethane resin, good results have not been obtained because both resins are originally poorly compatible. In addition, although various studies have been made as a measure for improving the problem, such as use of a special plasticizer and a compatibilizer, and other attempts to use an alloy, no satisfactory results have been obtained. On the other hand, the use of an acrylic / urethane graft copolymer solves the problem of compatibility.However, the acrylic graft polyurethane compound obtained by these methods is susceptible to thermal effects because it is thermoplastic, and has a low flexibility at room temperature. Although shown, it has the disadvantage of crystallization and losing extensibility in the low temperature range of 0 ° C. or lower, and is not suitable for use in places requiring flexibility even in the low temperature range. The object of the present invention is to be applied to a building exterior paint that requires flexibility, toughness, and durability, and is suitable for a paint binder that is hardly affected by temperature and retains its properties even in a low temperature range. An object of the present invention is to provide an acrylic / urethane copolymer soluble in an organic solvent and a method for producing the same.

[0006]

Means for Solving the Problems The present inventors have made various studies to overcome this disadvantage, and as a result, have reached the present invention. In the prior art, an acrylic / urethane copolymer having a three-dimensional cross-linked structure has been used only for two-pack type paints because of its property of being a thermosetting resin that is insoluble in an organic solvent and cannot be processed. However,
The present inventors, when increasing the molecular weight of the urethane oligomer having an ethylenically unsaturated double bond at both ends, the cross-linking interval of the acrylic / urethane copolymer obtained to that extent increases, and the molecular structure becomes larger. The present inventors have found that an acrylic-urethane copolymer that is gradually shifted from a three-dimensional structure to a two-dimensional structure (a network structure) and is finally soluble in an organic solvent is obtained, and the present invention has been completed. That is, the present invention provides an acrylic polymer obtained by polymerizing a vinyl-based monomer containing at least a (meth) acrylate ester on a high-molecular linear polyurethane having an ethylenically unsaturated double bond group at both ends. A urethane copolymer and a method for producing the same. Here, if the molecular weight of the high-molecular-weight linear polyurethane prepolymer having an ethylenically unsaturated double bond group at both ends is less than 10,000, it may gel during a copolymerization reaction with a vinyl monomer, If the molecular weight is 100,000 or more, the urethane segment may be hardened under the influence of crystallization in a low temperature range. Therefore, the molecular weight is preferably in the range of 10,000 to 100,000. And while the acrylic / urethane copolymer obtained by the present invention is a resin soluble in an organic solvent, the resin film formed therefrom is less affected by heat, and in a low temperature range of -5 ° C or less. It also has sufficient extensibility and strength, and can be used as it is (as a one-pack type) for paints for building exterior use.

Further, the acrylic / urethane copolymer of the present invention uses a small amount of a (meth) acrylic acid ester containing an active hydrogen group as a (meth) acrylic acid ester monomer during (meth) acrylic acid ester polymerization. Acrylic / urethane copolymers containing active hydrogen groups are made, and a small amount of a polyisocyanate compound is added as a curing agent during use, resulting in a thermosetting resin with a three-dimensional structure and improved chemical and solvent resistance. It can also be done. In this case, the two-component mixture type is used, but the amount of hydroxyl groups contained in the acrylic / urethane copolymer is small compared to the conventional product, so the amount of polyisocyanate used as a curing agent is also small, and this The polyisocyanate curing agent does not have the difficulty of urethane prepolymerization as in the conventional method.
The active hydrogen group-containing acrylic / urethane copolymer can be used as a one-pack type without adding a polyisocyanate.

The copolymer of the present invention, a method for producing the same, and a coating composition containing the same are as follows. (1) An organic solvent obtained by reacting at least one vinyl compound containing a (meth) acrylic ester with a high-molecular linear polyurethane prepolymer having an ethylenically unsaturated double bond group at both terminals. Soluble acrylic / urethane copolymer. (2) The acrylic resin according to the above (1), wherein the molecular weight of the high-molecular linear polyurethane prepolymer is 10,000 to 100,000.
Urethane copolymer. (3) The acrylic / urethane copolymer according to the above (1) or (2), which contains, as a (meth) acrylate, a (meth) acrylate containing an active hydrogen group capable of undergoing a crosslinking reaction with a polyisocyanate compound.

(4) A polymerization reaction between an ethylenically unsaturated double bond group at both ends of a high-molecular-weight linear polyurethane prepolymer and a vinyl compound containing at least one (meth) acrylate. A method for producing an organic solvent-soluble acrylic / urethane copolymer. (5) The method for producing an acrylic / urethane copolymer according to the above (4), wherein the (meth) acrylic acid ester contains an active hydrogen group-containing (meth) acrylic acid ester capable of undergoing a crosslinking reaction with a polyisocyanate compound.

(6) A one-pack type coating composition containing the acrylic / urethane copolymer soluble in the organic solvent of the above (1). (7) A two-pack coating composition comprising the organic solvent-soluble acrylic / urethane copolymer of (3) and a polyisocyanate compound.

[0011]

BEST MODE FOR CARRYING OUT THE INVENTION The copolymer of the present invention is produced by preparing a linear polyurethane prepolymer having an ethylenically unsaturated double bond at both terminals and, in the presence of the prepolymer, a (meth) acrylate ester. And the polymerization of a vinyl compound containing at least. In order to produce a polyurethane prepolymer having an ethylenically unsaturated double bond group, which is the first step, first, a linear urethane segment having an NCO terminal and a molecular weight of 10,000 to 100,000 is produced. Next, a theoretical amount of a (meth) acrylic ester containing one hydroxyl group capable of reacting with the NCO at both ends is added. The urethane segment is prepared according to a conventional method, that is, a long-chain diol, a short-chain glycol, a chain extender is used in some cases, and a stoichiometric amount of an organic diisocyanate is added thereto according to the molecular weight of a copolymer to be produced. react. This reaction is carried out in an inert organic solvent, and a metal catalyst such as dibutyltin dilaurate or a tertiary amine catalyst such as triethylamine, which is commonly used in the production of polyurethane, can be used as a catalyst for accelerating the reaction. In the second step, a vinyl-based monomer containing at least (meth) acrylates is added to a polyurethane prepolymer having an ethylenically unsaturated double bond group at both ends synthesized in the first step, and polymerization is carried out in an organic solvent. Make acrylic / urethane copolymer. This reaction may be carried out by a radical polymerization carried out with the addition of a polymerization initiator according to a conventional method of acrylic resin polymerization. At this time, a mercaptan group-containing compound may be appropriately added to the reaction solution as a chain transfer agent to adjust the degree of polymerization of acrylic.

The organic diisocyanate is, for example, 2,4-tolylene diisocyanate, 2,2
6-tolylene diisocyanate, xylene-1,4-diisocyanate, xylene-1,3-diisocyanate, 4,4'-diphenylmethane diisocyanate,
2,4'-diphenylmethane diisocyanate, 4,
4'-diphenyl ether diisocyanate, 2-nitrodiphenyl-4,4'-diisocyanate, 2,2 '
-Diphenylpropane-4,4'-diisocyanate,
3,3'-dimethyldiphenylmethane-4,4'-diisocyanate, 4,4'-diphenylpropane diisocyanate, m-phenylene diisocyanate, p-phenylene diisocyanate, naphthylene-1,4-diisocyanate, naphthylene-1,5-diisocyanate,
Aromatic diisocyanates such as 3,3'-dimethoxydiphenyl-4,4'-diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate,
Aliphatic diisocyanates such as lysine diisocyanate,
Alicyclic diisocyanates such as isophorone diisocyanate, hydrogenated tolylene diisocyanate, hydrogenated xylene diisocyanate, and hydrogenated diphenylmethane diisocyanate.

As the long-chain diol, those known in the polyurethane industry are used, and examples thereof include polyester diol, polyester amide diol, polyether diol, polyester polyether diol, and polycarbonate diol. Specifically, for example, succinic acid, adipic acid, sebacic acid, azelaic acid, dimer acid, terephthalic acid, isophthalic acid, hexahydroterephthalic acid, dicarboxylic acids such as hexahydroisophthalic acid, acid esters or acid anhydrides thereof. ,
Ethylene glycol, 1,3-propylene glycol,
1,2-propylene glycol, 1,4-butylene glycol, 1,5-pentane glycol, 1,6-hexane glycol, 3-methyl-1,5-pentane glycol, neopentyl glycol, 1,8-octane glycol, 1,9-nonanediol, diethylene glycol, cyclohexane-1,4-diol, cyclohexane-1,4-dimethanol, diol dimer acid, trimethylolpropane, glycerin, hexanetriol, quadrol, or bisphenol A ethylene oxide or propylene oxide addition Such as glycol, or diamines such as hexamethylenediamine, xylenediamine, isophoronediamine, monoethanolamine, isopropanoltriamine, triamine or amino alcohol, etc. Germany, or polyester polyols obtained by dehydration condensation reaction of a mixture thereof, polyester amides polyol. Further, ε-caprolactone, alkyl-substituted ε-caprolactone, δ-
Examples include polyester polyols such as lactone-based polyester polyols obtained by ring-opening polymerization of cyclic ester (ie, lactone) monomers such as valerolactone and alkyl-substituted δ-valerolactone. Examples of the polyether polyol include polyethylene glycol,
Examples thereof include polypropylene ether polyol and polytetramethylene ether polyol. Polyether ・
Examples of the ester polyol include those produced from the above-mentioned polyether polyol and the above-mentioned dicarboxylic acid or acid anhydride. Examples of the polycarbonate polyol include 1,4-butylene glycol,
Examples thereof include those obtained from the reaction of 5-pentane glycol, hexane glycol, 3-methyl-1,5-pentanediol, 1,4-cyclohexane dimethanol or the like with diethyl carbonate or diphenyl carbonate. Specific products include N-980 and N-981 manufactured by Nippon Polyurethane. In addition, urea resins, melamine resins, epoxy resins, polyester resins, acrylic resins, polyvinyl alcohols, and the like are also generally known in the polyurethane industry and include two or more active hydrogen groups as long-chain polyols or a part thereof. Can be used as The molecular weight of these long-chain polyols is preferably in the range of 350 to 8000. When the molecular weight is less than 350, the urethane component cannot exhibit flexibility, and when the molecular weight exceeds 8,000, the urethane group concentration of the copolymer decreases. Poor solvent resistance.

The short-chain glycols include the monomolecular diols and triols mentioned as the raw materials for the long-chain polyols, ie, ethylene glycol, 1,3-propylene glycol, 1,2-propylene glycol, 1,4-butylene glycol, , 5-pentane glycol, 1,6
-Hexane glycol, 3-methyl-1,5-pentane glycol, neopentyl glycol, 1,8-octane glycol, 1,9-nonanediol, diethylene glycol, cyclohexane-1,4-diol, cyclohexane-1,4-di Methanol, dimer acid diol, trimethylolpropane, glycerin, hexanetriol, quadrol or bisphenol A ethylene oxide or propylene oxide adducts can also be used.

Examples of the chain extender include monomolecular diamines such as hydrazine, ethylenediamine and hexamethylenediamine; aromatic diamines such as triamine, toluenediamine and diaminodiphenylmethane; alicyclic diamines such as isophoronediamine; Examples include polyether polyamines that have become amino groups. As the amino alcohol, monoethanolamine,
Examples thereof include diethanolamine, triethanolamine, and N-methyldiethanolamine.

Here, the ratio of the long-chain diol to the short-chain glycol is such that the long-chain diol / short-chain glycol = 1 by weight.
In the range of 00/0 to 70/30, preferably 100 /
0 to 80/20.

The molecular weight of the polyurethane segment is adjusted by appropriately changing the ratio of the total number of active hydrogens contained in the long-chain diol, short-chain glycol, chain extender and the like used to the number of moles of isocyanate groups reacted therewith. . The preferred molecular weight is from 20,000 to 50,000.

Next, in a second step of copolymerizing the vinyl compound, at least an acrylic ester and / or a methacrylic ester is added to the urethane prepolymer having an unsaturated double bond group at both ends produced in the first step. The added vinyl compound is added, and a diazo compound such as azobisisobutyronitrile (AIBN) or a peroxide such as benzoyl peroxide or Kayaester-O (Chemical Drug Akzo) is used as a radical generator. And radical polymerization is performed in a usual organic solvent. On this occasion,
Unsaturated double bonds at both ends of the urethane prepolymer easily generate radicals, and a chain polymerization reaction of the vinyl compound is carried out from the radicals to generate an acrylic urethane copolymer. The degree of polymerization is adjusted by appropriately adding a compound containing a mercaptan group to the reaction solution as a chain transfer agent. The reaction is desirably carried out by a method in which an initiator is added to a mixture of a urethane prepolymer having an unsaturated double bond at both ends and a vinyl compound, and the mixture is added dropwise to the reaction system, but is not limited thereto. The amounts of the urethane prepolymer and the vinyl compound are expressed in a weight ratio of the urethane prepolymer /
Vinyl compound = 30 in the range of 20/80 to 80/20
/ 70-70 / 30 is particularly preferred. The amount of the initiator is preferably in the range of 0.5 to 2% based on the weight of the vinyl compound. As the solvent, a general aromatic hydrocarbon solvent such as toluene or xylene is used, but the solvent is not limited.

The acrylate used in the present invention may be methacrylate, such as methyl acrylate, ethyl acrylate, n- or iso-butyl acrylate, hexyl acrylate, cyclohexyl acrylate, methyl methacrylate, ethyl methacrylate, n- or iso- Butyl methacrylate, hexyl methacrylate, cyclohexyl methacrylate, and the like. If necessary, long-chain alkyl acrylates and long-chain alkyl methacrylates such as lauryl acrylate, stearyl acrylate, lauryl methacrylate, and stearyl methacrylate can also be used in combination. Other vinyl compounds that can be used in combination include styrene, chlorostyrene, methyl styrene, and the like. Needless to say, the vinyl compound may be only an acrylic ester and / or a methacrylic ester. Further, as the (meth) acrylic acid ester, 2-hydroxyethyl acrylate, 2-hydroxyethyl methacrylate, aminoethyl methacrylate containing an active hydrogen group, FA-1, FA-2, FA-3, and FM- manufactured by Daicel Chemical Industries, Ltd. 1, FM-2
If an active hydrogen group-containing acrylate or an active hydrogen group-containing methacrylate such as 2-hydroxyethyl acrylate or 2-hydroxymethacrylate caprolactone adduct is used, a hydroxyl group, an imino group, an amino group, a carboxyl group, etc. An acrylic / urethane copolymer having an active hydrogen group capable of reacting with an isocyanate group is obtained. The preferred amount of the active hydrogen group-containing (meth) acrylic acid ester is 2 to 20% by weight, more preferably 10 to 20% by weight, based on the total solid content of the acrylic / urethane copolymer. If the amount is more than 20% by weight, problems such as deterioration of the solubility of the copolymer in an organic solvent, clouding, and increase in viscosity occur. Furthermore, since the copolymer is precipitated during the reaction, the molecular weight cannot be increased, and physical properties as a high molecular weight acrylic / urethane copolymer cannot be expected. This copolymer can be cross-linked with an organic polyisocyanate curing agent to form a tougher coating film which is insoluble and infusible in a solvent. As the organic polyisocyanate curing agent, those having an average number of functional groups of 2.5 to 4.0 are preferable, and examples thereof include Coronate L, Coronate HL, and Coronate HX manufactured by Nippon Polyurethane. The curing agent is used in an amount of 1 to 10 parts by weight based on 100 parts by weight of the active hydrogen group-containing acrylic urethane copolymer.

[0020]

EXAMPLES Hereinafter, the present invention will be described in more detail with reference to Examples and Comparative Examples, but the present invention is not limited thereto. In Examples and Comparative Examples, “parts” and “%” are all based on weight unless otherwise specified. Example 1 In a reaction vessel equipped with a stirrer, thermometer, cooler and nitrogen gas inlet tube, 86.6 parts of polycaprolactone diol having a molecular weight of 1250 (manufactured by Daicel Chemical), 161.7 parts of polypropylene glycol having a molecular weight of 1000, and hexamethylene diisocyanate ( 40.8 parts of Nippon Polyurethane), 75 parts of toluene and 0.05 parts of dibutyltin dilaurate were charged as a catalyst and reacted at 80 ° C. under a nitrogen atmosphere. When the isocyanate (NCO) concentration reached the theoretical amount, 2- 10.9 parts of FM-3 (manufactured by Daicel Chemical Industries, Ltd.), which is a caprolactone adduct of hydroxymethacrylate, and 125 g of toluene were added and reacted until the NCO at both ends of the urethane prepolymer disappeared.
To obtain 500 parts of a linear urethane prepolymer having unsaturated double bonds at both ends. Next, methyl methacrylate 129.6 was added to 200 parts of the urethane prepolymer solution.
Parts, 30 parts of styrene, 18.9 parts of FM-3, 1.5 parts of acrylic acid, and 220 parts of toluene were added to prepare 600 parts of a mixed monomer. Of these, 300 parts are placed in a reaction vessel for performing a radical reaction and heated. Kayaester-O is used as a radical initiator in 300 parts of the remaining mixed monomer.
1.8 parts (manufactured by Kayaku Akzo) and 100 parts of toluene are added and mixed well. When the temperature of the mixed monomer in the reaction vessel reached 90 ° C., the mixed monomer containing the initiator was added dropwise over 3 hours. To further reduce residual monomers, toluene 100
Of Kayaester-O and 0.5 part of Kayaester-O was added dropwise over 1 hour. After completion of the dropping, heating was continued at 105 ± 5 ° C. for 3 hours to obtain a target acrylic urethane resin. This copolymer has a solid content of 37% and a viscosity of 7000 cP /
25 ° C., hydroxyl value 18.7 (in terms of solid content), acid value 4.
2 (in terms of solid content).

Examples 2 to 8 The reaction was carried out under the same conditions as in Example 1 except that the kind and the mixing ratio of the long-chain polyol, organic diisocyanate and the like were changed to obtain an acrylic urethane copolymer. Tables 1 and 2 summarize the composition and properties.

[Table 1]

[0022]

[Table 2]

Comparative Example 1 Toluene 250 was used as a solvent in the same reaction vessel as in Example 1.
After heating the mixture to 100 ° C under a nitrogen atmosphere,
A mixture of 5 parts of methyl methacrylate, 24 parts of butyl acrylate, 11 parts of α-thioglycerin and 5 parts of benzoyl peroxide was added dropwise over 3 hours. After completion of the dropwise addition, heating was continued at 110 ° C. for 3 hours to obtain an intended acrylic resin solution having two hydroxyl groups at the terminal. Next, 250 parts of this acrylic resin solution, molecular weight 10
44 parts of 3-methylpentane adipate diol of 00,
54 parts of polycaprolactone diol having a molecular weight of 1250 (manufactured by Daicel Chemical Industries, Ltd.), 0.1 part of dibutyltin dilaurate as a catalyst, and 125 parts of toluene as a reaction solvent were charged into the above reaction vessel, and the isocyanate content was 0.01% at 80 ° C. under a nitrogen atmosphere. Heating was continued until the temperature became below, to obtain an acrylic graft urethane copolymer. The solid content was 49.9% and the viscosity was 59000 cP / 25 ° C.

(Evaluation of Copolymer) The copolymers obtained in Examples 1 to 4 and Comparative Example 1 were subjected to centrifugal film formation with and without the addition of coronate HX (manufactured by Nippon Polyurethane) as a curing agent. Approximately 250μ at 60-100 ° C
Was prepared and punched out using a No. 2 dumbbell. As a test machine, an autograph AG-5000C manufactured by Shimadzu Corporation was used. The tensile conditions were a temperature of 20 ° C (65% humidity), 0 ° C, -20 ° C, a constant pulling speed of 200 m / m / min, and a 100% modulus. , Breaking strength and elongation were measured. -Breaking strength: Stress when the film breaks (unit is kg
f / cm ² ) ・ Elongation rate: All for the distance between chucks (60 m / m) (unit:% by length) These evaluation results are summarized in Table 3. In addition, the results in Table 3 show that when the copolymers of Examples 1 to 4 were used in a coating composition, they had excellent durability against repeated heating and cooling, and low-temperature properties such as elongation at the time of low adhesion. This shows that an excellent coating composition can be obtained.

[Table 3]

[0025]

As described above, according to the present invention, an acrylic resin which is suitable for a flexible, tough, and durable paint, is not easily affected by temperature, and maintains its properties even in a low temperature range.
Not only can a urethane copolymer be obtained and a method for producing a one-pack type acrylic urethane copolymer having the characteristics of a urethane resin and an acrylic resin be provided, but also a two-pack type can further provide weather resistance and solvent resistance. It has become possible to provide an acrylic urethane copolymer which is excellent in water resistance and a method for producing the same.

Claims (7)

[Claims] 1. An organic compound obtained by reacting a high-molecular-weight linear polyurethane prepolymer having an ethylenically unsaturated double bond group at both ends with a vinyl compound containing at least one (meth) acrylate. Solvent soluble acrylic
Urethane copolymer. 2. The acrylic / urethane copolymer according to claim 1, wherein the high molecular weight linear polyurethane prepolymer has a molecular weight of 10,000 to 100,000. 3. An active hydrogen group-containing (meth) acrylate capable of undergoing a cross-linking reaction with a polyisocyanate compound as the (meth) acrylate.
Or the acrylic / urethane copolymer according to claim 2. 4. A polymer linear polyurethane prepolymer having at least one terminal ethylenically unsaturated double bond group and
A method for producing an organic solvent-soluble acrylic / urethane copolymer, which comprises polymerizing a vinyl compound containing a kind of (meth) acrylic ester. 5. An active hydrogen group-containing (meth) acrylate which is capable of undergoing a cross-linking reaction with a polyisocyanate compound as the (meth) acrylate.
The method for producing the acrylic / urethane copolymer according to the above. 6. The acrylic solvent soluble in an organic solvent according to claim 1.
A one-pack coating composition containing a urethane copolymer. 7. The organic solvent-soluble acrylic according to claim 3,
A two-pack coating composition containing a urethane copolymer and a polyisocyanate compound.