JP2787309B2 - Method for producing non-aqueous dispersion type resin for paint - Google Patents

Description

The present invention relates to a novel method for producing a non-aqueous dispersion for paints,
More specifically, a specific polymer azo initiator having both one or more azo groups and two or more polycondensation compound residues in the molecule is used as a dispersion stabilizer, and an aliphatic hydrocarbon is essential. The present invention relates to a method for producing a dispersion of polymer particles, which is useful as a coating material, comprising polymerizing monomers such that a copolymer becomes insoluble in a specific organic solvent.

[Conventional technology]

In recent years, this type of non-aqueous dispersion type resin has relatively little adverse effect on the environment due to the use of a non-polar weak solvent, exhibits a thixotropy in viscosity behavior due to its particle system, and has a thick coating. Because it has features such as simplicity and other features, it also offers better performance than conventional solvent-type resins and emulsion-type resins. Such as painting the outer panel,
It has begun to be used in various fields.

By the way, as a conventional method of preparing a non-aqueous dispersion type resin,
In a solvent in which a dispersing resin is dissolved, a monomer is soluble in the solvent, but a polymer obtained from the monomer is insoluble. Although the method of polymerizing and making particles is common,
As the form of the polymer in the case of following such a method, a polymerization active site is generated in a part of the molecule of the dispersion resin incorporated in the polymer, that is, the dispersion stabilizer, and the organic solvent is A very small portion of the vinyl monomer, which is obtained as an insoluble new polymer (hereinafter, referred to as an insoluble polymer), reacts with the polymerization active site to form a so-called soluble polymer based on the dispersion stabilizer. A block copolymer or a graft copolymer consisting of a polymer portion and an insoluble polymer portion based on the vinyl monomer is formed, and at the same time, a large amount of the copolymer is subjected to the polymerization reaction. The vinyl monomer does not take part in such block copolymerization or graft copolymerization, but undergoes homopolymerization to form an insoluble polymer, and takes a mixed form of these polymers. Is

Such conventional non-aqueous polymer dispersions, first,
The content of the above-mentioned block copolymer or graft copolymer having good dispersion stability is low, and the content of the insoluble polymer obtained by the above-mentioned homopolymerization is high. The polymer is merely dispersed in an organic solvent or a so-called organic liquid containing the solvent by a physical secondary bond with a block copolymer or a graft copolymer. The dispersion has a problem that dispersion stability is poor.

In particular, when the non-aqueous polymer dispersion obtained as described above is used as a coating film-forming component, there is a more serious problem.

That is, as described above, the block copolymer or the graft copolymer and the insoluble polymer, unless a strong secondary bond is achieved by physical intermolecular force, from where dispersion stability cannot be maintained, As the vinyl monomer to be used for forming the polymer particles, usable types are extremely limited, and a monomer which can be a highly polar rigid polymer must be selected.

However, a coating film obtained from a non-aqueous polymer dispersion prepared under such restrictions cannot be uniform because the dispersion itself does not sufficiently melt and flow.

In addition, such a non-aqueous polymer dispersion, due to the high shearing force applied during the pigment dispersion, insoluble polymer coagulates and precipitates, a polar solvent having strong dissolving power for polymer particles, a plasticizer, etc. When added, the dispersion stability during storage becomes extremely poor, and there is a danger of eventually gelling or coagulating and sedimenting.

In order to solve this problem, the dispersion stabilizer is used to increase the concentration of the polymerization active site of the dispersing resin. However, according to such a method, since the block copolymer or the graft copolymer is contained in a large amount, as the insoluble polymer portion, a softer and less polar polymer portion is formed. The effect is that the substances are stably dispersed, but on the other hand, the control of the polymerization reaction becomes extremely difficult, and the reaction proceeds smoothly even if it gels during the reaction or it does not go to that point. There were manufacturing problems such as not progressing.

Apart from that, recently, a technique of stabilizing dispersion by performing block copolymerization or graft copolymerization using a special peroxide catalyst called polymeric peroxide has been proposed, but such polymeric peroxide has been proposed. There remains a problem with its own manufacturing peculiarities and dangers.

[Problems to be solved by the invention]

As described above, the non-aqueous polymer dispersions of the class that have been practically used so far have a very narrow selection range of vinyl monomers capable of forming an insoluble polymer, and , Dispersion stability itself has a problem,
After all, a satisfactory film-forming polymer has not yet been obtained, and at present there is a great demand for technical improvement.

[Means for solving the problem]

However, the present inventors have conducted intensive studies in view of the existence of various disadvantages in the prior art as described above, and as a result, have one or more azo groups and two or more polyol compound residues in the molecule. Production of a new form of non-aqueous polymer dispersion for coatings, which eliminates all of the disadvantages of conventional non-aqueous polymer dispersions by a novel method using a specific, so-called polymeric azo initiator The present invention has been completed by a method, that is, a method for producing a dispersion of a non-aqueous dispersion type resin for paint.

That is, the present invention relates to an organic solvent containing an aliphatic hydrocarbon as an essential component, In the presence of 5 to 70 parts by weight of the compound (B) having one or more structural units per molecule in the molecule, the organic solvent (A)
On the other hand, although each monomer is soluble,
The polymer of the monomer is obtained by polymerizing 95 to 30 parts by weight of the polymerizable unsaturated monomer (C) which becomes insoluble, has a uniform particle size, and is excellent in dispersion stability for paints. An object of the present invention is to provide a method for producing a non-aqueous dispersion type resin.

Here, the compound (B) having at least one structural unit represented by the above-mentioned formula [I] in one molecule is described in, for example, “Polymer's Journal”, Vol. 33, No. 3, 131-140. It is prepared by applying a low-temperature condensation reaction as described on page (issued in 1976).

That is, first, 2,2'-azobis (2-methylpropionic acid), 4,4'-azobis (4-cyanopropionic acid) or 4,4'-azobis (4-cyanopentanoic acid)
Thionyl chloride is reacted with a terminal carboxy group compound containing an azo group in the molecule in the low temperature range of 0 to 20 ° C. to form an acid chloride product, followed by performing a predetermined purification. The obtained azo group-containing acid chloride and the active hydrogen-containing compound are subjected to a condensation reaction at 0 to 25 ° C. in the presence of a tertiary amine such as triethylamine, and then subjected to predetermined purification such as washing with water. It is obtained by vacuum drying.

The preparation of the compound (B) will be described in further detail. R ₁ in the structural unit represented by the general formula [I] is, for example, an aliphatic group having a substituted or unsubstituted alkylene group of C _{4 to} C _22. dihydric alcohols, diols having a substituted or unsubstituted cyclohexylene group, a polyester having a C ₄ -C ₂₂ comprising substituted or ester diols having a non-substituted alkyl group, C ₄ -C ₂₂ comprising substituted or unsubstituted alkylene group A polyol, a polyester polyol having a substituted or unsubstituted cyclohexylene group,
It represents a residue after various compounds such as a hydroxyl group-containing vinyl copolymer are ester-bonded. (However, the polyester polyol and the hydroxyl group-containing vinyl copolymer partially contain a substituted or unsubstituted phenylene group. Good).

Here, the aliphatic dihydric alcohol includes 1,4-butylene glycol, 1,6-hexanediol, diethylene glycol, dipropylene glycol,
Representative examples include neopentyl glycol, triethylene glycol and lauryl alcohol.

As the diol having a substituted or unsubstituted cyclohexylene group described above, consisting of C ₃ or more cycloalkyl group or substituted cycloalkyl group, for example, like cyclohexanedimethanol and hydrogenated bisphenol A typical ones is there.

Further, as the above-mentioned ester diols or various polyester polyols, as described above, aliphatic dihydric alcohols or cyclohexylene group-containing diols may be used, with aliphatic carboxylic acids and / or alicyclic carboxylic acids as main components. A compound having a number average molecular weight in the range of 200 to 8,000, which is obtained by condensation polymerization with the acid component compound described above, includes a known aliphatic monohydric alcohol, a fatty acid, isophthalic acid or phthalic anhydride. Of course, aromatic carboxylic acids such as acids or anhydrides thereof can be partially used in combination.

Representative examples of the above aliphatic carboxylic acids include adipic acid, azelaic acid and sebacic acid.
On the other hand, examples of the alicyclic carboxylic acid include cyclohexanedicarboxylic acid and the like, and an anhydride of an alicyclic carboxylic acid such as hexahydrophthalic anhydride and tetrahydrophthalic anhydride is also a typical example. Things.

1 Further, as the hydroxyl group-containing vinyl copolymer described above, mainly composed of (meth) acrylic acid ester having a C ₄ or higher alkyl, in the range of number average molecular weight is 800 to 20,000, in one molecule Examples thereof include compounds containing at least two hydroxyl groups, for example, a hydroxyl-containing chain transfer agent such as 2-mercaptoethanol or octyl thioglycolate, and a hydroxyl-containing polymerization initiator such as azobiscyanopropanol or azobiscyanopentanol. Is obtained by polymerizing a vinyl monomer as shown in Table 1 in the presence of.

Organic solvent (A) particles of the dispersed polymer in which the essential component an aliphatic hydrocarbon solvent, i.e. to obtain dispersed particles, inevitably has a C ₄ or higher alkyl group-containing (meth) acrylic acid ester In order to perform the method of the present invention and obtain a uniform and stable dispersion which meets the purpose of the present invention, so that it is necessary to select a monomer having High-molecular-weight azo initiator which is sufficiently soluble in a specific organic solvent to be obtained, especially the above-mentioned general formula [I]
The structure of R ₁ itself in the structural unit must be designed.

If these conditions even be satisfied, the component compounds constituting the R ₁ is particularly, but not limited.

On the other hand, R ₂ in the structural unit represented by the aforementioned general formula [I]
Although one in which an alkylene group containing an alkylene group or a cyano group, for use as a component compound to constitute the R ₂ is a compound having both an azo group and a carboxyl group in one molecule, Representative examples of such compounds are 2,2'-azobis (2-methylpropionic acid) and 4,4'-azobis (4-cyanopropionic acid)
Or an azo group-containing terminal carboxyl group compound as described above, represented by 4,4'-azobis (4-cyanopentanoic acid) and the like.

In the presence of the compound (B) obtained as described above,
The polymerizable unsaturated monomer (C) polymerized in the organic liquid will be described in detail. The monomer (C) used in carrying out the method of the present invention is dissolved once in the organic liquid. The polymerization is started by the compound (B), a so-called high-molecular azo initiator, that is, from the point where block polymerization is started and particles are formed, the organic solvent (A) as an organic liquid for polymerization is mixed with the organic solvent (A). There is a correlation with the monomer (C), and Table 1 itself shows such a relationship.

However, the present invention is by no means limited to only those listed in the table.

Representative examples of the polymerizable unsaturated monomer (C) used in carrying out the method of the present invention include methyl (meth) acrylate, ethyl (meth) acrylate, (meth)
Lower alkyl (meth) acrylates such as n-propyl acrylate, isopropyl (meth) acrylate or glycidyl (meth) acrylate; n-butyl (meth) acrylate, isobutyl (meth) acrylate, (meth) T-butyl acrylate, n-hexyl (meth) acrylate, cyclohexyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, octyl (meth) acrylate, lauryl (meth) acrylate or (meth) ) Higher alkyl (meth) acrylates such as stearyl acrylate; lower aliphatic vinyl esters such as vinyl acetate or vinyl propionate; vinyl butyrate, vinyl caproate, vinyl 2-ethylhexanoate, vinyl laurate, vinyl stearate or " Beoba "(Singapore Le Co., such as higher aliphatic vinyl esters of vinyl ester) branched fatty acid; styrene, such as vinyl toluene or vinyl pyrrolidone aromatic vinyl monomer; (meth) acrylamide, N-
Amide group-containing vinyl monomers such as methylol (meth) acrylamide or N-methoxymethyl (meth) acrylamide; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate or allyl alcohol Hydroxyl-containing vinyl monomers;
(Meth) acrylic acid, crotonic acid, itaconic acid, maleic acid-containing vinyl monomer such as maleic acid or fumaric acid; ethylene anhydride, phthalic anhydride or dodecenyl succinic anhydride-containing monomer; , Butadiene, vinyl chloride, vinyldene chloride, (meth) acrylonitrile, mono-n-butyl fumarate, diethyl maleate or (meth) allyl glycidyl ether.

The above-mentioned glycidyl (meth) acrylate does not belong to lower alkyl (meth) acrylate, and the above-mentioned cyclohexyl (meth) acrylate does not belong to higher alkyl (meth) acrylate. Derivatives of (meth) acrylate are listed for convenience.

In addition, ethylene and propylene can be classified as α-olefins, and if (meth) acrylonitrile is regarded as a kind of fatty acid ester, it should be put together with the above-mentioned lower aliphatic vinyl ester into one group. Would be possible.

These polymerizable unsaturated monomers (C) may be used alone or in combination of two or more.

The organic solvent (A) used in carrying out the method for producing a non-aqueous dispersion resin for paint of the present invention refers to an organic liquid containing 50% by weight or more of an aliphatic hydrocarbon, With respect to the aliphatic hydrocarbon to be the main component of the organic liquid, dispersed particles, that is, in the block copolymer as dispersed polymer particles, respectively, to the extent that the insolubility of the insoluble polymer portion is not impaired. In addition, other organic solvents can be added to the aliphatic hydrocarbon to such an extent that the solubility of the soluble polymer portion is not impaired.

First, typical aliphatic hydrocarbons include n-hexane, n-heptane, n-octane, petroleum benzine, ligroin, mineral spirit, petroleum naphtha as listed in Table 1. Or kerosene, etc. Specifically, "Isoper E or G" (a product of Exxon Chemical Co., USA), "Loose" (a product of Ciel Co., Netherlands), "Naphtha No. 5 or 6" (Exxon, U.S.A.)・ Chemical products)
"IP Solvent 1620" (product of Idemitsu Petrochemical Co., Ltd.) or "White Sol" (product of Kyodo Petroleum Co., Ltd.).

Other organic solvents can be used together in an amount of less than 50% by weight based on these aliphatic hydrocarbons. Typical examples of such organic solvents include those listed in Table 1. , Esters, ketones, alcohols, alicyclic hydrocarbons or aromatic hydrocarbons.

The above-mentioned "loin" is a mixture of an aliphatic hydrocarbon as a main component and a small amount of an aromatic hydrocarbon.

Thus, the process of the present invention can be carried out in an organic solvent (A) containing an aliphatic hydrocarbon as a main component, in the presence of the compound (B) as described above, and various polymerizations as described above. To polymerize the unsaturated monomer (C),
In the presence of 5 to 70 parts by weight of the compound (B) having one or more structural units in one molecule as represented by the above general formula [I], an organic solvent containing an aliphatic hydrocarbon as a main component ( In contrast to A), a mixture of the polymerizable unsaturated monomer (C) and the organic solvent (A), in which the monomer is soluble but the polymer of the monomer becomes insoluble, is used. Block copolymerization of these compounds (B), the so-called high-molecular azo initiator, and the monomer (C), thereby producing a non-aqueous polymer dispersion, that is, a non-aqueous dispersion type resin dispersion. It is to get.

At this time, the respective sequences existing between the azo groups in the compound (B) through the block copolymerization reaction of the compound (B) and the monomer (C), that is, the above-mentioned general formula [I]
Each member constituting the R ₁ in the structural unit in shown is solubilized in an organic solvent (A), a copolymer from the monomer (C) is in the form incorporated into the particles.

Thus, there is no need to use a low molecular weight azo initiator or a peroxide catalyst as used in ordinary radical polymerization.

In carrying out the method of the present invention, the compound (B)
The use amount of 5 to 70 parts by weight, preferably 15 to 40 parts by weight is appropriate. If less than 5 parts by weight,
Since the reaction rate of the block copolymerization of the compound (B) with the polymerizable unsaturated monomer (C) becomes too low, sufficient dispersion stability cannot be expected. On the other hand, 70 parts by weight If the amount exceeds the above range, the particles cannot be sufficiently formed and the dispersion cannot be stabilized.

The temperature of the block copolymerization reaction performed in the presence of the compound (B) is preferably in the range of 60 to 140 ° C, and the reaction time is preferably in the range of 6 to 18 hours.

The amount of the organic solvent (A) used is such that the non-aqueous polymer dispersion, which is a dispersion of the obtained non-aqueous dispersion resin, preferably has a nonvolatile content of 30 to 70% by weight. Range, i.e. 70 in this non-aqueous polymer dispersion.
What is necessary is just an amount of the ratio occupying the range of 3030% by weight.

Thus, various additives such as other polymers, pigments or fillers can be added to the dispersion of the non-aqueous dispersion resin obtained by the method of the present invention, if necessary. As the union, butyl etherified melamine resin, butyl etherified benzoguanamine resin, butyl etherified urea resin, blocked polyisocyanate compound, aromatic, aliphatic or alicyclic polyepoxide, polyamide resin, or glycidyl group, carboxyl group, hydroxyl group, isocyanate A typical example is a vinyl resin containing a group, an alkoxy group or an N-methylolated amide group. As a curing agent with complementary functional groups, it becomes a thermosetting film-forming component Than it is.

As described above, the production method of the non-aqueous dispersion resin for paints of the present invention, compared to the conventional method, most of the produced polymer,
To provide a block copolymer consisting of a polymer portion soluble in an organic liquid (soluble polymer portion) and an insoluble polymer portion (insoluble polymer portion), such a block copolymer is used. It has a special feature that it can provide a non-aqueous polymer dispersion which is a dispersion of a non-aqueous dispersion type resin containing a high concentration, excellent in dispersion stability, and having a uniform particle size. Have.

〔Example〕

Next, the present invention will be described more specifically with reference to Examples and Examples. In the following, all parts and percentages are by weight unless otherwise specified.

Reference Example 1 [Preparation Example of Compound (B)] In a four-necked flask equipped with a thermometer, a stirrer and an air condenser, 224 parts of adipic acid, 236 parts of 1,6-hexanediol and 135 parts of octyl alcohol were placed. After the temperature was raised to 150 ° C, the temperature was gradually raised to 180 ° C over 2 hours, and further raised to 220 ° C over 2 hours. After the temperature reached 220 ° C, the temperature was maintained at the same temperature for 2 hours to continue the reaction. Then, the temperature was lowered to 50 ° C, 750 parts of chloroform was added, and the temperature was further lowered to 20 ° C or less.
Add 202 parts of triethylamine, add 200 parts of chloroform and 158.5 parts of 4,4'-azobiscyanopentanoic acid chloride.
Was added dropwise over 2 hours.

The reaction was allowed to continue for another 2 hours while keeping the temperature at 20 ° C or less, and then the triethylamine hydrochloride was washed off with water, filtered, and dried under vacuum to obtain a number average molecular weight (Mn).
1,800, and the average number of azo groups in one molecule is one,
A viscous solid target compound was obtained.

Reference Example 2 (same as above) After 453 parts of cyclohexanedicarboxylic acid and 640 parts of hydrogenated bisphenol A were charged, the hydroxyl value was 36.4 and ▲ ▼ was 3,080 in the same manner as in Reference Example 1.
A polyester resin having two hydroxyl groups in one molecule was obtained, and then the temperature was lowered to 60 ° C., and 1,500 parts of chloroform was added. The temperature was lowered to 20 ° C. with sufficient stirring, and 67.4 parts of triethylamine was obtained. Then, a mixture of 200 parts of chloroform and 105.7 parts of 4,4'-azobiscyanopentanoic acid chloride was added dropwise over 2 hours.

Thereafter, the same post-processing as in Reference Example 1 was performed, and
▼ was 18,200, and the average number of azo groups was 5.2, whereby a powdery target compound was obtained.

Reference Example 3 (same as above) In addition to 224 parts of adipic acid, 222 parts of phthalic anhydride,
In the same manner as in Reference Example 2, except that 500 parts of 1,6-hexanediol and 40 parts of dodecyl alcohol were also charged, ▲ ▼ was 2,500, and the hydroxyl value was 29.
Polyester resin No. 2 was obtained.

Then, 1,20 of chloroform was added to the polyester resin.
After adding 0 parts, the mixture was cooled to 20 ° C. with sufficient stirring. First, 45.7 parts of triethylamine was added, and then a mixed solution of 100 parts of chloroform and 71.7 parts of 4,4′-azobiscyanopentanoic acid chloride was added. It was dropped over time.

Thereafter, the same post-processing as in Reference Example 1 was performed, and
▼ was 1,300, and the average number of azo groups was 1.3.

Reference Example 4 (same as above) In an autoclave equipped with a dropping device, chloroform was added.
Charge 800 parts and raise the temperature to 130 ° C. From 600 parts of isobutyl methacrylate, 100 parts of styrene, 300 parts of stearyl methacrylate, 30 parts of 4,4′-azobiscyanopentanol and 200 parts of chloroform The resulting mixture was pressed in over 8 hours. After the completion of the injection, the temperature was maintained at the same temperature for 5 hours to continue the reaction, and the hydroxyl value was 8.3 and ▲
A solution of an acrylic copolymer having 6,800 was obtained.

Next, 14.9 parts of triethylamine was added thereto, and a mixed solution of 40 parts of chloroform and 23.3 parts of 4,4′-azobiscyanopentanoic acid chloride was added over 2 hours.
The solution was dropped while suppressing heat generation.

Thereafter, the same post-processing as in Reference Example 1 was performed, and
▼ was 22,000, and the solid target compound having an average number of azo groups of 35 was obtained.

Reference Example 5 (same as above) In an autoclave equipped with a dropping device, chloroform was added.
A mixture of 400 parts of isobutyl methacrylate, 590 parts of n-butyl methacrylate, 10 parts of acrylic acid, 30 parts of 2-mercaptoethanol and 200 parts of chloroform was charged with 800 parts and heated to 120 ° C. Was injected over 4 hours, the temperature was further maintained at the same temperature for 4 hours to continue the reaction, and the temperature was lowered to 20 ° C.

Then, the hydroxyl value thus obtained is 11.2, and
20 parts of triethylamine was added to the solution of the acrylic copolymer in which ▲ ▼ was 5,100, and a mixed solution consisting of 50 parts of chloroform and 31.07 parts of 4,4′-azobiscyanopentanoic acid chloride was added thereto over 2 hours. The mixture was added dropwise while cooling.

Thereafter, the same post-processing as in Reference Example 1 was performed, and
▼ was 9,600 and the average number of azo groups in one molecule was 1.7.

Example 1 In a reaction vessel equipped with a thermometer, a stirrer, and a reflux condenser, 100 parts of the compound obtained in Reference Example 1, 500 parts of a mineral turpentine, 250 parts of n-butyl acetate, and 250 parts of methyl methacrylate were added. 150 parts, 100 parts of ethyl acrylate, 40 parts of n-butyl methacrylate, 50 parts of 2-ethylhexyl acrylate and 2 parts of acrylic acid were charged, and the mixture was heated to 85 ° C. and reacted for 1 hour. After that, 500 copies of Isopar E,
A mixture consisting of 150 parts of the compound obtained in Reference Example 1, 300 parts of methyl methacrylate, 350 parts of ethyl acrylate and 8 parts of acrylic acid was added dropwise over 5 hours.

After the completion of the dropwise addition, the temperature was maintained at the same temperature for 8 hours to continue the polymerization reaction. As the polymerization reaction proceeded, the system became milky white.

The resin dispersion thus obtained has a nonvolatile content of 50.4%,
In addition, it was a non-aqueous dispersion type block copolymer resin dispersion having a Brookfield viscosity of 5.5 poise at 25 ° C.

Even after leaving it at 25 ° C. for 6 months, the dispersion was stable, and no sedimentation of particles, phase separation and change in viscosity were observed at all.

Example 2 Except for changing the raw material composition as shown in Table 2 and the polymerization temperature as defined in the same table, and changing the dropping time of the mixture such as monomer to 4 hours, respectively. ,
A block copolymerization reaction was carried out in the same manner as in Example 1 to obtain a dispersion of a non-aqueous dispersion type resin having performance each time the property values were as shown in the same table.

The property values and performance shown in the table were measured and evaluated in the following manner.

Average particle diameter: Measured using a "Submicron Particle Analyzer" Coaster Model N-4 manufactured by Coulter Electronics, USA.

Stability: The dispersion of each non-aqueous dispersion resin was placed in a screw tube, centrifuged at 2,000 rpm for 2 hours using a centrifuge, and the state of sedimentation was visually determined. When the height of the settled portion is less than 1 mm, it is indicated as "good", and when it is 1 mm or more, it is indicated as "bad".

Viscosity: This is indicated by the Kardner viscosity at 250 ° C.

[Effect of the Invention] As is clear from Table 2, the non-aqueous dispersion type resin obtained by the method of the present invention is known to be a dispersion having excellent dispersion stability.

That is, it is known that this non-aqueous dispersion resin gives an excellent non-aqueous polymer dispersion.

 ──────────────────────────────────────────────────続 き Continued on the front page (72) Inventor Susumu Nagai 3-5-5 Fujishirodai, Suita-shi, Osaka A27-209 (72) Inventor Akira Ueda 7-1-25, Nishitoriishi, Takaishi-shi, Osaka

Claims (2)

(57) [Claims] An organic solvent (A) containing an aliphatic hydrocarbon as an essential component, wherein In the presence of 5 to 70 parts by weight of the compound (B) having one or more structural units per molecule in the molecule, the organic solvent (A)
On the other hand, although each monomer is soluble,
A method for producing a non-aqueous dispersion resin for paints, characterized in that a polymer of the monomer is obtained by polymerizing 95 to 30 parts by weight of a polymerizable unsaturated monomer (C) which becomes insoluble. 2. The compound (B) comprises an acid chloride having an azo group, an aliphatic dihydric alcohol having a substituted or unsubstituted C ₄ -C ₂₂ alkylene group, a substituted or unsubstituted cyclohexylene group. diols having, C ₄ ~
Ester diols having a substituted or unsubstituted alkyl group comprising C _22, polyester polyols having a C ₄ -C ₂₂ comprising substituted or unsubstituted alkylene group, a polyester polyol having a substituted or unsubstituted cyclohexylene group or a hydroxyl group-containing vinyl, The production method according to claim 1, which is obtained by reacting with a copolymer.