JP3064385B2 - Thermosetting resin composition - Google Patents

Description

The present invention relates to a novel and useful thermosetting resin composition. More specifically, the present invention provides that
Comprising a low molecular weight compound having an oxo-1,3-dioxolan-4-yl group and a ring-opening catalyst thereof, or as an essential component, further comprising a carboxyl group and / or an acid anhydride group. Consisting of also containing a specific compound having, especially, a resin composition for a one-pack coating excellent in storage stability, acid resistance, weather resistance,
The present invention also relates to an extremely useful thermosetting resin composition which is excellent in coating appearance such as smoothness and the like.

Such a thermosetting resin composition of the present invention is mainly used in fields where acrylic polyol / melamine resin-based paints have conventionally been used, such as in automobile bodies and metal coatings. Things.

[Prior Art] In recent years, there has been a movement in the automobile industry, in particular, that places importance on the appearance of coating films.

However, the current aminoplasts have been used to solve the problem of so-called film appearance retention, such as deterioration after exposure, especially deterioration due to acid rain, as well as the finished appearance after painting and baking. It is no longer possible to satisfy such required performances with a paint that is a combination of a system curing agent and an acrylic polyol.

Among these movements, the combination of a polyol type resin and an isocyanate prepolymer, the combination of a silanol group-containing resin and an epoxy group-containing resin, the moisture curing by a trialkoxysilyl group, and the combination of a hydroxyl group-containing resin and an acid Various paints such as a curing system in combination with an anhydride group-containing resin are gradually being developed and studied.

However, among these coating systems, the polyol type resin / isocyanate prepolymer system has a short pot life and has a major drawback in terms of workability.

In addition, in both the curing system of the silanol group-containing resin and the epoxy group-containing resin and the moisture curing system of the trialkoxysilyl group, there is a difference in curability depending on the coating and baking conditions, and the appearance is satisfactory. It is not going.

[Problems to be Solved by the Invention] Further, in addition to such long-term storage stability and appearance of the coating film, a coating film resistant to acid rain can be obtained, mainly in the automobile industry, and is extremely useful. The current situation is that urgent development of a new curing system has been strongly demanded.

Therefore, the present inventors have attempted to eliminate or solve various drawbacks or problems in the prior art as described above,
In addition, the research has been started earnestly to meet the above-mentioned demands.

Therefore, the problem to be solved by the present invention is to be useful as a resin composition for one-pack coatings having excellent storage stability, and furthermore, itself, acid resistance and weather resistance, and smoothness. It is an object of the present invention to provide an extremely useful thermosetting resin composition which is excellent in the appearance of a coating film and the like.

Means for Solving the Problems The inventors of the present invention have conducted intensive studies with an aim on the problems to be solved by the invention as described above, and as a result, it has been found that at least two of the general formulas per molecule 2 represented by [I]
A 2-oxo-1,3-dioxolane having a low molecular weight compound having an oxo-1,3-dioxolan-4-yl group and having a molecular weight of 2,000 or less, and a quaternary ammonium salt and / or triphenylphosphine; A thermosetting resin composition containing a -4-yl group ring-opening catalyst, and wherein the content of the ring-opening catalyst is 0.1 to 20 parts by weight based on 100 parts by weight of the solid content of the low-molecular compound. , Alternatively, at least two of the general formula [I] in one molecule
And a low-molecular compound having a 2-oxo-1,3-dioxolan-4-yl group and a molecular weight of 2,000 or less, and at least two carboxyl groups and / or acid anhydrides in one molecule. 100% by weight of a compound containing a compound having a carboxyl group and / or an acid anhydride group, comprising a compound having a carboxyl group and / or an acid anhydride group, and a ring-opening catalyst for at least one 2-oxo-1,3-dioxolan-4-yl group. Thermosetting resin, wherein the content of the low-molecular compound is 0.5 to 1,000 parts by weight based on parts, and the content of the ring-opening catalyst is 0.1 to 20 parts by weight based on 100 parts by weight of the solid content of the low-molecular compound. The composition is
A one-pack type paint having excellent storage stability and hence good workability is provided.
The present invention has been completed by finding that a coating film having excellent weather resistance and coating film appearance is provided.

That is, the present invention requires, as essential components, at least two 2-oxo-1,3-dioxolane-formulas represented by the general formula [I] as described above, each in one molecule.
A low molecular weight compound having a 4-yl group and a molecular weight of 2,000 or less, and a ring-opening catalyst for a 2-oxo-1,3-dioxolan-4-yl group containing a quaternary ammonium salt and / or triphenylphosphine Or the low molecular weight compound and at least one kind of 2
A oxo-1,3-dioxolan-4-yl group ring-opening catalyst and a compound having at least two carboxyl groups and / or acid anhydride groups per molecule in a specific ratio. And a thermosetting resin composition.

In other words, the thermosetting resin composition of the present invention has such a 2
The oxo-1,3-dioxolan-4-yl group-containing low molecular weight compound is subjected to ring-opening polymerization or carboxyl group-containing and / or acid anhydride group-containing compound at a temperature of 90 to 140 ° C. in the presence of a specific catalyst. With a radical form of resin that is an essential skin-forming component that quickly reacts with radicals and decarbonation to form a strong coating, it has excellent storage stability and acid resistance. This is an extremely useful one that gives a one-pack type coating material that is also excellent.

Here, the molecule has at least two 2-oxo-1,3-dioxolan-4-yl groups in one molecule,
In addition, a low-molecular compound having a molecular weight of 2,000 or less is represented by the general formula A phthalic acid having a structure represented by
Hexahydro (anhydride) phthalic acid, tetrahydro (anhydride)
Phthalic acid, tetrachloro (anhydride) phthalic acid, hexachloro (anhydride) phthalic acid, tetrabromo (anhydride) phthalic acid,
Polycarboxylic acids such as trimellitic acid, "Hymic acid" (product of Hitachi Chemical Co., Ltd.), (anhydrous) succinic acid, (anhydride) maleic acid, fumaric acid, (anhydrous) itaconic acid, adipic acid or sebacic acid Those obtained by a dehydrochlorination reaction from acid acid chlorides, ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 1,6-hexanediol, -Methyl-
1,5-pentadiol, neopentyl glycol, cyclohexanedimethanol, dimethylolpropionic acid,
Polyethylene glycol, polypropylene glycol,
Polyhexamethylene glycol, trimethylolethane, trimethylolpropane, glycerin, pentaerythritol, polyhydric alcohol such as hydrogenated bisphenol A or bisphenol A, and isophorone diisocyanate, methylcyclo-hexane-2,4-diisocyanate, methylcyclohexane-2, 6-diisocyanate,
Addition reaction products with diisocyanate compounds such as 4,4'-methylenebis (cyclohexylisocyanate), 1,3-di (isocyanatomethyl) cyclohexane, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylcyclohexane diisocyanate, tolylene diisocyanate or xylene diisocyanate And those obtained by an addition reaction with a polyisocyanate compound.

Of course, it can also be obtained by activating the carboxyl group of the polycarboxylic acid with an activating agent and direct esterification with the hydroxyl compound represented by the aforementioned general formula [II].

Furthermore, those obtained by a dehydrochlorination reaction between the compound represented by the general formula [III] as described below and the polyvalent alcohol compound as described above are also included.

The compound represented by the formula (III) is generally obtained by reacting a thiol compound having a 1,2-dihydroxy structure with phosgene, such as glycerin, but the synthesis method is not particularly limited. Not something.

Furthermore, the 2-oxo-1,3-dioxolane-4
The yl group-containing low molecular weight compound can also be obtained by reacting a compound having two or more epoxy groups in one molecule with carbon dioxide.

Here, only typical compounds having two or more epoxy groups in one molecule are exemplified, and sorbitol tetraglycidyl ether and pentaerythritol tetraglycidyl ether may be mentioned. Diglycerol triglycidyl ether, triglycidyl tris (2-hydroxyethyl) isocyanurate, glycerol diglycidyl ether, glycerol triglycidyl ether, trimethylol propane diglycidyl ether, Trimethylolpropane triglycidyl ether, neopentylglycol-diglycidyl ether or 1,6-hexanediol-diglycidyl ether; generally obtained by the reaction of a polyhydric alcohol with epichlorohydrin. Things.

Here, a quaternary ammonium salt such as triethylammonium bromide, triethylammonium iodide, triethylammonium, choline or benzyltrimethylammonium hydroxide; a phosphine such as triphenylphosphine or tolylphosphine to react epoxide with carbon dioxide; Or
A catalyst such as 1,4-diazacyclo [2,2,2] octane, dimethylaminoethanol, piperazine, 4-dimethylaminopyridine or imidazoles such as 1-methylimidazole and 2-phenylimidazole may be used. Of course.

The reaction during this time is generally carried out by contacting the epoxy compound with carbon dioxide in the presence of the catalyst, whereby the epoxy group is converted to a carbonate group.

As described above, a low-molecular compound having at least two 2-oxo-1,3-dioxolan-4-yl groups in one molecule and having a molecular weight of 2,000 or less, that is, containing a cyclocarbonate group Low molecular compounds are all compounds except vinyl polymers and polyester resins.

Next, the second component of the present invention, a catalyst for decomposing a cyclocarbonate group and a catalyst for opening a ring of an epoxy group, will be described. Both of them are a decarbonation reaction based on a cyclocarbonate group (decarbonation gas). And quaternary ammonium salts such as tetramethylammonium fluoride trimethylbenzylammonium hydroxide or trimethylbenzylammonium methoxide. Acid catalysts such as phosphoric acid, p-toluenesulfonic acid or dimethyl sulfate; carbonates such as calcium carbonate; triphenylphosphine; 2-hydroxypyridine; 2-methylimidazole.

The amount of the cyclocarbonate group ring-opening catalyst to be used is in the range of 0.01 to 20 parts by weight based on 100 parts by weight of the solid content of the above-mentioned cyclocarbonate group-containing compound.

Such an amount is greatly affected by the baking temperature, and particularly when the amount is less than 0.01 part by weight, the crosslinking reaction cannot proceed sufficiently, and on the other hand, when the amount exceeds 20 parts by weight, the amount becomes too large. In any case, the storage stability of the thermosetting resin composition is extremely reduced, and the water resistance of the coating film is also significantly reduced.

Furthermore, the most preferred range of use is from 0.1 to 5 parts by weight, especially when strict high performance is required.

Then, the component which may be used for accelerating the reaction between the epoxy group and the carboxyl group-containing and / or acid anhydride group-containing compound generated by the decarboxylation reaction of the cyclocarbonate group may be an ester. The use of a basic catalyst, which is usually used, to promote the formation reaction is most preferable, and the above-mentioned quaternary ammonium salt is most preferable as having the same effect as the catalyst for decomposing the cyclocarbonate group. It is also effective to use triphenylphosphine or the like in combination with the quaternary ammonium salt catalyst.

The amount of the epoxy group-opening catalyst used is suitably up to 20 parts by weight, particularly preferably 5 parts by weight, based on 100 parts by weight of the above-mentioned cyclocarbonate group-containing compound solids. Use within the following range:

Further, the compound containing a carboxyl group and / or an acid anhydride group is at least one compound selected from the group consisting of a vinyl copolymer, a polyester resin, and a low molecular compound.

First, only typical examples of vinyl copolymers will be exemplified, and α, β-ethylenically unsaturated mono- or dicarboxylic acids such as (meth) acrylic acid, maleic acid, fumaric acid and itaconic acid will be described. Acids; esters of α, β-ethylenically unsaturated dicarboxylic acids and monovalent alcohols having 1 to 4 carbon atoms, such as maleic diethyl, dibutyl maleate, dibutyl fumarate or diethyl itaconate; or β Carboxyl group-containing unsaturated monomer and / or acid anhydride group-containing unsaturated monomer obtained by adding an acid anhydride such as phthalic anhydride to a hydroxyl group-containing vinyl monomer such as -hydroxyethyl (meth) acrylate. And those obtained by copolymerizing the monomer with a copolymerizable unsaturated monomer as described below.

Here, particularly typical examples of other copolymerizable vinyl monomers include alkyl (meth) acrylate having an alkyl group having 1 to 22 carbon atoms, 2-ethoxyethyl ( Various (meth) acrylates containing no reactive polar group, such as (meth) acrylate or cyclohexyl (meth) acrylate; hydroxyalkyl (meth), such as 2-hydroxylethyl (meth) acrylate or 4-hydroxybutyl (meth) acrylate Acrylates; hydroxyalkyl vinyl ethers such as 2-hydroxyethyl vinyl ether or 4-hydroxybutyl vinyl ether; hydroxyl-containing α, β-ethylenically unsaturated monomers such as allyl alcohol or hydroxyethyl aryl ether; glycidyl (meth) acryle Various reactive polar group-containing (meth) acrylates such as styrene; aromatic vinyl monomers such as styrene, tertiary butylstyrene, α-methylstyrene or vinyltoluene; (meth) acrylamide or N-alkoxymethyl (Meth) acrylamides such as fluorinated (meth) acrylamide; or fluorine-containing vinyl monomers such as tetrafluoroethylene or hexafluoropropylene,
(Meth) acrylonitrile, vinyl acetate or (meth) acrylates containing a phosphoric acid group. These various monomers can be converted to the above-mentioned α, β-containing a carboxyl group and / or an acid anhydride group according to a known and commonly used method. What is necessary is just to copolymerize with an ethylenically unsaturated monomer.

In addition, the carboxyl group-containing polyester resin is obtained by reacting an acid component in excess with a polyhydric alcohol, or is obtained by reacting an acid anhydride group with a hydroxyl group-containing polyester resin. is there.

The polyester resin referred to here is not special, and generally used polyvalent carboxylic acids such as phthalic acid, isophthalic acid, adipic acid, maleic acid or dimer acid, and ethylene glycol, propylene glycol, neopentyl Glycols are those obtained by condensing a commonly used polyol, such as trimethylolpropane, with a commonly used method.

More specifically, it is obtained by adding an acid anhydride group-containing compound such as trimellitic acid to a hydroxyl-terminated polyester obtained by a reaction in excess of a polyol component, or from the beginning. It should be understood that this is a carboxyl-terminated polyester resin such as that obtained by reaction in excess of a polycarboxylic acid.

The carboxyl group-containing low molecular weight compound referred to in the present invention refers to a compound having a molecular weight of at most 2,000, such as adipic acid, phthalic acid, isophthalic acid or dimer acid.

Further, the acid anhydride group-containing low molecular weight compound as referred to in the present invention, trimellitic acid, tetrahydrophthalic anhydride, hexahydrophthalic anhydride, heptanoic anhydride, hymic anhydride, maleic anhydride, itaconic anhydride, pyromellitic anhydride , Such as glycerol tris (trimellitate) or ethylene glycol (trimellitate), etc., having a molecular weight of at most 2,000.

Here, the number average molecular weight of the carboxyl group and / or acid anhydride group-containing polyester resin, vinyl resin, and alkyd resin is appropriately in the range of 500 to 100,000. It is desirable to use something of about 20,000.

Further, the compound containing a carboxyl group and / or an acid anhydride group and the low molecular compound containing a cyclocarbonate group are the same as the compound containing a carboxyl group and / or an acid anhydride group.
The cyclocarbonate group-containing low molecular weight compound is used in an amount of 0.5 to 1,000 parts by weight with respect to parts by weight, but preferably 5 to 500 parts in consideration of compatibility and the like.

The thermosetting resin composition of the present invention thus obtained can be used as it is as a clear coating,
Furthermore, it can be used as an enamel paint by blending a pigment.

In addition, the composition of the present invention may contain, if necessary, various conventional additives such as a leveling agent, an ultraviolet absorber, and a pigment dispersant.

Further, the composition of the present invention may be added with known and commonly used cellulose compounds, plasticizers or polyester resins.

The coating method of the composition of the present invention, such as brush coating, spray coating or roll coating, can be employed a known and commonly used method, and as a curing method, from a so-called forced drying within a wide range of 60 to 180 ° C. The 2-oxo-1,3-dioxolan-4-yl group-containing low molecular compound which is an essential film-forming component of the composition of the present invention. −1,
The ratio of the 3-dioxolan-4-yl group to the carboxyl group and / or acid anhydride group present in the carboxyl group and / or acid anhydride group-containing compound, or a cyclocarbonate group decomposition catalyst; It is possible to design an optimum formulation according to the combination with the epoxy ring-opening catalyst.

The thermosetting resin composition of the present invention can be used as an automobile top coat or the like, or can be mainly used for various metal materials. In particular, remarkable effects can be expected in fields such as acrylic resin / melamine resin paint systems, which have not yet reached the required levels in terms of acid resistance, weather resistance, and coating film appearance.

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

Reference Example 1 (Example of preparing low-molecular compound containing 2-oxo-1,3-dioxolan-4-yl group) 500 methyl ethyl ketone was placed in a four-necked flask equipped with a thermometer, a cooling tube, a stirrer, and a nitrogen gas inlet tube. Department,
"Bernock DN-950" [Polyisocyanate compound manufactured by Dainippon Ink and Chemicals, Incorporated; nonvolatile content = 75
%, NCO content = 13%] and heated to 50 ° C.

Next, a solution consisting of 279 parts of methyl ethyl ketone and 354 parts of glycerin cyclocarbonate was added dropwise over 1 hour. After dropping, the reaction was continued for 20 hours at the same temperature.
The target compound having three cyclocarbonate groups in one molecule was obtained.

Reference Example 2 (same as above) In the same reaction vessel as Reference Example 1, methyl ethyl ketone was added.
1000 parts, 236 parts of glycerin cyclocarbonate and 300 parts of triethylamine were charged, and a solution consisting of 267 parts of sebacic chloride and 300 parts of methyl ethyl ketone was added dropwise at 25 ° C. in 1 hour. Thereafter, the temperature was raised to 50 ° C., and the reaction was continued for 20 hours.

After the completion of the reaction, triethylamine hydrochloride was removed by washing with a large amount of water, followed by drying under reduced pressure to obtain a target compound having two cyclocarbonate groups in one molecule.

Reference Example 3 (same as above) In a reaction vessel similar to Reference Example 1, 168 parts of hexamethylene diisocyanate and 300 parts of methyl ethyl ketone were charged, and the temperature was raised to 50 ° C. to obtain 325 parts of polytetraethylene glycol having an average molecular weight of 650. And 460 parts of methyl ethyl ketone were gradually added dropwise. After the reaction was continued for 10 hours, 264 parts of hydroxyethyl cyclocarbonate was added, and the reaction was continued at the same temperature for 20 hours to obtain the target compound having two cyclocarbonate groups in one molecule. Obtained.

Reference Example 4 (same as above) In the same reaction vessel as in Reference Example 1, methyl ethyl ketone was added.
A solution consisting of 500 parts, 67 parts of trimethylolpropane and 200 parts of triethylamine was added at 25 ° C., and a solution consisting of 271 parts of chloroformylmethylcyclocarbonate and 1,000 parts of methylethylketone was added dropwise at 1 hour. Thereafter, the temperature was raised to 50 ° C., and the reaction was continued for 20 hours.

After completion of the reaction, triethylamine hydrochloride was removed by washing with a large amount of water, followed by drying under reduced pressure to obtain a target compound having three cyclocarbonate groups in one molecule.

Reference Example 5 (same as above) In a four-necked flask equipped with a thermometer, a cooling pipe, a stirrer, and a carbon dioxide gas introduction pipe, 500 methyl alcohol was added.
, 200 parts of sorbitol tetraglycidyl ether and 5 parts of triethylammonium bromide were charged, and the temperature was raised to 50 ° C.

Next, the reaction was continued for 20 hours while blowing carbon dioxide gas from the gas inlet tube.

Thereafter, methyl alcohol was removed, and distillation was performed using a thin-film distillation apparatus to obtain a target compound having four cyclocarbonate groups in one molecule.

Reference Example 6 (Preparation Example of Carboxyl Group-Containing Vinyl Copolymer) In a reaction vessel similar to that of Reference Example 1, 700 parts of toluene and 300 parts of n-butyl alcohol were charged, and the temperature was raised to 100 ° C. On reaching, 300 parts of styrene, 100 parts of methyl methacrylate, 500 parts of n-butyl methacrylate, 100 parts of methacrylic acid, 12.5 parts of azobisisobutyronitrile and 12.5 parts of t-butyl peroxybenzoate The resulting mixture was added dropwise over 4 hours. After the completion of the dropwise addition, the reaction was continued at the same temperature for 20 hours.

The copolymer thus obtained has a nonvolatile content of 50% and a content of 25%.
Gardner viscosity at ° C (hereinafter abbreviated as viscosity)
Was TU, and the number average molecular weight in terms of styrene (the same applies hereinafter) measured by gel permeation chromatography was 9,000.

Reference Example 7 (Preparation example of carboxyl group-containing polyester resin) 4 equipped with a thermometer, a stirrer, and an air condenser
In a one-necked flask, add 174 parts of adipic acid and 164 parts of phthalic acid.
, 104 parts of neopentyl glycol, 10 parts of trimethylolpropane and 1 part of dibutyltin oxide were charged and reacted at 140 ° C for 1 hour, and then heated to 220 ° C over 3 hours. Thereafter, the reaction was continued at the same temperature for 15 hours, cooled, and diluted with 400 parts of toluene.

The resin thus obtained has an acid value of 25, a hydroxyl value of 3,
The nonvolatile content was 50%, the viscosity was VW, and the number average molecular weight was 5,200.

Reference Example 8 (Preparation Example of Hydroxyl Group-Containing Vinyl Resin) In a reaction vessel similar to Reference Example 1, 700 parts of toluene and 300 parts of n-butyl alcohol were charged, and the temperature was raised to 100 ° C. 300 parts of styrene, 100 parts of methyl methacrylate, 360 parts of n-butyl methacrylate, 10 parts of methacrylic acid, 230 parts of β-hydroxyethyl methacrylate, 12.5 parts of azobisisobutyronitrile and t-butyl 1 of peroxybenzoate
A mixture of 2.5 parts was added dropwise over 4 hours.

 After the completion of the dropwise addition, the reaction was continued at the same temperature for 20 hours.

The resin thus obtained had a nonvolatile content of 50%, a viscosity of VW, and a number average molecular weight of 9,800.

Example 1 100 parts of the compound obtained in Reference Example 1, 40 parts of the compound obtained in Reference Example 6, 1 part of 2-hydroxypyridine, and 1 part of triphenylphosphine were mixed,
A thermosetting resin composition was obtained.

Examples 2 to 6 and Comparative Examples 1 and 2 In Tables (1), (2) and (3),
Various thermosetting resin compositions were obtained in the same manner as in Example 1 except that the change was performed as shown.

Application Examples 1 to 6 and Comparative Application Examples 1 and 2 Various thermosetting resin compositions obtained in each of the Examples and Comparative Examples were mixed with toluene so that the time could be 25 seconds with a Ford Cup # 4. After dilution, they were applied to test plates by air-spray.

Then, after setting for 10 minutes, 140
Heat drying was performed at 20 ° C. for 20 minutes.

The cured coating film thus obtained was evaluated for various properties.

The results are collectively shown in Table 1. The evaluation of each coating film performance was determined in the following manner.

Gel fraction: The proportion of the insoluble component after immersion in acetone for 24 hours was measured.

Pencil hardness: "Mitsubishi Uni" [Mitsubishi Pencil Co., Ltd. product]
The hardness of the coating film was determined by using the following formula.

Water resistance: The state of the coated surface after being immersed in ion-exchanged water at 25 ° C. for one week was visually judged.

Xylene rubbing: 2,100g using a rubbing tester
After the rubbing was performed 50 times with xylene under the applied load, the state of the coated surface was visually determined.

Chemical resistance: 5% sulfuric acid aqueous solution or 5%, respectively
The state of the coated surface after being immersed in an aqueous sodium hydroxide solution for one week was visually determined.

Weather resistance / QUV test …… QUV tester “Q-UV” (US Q
-Panel Co., Ltd.), a 2,000-hour accelerated weather resistance test was performed, and the gloss retention (%) before and after the test was determined and indicated.

Weather resistance / Outdoor exposure: Exposure was performed for two years in Miyazaki Prefecture, and the gloss retention (%) before and after the test was determined and indicated.

 Appearance of coating film: The state of the coated surface was visually judged.

[Effect of the Invention] The thermosetting resin composition of the present invention can be used as a one-pack type paint.
It is excellent in storage stability and, therefore, not only good in workability, but also excellent in acid resistance, weather resistance and coating film appearance, especially smoothness. .

Therefore, it can be said that the thermosetting resin composition of the present invention opens up a new field as a baking paint.

Continuation of front page (58) Field surveyed (Int.Cl. ⁷ , DB name) C08G 65/16 C08L 1/00-101/16 C09D 1/00-201/10

Claims (7)

(57) [Claims] (1) at least two 2-oxo-1,3-dioxolanes represented by the general formula (I) in one molecule:
A low molecular weight compound having a 4-yl group and a molecular weight of 2,000 or less, and a ring-opening catalyst for a 2-oxo-1,3-dioxolan-4-yl group containing a quaternary ammonium salt and / or triphenylphosphine And the content of the ring-opening catalyst relative to 100 parts by weight of the solid content of the low-molecular compound is
A thermosetting resin composition, which is 0.1 to 20 parts by weight. 2. At least two 2-oxo-1,3-dioxolanes of the general formula [I] in one molecule.
A low molecular weight compound having a 4-yl group and a molecular weight of 2,000 or less is represented by the general formula [II].
The thermosetting resin composition according to claim 1, which is derived from a compound containing a dioxolan-4-yl group and a polyisocyanate and / or a polycarboxylic acid. 3. A compound having at least two 2-oxo-1,3-dioxolanes of the general formula [I] in one molecule.
A low-molecular compound having a 4-yl group and a molecular weight of 2,000 or less is produced by reacting a compound having at least two epoxy groups in one molecule with carbon dioxide. 2. The thermosetting resin composition according to 1. 4. A compound having at least two 2-oxo-1,3-dioxolanes of the formula [I] in one molecule.
A low-molecular compound having a 4-yl group and a molecular weight of 2,000 or less, a compound having at least two carboxyl groups and / or acid anhydride groups in one molecule, and at least one type of 2-oxo- A ring-opening catalyst for a 1,3-dioxolan-4-yl group, and the content of the low-molecular compound is 0.5 to 1,000 parts by weight relative to 100 parts by weight of the compound having a carboxyl group and / or an acid anhydride group. A thermosetting resin composition, wherein the content of the ring-opening catalyst is 0.1 to 20 parts by weight based on 100 parts by weight of a solid content of the low-molecular compound. 5. A compound having at least two 2-oxo-1,3-dioxolanes of the formula [I] in one molecule.
A low molecular weight compound having a 4-yl group and a molecular weight of 2,000 or less is represented by the general formula [II].
The thermosetting resin composition according to claim 4, which is derived from a compound containing a dioxolan-4-yl group and a polyisocyanate and / or a polycarboxylic acid. 6. At least two 2-oxo-1,3-dioxolanes of the general formula [I] in one molecule.
A low-molecular compound having a 4-yl group and a molecular weight of 2,000 or less is produced by reacting a compound having at least two epoxy groups in one molecule with carbon dioxide. 5. The thermosetting resin composition according to 4. 7. The thermosetting composition according to claim 4, wherein the compound having at least two carboxyl groups and / or acid anhydride groups in one molecule is a polyester resin, an alkyd resin and a vinyl resin. Resin composition.