JP2870880B2 - Resin composition for glass protective paint - Google Patents

Description

The present invention relates to a novel and useful resin composition for glass protective coatings. More specifically, the present invention comprises a specific resin, a polyurethane-vinyl resin block copolymer, as an essential component, and has, among other things, adhesion to glass, moderate flexibility and hardness, The present invention relates to a resin composition which is extremely useful not only for protection of glass but also for prevention of crushing of glass and prevention of scattering at crushing.

Thus, the composition of the present invention in a novel form exhibits an epoch-making effect as a glass protective coating. Glass products or the like (hereinafter, also referred to as glass) such as ordinary window glass, show window glass, automobile glass, mirrors, fluorescent lamps, light bulbs or lenses, or pottery are easily broken by impact, Moreover, when broken, these fragments are scattered and are extremely dangerous. However, the resin composition for glass protective coating of the present invention
First, it is applied to the surface of glass to protect the glass surface, and in the event that the glass is broken, scattering of glass fragments is prevented.

[Conventional technology]

As this kind of glass protective coating, vinyl chloride resin and two-pack type acrylic-urethane resin are well known, but the former resin is known for its toxicity. There is a problem in the safety of the coating operator, and the latter resin has a problem in workability because it is itself a two-pack.

In addition, at present, there is no such thing that is satisfactory and satisfactory in terms of performance.

[Problems to be solved by the invention]

Therefore, the present inventors, based on the recognition of the current situation, various unresolved problems in the prior art, and the urgent demand in the art, are overnight and substantially non-toxic, In addition, the present inventors have intensively researched for a highly useful resin composition for a glass protective coating which is extremely useful.

Therefore, the problem to be solved by the present invention is, on the one hand, protection of glass, ie, prevention of crushing of glass, and glass protection which is extremely useful in preventing shards of shards in the event of crushing. An object of the present invention is to provide a coating resin composition.

[Means for solving the problem]

The present inventors have conducted intensive studies, aiming at the problems to be solved by the invention as described above, and as a result, a specific resin called a polyurethane-vinyl resin block copolymer as an essential component, respectively. Or, a resin composition containing a specific resin as the block copolymer and a silane coupling agent as an essential component, first, glass protection, as well as appropriate flexibility and hardness for preventing glass scattering at the time of crushing. The present invention is based on the finding that it has a good adhesive property, and that it is an overnight type, has substantially no toxicity, and has high performance. Was completed.

That is, the present invention comprises a polyurethane-vinyl resin block copolymer as an essential component, or comprises a polyurethane-vinyl resin block copolymer and a silane coupling agent as essential components,
In particular, it is possible to provide a resin composition for a glass protective coating material which is extremely useful in preventing crushing of glass and preventing scatter of glass in the event of crushing.

Here, the above-mentioned polyurethane-vinyl resin block copolymer refers to a polyurethane
It refers to those that predominantly contain a copolymer having a segment and a vinyl resin / segment in a block shape, but the block copolymer is, in principle, a diazo bond and a urethane bond in the main chain. (Hereinafter, also referred to as a polymer azo initiator) in the presence of a polymerizable unsaturated monomer.

As such a high molecular azo initiator, a general formula And the general formula [However, R ₃ in the formula represents a polyol residue. It is particularly preferable to use a compound having at least one structural unit represented by the following formula in one molecule, and particularly preferable to use a compound having a number average molecular weight in the range of 1,500 to 50,000.

Such polymeric azo initiators include, for example, azobiscyanopropanol, azobiscyano-α-butanol,
An azobiscyanoalkanol compound such as azobiscyanoisobutanol or azobiscyanopentanol, or an azoamide polyol such as "VA-080, VA-082 or VA-086" (a product of Wako Pure Chemical Industries, Ltd.). A typical example is a compound obtained by reacting a compound having at least one diazo bond and at least two hydroxyl groups in one molecule with a polyisocyanate compound.

That is, such polyurethane-type polymer polyazo initiators include, for example, isophorone diisocyanate, methylcyclo-hexane-2,4-diisocyanate, methylcyclohexane-2,6-diisocyanate, 4,4'-methylenebis (cyclohexylisocyanate), 1,3 Various diisocyanates such as di (isocyanatomethyl) cyclohexane, tetramethylene diisocyanate, hexamethylene diisocyanate, trimethylcyclohexane diisocyanate, tolylene diisocyanate or xylene diisocyanate, or each of these diisocyanates and glycerin, trimethylolethane, trimethylolpropane Polyhydric alcohols such as pentaerythritol or dipentaerythritol, or Having a functional group capable of reacting with a cyanate group, for example, having a number average molecular weight of about 500 to 1,500, a polyisocyanate compound such as an adduct with a very low molecular weight polyester compound, ethylene glycol, diethylene glycol, propylene glycol, Dipropylene glycol, 1,4-butanediol, 1,3-butanediol, 1,6-hexanediol,
3-methyl-1,5-pentadiol, neopentyl glycol, cyclohexanedimethanol, dimethylolpropionic acid or polyethylene glycol having a number average molecular weight of about 1500, polypropylene glycol or polyhexamethylene glycol, or trimethylolethane, Trimethylolpropane, glycerin,
Various di- or polyols such as pentaerythritol or hydrogenated bisphenol A, and further, such as bisphenol A or polyester polyol, and at least one diazo bond and at least two hydroxyl groups in one molecule as described above. It can be obtained by performing an addition condensation reaction of a three-component with a compound.

Here, as the number average molecular weight of the di- or polyol compound, from the viewpoint of reactivity and the like,
Preferably, up to 1,500, more preferably 1,0
Desirably it is up to 00

Furthermore, if only typical polyester polyols mentioned above are exemplified, various di- or polyol compounds as described above, isophthalic acid, terephthalic acid, (phthalic anhydride), (tetrahydrofuran) Obtained by dehydration condensation with various di- or polycarboxylic acids (anhydrides) such as phthalic acid, (anhydride) hexahydrophthalic acid, trimellitic anhydride, pyromellitic acid, fumaric acid, maleic acid, succinic acid or adipic acid And / or a hydroxyl group-containing polyester resin obtained by ring-opening polymerization of various lactone compounds such as ε-caplactone or valerolactone. It is obtained by a reaction method.

As a synthesis method at that time, a method in which these three components are simultaneously charged and reacted, or an isocyanate group-containing polyurethane intermediate (that is, a so-called urethane prepolymer) is first prepared, and then at least one isomer is added in one molecule. There is a method of reacting a compound having two diazo bonds and at least two hydroxyl groups, but such a synthesis method is not particularly limited.

In addition, these di- or polyol compounds and di-
Or various polyamines such as ethylenediamine, hexamethylenediamine, triethylenetetramine, tetraethylenepentamine, bisaminopropylamine or 4-aminomethyl-1,8-diaminooctane as a chain extender during the reaction with the polyisocyanate compound. Of course, compounds may be used.

Further, the polymerizable unsaturated monomer is styrene,
aromatic vinyl monomers such as α-methylstyrene, pt-butylstyrene or vinyltoluene; methyl (meth) acrylate, ethyl (meth) acrylate, n-propyl (meth) acrylate, i-propyl (meth) acrylate , N-butyl (meth) acrylate, i-butyl (meth) acrylate, t-butyl (meth) acrylate, 2-ethylhexyl (meth) acrylate, lauryl (meth) acrylate, cyclohexyl (meth) acrylate, benzyl (meth) acrylate (Meth) acrylates such as dibromopropyl (meth) acrylate, tribromophenyl (meth) acrylate or alkoxyalkyl (meth) acrylate; and unsaturated dicarboxylic acids such as maleic acid, fumaric acid or itaconic acid. Diesters of a polyhydric alcohol;
Vinyl acetate, vinyl benzoate or vinyl esters such as "Veova" (Vinyl ester manufactured by Shell); "Viscoat 8F, 8FM, 17FM, 3F or 3FM" (fluorinated acrylic monomer manufactured by Osaka Organic Chemical Co., Ltd.), (Per) fluoroalkyl group-containing vinyl esters, vinyl ethers, such as perfluorocyclohexyl (meth) acrylate, di-perfluorocyclohexyl fumarate or Ni-propyl perfluorooctanesulfonamidoethyl (meth) acrylate ) Fluorine-containing polymerizable compounds such as acrylates or unsaturated polycarboxylic esters; or having no functional groups such as olefins such as (meth) acrylonitrile, vinyl chloride, vinylidene chloride, vinyl fluoride or vinylidene fluoride. Vinyl monomer (Meth) acrylamide, dimethyl (meth) acrylamide, N-tert-butyl (meth) acrylamide, N-octyl (meth) acrylamide, diacetone acrylamide, dimethylaminopropyl acrylamide, alkoxylated N-methylolated (meth) acrylamide Bond-containing vinyl monomers such as dialkyl [(meth) acryloyloxyalkyl] phosphates or (meth) acryloyloxyalkyl acid phosphates, dialkyl [(meth) acryloyloxyalkyl] phosphites or ( (Meth) acryloyloxyalkyl acid phosphites; further, the above (meth) acryloyloxyalkyl acid phosphates, or alkylene oxide adducts of acid phosphites; Ester compounds of an epoxy group-containing vinyl monomer such as lysidyl (meth) acrylate or methyl glycidyl (meth) acrylate with phosphoric acid or phosphorous acid or acid esters thereof, 3-chloro-2-acidphosphoxypropyl (meth) Phosphorus atom-containing vinyl monomers such as acrylate; dialkylaminoalkyl (meth) acrylates such as dimethylaminoethyl (meth) acrylate and diethylaminoethyl (meth) acrylate; 2-hydroxyethyl (meth) acrylate, 2-hydroxypropyl ( (Meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3-hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3- Loro-2-hydroxypropyl (meth) acrylate, di-2-hydroxyethyl fumarate, mono-2-hydroxyethyl monobutyl fumarate, or polypropylene glycol or polyethylene glycol mono (meth) acrylate, "Placcel FM, FA monomer Hydroxyalkyl esters of α, β-ethylenically unsaturated carboxylic acids or adducts thereof with ε-caprolactone, such as [caprolactone-added monomers manufactured by Daicel Chemical Co., Ltd.]; (meth) acrylic acid, crotonic acid, Unsaturated monomers such as maleic acid, fumaric acid, itaconic acid or citraconic acid or dicarboxylic acids, α, β-ethylenically unsaturated carboxylic acids such as monoesters of these dicarboxylic acids and monohydric alcohols, or The α β- ethylenically unsaturated carboxylic acid hydroxyalkyl esters and maleic acid, succinic acid, phthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, benzene tricarboxylic acid,
Various unsaturated carboxylic acids such as benzenetetracarboxylic acid, "Hymic acid" (product of Hitachi Chemical Co., Ltd.), and adducts of polycarboxylic acids such as tetrachlorophthalic acid or dodecynylsuccinic acid with "Kajura E" [Glycidyl ester of a branched synthetic resin fatty acid manufactured by Shell, Netherlands], palm oil fatty acid glycidyl ester or octylic acid glycidyl ester.
Monoglycidyl ester of a monovalent carboxylic acid or an adduct of a monoepoxy compound such as butyl glycidyl ether, ethylene oxide or propylene oxide or an adduct thereof with ε-caprolactone; a hydroxyl group-containing monomer such as hydroxy vinyl ether; (meth) acrylic Acid, crotonic acid, maleic acid, fumaric acid,
Α, β-ethylenically unsaturated carboxylic acids such as unsaturated mono- or dicarboxylic acids such as itaconic acid or citraconic acid, and monoesters of these dicarboxylic acids and monohydric alcohols; 2-hydroxyethyl (meth) Acrylate, 2-hydroxypropyl (meth) acrylate, 3-hydroxypropyl (meth) acrylate, 2-hydroxybutyl (meth) acrylate, 3
-Hydroxybutyl (meth) acrylate, 4-hydroxybutyl (meth) acrylate, 3-chloro-2-hydroxypropyl (meth) acrylate, di-2-hydroxyethyl fumarate, mono-2-hydroxyethyl-monobutyl fumarate Or α, β-unsaturated carboxylic acid hydroalkyl esters such as polyethylene glycol mono (meth) acrylate and maleic acid, succinic acid, phthalic acid, hexahydrophthalic acid, tetrahydrophthalic acid, benzenetricarboxylic acid, benzenetetracarboxylic acid, "Hymic acid" (a product of Hitachi Chemical Co., Ltd.), carboxyl group-containing monomers such as adducts of polycarboxylic acids such as tetrachlorophthalic acid or dodecynylsuccinic acid with vinyl anhydride; vinylethoxysilane, α-methacryloxypropyl bird Tokishishiran or trimethylsiloxy ethyl (meth) acrylate or "KR
-215 "or" X-22-5002 "(a product of Shin-Etsu Chemical Co., Ltd.).

In order to improve the adhesion to the glass surface, it is particularly effective to use the above-mentioned phosphorus atom-containing vinyl monomers, dialkylaminoalkyl (meth) acrylates, hydroxyl group-containing monomers, carboxyl group-containing monomers or silicon-based monomers. It is. In particular, when a silane coupling agent is used in combination, it is better to copolymerize a polar group-containing monomer such as a carboxyl group-containing monomer, and 100 parts by weight of the polymerizable unsaturated monomer used in the polymerization. , About 0.1 to 20 parts by weight is suitable, but not particularly limited.

For the purpose of further improving the weather resistance, for example, “T
A polymerizable ultraviolet absorber or light stabilizer such as "-37" or "LA-82" (a product of Adeka Argus Chemical Co., Ltd.) can also be copolymerized.

The polymerization for obtaining the polyurethane-vinyl resin block copolymer can be carried out by making use of the above-mentioned respective raw material components and making full use of a known and common copolymerization reaction method. In that case, azobisisobutyronitrile ( AIBN), benzoyl peroxide (BPO), tert-butyl perbenzoate (T
BPB), tert-butyl hydroperoxide, di-tert
It is a matter of course that radical-generating polymerization catalysts such as -butyl peroxide, (DTBPO) or cumene hydroperoxide (CHP) may be used alone or in combination of several kinds.

Examples of the silane coupling agent include vinyl trichlorosilane, vinyl triethoxy silane, γ-
Chloropropyltrimethoxysilane, γ-chloropropylmethyldichlorosilane, γ-chloropropylmethyldimethoxysilane, γ-chloropropylmethyldiethoxysilane, γ-aminopropyltrimethoxysilane, N-
(Β-aminoethyl) -γ-aminopropyltrimethoxysilane, N- (β-aminoethyl) -γ-aminopropylmethyldimethoxysilane, γ-mercaptopropyltrimethoxysilane, γ-glycidoxypropyltrimethoxysilane, γ-glycidoxypropylmethyldimethoxysilane, γ-methacryloxypropyltrimethoxysilane, γ-methacryloxypropylmethyldimethoxysilane and the like are particularly typical examples and are used for improving or adjusting the adhesion to the glass surface. Is done.
It is appropriate to use about 0.1 to 20 parts by weight with respect to 100 parts by weight of the block copolymer, but it is not particularly limited.

Further, when the composition of the present invention is used for a light bulb or a fluorescent lamp, additives such as a known and commonly used ultraviolet absorber and a light stabilizer can be added to the composition of the present invention.

〔The invention's effect〕

As described above, the glass protective coating resin composition of the present invention contains the polyurethane-vinyl resin block copolymer thus obtained as an essential component, or contains the block copolymer and silane. A coupling agent and an essential component, which is overnight, substantially non-toxic, and has a good balance between flexibility and hardness, and also has good adhesion. It is very useful because it can provide a coating film that retains high performance in protecting glass, that is, preventing crushing of glass and preventing scattering of glass.

Accordingly, the resin composition for glass protective coating of the present invention can be used for various glass products such as ordinary window glass, show window glass, automobile glass, mirror, fluorescent lamp, light bulb or lens, or ceramics, or similar materials. It is versatile and extremely useful for things.

〔Example〕

Next, the present invention by reference examples, examples and comparative examples,
This will be described more specifically. In the following, parts and%
All are by weight unless otherwise specified.

Reference Example 1 (Preparation Example of Polymer Azo Initiator) In a four-necked flask equipped with a thermometer, a stirrer and a reflux condenser, 1,500 parts of methyl ethyl ketone, 424 parts of dipropylene glycol and di-n-butyltin dilaurate were placed. Was heated to 80 ° C. with stirring, 532 parts of hexamethylene diisocyanate was added dropwise over 2 hours, and the reaction was continued at 80 ° C. for 5 hours. .

The polystyrene-equivalent number average molecular weight of the obtained isocyanate group-containing polyurethane measured by gel permeation chromatography (GPC) was 3,3.
700. However, after the treatment of reacting the isocyanate group with diethylamine, it is used for measurement by GPC.

Next, 2,456 parts of this isocyanate group-containing polyurethane was charged into the same reaction vessel as described above, and 44 parts of azobisisopropanol was added to the polyurethane under ice-cooling, and then the temperature was raised to 30 ° C. Then, the reaction was carried out while maintaining the same temperature for 10 hours.

The number average molecular weight of the thus obtained polyurethane polymer azo initiator is 22,500, and therefore,
It is known to be a polyurethane polymer azo initiator having an average of 6.1 diazo bonds in one molecule.

This objective initiator solution has a nonvolatile content of 40%,
And Gardner viscosity at 25 ° C. was Z _1.

Reference Example 2 (same as above) In the same reaction vessel as in Reference Example 1, methyl ethyl ketone was added.
1,500 parts, 46 parts of azobiscyanopropanol and-
0.1 part of n-butyltin dilaurate was charged, and while stirring and under ice cooling, 55 parts of hexamethylene diisocyanate was added.
After 2 parts were added dropwise over 2 hours, the temperature was raised to 20 ° C., the temperature was maintained for 2 hours, and the reaction was continued.
Again, ice cooling was performed.

Then 347 parts of dipropylene glycol and 3-
55 parts of methyl-1,5-pentanediol was added, the temperature was raised to 30 ° C., and the temperature was maintained for 10 hours to continue the reaction. The polyurethane polymer azo initiator obtained here had a number average molecular weight of 18,500, a viscosity of YZ, and a non-volatile content of 40%.

To determine other property values for this polymeric azo initiator, add 1.0 part hydroquinone and 20 parts n-butanol to 20 parts of the initiator and heat at 100 ° C. for 10 hours. Was continued to decompose the initiator. The number average molecular weight of the decomposition product obtained here is 4,100
The target polymer azo initiator has an average molecular weight in one molecule.
It was found to have 4.5 diazo bonds.

Reference Example 3 (same as above) A reaction vessel equipped with a thermometer, a stirrer and an air condenser was charged with 614 parts of adipic acid, 438 parts of neopentyl glycol and 698 parts of isophthalic acid, and charged with 140 parts.
C. for 1 hour, then slowly over 2 hours
The temperature was raised to 220 ° C., and the mixture was reacted at the same temperature for 6 hours to obtain a polyester resin having 2 oxidation, 78 hydroxyl groups and a number average molecular weight of 1,400.

Next, 837 parts of the above polyester resin and 27% of azobiscyanopropanol were placed in the same reaction vessel as in Reference Example 1.
, 0.1 part of di-n-butyltin dilaurate and 1,500 parts of methyl ethyl ketone, and 134 parts of hexamethylene diisocyanate were added dropwise over 2 hours under ice cooling.

After the completion of the dropwise addition, the temperature was raised to 30 ° C., the temperature was maintained for 10 hours to continue the reaction, and the number average molecular weight was 28,0.
As a result, a solution of the target polyurethane polymer azo initiator having a viscosity of WX and a nonvolatile content of 40% was obtained.

Incidentally, for 20 parts of this polyurethane polymer azo initiator, 1.0 part of hydroquinone and 2 parts of n-
When the polymer azo initiator was decomposed by adding 0 parts and heating at 100 ° C. for 10 hours, the number average molecular weight of the decomposed product was 4,500, and therefore, the polyurethane polymer azo initiator was Average 6.
It was found to have two diazo bonds.

Reference Examples 4 to 12 (same as above) The solvent, azoalkanol compound, polyol compound and polyisocyanate compound were changed as shown in Table 1 and the reaction was carried out under the conditions shown in the same table. Except having been changed as described above, the target various polyurethane polymer azo initiators were obtained in the same manner as in Reference Example 1.

The various property values of the respective polymeric azo initiators are as shown in the same table.

Reference Example 13 (Preparation example of polyurethane-vinyl resin block copolymer) In a four-necked flask equipped with a thermometer, a stirrer, and a reflux condenser, 600 parts of toluene and 1 part of methyl ethyl ketone were added.
Then, a mixture of 400 parts of methyl methacrylate, 400 parts of ethyl acrylate, and 500 parts of the polyurethane polymer azo initiator obtained in Reference Example 1 was charged. Was dropped over 4 hours, and after the completion of the dropping, the polymerization reaction was continued at the same temperature for 10 hours to obtain a non-volatile polyurethane-acrylic resin block copolymer having a number average molecular weight of 28,000. A solution with a 50% min and a Gardner viscosity at 25 ° C. of Z ₃ was obtained.

Reference Examples 14 to 24 (same as above) A polymerization solvent, an initiator and a polymerizable unsaturated monomer as shown in Table 2 were used, and the polymerization conditions were changed as shown in the same table. In the same manner as in Reference Example 13, various block copolymers were obtained.

Reference Examples 25 to 27 (Examples of preparation of random copolymer as control resin) Using a polymerization solvent, an initiator and a polymerizable unsaturated monomer as shown in Table 2, and as shown in the same table Various random copolymers were prepared in the same manner as in Reference Example 13, except that the polymerization was performed under various polymerization conditions.

That is, in this example, the use of a polymeric azo initiator was completely absent, and instead, a general-purpose polymerization initiator (radical generating polymerization catalyst) was used.

Examples 1 to 12 and Comparative Examples 1 to 3 Various resin compositions for glass protective coatings were obtained by a conventional method in accordance with the composition ratios shown in Table 3.

Next, various performances were evaluated using the protective paint as each resin composition.

The evaluation of the coating film performance was performed in the following manner.

Growth-"Tensilon" [Toyo Baldwin Co., Ltd.
[Product] at a tensile speed of 20 mm / min. At room temperature.

Tensile strength-Same as above Pencil hardness-The hardness was measured using "Mitsubishi Uni" (Mitsubishi Pencil Co., Ltd.) until the coating film was scratched.

Stain resistance-the test plate was contaminated with a mixture of mud, carbon black, mineral oil and clay and left for 24 hours,
Then, it was washed with water and wiped off with a dry cloth, and the degree of remaining stains was visually determined.

Adhesion-Gobang (10 x 10) on painted surface on glass test plate
, And then peeled off the gobang with cellophane tape.

Weather resistance-"Q-UV" (Q-Panel, USA)
Was used to perform an accelerated weathering test for 800 hours to evaluate the degree of gloss retention before and after this test.

Mitsuzawa-Murakami formula 60 ° C specular reflection gloss Scratch resistance-After rubbing 20 times with a felt including a cleanser under a load of 1 kg, check the presence or absence of scratches on the coating and the degree of gloss The overall evaluation was made by visual observation.

Protective properties of glass-After painting on a glass plate with a thickness of 2 mm with a thickness of about 150 μm, 20 iron balls with a diameter of about 1 cm are dropped on the painted glass plate from a height of 50 cm Thus, the protection was evaluated.

The evaluation levels are as follows.

◎… No damage ○… Cracked △… Crushed ×… Crushed and scattered Glass shatterproof-immersed in a commercial light bulb, about 150μ
After coating with a thickness of m, the pieces were crushed by dropping them from a height of 1 m onto a concrete floor, and the state of scattering of the crushed light bulb fragments was determined.

As is clear from Table 3, the resin composition for a glass protective coating of the present invention achieves a balance between appropriate hardness and appropriate flexibility, has good adhesion, and The balance of weather resistance, abrasion resistance and stain resistance is also balanced, and the most expected effects are protection of glass (anti-shattering ability) and anti-shattering ability of glass. It is known that it is much better.

Claims (4)

(57) [Claims] 1. A resin composition for a glass protective paint, comprising a polyurethane-vinyl resin block copolymer as an essential component. 2. A resin composition for a glass protective coating, comprising a polyurethane-vinyl resin block copolymer and a silane coupling agent. 3. The polyurethane-vinyl resin block copolymer obtained by polymerizing a polymerizable unsaturated monomer in the presence of a compound having both a diazo bond and a urethane bond in the main chain. The resin composition for a glass protective coating according to claim 1 or 2, wherein 4. The polyurethane-vinyl resin block copolymer according to claim 1, wherein And the general formula [However, R ₃ in the formula represents a polyol residue. The polymerizable unsaturated monomer is obtained by polymerizing a polymerizable unsaturated monomer in the presence of a compound having at least one structural unit represented by the following formula in each molecule. Resin composition for glass protective paint.