JPS59102964A - Coating composition - Google Patents

Abstract

PURPOSE:To provide the titled composition composed of a specific disilane compound containing a carbonate group, and capable of forming a coating film having excellent scratch resistance, abrasion resistance and dyeability to the surface of a molded plastic article in high adhesivity. CONSTITUTION:The objective composition is prepared by mixing (A) a carbonate-containing disilane compound of formula I (A is bivalent atomic group containing a carbonate group and having a main chain composed of >=7 linearly bonded atoms; R<1> and R<2> are alkyl or alkoxy; R<3> and R<4> are alkyl; l and m are 0 or 1) with preferably (B) an organoalkoxysilane compound of formula II(R<5> is hydrocarbon group having vinyl or methacryloxy group, etc., alkyl, or aryl; R<6> is alkyl; n is 0 or 1; R<7> is alkyl or alkoxyalkyl) and (C) one or more substances selected from tetraalkoxysilane compound of formula Si(OR<8>)4 (R<8> is alkyl or alkoxyalkyl), colloidal silica, epoxy compound and melamine derivative.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention provides a method for forming a coating film with high adhesion on the surface of molded products such as plastics and metals, which has excellent scratch resistance and abrasion resistance, and has good dyeability. Coating composition 1tCβ1 is available.

In general, plastic molded products and metal molded products made of aluminum or zinc film are easily damaged due to their low surface hardness.
It has drawbacks such as easy wear. In order to improve these problems, a method of forming a coating film of a curable substance on the surface of the molded article has been carried out, and various coating compositions have been proposed for forming the coating film.

For example, JP-A-53-78273, JP-A-48-55
No. 884 and US Pat. No. 4,027,073 disclose coating compositions containing alkyl tri-7-rukoxysilanes or mixed with tetra-7-rukoxysilanes and co-don-lily compounds. However, the coating film obtained by heating and curing the coating composition after hydrolyzing it has excellent scratch resistance, but has poor adhesion to the surface of the molded product or poor flexibility of the coating film itself. For,
Poor adhesion, peels and cracks in hot water. Therefore, when coating the coating composition,
A method of providing an undercoat layer (7min 7 acrylate type) has been disclosed (4'? 138476/1983), but although this method improves adhesion, the resulting coated film lacks smoothness. For example, uniform dyeing with disperse dyes is difficult. On the other hand, coating compositions containing epoxy group-containing organo-7-sulfoxysilanes and epoxy resins have excellent adhesion and dyeing properties, but have low surface hardness, and in order to increase this, hardening agents and crosslinking agents are mixed. When the ratio increases, the dyeability and adhesion, which were originally good, become poor.

Therefore, the present inventors have conducted intensive research to develop a coating material that can form a coating film with excellent scratch resistance, abrasion resistance, and stainability on the shin surface of plastic molded products with high adhesion. The inventors have discovered that a coating film obtained from a coating composition containing a specific disilane compound having a carbonate group as a constituent component satisfies all of these properties, and has completed the present invention.

That is, the present invention provides general formula (R"0)B-ZSIASJ(OR2)B-m...(1
) A disilane compound containing a carbonate group (wherein A is a divalent atomic group containing a carbonate group and whose main chain is linear and consisting of at least 7 or more atoms, R1
and R2 are the same or different 7-alkyl groups or 7-rukoxy 7-alkyl groups, R8 and R4 are the same or different alkyl groups, and t and m are 0 or 1. .

The greatest feature of the present invention is that, as mentioned above, conventional coating compositions contain only monosolane compounds as a constituent component, whereas disilane compounds containing carbonate groups are used. Since this disilane compound has 4 to 6 alkoxy groups at both ends per molecule, the coat film formed by the polycondensation reaction of its hydrolyzate has a high crosslinking density and high surface hardness. It is thought that it has excellent scratch resistance and abrasion resistance, and also provides solvent resistance. In addition, since the functional groups between Si''Sj have a certain distance, they are easily stained with the molded product, and the coating film itself has elasticity and flexibility, so it can be easily molded using heat. It can respond to the expansion and contraction of products and exhibits excellent adhesion.Furthermore, because it has a carbonate group in the molecule, it has good dyeability with breakaway dyes and can be easily dyed using normal dyeing methods.

Hereinafter, the coating composition of the present invention will be explained in detail.

In the disilane compound containing a carbonate group represented by the general formula (1), R''+R2 is the same or different alkyl convex or alkoxyalkyl group, and has 1 to 6 carbon atoms.
, especially 1 to 3 carbon atoms or carbon atoms 1 to 1+, especially 1 to 6 carbon atoms bonded with 1 to 3 7 alkoxy groups, especially K
An alkoxyalkyl group consisting of a 1'3 alkyl group is preferred. Specifically, K is generally a methyl group, an ethyl group, a probyl group, a methoxyethyl group, or the like. Also, R8
, R4 are the same or different alkyl groups, preferably having 1 to 4 carbon atoms. Specific examples include methyl group, ethyl group, and proyl group. A is a divalent functional group containing a carbonate group, the main chain of which consists of at least 6 or more atoms in a straight line, and has the general formula -CH2CH2CH,OCOR, (Co)qCH,CH
, CH2- (where R is CI-1, CH, 0 or c
H, cH, CII, O, p is an integer from 0 to 4, q
is 0 when p=00 and is 1 when p==1 to 4. Specifically, the following is shown.

These general disilane compounds having a carbonate group represented by 2 (11) can be synthesized by various conventionally known methods. That is, by adding a substituent having an addition -iJ function 7Y2J bond to both ends of the disilane compound. Furthermore, a compound containing a carbonate group inside thereof is treated with (R”O)a-zsiH and/or (R20)B-m under a platinum catalyst.
It can be synthesized by addition reaction of 7-lucoxysilane represented by siH. Alternatively, instead of 7-rukoxysilane, a chlorosilane represented by CtB-zsiH and/or C7B-rnStH is subjected to an addition reaction, and then the RIO process is performed.
A certain degree C. may be 7-rufoxylated with an alcohol represented by R" (Hi. The above reaction conditions are not particularly limited, but
Generally, the above reaction may be carried out at normal pressure and a temperature of -20 to 160 DEG C., if necessary, in a polar nonaqueous solvent such as benzene, toluene, or methyl ether. Further, it is preferable to use platinum black as the platinum catalyst since a colorless and transparent product can be obtained. For example, by reacting diethylene glycol bisallyl carbonate with triethoxysilane under a platinum catalyst, (EtO)8SiCH, CH2CH,
0COCHsCHzOcHaCH20COCH2,CH
BCHBSi(OK:t)a is obtained.

In the present invention, it is preferable that the coating composition containing the carbonate group-containing disilane compound as a constituent component undergoes hydrolysis of the disilane compound prior to coating the molded article. Preferably, the effect is exhibited by using K in a polycondensed form. Hydrolysis of the disilane compound may be carried out by adding and stirring a weakly acidic aqueous solution containing an inorganic acid such as hydrochloric acid or sulfuric acid or an organic acid such as formic acid or acetic acid. However, polycondensation may proceed excessively due to heat generated by hydrolysis, resulting in solidification of the reaction solution or shortening of the life of the prepared coating composition. A car that did
After mixing the disilane compound in an appropriate solvent, preferably at a concentration (hereinafter referred to as a converted concentration) of the disilane compound in a polycondensed state after complete κ hydrolysis, the concentration is 30% by weight or less, Gradual hydrolysis is desirable. In addition, in order to ensure that the hydrolysis reaction and the subsequent partial polycondensation reaction proceed, and to obtain reproducible and stable coating film performance, it is desirable to leave the reaction solution to mature. Approximately 1 to 2 days is appropriate.

During use, the coating composition of the present invention may contain alcohol, 7-rugoxy alcohol, unreacted water, or solvent that is produced as a by-product by hydrolysis, but after hydrolysis, the coating composition may be It is also possible to remove the above components by distillation and then replace the solvent by adding a suitable solvent. and,
The final concentration as a coating composition is 20~
A weight ratio of 40% is preferable.If the coating is less than this, it is difficult to obtain sufficient scratch resistance and abrasion resistance for the coat crotch formed, and if it is lower than -E, the viscosity increases and it is difficult to apply it uniformly to the surface to be coated. becomes difficult. Suitable solvents for replacing the solvent include lower alcohols having carbon fi of 1 to 4 such as methanol, ethanol, propanol and butanol; lower carboxylic acids such as acetic acid and methyl acetate or their alkyl esters; ethers such as Cellsolve. One or more types of carbons such as 7-setone, etc.; logeflated hydrocarbons such as methylene chloride; and aromatic hydrocarbons such as benzene and toluene.

As explained above, the coating composition containing the disilane compound shown in General 2 (11) can form a coating film with excellent properties. The present invention also provides a coating composition that can improve the surface hardness of the resulting coated film by adding a specific compound to the coating composition.

That is, the present invention provides the general formula (R"O)B-zsiASi(OR2)B-?...(
1) An silane compound containing a carbonate group represented by (where A is a divalent atomic group containing a carbonate F group and whose main chain is linear and consisting of at least 7 or more atoms,
R1 and R2 are the same or different alkyl groups or alkoxy7-alkyl groups, R8 and R4 are the same or different alkyl groups, L and m are 0 or 1), and the general formula R5-Si(OR7)8-n・・・・・・・・・・・・
・Organoalkoxysilane compound shown in (2) (
However, R5 is a hydrocarbon group having one of a vinyl group, methacryloxy group, merkabuto group, epoxy group, and amine group as a functional group, or a 7-alkyl group or an aryl group, R6 is an alkyl group, n is 0 or 1, and R7 is an alkyl group or an alkoxyalkyl group), general formula St(OR”)4...
The constituent components are the tetraalkoxysilane compound represented by (3) (wherein R8 is an alkyl group or an alkoxy 7-alkyl group), colloidal silica, an epoxy compound, and at least one additive selected from a melamine conductor. It is a coating composition.

Among the above additives, organo7 represented by general formula (2)
The rukoxysilane compound is particularly suitable for R6 having 1 to 4 carbon atoms,
Those in which R7 has 1 to 4 carbon atoms are generally used. Specifically, methyltrimethoxysilane, dimethyldimethoxysilane, methyltriethoxysilane, ethyltrimethoxysilane, phenyltrimethoxysilane, ethyltriethoxysilane, vinyltrimethoxysilane, vinyltriethoxysilane, vinyltriacetoxysilane, Vinyltrismethethoxysilane, γ-glycidoxypyltrimethoxysilane, r-glycidoxybrobylmethyldimethoxysilane, γ-methacrypoxybrobyltrimethoxysilane, γ-mercaptopropyltrimethoxysilane, β-mercaptopropyltrimethoxysilane (3.4-epoxysic p-hexyl)
Examples include ethyltrimethoxysilane and γ-aminobutyltriethoxysilane.

In addition, as for the tetraalkoxysilane compound represented by the general formula (3), one in which R8 has 1 to 4 carbon atoms is generally used. Specific examples include tetramethoxysilane, tetraethoxysilane, tetrap-boxysilane, and tetraptoxysilane. It is recommended that the alkoxysilane compounds represented by the above general formulas (2) and (3) be used after being hydrolyzed in the same manner as for disilane compounds (in this case, it is also possible to hydrolyze without a solvent). be done.

For example, the alkoxysilane compound may be hydrolyzed and then added to the hydrolyzate solution of the ginran compound, or may be hydrolyzed simultaneously with the disilane compound.

Copoid silica powder can be used as it is or in the form of a colloidal solution obtained by dispersing it in a polar melt. . In the composition of the present invention, a colloidal solution prepared by dispersing the colloidal solution in a polar solvent, for example, water or an alcoholic solvent such as imbropanol, is preferably adjusted to be weakly acidic (・0 Eboxy compounds are conventionally Examples include polyolefin epoxy resins, alicyclic epoxy resins, epoxy nopolac resins, and polyglycidyl ethers of polyhydric alcohols, which are manufactured by the known Kakinaga method.

Melamine D conductors are commercially available mixtures of 7-Lukiger etherified methyl p-lumamine such as hesenzamethoxymethyl melamine with nitrified cotton, or precondensates with polyhydric alcohols such as 1,4-butanediol. It can be prepared and used by conventionally known methods.

The total amount of the above additives is preferably in the range of 10 to 9007 parts by weight, preferably 50 to 200 parts by weight, based on 100 parts by weight of the disilane compound.

In order to lower the curing temperature and shorten the curing time, the coating composition of the present invention uses known compounds as curing catalysts, such as hydrochloric acid, sulfuric acid, a mixture of oxalic acid/sodium acetate, tin chloride, perchloric acid, and perchloric acid. It is preferable to use ammonium acid, aluminum acetyl 7cetonate, metal naphthenate, p-1-luenesulfonic acid, benzoic acid, alkali metal phosphate, sodium thiocyanate, and the like. The amount used is preferably 0.01 to 5 percent by weight based on the amount (hereinafter referred to as "converted amount 5") calculated in terms of K in which the polycondensable components in the coating composition are completely polycondensed.

Of course, the use of a curing catalyst is not essential.

Further, a silicone-based or fluorine-based surfactant can be added to the coating composition of the present invention for the purpose of further improving the smoothness of the coated film. In addition, various other additives such as ultraviolet absorbers, antioxidants, dyes and pigments, and organic carboxylic acids such as formic acid and acetic acid as gelling inhibitors can also be used.

In the present invention, the object to be coated is not particularly limited. Generally, molded products with low surface hardness (poor scratch resistance and wear resistance), especially plastic molded products, are targeted.

For example, polymethyl methacrylate, polymethacrylate, polyethylene terephthalate, polyacrylate 1,
Polyunsaturated esters such as polymethyl acrylate; polystyrenes; polyvinyl chloride; epoxy resins; polyamides; polycarbonates; polyas such as boridiethylene glycol bisallyl carbonate Example 2 A plastic molded article was produced by green mold polymerization. A polyethylene glyco-rubisallyl carbonate plate was used. First, as a pretreatment, the plate-like body was washed with A7Tone and sufficiently air-dried to a clear state, then immersed in a 5% NaOH aqueous solution for 5 minutes, thoroughly washed with K water, and air-dried again. After immersing the above-treated plate-like bodies in coating compositions K prepared in exactly the same manner as in Example 1, except that no curing catalyst was added, the plate-like bodies were thoroughly air-dried at room temperature,
A coated film was obtained by heating and curing at 130° C. for 1 hour. Table 2 shows the evaluation results of the coated films obtained from each coating composition. In either case, the coating film thickness was about 5 to 10 microns.

Example 3 2,2- produced from a plastic molded product by cast polymerization
Bis(4-(2-methacrypoxy)monoethoxy-3,5
-dipmophenyl] A copolymer of broban and styrene (hereinafter referred to as TB-styrene copolymer) with 1゛B/
A plate-shaped body having a styrene weight ratio of 2/3 was used.

First, as a pre-treatment, the plate-shaped body was washed with acetone and thoroughly dried in K air to make it clear, and then in a plasma processing apparatus.
Argon/oxygen mixed gas (flow Jil 30/m/10m
1/mm) under the conditions of a pressure of 0.7'l'orr, an output of 200W, and a processing time of 1 minute, and then washed using an ultrasonic cleaner using acetone as a solvent for 5 minutes, and air-dried again.

In waterfalls 1 to 11 of Example 2, the treated plate-like body was
A coating film was obtained by carrying out a coating treatment in the same manner. The liver value results of the coated films obtained from each coating composition are shown in Table 3K. In either case, the coating film thickness was approximately 5 to 10 microns.

Example 4 In 7165 of Example 1, instead of H,C-CHCHOC8H7S+(OMe)8, 0.5 parts by weight of disperse dye (manufactured by Nippon Kayaku Co., Ltd.; Kayalon-Polyester Brown AF) was added to 100 parts by weight of water. The dyeing bath in which the particles were dispersed and dissolved was kept at 80°C and dyed for 10 minutes. A indicates that it stains as well as or better than polydiethylene glycol bisallyl carbonate-1, which has good stainability, and C indicates that it does not stain as well as or worse than polymethyl methacrylate, which has poor stainability. It was revised in three stages from A to C.

Example 1 A commercially available polymethyl mechacrylate plate was used as a plastic molded product. First, it was washed with methanol and thoroughly air-dried to a clear state, and then coated with the composition shown in Table 1. After soaking in the composition and thoroughly air-drying at room temperature,
The coated silk composition was cured by heating at 80"C for 3 hours. The coating silk composition was prepared by mixing the composition shown in Table 1 with each equivalent of the solvent isopropyl alcohol so that the concentration was 30% by weight. 7 of the above composition.
After adding the equivalent amount of 0.05N hydrochloric acid necessary for hydrolysis of the alkoxy group at room temperature and aging it for one day, 2 weight percentages are calculated using sodium acetate/axic acid (1/10 weight ratio) as a curing catalyst. In addition, it was prepared. In addition, colloidal silica is a catalytic chemical compound! ! OSCAL (Product name: S1023
0 weight percent, particle size 10-20 mμ, solvent impp
alcohol) was used.

Table 1 also shows the evaluation results of the coated films obtained from each coating solution. In either case, the coating film thickness is approximately 5 to 1
It was 0lt.

Below thread mortar Note that 711i9, 10 and 11 are comparative examples.

Example 2 A polyethylene glyfur bisallyl carbonate plate produced by green mold polymerization was used as a plastic molded article. First, as a pretreatment, the plate-like body was washed with A7Tone and sufficiently air-dried to a clear state, then immersed in a 5% NaOH aqueous solution for 5 minutes, thoroughly washed with K water, and air-dried again. The above-treated plate-like bodies were immersed in coating compositions prepared in the same manner as in Examples 1 to 11 except that no curing catalyst was added, and then thoroughly air-dried at room temperature.
A coated film was obtained by heating and curing at 130° C. for 1 hour. Table 2 shows the evaluation results of the coated films obtained from each coating composition. In either case, the coating film thickness was about 5 to 10 microns.

Example 3 2,2- produced from a plastic molded product by cast polymerization
Bis(4-(2-methacrypoxy)monoethoxy-3,5
-dipromophenyl] conjugate of μpan and styrene (hereinafter referred to as TB-styrene conjugate), 1'B/styrene[. A plate-shaped body having a ratio of 2/3 was used.

First, as a pretreatment, the nuclear platelet was washed with amethane and thoroughly air-dried with K to a clear state, and then treated in a plasma processing apparatus.
Argon/oxygen mixed gas (flow Ja: 30ml/dead/10
ml/min) Pressure 0.7'l'orr, Output 200W
, for a treatment time of 1 minute, and then washed using an ultrasonic cleaner using acetone as a solvent for 5 minutes, and air-dried again.

The plate-like bodies treated as described above were coated in the same manner as in Examples 20, Nos. 1 to 11, to obtain coating films. Table 3 shows the valuation results of the coated films obtained from each coating composition. In either case, the coating film thickness was approximately 5 to 10 microns.

Example 4 In 7165 of Example 1, instead of H2CCHCHOCBH7SI(OMe)B\
/ Nipholyethylene glycol diglycine ether (Kyoeisha Yushiyo, Evolai} 200F) Al or hexamethoxymethyl melamine 50 heavy eastern and 1,4-butanediol 5
It is produced by cast polymerization using a coating composition to which the same amount of precondensation material consisting of 0M parts is added. Polydiethylene glycol bisallyl carbonate and TB
/Styrene copolymer plate was pretreated and coated in the same manner as in Example 3 to obtain a coated film. In either case, the adhesion (too/ioo) and scratch resistance (
A), heat resistance (○), hot water resistance (○), and dyeability (
A) was good.

Example 5 A plate of polyethylene glycol bisallyl carbonate produced by cast polymerization ν and a TB/styrene copolymer was pretreated by pressing in the same manner as in Example 3, and the same preparation method as in Example 1 was carried out. After being immersed in coating compositions having various compositions shown in Table 4, the samples were thoroughly air-dried at room temperature, and then heated and cured at 130° C. for 1 hour to obtain coated films. In either case, adhesion (100/100), scratch resistance (
A), heat resistance (◯), hot water resistance (◯), and dyeability (A) were good.

Example 6 An aluminum plate was washed with A7T and air-dried to a clear υζ state, then dipped in Coating Liquid 5 of Table 1 to be coated with 'C, thoroughly air-dried at room temperature, and then heated at 130°C for 1 hour. Cured by heating.

The obtained coat film had good adhesion (100/100), scratch resistance (A), heat resistance (◯), and hot water resistance (◯).

Example 7 In 163 of Example 1, the fifth disilane compound
A coating composition was prepared in the same manner except that the following disilane compound having the atomic group (1A-) shown in the table was used.

(OEt)asiASl(OEt)z Using the coating composition, coating was performed in the same manner as in the example to form a coating film. The evaluation results of the coated film are also shown in Table 5.

21 Ichito Saakiyama 1 To] Ri- (゛Usuii I) December 1980
Month 2ζI'''11fr:'l Director-General Wakaine Kazuo. l'l's Omote Ko Showa Fi 7th Special Product Risei No. 1'). 12+1fl/J issue 2
．． Master of inventions: Koh S1 Ink River Compound = {. 4 + ('l's bartender special i゛! IQf + people 11 places 11
1-15 Mikage-cho, Toku 111-shi, 1kuchi prefecture, 41-ba Shina (11l)
f. Cao 111 Soda {; 1, j (, Association 71 representative Yasuharu Oto / 1, Urall-. The number of inventions increased from ζ 05, oil 11
In the evening, one elephant was wearing a helmet! IY. 411゜1 of the 4m explanation (j. 冫山 11σ月月郎(1)Special ii'l claims as per the attached sheet.

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Separate 6th shift ``Specification after correction.'1 Scope of claims 1)--D i!5] (. 1≧1,,/1 1I (-1. Nigai Rikijin 0 possession i-
) A disilane compound containing 1-group (Tanoj1haA?; 1/-1 one button or straight li'i'i-shaped ζ containing 1-8 carhones) A bivalent eye consisting of at least 7 or more 1-1 children,
, no.j. l'. ','4 small alkynore sword 5J nor
-1.1 Alkoxyal A・ruj, lJ, R'J (month <'tf same -H, ノ; -L;j゜}'・(which is the alkyl group of 4.1.) as a constituent component Tozuruko Goto, Inkkawa Jun III IV.

(2) -/+yt(.
'CS;:! Carpo name - 1. Group or containing 1,000 F disilanated white matter (ノ, ・TA (C)
l+({4CjKaNaoyu(゜(like a little 1.1<tomo'?
1). 1 or more 1. Q) 14; j1 r1 or I》l, 'f divalent functional group,
- is the same as - 冫1, 7:? l. L-Niko 41CIJ゛no゛bar-nore-group-J, -/;=-t;t-ano Ll-q
RR4 is the same or different 3-alkyl) and an organoalkoxysilane compound represented by the general formula (R6)yt 51 R-St(OR7) 3-n (however,
R5 is a hydrocarbon group, an alkyl group, or an aryl group having one of vinyl group, methacryloxy group, merkabuto group, epoxy group, and amino group as a functional group, R
6 is an alkyl group, n is 0 or l, R7 is an alkyl group or an alkoxyalkyl group) 8 + a tetraalkoxysilane compound represented by the general formula Si(OR)4 (however, R8 is an alkyl group or an alkoxyalkyl group) A coating composition comprising at least one additive selected from colloidal silicone, an epoxy compound, and a melamine derivative.

Claims (1)

[Claims] (1) A disilane compound containing a carbonate group represented by the general formula R2 1 (RIO)B-t8i-A-St(OR2)8-m (wherein A contains a carbonate group and the main chain is linear) a divalent atomic group consisting of at least 7 or more atoms, R1 and R2 are the same or different alkyl groups or alkoxyalkyl groups, R8 and R4 are the same or different alkyl groups, t and m are 0 or 1 ) (2) A disilane compound containing a carbonate group represented by the general formula R2x(R10)B-zsi-A-St(OR2)am (wherein A is a carbonate group) containing a divalent functional group with a linear main chain of at least 7 or more atoms, R1 and R4 are the same or different alkyl groups, t and m are O or 1), and a general formula R 'n I R5Si(OR')s, an organoalkoxysilane compound (however,
R5 is a hydrocarbon group having one of vinyl group, methacryloxy group, mercapto group, epoxy group and amino group as a functional group;
R6 is an alkyl group, n is 0 or 1, R7 is an alkyl group or an alkoxyalkyl group), general formula 81 (
OR8) Tetraalkoxysilane compound represented by 4 (
provided that R8 is an alkyl group or an alkoxyalkyl group), a coating composition comprising at least one additive selected from colloidal silica, an epoxy compound, and melamine U4.