JPS59182838A - Antistatic composition - Google Patents

Abstract

PURPOSE:The titled composition useful as various kinds of ornaments, signboards, illuminators, etc., having improved permanent antistatic properties, obtained by blending a copolymer of acrylic monomers consisting of methyl methacrylate as a main component and a specific sulfonate with a specified alkylene oxide compound, etc. in a specific ratio. CONSTITUTION:(A) A copolymer of (i) 100pts.wt. acrylic monomers consisting of methyl methacrylate as a main component and (ii) 0.5-15pts.wt. sulfonate shown by the formula I or formula II (R' is 1-18C hydrocarbon; R<2> is H, or methyl; X is 2-4C alkylene oxide; m and n are 0-35; M is alkali metal, ammonium, organic amine salt, or organic quaternary ammonium salt) is blended with (B) 0.3-15pts.wt. alkylene oxide compound shown by the formula R<3>O-(Y)l-R<4> (R<3> is H, hydrocarbon, acryloyl, etc.; R<4> is H, 1-18C alkyl, allyl, aryl, etc.; X is 2-4C alkylene oxide; l is 1-35) and (C) 0-5pts.wt. acidic phosphoric ester, to give the desired composition.

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to an acrylic resin composition having excellent permanent antistatic properties.

Acrylic resin has a reputation for its elegant luster, excellent brightness and weather resistance, good mechanical properties and workability, and is used in a wide range of applications such as signboards, lighting equipment, covers, nameplates, and various decorative items. .

However, since acrylic resin has strong electrostatic properties, it can easily become electrostatically charged due to friction, etc., and dirt and dust may adhere to the surface, spoiling the beautiful appearance, and causing the instrument panel pointers to become misaligned. is causing problems.

In the past, many methods have been proposed for imparting antistatic properties to such acrylic resins, which are easily charged, and can be broadly classified into the following.

1. A method of adding and kneading surfactants, fatty acid esters of polyhydric alcohols, etc.

2. A method of applying a silicone compound, etc. to the surface of a molded product.

3. A method in which a monomer having a hydrophilic group is polymerized into a resin to chemically modify the structure of the resin.

Examples of the above-mentioned first method of adding and kneading surfactants include a method using higher fatty acid monoglyceride (Japanese Patent Application Laid-Open No. 53-112949!') and a method of adding an alkyl jetanolamine derivative ( Tokuko Showa 5
3-21028) etc. have been proposed. However, these methods have the disadvantage that the antistatic effect is easily lost by washing with water or rubbing because the surfactant etc. are not chemically bonded to the acrylic resin, and they also require a large amount of surfactant etc. When kneaded into resin, it not only impairs the mechanical properties of the resin, but also makes it easier for surfactants to bleed onto the resin surface, resulting in stickiness. It has shortcomings.

JP-A-50-109944 describes that an acrylic resin is mixed with a compound having a sulfonic acid group, a polyoxyalkylene glycol, and a phosphite compound to impart antistatic properties. However, the compounds having a sulfonic acid group described in this publication are only exemplified as benzenesulfonic acid and para-toluenesulfonic acid, and these sulfonic acids are not chemically bonded to the acrylic resin and do not bond with the acrylic resin. Because of the poor compatibility of acrylic resins, they have the disadvantage of impairing the surface gloss and transparency, which are the original characteristics of acrylic resins.

In addition, as a method of applying the second silicon-based compound to the surface, for example, a method of applying a partial hydrolyzate solution of ethyl silicate to the surface (Japanese Patent Publication No. 81-6533
Publication No.) etc. have been proposed. This surface coating method has an excellent antistatic effect and can be expected to last long, so it has been put into practical use to some extent, but it requires a process of applying and drying the antistatic agent to the final product, which poses a cost problem. However, it also has the disadvantage that the coating film is damaged due to impact, friction, etc., and the antistatic effect is lost.

As for the third method mentioned above, which chemically modifies the structure of the resin itself, for example, a method of copolymerizing polyalkylene glycol monomethacrylate with an acrylic monomer to impart an antistatic effect (Tokushu Co., Ltd.) Showa 56-18951
Publication No. 6) etc. have been proposed. This method can be expected to prevent elution by chemically bonding a nonionic monomer to the resin, but the antistatic effect is generally low, and if a large amount of nonionic monomer is introduced, the resin will not be leached out. However, this method has the disadvantage that the chemical properties and heat resistance are reduced, and the properties of the agri resin are significantly impaired, and so far, no product that is fully satisfactory has been found using this method.

In view of this situation, the inventors of the present invention have conducted intensive studies on resin compositions that have excellent permanent antistatic properties without impairing the original appearance characteristics of acrylic resins. The inventors have discovered that a composition comprising a copolymer of sulfonate and a small amount of a special sulfonate, containing an alkylene oxide compound, etc. meets this purpose, and has thus arrived at the present invention.

That is, the present invention uses 100 parts by weight of an acrylic monomer mainly composed of methyl methacrylate, and the general formula % formula % (however, the formula medium 1 contains a hydrocarbon group having 1 to 18 carbon atoms,
d is hydrogen or methyl group, X is ammonium carbon number,
sulfonate (A > 0.5-1) represented by an organic heptamine base or an organic quaternary ammonium base)
5 parts by weight of the copolymer with the general formula % Formula %] (In the formula, - represents hydrogen or a hydrocarbon group, represents an acryloyl group, represents methacryloyl+vi, and R4 represents hydrogen or a carbon number of 1 to 18 A compound represented by an aralyl group, an aral group, an aryl group, an aral group, Y is an alkylene group having 2 to 4 carbon atoms, and L is an integer of 1 to 35. The present invention relates to an antistatic resin composition containing 0.8 to 15 parts by weight of (B) and 0 to 5 parts by weight of an acidic phosphoric acid ester.

The acrylic monomer mainly composed of methyl methacrylate used in the present invention refers to methyl methacrylate alone or 50% by weight or more, preferably 70% by weight or more of methyl methacrylate and other copolymerizable vinyl monomers. be.

Examples of copolymerizable vinyl monomers include methacrylic acid esters such as ethyl methacrylate, propyl methacrylate, butyl methacrylate, methyl acrylate, ethyl acrylate, propyl acrylate), etc.
Acrylic acid esters such as butyl acrylate-1, 2-ethylhexyl acrylate, unsaturated carboxylic acids such as acrylic acid, methacrylic acid, maleic acid, itaconic acid, acid anhydrides such as maleic anhydride, itaconic anhydride, etc. - Hydroxyl group-containing monomers such as hydroxyethyl acrylate, 2-hydroxypropyl acrylate, tetrahydrofurfuryl acrylate, monoglycerol acrylate, 2-hydroxyethyl methacrylate, 2-hydroxypropyl methacrylate, tetrahydrofurfuryl methacrylate, monoglycerol methacrylate,
Nitrogen-containing forces such as acrylamide, methacrylamide, acryltritrile, methacrylonitrile, diacetone acrylamide, dimethylaminoethyl methacrylate, etc. 1H
fC, epoxy group-containing monomers such as allyl glycidyl ether, glycidyl acrylate, chrycidyl methacrylate, styrene, styrenic monomers such as α-methylstyrene, ethylene glycol diacrylate, allyl acrylate, ethylene glycol jitteracrylate, allyl Examples include crosslinking agents such as methacrylate, divinylbenzene, and trimethylolpropane triacrylate.

The type and amount of the copolymerizable vinyl monomer can be appropriately selected depending on the properties of the desired antistatic resin.

Furthermore, if necessary, additives such as heat stabilizers, ultraviolet absorbers, colorants, plasticizers, and various fillers may be mixed with the monomers as long as the purpose of the present invention is achieved. It can be used as

Sulfonate salt (A) that can be used in the present invention
As, the following general formula % formula % (wherein 1 represents a hydrocarbon group having 1 to 18 carbon atoms)
2 represents hydrogen or a methyl group, X represents a carbon number of 2, and M represents an alkali metal, ammonium, an organic amine base, or an organic quaternary ammonium base.

For example, it is represented by sodium allylalkylsulfosuccinate, potassium allylalkylsulfosuccinate, sodium methallylalkylsulfosuccinate, potassium methallylalkylsulfosuccinate, and the following formulas (a) to (appetizer).

CJ12-COO(CH2CH20)m-R1CH-C
OOCH2CH=CH2 503M or (a) OaM CH-COO(CH2CH2O)m-R1CH2-CO
OCH2CH=CH2 CH2-COO(CH2CH20)m R4 or
(b) CH2-COOCH
2C=CH2 Ha CH2-COO(CH2CH20)m-R1CH-CO
O(CH2CH20) n-CH2Cf1-=C)I2
OaM CH-Coo(CH2CH20)m-R1CH2-C0
0(CH2CH20) li-C11-CH2CH=C
H2CH2-C00(cH2cH20)CH-COO(
CH2CH20) n-CH2C=CH2CH-COO
(CH2CH20)m-R1CH2-C00(CH2C
H20) n-CH2C=CH2H8 Indicates an alkali metal.
．． It is necessary to contain 5 to 15 parts by weight, preferably 1 to 10 parts by weight.

If the content is less than 0.5 parts by weight, the desired permanent antistatic property cannot be obtained, and if it is contained in excess of 15 parts by weight, the mechanical strength and water resistance of the resulting resin will decrease, resulting in poor practicality. It's not clever because it brings about this. Note that water resistance means that the resin composition does not deteriorate in surface gloss, antistatic property, or transparency when it comes into contact with water.

The alkylene oxide compound (B) that can be used in the present invention has the following general formula [m] 0(Y)L-R4[+n] (where 3 is hydrogen, a hydrocarbon group, or an acryloyl group). or methacryloyl group, R4 is hydrogen or a hydrocarbon group, Y is an alkylene oxide group having 2 to 4 carbon atoms, and t is an integer of 1 to 35. Compounds in which Y is an ethylene oxide group and t is 1 to 23 in the structural formula represented by the above general formula [m'll, such as diethylene glycol, triethylene glycol, polyethylene glycol, polyethylene glycol monoacrylate, polyethylene glycol mono methacrylate, ethyl cellosolve acrylate]・,
Ethyl cellosolve methacrylate, butyl cellosolve methacrylate, methoxypolyethylene glycol monoacrylate, methoxypolyethylene glycol monomer Z acrylate, butoxypolyethylene glycol mononotacrylate, etc., and those with ethylene oxide and 3 to 4 carbon atoms. Compounds containing an alkylene oxide chain, which is a rank copolymer with an alkylene oxide, such as propylene oxide or tetrahydrofuran, and in which the copolymerization ratio of ethylene oxide groups accounts for half or more, can be particularly preferably used.

This alkylenoxide compound (B) has the general formula [II
In the structural formula represented by D, if the number of moles of the alkylene oxide group added is greater than 35, methyl methacrylate is formed in the solid state and is difficult to handle because it is difficult to dissolve even in monomonomers, and the phase with the sulfonate (A) is This is not preferred because the solubility becomes poor and the resulting resin becomes less transparent.

The content of the alkylene oxide compound (B) is 10% of the acrylic monomer component whose main component is methyl methacrylate.
0.3 to 15 parts by weight, preferably 0.5 parts by weight
~10 parts by weight.

If the content is less than 0.3 parts by weight, it is difficult to obtain a resin with excellent transparency and surface gloss, and if the content exceeds 15 parts by weight, heat resistance,
This is not preferable because it may reduce mechanical strength and water resistance or cause stickiness on the resin surface.

The alkylene oxide compound (B) has extremely good affinity for both the methacrylic resin and the sulfonate (A), and by containing it in an appropriate proportion, only the sulpon mm (A>) can be converted into a compound with methyl methacrylate as the main component. It is possible to obtain a methacrylic resin with much better transparency, surface gloss, and antistatic properties than a composition obtained by copolymerizing with an acrylic monomer. ) is 0.3 to 5 parts by weight of the realkylene oxide compound (B) per 1 part by weight of the sulfonate (A). The transparency of the resin is insufficient, and no rough alignment effect is observed, and if the amount is more than 5 times (parts by weight), the mechanical strength and antistatic properties decrease, which is not preferable.

The composition of the present invention is composed of 100 parts by weight of an acrylic monomer containing methacrylate as a main component and a general formula r
0.5 to 15 weight of sulfonate (A) represented by the formula and alkylene oxide compound (B) represented by the general formula [1■]
) 0.8 to 15 parts by weight and optional additives are mixed and dissolved in advance to carry out polymerization.

This polymerization method may be a well-known polymerization method for producing an acrylic resin containing methacrylate-1 as a main component, and can be carried out by bulk polymerization, suspension polymerization, emulsion polymerization, etc. in the presence of a radical polymerization initiator.

Water resistance can be improved by containing acidic phosphate ester (C) in the composition of the present invention. The acidic ester (C) has the general formula [■] 0 1 (RO) 3-9P (OH) q rrv] (wherein R5 is an alkyl group having 1 to 18 carbon atoms, an allyl group,
Aryl group, aralkyl group, acryloxyalkyl group,
methacryloxyalkyl group or its derivative, q
represents 1 or 2), such as monomethyl phosphate, dimethyl phosphate-1-, monoethyl phosphate, dimethyl phosphate, monopropyl phosphate, cypropyl phosphate, monobutyl phosphate, dimethyl Phosphate, monohexyl phosphate, dihexyl phosphate, mono 2-ethylhexyl phosphate, di(2-ethylhexyl) phosphate, monooctyl phosphate, dioctyl phosphate, monodecyl phosphate, didecyl phosphate, monotridecanol phospho-1-, ditridecanol phosphate, monostearyl phosphate, distearyl phosphate, monooleyl phosphate, dioleyl phosphate, monophenyl phosphate, diphenyl phosphate, nonylphenyl phosphate, di(nonylphenyl ) Phosphate, mono(2-
hydroxyethyl) methacrylate phosphate, cy(2
-Hydroxyethyl) methacrylate phosphate, etc., and these monoethyl phosphate, diethyl phosphate, monopropyl phosphate, dipropyl phosphate, monobutyl phosphate, and dibutyl phosphate are particularly preferred. Can be used.

This acidic phosphoric acid ester can be contained in an amount of 5 parts by weight or less, preferably 0 parts by weight or less, based on 100 parts by weight of the acrylic monomer mainly composed of methyl methacrylate.
．． It is desirable to use it in a range of 5 to 5 parts by weight; if it is contained in excess of 5 parts by weight, it is not preferable because it may lower the mechanical strength of the resulting resin or bleed onto the resin surface.

The resin composition containing this acidic phosphoric acid ester is composed of an acrylic monomer containing methyl methacrylate as a main component, a sulfonic acid salt (A) represented by the general formula rI] or Il'II], and a sulfonic acid salt (A) represented by the general formula [11N The alkylene oxide compound (B) shown above, acidic phosphoric acid ester (
C) and other additives, etc. are mixed and dissolved in advance,
It can be obtained by well-known polymerization methods such as bulk polymerization and emulsion polymerization in the presence of a radical polymerization initiator. Among the acidic phosphoric acid esters, polymerizable ones such as mono(2-hydroxyethyl) methacrylate phosphate and di(2-hydroxyethyl) methacrylate phosphate are copolymerized and contained.

The methacrylic resin obtained in this way has excellent antistatic properties without impairing its original characteristics such as transparency, surface gloss, mechanical properties, weather resistance, and processability. It has characteristics. Moreover, its antistatic effect shows excellent performance in that A2 hardly changes when washed with water or by friction, and hardly changes even when changed over time, making it extremely practical.

The present invention will be explained in more detail with reference to Examples below.
The present invention is not limited to these examples. Note that parts in the examples indicate parts by weight.

Example 1 100 parts of methyl methacrylate, 2 parts of sodium allyltridecyl sulfosuccinate, and 5 parts of polyethylene glycol having a molecular weight of 4.00% were mixed and dissolved at room temperature, and then 0.2 parts of lauroyl peroxide was added as a polymerization initiator. part was added. This mixed solution was poured into an H1 combining cell consisting of a polyvinyl chloride casket and two glass plates, and heated and polymerized at 67°C for 6 hours and then at 110°C for 1 hour to obtain a resin plate with a thickness of 3 layers. .

The obtained resin plate was subjected to the following tests, and compared with a general methacrylic resin plate (Sumipex 000, manufactured by Sumitomo Chemical Co., Ltd.), and its barrier properties are shown in Table 1.

(1) Antistatic O surface specific resistance: Under standard conditions of 23°C and 150% humidity 3
After being left for a day, measurements were taken using a Kyokucho insulation meter (manufactured by Toa Denpa Kogyo, model 5H-1QE) in the same atmosphere.

◎ Half-life: After applying a voltage IQKV in the same atmosphere as in ◎ using a static honest meter (manufactured by Tsuruga Shokai), the applied voltage was set to zero and the time until the electrostatic voltage was reduced by half was measured.

(2) Transparency Total light transmittance and haze value were measured in accordance with AS TMD-100B.

From Table 1, it can be seen that it has excellent transparency and is generally much better in preventing banding than methacrylic resin plates.

The thermal deformation temperature ri (AST?) of the obtained resin plate.
vi-D648) is 100°C1 tensile fracture strength (
(according to ASTM-D638) is 7; 31 Kg/
cA, and the heat resistance of general methacrylic resin board is 11,
It did not impair mechanical properties.

Furthermore, the obtained resin plate was subjected to an accelerated weather resistance exposure test at 63°C for 11,000 hours using a Nanshine Weather Meter (manufactured by Suga Shiki@Ki), but even after the test, the surface resistivity remained 4.0 x 1010Ω, half reduced. There was almost no change in the antistatic effect after a period of 1 second, and it was highly practical.

Example 2 100 parts of methyl methacrylate, 2 parts of sodium allyl lauryl sulfosuccinate, 5 parts of polyethylene glycol having a molecular weight of 200, and JR5 which is an acidic phosphoric acid ester.
After mixing and dissolving 1 part of 04 (1f1. manufactured by Kita Kagaku Kogyo, a mixture of monobutyl phosphate and diphthyl phosphate) at room temperature, the polymerization initiator and lauroyl peroxide 02
of S
A resin plate with a thickness of 0.3 mm was obtained.

The obtained resin plate is colorless and has a good surface gloss.
The physical properties of the resin plate measured in the same manner as in Example 1 were as follows: total light transmittance: 929%, haze value: 0.3%, and surface resistivity: 8.
5X], 0 Ω, and a half-life of 1 second, it had excellent transparency and antistatic properties.

In addition, the resulting resin plate was immersed in water at 30°C for 2 days, then air-dried, and its transparency and antistatic properties were measured to determine its water resistance. Value o5%,
The surface resistivity was 9.0 x 1.0 Ω, the half-life was 1 second, and both transparency and antistatic properties hardly changed even when immersed in water.

Examples 3 to 11, Comparative Examples 1 to 5 Except for blending sulfonic acid salt (A), alkylene oxide compound (B), and acidic phosphate ester (C') with 100 parts of methyl methacrylate as shown in Table 2. Polymerization was carried out in the same manner as in Examples 1 and 2 to obtain a 3-inch thick wood.

Transparency, frost prevention, mechanical strength, and
Water resistance was measured in the same manner as in Examples 1 and 2, and the results are shown in Table 3.

＼ ＼ ＼ ＼8, ＼-1゜ゝ, ＼＼ ′１ ＼□ ゛-″＼ (1) Water resistance measurement method After soaking in water at 30'C for 2 days and air drying, transparency and electrostatic charge were measured. The preventive properties were measured.

Examples 12 to 20 A sulfonate (A), an alkylene oxide compound (B), and an acidic phosphoric acid ester (
Polymerization was carried out in the same manner as in Examples 1 and 2, except that C) and C) were blended as shown in Table 4.

\ \, \ \\2, \ \, \ \, @Table 4 *Monomer (A) CH2C00 (CH2Cl-I20)9C12H25■
to aOBS-CH-COOCH2CH=CH2C)
12-C00(CH2C00(20)4ct2H25@
Na03S-CH-COOCH2C=CH2" H8 CH2-C00(CH2CH20)9C4H7 ■ ■ KO35-CH-C00(CH2CH20)9
CH2CI4=Qi2 The transparency, antistatic properties, mechanical strength, and water resistance of the obtained resin plate were measured in the same manner as in Examples 1 and 2, and the results are shown in Table 5.

Example 21 To 100 parts of a monomer consisting of 97 parts of methyl methacrylate and 1 to 3 parts of ethyl cellosolve methacrylate, 2.5 parts of a monomer (A) represented by the formula %, ethylene oxide, and tetrahydrofuran were added. are randomly copolymerized in a ratio of 55:45 with 3 parts of polyalkylene glycol monomethacrylate of molecule Q 800, and after dissolving at room temperature, 0.1 part of Abhis isobutyronitrile is added as a polymerization initiator. 70° in the same manner as in Example 1.
The resin was polymerized by heating at 110° C. for 5 hours and then for 1 hour to obtain a resin plate with a thickness of 3 mm.

The obtained resin plate is colorless and transparent, and has a surface resistivity of 8.5x1
It had an excellent antistatic property with a resistance of 0.010Ω and a half-life of 2 seconds.

In addition, the heat deformation temperature (A, STh←D6
48) is 96°C1 tensile breaking strength (ASTM-D
688) was 725 positive/-, which did not impair the heat resistance and mechanical properties of general methacrylic resin plates.

Example 22 100 parts of a monomer consisting of 98 parts of methyl methacrylate and 2 parts of tetrahydrofurfuryl methacrylate, 2.5 parts of potassium allyl lauryl sulfosuccinate and a molecular weight of 20
After mixing and dissolving 0 polyethylene glycol and 1 part of JP-504 (manufactured by Shinka Kagaku Kogyo, a mixture of monobutyl phosphate and dibutyl phosphate), 0.2 part of lauroyl peroxide was added as a polymerization initiator. However, the resin plate obtained by polymerizing in the same manner as in Example 1 was colorless and transparent, and the surface resistivity measured in the same manner as in Example 1 was 1.4 × 10100, the half-life was 1 second, and it had excellent antistatic properties.

In addition, the resulting resin plate was immersed in water at 30°C for 2 days, then air-dried, and its transparency and antistatic properties were measured to determine its water resistance. Value 0.8%
, a surface resistivity of 4×10 10 Ω, a half-life of 1 second, good transparency and liquid even when immersed in water, and excellent durability of the antistatic IE effect.

(35 completed) Procedural amendment July (voluntary) February 1980 Kazuo Wakasugi, Director General of the Japan Patent Office 1981 Patent Application No. 57688n: 2, Name of the invention Static protection Ll: Sexual composition Item 3 Amendment'z-ti-relationship with JJf (/I- Person's address for patent use)
5-5 Kitahama, Higashi-ku, Osaka Name (209) Takeshi Hijikata, 71, Representative of Sumitomo Chemical Co., Ltd.
Claims column of the specification and Detailed Description of the Invention column 6, same as MJ Masaru 1) Claim 4 will be amended as shown in the attached sheet.

2) Details;:; 'j'a Page 4, lines 18 to 19
Starting from the second line, "Japanese Unexamined Patent Publication No. 53-112949" is changed to "q\i Unexamined Japanese Patent Publication No. 53-12949 J.

3) Specification: 1. On page 5, line 14, the word ``compound'' is replaced with ``J'' for compound.

4) Akira (0-kichi ISS Negative from the 3rd line to the F to the 2nd line, ``t is a positive number from 1 to 35'' is changed to ``t
The number average is 1 to 35.

5) In the specification, page S9, line 4-f), line 5 of ``[methyl methacrylate 1°1 override-1'' has been changed to ``
Methyl methacrylate alone” is corrected.

6) Details - page 9, line 5 to line 6 T”F
Insert "," after "50 tons% or more".

7) In the 7th line of the 9th detailed statement, the phrase ``vinyl monomer monomer'' has been changed to ``base base with vinyl monomer, H<.

8) The four rRxJs in formula (a) and formula (bl) on page 13 of the specification are corrected to rRJ.

9) The four "R1" in formula (C) and formula (d') on page 13 of the specification are corrected to "R".

lO) In the third line of page 13 of the specification, "R1 in the formula is" is corrected to "R in the formula is."

11) Insert "," after "=05-15 Juitabe" on page 14, line 3 of the specification.

12) Akane 1m, page 14, line 19 to line 20, L
``t is an integer from 1 to 35'' is changed to ``t is an integer of 1 to 35''.
~35''.

13) Moe Seibou - Page 16, line 1I - 1-0.3 to 15NMjjt part from 1-0.3 to 15NMjjt section from page 16 to line 12 - followed by ``,''
Push in.

14); Chikarahoiwa: “Methacrylate” in the bottom row of the 17th member
The text has been corrected to read ``Nozurmekkrylate.''

15) From the 1st line to the 2nd line ζ of page 22 of the fy3 elegance book, amend it to ``Sumipex 0OOJ to Iruwo [Sumipex (F) 000''.

16) Page 14, line 3r of the specification! in “JR504j
There is a certain thing [JP 504. Correct it with J.

Claims (1) 100 parts by volume of an acrylic monomer containing methyl methacrylate as a main component, expressed by the general formula % [] (However, in the formula, R1 represents a hydrocarbon group having 1 to 18 carbon atoms.
R2 is hydrogen f or a methyl group, X is an alkylene oxide having 2 to 4 carbon atoms, m and n are number average O"35
M is an alkali metal, ammonium,
Amine base, or organic quaternary ammonium base
sulfonate m (A) 0.5-15
Copolymer with N side part, general formula % formula % [ (wherein R is hydrogen or a hydrocarbon group, or an acryloyl group or methacryloyl group, R4 is hydrogen or an alkyl group having 1 to 18 carbon atoms, Allyl group, aryl group, aralkyl group; B) 03~
An antistatic resin composition comprising 15 parts by weight of phosphoric acid, and 0 to 5 parts by weight of acidic phosphoric acid ester (C).

(2-sulfonic acid '181 (A) to the fullylene oxide compound (B) in a weight ratio of 0.3 to 5) .

(3) Sulfonate or general formula [English] or [111
Debosashi'1. In the structural formula, X or ethylene tetra-
1 id group and M is an alkali metal. ,
d) J child is now of course.

(4) B-reactive phosphoric acid ester Hyj (R'0
)3 q P (O) i) q i: ] (f kodashi, in the formula, R5 is an alkyl group having 1 to 18 carbon atoms, an allyl group,
Aryl group, aralkyl group, acryloxyalkyl group,
A meccryloxyalkyl group or a derivative thereof, q
indicates 1 or 2) and contains 0.5 to 5 parts by weight of 1) to 10-1 parts of an acrylic monomer component containing methyl tutacrylate as a main component. A composition according to claim 1, 2 or 3.

Claims (4)

[Claims] (1) Acrylic monomer whose main component is methyl methacrylate 1oo! fit part and general formula % formula % [ (However, in the formula, 1 represents a hydrocarbon group having 1 to 18 carbon atoms,
R2 represents hydrogen or a methyl group, X represents a carbon group, ammonium, an organic amine base, or an organic quaternary ammonium base) Sulfonate (A) 0.5 to
Copolymer with 15 parts by weight, general formula % formula % [] (However, in the formula, 8 represents hydrogen, a hydrocarbon group, an acryloyl group, or a methacryloyl group, and R4 represents hydrogen or an alkyl group having 1 to 18 carbon atoms. group, allyl group, aryl group, aralkyl group, Y represents a C2-C4 realkylene oxide group, t represents an integer of 1-35) (B) 0.3
~15 parts by weight, and acidic phosphate ester (C) 0-5
An antistatic resin composition consisting of parts by weight. (2) The composition according to claim 1, wherein the weight ratio of the alkylene oxide compound (B) to 1 of the sulfonate (A) is 0.3 to 5. (3) The sulfonate has the general formula [I] or rlI]
3. The composition according to claim 1 or 2, wherein in the structural formula represented by, X is an ethylene oxide group and M is an alkali metal. (4) Acidic phosphoric acid ester has the general formula [■]0 (RO)3-q P (OH)(l [■1 (However, in the formula, R5 is an alkyl group, allyl group, or aryl group with 1=18 carbon atoms) , an aralkyl group, an acryloxyalkyl group, a methacryloxyalkyl group or a derivative thereof,
q is 1 or 2), and contains 0.5 to 5 M parts per 100 M parts of an acrylic monomer component containing methyl methacrylate as a main component. , the composition according to item 2 or 3.