JPS6028951B2 - Antistatic agent for synthetic fibers - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION The present invention relates to a specific phosphate ester [compound A] and a specific 3
The present invention relates to an antistatic agent for synthetic fibers comprising a salt of an amino group-containing polymer [Compound B].

The phenomenon in which synthetic fiber products are charged with static electricity and the various adverse effects caused by this charging have been known for a long time. For example, when sewing textile products, you may be shocked by static electricity,
We often experience phenomena such as a drop in work efficiency due to the adhesion of lint, or, in a familiar example, the phenomenon of a shirt clinging to a person when taking it off, or a crackling discharge.

Conventionally, to prevent this type of charging, surfactants, quaternary
A well-known method is to treat fibers with chemicals whose main ingredients are grade ammonium salts, acrylic acid ester derivatives, guandine hydrochloride, aluminum chloride, lithium chloride, etc.
Until now, there has been no chemical used for antistatic treatment of synthetic fibers that satisfies the following conditions.

○｝Do not change the texture of textile products.

{2) Even a small amount added has a large antistatic effect.

Do not impair the abrasion fastness of dyed fabric.

'4' It has good stability in combination with finishing agents used in combination, especially with fluorine-based water-repellent and oil-repellent agents, and has an antistatic effect without reducing the effects of fluorine-based water-repellent and oil repellent properties. What can be granted. [5] Do not induce rust on processing machines, sewing machines, etc.

The present inventors have found that a composition comprising the following phosphate ester [Compound A] and the following salt of a tertiary amino group-containing polymer with a phosphoric acid compound [Compound B] is an antistatic agent that satisfies the above conditions. This discovery led to the present invention.
This is very surprising. This is because Compound A itself does not show much antistatic effect, and Compound B
This is because, although the antistatic effect of the tertiary amino group-containing polymer, which is an intermediate thereof, is not so great, the antistatic effect was dramatically improved by using Compound A and Compound B together. . According to the present invention, "general formula: RIR2R or 04 (wherein RI represents an alkyl group having 1 to 4 carbon atoms, R2 and R2 are respectively a hydrogen atom, an ammonium group,
It represents an alkali metal atom or an alkyl group having 1 to 4 carbon atoms.

) and (wherein R4 represents a hydrogen atom or a methyl group, R5 represents an alkylene group having 2 to 4 carbon atoms, and R6 and R7 have 1 to 4 carbon atoms) represents an alkyl group, and n is 3
The above is preferably an integer of 5 to 3000.

) and the general formula: R8R9HP04 (wherein R8 represents a hydrogen atom, an ammonium group, an alkali metal atom or an alkyl group having 1 to 4 carbon atoms, and R9 represents a It represents an ammonium group, an alkali metal atom, or an alkyl group having 1 to 4 carbon atoms.

) [Compound B] is an antistatic agent for synthetic fibers.

Here, as compound A, for example, triester phosphate such as trimethyl phosphate, triethyl phosphate, triisopropyl phosphate, tributyl phosphate, monomethyl ester phosphate, monoethyl ester phosphate, monoisopropylester phosphate, Phosphate monoesters such as phosphate monobutyl ester, phosphate esters such as phosphate dimethyl ester, phosphate diethyl ester, phosphate dipropylester, phosphate dibutyl ester, or ammonium salts and lithium salts of these phosphoric acid partial esters , sodium salt, potassium salt, etc. Examples of the polymer constituting the main part of compound B include homopolymers or copolymers such as dimethylaminoethyl methacrylate, dimethylaminoethyl acrylate, diethylaminoethyl methacrylate, diisopropylaminoethyl methacrylate, and dimethylaminoptyl methacrylate. It will be done.

In some cases, the homopolymer may have an appropriate amount of "carbon-hydrogen residue not containing a tertiary amino group" introduced into the molecular chain, and a monomer providing such a carbon-hydrogen residue may be introduced into the molecular chain.
Examples include acrylic acid, methacrylic acid, ethyl acrylate, butyl acrylate, methyl methacrylate, styrene, and vinyl acetate.

These tertiary amino group-containing polymers can be easily synthesized by polymerizing the monomers exemplified above by conventional radical polymerization means in the presence or absence of a solvent.

In addition to the phosphoric acid partial ester and its salt listed above as an example of compound A, examples of the phosphoric acid compound with the →cross formula: R8R9HP04 that form a salt with the tertiary amino group-containing polymer include Examples include potassium dihydrogen, ammonium dihydrogen phosphate, and monosodium hydrogen phosphate.

Compound B can be easily obtained by mixing the polymer and the phosphoric acid compound.

However, in some cases, compound B may be obtained by adding part or all of the phosphoric acid compound during polymerization of the tertiary amino group-containing polymer. The antistatic agent of the present invention contains Compound A and Compound B in a ratio of 10 parts by weight of the former to 0.1 parts by weight of the latter.
It is easily prepared by simply mixing ~20 parts by weight, preferably 1 to 1 part by weight.

The antistatic agent of the present invention is applied to textile products by preparing a treatment according to a conventional method.

The composition of the treatment case is usually as follows. In the above-mentioned treatment, the textile product is soaked and squeezed, and an antistatic agent is applied in a solid content of 0.01 to 5% by weight based on the weight of the dry fiber, and then dried.

When a fluorine-based water repellent and oil repellent is used together, 150
Heat treatment at ~180°C. However, the antistatic agent of the present invention may also be diluted with a diluent and applied by spraying directly onto the textile. The antistatic agent of the present invention is an excellent antistatic agent even in a small amount, and does not coagulate and precipitate even when used in combination with a yellowtail shark oil agent.

In addition, it does not adversely affect the color fastness to rubbing and does not cause rust on processing machines or sewing machines. Even when the antistatic agent of the present invention is used in combination with a fluorine-based twill water repellent, sufficient performance in twill water resistance, vertical oil resistance, and antistatic properties can be stably obtained. Containing polymer (
For example, when a mixture of a dimethyl acid cationized product of dimethylaminoethyl methacrylate polymer is used in combination with a fluorine-based hydrophobic oil agent, the antistatic properties may be poor even if the water repellency and hydrophobicity are sufficient. Conversely, when antistatic properties are good, water repellency and oil repellency are often insufficient. The present invention will now be described in detail by way of practice, in which all amounts of treating agents used are expressed in parts by weight.

Moreover, the performance test was conducted by the following method. o Antistatic property: Frictional charging voltage V was measured using a Kyoto University Kaken type rotary static tester.

Friction cloth: Nylon taffeta; 2P, measured in an atmosphere of 65% RH.Color fastness to dyeing: Measured with a JIS L-1048 Gakushin type friction tester.Rust occurrence: Insects on test cloth treated with antistatic treatment. Drive in 12 pins (solvent and cleaning agent) and leave in an atmosphere of 20 qo and 95% RH or higher for 10 days.

Evaluation is based on the number of rusted insect pins. o Freshness: JIS
Measured by spray method using L-1004 Oil permeability: AA
Measured by TCC method. Bending resistance: Handrometer method (1 arc in slit,
2000, measured in an atmosphere of 65% RH) Example An antistatic agent consisting of monophosphate and a salt of a tertiary amino group-containing polymer was prepared as shown in Table 1.

Table 1 Composition of antistatic agent These antistatic agents were used to prepare a treatment bath, and a polyester processed fabric was immersed in this treatment bath and squeezed with a mangle to a squeezing rate of 9% by weight.
00 for 2 minutes.

Table 2 shows the treatment bath formulation and the performance of the processed textile products.
Shown below. Table 2 As shown in Table 2, the antistatic agent of the present invention has a higher antistatic effect than the use of isopropyl acid phosphate sodium salt alone or the isopropyl acid phosphate salt of dimethylaminoethyl methacrylate weight alone. It can be seen that the dyeing properties are extremely excellent, and there is no decrease in color fastness to rubbing and no occurrence of rust.

Example 2 Antistatic agents consisting of butyl acid phosphate potassium salt and butyl acid phosphate salt of dimethylaminoethyl methacrylate weight or butyl acid phosphate salt of dimethylaminoethyl methacrylate/methacrylic acid coweight are shown in Table 3. It was prepared as follows.

Table 3: Antistatic Agent Formation Using this antistatic agent, treatments were prepared as shown in Table 4, and textile products were obtained in the same manner as in Example 1.

This performance is shown in Table 4. Table 4 As shown in Table 4, Compositions W and W have excellent antistatic properties, do not adversely affect color fastness to rubbing, and do not cause rust or change in texture.

Example 3 An antistatic agent comprising sodium salt of isobutyl acid phosphate and isobutyl acid phosphate salt of heavy weight of jetylaminoethyl methacrylate was prepared as shown in Table 5.

Table 5: Antistatic Agent Composition This composition was used in combination with a fluorine-based water/oil repellent agent, and the processing conditions were adjusted as shown in Table 6 to perform water/oil repellent and antistatic treatment on polyester fabrics.

The processing conditions were as follows: polyester cloth was soaked in a process, squeezed with a mangle to a squeezing rate of 85%, dried at 100oo for 2 minutes, and then
7000 for 1 minute. Table 6 shows the performance of this textile product. As shown in Table 6, when the composition is used in combination with a fluorine-based hydrochloric oil agent, excellent antistatic properties can be imparted to the hydrochloric acid oil. Table 6 Loss Dick Guard A-16 Manufactured by Dainippon Ink Chemical Co., Ltd. Examples of fluorine-based water-repelling oil agent 4 Dimethyl phosphate sodium salt 10 parts and dimethyl of dimethylaminoethyl methacrylate polymer (Mw = 2000) A treatment case was prepared as shown in Table 7 using an antistatic agent (composition material) consisting of 2 parts of phosphate salt.

Using this processing procedure, a textile product was obtained in the same manner as in Example 1. This performance is shown in Table 7. As shown in Table 7, the composition dishes exhibit excellent antistatic effects even when used in small amounts.

Table 7

Claims (1)

[Claims] 1 General formula: R^1R^2R^3PO_4 (in the formula, R^
1 represents an alkyl group having 1 to 4 carbon atoms, and R^2 and R^3 each represent a hydrogen atom, an ammonium group, an alkali metal atom, or an alkyl group having 1 to 4 carbon atoms. ) Phosphate ester [Compound A] and general formula: ▲ Numerical formula, chemical formula, table, etc. ▼ (In the formula, R^4 represents a hydrogen atom or a methyl group, and R^5 represents a carbon atom number of 2 to 4 represents an alkylene group, R^6 and R^7 represent an alkyl group having 1 to 4 carbon atoms, and n is an integer of 3 or more.) A polymer containing a tertiary amino group represented by and general formula: R^8R^9HPO_4 (in the formula, R^8 is a hydrogen atom,
Ammonium group, alkali metal atom or 1 carbon atom
-4 alkyl group, and R^9 represents an ammonium group, an alkali metal atom or an alkyl group having 1 to 4 carbon atoms. ) An antistatic agent for synthetic fibers comprising a salt with a phosphoric acid compound [Compound B].