JP2885390B2 - Composition for fiber treatment - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

BACKGROUND OF THE INVENTION 1. Field of the Invention The present invention relates to a composition for treating fibers, and more particularly to imparting good flexibility and smoothness to various fibers and preventing yellowing due to heat of treatment and standing over time. The present invention relates to a fiber treatment composition which can be used.

[0002]

2. Description of the Related Art Conventionally, among various fibers, synthetic fibers such as polyester, acrylic and nylon have been widely used for wadding. Since this application requires excellent flexibility and smoothness, various treatment agents have been proposed separately from the treatment agents for fabrics.

[0003] For example, a treating agent comprising a combination of epoxy siloxane and amino siloxane, epoxy siloxane and amino compound, amino siloxane and epoxy compound (see Japanese Patent Publication No. 48-17541), dimethylpolysiloxane with high polymerization degree and aminoalkoxysilane (See JP-B-51-37996), and a combination of epoxysiloxane and aminoalkoxysilane (see JP-B-53-19715 and JP-B-53-19716).
All of these treating agents can impart good flexibility and smoothness to various fibers, and can impart a feather-like texture of feather touch.

[0004] However, the fiber treated with the above-mentioned treating agent has a drawback that it yellows with heating during the treatment step and with standing over time thereafter. In order to improve the above-mentioned drawbacks, a treating agent obtained by combining an aminosiloxane with an epoxysilane or an epoxy compound (Japanese Patent Laid-Open No. Sho 62
-276090, JP-A-63-75184) and the like. However, although the treatment agent certainly improves yellowing, it has a drawback that the flexibility and smoothness of the fiber are reduced. Therefore, it has been strongly desired to develop a treating agent having excellent flexibility and smoothness while preventing yellowing.

[0005]

SUMMARY OF THE INVENTION Accordingly, an object of the present invention is to minimize the yellowing due to the heat of treatment and standing over time even when various fibers, particularly synthetic fibers for cotton wool, are treated. An object of the present invention is to provide a fiber treatment composition that can impart good flexibility and smoothness.

[0006]

SUMMARY OF THE INVENTION The above objects of the present invention are as follows.
As a main component, (A) 100 parts by weight of an organopolysiloxane compound represented by the following formula (3), and (B) aminoalkoxysilane represented by the following formula (4) can react with an NH group in the aminoalkoxysilane. This is achieved by a fiber treatment composition characterized by containing 1 to 50 parts by weight of a reaction product with a compound as a main component.

[0007]

Embedded image In the formula, R ¹ is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and each R ¹ may be the same or different; X is a hydrogen atom and / or 1 to 1 carbon atoms. 20 represents an unsubstituted or substituted monovalent hydrocarbon group, m represents a rational number of 10 to 10,000, and n represents a rational number of 0 to 100.

[0008]

Embedded image In the formula, R ² and R ³ represent a hydrogen atom and / or a carbon atom having 1 to 20 carbon atoms.
Is an unsubstituted or substituted monovalent hydrocarbon group, and R ² and each R ³ may be the same or different; R ⁴ has 1 carbon atom
10 to 10 unsubstituted or substituted divalent hydrocarbon group, R ⁵ is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, Y is a hydrogen atom and / or an unsubstituted or substituted Substitution 1
Represents a monovalent hydrocarbon group, p is an integer of 0 to 5, q is 0 to 2
Represents an integer.

Specific examples of R ^{1 in} the component (A) include saturated aliphatic hydrocarbon groups such as methyl, ethyl, propyl, butyl, pentyl, octyl, decyl, dodecyl, tetradecyl, octadecyl, and vinyl and allyl. Unsaturated aliphatic hydrocarbon groups, saturated alicyclic hydrocarbon groups such as cyclopentyl and cyclohexyl, aromatic hydrocarbon groups such as phenyl, tolyl and naphthyl, and / or these groups are partially halogen atoms or epoxy And groups substituted with an organic group containing a group or a carboxyl group.

Specific examples of X include the same groups as those described above for R ¹ . m is a rational number of 10 to 10,000, and preferably a rational number of 100 to 1,000. When m is less than 10, the flexibility of the fiber becomes insufficient, and when it exceeds 10,000, the smoothness becomes insufficient.
n is a rational number of 0 to 100, and more preferably 0 to
It is a rational number of 10. If n exceeds 100, both flexibility and smoothness become insufficient.

Specific examples of such an organopolysiloxane compound include the following.

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Next, R ² and R ³ in the component (B) are a hydrogen atom and / or an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and R ² and R ³ are the same. Or different. Specific examples of the monovalent hydrocarbon group include the same groups as those described above for R ¹ . Specific examples of R ⁴ include an alkylene group, an arylene group, an alkenyl group and the like, and particularly preferable examples include a methylene group, a dimethylene group and a trimethylene group.
Specific examples of R ⁵ and Y include the same groups as those for R ¹ .

Specific examples of the aminoalkoxysilane compound in the component (B) include the following.

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In the component (B), the compound which reacts with the NH group present in the aminoalkoxysilane compound is selected from the group consisting of an epoxy compound, a (meth) acrylate, an organic acid (anhydride) and an isocyanate compound. Preferably, at least one compound is used. Specific examples of the above epoxy compound include the following.

[0015]

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Examples of the (meth) acrylate include methyl acrylate, ethyl acrylate, butyl acrylate, 2-ethylhexyl acrylate, dodecyl acrylate, 2-hydroxyethyl acrylate, and other (meth) acrylates. Acrylic esters and the like can be mentioned. Organic acids (anhydrides) include formic acid, acetic acid, propionic acid,
Maleic acid, phthalic acid and the like, and their acid anhydrides and the like can be mentioned.

As the isocyanate compound, tolylene diisocyanate, hexamethylene diisocyanate,
Diphenylmethane diisocyanate, OCNC ₃ H ₆ S
i (OC ₂ H ₅ ) _{3 and the} like. Such various compounds are reacted with the aminoalkoxysilane compound as shown by the following formula to obtain a reaction product.

[0018]

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These reactions are usually carried out at room temperature to 150 ° C.
For 1 to 10 hours. Although the ratio of the starting material to give the component (B) is not particularly limited, from the viewpoint of improving yellowing, the NH group in the aminoalkoxysilane compound is
It is preferable that the total amount of reactive groups such as an epoxy group, an acrylic group, a carboxyl group, and an isocyanate group is 0.5 to equimolar.

In the present invention, the amount of the component (B) must be 1 to 50 parts by weight, preferably 5 to 30 parts by weight, per 100 parts by weight of the organopolysiloxane (A). I do. When the amount of the component (B) is less than 1 part by weight, the flexibility is lowered. When the amount is more than 50 parts by weight, the smoothness is lowered, and in any case, the feeling becomes insufficient.

As described above, the fiber treatment composition of the present invention comprises, as main components, an organopolysiloxane as the component (A), an aminoalkoxysilane as the component (B), and an NH group in the aminoalkoxysilane. And a reaction product of a compound capable of reacting with component (A) and a catalyst for accelerating the reaction between component (A) and component (B), as long as the properties are not impaired. Fiber agents such as anti-wrinkle agents, flame retardants, antistatic agents and the like can also be added.

In treating various fibers with the fiber treating composition of the present invention, the composition is diluted with a suitable solvent to adjust to a desired concentration, or is treated with a surfactant. After emulsifying and dispersing in water to form an emulsion, it is diluted with water, adjusted to a desired concentration, adhered to the fiber by means of dipping, spraying, roll coating or the like, and then dried and heat-treated. The amount of adhesion in this case is not particularly limited, but usually about 0.1 to 5% by weight based on the fiber is sufficient.

Examples of the surfactant used for emulsification include anionic surfactants such as sodium alkyl sulfate and sodium alkylbenzene sulfonate, polyoxyethylene alkyl phenyl ether, polyoxyethylene alkyl ether, sorbitan fatty acid ester and the like. And nonionic surfactants and cationic surfactants such as quaternary ammonium salts. The fibers treated with the fiber treatment composition of the present invention are not particularly limited, and include not only synthetic fibers for cotton filling such as polyester, acrylic and nylon, but also natural fibers such as cotton, wool, hemp and silk. Is also effective.

[0024]

Industrial Applicability The fiber treatment composition of the present invention can not only impart good flexibility and smoothness to fibers by treating various fibers, especially synthetic fibers for wadding, but also provide a treatment. Very little yellowing of the treated fibers due to heat and aging.

[0025]

EXAMPLES The present invention will be described in more detail with reference to the following Examples, but it should not be construed that the invention is limited thereto.

Synthesis Example 1 In a 1-liter flask equipped with a stirrer, a thermometer, a reflux condenser, and a nitrogen gas inlet tube, 103.0 g of N-β- (aminoethyl) γ-aminopropylmethyldimethoxysilane and 195.0 g of butyl glycidyl ether were added. (Equimolar to NH group in aminoalkoxysilane) and isopropyl alcohol 20
0.0 g, while stirring and introducing nitrogen gas,
The reaction was performed at 80 ° C. for 5 hours. After confirming the disappearance of butyl glycidyl ether in the container by gas chromatography, the low boiling point fraction was removed at 80 ° C. for 2 hours under a reduced pressure of 10 mmHg to obtain a viscosity of 20 cs (25 ° C.) and a refractive index of 1.4530 ( 25 ° C.) (hereinafter referred to as B
-1).

Synthesis Example 2 150.0 g of ethyl acrylate in place of the butyl glycidyl ether used in Synthesis Example 1
A reaction product was obtained in the same manner as in Synthesis Example 1 except that (equimolar to NH group in aminoalkoxysilane) was used (hereinafter referred to as B-2).

Synthesis Example 3 Instead of butyl glycidyl ether and isopropyl alcohol used in Synthesis Example 1,
Each of 153.0 g of acetic anhydride (equimolar to NH group in aminoalkoxysilane) and 200.000 of dehydrated toluene.
A reaction product was obtained in the same manner as in Synthesis Example 1 except that 0 g was used (hereinafter, referred to as B-3).

Synthesis Example 4 Except that 370.5 g of isocyanate compound represented by OCNC ₃ H ₆ Si (OC ₂ H ₅ ) ₃ (equimolar to NH group in aminoalkoxysilane) was used instead of acetic anhydride used in Synthesis Example 3 A reaction product was obtained in the same manner as in Synthesis Example 3 (hereinafter referred to as B
-4).

Synthesis Examples 5 and 6 130.0 g of butyl glycidyl ether used in Synthesis Example 1 (equivalent to 0.67 times mol of NH group in aminoalkoxysilane) and 65.0 g
g (e.g. 0.3 for NH group in aminoalkoxysilane)
The corresponding reaction products were obtained in the same manner as in Synthesis Example 1 except that the reaction product was reduced to 3 times the molar amount (hereinafter referred to as B-
5 and B-6).

Synthesis Example 7 The aminoalkoxysilane used in Synthesis Example 2 was γ-aminopropyltriethoxysilane 1
A reaction product was obtained in the same manner as in Synthesis Example 2 except that the amount was changed to 10.5 g (hereinafter, referred to as B-7).

Examples 1 to 8 and Comparative Examples 1 to 3 300 g of the organopolysiloxane represented by the formula
Using 50 g of polyoxyethylene nonylphenyl ether (EO10 adduct) as an emulsifier, the mixture was emulsified and dispersed in 650 g of water using a homomixer to prepare an emulsion (emulsion A-1).

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On the other hand, B-1 to B obtained in Synthesis Examples 1 to 7
-7, 150 g of each reaction product was used as an emulsifier for polyoxyethylene nonylphenyl ether (EO).
Emulsion was prepared by emulsifying and dispersing 25 g of (15 adducts) in 325 g of water (emulsions B-1 to B-1).
7). A treatment bath was prepared with the composition shown in Table 1 for each emulsion, and a polyester staple cotton of 6 denier x 64 mm was immersed. Then, the wet pickup was squeezed to 30% by a centrifugal dehydrator, and then heat-treated at 150 ° C for 20 minutes. Was. The flexibility, smoothness and yellowing of the obtained treated cotton were evaluated according to the following methods and criteria. The results are shown in Tables 1 and 2.

[0034]

[Table 1]

[0035]

[Table 2]

For flexibility and smoothness, touch
Evaluation was made as follows. ：: Feather-like texture with extremely high flexibility and smoothness. Δ: The texture was slightly coarse and inferior in flexibility and smoothness. ×: The texture was coarse and hard, and had no flexibility and smoothness. As for the yellowing, the treated cotton was further heated at 200 ° C. for 30 minutes, and then the degree of yellowing was visually observed and evaluated. ：: No yellowing was observed. Δ: Slightly yellowed. ×: Extremely yellowing was observed.

Comparative Examples 4 and 5. Table 2 except that N-β- (aminoethyl) γ-aminopropylmethyldimethoxysilane and γ-aminopropyltriethoxysilane were each used as a 30% aqueous solution in place of the component B used in the examples.
A treatment bath was prepared in the same manner as in the example with the composition shown in Table 1, and the flexibility, smoothness, and yellowing of the treated cotton when used were evaluated. Table 2 shows the results.

Examples 9 to 16 and Comparative Examples 6 and 7 The same procedure as in Example 1 was repeated except that the organopolysiloxane of the following formula (A) was used instead of the organopolysiloxane of the formula (A). A treatment bath was prepared in the same manner as in the above example with the composition shown in No. 3, and the flexibility, smoothness and yellowing of the treated cotton when used were evaluated respectively (emulsions A-2 to 3). ). Table 3 shows the results.

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[Table 3]

────────────────────────────────────────────────── ─── Continued on the front page (72) Inventor Satoshi Kuwata 1-10 Hitomi, Matsuida-cho, Usui-gun, Gunma Prefecture Inside the Silicone Electronics Materials Research Laboratory, Shin-Etsu Chemical Co., Ltd. (56) References JP-A-2-169773 (JP, A) (58) Field surveyed (Int. Cl. ⁶ , DB name) D06M 13/00-15/72

Claims (2)

(57) [Claims] 1. A reaction between (A) 100 parts by weight of an organopolysiloxane compound represented by the following formula (1) and (B) an aminoalkoxysilane represented by the following formula (2) and a NH group in the aminoalkoxysilane: A fiber treatment composition comprising, as a main component, 1 to 50 parts by weight of a reaction product with a possible compound. Embedded image In the formula, R ¹ is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, and each R ¹ may be the same or different; X is a hydrogen atom and / or 1 to 1 carbon atoms. 20 represents an unsubstituted or substituted monovalent hydrocarbon group, m represents a rational number of 10 to 10,000, and n represents a rational number of 0 to 100. Embedded image In the formula, R ² and R ³ represent a hydrogen atom and / or a carbon atom having 1 to 20 carbon atoms.
Is an unsubstituted or substituted monovalent hydrocarbon group, and R ² and each R ³ may be the same or different; R ⁴ has 1 carbon atom
10 to 10 unsubstituted or substituted divalent hydrocarbon group, R ⁵ is an unsubstituted or substituted monovalent hydrocarbon group having 1 to 20 carbon atoms, Y is a hydrogen atom and / or an unsubstituted or substituted Substitution 1
Represents a valent hydrocarbon group, p represents an integer of 0 to 5, and q represents an integer of 0 to 2. 2. The compound capable of reacting with an NH group in an aminoalkoxysilane is at least one compound selected from the group consisting of an epoxy compound, a (meth) acrylate, an organic acid (anhydride) and an isocyanate compound. The composition for treating a fiber according to claim 1, which is provided.