JPH10331072A - Application of hydrophilicity to hydrophobic synthetic fiber in production of nonwoven fabric by wet process - Google Patents

Abstract

PROBLEM TO BE SOLVED: To produce a wet process nonwoven fabric at a high speed provided with an excellent hydrophilicity, persistency thereof and high-quality, by allowing a water solution of polyether compound containing a specific fatty acid amidic group to adhere to hydrophobic synthetic fiber. SOLUTION: This method is conducted by allowing a water solution of polyether (including also any bases neutralized with acid and any quaternary compounds) containing a fatty acid amidic group shown by the formula [R<1> and R<2> are each an 8-22C fatty acid amidic group when at least one thereof is the 8-22C fatty acid amidic group, or a group of N(A<2> -H)2 (A<2> is a polyalkoxy group wherein 2-4C alkoxy units are repeated and its repeating number is 30 to 130); R3 is H or a 1-3C trialkylsilyl; A<1> is a polyalkoxy group wherein 2-4C alkoxy units are repeated and its repeating number is 30 to 130; (p) is an integer of 1 to 4; (m) and (n) are independently 2 or 3] to adhere to hydrophilic synthetic fiber at 0.03 to 3 wt.% in terms of a polyether compound containing the fatty acid amidic group.

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for imparting hydrophilicity to hydrophobic synthetic fibers in the production of a nonwoven fabric by a wet method. Nonwoven fabrics are manufactured by a wet method from hydrophobic synthetic fibers such as polyester fibers and polyolefin fibers, and are used for sanitary materials and papermaking. When a nonwoven fabric is produced from a hydrophobic synthetic fiber by a wet method, the hydrophobic synthetic fiber is subjected to the following method when it is put into water due to the high quality of the obtained nonwoven fabric and the speeding up of the production process. Is required to have excellent hydrophilicity such that it is quickly dispersed into single fibers,
In addition, it is required to have a durable hydrophilic property so that the dispersion state is stably maintained. The present invention relates to a method for imparting hydrophilicity to hydrophobic synthetic fibers that meets such a demand.

[0002]

2. Description of the Related Art Conventionally, as a method for imparting hydrophilicity to a hydrophobic synthetic fiber, for example, a polyester fiber, there have been various proposals for attaching a hydrophilic polyester having a hydrophilic group introduced into a molecule to the polyester fiber (Japanese Patent Publication No. Sho 45). -10794,
JP-A-60-134071, US Pat. No. 4,410,687).
In particular, as a method for imparting hydrophilicity to polyester fibers in the production of a nonwoven fabric by a wet method, 1) a method of adhering a polyetherester having a polyalkylene glycol ether group in a molecule to polyester fibers (Japanese Patent Laid-Open No. 58-1983).
-208500), 2) A method of attaching a hydrophilic polyester having a sulfonic acid group in a molecule to polyester fiber (Japanese Patent Laid-Open No. 1-298297), 3) A method of attaching a polyether polyol to polyester fiber (Japanese Patent Laid-Open No.
6-169814). However, these conventional methods have a drawback that imparting hydrophilicity to hydrophobic synthetic fibers is inherently insufficient, or that even if the hydrophilicity can be imparted initially, the durability is poor. In the conventional method, when these are applied to the production of nonwoven fabric by the wet method,
When the hydrophobic synthetic fibers are put into water, they do not quickly disperse into single fibers, or once dispersed, the dispersed state is not stably maintained.

[0003]

The problem to be solved by the present invention is that, in the conventional method, the hydrophilicity imparted to the hydrophobic synthetic fiber is originally insufficient or the hydrophilic synthetic fiber is initially imparted with an appropriate hydrophilicity. Even if it can be done, its durability is inferior, so that it is difficult to apply it to the production of a wet nonwoven fabric that requires high quality and high speed.

[0004]

Means for Solving the Problems Thus, the present inventors have
As a result of researching to solve the above-mentioned problems, it has been found that it is correct and suitable to attach an aqueous liquid of a fatty acid amide group-containing polyether compound having a specific structure to a hydrophobic synthetic fiber at a predetermined ratio.

That is, according to the present invention, in the production of a nonwoven fabric by a wet method, an aqueous solution of the following fatty acid amide group-containing polyether compound is added to hydrophobic synthetic fibers in an amount of 0.03 to 3% by weight as the fatty acid amide group-containing polyether compound. The present invention relates to a method for imparting hydrophilicity to hydrophobic synthetic fibers, which is characterized in that the hydrophilic synthetic fibers are attached so as to be hydrophilic. Fatty acid amide group-containing polyether compound: a fatty acid amide group-containing polyether represented by the following formula 1, a fatty acid amide group-containing polyether salt obtained by neutralizing the fatty acid amide group-containing polyether with an acid, and the fatty acid amide group-containing polyether Or two or more fatty acid amide group-containing polyether compounds selected from fatty acid amide group-containing polyether quaternized products obtained by quaternizing with a quaternizing agent

[0006]

(Equation 1)

(In the formula 1, R ¹ , R ² : a fatty acid amide group having 8 to 22 carbon atoms when at least one of them is a fatty acid amide group having 8 to 22 carbon atoms or -N (A ² -H) ₂ The group shown (however, A ² has ² carbon atoms)
A polyalkoxy group composed of repeating alkoxy units of 1 to 4, wherein the number of repeating alkoxy groups is 30.
A 130 polyalkoxy group) R ^3: a trialkylsilyl group having a carbon number of 1 to 3 H or an alkyl group A ^1: a polyalkoxy group consisting of repeating alkoxy units having 2 to 4 carbon atoms A polyalkoxy group in which the repeating number of the alkoxy unit is 30 to 130, p: an integer of 1 to 4, m, n: 2 or 3)

[0008] The fatty acid amide group-containing polyether compound used in the present invention includes 1) a fatty acid amide group-containing polyether represented by Formula 1 and 2) a fatty acid amide group-containing polyether obtained by neutralizing the fatty acid amide group-containing polyether with an acid. Polyether salts; 3) quaternized fatty acid amide group-containing polyethers obtained by quaternizing the fatty acid amide group-containing polyether with a quaternizing agent. In the present invention, one or more of such fatty acid amide group-containing polyether compounds can be used.

The fatty acid amide group-containing polyether represented by the formula 1 is a compound having at least one fatty acid amide group and at least one polyether block in a molecule. Such fatty acid amide group-containing polyether,
Polyalkylene (poly) amine / (poly) obtained by amidation reaction between polyalkylene polyamine and fatty acid
It can be obtained by successively performing ring-opening addition polymerization of an alkylene oxide to an amino group of a fatty acid amide to form a polyether block.

In the fatty acid amide group-containing polyether, the polyalkylene polyamine to be used for synthesis is a linear polyalkylene having 2 to 5 carbon atoms of 2 or 3 carbon atoms and 3 to 6 amino groups. It is an alkylene polyamine. This includes, for example, 1) diethylenetriamine,
Triethylenetetramine, tetraethylenepentamine,
Examples thereof include polyethylene polyamines such as pentaethylenehexamine and 2) polypropylene polyamines such as dipropylenetriamine and tetrapropylenepentamine. Of these, diethylenetriamine and triethylenetetramine are preferable.

In the fatty acid amide group-containing polyether, the fatty acids to be synthesized include 1) caprylic acid, capric acid, lauric acid, stearic acid, behenic acid, and 2
-Saturated fatty acids having 8 to 22 carbon atoms, such as ethylhexanoic acid and isostearic acid; 2) 8 to 2 carbon atoms, such as caproleic acid, myristoleic acid, oleic acid, and erucic acid
And unsaturated fatty acids having 16 carbon atoms.
To 22 saturated fatty acids, and unsaturated fatty acids having 16 to 22 carbon atoms are preferred.

In the fatty acid amide group-containing polyether, the polyalkylene (poly) amine / (poly) fatty acid amide to be used for the synthesis is obtained by an amidation reaction between the above polyalkylene polyamine and a fatty acid.
In such an amidation reaction, the ratio between the polyalkylene polyamine and the fatty acid is a ratio necessary for amidating at least one terminal amino group of the polyalkylene polyamine, but the amino groups at both terminals of the polyalkylene polyamine are amidated. It is preferable to set the ratio.

The polyether containing a fatty acid amide group represented by the formula 1 is a polyalkylene (poly) amine.
It can be obtained by successively addition-polymerizing an alkylene oxide to the amino group of the (poly) fatty acid amide to form a polyether block. Examples of such an alkylene oxide include alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide, propylene oxide, and butylene oxide. Polyalkylene (poly) amine / (poly) fatty acid amides may be added with an alkylene oxide in a random form, a block form, or a mixed form thereof. The block form is preferred. Among them, ethylene oxide is first added, Next, a polyoxyethylene-polyoxypropylene block type to which propylene oxide is added is more preferable. In such a polyoxyethylene-polyoxypropylene block type polyether block, oxyethylene units / oxypropylene units = 25/75 to 50/50.
(Molar ratio) is particularly preferable.

In such a fatty acid amide group-containing polyether, the number of moles of the alkylene oxide added per amino group is from 30 to 130, preferably from 50 to 110.

As described above, the fatty acid amide group-containing polyether represented by the formula (1) is converted into a polyalkylene (poly) amine / (poly) fatty acid amide by an amidation reaction between a polyalkylene polyamine and a fatty acid. Oxide is sequentially addition-polymerized in the presence of a basic catalyst to form a polyether block,
The present invention does not limit the method of the amidation reaction or the sequential addition polymerization, and a known method can be applied thereto.

The fatty acid amide group-containing polyether represented by the formula (1) is obtained by subjecting an amino group of a polyalkylene (poly) amine / (poly) fatty acid amide to sequential ring-opening addition polymerization of an amino group of the polyether block as described above. Can be obtained by further trialkylsilating some or all of the terminal hydroxyl groups of the polyether block to introduce a trialkylsilyl group at the terminal of the polyether block. . Such trialkylsilyl groups include trimethylsilyl, triethylsilyl, tripropylsilyl, and dimethylethylsilyl groups having 1 carbon atom.
Trialkylsilyl groups having an alkyl group of 3 to 3 are exemplified, and among them, a trimethylsilyl group is preferable.

The present invention does not particularly limit the method of trialkylsilylation, and a known method using a silylating agent can be applied. Such silylating agents include:
Trimethylchlorosilane, trimethylmethoxysilane,
Triethylmethoxysilane, trimethylethoxysilane, dimethylethylmethoxysilane, and the like. Although the ratio of the trialkylsilylation of the terminal hydroxyl group of the polyether block is not particularly limited, it is preferable that at least 50 mol% of the terminal hydroxyl group be trialkylsilylated.
More preferably, 0 mol% or more is trialkylsilylated.

The fatty acid amide group-containing polyether compound used in the present invention includes, in addition to the fatty acid amide group-containing polyether described above, a fatty acid amide group-containing polyether obtained by neutralizing the fatty acid amide group-containing polyether with an acid. Ether salts are included.

The fatty acid amide group-containing polyether salt is obtained by neutralizing a part or all of the amino groups in the fatty acid amide group-containing polyether with an organic acid or an inorganic acid. Examples of the organic acid used for neutralization include 1) an aliphatic monocarboxylic acid having 2 to 6 carbon atoms such as acetic acid, propionic acid, and caproic acid; and 2) a carbon atom having 2 carbon atoms such as glycolic acid, lactic acid, and malic acid.
4) aliphatic carboxylic acids having 8 to 12 carbon atoms such as methanesulfonic acid and butanesulfonic acid; 4) aromatic sulfonic acids such as benzenesulfonic acid and naphthalenesulfonic acid; 5) toluene Sulfonic acid, substituted aromatic sulfonic acid substituted with an alkyl group having 2 to 9 carbon atoms such as dodecylbenzene sulfonic acid, 6) methyl acidic phosphate, butyl acidic phosphate,
Examples thereof include alkyl acid phosphates having 2 to 12 carbon atoms such as lauryl acid phosphate. Examples of the inorganic acid used for neutralization include hydrochloric acid, phosphoric acid, phosphorous acid, boric acid and the like. Among them, the acids used for neutralization include aliphatic monocarboxylic acids having 2 to 6 carbon atoms and 2 monovalent carbon atoms.
To 4 aliphatic hydroxymonocarboxylic acids and 2 to 2 carbon atoms
Twelve alkyl acid phosphates are preferred.

In the present invention, the degree of neutralization of the amino group of the fatty acid amide group-containing polyether with an acid is not particularly limited, but usually the amino group in the fatty acid amide group-containing polyether is neutralized by 50 mol% or more. Those can be used to advantage.

The fatty acid amide group-containing polyether compound used in the present invention includes, in addition to the above-described fatty acid amide group-containing polyether and salts thereof, the fatty acid amide group-containing polyether with a quaternizing agent. Graded fatty acid amide group-containing polyether quaternaries are included.

The fatty acid amide group-containing polyether 4
The quaternized product is obtained by quaternizing some or all of the tertiary amino groups in the fatty acid amide group-containing polyether with a quaternizing agent. As the quaternizing agent used for quaternizing, 1)
C1-C8 monohalogenated hydrocarbons such as methyl chloride, ethyl bromide, butyl iodide, and benzyl chloride; 2) C1-C3 dialkyl sulfates of alkyl groups such as dimethyl sulfate and diethyl sulfate; 3) Trimethyl Trialkyl phosphates having 1 to 8 carbon atoms in alkyl groups such as phosphate and tributyl phosphate; and 4) alkylene oxides having 2 to 4 carbon atoms such as ethylene oxide and propylene oxide, among which dialkyl having 1 to 3 carbon atoms. Sulfates and trialkyl phosphates having 4 to 8 carbon atoms are preferred.

The present invention does not particularly limit the quaternization rate of the tertiary amino group in the fatty acid amide group-containing polyether by the quaternizing agent. Those having a quaternary group of 50 mol% or more can be advantageously used.

As described above, the present invention does not limit the method for synthesizing the fatty acid amide group-containing polyether compound used in the present invention, and any known synthesis method can be applied thereto. For example, 1) a polyalkylene polyamine and a fatty acid are converted into a polyalkylene (poly) amine / (poly) fatty acid amide by an amidation reaction, and then a basic catalyst is added to the amino group of the polyalkylene (poly) amine / (poly) fatty acid amide. A method in which an alkylene oxide is sequentially subjected to ring-opening addition polymerization in the presence of a fatty acid amide group-containing polyether, and 2) the fatty acid amide group-containing polyether obtained in the above 1) is modified with a trialkylsilyl agent using a trialkylsilyl agent. 3) dispersing or dissolving the fatty acid amide group-containing polyether obtained in the above 1) or 2) in an aqueous medium, and adding the acid as it is or as an aqueous liquid To obtain a fatty acid amide group-containing polyether salt by neutralization with The fatty acid amide group-containing polyether quaternary is obtained by melting the fatty acid amide group-containing polyether obtained in 2) as it is or dissolving it in an inert medium, adding a quaternizing agent thereto, and performing a quaternization reaction. And a method of forming a compound.

In the present invention, the aqueous solution of the fatty acid amide group-containing polyether compound described above is used as the fatty acid amide group-containing polyether compound on the hydrophobic synthetic fiber in an amount of 0.03.
To 3% by weight, preferably 0.1 to 1.5% by weight. Amount of adhesion to hydrophobic synthetic fiber is 0.0
If the amount is less than 3% by weight, it is difficult to obtain the desired effect stably. Conversely, if the amount exceeds 3% by weight, a corresponding effect cannot be obtained.

According to the present invention, when an aqueous liquid containing a specific organic acid salt in a predetermined ratio in addition to the fatty acid amide group-containing polyether compound described above is adhered to the hydrophobic synthetic fiber, the hydrophobic synthetic fiber Thereby, hydrophilicity having excellent durability can be imparted. Such organic acid salts are one or more organic acid salts selected from an alkylsulfonate salt, an alkyl sulfate salt and an alkyl phosphate salt, each having an alkyl group having 1 to 8 carbon atoms. For example, 1) alkyl sulfonate salts having an alkyl group having 1 to 8 carbon atoms such as methyl sulfonate sodium salt, butyl sulfonate sodium salt, and octyl sulfonate potassium salt; 2) methyl sulfate sodium salt and octyl sulfate potassium salt; Alkyl sulfate salt having an alkyl group having 1 to 8 carbon atoms, 3) 1 to 1 carbon atoms such as methyl phosphate sodium salt, propyl phosphate potassium salt, butyl phosphate potassium salt and octyl phosphate sodium salt
Examples thereof include an alkyl phosphate salt having an alkyl group of 8, and among them, an alkyl phosphate salt having an alkyl group having 1 to 4 carbon atoms is preferable.

When the aqueous liquid containing the fatty acid amide group-containing polyether compound and the organic acid salt is adhered to the hydrophobic synthetic fiber, the ratio of both in the aqueous liquid is 100 parts by weight of the fatty acid amide group-containing polyether compound. The amount of the organic acid salt is 20 to 50 parts by weight, preferably 30 to 40 parts by weight, and the amount of the organic acid salt attached to the hydrophobic synthetic fiber is 0.1% as the fatty acid amide group-containing polyether compound.
It is made to be in the range of 03 to 3% by weight, preferably 0.1 to 1.5% by weight.

Further, according to the present invention, when an aqueous liquid containing a specific sulfonic acid group-containing polyester at a predetermined ratio in addition to the above-described fatty acid amide group-containing polyether compound is attached to hydrophobic synthetic fibers, Hydrophilic fibers having excellent durability can be imparted to the conductive synthetic fibers. Such a sulfonic acid group-containing polyester has a dicarboxylic acid residue and a diol residue as a main structural unit in the molecule, and a dicarboxylic acid residue having a sulfonic acid group as a sub structural unit is 1 to 10 in all the structural units. It is a sulfonic acid group-containing polyester having a number-average molecular weight of 2,000 to 15,000, preferably 3,000 to 10,000, having a molar percentage of sulfonic acid group.

As raw materials for the above-mentioned sulfonic acid group-containing polyester, 1) terephthalic acid, isophthalic acid, orthophthalic acid, which forms a dicarboxylic acid residue;
Dicarboxylic acids such as 2,6-naphthalenedicarboxylic acid, adipic acid, azelaic acid and sebacic acid; lower alkyl esters such as methyl ester and ethyl ester of these dicarboxylic acids; 2) ethylene which forms a diol residue Glycol, propylene glycol, 1,
Diol compounds such as 4-butanediol, neopentyl glycol, diethylene glycol, 1,4-hexanedimethanol, bishydroxyethoxybisphenol A, and 3) 5-sulfoisophthalic acid which forms a dicarboxylic acid residue having a sulfonate group Examples thereof include dicarboxylic acids having a sulfonic acid group such as sodium and sodium 2-sulfoterephthalate, and lower alkyl esters of dicarboxylic acids having these sulfonic acid groups. Sulfonate group-containing polyesters synthesized from these raw materials are known per se, for example,
It can be synthesized by the methods described in JP-A-40873 and JP-B-63-46191.

When an aqueous liquid containing a fatty acid amide group-containing polyether compound and a sulfonic acid group-containing polyester is adhered to hydrophobic synthetic fibers, the ratio of both components in the aqueous liquid is 100%. The content of the sulfonic acid group-containing polyester is 5 to 40 parts by weight, preferably 10 to 30 parts by weight, and the amount of the fatty acid amide group-containing polyether compound is 0.03 to 40 parts by weight. 3
% By weight, preferably 0.1 to 1.5% by weight.

Further, according to the present invention, in addition to the above-described fatty acid amide group-containing polyether compound, an aqueous liquid containing a polyethylene glycol diglycidyl ether cross-linked product of a specific fatty acid / diethylene triamine condensate at a predetermined ratio can be subjected to hydrophobic synthesis. When attached to the fiber, the hydrophobic synthetic fiber can impart hydrophilicity having excellent durability. The polyethylene glycol diglycidyl ether cross-linked product of the fatty acid / diethylene triamine condensate includes 1) a condensation reaction between 2 mol of the fatty acid and 1 mol of diethylene triamine, and 2) a polyethylene glycol diglycidyl ether / 2 mol of the produced fatty acid / diethylene triamine condensate. It is a crosslinked product obtained by the addition reaction of a mole. Examples of the fatty acid as a raw material of the crosslinked product include straight-chain saturated fatty acids having 8 to 22 carbon atoms, such as caprylic acid, capric acid, lauric acid, stearic acid, and behenic acid. Straight-chain saturated fatty acids are preferred. As the polyethylene glycol diglycidyl ether, the number of repeating oxyethylene units constituting the polyethylene glycol chain in the polyethylene glycol diglycidyl ether molecule is from 1 to 15, and preferably from 7 to 13.

The present invention does not particularly limit the method for synthesizing a crosslinked product of a fatty acid / diethylene triamine condensate and polyethylene glycol diglycidyl ether, and a known method can be applied to this. For example, 2 moles of fatty acid and 1 mole of diethylenetriamine are heated and dehydrated to obtain a fatty acid / diethylenetriamine condensate, and 1 mole of polyethylene glycol diglycidyl ether is used for 2 moles of the obtained fatty acid / diethylenetriamine condensate. A crosslinked product can be obtained by performing an addition reaction between an amino group and a glycidyl group of polyethylene glycol diglycidyl ether.

When an aqueous liquid containing a fatty acid amide group-containing polyether compound and a crosslinked polyethylene glycol diglycidyl ether of a fatty acid / diethylene triamine condensate is adhered to hydrophobic synthetic fibers, the ratio of both in the aqueous liquid is as follows: The crosslinked product of the fatty acid / diethylenetriamine condensate is 10 to 50 parts by weight, preferably 20 to 100 parts by weight per 100 parts by weight of the fatty acid amide group-containing polyether compound.
Make up to 40 parts by weight.

In the present invention, the above-described fatty acid amide group-containing polyether compound or the like is used as an aqueous liquid. Such an aqueous liquid can be prepared by mechanically dispersing a fatty acid amide group-containing polyether compound or the like exclusively in water, but in the presence of an auxiliary agent such as a known nonionic surfactant or anionic surfactant. It can also be prepared by mechanically dispersing in water. Such adjuvants include 1) polyoxyalkylene (POA, hereinafter the same) alkyl ether, PO
A nonionic surfactants such as A alkyl phenyl ether and POA alkyl ester; and 2) anionic surfactants such as fatty acid salts, alkyl sulfates, POA alkyl sulfates, alkyl sulfonates, alkyl benzene sulfonates, and alkyl phosphates. The proportion of these auxiliaries is as small as possible within a range of 15% by weight or less based on the fatty acid amide group-containing polyether compound.

The present invention is applied to a hydrophobic synthetic fiber before it is put into water and dispersed in the production of a nonwoven fabric by a wet method. Examples of the adhesion method at the time of application include an immersion method, a spray method, and a roller lubrication method.

Examples of the hydrophobic synthetic fibers to which the method for imparting hydrophilicity of the present invention is applied include polyester fibers, polyamide fibers, polyacrylonitrile fibers, polypropylene fibers, and composite synthetic fibers composed of two or more of these. However, it is particularly effective for polyester fibers or polypropylene fibers. Examples of such polyester fibers include, in addition to polyethylene terephthalate, polybutylene terephthalate, and polyethylene naphthalate, modified polyester fibers such as basic or acidic dyeable polyester fibers, antistatic polyester fibers, and flame-retardant polyester fibers. No. Examples of the polypropylene fibers include polypropylene fibers, modified polypropylene fibers obtained by copolymerizing various monomers, and composite polypropylene fibers of polyethylene and polypropylene.

[0037]

DESCRIPTION OF THE PREFERRED EMBODIMENTS Embodiments of the method for imparting hydrophilicity to hydrophobic synthetic fibers in the production of a nonwoven fabric by a wet method according to the present invention include the following 1) to 24). In any case, an aqueous liquid such as a fatty acid amide group-containing polyether is attached to the hydrophobic synthetic fibers before the hydrophobic synthetic fibers are put into water and dispersed. 1) Fatty acid amide group-containing polyether (P-1) having two oleic acid amide groups and one polyether block composed of a polyalkoxy group having a repeating number of alkoxy unit of 80 in one molecule (details) As described below, R ¹ and R ² in Formula 1 are oleic acid amide groups, A ¹ is a polyalkoxy group having 80 repeating alkoxy units,
R ³ is H, p is 1, m and n are 2), and an aqueous solution of fatty acid amide group-containing polyether (P
(1) A method of adhering so that the ratio becomes 0.5% by weight.

2) Fatty acid amide group-containing polyether (P-2) having two lauric acid amide groups and one polyether block composed of a polyalkoxy group having 60 repeating alkoxy units in one molecule. (In detail, R ¹ and R ² in Formula 1 are lauric acid amide groups, A ¹ is a polyalkoxy group having 60 repeating alkoxy units, R ³ is H, p is 1, m and A method in which n is applied to the polyester-based fibers so that the aqueous liquid of 2) is 1.0% by weight as a fatty acid amide group-containing polyether (P-2).

3) Fatty acid amide group-containing polyether (P-3) having two stearamide groups in one molecule and two polyether blocks composed of a polyalkoxy group having 100 repeating alkoxy units. (As will be described in detail later, R ¹ and R ² in Formula 1 represent a stearamide group, and A ¹ represents a repeating number of an alkoxy unit of 100.
The aqueous liquid having a polyalkoxy group of R, H = ³ , p = 2, m and n = 2) as a fatty acid amide group-containing polyether (P-3) with respect to the polyester-based fiber in a proportion of 0.5% by weight. How to adhere

4) In the above 1), the fatty acid amide obtained by introducing a trimethylsilyl group at the end of the polyether block of the fatty acid amide group-containing polyether (P-1) instead of the fatty acid amide group-containing polyether (P-1). Group-containing polyether (P-4) (as described later in detail,
R ¹ and R ² in the formula 1 represent an oleic acid amide group, A ¹ represents a polyalkoxy group having a repeating number of alkoxy unit of 80, R ³
Is a trimethylsilyl group, p is 1, and m and n are 2).

5) In the above 2), the fatty acid amide obtained by introducing a trimethylsilyl group at the end of the polyether block of the fatty acid amide group-containing polyether (P-2) instead of the fatty acid amide group-containing polyether (P-2). Group-containing polyether (P-5) (as described in detail below,
R ¹ and R ^{2 in} Formula 1 are lauric acid amide groups, A ¹ is a polyalkoxy group having 60 repeating alkoxy units, R ³
Is a trimethylsilyl group, p is 1, and m and n are 2).

6) The fatty acid amide according to 3) above, wherein a trimethylsilyl group is introduced at the end of the polyether block of the fatty acid amide group-containing polyether (P-3) instead of the fatty acid amide group-containing polyether (P-3). Group-containing polyether (P-6) (as described in detail below,
R ¹ and R ² in the formula 1 are stearic acid amide groups, A ¹ is a polyalkoxy group having 100 repeating alkoxy units,
A method wherein R ³ is a trimethylsilyl group, p is 2, m and n are 2).

7) In the above 1), the fatty acid amide group-containing polyether (P-1) is neutralized with acetic acid in place of the fatty acid amide group-containing polyether (P-1). A method using (P-7).

8) In the above 2), the fatty acid amide group-containing polyether (P-2) is neutralized with lactic acid instead of the fatty acid amide group-containing polyether (P-2). A method using (P-8).

9) The fatty acid amide group-containing polyether acetate obtained by neutralizing the fatty acid amide group-containing polyether (P-4) with acetic acid in place of the fatty acid amide group-containing polyether (P-4) in the above item 4). A method using (P-9).

10) In the above 5), the fatty acid amide group-containing polyether (P-5) is neutralized with lactic acid instead of the fatty acid amide group-containing polyether (P-5). A method using (P-10).

11) In the above 6), in place of the fatty acid amide group-containing polyether (P-6), the fatty acid amide group-containing polyether (P-6) is neutralized with an acidic butyl phosphate ester. A method using an ether / butyl phosphate salt (P-11).

12) The fatty acid amide group-containing polyether obtained by quaternizing the fatty acid amide group-containing polyether (P-1) with diethyl sulfate instead of the fatty acid amide group-containing polyether (P-1) in the above 1). Quaternary compound (P-1
Method using 2).

13) The fatty acid amide group-containing polyether obtained by quaternizing the fatty acid amide group-containing polyether (P-2) with benzyl chloride in place of the fatty acid amide group-containing polyether (P-2) in the above item 2). A method using a quaternary compound (P-13).

14) The fatty acid amide group-containing polyether obtained by quaternizing the fatty acid amide group-containing polyether (P-4) with diethyl sulfate instead of the fatty acid amide group-containing polyether (P-4) in the above item 4). Quaternary compound (P-1
Method using 4).

15) The fatty acid amide group-containing polyether obtained by quaternizing the fatty acid amide group-containing polyether (P-5) with diethyl sulfate in place of the fatty acid amide group-containing polyether (P-5) in the above 5). Quaternary compound (P-1
Method using 5).

16) The fatty acid amide group-containing polyether obtained by quaternizing the fatty acid amide group-containing polyether (P-6) with benzyl chloride in place of the fatty acid amide group-containing polyether (P-6) in the above item 6). A method using a quaternary compound (P-16).

17) In addition to the fatty acid amide group-containing polyether (P-1) of the above 1), butyl phosphate potassium salt is added to the fatty acid amide group-containing polyether (P-1) 10
A method in which an aqueous liquid contained at a ratio of 30 parts by weight per 0 parts by weight is attached to polyester fibers so as to have a ratio of 1.0% by weight as a fatty acid amide group-containing polyether (P-1).

18) In the above item 17), a fatty acid amide group-containing polyether (P-4) is used instead of the fatty acid amide group-containing polyether (P-1), and octyl sulfonate potassium salt is used instead of butyl phosphate sodium salt. Method using.

19) The method according to the above item 17), wherein octyl sulfate potassium salt is used instead of butyl phosphate potassium salt.

20) In 18) above, propylene glycol / potassium salt may be used instead of octyl sulfonate potassium salt.
Ethylene glycol / dimethyl adipate / 5-dimethyl sulfoisophthalate sodium salt = 30/20/45
Sulfonic acid group-containing polyester having an average molecular weight of 6000 (IS-
Method using 1).

21) In 17) above, propylene glycol / ethylene glycol / dimethyl adipate / 5-dimethyl sodium 5-sulfoisophthalate / sodium m-sulfobenzoate = 36/14/47. An average molecular weight of 450 obtained by a condensation polymerization reaction at 5/2 / 0.5 (molar ratio).
A method using a sulfonic acid group-containing polyester (IS-2).

22) In 18) above, polyethylene glycol (the number of repeating oxyethylene units is 9) diglycidyl ether is added to 2 mol of a condensate of stearic acid / diethylene triamine = 2/1 (molar ratio) in place of octyl sulfonate sodium salt. A method using a crosslinked product (DE-1) obtained by adding 1 mol of an addition reaction.

23) In 17), polyethylene glycol (the number of repeating oxyethylene units is 9) diglycidyl ether is added to 2 mol of a condensate of behenic acid / diethylenetriamine = 2/1 (molar ratio) in place of the potassium salt of butyl phosphate. A method using a crosslinked product (DE-2) obtained by subjecting 1 mol to an addition reaction.

24) The method according to 1) to 23) above, wherein the fibers are attached to polypropylene fibers instead of polyester fibers.

[0061]

【Example】

Test Category 1 (Synthesis of fatty acid amide group-containing polyether)-Synthesis of fatty acid amide group-containing polyether (P-1) 576 g (2.04 mol) of oleic acid and 103 g (1.0 mol) of diethylenetriamine were charged into a flask.
While maintaining the temperature at 180 ° C., the reaction was carried out for 4 hours while distilling off generated water by a nitrogen gas stream to obtain dioleic amide of diethylenetriamine. When dioleic acid amide of diethylenetriamine was analyzed by potentiometric titration,
The amine value was 91.0 (KOH mg / g). 643.3 g of dioleic amide of this diethylenetriamine
(1.0 mol) and 13 g of potassium hydroxide were charged into an autoclave, purged with nitrogen gas, heated to 120 ° C., and press-fitted with 1408 g (32 mol) of ethylene oxide to cause a reaction. After the aging reaction for one hour, 2900 g (50 mol) of propylene oxide was further injected to cause a reaction. After an aging reaction for one hour, the catalyst was removed by an adsorbent treatment to obtain 4848 g of a reaction product. Analysis of the obtained reaction product revealed that the number of repeating units of two oleic acid amide groups and alkoxyl units in one molecule was 80 and that the ratio of ethoxy units / propoxy units = 40/60 (molar ratio). Fatty acid amide group-containing polyether having one polyether block comprising an alkoxy group (P
-1).

A fatty acid amide group-containing polyether (P-
2) Synthesis of (P-3) and (R-1) to (R-3) Similarly to the fatty acid amide group-containing polyether (P-1), the fatty acid amide group-containing polyether (P-2), (P
-3) and fatty acid amide group-containing polyether (R-1)
To (R-3). These contents are summarized in Table 1.

A fatty acid amide group-containing polyether (P-
Synthesis of 4) 520 g of fatty acid amide group-containing polyether (P-1)
(0.107 mol) was charged into a flask and, while stirring under a nitrogen atmosphere, 11.6 g of trimethylsilane chloride.
(0.107 mol) was added dropwise over 10 minutes, and the reaction was carried out while maintaining the reaction temperature at 30 to 40 ° C. 1 at the same temperature
After aging for a while, the fatty acid amide group-containing polyether (P-
The terminal of the polyether block of 1) was trimethylated. When the obtained terminal trimethylated product was analyzed, 97% of the terminal OH groups of the polyether block were substituted with trimethyl groups and the fatty acid amide group-containing polyether (P-
4).

A fatty acid amide group-containing polyether (P-
5) Synthesis of (P-6) Similarly to the fatty acid amide group-containing polyether (P-4), the fatty acid amide group-containing polyether (P-5), (P-6)
-6) was obtained. These contents are summarized in Table 2.

A polyether salt containing a fatty acid amide group (P
Synthesis of -7) 1.0 g (0.017 mol) of acetic acid and 228.4 g of water were charged into a flask to obtain an aqueous acetic acid solution. 97 g (0.02 mol) of the fatty acid amide group-containing polyether (P-1) was injected thereto with stirring to obtain a 30% aqueous solution of the fatty acid amide group-containing polyether acetate (P-7). When the obtained acetate aqueous solution was analyzed, the amine value was 8.7.
(In terms of solid content), and the degree of neutralization was 75%.

A polyether salt containing a fatty acid amide group (P
-8) Synthesis of (P-11) In the same manner as the fatty acid amide group-containing polyether salt (P-7), the fatty acid amide group-containing polyether salt (P-8)
(P-11) was obtained. These contents are summarized in Table 3.

Synthesis of fatty acid amide group-containing polyether quaternary product (P-12) Fatty acid amide group-containing polyether (P-1) 520 g
(0.107 mol) was charged into a flask and heated to 80 ° C. while stirring under a nitrogen atmosphere, and 16 g of diethyl sulfuric acid was added.
(0.103 mol) was added dropwise over 10 minutes, and the reaction was carried out while maintaining the reaction temperature at 80 to 85 ° C. 1 at the same temperature
After aging for a time, a quaternized product (P-12) of the fatty acid amide group-containing polyether with diethyl sulfate was obtained. When the obtained quaternized product was analyzed, the amine value was 10.3 and the quaternized ratio was 93%.

Synthesis of fatty acid amide group-containing polyether quaternary products (P-13) to (P-16) Fatty acid amide group-containing polyether quaternary products (P-12)
In the same manner as in the above, fatty acid amide group-containing polyether quaternaries (P-13) to (P-16) were obtained. These contents are summarized in Table 4.

[0069]

[Table 1]

In Table 1, R ¹ , R ² , R ³ , A ¹ , m, n, p: symbols corresponding to the symbols in the formula 1, respectively, B: addition form of alkylene oxide is block type * 1: molar ratio

[0071]

[Table 2]

[0072]

[Table 3]

[0073]

[Table 4]

Test Category 2 (Preparation of Aqueous Liquid) Preparation of Aqueous Liquid (WP-1) 450 g of water was charged into a flask, the water temperature was adjusted to 10 to 30 ° C., and the fatty acid amide group-containing polyether (P- 1) 50 g was injected with stirring to obtain an aqueous solution (WP-1) of 10% (wt%, hereinafter the same) of a fatty acid amide group-containing polyether (P-1).

Preparation of aqueous liquids (WP-2) to (WP-16) and (WR-1) to (WR-4) The aqueous liquid (WP-2) was prepared in the same manner as the aqueous liquid (WP-1).
To (WP-16) and (WR-1) to (WR-4). Table 5 summarizes the compositions and the like of these aqueous liquids.

Preparation of aqueous liquid (WP-17) 500 g of a 10% aqueous solution (WP-1) of a fatty acid amide group-containing polyether (P-1) was charged into a flask, and the temperature was adjusted to 10 to 30 ° C while stirring. 150 g of a 10% aqueous solution of butyl phosphate potassium salt was injected to obtain a 10% aqueous solution (WP-17) containing 30 parts of butyl phosphate potassium salt per 100 parts of the fatty acid amide group-containing polyether (P-1). Was.

Aqueous liquids (WP-18) to (WP-23)
Preparation of aqueous solution (WP-1) in the same manner as aqueous solution (WP-17)
8) to (WP-23) were prepared. Table 6 summarizes the compositions and the like of these aqueous liquids.

Test Category 3 (Adhesion of Polyamide Compound Containing Fatty Acid Amide Group to Polyester Fiber and Its Evaluation) Examples 1 to 23 and Comparative Examples 1 to 4 Polyester staple cotton (2.0 denier x 5 mm, degreased) Product) was immersed for 5 minutes in a treatment bath prepared by diluting the aqueous liquid prepared in Test Category 2 with water at a bath temperature of 25 ° C. and a bath ratio of 1:30 so that the bath concentration reached the target amount. It was dehydrated at a rate of 30%, and was used as the following treated cotton for evaluation without drying. The amount of the fatty acid amide group-containing polyether compound adhering to the treated cotton was determined by air-drying the treated cotton and using a Soxhlet extractor to remove methanol / benzene (50/50).
(Volume ratio) It was measured by extraction with a mixed solvent. The evaluation results and the measurement results are shown in Tables 5 and 6.

Evaluation of Initial Dispersibility 70 ml of water (25 ° C.) was placed in a test tube of 2.8 cm in diameter × 20 cm in height, and 0.1 g of sample cotton was gently dropped into the test tube. Inverted twice. The dispersed state of the treated cotton after 10 minutes was visually observed, and its initial dispersibility was evaluated according to the following criteria. ··· Evaluation criteria for initial dispersibility ：: All settled, and no coagulated fiber was observed. ：: All settled, but coagulated fibers were slightly observed. △: Partially floating fibers were observed, or cohesive fibers were clearly observed.

Evaluation of Durability / Hydrophilicity After the initial dispersion was evaluated as described above, the test tube was shaken for 1 minute using a paint shaker (manufactured by Toyo Seiki Seisaku-sho, Ltd.). Then, after allowing to stand for 10 minutes, the state of adhesion of air bubbles to the treated cotton and the amount of sedimentation of the treated cotton were visually observed and evaluated according to the following criteria, and these were used as indicators of durability and hydrophilicity. Evaluation criteria for durability and hydrophilicity depending on the state of air bubbles adhered ◎: No air bubbles are observed ○: Slight air bubbles are observed △: Air bubbles are partially observed ×: Air bubbles are observed throughout the fiber Adhesion is observed. ・ Evaluation of durability and hydrophilicity by sedimentation amount ◎: All fibers settled ○: Very few floating fibers △: Some fibers are floating ×: Half or more fibers are floating doing

[0081]

[Table 5]

[0082]

[Table 6]

In Tables 5 and 6, parts: parts by weight%: weight% A-1: butyl phosphate potassium salt A-2: octyl sulfonate sodium salt A-3: octyl sulfate potassium salt IS-1: propylene glycol / ethylene Glycol / dimethyl adipate / 5-dimethyl sulfoisophthalate sodium salt = 30/20/45/5 (molar ratio) obtained by condensation polymerization reaction, sulfonic acid group-containing polyester having an average molecular weight of 6000 IS-2: propylene glycol / Ethylene glycol / dimethyl adipate / 5-dimethyl sulfoisophthalate sodium salt / m-sulfobenzoic acid sodium salt = 3
Sulfonate group-containing polyester having an average molecular weight of 4500, obtained by a condensation polymerization reaction at 6/14 / 47.5 / 2 / 0.5 (molar ratio) DE-1: stearic acid / diethylenetriamine = 2 /
Crosslinked product obtained by adding 1 mol of polyethylene glycol (the number of repeating oxyethylene units: 9) diglycidyl ether to 2 mol of 1 (molar ratio) condensate DE-2: behenic acid / diethylenetriamine = 2/1
(Molar ratio) 2 mol of a condensate and 1 mol of polyethylene glycol (the number of repetition of oxyethylene unit: 9) diglycidyl ether was subjected to an addition reaction.

Test Category 4 (Adhesion of Polyamide Compound Containing Fatty Acid Amide Group to Polypropylene Fiber and Its Evaluation) Examples 24-46 and Comparative Examples 5-8 Polypropylene staple cotton (1.5 denier × 5 mm,
Degreased product) was immersed for 5 minutes in a treatment bath prepared by diluting the aqueous liquid prepared in Test Category 2 with water at a bath temperature of 25 ° C. and a bath ratio of 1:30 so that the bath concentration reached the target amount. It was dehydrated at a squeezing ratio of 30%, and was used as a treated cotton for the following evaluation without drying. The amount of the fatty acid amide group-containing polyether compound adhering to the treated cotton was determined by air-drying the treated cotton and using a Soxhlet extractor to remove methanol / benzene (50/5).
(0 volume ratio) It measured by extracting with a mixed solvent. The evaluation results and the measurement results are summarized in Tables 7 and 8.

Evaluation of durable hydrophilicity 2,000 ml of water and 2.0 of the treated cotton prepared above
g was placed in a 3 liter beaker having a diameter of 15 cm and a height of 22 cm, and the mixture was stirred at a speed of 900 rpm for 30 seconds using a stirring rod of a 4-blade propeller having a diameter of 5 cm. The liquid was transferred to a bat of 275 mm x 209 mm x 35 mm, and the adhered state of the air bubbles of the treated cotton and the dispersed state of the treated cotton were visually observed and evaluated according to the following criteria, and these were used as indices of durability hydrophilicity. Evaluation criteria for durability and hydrophilicity depending on the state of air bubbles adhered ◎: No air bubbles are observed ○: Slight air bubbles are observed △: Air bubbles are partially observed ×: Air bubbles are observed throughout the fiber Adhesion is observed. ・ Evaluation of durability and hydrophilicity due to dispersibility. ：: No aggregated fiber is observed at all. ○: Aggregated fiber is observed slightly. △: Aggregated fiber is observed clearly.

[0086]

[Table 7]

[0087]

[Table 8]

[0088]

As is clear from the above, according to the present invention described above, when the hydrophobic synthetic fiber is put into water, the hydrophobic synthetic fiber is promptly dispersed into the single fiber, and the dispersion state is maintained stably. Therefore, the present invention can be applied to the production of a wet nonwoven fabric that requires high quality and high speed.

Claims (8)

[Claims] In the production of a nonwoven fabric by a wet method, an aqueous liquid of the following fatty amide group-containing polyether compound is added to hydrophobic synthetic fibers in an amount of 0.03 to 3% by weight as the fatty acid amide group-containing polyether compound. A method for imparting hydrophilicity to a hydrophobic synthetic fiber, characterized in that the hydrophilic synthetic fiber is attached to a surface. Fatty acid amide group-containing polyether compound: a fatty acid amide group-containing polyether represented by the following formula 1, a fatty acid amide group-containing polyether salt obtained by neutralizing the fatty acid amide group-containing polyether with an acid, and the fatty acid amide group-containing polyether One or two or more fatty acid amide group-containing polyether compounds selected from fatty acid amide group-containing polyether quaternized compounds obtained by quaternizing with a quaternizing agent (In Formula 1, R ¹ , R ² : a fatty acid amide group having 8 to 22 carbon atoms when at least one of them is a fatty acid amide group having 8 to 22 carbon atoms, or a group represented by —N (A ² —H) ₂ ) (However, A ² has ² carbon atoms
A polyalkoxy group composed of repeating alkoxy units of 1 to 4, wherein the number of repeating alkoxy groups is 30.
A 130 polyalkoxy group) R ^3: a trialkylsilyl group having a carbon number of 1 to 3 H or an alkyl group A ^1: a polyalkoxy group consisting of repeating alkoxy units having 2 to 4 carbon atoms A polyalkoxy group in which the repeating number of the alkoxy unit is 30 to 130, p: an integer of 1 to 4, m, n: 2 or 3) 2. The fatty acid amide group-containing polyether represented by the formula 1, wherein R ¹ and R ² in the formula 1 are each a fatty acid amide group having 16 to 22 carbon atoms, and A ¹ and A ² when containing 2. A polyalkoxy group having 50 to 110 repeating alkoxy units, wherein the polyalkoxy group has a ratio of ethoxy unit / propoxy unit = 25/75 to 50/50 (molar ratio). The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to the above. 3. A polyether salt containing a fatty acid amide group,
The fatty acid amide group-containing polyether represented by the formula 1 is converted to an aliphatic monocarboxylic acid having 2 to 6 carbon atoms, an aliphatic hydroxymonocarboxylic acid having 2 to 4 carbon atoms, and 2 carbon atoms of an alkyl group.
The product is neutralized with one or two or more acids selected from the group consisting of an alkyl acidic phosphate ester and an alkyl acid phosphate ester.
The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to the above. 4. A fatty acid amide group-containing polyether quaternary compound is obtained by converting a fatty acid amide group-containing polyether represented by the formula 1 into a monohalogenated hydrocarbon having 1 to 8 carbon atoms and a dialkyl having 1 to 3 carbon atoms in an alkyl group. 3. A quaternization agent comprising one or more quaternizing agents selected from sulfate, trialkyl phosphate having 1 to 8 carbon atoms in an alkyl group and alkylene oxide having 2 to 4 carbon atoms.
Or the method for imparting hydrophilicity to hydrophobic synthetic fibers according to 3. 5. An aqueous liquid containing the following organic acid salt in an amount of 20 to 50 parts by weight per 100 parts by weight of the fatty acid amide group-containing polyether compound, is further adhered to the hydrophobic synthetic fiber. 5. The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to 3 or 4. Organic acid salt: one or more organic acid salts selected from alkyl sulfonate salts, alkyl sulfate salts and alkyl phosphate salts, each having an alkyl group having 1 to 8 carbon atoms 6. An aqueous liquid containing the following sulfonic acid group-containing polyester in an amount of 5 to 40 parts by weight per 100 parts by weight of a fatty acid amide group-containing polyether compound, is further adhered to the hydrophobic synthetic fiber. 5. The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to item 3 or 4. Sulfonate group-containing polyester: a dicarboxylic acid residue having a dicarboxylic acid residue and a diol residue as main constitutional units in the molecule, and a dicarboxylic acid residue having a sulfonic acid salt group as a sub constitutional unit in an amount of 1 to 10 mol% in all constitutional units. Having a number average molecular weight of 2,000 to 15,000 7. An aqueous liquid further comprising a hydrophobic synthetic fiber containing the following polyethylene glycol diglycidyl ether crosslinked product of a fatty acid / diethylene triamine condensate at a ratio of 10 to 50 parts by weight per 100 parts by weight of a fatty acid amide group-containing polyether compound. The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to claim 1, 2, 3, or 4. Crosslinked polyethylene glycol diglycidyl ether of fatty acid / diethylene triamine condensate: 8 to 22 carbon atoms
The number of repeating oxyethylene units constituting the polyethylene glycol chain is 1 per 2 moles of the condensation reaction product of the linear saturated fatty acid / diethylene triamine = 2/1 (molar ratio).
Reaction product obtained by addition reaction of 1 mol of polyethylene glycol diglycidyl ether of 8. The method according to claim 1, wherein the hydrophobic synthetic fiber is a polyester fiber or a polypropylene fiber.
The method for imparting hydrophilicity to a hydrophobic synthetic fiber according to 5, 6, or 7.