JPH05230769A - Method for providing surface of hydrophobic synthetic fiber with hydrophilic nature - Google Patents

Abstract

PURPOSE:To provide a method for supplying the surface of hydrophobic synthetic yarn with hydrophilic nature wherein hydrophobic synthetic yarn is furnished with high initial water dispersibility and its excellent durability. CONSTITUTION:(A) A specific graft polyether ester and/or graft polyether ester amide and (B) a specific nitrogen-containing compound are used in a ratio of the component A/B=95/5-50/50 (weight ratio) in amounts to give 0.1-3wt.% total pick-up based on the hydrophobic synthetic yarn to treat hydrophobic synthetic yarn.

Description

Detailed Description of the Invention

[0001]

FIELD OF THE INVENTION The present invention relates to a method for imparting hydrophilicity to the surface of a hydrophobic synthetic fiber. Hydrophobic synthetic fibers, including polyester fibers, have excellent economic properties in addition to excellent physical and chemical properties, and are therefore widely used for clothing, bedding, industrial use, etc. .. In recent years, application development that takes advantage of its advantages has been actively carried out, and as one of them, it is required that the fiber surface have excellent hydrophilicity such as sanitary materials and papermaking. Applications are increasing. Among them, in the production of wet non-woven fabrics, which are typically used for papermaking, in order to improve the quality of products and speed up the papermaking process, when the fibers are put into water, they are quickly dispersed into single fibers, and It has been required to have excellent hydrophilicity so that it can be stably maintained. The present invention relates to a method for imparting hydrophilicity to the surface of a hydrophobic synthetic fiber, which meets such a demand.

[0002]

2. Description of the Related Art Hitherto, as a method for imparting hydrophilicity to the surface of a hydrophobic synthetic fiber, the following method of treating the surface of the hydrophobic synthetic fiber with various hydrophilic compounds has been proposed.
For example, regarding polyester fibers, 1) Examples using hydrophilic polyesters having various hydrophilic groups introduced (Japanese Examined Patent Publication No. 45)
-10794, JP-A-60-134071, USP44
10687), 2) an example in which a hydrophilic polyester is used in combination with another water-soluble polymer (JP-A-57-112411, JP-A-60-146081), and 3) an example in which a hydrophilic polyester is used in combination with a reactive compound. (JP-A-61-2978,
JP-A-62-162077), 4) An example in which a hydrophilic polyester and an anionic surfactant are used in combination (JP-B-47-
2512, JP-A-51-26400) and the like. Further, particularly for polyester fibers for wet non-woven fabrics, 1) an example using a polyether ester having a polyalkylene glycol ether group (JP-A-58-208500),
2) Examples using a hydrophilic polyester having a sulfonic acid group (JP-A-1-298297), 3) Examples using a polyether polyol (JP-A-56-169814) and the like. Further, for example, for acrylic fibers, an example using polyalkylamino acrylate (Japanese Patent Laid-Open No. 60-8105).
There is 2).

However, these conventional methods have the drawback that the hydrophilicity is not sufficiently imparted from the beginning, or the hydrophilicity is imparted at the beginning, but the durability is poor. In the conventional method, when these are applied to, for example, the production of a wet non-woven fabric, when the surface-treated hydrophobic synthetic fibers are put into water, they are not immediately dispersed into single fibers or the dispersion state is not stably maintained.

[0004]

The problem to be solved by the present invention is that, in the conventional method, the hydrophilicity is originally insufficient, or even if the hydrophilicity can be imparted at the beginning,
It is inferior in its durability.

[0005]

However, the present inventors have
As a result of research to solve the above problems, a specific grafted polyether ester and / or a grafted polyether ester amide, and a specific nitrogen-containing compound,
It has been found that the method of treating the hydrophobic synthetic fiber is properly suitable by using each of them in a predetermined ratio and using the total amount of these adhering to a predetermined amount.

That is, in the present invention, the grafted polyether ester and / or the grafted polyether ester amide of the following A and the nitrogen-containing compound of the following B are
/ B = 95/5 to 50/50 (weight ratio), and the total adhesion amount of these is 0.1 to 3 with respect to the hydrophobic synthetic fiber.
The present invention relates to a method for imparting hydrophilicity to a surface of a hydrophobic synthetic fiber, which comprises treating the hydrophobic synthetic fiber so as to be used in a weight percentage.

A: one or more selected from the following A-1 polyether esters and the following A-2 polyether ester amides A-1; 8 aromatic or saturated aliphatic dicarboxylic acids;
A vinyl monomer was graft-polymerized to a polyether ester obtained from a dicarboxylic acid containing 5 mol% or more or an ester-forming derivative thereof, a glycol, and a polyether compound selected from polyether monool and polyether diol. Grafted polyetheresters A-2; aromatic or saturated aliphatic dicarboxylic acid 9
A polycarboxylic acid obtained by containing 0 mol% or more of a dicarboxylic acid or an ester-forming derivative thereof, an amide-forming compound selected from diamines, lactams and aminocarboxylic acids, and a polyether compound selected from polyether monools and polyether diols Grafted polyetheresteramides obtained by graft-polymerizing vinyl monomers onto etheresteramides

B: One or more selected from nitrogen-containing compounds having one or more ammonium groups and two or more hydrocarbon groups having 12 or more carbon atoms in the molecule.

The aromatic or saturated aliphatic dicarboxylic acid that constitutes the grafted polyether ester of A-1 is 1) terephthalic acid, isophthalic acid, orthophthalic acid, 2,6-naphthalenedicarboxylic acid, etc. 2) saturated aliphatic dicarboxylic acids such as 2) adipic acid, azelaic acid, and sebacic acid.

The glycol which constitutes the grafted polyether ester of A-1 is 1) ethylene glycol, 1,2-propylene glycol, 1,
4-butanediol, neopentyl glycol, 1,6
-Aliphatic glycols such as hexanediol, 2) cyclohexanedimethanol, alicyclic glycols such as 2,2'-bis (4-hydroxycyclohexyl) propane,
3) A glycol containing an aromatic group such as 2,2 '-{bis (4-hydroxyethoxyphenyl)} propane and 2,2'-{bis (4-hydroxypropoxyphenyl)} methane, 4) Diethylene glycol, dipropylene Aliphatic ether glycols such as glycols may be mentioned.

The polyether compound which constitutes the grafted polyether ester of A-1 is selected from polyether monool and polyether diol. Such polyether monools include 1) polyether monools obtained by adding an alkylene oxide having 2 or 3 carbon atoms to an aliphatic monohydric alcohol such as methanol, butanol, octyl alcohol, stearyl alcohol, 2) phenol, Polyether monools obtained by adding an alkylene oxide having 2 or 3 carbon atoms to a monovalent phenol such as t-butylphenol, dibutylphenol, nonylphenol and β-naphthol, 3) monovalent alicyclic ring such as cyclohexanol and benzyl alcohol Polyether monool obtained by adding alkylene oxide having 2 or 3 carbon atoms to group alcohol or monovalent aromatic alcohol, 4) secondary amine such as diethylamine, dibutylamine, dioctylamine, diphenylamine, morpholine Carbon atoms 2 or 3
5) Polyether monools obtained by adding alkylene oxides of 5), and 5) Polyether monools obtained by adding alkylene oxides having 2 or 3 carbon atoms to mercaptans such as octyl mercaptan, lauryl mercaptan and thiophenol. .. The polyether monool preferably has a molecular weight of 500 to 8,000, more preferably 800 to 5,000.

As the polyether diol, 1)
Polyethylene glycol, polypropylene glycol,
Aliphatic polyalkylene glycol such as polytetramethylene glycol, 2) Polyether diol obtained by adding alkylene oxide having 2 or 3 carbon atoms to the above-mentioned aliphatic glycol, alicyclic glycol or aromatic glycol, 3) A polyether diol obtained by adding an alkylene oxide having 2 or 3 carbon atoms to an aliphatic primary amine can be mentioned. The polyether diol preferably has a molecular weight of 400 to 6000,
Those of 0 to 4000 are more preferable.

As the vinyl monomer which constitutes the grafted polyether ester of A-1, 1) aromatic vinyl monomers such as styrene and α-methylstyrene,
2) Acrylic acid or methacrylic acid esters such as methyl acrylate, methyl methacrylate, ethyl acrylate, butyl methacrylate, 2-ethylhexyl methacrylate, 3) α, β-unsaturated carboxylic acid such as acrylic acid, methacrylic acid, maleic anhydride or Anhydrides thereof, 4) Water-soluble vinyl monomers such as acrylonitrile, acrylamide, 2-hydroxyethyl methacrylate and methoxypolyoxyethylene methacrylate, 5) 3
-Anionic monomers such as sulfopropyl methacrylate sodium salt and styrene sulfonic acid sodium salt, and the like.

In the grafted polyether ester of A-1, the polyether ester portion contains 85 mol% of the above-mentioned aromatic or saturated aliphatic dicarboxylic acid.
It is obtained by polycondensation of the above-mentioned dicarboxylic acid or its ester-forming derivative, the above glycol, and the above polyether compound. in this case,
As the dicarboxylic acid, it is possible to use a dicarboxylic acid having an ionic group in an amount of 15 mol% or less, preferably 3 to 13 mol%. Examples of the dicarboxylic acid having an ionic group include those having a sulfonic acid group such as sodium 5-sulfoisophthalate, sodium sulfoterephthalate, and 4-sodiumsulfonaphthalene-2,6-dicarboxylic acid. Sodium 5-sulfoisophthalate is preferred.

In the grafted polyether ester of A-1, the composition ratio of the above glycol and the above polyether compound is not particularly limited,
Glycol / polyether compound = 90 / 10-50 /
50 (molar ratio) is preferable, and 85 / 15-60
It is more preferable that the ratio is / 40 (molar ratio). Also A-1
In the grafted polyether ester of, the composition ratio of the block portion of the polyether compound to the polyether ester portion is 50 to 95% by weight of the whole.
Is preferable, and more preferably 60 to 90% by weight. In the grafted polyether ester of A-1, the polyether ester portion usually has an average molecular weight of 1,000 to 100,000, but it is preferably 2,000 to 15,000.

The grafted polyether ester of A-1 is obtained by graft-polymerizing the above-mentioned vinyl monomer onto the polyether ester portion as described above, usually in the presence of a radical catalyst. The amount of the vinyl monomer used here depends on its type and the structure of the polyether ester portion graft-polymerized, but is preferably 2 to 50% by weight in the grafted polyether ester. It is more preferable to set the content to ˜30% by weight.

Examples of the aromatic or saturated aliphatic dicarboxylic acid which constitutes the grafted polyetheresteramides of A-2 include those mentioned above for A-1. In this case, it is preferable that aromatic dicarboxylic acid / aliphatic dicarboxylic acid = 100/0 to 15/85 (molar ratio), and 100/0 to 30/70.
(Mole ratio) is more preferable.

The amide-forming compound which constitutes the grafted polyether ester amides of A-2 is
It is selected from diamines, lactams and aminocarboxylic acids. Such amide-forming compounds include 1)
Aliphatic diamines such as hexamethylenediamine and nonamethylenediamine, 2) 4,4′-diaminodiphenyl ether, 4,4′-diaminodiphenylmethane, 4,4 ′
-Aromatic diamines such as diaminodiphenyl sulfone and 4,4'-diaminodiphenyl sulfide, 3) lactams such as ε-caprolactam and ω-laurolactam, and 4) 1.
Examples thereof include aminoalkanecarboxylic acids such as 1-aminoundecanecarboxylic acid and 6-aminohexanecarboxylic acid. Among them, hexamethylenediamine and ε-caprolactam are advantageous.

As the polyether compound which constitutes the grafted polyetheresteramides of A-2, those mentioned above for A-1 can be mentioned. In this case, among the polyether compounds, the polyether monool preferably has a molecular weight of 500 to 8000, more preferably 800 to 5000.
The polyether diol has a molecular weight of 400 to 6
000 is preferable, and 1000 to 4000 is more preferable.

The vinyl monomer which constitutes the grafted polyether ester of A-2 is A-1.
The above-mentioned can be mentioned.

The grafted polyether ester amides of A-2 are dicarboxylic acids containing 90 mol% or more of the above-mentioned aromatic or aliphatic dicarboxylic acids or ester-forming derivatives thereof, amide-forming compounds and polyether compounds. It is obtained by the reaction with. In this case, as the dicarboxylic acid, a dicarboxylic acid having an ionic group in the range of 10 mol% or less can be used.
Examples of the dicarboxylic acid having such an ionic group include A-
The above-mentioned one is mentioned.

In the grafted polyether ester amides of A-2, the composition ratio of the amide-forming compound and the polyether compound is not particularly limited, but the amide-forming compound / polyether compound is not particularly limited. = 20/80 to 80/20 (molar ratio) is preferable, and 35/65 to 65/35 (molar ratio) is more preferable. In the grafted polyether ester amides of A-2, it is preferable that the composition ratio of the block portion of the polyether compound to the polyether ester amide portion is 50 to 95% by weight, and 60 to 90% by weight. More preferably. And in the grafted polyetheresteramides of A-2, the polyetheresteramide moiety is usually
An average molecular weight of 1,000 to 100,000 is used,
It is preferable to use those of 2000 to 20000.
It is more preferable to use those of 000 to 15,000.

The grafted polyetheresteramides of A-2 are those obtained by graft-polymerizing the above-mentioned vinyl monomer onto the above-mentioned polyetheresteramide moiety, usually in the presence of a radical catalyst. The amount of the vinyl monomer used here depends on the kind thereof and the structure of the polyether ester amide moiety for graft polymerization of the vinyl monomer, but it is 3 to 3 in the grafted polyether ester amides.
It is preferably 50% by weight, more preferably 5 to 30% by weight.

The nitrogen-containing compound of B has at least one ammonium group and at least two hydrocarbon groups having 12 or more carbon atoms in the molecule. Examples of the nitrogen-containing compound include a compound represented by the following formula 1, an acid neutralized product of the compound represented by the following formula 2, and a divalent reactive compound containing at least 2 mol or more of the compound represented by the following formula 2. And a salt or a salt thereof produced by condensation using.

[0025]

[Formula 1]

In the formula 1, R ¹ and R ^{2 have} an aliphatic hydrocarbon group having 12 to 22 carbon atoms, an alkanoylaminoethyl group having an alkanoyl group having 12 to 22 carbon atoms, and an alkanoyl group having 12 to 22 carbon atoms. Alkanoylaminopropyl group, or hydroxy (poly) alkoxyalkyl group having an alkoxy group having 2 or 3 carbon atoms and an alkyl group R ³ , R ⁴ : hydrogen, an alkyl group having 1 to 4 carbon atoms or an aralkyl group X: anionic group

[0027]

[Formula 2]

In the formula 2, R ^{5 to} R ⁸ : at least two are alkanoyl groups or alkenoyl groups having 12 to 22 carbon atoms, the rest are hydrogen or alkyl groups having 1 to 4 carbon atoms, and amino groups At least one is a free primary or secondary amino group a: an integer of 2 to 5 b: an integer of 2 to 4

Examples of the compound represented by the formula 1 are 1) dilong-chain alkyl (or alkenyl) ammonium compounds such as dilauryldimethylammonium chloride and distearyldimethylammonium methylsulfonate, 2) dilaurylmethylamine acetic acid salt, and diamine. Stearylamine
Inorganic or organic acid salts of di-long-chain alkyl (or alkenyl) amines such as p-toluene sulfonate, 3) di (ethylenetriamine distearylamide / acetate, dipropylenetriamine distearylamide / acetate, etc. Examples thereof include salts of N-diacylaminoalkyl) amine, and acetates of ethylene oxide adducts of diethylenetriamine distearylamide.

As the acid neutralized product of the compound represented by the formula 2, a partially acylated polyalkylene polyamine such as triethylene tetramine distearyl amide octyl phosphate salt, tetraethylene pentamine distearyl amide acetic acid salt and the acid can be used. Examples include neutralized products.

The divalent reactive compound for condensing at least 2 mol or more of the compound represented by the formula 2 is 1
What is necessary is just to react with a secondary or secondary free amino group to condense and form at least 2 mol or more of the compound represented by the formula 2. Examples of such a divalent reactive compound include:
1) diepoxy compounds such as ethylene glycol diglycidyl ether, diethylene glycol diglycidyl ether, polyethylene glycol diglycidyl ether,
2) Diisocyanate compounds such as tolylene diisocyanate and methylenebisphenyl isocyanate; 3) Alkylene carbonate compounds such as ethylene carbonate and propylene carbonate; 4) Epichlorohydrin and urea.

It is also possible to use those obtained by condensation-forming at least 2 mol or more of the compound represented by the formula 2 by using the above-mentioned divalent reactive compound, but these may be further added with an inorganic acid or an organic acid. Neutralized with
Alternatively, a compound in which the tertiary amino group is converted to a quaternary ammonium salt by using an appropriate quaternization reagent can be used. Among these, as the nitrogen-containing compound of B, it is advantageous to use a neutralized product of a partially acylated polyalkylene polyamine and an acid.

In the present invention, the hydrophobic synthetic fiber is treated with the grafted polyether ester and / or grafted polyether ester amide of A and the nitrogen-containing compound of B. In this case, the usage ratio of A and B is A / B
= 95/5 to 50/50 (weight ratio), preferably 9
It is set to 0/10 to 55/45 (weight ratio). This is to obtain desired hydrophilicity and its durability.

Further, in the present invention, A and B are used so that the total amount of them is 0.1 to 3% by weight, preferably 0.2 to 1.5% by weight, based on the hydrophobic synthetic fiber. .. If the total amount of adhesion is less than 0.1%, it is difficult to obtain a stable effect, and conversely, if it exceeds 3% by weight, the corresponding effect cannot be obtained.

In the practice of the present invention, the grafted polyetheresters and / or grafted polyetheresteramides of A are preferably used as an aqueous dispersion or aqueous solution. When preparing an aqueous dispersion, a dispersant can be used supplementarily. As such a dispersant,
1) Polyoxyethylene (hereinafter abbreviated as POE) alkyl ether, POE alkylphenyl ether, P
Nonionic surfactant such as OE alkyl ester, 2) alkyl sulfate, POE alkyl sulfate, alkyl sulfonate, alkyl benzene sulfonate,
Examples thereof include anionic surfactants such as alkyl phosphates and POE alkyl phosphate salts. The proportion of these dispersants used is preferably 15% by weight or less based on A. When preparing the aqueous dispersion or aqueous solution of A, an organic solvent may be appropriately used in combination. Similarly, the nitrogen-containing compound of B can also be used as an aqueous dispersion or an aqueous solution. When an aqueous dispersion or aqueous solution is prepared, the solid content concentration is usually 1 to 20% by weight, preferably 3 to
It can be used at 15% by weight, which can be further diluted with water.

In the present invention, the grafted polyether ester of A and / or the grafted polyether ester amide and the nitrogen-containing compound of B may be used separately to treat the hydrophobic synthetic fiber. Alternatively, these may be simultaneously used to treat the hydrophobic synthetic fiber. When these are used separately, it is possible to treat with A and then with B. However, after treating with B first, for example through a drying step, then treating with A preferable.

The present invention can be applied in the manufacturing process and processing process of hydrophobic synthetic fibers. It can be applied to the raw yarn that has been subjected to the spinning process or the drawing process of the hydrophobic synthetic fiber, or can be applied to the post-processing of the raw yarn, for example, the spinning process. Examples of the application method include a dipping method, a spray method, a roller lubrication method and the like.

As the hydrophobic synthetic fibers to which the present invention can be applied, in addition to polyester fibers, polyamide fibers, polyacrylonitrile fibers, polypropylene fibers and the like, there are composite fibers formed by using two or more of these fibers in various shapes. Can be mentioned. Among them, polyester fibers are remarkably effective when the present invention is applied. Such polyester fibers include polyethylene terephthalate, polybutylene terephthalate, polyethylene naphthalate, and the like,
Polyester fibers such as polyethylene terephthalate / polyethylene isophthalate, polyethylene terephthalate / polybutylene terephthalate, and modified polyester fibers obtained by copolymerizing various monomers for various purposes,
Examples include basic or acid dyeable polyester fibers, antistatic polyester fibers, flame-retardant polyester fibers and the like.

[0039]

【Example】

Test Category 1 (Synthesis of A) -Synthesis of grafted polyether ester (A-1a) 91 parts of dimethyl terephthalate (parts by weight, the same applies hereinafter), 10 parts of dimethyl isophthalate, ethylene glycol 68
Part, polyethylene glycol 40 having an average molecular weight of 3100
3 parts, and 0.15 parts of manganese acetate tetrahydrate as a catalyst,
After charging 0.05 part of antimony trioxide, transesterification was performed at 150 to 230 ° C. under a nitrogen gas stream, and after distilling off a predetermined amount of methanol, 0.035 part of phosphorous acid was added, and 27
Gradually reduce the pressure while raising the temperature at 0 ° C for 2 hours,
Finally, polycondensation was carried out at 270 ° C. for 40 minutes under a reduced pressure of 1 mmHg. The average molecular weight of the obtained polyether ester in terms of polystyrene by GPC is 9500.
Met.

90 parts of the polyether ester obtained above was melted at 170 to 180 ° C., and 10 parts of polyoxyethylene (6 mol) nonylphenyl ether sulfate ammonium was dissolved in 900 parts of water at 30 ° C. in a solution. Then, the mixture was added with stirring with a homomixer to obtain a stable aqueous dispersion having a polymer concentration of 9%. Then, 1055 parts of this aqueous dispersion, 3.6 parts of methyl methacrylate, and 1.4 parts of methacrylic acid were charged into a flask, and the temperature was raised to 70 ° C. with stirring while substituting with nitrogen. Then, 0.1 part of benzoyl peroxide was further added, the reaction was continued for 4 hours and then cooled to room temperature to obtain the grafted polyether ester (A
-1a) was obtained as an aqueous dispersion containing 9.4% by weight.

Grafted polyether ester (A-1
An aqueous dispersion containing the grafted polyether ester (A-1b, A-1c) was obtained in the same manner as in the case of a). The contents are shown in Table 1.

Synthesis of grafted polyether ester amide (A-2a) 58 parts dimethyl terephthalate, 1 dimethyl isophthalate
0 parts, polyethylene glycol 5 with an average molecular weight of 1500
25 parts, ε-caprolactam 34 parts, and manganese acetate tetrahydrate 0.10 part as a catalyst, antimony trioxide 0.0.
Charge 3 parts, heat at 160-230 ° C. under a nitrogen gas stream, distill off a predetermined amount of methanol, and then add phosphorous acid 0.02
4 parts were added and polycondensation was carried out at 270 ° C. for 60 minutes. The average molecular weight of the obtained polyether ester amide in terms of polystyrene by GPC was 7,500.

Using the polyether ester amide obtained above, the grafted polyether ester amide (A-2a) is contained in an amount of 9.3% by weight as in the case of the grafted polyether ester (A-1a). An aqueous dispersion was obtained.

An aqueous dispersion containing the grafted polyether ester amides (A-2b, A-2c) was obtained in the same manner as in the case of the grafted polyether ester amides (A-2a). The results are shown in Table 1.

[0045]

[Table 1]

In Table 1, 1): polyether ester moiety or polyether ester amide moiety 2): graft polymerized vinyl polymer moiety 3): dicarboxylic acid, 3) -1; terephthalic acid,
3) -2; isophthalic acid, 3) -3; adipic acid, 3)
-4; sodium 5-sulfoisophthalate 4): glycol, but 4) -1; ethylene glycol, 4) -2; 1,4-butanediol 5): polyether compound, but 5) -1; average Polyethylene glycol having a molecular weight of 1500, 5) -2; polyethylene glycol having an average molecular weight of 3100, 5) -3:
Polyoxyethylene monophenyl ether having an average molecular weight of 3500 5) -4; bisphenol A ethylene oxide adduct having an average molecular weight of 1100 6): an amide-forming compound, provided that 6) -1; hexamethylenediamine, 6) -2; -Caprolactam 7): vinyl monomer, provided that 7) -1; methyl methacrylate, 7) -2; styrene, 7) -3; methacrylic acid, 7) -4; polyoxyethylene (4 mol) methacrylate 3) To 7) in the table: Mol% * 1: Polyalkylene glycol content (% by weight) based on the polyether ester portion or polyether ester amide portion * 2: Grafted polyether ester or grafted polyether ester amide Vinyl polymer part content (% by weight)

Test Category 2 (Treatment of hydrophobic synthetic fibers and evaluation thereof) Examples 1 to 8 and Comparative Examples 1 to 9 Described in Table 2 and Table 3 using the aqueous dispersions obtained in Test Category 1 A diluted water dispersion having a composition of 1% by weight of solid content was prepared. Polyester staple cotton (2.0 denier x 5 mm, degreased) is added to this diluted water dispersion at a bath ratio of 30: 1.
To obtain a sample cotton having a target adhesion amount of solid content of 0.3% by weight and a squeezing ratio of 30%. This sample cotton was subjected to the following evaluation without drying. The results are shown in Table 4.

Evaluation of initial dispersibility 70 ml of water (25 ° C.) was put into a test tube having a diameter of 2.8 cm and a height of 20 cm, 0.1 g of cotton sample was gently dropped into the test tube, and the test tube was stoppered. Gently inverted twice. The dispersed state of the cotton after 10 minutes was visually evaluated according to the following criteria.

.. Criteria for judging initial dispersibility ⊚: all settled and no aggregated fibers observed at all ∘: all settled, but a few aggregated fibers observed Δ: some floating fibers observed, or Agglomerated fibers are clearly observed. X: Floating fibers or agglomerated fibers are remarkably large.

Evaluation of Durability After evaluating the initial dispersibility as described above, the test tube was shaken for 1 minute with a paint shaker (manufactured by Toyo Seiki Seisakusho Co., Ltd.).
The air bubble adhesion to cotton after 10 minutes and the settling amount of cotton were visually determined according to the following criteria.

.. Criteria for air bubble adhesion ◎: No air bubble adhesion is observed ○: Slight air bubble adhesion is observed △: Some air bubble adhesion is observed ×: Air bubble adhesion to the entire fiber Is recognized

.. Criteria for determining the amount of sedimentation ◎: All fibers have sedimented ○: Very few fibers are floating △: Some fibers are floating ×: More than half of the fibers are floating

[0053]

[Table 2]

[0054]

[Table 3]

In Tables 2 and 3, A-1a to A-2c; those described in Table 1 B-1; Acetate of ethylene oxide (5 mol) adduct of diethylenetriamine distearylamide, B-2;
Triethylene tetramine distearyl amide acetate, B
-3: Acetate of a reaction product of diethylenetriamine distearylamide (2 mol) and epichlorohydrin (1 mol) D-1: Polyoxyethylene (6 mol) nonylphenyl ether sulfate ammonium, D-2: Polyoxyethylene (4 Mol) lauryl ether sulfate triethanolamine E; lauroylaminopropyltrimethylammonium chloride, F; stearylamine ethylene oxide (12 mol) adduct, G; distearylphosphate N
a salt, H; polyoxyethylene (10 mol) nonylphenyl ether A, B and other values in the table:% by weight

[0056]

[Table 4]

Test Category 3 (Preparation of Spray Liquid and Treatment and Evaluation of Polyester Staple Cotton) Preparation of Second Liquid (Spray Liquid Containing A) Using the aqueous dispersion obtained in Test Category 1, Table 5 and A second liquid having the composition and solid content concentration shown in Table 6 was prepared.

Preparation of First Liquid (Spray Liquid Containing B) Using a nitrogen-containing compound, a first liquid having the composition and solid content concentration shown in Tables 5 and 6 was prepared.

Examples 9 to 16 and Comparative Examples 10 to 15 With respect to the polyester staple cotton used in the test section 2,
The first liquid described in Table 5 and Table 6 was wet picked up 3
The oil was sprayed so that the amount became 0% by weight. Continued Table 5
Then, the second liquid shown in Table 6 was spray-oiled so that the wet pickup was 30% by weight, and the sample cottons shown in Tables 5 and 6 were obtained. The sample cotton obtained here was evaluated in the same manner as in Test Category 2. The results are shown in Tables 5 and 6.

[0060]

[Table 5]

[0061]

[Table 6]

Examples 17 and 18 and Comparative Examples 16 and 17 Using the sample cottons obtained in Examples 2 and 9, Comparative Example 1 and Comparative Example 10, the method for adjusting the handsheet according to JIS-P8209 is used. Therefore, a sample paper was prepared. With respect to the sample paper obtained here, the tensile strength according to JIS-P8113 and the formation by visual observation were measured. The results are shown in Table 7.

[0063]

[Table 7]

[0064]

As is apparent from the above, the present invention described above has an effect of imparting a high degree of initial water dispersibility and its excellent durability to a hydrophobic synthetic fiber.

─────────────────────────────────────────────────── ─── Continuation of front page (51) Int.Cl. ⁵ Identification number Office reference number FI technical display location // C08L 51/08 LLS 7142-4J D06M 101: 16 D06M 15/59

Claims (1)

[Claims] 1. A grafted polyether ester and / or grafted polyether ester amide of the following A and a nitrogen-containing compound of the following B are A / B = 95/5 to
It is characterized in that the hydrophobic synthetic fiber is treated at a ratio of 50/50 (weight ratio) so that the total adhesion amount of these is 0.1 to 3% by weight with respect to the hydrophobic synthetic fiber. A method for imparting hydrophilicity to the surface of a hydrophobic synthetic fiber. A: one or more selected from grafted polyether esters of A-1 below and grafted polyether ester amides of A-2 below A-1; 8 aromatic or saturated aliphatic dicarboxylic acid
A vinyl monomer was graft-polymerized to a polyether ester obtained from a dicarboxylic acid containing 5 mol% or more or an ester-forming derivative thereof, a glycol, and a polyether compound selected from polyether monool and polyether diol. Grafted polyetheresters A-2; aromatic or saturated aliphatic dicarboxylic acid 9
A polycarboxylic acid obtained by containing 0 mol% or more of a dicarboxylic acid or an ester-forming derivative thereof, an amide-forming compound selected from diamines, lactams and aminocarboxylic acids, and a polyether compound selected from polyether monools and polyether diols Grafted polyether ester amides obtained by graft-polymerizing vinyl monomers onto ether ester amides B: Nitrogen-containing compound having at least one ammonium group and at least two hydrocarbon groups having 12 or more carbon atoms in the molecule One or more selected from compounds