JPS5827741A - Water-based flame-retardant polyester resin - Google Patents

Abstract

PURPOSE:The titled resin that is composed of a polyester resin containing metallic sulfonate containing aromatic dicarboxylic acid and a phosphorus-containing compound as copolymerization components, a water-soluble organic compound and water, thus having fine-size particles which can form coatings with high flame retardancy, water and weathering resistance. CONSTITUTION:The objective resin is composed of (A) a polyester resin in which the polycarboxylic component contains 0.5-10mol% of an aromatic dicarboxylic acid bearing sulfonate metal salt groups and a phosphorus compound is copolymerized by 500-40,000ppm as the amount of phosphorus element based on the resultant polymer, (B) a water-soluble organic compound boiling at 70-200 deg.C such as aliphatic or alicyclic alcohol, ester or ketone and (C) water wherein the weight ratio of A/B/C is (5-70)/(2-50)/(2-93) and B/(B+C) is 0.02-0.66. An example of the phosphorus compound is the one of the formula (R1 is ester- forming group; R2; R3 are halogen, 1-10C hydrocarbon, R1; A is organic residual group; 1 is 1, 2; m, n are 0-4).

Description

[Detailed description of the invention] The present invention relates to aqueous polyester 81 fat.

More specifically, the present invention relates to a water-based polyester resin having a minute particle size that can form a film with excellent flame retardancy, water resistance, and weather resistance.

Organic solvents have traditionally been used in large quantities in the fields of paints, inks, coating agents, adhesives, and various treatment agents for textile products and paper, but in recent years organic solvents have been used from the perspective of saving petroleum resources and preventing environmental pollution. The use of □ is becoming very difficult. Therefore, various methods are available, such as 1) high solid type.

2) Non-aqueous dice version type, 3) Water-based dice version type, 4) Emulsion tights, 5) Solvent-free type, etc. are 1! ! Many of these have already been implemented. Among these, the water-based dice version type is the most versatile because of its ease of handling.

It is seen as promising.

On the other hand, many of the resins currently used are hydrophobic;
A major issue is how to disperse or make it aqueous in water. Another important issue is how to impart water resistance and weather resistance to a film formed from a resin that has been given an affinity for water. These technical solutions are common to any tree, and polyester 81 fingers are no exception.

As a method for dispersing polyester 81 in water or making it aqueous, there is already a method of copolymerizing hydrophilic raw materials. Alternatively, a method of copolymerizing them together is known. However, in either method, K requires the use of a large amount of the above-mentioned hydrophilic raw materials in order to provide excellent water solubility or dispersibility, and the resulting film has very poor water resistance and weather resistance. Become something.

For example, in Japanese Patent Publication No. 47-40873, K is a sulfonic acid metal base-containing compound of 8 mol or more based on the total acid component and a polyethylene glycol of 20 mol or more based on the total glycol component in order to sufficiently release ff4 into water. It is stated that it is necessary to use It can be easily imagined that polyester 1111 has poor water resistance and weather resistance.

That is, the fact that it can be sufficiently dissipated in water means that the film formed after drying has poor water resistance.

In this case, when the film comes into contact with water, not only does the adhesion decrease, but also a change in hue occurs, and therefore paints, inks, etc.
Not resistant to coatings, adhesives, etc. Furthermore, the use of a large amount of polyethylene glycol significantly reduces not only water resistance but also weather resistance.

On the other hand, the use of a large amount of aliphatic dicarboxylic acid
It is well known that the mechanical properties of IQI are reduced.

Unless the conflicting problems of imparting properties such as imparting hydrophilicity, water resistance, and weather resistance are overcome, it will not be of any use.

Furthermore, in recent years there has been a very strong demand for flame retardancy in various applications. For example, in textile products, flame-retardant fibers such as polyvinyl chloride fibers and modacrylic fibers have been developed. Although these flame retardant fibers themselves have excellent flame retardancy.

For example, if the finishing agent or adhesive is selected incorrectly, or if the material is combined with other materials, flame retardancy may be lost, resulting in the occurrence of tofu pull. Further, as a method of imparting flame retardance, a method of mixing or copolymerizing a phosphorus compound is generally known. In the case of a mixing method, there are drawbacks such as separation from an aqueous dispersion or solution and a decrease in adhesion. In the case of the copolymerization method, there are no drawbacks such as a decrease in adhesion, but there is still no product with excellent water resistance and weather resistance, and it cannot be used practically. A similar situation exists for molded products such as films.

The present inventors have found that this method is particularly effective for thermoplastic resin molded products.

The present invention was achieved as a result of intensive research to develop a log-shaped flame-retardant polyester resin with excellent water resistance and weather resistance. That is, the present invention contains (A) a sulfonic acid metal group-containing aromatic dicarboxylic acid in an amount of 0.5 to 10 mole based on the total polycarboxylic acid component, and at least one phosphorus-containing compound as the amount of phosphorus based on the produced polymer. 500-40. OOOpp
m copolymerized polyester resin and (B) boiling point 70
Contains a water-soluble organic compound of ~200°C and (C) water, and (A).

(B) and (C) are expressions (1)@? The water-based flame-retardant polyester-8 is characterized by satisfying the blending ratios of 2) and (3).

Formula (1): (A) + (B) + (C) = 100
(Weight ratio) Formula (2): (A)/(B)/(C)=5
~To72~50/20~93 (weight ratio) Formula (a) = 0.02 ≦(B)/CB)+(C)
≦0.66 (weight ratio) The aqueous polyester resin of the present invention is a polyester resin obtained by copolymerizing (A) : x l* : y acid metal base-containing aromatic dicarboxylic acid and a phosphorus-containing compound, and (B) a boiling point of 70°C. By blending a water-soluble organic compound at ~200°C and CC) water in a specific ratio,
A water-based polyester resin is obtained which has the contradictory properties of imparting hydrophilicity and imparting water resistance and weather resistance, and is imparted with flame retardancy. Furthermore, when using the aqueous polyester 81 of the present invention, a stable product with a particle size of 1 μm or less can be obtained.

In the polyester resin of the present invention, 0.5 to 10 hairs of the polycarboxylic acid component is an aromatic dicarboxylic acid containing a sulfonic acid metal group.

Examples of aromatic dicarboxylic acids containing sulfonic acid metal bases include sulfoterephthalic acid, 5-sulfoisophthalic acid, 4-sulfoheptalic acid, 4-sulfonaphthalene-2,7-dicarboxylic acid, and 5(4-sulfophenokiV)isophthalic acid. Examples of metal salts include L RNa.
, Kn Mgt C11, Cub Fe, and the like. Particularly preferred is 5-sodium sulfoisophthalic acid. The sulfonic acid metal group-containing aromatic dicarboxylic acid has a content of 0.0% based on the total polycarboxylic acid components.
It is 5 to 10 molti.

Preferably, the amount is in the range of 1.0 to 7 moles based on the total polycarboxylic acid components. When no sulfonic acid metal group-containing aromatic dicarboxylic acid is used, the fractionability of polyester-1 with respect to water is very poor.

As the amount of the metal base-containing aromatic dicarboxylic acid increases, SO
Although the fractional property of W with respect to water itself is good.

After coating and drying, the resulting film has very poor water resistance.

The phosphorus-containing compound used in the present invention is used when producing polyester by reacting dicarboxylic acid and glycol, and has one or more ester-forming functional groups in one molecule. The above ester-forming functional groups are -OR,
-COOR (in the formula, R hydrogen atom also has 1 carbon atom)
~10 hydroxy groups).

Examples of such phosphorus-containing compounds include compounds represented by the following general formula (I), compounds represented by the general formula (It), etc. (2) General formula (1): (In the formula, bR1 is a monovalent ester The forming functional group RhR itself is the same or different group, each selected from a halogen atom, a hydrocarbon group having 1 to 10 carbon atoms, and R1, and A represents a divalent or trivalent organic residue. (1 represents 1 or 2hm* n represents an integer from 0 to 4.) 11 set (ff): Recommended R agriculture (in the formula, I, mtfot7'htt1 terror')
, R1 to Rstf are hydrocarbon groups having 1 to 1 o carbon atoms, and when l-m-00, two of R1 to R$ have two ester-forming groups, or one of them has two ester-forming groups. It has ester-forming groups. Also j + mw l or 2
When IR, has one ester-forming group. ) Specific examples of the phosphorus compound represented by the general formula (1) include io-C1,2-jethoxycarbonylethyl)-9slO-dihydro-9-oxa-10.
-7 Osphenthrene-10-oxide, 1O-
(2,3-1)carboxypropyl)-9-oxy-10-phosph77
V n-l Q -oxide, 1O-(2゜3,-!
/methoxycarbonylpropyl)-9tlO-dihydro-9-oxa-10-7m7affenanthrene-10
-oxide, 10-methoxycarbonylethyl-991
0-dihydro-9-oxa-10-7osphaerubenance V-10-oxide, 1O-(2-methquinecarbonyl)-9910-dihydro-9-oxa-
Examples include compounds represented by the following formulas:

OCHs -COOH ■ Specific examples of the phosphorus compound represented by the general formula (turtle) include diethyl ethoxycarbonylethylphosphonate, diethyl ethoxycarbonylethylphosphonate, 2-
Diethyl ethoxycarbonylethylphosphonate, Dimethyl 2-methoxycarbonylethylphosphonate, Dibromoethyl 2-ethoxycarbonylethylphosphonate, 2-
Diethyl (2-hydroxyethoxycarbonyl)ethylphosphonate, diethyl 2-(2-hydroxyethoxycarbonyl)ethylphosphonate, diphenyl 2-ethoxycarbonylethylphosphonate, diethyl 3-hydroxycarbonylpropylphosphonate.

4-x) Diethyl oxycarbonylbutylphosphonate, 2
-diethyl hydroxyethylphosphonate.

Examples include dimethyl 4-methoxycarbonylphenylphosphonate.

A compound represented by the following formula can also be used.

Cs Hs OP-CHs CHm OHsHi Particularly preferred compounds are Cm Is -0-P-CHn CHm C0OHCs
Hg or its ester-forming derivative.

As the phosphorus-containing compound, in addition to #i and the above-mentioned compounds, a polyaryl phosphonate containing 191 or more of the compounds represented by the following formula as a diol component can be used.

(In the formula, Y represents an alkylidene group having 1 to 6 carbon atoms, a V chloroalkylidene group, or a sulfonyl group) The amount of the phosphorus-containing compound used is equivalent to 500 to 40 t000 ppm as a phosphorus amount to the polyester 11 to be obtained. This is the amount. If the amount of phosphorus is less than 500 ppm, flame retardancy is insufficient. If it exceeds 40*OOOO ppm, hydrolysis of the resulting aqueous polyester resin will occur, resulting in poor storage stability, which is not preferable.

Other polycarboxylic acids used in the polyester 81 resin of the present invention include aromatic dicarboxylic acids that do not contain sulfonic acid metal bases, 40 to 99 aa% (based on the total polycarboxylic acid components), aliphatic or ring dicarboxylic acids, 49 to 99 aa% (based on the total polycarboxylic acid components), 0
It is preferably molar (based on the total polycarboxylic acid component).

Examples of aromatic dicarboxylic acids that do not contain sulfonic acid metal groups include terephthalic acid, isophthalic acid, orthophthalic acid, and 2,6-naphthalenedicarboxylic acid. These aromatic dicarboxylic acids that do not contain sulfonic acid metal groups contain 40 to 99% of the polycarboxylic acid component.
It is necessary to be morchi. If it is less than 40 moles, the mechanical strength and weather resistance of polyester 11 will be poor.

Undesirable. If the amount exceeds 99 moles, not only will the polyester resin not be dispersed in the system, but the flame retardance will also be extremely poor.

Examples of aliphatic or ring dicarboxylic acids include succinic acid, adipic acid, azelaic acid, separic acid, dodecanedioic acid, dimer acid, tetrahydrophthalic acid, hexahydrophthalic acid, hexabytrosophthalic acid,
Examples include hexahydroterephthalic acid.

The aliphatic or cycloaliphatic dicarboxylic acid accounts for 49 to 0 moles of the polycarboxylic acid component. If it exceeds 49 molt, it is water resistant.

The coating strength decreases and tackiness appears. Furthermore, Vcp-benzoic acid, p-(2-hydroxyethoxybenzoic acid), hydroxypiparic acid, r-butyrolactone, #-caprolactone, etc. can be used as necessary. Also as necessary.

Tri- or higher-functional polycarboxylic acids such as trimellitic acid and pyromellitic acid can be used if the amount is 10 or less based on the total polycarboxylic acid components.

In the polyester resin of the present invention, the polyol component has 2 carbon atoms.
-8 aliphatic glycol/and carbon number 6-12
Consists of alicyclic glycols.

Examples of aliphatic glycols having 2 to 8 carbon atoms include ethylene glycol and 1.2-7" robylene glycol.

1,3-propane Vol, 1,4-butanediol.

Diethylene glycol, neopentyl glycol.

Examples include 1.5-bentanediol and 1.6-hexanediol. Examples of the alicyclic glycol having 6 to 12 carbon atoms include 1,4-cyclohexane dimetatool. The amount of aliphatic glycol having 2 to 8 carbon atoms and/or alicyclic glycol having 6 to 12 carbon atoms is 90 to 100 mole based on the total polyol component. -1 Trimethylolpropane, trimethylolethane if necessary.

The amount of trifunctional or higher functional noboliol such as glycerin and pentaerythritol may be 5 or less based on the total polyol component.

Further, polyalkylene glycol, particularly polyethylene glycol having a molecular weight of 500 or more, may be used if necessary, provided it is 15% by weight or less based on the total polyol component.

moreover! 7! Preferably it is 5-weight or less. If the amount of polyalkylene glycol, especially polyethylene glycol, exceeds 10 molt, the water resistance and weather resistance of the polyester resin will be extremely reduced.

The polyester resin of the present invention can be produced by any known method. Furthermore, the polyester resin obtained in this way can be produced in a molten state or in a solution state with a water-soluble organic compound described below. compounds, isocyanate compounds, etc. Alternatively, it can be partially reacted with these compounds, and the resulting partial reaction product can similarly be used as a raw material for aqueous polyester resin.

The water-soluble organic compound used in the present invention is polyester s
It is used for the purpose of increasing the consciously lower affinity of um for water and assisting in its dispersion and properties in water. That is, a good aqueous dispersion can be obtained only when the polyester resin of the present invention, a small amount of a water-soluble organic compound, and water coexist.

The water-soluble organic compound used in the present invention is an organic compound having a solubility in water of 20f or more at 20°C, and specifically includes aliphatic and alicyclic alcohols, ethers,
Examples include esters and ketone compounds. Specifically, for example, ethanol, n-propertool, I-propertoolumi-n-butanol, i-butanol, 5ec-
Monohydric alcohols such as butanol and tert-butanol, glycols such as ethylene glycol and propylene glycol, methyl cellosolve, and ethyl cellosolve.

Isopropyl cellosolve, n-butyl cellosolve.

Glycol derivatives such as tert-butyl cellosolve, 3-methyl-3-methoxybutanol, n-butyl cellosolve acetate, needles such as dioxane z, esters such as ethyl acetate, ketones such as methyl ethyl ketone, cyclohexanone, V clooctanone, cyclodecanone, isophorone, etc. And so on. In particular: [L-Inoke n-butyl cellosolve, jet-butyl cellosolve, isopropyl cellosolve, ethyl cellosolve, isopropatool, etc.]. These water-soluble organic compounds can be used alone or in combination of two or more Fi types. 'The boiling point of these water-soluble organic compounds must be in the range of 60 to 200°C. If the boiling point does not reach 60° C., it is difficult to maintain a temperature sufficient to combine or dissolve the organic compound in the polyester resin. Furthermore, the boiling point is 200
If the temperature exceeds ℃, the resulting aqueous polyester w will not dry quickly after application. Furthermore, when an amide or sulfonic acid ester compound is used as the water-soluble compound, the drying properties are poor and the storage stability of the aqueous polyester resin is also poor.

In the present invention, the water-based polyester w is prepared by heating (A) the polyester resin and (B) the water-soluble organic compound at 50 to 200°C.
(C) Add water or add a mixture of (A) and (B) to water at 40 to 120 ml.
Produced by stirring at ℃. Alternatively, (A) polyester w fingers are added to a mixed solution of (C) water and (B) a water-soluble organic compound.

It is also produced by a method of stirring and fractionating at 40 to 100°C.

In either method, (A) polyester! ! 1 finger,
The blending ratio of (B) water-soluble organic compound and (C) water is an important element in maintaining the performance of water-based polyester resin, and it is necessary to satisfy the blending ratio of formula 1), 2), and 3). It is.

Formula 1) A+B+C-100 (weight ratio) Formula 2) A
/B/C depth 5-70/2-50/20/93 (weight ratio) Formula 3) 0.02≦B/B+C≦0.66 (weight ratio) of (A) polyester resin contained in aqueous polyester resin If the blending ratio does not reach 5% by weight or exceeds 70% by weight, the viscosity of the aqueous polymer becomes too low or too high, which is not preferable. If the blending ratio of the water-soluble organic compound (B) contained in the aqueous branch is less than 2% by weight, the dispersibility will be poor and a stable aqueous polyester resin with a particle size of 1 μm or less will be obtained.K<<, 50 If it exceeds % by weight, drying properties may deteriorate, which is not preferable. Particularly preferred i!
CB) The blending ratio of the water-soluble organic compound is 30% by weight or less.

The aqueous polyester resin of the present invention can be used as it is, but it can also be used as an amino resin as a crosslinking agent.

One or more compounds selected from the group of epoxy compounds and isocyanate compounds can be used in combination.

Examples of amino resins include formaldehyde adducts such as urea, melamine, and pensoquanamine, even those having a carbon number of 1.
-6 alkylated products with alcohols can be mentioned. Further, if necessary, a more favorable effect can be achieved by using formalin in combination.

Epoxy compounds include diglycidyl ether of bisphenol A and oligomers thereof, diglycidyl ether of hydrogenated bisphenol A and oligomers thereof, orthophthalic acid diglycidyl ester, and isophthalic acid diglycidyl ester.

Terephthalic acid diglycidyl ester, p-oxybenzoic acid glycidyl ester ether, tetophhydrophthalic acid diglycidyl ester, hexahydrophthalic acid diglycidyl ester, succinic acid diglycidyl ester, adipate diglycidyl ester, sebacate diglycidyl ester Ester, ethylene glycol diglycidyl ether, propylene glycol diglycidyl ether, 1
．． 4-butanediol diglycidyl ether, 1,6-
Hexanethiol digly V-dyl ether and polyalkylene glycol diglycidyl ether [,) Limellitic acid trigly V-dyl ester, triglycidyl isocyanurate, 1,4-diglycidyloxybenzene, diglycidyl dimethylhydantoin, diglycidyl ethylene urea, Examples include diglycidyl propylene urea, glycerol polyglycidyl ether, trimethylolethane polyglycidyl ether, )IJ methylolpropane polyglycidyl ether, pentaerythritol polyglycidyl ether, and polyglycidyl ether of glycerol alkylene oxide adducts.

Furthermore, the isocyanate compound is aromatic.

Aliphatic, araliphatic diisocyanates, trivalent or higher valence l
Diisocyanate is a low molecular compound.

Any polymer compound may be used. For example, tetofumethylene diisocyanate, hexamethylene diisocyanate, toluene diisocyanate, diphenylmethane diisocyanate, hydrogenated diphenylmethane diisocyanate, xylylene diisocyanate, hydrogenated xylylene diisocyanate.

Isocyanate compounds such as isophorone diisocyanate and trimer of isophorone diisoV anate, or an excess amount of these isocyanate compounds, and N,! -, t
Low-molecular active hydrogen compounds such as tf ethylene glycol, propylene glycol, trimethylol propane, glycerin, sorbitol, ethylene V amine, monoethanolamine, SF ethanolamine, triethanolamine, or various polyether polyols, polyester polyols, polyamides Examples include terminal isocyanate group-containing compounds obtained by reacting polymer active hydrogen compounds such as the following.

The isocyanate compound may be blocked isoV anate. Isocyanate blocking agents include, for example, 7 enols such as phenol, thiophenol, methylthiophenol, ethylphenol, cresol, xyleneol, resorcinol, nitrophenol, and chlorophenol, acetoxol, methylethylketoxol, and cyclohexanone. Okilims such as oxime, alcohols such as methanol, ethanol, propatool, butanol, ethylene clofrehydrin, 1,
10-substituted alcohols such as 3-dichloro-2-propanol, t-butanol, t-pentanol, t-
Tertiary alcohols such as butanethiol, #-carblocktam, δ-no(rerolactam, r-butyrolactam,
Examples include lactams such as β-probilfuctam, as well as aromatic amines, imides, acetylacetone,
Acetoff [ester, active methylene compounds such as malonic acid ester, mercaptans, imines.

Also included are ureas, diaryl compounds, sodium bisulfite, and the like. Blocked isoV anate can be obtained by addition reaction of the above-mentioned isocyanate compound and an isocyanate blocking agent by a conventionally known appropriate method.

A curing agent or an accelerator can also be used in combination with these crosslinking agents. The method of blending the crosslinking agent includes a method of mixing it with the polyester resin in advance, a method of mixing it during or after the production of the water-based polyester resin, and any method can be selected depending on the type of the crosslinking agent.

The water-based polyester resin of the present invention can be used for textile products, molded products such as films, processing agents for paper, etc., adhesives, inks, paints, etc.
Used for measuring coating agents, etc., and has unprecedented water resistance and weather resistance! 11 exhibits flammability. It is particularly effective for thermofusible fibers and films such as polyester and polyamide. Aqueous polyester II of the invention
Pigments, dyes, various additives, etc. can be added to the fat.

The present invention will be explained in more detail with reference to Examples below.
The present invention is not limited to these examples.

In the examples, parts simply indicate parts by weight.

Evaluation of various properties was carried out according to the following methods.

1) Particle size Measured using a gruffintometer and an optical microscope.

2) Viscosity Measured using a B-type viscosity needle at 25°C.

3) Adhesion Compliant with ASTM-3359.

4) Adhesiveness of the coating surface Judgment was made by finger touch.

5) Water resistance 9 based on JIS5400.

6) Weatherability Adhesion was measured after irradiation for 300 hours using a Sunshine Weatherometer (manufactured by Atlas Corporation) 7) Flame retardancy JIS L1091-1977.6.4.
It was evaluated by method D (coil method) and expressed as the number of times of flame contact.

8) W, size Measured by cantilever method.

9) Washing resistance: 12/l household detergent at 40°C, i.

Wash for 1 minute, rinse with water for 10 minutes, then dehydrate.

Press dry jI # Before washing after 5 times retention rate.

Production example Dimethyl terephthalate 88.3 parts, dimethyl isophthalate 77.6 parts, 5-sodium dimethyl sulfoisophthalate 7.4 parts, ethylene glycol 95.5 parts, neopentyl glycol 3t, sg, zinc acetate 0.1 part , 0.03 part of sodium acetate was placed in a reaction vessel, and a transesterification reaction was carried out until the theoretical amount of methanol flowed out, and then 41.5 parts of a phosphorus-containing compound (1) having a downwardly moving structure was added. These reaction mixtures were subjected to polycondensation reaction under reduced pressure at 265°C to obtain polyester 11@(A-1). The resulting polyester 11111 has a molecular weight of 15,000. The phosphorus content is 16tOOOOpprn.

Furthermore, polyester resins (A-2) to (A-9) were obtained in exactly the same manner except that the raw materials shown in Table 1 were used.

Their characteristic values are as shown in Table 1. Phosphorus-containing compound (1) Phosphorus-containing compound (2) The following margin is Example 1 Polyester [111N (A-1) 300 parts and n-1 Prepared in 2 containers with 140 parts of Chilse Shisorupu.

Stir at 130°C to 150°C for about 3 hours to obtain a uniform and viscous f.
After obtaining the glIl solution, 560 parts of water was gradually added with vigorous stirring, and after about 1 hour, a homogeneous pale bluish-white aqueous solution was obtained.
A diester 8M fat (B-1) was obtained.

The particle size of the obtained aqueous polyester 11 fat was 1 μm or less. This aqueous polyester resin was left at -5°C for 20 days, but no change in appearance was observed, and no change in viscosity was observed, indicating excellent storage stability.

The obtained aqueous polyester resin was placed on a 125μ thick polyethylene terephthalate film using Percoater #2.
Using 0, the solid film thickness is 10μ.

9.1.
i! The adhesion of the coated film is extremely strong! ! ! , good.

Excellent water resistance with no whitening when immersed in water.

Examples 2 to 5 Water-based polyester resins (B-2) to (B-5> were obtained using the same method as in Example 1 using the formulations shown in Table 2.The resulting water-based The performance of polyester resin is shown in Table 3.

Further, a film was formed on a polyethylene terephthalate film having a thickness of 125 μm using the aqueous polyester resins (B-2) to (B-5) in the same manner as in Example 1. The performance of the obtained film is shown in Table 4.

Comparative Examples 1 to 5 Aqueous polyester resins CB-6) to (B-9) were obtained in the same manner as in Example 1 using the compounding ratios shown in Table 2. The performance of the obtained aqueous polyester resin is shown in Table 3.

Furthermore, water-based polyester m fat (B-6), (B-8),
(B-9) was applied onto a polyethylene terephthalate film having a thickness of 125 μm to form a film in the same manner as in the example. The performance of those films is shown in Table 4.

Example 6 Water-based polyester resin (B-1) was diluted with water to a concentration of 10% by weight, and used to pad a lace curtain made of polyethylene terephthalate filaments.
After squeezing at a squeezing rate of 80 degrees, drying and heat treatment (160°C, 2 minutes) produced a lace curtain with a firm texture and good flame retardancy. The obtained Kyuka Erase curtain retains good properties even after washing tests.

Comparative Example 5 A processed lace curtain was obtained in exactly the same manner as in Example 6 except that water-based polyester fil (B-6') was used in place of water-based polyester fil (B-1). Table 5 shows the properties of the processed lace curtain obtained.

Below is the margin ts5 table (■) Po! Eme Delphi 2 Men F evening lace curtain-mSteel SO average value.

Examples 7 to 10 Heim (Toyo A processed lace curtain was obtained in the same manner as in Example 6, except that a lace curtain (made by spinning, flame-retardant modified polyester moth fiber) was used. The properties of the obtained processed lace curtain are as shown in Table 6.

Comparative Examples 6-8 Water-based polyester resin (B-6), CB-8), (B-9) instead of water-based polyester resin QW (B-2)
A processed V-screen curtain was obtained in the same manner as in Example 7 except that the following was used. The properties of each of the nine processed lace curtains obtained are shown in Table 6.

Table 6 (Ill Heim Lace Curtain (manufactured by Toyobo Co., Ltd., flame retardant modified 1 ester fiber) - ASSSO average value.

Patent applicant: Toyobo Co., Ltd.

Claims (1)

[Scope of Claims] (A) Contains an aromatic dicarboxylic acid containing a sulfonic acid metal base at a rate of 0.5 to 10 molar based on the total polycarboxylic acid component,
and (B) a polyester resin in which at least one phosphorus-containing compound is copolymerized with the produced polymer in an amount of 5oo to 40 ppm of phosphorus and a boiling point of 70 to 200°C.
contains a water-soluble organic compound and (C) water, and (A
), (B) death and (C) are formulas (1), (2) and (3
) water-based flame-retardant polyester IIQ! . Formula (1): (A)+ (B)+ (C)-100(
Weight ratio) formula (2)! (A)/(B)/(C) -5
~To72~50/20~93 (weight ratio) Formula (3)! 0.02≦(B)/(B)+(C)≦0.
66 (weight ratio)