JP3245973B2 - How to dye polyester - Google Patents

Description

DETAILED DESCRIPTION OF THE INVENTION

[0001]

The present invention relates to a method for dyeing polyester. More specifically, the present invention relates to a method for dyeing a polyester such as a fiber or a film, which has excellent dyeing properties and alkali resistance, and retains excellent properties inherent to polyester.

[0002]

2. Description of the Related Art Polyesters, especially polyethylene terephthalate, utilize excellent physical and chemical properties to make fibers,
It is widely used for dyeing films and other applications.

[0003]

However, polyethylene terephthalate does not have good dyeing properties. To dye it with a disperse dye to a sufficient extent, it must be dyed at a high temperature of about 130 ° C. or higher. Equipment is required, and there are problems in productivity, operability, safety, and the like.

Various methods have been proposed for improving the dyeability of polyethylene terephthalate. The most typical method is a method of copolymerizing a polyester with a 5-metal sulfoisophthalic acid component (hereinafter referred to as SIP) to make the polyester dyeable with a basic dye. However, when a large amount of SIP is copolymerized, there is a problem in that alkali resistance is reduced and fibers, films and other uses are restricted, and the cost of SIP is high, which increases costs.

[0005] In addition, a method of using a carrier at the time of dyeing is known, but it has disadvantages such as requiring a special carrier and difficulty in post-treatment of a dyeing solution.

An object of the present invention is to solve the above-mentioned problems of the prior art, and an object of the present invention is to provide a method of dyeing polyester which can be dyed more easily.

[0007]

Means for Solving the Problems As a result of intensive studies, the present inventors have found that a method of dyeing polyester by using a specific 2,2-alkyl-substituted-1,3-propanediol has solved the above-mentioned problems. The inventor has found that the present invention exhibits excellent effects, and has completed the present invention. That is, the gist of the present invention is that terephthalic acid, ethylene glycol and 2,2
-A polyester excellent in dyeability , characterized by copolymerizing an alkyl-substituted-1,3-propanediol-containing material. Further, the molar ratio of 2,2-alkyl-substituted-1,3-propanediol in the diol component is 3 to 40, and B)
The alkyl of the 2,2-alkyl-substituted-1,3-propanediol is selected from the group consisting of ethyl group, propyl group, butyl group and pentyl group; C) the intrinsic viscosity of the polyester is 0.5 to 0.8, D) The polyester excellent in the above-mentioned dyeability, which is characterized by being dyed with a disperse dye.

[0008] The diol component of the polyester of the present invention comprises:
A specific diol component, consisting of ethylene glycol and 2,2-alkyl-substituted-1,3-propanediol. This specific diol is 2,2-
Alkyl-substituted 1,3-propanediol mole % 3 to
Preferably 40, 2,2-alkyl molar ratio of substituted 1,3-propanediol is poor dyeability improving effect is less than 3, also of polyethylene terephthalate inherent strength if the molar% exceeds 40, dimensional stability Many of the excellent properties are degraded and are not preferred. 2,2-alkyl substitution-
As the 1,3-propanediol, those whose alkyl is selected from the group consisting of an ethyl group, a propyl group, a butyl group and a pentyl group are preferable, and specifically, 2,2-diethyl-1,3-propanediol (Hereinafter referred to as DMP), 2-butyl-2-ethyl-1,3-propanediol (hereinafter referred to as DMH), and 2-pentyl-2-propyl-1,3-propanediol (hereinafter referred to as DMN). You can do it. These can be used alone or in any combination depending on the purpose of use.

The polyester of the present invention may be used as other components containing terephthalic acid, ethylene glycol and 2,2-alkyl-substituted-1,3-propanediol as long as its properties are not significantly changed, for example, isophthalic acid. , A polycarboxylic acid such as trimellitic acid, adipic acid, and sebacic acid, and a polyol such as diethylene glycol, triethylene glycol, polyethylene glycol, polypropylene glycol, pentaerythritol, bisphenol A, and hydroquinone.

As the polymerization method of the polyester in the present invention, various ordinary methods can be used. For example, a method of performing a transesterification reaction of a dimethyl ester of a dicarboxylic acid and a diol to distill methanol and then performing a polycondensation method under a reduced pressure and a high vacuum gradually, or an esterification reaction of a dicarboxylic acid and a diol is formed. After distilling water, gradually depressurizing and under high vacuum, performing polycondensation, or when using dimethyl ester of dicarboxylic acid and dicarboxylic acid in combination as raw materials, perform transesterification of dimethyl ester of dicarboxylic acid and diol Further, there is a method of performing an esterification reaction by adding a dicarboxylic acid and then performing polycondensation under a high vacuum. As the transesterification catalyst, manganese acetate, calcium acetate, zinc acetate and the like can be used, and as the polycondensation catalyst, known catalysts such as antimony trioxide, germanium oxide, dibutyltin oxide and titanium tetrabutoxide can be used.

As a stabilizer, a phosphorus compound such as trimethyl phosphate and triphenyl phosphate and a hindered phenol compound such as Irganox 1010 may be used. It may also contain a matting agent and other additives. Various conditions such as a polymerization method, a catalyst, and a stabilizer are not limited to those described above.

The intrinsic viscosity of the polyester in the present invention is preferably 0.5 to 0.8, more preferably 0.55 to 0.8.
75 is preferred. If the intrinsic viscosity is less than 0.5, it is difficult to obtain a fiber film having sufficient strength, while if it exceeds 0.8, the melt viscosity becomes extremely high, and it is difficult to form a spun film.

At present, dyeing into navy or black with a disperse dye having excellent light fastness for interior materials for automobiles is carried out by blending a light color anthraquinone dye as a blue dye which is a main component thereof. However, if an azo-based compound is used, the use of a dye is remarkably increased to obtain a dark hue, and the cost becomes extremely high. According to the dyeing method of the present invention, the amount of dye used in a dark color can be reduced, and the cost merit is extremely large.

[0014]

According to the present invention, characterized by copolymerizing terephthalic acid, ethylene glycol and 2,2-alkyl-substituted-1,3-propanediol containing product po
Polyesters in which the ester is excellent in dyeability and alkali resistance, and which is more beautifully dyed, have original excellent properties and are useful as molded products such as fibers or films.
that's all

[0015]

Next, the present invention will be described in detail with reference to examples. In the examples, characteristic values and the like were measured as follows.

(1) Molar Ratio of Diol Component in Polyester The molar ratio of the diol component was determined by measuring a nuclear magnetic resonance spectrum.

(2) Intrinsic Viscosity Using phenol / tetrachloroethane (6/4) as a solvent, the viscosity was measured at 30 ° C. and calculated by extrapolation.

(3) Strength and elongation CATY-500B, an electronic universal testing machine manufactured by Yonekura Manufacturing Co., Ltd.
Using H, sample length 20 mm, width 5 mm, tensile speed 2
It was measured at 0 mm / min.

(4) Dyeability The film was put into a dye bath of 1,4-diaminoanthraquinone disperse dye (1 g / 300 ml H ₂ O) at 80 ° C., and 24 hours later, a part of the film was collected and o-chloroform was removed. It was dissolved in phenol and the amount of adsorption was colorimetrically determined.

(5) Alkali Resistance The film was cut into 2 × 2 cm and reacted in a 10% aqueous NaOH solution at 80 ° C. for 4 hours to determine the weight loss.

Examples and Comparative Examples Dimethyl terephthalate (DMT) and 2,2-alkyl-substituted-1,3-propanediol in a molar ratio of about 1.3 times those shown in Table 1 were mixed with DMT. As a catalyst, zinc acetate was used in an amount of 7.0 × 10 ⁻⁴ mol / mol of acid component and antimony trioxide was used in an amount of 2.5 × 10 ⁻⁴ mol / mol of acid component, and heated at 200 to 205 ° C. for 1 hour under a nitrogen stream. Next, ethylene glycol (EG) was added so that the total amount of the diol was in a molar ratio of 1: 5 with respect to DMT, and the mixture was further heated for 2 hours. Then, the mixture was heated at 270 to 275 ° C. for 1 hour to distill off excess diol, and further subjected to polycondensation at 280 to 285 ° C. under a reduced pressure of about 0.3 to 0.5 torr to a predetermined intrinsic viscosity.

The obtained polyester was melted, extruded from a T-die, and quenched by a 5 ° C. casting roller to obtain an unstretched film having a thickness of about 100 μm. This unstretched film was heated at 100 ° C. using a tenter-type simultaneous biaxial stretching apparatus.
And stretched at a magnification of 3.0 times the length and 3.0 times the width.
A constant-length heat treatment was performed at 0 ° C. to obtain a stretched film having a width of 400 mm. Table 1 shows the characteristic values of the obtained film. As shown in Table 1, it was confirmed that the specific 2,2-alkyl-substituted-1,3-propanediol significantly improved the dyeability.

[0023]

[Table 1]

Claims (1)

(57) [Claims] 1. A polyester copolymerized with terephthalic acid, ethylene glycol and a 2,2-alkyl-substituted-1,3-propanediol-containing material, wherein A) the 2,2-alkyl-substituted-1,3-propanediol in the diol component. 3-40 mole % of propanediol, B) 2,2-alkyl-substituted-1,
The alkyl of 3-propanediol is selected from the group consisting of ethyl, propyl, butyl and pentyl, C)
Polyester having an intrinsic viscosity of 0.5 to 0.8 and having excellent dyeability, characterized by being dyed with D) a disperse dye.