Classifications

• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/52—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing synthetic macromolecular substances
  • D06P1/5264—Macromolecular compounds obtained otherwise than by reactions involving only unsaturated carbon-to-carbon bonds
  • D06P1/5271—Polyesters; Polycarbonates; Alkyd resins
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  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
  • D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
  • D06M13/262—Sulfated compounds thiosulfates
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L67/00—Compositions of polyesters obtained by reactions forming a carboxylic ester link in the main chain; Compositions of derivatives of such polymers
  • C08L67/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
  • C08L67/025—Polyesters derived from dicarboxylic acids and dihydroxy compounds containing polyether sequences
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  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/144—Alcohols; Metal alcoholates
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  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
  • D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
  • D06M13/165—Ethers
  • D06M13/17—Polyoxyalkyleneglycol ethers
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  • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
  • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
  • D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/347—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated ethers, acetals, hemiacetals, ketones or aldehydes
• • D—TEXTILES; PAPER
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  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
  • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
  • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/507—Polyesters
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  • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
  • D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
  • D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
  • D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
  • D06M15/53—Polyethers
• • D—TEXTILES; PAPER
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  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
  • D06P1/613—Polyethers without nitrogen
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  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P1/00—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed
  • D06P1/44—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders
  • D06P1/60—General processes of dyeing or printing textiles, or general processes of dyeing leather, furs, or solid macromolecular substances in any form, classified according to the dyes, pigments, or auxiliary substances employed using insoluble pigments or auxiliary substances, e.g. binders using compositions containing polyethers
  • D06P1/613—Polyethers without nitrogen
  • D06P1/6131—Addition products of hydroxyl groups-containing compounds with oxiranes
• • D—TEXTILES; PAPER
  • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
  • D06P—DYEING OR PRINTING TEXTILES; DYEING LEATHER, FURS OR SOLID MACROMOLECULAR SUBSTANCES IN ANY FORM
  • D06P3/00—Special processes of dyeing or printing textiles, or dyeing leather, furs, or solid macromolecular substances in any form, classified according to the material treated
  • D06P3/34—Material containing ester groups
  • D06P3/52—Polyesters
• • C—CHEMISTRY; METALLURGY
  • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
  • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
  • C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
  • C08L71/02—Polyalkylene oxides

Definitions

• the present invention relates to a dyeing quality improver that is suitable for polyester fiber materials and for polyester-based fiber materials composed of composite materials comprising polyester fiber materials and other fiber materials.
• Polyester-based fiber materials are dyed under high-temperature conditions of usually 100-140° C., and this causes the polyester oligomers to elute from the polyester-based fiber material into the fiber surfaces or dyeing bath, adhering not only onto the fiber surfaces but also onto the dyeing machine parts such as the dyeing machine frame and the heat exchanger, thus resulting in problems, including notable lowering of the quality of the obtained fiber product and more difficult control of the operation for raising and lowering of the temperature during the dyeing step.
• polyester-based fiber material that has not been sufficiently scoured before dyeing is introduced into the dyeing bath, and the oil solutions, sizing agents, waxes and the like adhering to the fiber material elute into the dyeing bath, resulting in reduced dispersibility of the dye and formation of its aggregates, and adhesion of the dye aggregates onto the fiber product.
• Polyester-based fiber materials that have not been sufficiently scoured are also associated with problems in terms of the level dyeing property, such that the dyeing results in color irregularities.
• the problem of foreign matter contamination is that treatment of functional agents such as light fastness enhancers or flameproofing agents in the same bath as the dyeing bath produces contamination, due to fiber surface residue of functional agents that have not been taken up into the fiber material.
• Japanese Unexamined Patent Publication No. 2000-154466 discloses a method of preventing the trouble caused by adhesion of oligomers, by adding to the dyeing bath an oligomer removing agent comprising a sulfonic acid salt of polyoxyethylene styrylphenyl ether, and a carboxyl group-containing polymer such as an acrylic acid or methacrylic acid polymer, or a salt thereof.
• Japanese Unexamined Patent Publication No. 2001-159083 discloses a method of minimizing the adverse effects of polyester decomposition products, by adding to the dyeing bath a dyeing aid comprising as an active component one or more agents selected from the group consisting of chelating phosphonate agents, phosphonic acid salt-based chelating agents, polycarboxylic based chelating agents and polycarboxylic acid salt-based chelating agents.
• Japanese Unexamined Patent Publication No. 2001-295136 discloses a method of preventing elution of oligomers by adding to the dyeing bath during the dyeing step an oligomer preventer containing the esterified product of a polyhydric alcohol alkylene oxide addition product and an alkyl or alkenyl fatty acid, or an esterified product obtained by transesterification of a polyhydric alcohol alkylene oxide addition product and a natural animal or vegetable oil thereof comprising an alkyl or alkenyl fatty acid.
• the polyester oligomer removing effect is low even with addition of such oligomer removing agents or preventing agents, and it is not possible at the current time to achieve a satisfactory oligomer removing effect, especially with acidic baths.
• the present inventors have found that by combining a polyester copolymer obtained by polycondensation of a dibasic acid component, containing a fixed amount of a dibasic acid with a sulfonate group, and a dihydric alcohol component, containing a fixed amount of polyethylene glycol, with a styrenated phenolalkylene oxide addition product and/or a higher alcohol alkylene oxide addition product, it is possible to solve the problems of oligomer adhesion during the dyeing step and the problems of dye contamination and foreign matter contamination, and the present invention has been completed based on this finding.
• the invention provides a dyeing quality improver for polyester-based fiber materials characterized by comprising a polyester copolymer, obtained by polycondensation of a dibasic acid component containing a dibasic acid with a sulfonate group in an amount of 15-65 mol % and a dihydric alcohol component containing polyethylene glycol with a molecular weight of 900-3500, having a molecular weight of 3000-30,000 and containing polyoxyethylene chains in the molecule in an amount of 10-40 mass %, and at least one compound selected from among styrenated phenolalkylene oxide addition products and higher alcohol alkylene oxide addition products.
• a polyester copolymer obtained by polycondensation of a dibasic acid component containing a dibasic acid with a sulfonate group in an amount of 15-65 mol % and a dihydric alcohol component containing polyethylene glycol with a molecular weight of 900-3500, having a molecular weight of 3000-
• polyester copolymer in the dyeing quality improver for polyester-based fiber materials according to the invention has excellent affinity for polyester fibers, it can incorporate the residual polyester oligomer on fiber surfaces as well as lubricants, sizing agents and functional drugs such as light fastness enhancers or flameproofing agents, by a synergistic effect, to a greater extent than when using the other component (a styrenated phenolalkylene oxide addition product or higher alcohol alkylene oxide addition product) alone.
• the polyester copolymer has a controlled molecular weight it is detached easily from polyester fibers, and therefore the polyester oligomer, as well as lubricants, sizing agents and functional drugs such as light fastness enhancers and flameproofing agents, can be retained in water.
• polyester copolymer in the dyeing quality improver of the invention contains a sulfonate group, it does not become redeposited on the fiber material or dyeing machine, and therefore the improver can be suitably used in dyeing steps.
• the dyeing quality improver for polyester-based fiber materials according to the invention is characterized by comprising (A) a polyester copolymer, obtained by polycondensation of a dibasic acid component containing a dibasic acid with a sulfonate group in an amount of 15-65 mol % and a dihydric alcohol component containing polyethylene glycol with a molecular weight of 900-3500, and (B) at least one compound selected from among styrenated phenolalkylene oxide addition products and higher alcohol alkylene oxide addition products.
• Preferred sulfonate group-containing dibasic acids for synthesis of polyester-based copolymers used for the invention include metal salts of sulfoterephthalic acid, 5-sulfoisophthalic acid and 4-sulfophthalic acid, and their ester derivatives such as dimethyl ester, diethyl ester and diphenyl esters.
• metal salts there may be mentioned lithium salts, sodium salts, potassium salts and magnesium salts, among which sodium and potassium salts are preferred.
• the content of the sulfonate group-containing dibasic acid in the dibasic acid component is in the range of 15-65 mol %.
• the removing power for polyester oligomers, lubricants, sizing agents and functional agents will be impaired if the sulfonate group-containing dibasic acid is present at less than 15 mol % in the dibasic acid component. This is believed to be because a low sulfonate group content lowers the dispersibility of polyester oligomers, lubricants, sizing agents and functional agents, leading to their redeposition in the fiber material. On the other hand, a content exceeding 65 mol % will impede polycondensation reaction of the polyester copolymer.
• dibasic acids other than sulfonate group-containing dibasic acids to be included in the dibasic acid component used for copolymerization there may be mentioned aromatic carboxylic acids such as terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, diphenoxyethanedicarboxylic acid, ⁇ -hydroxyethoxybenzoic acid and p-hydroxybenzoic acid or aliphatic carboxylic acids such as adipic acid, sebacic acid, maleic acid and succinic acid, and their acid anhydrides or ester derivatives with lower alcohols or glycols may also be used.
• aromatic carboxylic acids such as terephthalic acid, isophthalic acid, naphthalenedicarboxylic acid, diphenyldicarboxylic acid, diphenoxyethanedicarboxylic acid, ⁇ -hydroxyethoxybenzoic acid and p-hydroxybenzoic acid or aliphatic
• the dihydric alcohol component as the other starting material for synthesis of the polyester copolymer contains polyethylene glycol with a molecular weight of 900-3500. A molecular weight of less than 900 for the polyethylene glycol will tend to lower the removing power for polyester oligomers, lubricants, sizing agents and functional agents, while a molecular weight of greater than 3500 will tend to impair the dispersibility of the disperse dye.
• the polyester copolymer also contains 10-40 mass % polyoxyethylene chains derived from the polyethylene glycol.
• a polyoxyethylene chain content of less than 10 mass % will tend to reduce the removing power for polyester oligomers, lubricants, sizing agents, functional agents and the like, while a polyoxyethylene chain content of greater than 40 mass % will lead to increased occurrence of problems such as insufficient disperse dye dispersibility and high foamability during the dyeing process.
• Ethylene glycol is preferred as a dihydric alcohol other than the polyethylene glycol in the dihydric alcohol component used for synthesis of the polyester copolymer, but there may also be used other aliphatic and aromatic diol compounds such as C3 or greater alkylene glycols, neopentyl glycol, bisphenol A, bisphenol S and the like.
• the polyester copolymer used for the dyeing quality improver of the invention has a molecular weight of 3000-30,000. According to the invention, a molecular weight of less than 3000 will tend to lower the removing power for polyester oligomers, lubricants, sizing agents and functional agents, presumably because the affinity of the polyester copolymer for the polyester-based fiber material is lowered. A molecular weight of greater than 30,000 will increase the amount of dyeing quality improver residue on the polyester-based fiber material, thus risking an adverse effect in the subsequent finishing step.
• the dyeing quality improver of the invention comprising a polyester copolymer, that satisfies the aforementioned content of sulfonate group-containing dibasic acids, and the content and molecular weight of polyoxyethylene chains derived from the polyethylene glycol with a molecular weight of 900-3500, has excellent removability for polyester oligomers, lubricants, sizing agents and functional agents from polyester-based fiber materials, and undergoes minimal redepositing onto polyester fiber materials and dyeing machines.
• the process for producing the polyester copolymer of the invention may be any conventional process such as transesterification or direct polymerization, without any particular restrictions.
• the molecular weight refers to the weight-average molecular weight measured by gel permeation chromatography using an HLC-8120 apparatus (product. of Tosoh Corp.), Column: GF310HQ (product of Shodex), and using 50% (v/v) acetonitrile/water as the mobile phase, and using sodium polystyrene sulfonate as the standard substance.
• the dyeing quality improver of the invention contains, in addition to the aforementioned polyester copolymer, one or more compounds selected from the group consisting of styrenated phenolalkylene oxide addition products and higher alcohol alkylene oxide addition products.
• the styrenated phenolalkylene oxide addition product may be a polystyrenated (2-10 mol) phenolalkylene oxide addition product such as a monostyrenated phenolalkylene oxide addition product, distyrenated phenolalkylene oxide addition product or tristyrenated phenolalkylene oxide addition product.
• the number of moles for addition of styrene is preferably 1-5 mol for satisfactory affinity with polyester fibers.
• the higher alcohol in the higher alcohol alkylene oxide addition product is preferably a C8-18 alcohol for more satisfactory affinity with polyester fibers.
• the higher alcohol may be either saturated or unsaturated.
• the form of addition is preferably simple addition of ethylene oxide or random or block addition of ethylene oxide and propylene oxide.
• the proportion of ethylene oxide units among the total alkylene oxide chains is preferably 60-100 mass %. If the proportion of ethylene oxide units is less than 60 mass %, it will tend to be more difficult to remove the lubricant.
• the number of moles for addition of alkylene oxides is preferably 4-30 mol and more preferably 4-20 mol each.
• the alkylene oxide addition products mentioned above may be produced by processes known in the art.
• the mass of the polyester copolymer is preferably 0.5-10 and more preferably 1-10, with respect to the total mass of the styrenated phenolalkylene oxide addition product and higher alcohol alkylene oxide addition product defined as 1, for admixture to obtain the dyeing quality improver.
• Water or a mixture of water and a lower alcohol may be used as the solvent.
• Polyester-based fiber materials to which the dyeing quality improver of the invention may be applied include polyethylene terephthalate, polybutylene terephthalate, polypropylene terephthalate, polytrimethylene terephthalate and polyester fiber materials composed of copolymers comprising the same, as well as composite fiber materials comprising these polyester fiber materials and other synthetic fiber materials, natural fiber materials or regenerated fiber materials, and they may be in the form of yarns, knitted fabrics, woven fabrics, nonwoven fabrics and the like.
• a dyeing quality improver for polyester-based fiber materials according to the invention may be added to the dyeing bath when such polyester-based fiber materials are dyed.
• the amount of dyeing quality improver used may be appropriately adjusted depending on the type of fiber material or dye and on the desired performance.
• the dyeing process may be jet dyeing or a dip dyeing method such as cheese dyeing, beam dyeing, Obermaier dyeing, high-pressure injection dyeing or the like, and any process may be employed without any particular restrictions so long as it allows the object of the invention to be achieved.
• Example 2 The same procedure was carried out as in Example 1, except that 155.2 g (0.8 mol) of dimethyl terephthalate, 59.2 g (0.2 mol) of dimethyl 5-sulfoisophthalate sodium salt, 58 g of ethylene glycol, 131 g of polyethylene glycol with a molecular weight of 2000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 340 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 38 mass %, and the molecular weight was 22,000.
• Example 2 The same procedure was carried out as in Example 1, except that 135.8 g (0.7 mol) of dimethyl terephthalate, 88.8 g (0.3 mol) of dimethyl 5-sulfoisophthalate sodium salt, 54 g of ethylene glycol, 136 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 350 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 38 mass %, and the molecular weight was 5000.
• Example 2 The same procedure was carried out as in Example 1, except that 97 g (0.5 mol) of dimethyl terephthalate, 148 g (0.5 mol) of dimethyl 5-sulfoisophthalate sodium salt, 61 g of ethylene glycol, 38 g of polyethylene glycol with a molecular weight of 2000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 280 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 13 mass %, and the molecular weight was 9000.
• Example 2 The same procedure was carried out as in Example 1, except that 77.6 g (0.4 mol) of dimethyl terephthalate, 177.6 g (0.6 mol) of dimethyl 5-sulfoisophthalate sodium salt, 60, g of ethylene glycol, 39 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 290 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 13 mass %, and the molecular weight was 3000.
• Example 2 The same procedure was carried out as in Example 1, except that 116.4 g (0.6 mol) of dimethyl terephthalate, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 61 g of ethylene glycol, 83 g of polyethylene glycol with a molecular weight of 3000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 315 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 26 mass %, and the molecular weight was 18,000.
• Example 2 The same procedure was carried out as in Example 1, except that 129.6 g (0.6 mol) of 1,8-naphthalenedicarboxylic acid, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 57 g of ethylene glycol, 85 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 343 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 24 mass %, and the molecular weight was 25,000.
• Example 2 The same procedure was carried out as in Example 1, except that 58.8 g (0.6 mol) of maleic anhydride, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 58 g of ethylene glycol, 68 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 267 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 25 mass %, and the molecular weight was 7000.
• Example 2 The same procedure was carried out as in Example 1, except that 116.4 g (0.6 mol) of dimethyl terephthalate, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 83 g of 1,4-butanediol, 83 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 337 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 24 mass %, and the molecular weight was 10,000.
• Example 2 The same procedure was carried out as in Example 1, except that 116.4 g (0.6 mol) of dimethyl terephthalate, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 96 g of neopentyl glycol, 83 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 350 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 23 mass %, and the molecular weight was 28,000.
• Example 2 The same procedure was carried out as in Example 1, except that 116.4 g (0.6 mol) of dimethyl terephthalate, 118.4 g (0.4 mol) of dimethyl 5-sulfoisophthalate sodium salt, 310 g of a 2 molar ethylene oxide adduct of bisphenol S, 83 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 564 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 14 mass %, and the molecular weight was 30,000.
• Example 2 The same procedure was carried out as in Example 1, except that 116.4 g (0.6 mol) of dimethyl terephthalate, 124.8 g (0.4 mol) of dimethyl 5-sulfoisophthalate potassium salt, 57 g of ethylene glycol, 86 g of polyethylene glycol with a molecular weight of 1000 and 0.1 g of zinc acetate were charged into the reactor, to obtain 320 g of a polyester copolymer.
• the polyoxyethylene chain content of the obtained polyester copolymer was approximately 26 mass %, and the molecular weight was 13,000.
• a dyeing quality improver was obtained by mixing 20 g of the polyester copolymer of Synthesis Example 1, 10 g of a 10 molar addition product of tristyrenated phenolethylene oxide and 70 g of water.
• a dyeing quality improver was obtained by mixing 20 g of the polyester copolymer of Synthesis Example 1, 10 g of a 20 molar addition product of tristyrenated phenolethylene oxide and 70 g of water.
• a dyeing quality improver was obtained by mixing 20 g of the polyester copolymer of Synthesis Example 1, 10 g of a 7 molar addition product of lauryl alcohol ethylene oxide and 70 g of water.
• a dyeing quality improver was obtained by the same procedure as in Examples 1 and 2, except that 20 g of the polyester copolymer of Synthesis Example 2 was used instead of 20 g of the polyester copolymer of Synthesis Example 1.
• a dyeing quality improver was obtained by mixing 20 g of the polyester copolymer of Synthesis Example 2, 10 g of an 8 molar addition product of oleyl alcohol ethylene oxide and 70 g of water.
• Dyeing quality improvers were obtained by the same procedure as in Example 1, except that 20 g of the polyester copolymers of Synthesis Examples 3-16 and Comparative Synthesis Examples 1-8 were used instead of 20 g of the polyester copolymer of Synthesis Example 1.
• An aqueous dispersion was prepared comprising 30 mass % of a 10 molar addition product of tristyrenated phenolethylene oxide, for use as a dyeing quality improver.
• An aqueous dispersion was prepared comprising 30 mass % of a 7 molar addition product of lauryl alcohol ethylene oxide, for use as a dyeing quality improver.
• the obtained dyeing quality improvers were evaluated in the following manner.
• polyester satin woven fabrics containing the dyeing quality improvers of Examples 1-20 and Comparative Examples 1, 3, 4 and 6-12 and dyed under the following conditions were subjected to extraction using 1,4-dioxane, and the UV absorbance of the extracts at 286 nm were measured to calculate the oligomer deposition per gram of fabric. The results are shown in Table 2.
• polyester knit greiges dyed under the following conditions using the dyeing quality improvers of Examples 1-20 or Comparative Examples 1, 3, 4 and 6-12 were extracted using diethyl ether.
• the extraction residue was dried at 105° C. and allowed to stand in a desiccator, after which the mass was measured and the oil and fat content (mass %) was calculated with respect to the polyester knit greige. A larger oil and fat content indicates higher scourability.
• a COLOR-PET product of Nissen Corporation
• a dyeing quality improver of Examples 1-20 or Comparative Examples 1, 3, 4 and 6-12 was added, a light fastness enhancer or flameproofing agent was further added as a functional agent, and the knit was dyed under the following conditions, after which the degree of foreign matter contamination remaining on the polyester knit was visually observed and the extent of foreign matter contamination was evaluated as G (no contamination), F (some contamination) or P (notable contamination).
• G no contamination
• F most contamination
• P notable contamination
• polyester satin woven fabrics dyed under the same dyeing conditions as in the oligomer removability test described above were dried at 120° C. ⁇ 1 minute and then heat treated at 180° C. ⁇ 30 seconds. After then cooling to room temperature, a single drop of water was dropped onto the fabric and the time until complete permeation of the water drop from the fabric surface was measured. Lower water absorption was judged as less dyeing quality improver residue. The results are shown in Table 3.
• a high-temperature, high-pressure jet dyeing machine (MINI-JET D-100 by Texam Co., Ltd.) was used, placing a polyester pongee in a treatment bath containing the dyeing quality improver of one of Examples 1-20 or Comparative Examples 1, 3, 4 and 6-12, under the conditions described below, and the condition of bubbles between 60-130° C. with a heating rate of 3° C/min was compared to Comparative Example 11 wherein the dyeing quality improver was water.
• the dyeing quality improvers of the examples of the invention were able to minimize trouble caused by oligomers and problems such as dye contamination and foreign matter contamination without affecting the dyeing quality, and also exhibited good processing suitability evidenced by low foaming during processing.
• Using a dyeing quality improver according to the invention can yield fiber products with satisfactory quality and no processing defects arising from deposition of oligomers, dye contamination or foreign matter contamination, while permitting more economical dyeing of fiber products by reducing the extent of foaming during processing, thus leading to less frequent occurrence of troubles during processing.

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