WO2012027885A1 - 由带侧链的脂肪族二元醇和间苯二元酸二元酯-5-磺酸钠或钾改性的共聚酯及其纤维的制备方法 - Google Patents
由带侧链的脂肪族二元醇和间苯二元酸二元酯-5-磺酸钠或钾改性的共聚酯及其纤维的制备方法 Download PDFInfo
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- WO2012027885A1 WO2012027885A1 PCT/CN2010/076487 CN2010076487W WO2012027885A1 WO 2012027885 A1 WO2012027885 A1 WO 2012027885A1 CN 2010076487 W CN2010076487 W CN 2010076487W WO 2012027885 A1 WO2012027885 A1 WO 2012027885A1
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- copolyester
- esterification
- potassium
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- aliphatic diol
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
- C08G63/68—Polyesters containing atoms other than carbon, hydrogen and oxygen
- C08G63/688—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur
- C08G63/6884—Polyesters containing atoms other than carbon, hydrogen and oxygen containing sulfur derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/6886—Dicarboxylic acids and dihydroxy compounds
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- D—TEXTILES; PAPER
- D01—NATURAL OR MAN-MADE THREADS OR FIBRES; SPINNING
- D01F—CHEMICAL FEATURES IN THE MANUFACTURE OF ARTIFICIAL FILAMENTS, THREADS, FIBRES, BRISTLES OR RIBBONS; APPARATUS SPECIALLY ADAPTED FOR THE MANUFACTURE OF CARBON FILAMENTS
- D01F6/00—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof
- D01F6/78—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products
- D01F6/84—Monocomponent artificial filaments or the like of synthetic polymers; Manufacture thereof from copolycondensation products from copolyesters
Definitions
- the invention relates to the preparation of cationic dye-dyeable copolyester and fiber thereof, in particular to a modification of a fatty acid having a side chain and an isophthalic acid dibasic acid 5-sodium sulfonate or potassium.
- a novel copolyester and a method for preparing the same Background technique
- the application of the modified monomers for copolymerization can be roughly divided into the following three types: (1) Cationic dye-dyeable monomers such as sodium (or potassium benzene sulfonate) (2) Disperse dye-dyeable monomers, such as isophthalic acid having a meta-structure; polyethylene glycol and sebacic acid having a flexible structure; (3) acid dye-dyeable monomers, such as Amino compound.
- Cationic dye-dyeable monomers such as sodium (or potassium benzene sulfonate)
- Disperse dye-dyeable monomers such as isophthalic acid having a meta-structure
- polyethylene glycol and sebacic acid having a flexible structure
- acid dye-dyeable monomers such as Amino compound.
- Cationic dye-dyeable polyester fiber invented by DuPont in 1958, trade name DACRON T, referred to as CDP, industrialized in 1962.
- Toray developed and developed the atmospheric pressure type cationic dye-dyeable polyester fiber, referred to as ECDP.
- High temperature and high pressure cationic dyeable copolyester fiber CDP because dyeing must be carried out under high temperature and pressure conditions, natural fiber properties can be affected when blended with natural fibers such as fiber and cotton wool.
- the atmospheric pressure cationic dye is easy to dye polyester fiber ECDP. Due to the introduction of polyether in the macromolecule, the heat resistance of the fiber is poor, the spinning is unstable, and the spinnability and the properties of the fabric are affected.
- the present invention provides a novel copolyester modified with a side chain aliphatic diol and an isophthalic acid dibasic acid 5-sodium sulfonate or potassium and a fiber thereof.
- a first aspect of the invention relates to a process for preparing a copolyester modified with a side chain aliphatic diol and an isophthalic acid dibasic acid 5-sodium sulfonate sodium or potassium. It is obtained by copolymerization of four kinds of monomers: terephthalic acid, ethylene glycol, isophthalic acid dibasic acid ester 5-sodium sulfonate or potassium, and an aliphatic diol containing a side chain.
- the method includes the following steps:
- Copolymerization of copolyester Ethylene glycol and terephthalic acid are added to the first esterification tank for esterification; then, the reaction material is introduced into the second esterification tank to inject isophthalic acid dibasic acid 5-sodium sulfonate Or potassium, further esterified, wherein the aliphatic diol containing a side chain is injected into the first esterification kettle together with ethylene glycol and terephthalic acid, or an aliphatic diol having a side chain and an isophthalic acid
- the dibasic ester 5-sodium sulfonate or potassium is injected into the second esterification kettle to participate in the esterification reaction; then, the reaction material enters the polycondensation kettle for polycondensation to obtain a copolyester product; in the copolymerization, the reaction raw material is benzoic acid
- a second aspect of the invention relates to a process for preparing a copolyester fiber modified with a side chain aliphatic diol and an isophthalic acid dibasic acid 5-sodium sulfonate sodium or potassium, which method is continuous
- the copolyester is copolymerized from the following four monomers: terephthalic acid, ethylene glycol, isophthalic acid dibasic acid 5-sodium sulfonate Or potassium, and an aliphatic diol containing a side chain.
- the method includes the following steps:
- Copolymerization of copolyester Ethylene glycol and terephthalic acid are added to the first esterification tank for esterification; then, the reaction material is introduced into the second esterification tank to inject isophthalic acid dibasic acid 5-sodium sulfonate Or potassium, further esterified, wherein the aliphatic diol containing a side chain is injected into the first esterification kettle together with ethylene glycol and terephthalic acid, or an aliphatic diol having a side chain and an isophthalic acid
- the dibasic ester 5-sodium sulfonate or potassium is injected into the second esterification kettle to participate in the esterification reaction; then, the reaction material enters the polycondensation kettle for polycondensation to obtain a copolyester product; in the copolymerization, the reaction raw material is benzoic acid
- the copolyester product obtained above is directly spun into a spinning device and spun into a filament or staple fiber of a copolyester.
- the isophthalic acid dibasic ester 5-sodium sulfonate or potassium is selected From: ethylene isophthalate-sodium 5-sulfonate, ethylene isophthalate-potassium 5-sulfonate, propylene glycol isophthalate-sodium 5-sulfonate, propylene glycol isophthalate Ester-5-sulfonic acid potassium, isobutylene isophthalate-sodium 5-sulfonate, pentylene isophthalate-sodium 5-sulfonate, or a combination thereof. More preferred is ethylene isophthalate-sodium 5-sulfonate.
- the side chain-containing aliphatic diol is selected from the group consisting of: 2-methyl-1, 3-propanediol, 2-methyl-1,4-butanediol, 2, 3- Dimethyl-1,4-butanediol, 3-ethyl-1,5-pentanediol, 2-methyl-1,5-pentanediol, 3,3-dimethyl-1, 5- Pentylene glycol, or 3-methyl-3-ethyl-1,5-pentanediol. More preferred is 2-methyl-1,3-propanediol.
- the side chain aliphatic diol is 2-methyl-1,3-propanediol
- the isophthalic acid dibasic acid 5-sodium sulfonate or Potassium is ethylene isophthalate-sodium 5-sulfonate.
- the molar content of the ethylene isophthalate-5-sulfonate unit in the copolyester macromolecular chain is 1.5 mol% to 7 mol%, 2-methyl group relative to the molar content of the terephthalic acid unit.
- the molar content of the -1,3-propanediol unit is from 5 mol% to 20 mol% based on the molar content of the terephthalic acid unit.
- a divalent or trivalent metal compound catalyst is added, selected from one of: a metal Zn, Sb, Mn, Ca or Co compound or Several kinds, the amount of which is 0.01% by weight to 0.08% by weight based on the weight of the terephthalic acid; and the addition of trimethyl phosphate or triphenyl phosphate as a heat stabilizer, the amount of which is 0.02% by weight relative to the weight of the terephthalic acid ⁇ 0.06 weight 0 / 0 .
- the copolymerization and spinning step is preferably carried out sequentially on a large continuous polymerization-spinning apparatus.
- the large-scale continuous polymerization-spinning apparatus preferably includes: a first esterification tank, a second esterification tank, a polycondensation tank, and a spinning device.
- esterification reaction temperature in the first esterification kettle is from 240 ° C to 270 ° C, and the reaction time is from 2 to 4 hours;
- the reaction temperature in the second esterification kettle is 240 ° C - 270 ° C, time 1-3 hours;
- reaction temperature in the polycondensation kettle is 270 ° C -300 ° C, time 2-4 hours;
- the spinning screw temperature is 270 ° C to 320 ° C
- the spinning speed is 400 to 3200 m / min
- the drawing temperature is 70. °C ⁇ 160°C
- the draw ratio is 1 ⁇ 4 times.
- the copolyester product obtained in the polycondensation kettle has an intrinsic viscosity of 0.4 to 0.7 and a melting point of 200 to 240 °C.
- the filaments or staple fibers of the copolyester obtained are under atmospheric pressure boiling conditions, It can be dyed dark with a cationic dye or a disperse dye at 95-100 ° C under normal pressure, and its dye uptake rate is above 90%.
- the copolyester fiber obtained by the method of the present invention can be dyed into a dark color by a cationic dye or a disperse dye under normal pressure boiling conditions, and has a bright color and a wide chromatogram.
- the fiber due to the reduced crystallinity and glass transition temperature of the copolyester, the fiber has an ultra-soft hand, the fabric does not require alkali treatment, and the short fibers also have anti-pilling properties.
- the method of the present invention is easy to implement, and the manufacturing process has no special requirements on the equipment, and can be implemented on the existing large-scale continuous polymerization-spinning equipment in the field, which is very easy to realize industrial production and is low in cost. detailed description
- the present invention relates to a novel copolyester modified with a side chain aliphatic diol and an isophthalic acid dibasic acid 5-sodium sulfonate or potassium and a method for preparing the same.
- the isophthalic acid dibasic acid 5-sodium sulfonate or potassium is preferably selected from the group consisting of: ethylene isophthalate-sodium 5-sulfonate, ethylene isophthalate 5-sulfonic acid Potassium, propylene glycol isophthalate-sodium 5-sulfonate, propylene glycol isophthalate-potassium 5-sulfonate, butylene glycol isophthalate-sodium 5-sulfonate, pentanediol isophthalate Ester-5-sodium sulfonate, or a combination thereof.
- the side chain-containing aliphatic diol preferably contains 4 to 25 carbon atoms, and specific examples thereof include, but are not limited to, 2-methyl-1, 3-propanediol, 2-methyl-1, 4-butylene Glycol, 2, 3-dimethyl-1, 4-butanediol, 3-ethyl-1, 5-pentanediol, 2-methyl-1, 5-pentanediol, 3, 3-di Methyl-1, 5-pentanediol, 3-methyl-3-ethyl-1, 5-pentanediol, and the like.
- the aliphatic diol having a side chain is most preferably 2-methyl-1, 3-propanediol, isophthalic acid dibasic acid 5-sodium sulfonate or potassium is most preferably ethylene isophthalate-5 - sodium sulfonate.
- the molar content of the molar ratio of the terephthalic acid monomer unit is from 1.5 mol% to 7 mol%, and the molar content of the aliphatic diol having a side chain such as 2-methyl-1,3-propanediol monomer unit is relative to The molar content of the terephthalic acid monomer unit is
- the catalyst and the heat stabilizer are added during the copolymerization.
- the specific kind of the catalyst and the heat stabilizer of the present invention is not particularly limited, and those known in the art can be employed.
- a divalent or trivalent metal compound catalyst may be used, preferably one or more of the metal-containing Zn, Sb, Mn, Ca or Co compounds, in an amount of 0.01% to 0.08% by weight of the terephthalic acid (% by weight)
- a heat stabilizer preferably trimethyl phosphate Or triphenyl phosphate, the content of which is 0.02% to 0.06% by weight of terephthalic acid.
- the first esterification tank is esterified with ethylene glycol and terephthalic acid, and the reaction temperature is 240 ° C - 270 ° C for 2-4 hours; Then, entering the second esterification kettle, simultaneously injecting the aliphatic diol containing the side chain and the isophthalic acid dibasic ester 5-sodium sulfonate or potassium, and further esterifying, the reaction temperature is 240 ° C - 270 ° C , time 1-3 hours; then, into the polycondensation kettle, the reaction temperature is 270 ° C -300 ° C, time 2-4 hours, that is, a new copolyester melt; wherein the reaction raw materials terephthalic acid, ethylene glycol, The molar ratio of the aliphatic diol having a side chain and the isophthalic acid dibasic acid 5-sodium sulfonate or potassium is
- An aliphatic diol having a side chain therein may also be added in the first esterification kettle. However, it is preferably added together with sodium or potassium isophthalic acid dibasic acid 5-sulfonate in the second esterification tank.
- a modified copolyester is prepared by using an isophthalic acid comonomer
- an isophthalic acid monomer is added in an esterification tank stage
- the reactivity of the isophthalic acid monomer is less than that of the p-benzoic acid monomer, Will cause agglomeration of isophthalic acid monomer, gp:
- the m-benzoic acid monomer units aggregate together, resulting in non-uniform composition on the macromolecular chain, making the polyester impossible Smooth spinning is carried out in the subsequent spinning stage, and qualified fibers cannot be obtained.
- the isophthalic acid monomer has poor solubility in the glycol, it is not preferable to add it to the esterification tank together with the glycol. Therefore, it is common practice to first esterify an isophthalic acid monomer to an isophthalate ester, then add it to a polycondensation kettle, and copolycondensate with a p-benzoic acid ester such as ethylene terephthalate to form a copolyester. .
- the inventors of the present invention have unexpectedly discovered through research that: in the method of the present invention, isophthalic acid dibasic acid 5-sodium sulfonate or potassium (preferably with a side chain-containing fat) is added to the second esterification kettle.
- the copolyester is added to the second esterification kettle together, and the prepared copolyester has excellent spinnability.
- the obtained modified copolyester can be smoothly spun to form an acceptable fiber having excellent properties.
- the modified copolyester obtained by the process of the present invention can not only be smoothly spun into an acceptable fiber, but also unexpectedly capable of forming fibers (including filaments or short fibers) in a continuous polymerization and direct spinning manner. This ensures that the process of the invention can be carried out on large continuous polymerization-spinning equipment and thus industrially produced.
- the process of the present invention comprises adding a meta-benzene dibasic acid ester to a sodium or potassium 5-sulfonate in a second esterification tank (preferably simultaneously adding a side chain)
- a meta-benzene dibasic acid ester to a sodium or potassium 5-sulfonate in a second esterification tank (preferably simultaneously adding a side chain)
- the aliphatic diol was unexpectedly found to be suitable for continuous polymerization and direct spinning to obtain fibers having excellent properties.
- the isophthalic acid dibasic ester is 5 - the sodium or potassium sulfonate is dissolved in the diol, the unreacted ethylene glycol in the second esterification tank, and preferably the side chain-containing aliphatic diol added simultaneously, which facilitates the dissolution of the meta-benzene dibasic acid binary
- the ester 5-sulfonate sodium or potassium monomer promotes uniform dispersion in the reaction vessel and participates uniformly in the reaction, which helps to improve the composition uniformity of the copolyester product.
- the side chain aliphatic diol and the isophthalic acid dibasic ester 5-sodium sulfonate or potassium modified copolyester melt synthesized on a large continuous polymerization apparatus can be directly spun short fibers or long Silk, in the spinning step, the screw temperature in the spinning device is 270 to 320 ° C, the spinning speed is 400 to 3200 m/min, the drawing temperature is 70 to 160 ° C, and the draw ratio is 1 to 4 times. Modified new copolyester staple fibers or POY, FDY filaments can be obtained, and the elastic yarn DTY can be obtained by adding elastic.
- the copolyester provided by the invention introduces a sulfonate group into its macromolecular chain and introduces a side chain alkane group, so that the copolyester staple fiber can be used for cationic dye under normal pressure boiling conditions.
- the disperse dye can be dyed dark, bright color, extensive chromatogram, anti-pilling, and at the same time, due to the volume effect of the side chain groups of the aliphatic diol with side chains, the crystallization properties of the copolyester are reduced. And the glass transition temperature makes the obtained fiber have a super soft hand and no itching.
- the aliphatic diol with side chain and the isophthalic acid dibasic ester 5-sodium sulfonate or potassium modified copolyester fiber prepared by the invention have no special requirements for the manufacturing process. It is produced on imported or domestically produced ordinary equipment, and the cost is low, which makes it easy to realize industrial production.
- the first esterification tank is fed with 1 ton of terephthalic acid (PTA) and 600 kg of ethylene glycol (EG) for esterification, and a catalyst equivalent to 0.02% by weight of PTA is added.
- PTA terephthalic acid
- EG ethylene glycol
- the first esterification tank was charged with 1 ton of PTA and 410 kg of EG for esterification, and a catalyst equivalent to 0.032% by weight of PTA and a triphenyl phosphate of 0.0125% by weight of PTA were added.
- the reaction temperature was After 260 ° C, after 3 hours of reaction, the material was introduced into the second esterification kettle while injecting a molar equivalent of 17 mol% of 3-methyl-3-ethyl-1,5-pentanediol and equivalent to PTA 1.8 mol%.
- the copolyester has an intrinsic viscosity of 0.512 and a melting point of 216 °C.
- the first esterification tank was charged with 1 ton of PTA and 800 kg of EG for esterification, and a catalyst equivalent to 0.02% by weight of PTA and a triphenyl phosphate equivalent to 0.02% by weight of PTA were added. After the temperature was 260 ° C, after 3 hours of reaction, the material was introduced into the second esterification kettle while injecting 12 mol% of 3-ethyl-1,5-pentanediol equivalent to PTA and 3 mol% of PTA equivalent of PTA.
- Ethylene glycolate-5-sulfonate (with EG as solvent), further esterification, reaction temperature 250 ° C, after 3 hours of reaction, the material enters the polycondensation kettle, the reaction temperature is 270-280 ° C, and the reaction ends after 4 hours.
- a copolyester is obtained.
- the copolyester has an intrinsic viscosity of 0.498 and a melting point of 212 °C.
- Example 4 Continuous polymerization, mixed PTA and EG (molar ratio 1.18), added to the first esterification kettle, while adding a catalyst equivalent to 0.02% by weight of PTA, antimony trioxide and triphenyl phosphate equivalent to 0.02% by weight of PTA
- the reaction temperature was 263 ° C, and the esterification reaction time was 3.5 hours.
- the dyed fiber was dyed with a cationic red X-5 GL dye at 98 ° C under normal pressure at a rate of 93.7%. Further, the disperse dye was used to disperse red 3B, and the dye uptake rate at a normal pressure of 98 ° C was 90.7 %.
- Direct spinning of short fibers by melt spinning speed 1300 m/min, pre-stretching 1.016 times, first draw ratio 2.95 times, second draw ratio 1.125 times, drawing speed 190 m/min, drawing bath temperature 60 ° C, the second drawing temperature is 80 ° C, the relaxation temperature of each zone is 80 ° C / 80 ° C / 75 ° C / 75 ° C, the obtained fiber has a fineness of 2.03 dt, a cut length of 51 mm, and a breaking strength of 2.79 CN/dt.
- the elongation at break is 42.5 %
- the dry heat shrinkage at 180 °C is 23.8%
- the defect is 0.6.
- the dyed fiber was dyed with a cationic yellow X-8GL dye at a temperature of 95-100 ° C at a pressure of 95.2%.
- disperse dye red 3B is used, and the dye uptake rate at normal pressure of 98 ° C is 92.2 %.
- Direct spinning of short fibers by melt spinning speed 870 m/min, pre-stretching 1.02 times, first stretching ratio 3 times, second stretching ratio 1.14 times, stretching speed 190 m/min, drawing bath temperature 65 ° C, the second draw 80 ° C, the relaxation temperature of each zone 65 ° C / 65 ° C / 60 ° C / 60 ° C, the fiber has a fineness of 3.01dt, a cut length of 38mm, a breaking strength of 3.28CN / dt, The elongation at break is 32.5 %, the dry heat shrinkage at 180 °C is 24%, and the defect is 4.5.
- the dyed fiber was dyed with a cationic pink X-FG dye at a normal pressure of 95 to 100 ° C and a dyeing rate of 96.5%.
- the disperse dye was used to disperse red 3B, and it was dyed under normal pressure at 98 ° C, and the dye uptake rate was 93.2 %.
- the fiber was dyed with a cationic violet X-5BLH dye at a pressure of 95-100 ° C at a pressure of 96.2%.
- the disperse dye was used to disperse red 3B, and it was dyed at a normal pressure of 98 ° C, and the dyeing rate was 94. %.
- the second esterification kettle is introduced while injecting 12 mol% of 2-methyl-1,4-butanediol equivalent to PTA and sodium p-isophthalate-5-sulfonate equivalent to 2 mol% of PTA ( With EG as solvent, further esterification, reaction temperature 250 ° C, residence time 2 hours, the reactants enter pre-polycondensation tank I, reaction temperature 270-275 ° C, reaction time is 0.5 hours, and then enter pre-condensation kettle II , the reaction temperature is 270 ⁇ 275 ° C, the reaction time is 1.5 h, finally enters the final polycondensation kettle, the reaction temperature is 280 ⁇ 285 ° C, the reaction time is 2 hours, and the obtained copolyester melt is directly spun into a short cross shape.
- Fiber spinning speed 1150 m / min, pre-stretching 1.05 times, first stretching ratio 2.8 times, second stretching ratio 1.14 times, stretching speed 128m / min, stretching bath temperature 65 ° C, relaxation temperature of each zone 70 ° C / 80 ° C / 8 (TC / 8 (rC / 75 ° C / 70 ° C / 60 ° C, the fiber obtained 2.27 dt, cut length 51mm, breaking strength 2.78CN / dt, elongation at break The rate is 34.2%, the dry heat shrinkage rate at 180 °C is 25.3%, the defect point is 4.5. The fiber hollowness is 18.5%, and the cationic X-GRRL dye is used in 95-1. The dyeing rate was 94.1% at 00 ° C under normal pressure. In addition, red 3B was dispersed by disperse dye, and dyed at normal pressure and 98 ° C, the dye uptake rate was 91.4%.
- the obtained filament fiber is dyed at a constant pressure of 95-100 ° C using a cationic X-GRRL dye. 93.1%.
- the dyeing rate of the dyed red FX dye at 95-100 ° C under normal pressure was 91.3%.
- the dye uptake rate of the dispersed AC-V dye at 95-100 ° C under normal pressure was 95.2. %.
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JP2013513518A JP5751729B2 (ja) | 2010-08-31 | 2010-08-31 | 側鎖を有する脂肪族ジオールとm−ベンゼンジカルボン酸ジエステル−5−スルホン酸ナトリウム又はカリウムとで改質された共重合エステルおよびその繊維の製造方法 |
PCT/CN2010/076487 WO2012027885A1 (zh) | 2010-08-31 | 2010-08-31 | 由带侧链的脂肪族二元醇和间苯二元酸二元酯-5-磺酸钠或钾改性的共聚酯及其纤维的制备方法 |
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Cited By (4)
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WO2018040688A1 (zh) * | 2016-08-31 | 2018-03-08 | 江苏恒力化纤股份有限公司 | 一种改性聚酯及其制备方法 |
CN114164513A (zh) * | 2021-12-27 | 2022-03-11 | 江苏恒科新材料有限公司 | 一种超细阳离子聚酯纤维及其制备方法 |
CN114214755A (zh) * | 2021-12-27 | 2022-03-22 | 江苏恒科新材料有限公司 | 一种常温染色阳离子聚酯纤维及其制备方法 |
CN115785420A (zh) * | 2023-02-09 | 2023-03-14 | 江苏恒力化纤股份有限公司 | 一种酸性可染共聚酯及其制备方法 |
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CN108130609B (zh) * | 2017-12-14 | 2020-02-21 | 江苏恒力化纤股份有限公司 | 一种低收缩型聚酯工业丝及其制备方法 |
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CN101298493A (zh) * | 2007-05-02 | 2008-11-05 | 株式会社晓星 | 可在大气压力下用阳离子染料染色的共聚酯聚合物、其制造方法、及其制得的共聚酯纤维 |
CN101063236A (zh) * | 2007-05-11 | 2007-10-31 | 东华大学 | 一种改性的共聚酯切片或纤维及其制备方法 |
CN101392050A (zh) * | 2007-09-18 | 2009-03-25 | 株式会社晓星 | 阻燃共聚酯聚合物、其制造方法以及阻燃共聚酯纤维 |
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WO2018040688A1 (zh) * | 2016-08-31 | 2018-03-08 | 江苏恒力化纤股份有限公司 | 一种改性聚酯及其制备方法 |
US10465041B2 (en) | 2016-08-31 | 2019-11-05 | Jiangsu Hengli Chemical Fibre Co., Ltd. | Modified polyester and its preparation method |
CN114164513A (zh) * | 2021-12-27 | 2022-03-11 | 江苏恒科新材料有限公司 | 一种超细阳离子聚酯纤维及其制备方法 |
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CN114164513B (zh) * | 2021-12-27 | 2023-12-22 | 江苏恒科新材料有限公司 | 一种超细阳离子聚酯纤维及其制备方法 |
CN115785420A (zh) * | 2023-02-09 | 2023-03-14 | 江苏恒力化纤股份有限公司 | 一种酸性可染共聚酯及其制备方法 |
CN115785420B (zh) * | 2023-02-09 | 2023-06-02 | 江苏恒力化纤股份有限公司 | 一种酸性可染共聚酯及其制备方法 |
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JP2013533905A (ja) | 2013-08-29 |
JP5751729B2 (ja) | 2015-07-22 |
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