CN103483572B - A kind of preparation method of low-melting-point washable polyester hot-melt adhesive - Google Patents
A kind of preparation method of low-melting-point washable polyester hot-melt adhesive Download PDFInfo
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- 229920000728 polyester Polymers 0.000 title claims abstract description 18
- 239000004831 Hot glue Substances 0.000 title claims abstract description 12
- 238000002360 preparation method Methods 0.000 title claims abstract description 5
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 68
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 40
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 20
- 238000005886 esterification reaction Methods 0.000 claims abstract description 15
- 230000032050 esterification Effects 0.000 claims abstract description 14
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 14
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000002253 acid Substances 0.000 claims abstract description 11
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims abstract description 10
- 230000006837 decompression Effects 0.000 claims abstract description 8
- 239000003112 inhibitor Substances 0.000 claims abstract description 7
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 7
- 230000003647 oxidation Effects 0.000 claims abstract description 7
- 238000007254 oxidation reaction Methods 0.000 claims abstract description 7
- HVLLSGMXQDNUAL-UHFFFAOYSA-N triphenyl phosphite Chemical compound C=1C=CC=CC=1OP(OC=1C=CC=CC=1)OC1=CC=CC=C1 HVLLSGMXQDNUAL-UHFFFAOYSA-N 0.000 claims description 14
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 150000007520 diprotic acids Chemical class 0.000 claims description 10
- 238000002844 melting Methods 0.000 claims description 9
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims description 6
- 239000000203 mixture Substances 0.000 claims description 5
- 238000006243 chemical reaction Methods 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 3
- BGYHLZZASRKEJE-UHFFFAOYSA-N [3-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxy]-2,2-bis[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyloxymethyl]propyl] 3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoate Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)OCC(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)(COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)COC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 BGYHLZZASRKEJE-UHFFFAOYSA-N 0.000 claims description 2
- 230000008018 melting Effects 0.000 claims description 2
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 230000000694 effects Effects 0.000 abstract 1
- 238000005406 washing Methods 0.000 description 11
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 10
- 238000003756 stirring Methods 0.000 description 10
- 238000010792 warming Methods 0.000 description 10
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 8
- 238000012360 testing method Methods 0.000 description 6
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 description 5
- 239000002390 adhesive tape Substances 0.000 description 5
- 230000003247 decreasing effect Effects 0.000 description 5
- 238000007599 discharging Methods 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000007710 freezing Methods 0.000 description 5
- 230000008014 freezing Effects 0.000 description 5
- 238000009413 insulation Methods 0.000 description 5
- 239000000693 micelle Substances 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- 238000010298 pulverizing process Methods 0.000 description 5
- 238000010992 reflux Methods 0.000 description 5
- 229920000139 polyethylene terephthalate Polymers 0.000 description 4
- 239000005020 polyethylene terephthalate Substances 0.000 description 4
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
- 239000004753 textile Substances 0.000 description 4
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical class OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 3
- 238000007086 side reaction Methods 0.000 description 3
- 230000000052 comparative effect Effects 0.000 description 2
- BKIMMITUMNQMOS-UHFFFAOYSA-N nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 239000002994 raw material Substances 0.000 description 2
- 238000010189 synthetic method Methods 0.000 description 2
- 239000002759 woven fabric Substances 0.000 description 2
- 229920001634 Copolyester Polymers 0.000 description 1
- 229920002582 Polyethylene Glycol 600 Polymers 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 230000007812 deficiency Effects 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 238000005265 energy consumption Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 230000007613 environmental effect Effects 0.000 description 1
- 239000003292 glue Substances 0.000 description 1
- 238000003754 machining Methods 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000000178 monomer Substances 0.000 description 1
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 1
- 239000004745 nonwoven fabric Substances 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 229940057847 polyethylene glycol 600 Drugs 0.000 description 1
- -1 polyethylene terephthalate Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- 230000002194 synthesizing effect Effects 0.000 description 1
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- Adhesives Or Adhesive Processes (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a kind of low-melting-point washable polyester hot-melt adhesive and preparation method thereof, comprise the following steps: terephthalic acid, m-phthalic acid, sebacic acid, hexanodioic acid and propylene glycol, dipropylene glycol, glycol ether are carried out esterification by (1) under the effect of catalyzer tetrabutyl titanate; (2) in the product of step (1), add oxidation inhibitor, carry out decompression polycondensation, the low-melting-point washable polyester hot-melt adhesive that fusing point is 90 ~ 105 DEG C can be obtained.
Description
Technical field
The present invention relates to a kind of preparation method of low-melting-point washable polyester hot-melt adhesive.
Background technology
Low-melting point polyester hot melt adhesive, can coordinate with other fibre-forming polymers and manufacture core-skin composite fiber, manufactures chemically woven fabrics, is widely used in chemically woven fabrics industry.At field of textiles, because the material of bonded fiber is different with form, machining state, processing condition etc., require also different to the fusing point of low-melting fiber, the low-melting fiber for non-woven fabrics bonding had, the polyester that fusing point is more than 140 DEG C can meet the demands, and some use low-melting fiber products, the fusing point required is at 110 DEG C, even lower.Along with textile industry development, more and more higher, as high in stripping strength, water-fastness, environmental protection etc. is required for the tackiness agent for textile industry.
The low-melting point polyester great majority sold in the market are all by modification polyethylene terephthalate (PET) gained, if Chinese patent CN1962716A is by m-phthalic acid, nonane diacid and neopentyl glycol modified PET, produce the low-melting point polyester that fusing point is 100 ~ 160 DEG C, though product is stablized, but its esterification reaction temperature is 240 ~ 250 DEG C, polymeric reaction temperature is 275 ~ 285 DEG C, and whole reaction process temperature is high, and energy consumption is larger.The flat 10-298271 of Japanese Patent Application Laid-Open is by 1, the fusing point of 4 butyleneglycols and hexanodioic acid modified PET is the low-melting point polyester of 100 ~ 190 DEG C, but its side reaction is comparatively serious, in raw material 1, the ratio that 4-butyleneglycol generates tetrahydrofuran (THF) by side reaction is high, a ratio of monomer and the ratio of expectation in product are produced depart from, thus affect product performance.Chinese patent CN1618832A esterification divides two stages to carry out, though decrease the probability that BDO generates the side reaction of tetrahydrofuran (THF), esterification is more loaded down with trivial details.Chinese patent CN101338023A synthesizes by BDO, Polyethylene Glycol-600 ~ 6000, m-phthalic acid, terephthalic acid the polyester that fusing point is 110 DEG C ~ 160 DEG C, and its polycondensation phase is more loaded down with trivial details, and its fusing point is still slightly high.The fusing point of the polyester that Chinese patent CN101735437A synthesizes is at 170 DEG C ~ 220 DEG C, but its fusing point is still higher.In order to overcome the deficiencies in the prior art, this patent provides the synthetic method that a kind of fusing point is the laundry-resistant polyester of low melting point of 90 ~ 105 DEG C.
Summary of the invention
The invention provides a kind of water-fastness, synthetic method that fusing point is 90 DEG C ~ 105 DEG C of polyester hot-melt adhesives, comprise the following steps:
(1) diprotic acid and dibasic alcohol and catalyzer tetrabutyl titanate are added by a certain percentage in esterifying kettle and carry out esterification, temperature of reaction is 160 DEG C ~ 205 DEG C, and when the amount that esterification distillates water is 95% ~ 98% of theoretical aquifer yield, esterification terminates;
(2) oxidation inhibitor is added in the product of step (1), 240 ~ 245 DEG C, carry out decompression polycondensation 1.5 hours under the condition of 30 ~ 50Pa, laundry-resistant polyester hot-melt adhesive product can be obtained;
Described diprotic acid is the mixture of terephthalic acid, m-phthalic acid, sebacic acid and hexanodioic acid;
Described dibasic alcohol is the mixture of 1,3-PD, dipropylene glycol and glycol ether;
The ratio of the mole number of described diprotic acid and dibasic alcohol is 1:1.50;
Described terephthalic acid and the mol ratio of m-phthalic acid are 1:0.15 ~ 0.30;
Described terephthalic acid and the mol ratio of sebacic acid are 1:0.30 ~ 0.50;
Described terephthalic acid and the mol ratio of hexanodioic acid are 1:0.20 ~ 0.55;
Described dipropylene glycol and the mol ratio of glycol ether are 1:0.40 ~ 0.82;
Described dipropylene glycol and the mol ratio of 1,3-PD are 1:0.20 ~ 0.47;
Described oxidation inhibitor is selected from the one of triphenyl phosphite, irgasfos 168 and antioxidant 1010;
The quality of described catalyzer tetrabutyl titanate is 0.06 ~ 0.10% of diprotic acid total mass.
The quality of described oxidation inhibitor is 0.20 ~ 0.36% of diprotic acid total mass.
Innovation of the present invention is to be designed by specific composition of raw materials, and synthesizing a kind of fusing point is 90 ~ 105 DEG C, laundry-resistant copolyester hot melt adhesive, and this glue is used for the bonding of textile product, has excellent wash durability and stripping strength.
Performance test
In following examples and comparative example, the performance test standard of each product is respectively: fusing point test is with reference to international standard ISO 11357, and peel strength test is with reference to standard GB/T 11402-1989, and method for washing is with reference to standard GB/T/T8629-2001.
Embodiment
Embodiment 1
By terephthalic acid 166.00g(1.00mol), terephthalic acid 24.90g(0.15mol), hexanodioic acid 73.00g(0.50mol), sebacic acid 70.70g(0.35mol), dipropylene glycol 201.00g(1.50mol), glycol ether 95.40g(0.90mol), 1, ammediol 45.60g(0.60mol), tetrabutyl titanate 0.20g, adds in 1L reactor.This reactor is equipped with stirring, temp measuring system, rectifying column and reflux condensing tube, open after being progressively warming up to 100 DEG C and stir, when temperature is close to 160 DEG C, start have water to distillate, recovered temperature 96 ~ 100 DEG C, continue to be warming up to about 205 DEG C, when aquifer yield reaches more than 95% of theoretical value, esterification terminates.
Add triphenyl phosphite 0.80g again, carry out decompression polycondensation, progressively improve temperature to 240 DEG C, insulation; Pressure in reactor is decreased to 30Pa gradually, and maintains 1.5 hours, can complete polycondensation.Logical nitrogen, remove vacuum, discharging while hot, in cold water, obtains white adhesive tape, then is cut into micelle, obtains product P 1 through freezing and pulverizing.Recording its DSC fusing point is 105 DEG C, carries out making and the test of Re Rong Nian Cun according to above-mentioned standard, and after obtaining 40 DEG C of washings, stripping strength rate of loss is that after 4.2%, 60 DEG C of washings, stripping strength rate of loss is 10.1%.
Embodiment 2
By terephthalic acid 166.00g(1.00mol), terephthalic acid 33.20g(0.20mol), hexanodioic acid 65.70g(0.45mol), sebacic acid 70.70g(0.35mol), dipropylene glycol 241.20g(1.80mol), glycol ether 89.04g(0.84mol), 1, ammediol 27.36g(0.36mol), tetrabutyl titanate 0.27g, adds in 1L reactor.This reactor is equipped with stirring, temp measuring system, rectifying column and reflux condensing tube, open after being progressively warming up to 100 DEG C and stir, when temperature is close to 160 DEG C, start have water to distillate, recovered temperature 96 ~ 100 DEG C, continue to be warming up to about 205 DEG C, when aquifer yield reaches more than 95% of theoretical value, esterification terminates.
Add triphenyl phosphite 0.87g again, carry out decompression polycondensation, progressively improve temperature to 242 DEG C, insulation; Pressure in reactor is decreased to 30Pa gradually, and maintains 1.5 hours, can complete polycondensation.Logical nitrogen, remove vacuum, discharging while hot, in cold water, obtains white adhesive tape, then is cut into micelle, obtains product P 2 through freezing and pulverizing.Recording its DSC fusing point is 100 DEG C.Carry out making and the test of Re Rong Nian Cun according to above-mentioned standard, after obtaining 40 DEG C of washings, stripping strength rate of loss is that after 4.2%, 60 DEG C of washings, stripping strength rate of loss is 9.8%.
Embodiment 3
By terephthalic acid 166.00g(1.00mol), terephthalic acid 41.50g(0.25mol), hexanodioic acid 58.40g(0.40mol), sebacic acid 60.60g(0.30mol), dipropylene glycol 201.00g(1.50mol), glycol ether 87.45g(0.825mol), 1, ammediol 45.60g(0.60mol), tetrabutyl titanate 0.33g, adds in 1L reactor.This reactor is equipped with stirring, temp measuring system, rectifying column and reflux condensing tube, open after being progressively warming up to 100 DEG C and stir, when temperature is close to 160 DEG C, start have water to distillate, recovered temperature 96 ~ 100 DEG C, continue to be warming up to about 205 DEG C, when aquifer yield reaches more than 95% of theoretical value, esterification terminates.
Add triphenyl phosphite 0.98g again, carry out decompression polycondensation, progressively improve temperature to 245 DEG C, insulation; Pressure in reactor is decreased to 30Pa gradually, and maintains 1.5 hours, can complete polycondensation.Logical nitrogen, remove vacuum, discharging while hot, in cold water, obtains white adhesive tape, then is cut into micelle, obtains product P 3 through freezing and pulverizing.Recording its DSC fusing point is 97 DEG C.Carry out making and the test of Re Rong Nian Cun according to above-mentioned standard, after obtaining 40 DEG C of washings, stripping strength rate of loss is that after 4.5%, 60 DEG C of washings, stripping strength rate of loss is 10.3%.
Embodiment 4
By terephthalic acid 166.00g(1.00mol), terephthalic acid 29.88g(0.18mol), hexanodioic acid 29.20g(0.20mol), sebacic acid 84.84g(0.42mol), dipropylene glycol 201.00g(1.50mol), glycol ether 63.60g(0.60mol), 1, ammediol 45.60g(0.60mol), tetrabutyl titanate 0.22g, adds in 1L reactor.This reactor is equipped with stirring, temp measuring system, rectifying column and reflux condensing tube, open after being progressively warming up to 100 DEG C and stir, when temperature is close to 160 DEG C, start have water to distillate, recovered temperature 96 ~ 100 DEG C, continue to be warming up to about 205 DEG C, when aquifer yield reaches more than 95% of theoretical value, esterification terminates.
Add triphenyl phosphite 0.87g again, carry out decompression polycondensation, progressively improve temperature to 240 DEG C, insulation; Pressure in reactor is decreased to 30Pa gradually, and maintains 1.5 hours, can complete polycondensation.Logical nitrogen, remove vacuum, discharging while hot, in cold water, obtains white adhesive tape, then is cut into micelle, obtains product P 4 through freezing and pulverizing.Recording its DSC fusing point is 93 DEG C.Carry out making and the test of Re Rong Nian Cun according to above-mentioned standard, after obtaining 40 DEG C of washings, stripping strength rate of loss is that after 3.9%, 60 DEG C of washings, stripping strength rate of loss is 9.8%.
Comparative example 1
By terephthalic acid 166.00g(1.00mol), terephthalic acid 66.40g(0.40mol), hexanodioic acid 87.60g(0.60mol), sebacic acid 40.40g(0.20mol), dipropylene glycol 201.00g(1.50mol), glycol ether 82.68g(0.78mol), 1, ammediol 77.52g(1.02mol), tetrabutyl titanate 0.29g, adds in 1L reactor.This reactor is equipped with stirring, temp measuring system, rectifying column and reflux condensing tube, open after being progressively warming up to 100 DEG C and stir, when temperature is close to 160 DEG C, start have water to distillate, recovered temperature 96 ~ 100 DEG C, continue to be warming up to about 205 DEG C, when aquifer yield reaches more than 95% of theoretical value, esterification terminates.
Add triphenyl phosphite 0.79g again, carry out decompression polycondensation, progressively improve temperature to 243 DEG C, insulation; Pressure in reactor is decreased to 30Pa gradually, and maintains 1.5 hours, can complete polycondensation.Logical nitrogen, remove vacuum, discharging while hot, in cold water, obtains white adhesive tape, then is cut into micelle, obtains products C 1 through freezing and pulverizing.Recording its DSC fusing point is 150 DEG C.Carry out making and the test of Re Rong Nian Cun according to above-mentioned standard, after obtaining 40 DEG C of washings, stripping strength rate of loss is that after 12.2%, 60 DEG C of washings, stripping strength rate of loss is 26.7%.
Claims (3)
1. a preparation method for low-melting-point washable polyester hot-melt adhesive, is characterized in that, comprises the steps:
(1) diprotic acid and dibasic alcohol and catalyzer tetrabutyl titanate are added in esterifying kettle by a certain percentage carry out esterification, temperature of reaction is 160 DEG C ~ 205 DEG C, when the amount that esterification distillates water is 95% ~ 98% of theoretical aquifer yield, esterification terminates;
(2) oxidation inhibitor is added in the product of step (1), 240 ~ 245 DEG C, carry out decompression polycondensation 1.5 hours under the condition of 30 ~ 50Pa, can obtain laundry-resistant polyester hot-melt adhesive product, and the melting range of this polyester hot-melt adhesive product is 90-105 DEG C; Described diprotic acid is the mixture of terephthalic acid, m-phthalic acid, sebacic acid and hexanodioic acid;
Described dibasic alcohol is the mixture of 1,3-PD, dipropylene glycol and glycol ether;
The ratio of the mole number of described diprotic acid and dibasic alcohol is 1:1.50;
Described terephthalic acid and the mol ratio of m-phthalic acid are 1:0.15 ~ 0.30;
Described terephthalic acid and the mol ratio of sebacic acid are 1:0.30 ~ 0.50;
Described terephthalic acid and the mol ratio of hexanodioic acid are 1:0.20 ~ 0.55;
Described dipropylene glycol and the mol ratio of glycol ether are 1:0.40 ~ 0.82;
Described dipropylene glycol and the mol ratio of 1,3-PD are 1:0.20 ~ 0.47;
Described oxidation inhibitor is selected from the one in triphenyl phosphite, irgasfos 168 and antioxidant 1010.
2. method according to claim 1, is characterized in that, the quality of described catalyzer tetrabutyl titanate is 0.06 ~ 0.10% of diprotic acid total mass.
3. method according to claim 1, is characterized in that, the quality of described oxidation inhibitor is 0.20 ~ 0.36% of diprotic acid total mass.
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| CN201310484473.9A CN103483572B (en) | 2013-10-16 | 2013-10-16 | A kind of preparation method of low-melting-point washable polyester hot-melt adhesive |
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| CN105348497B (en) * | 2015-12-07 | 2018-01-02 | 上海天洋热熔粘接材料股份有限公司 | A kind of novel copolymerized ester PUR and preparation method thereof |
| CN107652420B (en) * | 2017-09-22 | 2019-08-09 | 昆山天洋热熔胶有限公司 | A kind of preparation method of biodegradable copolyester hot melt adhesive |
| CN109517563A (en) * | 2018-11-14 | 2019-03-26 | 金丽丹 | A kind of preparation method of heat-resisting low-melting point polyester hot melt adhesive |
| CN115232293A (en) * | 2022-07-14 | 2022-10-25 | 天津华新盈聚酯材料科技有限公司 | Low-melting-point polyester chip for producing milled hot melt adhesive and preparation method thereof |
| CN115073721A (en) * | 2022-07-22 | 2022-09-20 | 中国石油化工股份有限公司 | Composition for heavy metal-free crystalline low-melting-point polyester, and preparation method and application thereof |
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| CN101338023B (en) * | 2008-08-14 | 2011-05-04 | 浙江理工大学 | Low-melting-point copolyester and method for preparing same |
| CN101735437B (en) * | 2008-11-04 | 2013-03-06 | 中富(广汉)化工实业有限公司 | Copolyester with low melting point and synthesis method thereof |
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