CN101768254B - Novel polyester copolymer containing chain structure of 1,2-propanediol and preparation method thereof - Google Patents
Novel polyester copolymer containing chain structure of 1,2-propanediol and preparation method thereof Download PDFInfo
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- CN101768254B CN101768254B CN 200810208106 CN200810208106A CN101768254B CN 101768254 B CN101768254 B CN 101768254B CN 200810208106 CN200810208106 CN 200810208106 CN 200810208106 A CN200810208106 A CN 200810208106A CN 101768254 B CN101768254 B CN 101768254B
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- 229920000728 polyester Polymers 0.000 title claims abstract description 23
- 238000002360 preparation method Methods 0.000 title claims abstract description 14
- DNIAPMSPPWPWGF-UHFFFAOYSA-N monopropylene glycol Natural products CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 title abstract description 14
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 title abstract 4
- 235000013772 propylene glycol Nutrition 0.000 title abstract 4
- 238000006068 polycondensation reaction Methods 0.000 claims abstract description 23
- VNGOYPQMJFJDLV-UHFFFAOYSA-N dimethyl benzene-1,3-dicarboxylate Chemical compound COC(=O)C1=CC=CC(C(=O)OC)=C1 VNGOYPQMJFJDLV-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000005809 transesterification reaction Methods 0.000 claims abstract description 11
- 238000006243 chemical reaction Methods 0.000 claims abstract description 5
- 239000003054 catalyst Substances 0.000 claims description 26
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 17
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 claims description 15
- 230000032050 esterification Effects 0.000 claims description 14
- 238000005886 esterification reaction Methods 0.000 claims description 14
- UXFQFBNBSPQBJW-UHFFFAOYSA-N 2-amino-2-methylpropane-1,3-diol Chemical compound OCC(N)(C)CO UXFQFBNBSPQBJW-UHFFFAOYSA-N 0.000 claims description 10
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 230000003647 oxidation Effects 0.000 claims description 6
- 238000007254 oxidation reaction Methods 0.000 claims description 6
- 230000006837 decompression Effects 0.000 claims description 5
- YBMRDBCBODYGJE-UHFFFAOYSA-N germanium dioxide Chemical group O=[Ge]=O YBMRDBCBODYGJE-UHFFFAOYSA-N 0.000 claims description 4
- 238000000034 method Methods 0.000 claims description 4
- 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 3
- JVLRYPRBKSMEBF-UHFFFAOYSA-K diacetyloxystibanyl acetate Chemical group [Sb+3].CC([O-])=O.CC([O-])=O.CC([O-])=O JVLRYPRBKSMEBF-UHFFFAOYSA-K 0.000 claims description 3
- FNIHDXPFFIOGKL-UHFFFAOYSA-N disodium;dioxido(oxo)germane Chemical compound [Na+].[Na+].[O-][Ge]([O-])=O FNIHDXPFFIOGKL-UHFFFAOYSA-N 0.000 claims description 3
- 239000003112 inhibitor Substances 0.000 claims description 3
- 239000002994 raw material Substances 0.000 claims description 3
- OQBLGYCUQGDOOR-UHFFFAOYSA-L 1,3,2$l^{2}-dioxastannolane-4,5-dione Chemical compound O=C1O[Sn]OC1=O OQBLGYCUQGDOOR-UHFFFAOYSA-L 0.000 claims description 2
- 230000003064 anti-oxidating effect Effects 0.000 claims description 2
- 229940119177 germanium dioxide Drugs 0.000 claims description 2
- 238000005453 pelletization Methods 0.000 claims description 2
- 229910052761 rare earth metal Inorganic materials 0.000 claims description 2
- 150000002910 rare earth metals Chemical class 0.000 claims description 2
- 230000035484 reaction time Effects 0.000 claims description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 abstract description 20
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 abstract description 12
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 abstract description 6
- 239000000463 material Substances 0.000 abstract description 3
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 abstract 2
- YPFDHNVEDLHUCE-UHFFFAOYSA-N 1,3-propanediol Substances OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 abstract 2
- 229920000166 polytrimethylene carbonate Polymers 0.000 abstract 2
- 239000012535 impurity Substances 0.000 abstract 1
- 238000010792 warming Methods 0.000 description 6
- 229920001634 Copolyester Polymers 0.000 description 4
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 description 4
- ZOIORXHNWRGPMV-UHFFFAOYSA-N acetic acid;zinc Chemical compound [Zn].CC(O)=O.CC(O)=O ZOIORXHNWRGPMV-UHFFFAOYSA-N 0.000 description 3
- 229910052787 antimony Inorganic materials 0.000 description 3
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 3
- 229910001873 dinitrogen Inorganic materials 0.000 description 3
- 235000021050 feed intake Nutrition 0.000 description 3
- 239000004246 zinc acetate Substances 0.000 description 3
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 2
- 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 description 2
- VSGNNIFQASZAOI-UHFFFAOYSA-L calcium acetate Chemical compound [Ca+2].CC([O-])=O.CC([O-])=O VSGNNIFQASZAOI-UHFFFAOYSA-L 0.000 description 2
- 239000001639 calcium acetate Substances 0.000 description 2
- 229960005147 calcium acetate Drugs 0.000 description 2
- 235000011092 calcium acetate Nutrition 0.000 description 2
- 230000003197 catalytic effect Effects 0.000 description 2
- QAHREYKOYSIQPH-UHFFFAOYSA-L cobalt(II) acetate Chemical compound [Co+2].CC([O-])=O.CC([O-])=O QAHREYKOYSIQPH-UHFFFAOYSA-L 0.000 description 2
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 1
- ATJFFYVFTNAWJD-UHFFFAOYSA-N Tin Chemical class [Sn] ATJFFYVFTNAWJD-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 150000007520 diprotic acids Chemical class 0.000 description 1
- 229920006351 engineering plastic Polymers 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 150000002290 germanium Chemical class 0.000 description 1
- 229940071125 manganese acetate Drugs 0.000 description 1
- UOGMEBQRZBEZQT-UHFFFAOYSA-L manganese(2+);diacetate Chemical compound [Mn+2].CC([O-])=O.CC([O-])=O UOGMEBQRZBEZQT-UHFFFAOYSA-L 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 238000000746 purification Methods 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 229920003002 synthetic resin Polymers 0.000 description 1
- 239000000057 synthetic resin Substances 0.000 description 1
- 238000012360 testing method Methods 0.000 description 1
- 239000004753 textile Substances 0.000 description 1
- 229920001169 thermoplastic Polymers 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003608 titanium Chemical class 0.000 description 1
Landscapes
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention relates to a novel polyester copolymer containing the chain structure of 1,2-propanediol and a preparation method thereof. The preparation method using 1,2-propanediol and 1,3-propanediol as glycol materials comprises the following steps: conducting the transesterification of 1,2-propanediol, 1,3-propanediol and dimethyl terephthalate or dimethyl isophthalate; and performing pre-polycondensation and polycondensation to obtain the novel polyester copolymer product. The product of the invention with the intrinsic viscosity thereof being 0.756dL/g to 0.893dL/g has the advantages that the reaction process is simple and controllable, and the content of impurities in the obtained product is lower.
Description
Technical field
The present invention relates to macromolecular material, relate in particular to and a kind ofly contain 1, novel polyester copolymer of 2-Ucar 35 chain structure and preparation method thereof.
Background technology
Polyester is as general engineering plastic; Be widely used in producing textile fibres, container and wrapping material can be by aliphatic dihydroxy alcohol like terepthaloyl moietie (EG), 1; Ammediol (1; 3-PDO), 1, the 4-butyleneglycol (1,4-BD) and to (or) phthalic acid and methyl esters thereof make through over-churning or transesterification reaction.Wherein, PTT (PTT) is the successful first synthetic resin of nineteen forty-one U.S.'s shell chemical company (Shell), is with terephthalic acid and 1, and ammediol is through the thermoplastic polyester product of polycondensation preparation.Because of its excellent physics and chemical property more and more receive people's attention, become the synthon field and had one of differential fibre of development prospect.Nineteen forty-six, Whinfield has at first synthesized the PTT resin, but because raw material 1, the purification difficult of ammediol holds at high price, up to the nineties in 20th century, and 1, after the synthetic technology of ammediol obtained breaking through, the development and application of PTT obtained develop rapidly.And in existing polyester system, introduce new glycol, diacid, be one of range of application method for expanding polyester.
Polyester copolymer (or copolyesters) is through more than one divalent alcohol and/or more than one diprotic acid synthetic polyester.Compare with equal polyester, its molecular chain regularity is relatively poor, so crystallization trend is less.Be generally amorphously, have the higher transparency and hardness.1, the 2-Ucar 35 is introduced in the PTT resin owing to have pending methyl group, obtain novelly containing 1, and the copolyesters of 2-Ucar 35 chain structure, because the introducing of unsymmetrical structure, thereby be expected to obtain copolyesters than high transparent and hardness.
Summary of the invention
The object of the present invention is to provide a kind of product purity height, preparation technology simply to contain 1, novel polyester copolymer of 2-Ucar 35 chain structure and preparation method thereof.
The object of the invention can be realized through following technical scheme:
A kind ofly contain 1, the novel polyester copolymer of 2-Ucar 35 chain structure is characterized in that structure is following:
Wherein, Ar can be
In the described polyester copolymer, x, y satisfy x: y=1: 9～9: 1,50≤x+y≤50000.
A kind ofly contain 1, the preparation method of the novel polyester copolymer of 2-Ucar 35 chain structure is characterized in that this method mainly comprises the following steps:
The first step, the transesterify stage
With 1,2-Ucar 35 and 1 is after ammediol mixes; Add DMT. Dimethyl p-benzenedicarboxylate/dimethyl isophthalate and transesterification catalyst, 180～200 ℃ were reacted 4～6 hours under normal pressure, calculated according to the output of methyl alcohol; When esterification yield reaches 95% at least, finish esterification; The feed ratio of raw material is (1, ammediol+1,2-Ucar 35): (DMT. Dimethyl p-benzenedicarboxylate/dimethyl isophthalate)=2.2～2.4: 1, wherein 1, and ammediol and 1, the mol ratio of 2-Ucar 35 is adjustable.
Second step, polycondensation phase
In esterification products, add polycondensation catalyst, once carry out precondensation and polycondensation, the precondensation temperature is 200～230 ℃; React after 30 minutes; Progressively decompression is 0.5mbar until pressure, and polycondensation reaction time is 2～5 hours; Temperature of reaction is 230～270 ℃, and the gained multipolymer adopts extruding pelletization under the nitrogen protection.
Before feeding intake, described esterification drives the air in the system away, with anti-oxidation with high purity nitrogen.
Described transesterification catalyst is the acetate of metal, as: one or more in zinc acetate, Cobaltous diacetate, manganese acetate, calcium acetate, the antimony acetate etc.; Wherein the zinc acetate catalytic effect is best.
The consumption of described transesterification catalyst is 100～300ppm of DMT. Dimethyl p-benzenedicarboxylate in the system/dimethyl isophthalate total amount.
Described polycondensation catalyst comprises antimony-based catalyst such as Antimony Trioxide: 99.5Min, antimony acetate, antimony glycol etc., germanium series catalysts such as germanium dioxide, sodium germanate etc., Titanium series catalyst such as tetrabutyl titanate etc., C-94, tin series catalysts such as stannous oxalate, rare earth catalyst; Wherein the antimony-based catalyst catalytic effect is best.
The consumption of described polycondensation catalyst is 100～300ppm of DMT. Dimethyl p-benzenedicarboxylate in the system/dimethyl isophthalate total amount.
Described polycondensation phase can add ester stabilizer, like antioxidant 1010, and oxidation inhibitor 168 etc., consumption is 0～300ppm of DMT. Dimethyl p-benzenedicarboxylate in the system/dimethyl isophthalate total amount.
Compared with prior art, the resulting copolyesters limiting viscosity of the present invention is 0.756-0.893dL/g, and its advantage is the reaction process simple controllable, and resulting product foreign matter content is less.
The limiting viscosity testing method of the polyester product of gained is following: be dissolved in 50% (weight) phenol and 50% (weight) 1; 1,2, be made into the 0.5g/dL polymers soln in the 2-tetrachloroethane mixed solvent; In 25 ℃ of water-baths, use Ubbelohde viscometer to measure, record inherent viscosity.
Embodiment
Following embodiment further specifies of the present invention, and unrestricted protection scope of the present invention.
Embodiment 1: (1,2-PDO: 1,3-PDO=20: 80)
The first step, the transesterify stage
Press glycol (1,2-PDO+1,3-PDO): DMT. Dimethyl p-benzenedicarboxylate (DMT)=feed intake at 2.2: 1, wherein 1,2-PDO and 1, the mol ratio of 3-PDO is 20: 80.Add transesterification catalyst zinc acetate (100ppm/g DMT).Drive the air in the system away with high purity nitrogen before feeding intake, repeat this action three times, get rid of clean to guarantee the air in the system.System slowly is warming up to 190 ℃, and normal pressure reacted 4 hours down.Output according to methyl alcohol is calculated, and when esterification yield reaches 95% at least, finishes esterification;
Second step, polycondensation phase
Add polycondensation catalyst Antimony Trioxide: 99.5Min Sb
2O
3(100ppm/gDMT), system is warming up to 220 ℃, reacts after 30 minutes with oxidation inhibitor 168 (200ppm/gDMT), progressively decompression, system pressure is reduced to 0.5mbar, and system temperature rises to 260 ℃, reacts termination in 2.5 hours.The high sticking product of gained is in the protection of nitrogen gas bottom discharge, to avoid possible oxidation.
Embodiment 2: (1,2-PDO: 1,3-PDO=10: 90)
The first step, the transesterify stage
Press glycol (1,2-PDO+1,3-PDO): DMT. Dimethyl p-benzenedicarboxylate (DMT)=feed intake at 2.4: 1, wherein 1,2-PDO and 1, the mol ratio of 3-PDO is 10: 90.Add transesterification catalyst Cobaltous diacetate (300ppm/g DMT).Drive the air in the system away with high purity nitrogen before feeding intake, repeat this action three times, get rid of clean to guarantee the air in the system.System slowly is warming up to 200 ℃, and normal pressure reacted 6 hours down.Output according to methyl alcohol is calculated, and when esterification yield reaches 95% at least, finishes esterification;
Second step, polycondensation phase
Add polycondensation catalyst sodium germanate (300ppm/gDMT) and antioxidant 1010 (300ppm/gDMT), system is warming up to 230 ℃, react after 30 minutes, progressively decompression, system pressure is reduced to 0.5mbar, and system temperature rises to 270 ℃, reacts termination in 5 hours.The high sticking product of gained is in the protection of nitrogen gas bottom discharge, to avoid possible oxidation.
Embodiment 3: (1,2-PDO: 1,3-PDO=90: 10)
The first step, the transesterify stage
Press glycol (1,2-PDO+1,3-PDO): dimethyl isophthalate=feed intake at 2.3: 1, wherein 1,2-PDO and 1, the mol ratio of 3-PDO is 90: 10.Add transesterification catalyst calcium acetate (200ppm/g dimethyl isophthalate).Drive the air in the system away with high purity nitrogen before feeding intake, repeat this action three times, get rid of clean to guarantee the air in the system.System slowly is warming up to 180 ℃, and normal pressure reacted 5 hours down.Output according to methyl alcohol is calculated, and when esterification yield reaches 95% at least, finishes esterification;
Second step, polycondensation phase
Add polycondensation catalyst tetrabutyl titanate (200ppm/g dimethyl isophthalate), system is warming up to 200 ℃, react after 30 minutes, progressively decompression, system pressure is reduced to 0.5mbar, and system temperature rises to 230 ℃, reacts termination in 3.5 hours.The high sticking product of gained is in the protection of nitrogen gas bottom discharge, to avoid possible oxidation.
Embodiment 4～7:
Embodiment 4～7 processes are similar with embodiment 1, and wherein difference is 1,2-PDO and 1, and the consumption of 3-PDO, and the difference of catalyst levels, temperature of reaction, it is 1 said specifically to see attached list.
Subordinate list 1
Claims (6)
1. contain the polyester copolymer of 2-Ucar 35 chain structure, it is characterized in that, structure is following:
Wherein, Ar is
X, y satisfy x: y=1: 9～9: 1,50≤x+y≤50000.
2. claim 1 is described contains 1, and the preparation method of the polyester copolymer of 2-Ucar 35 chain structure is characterized in that this method mainly comprises the following steps:
The first step, the transesterify stage
With 1,2-Ucar 35 and 1 after ammediol mixes, adds dimethyl isophthalate and transesterification catalyst, and 180～200 ℃ were reacted 4～6 hours under normal pressure, calculated according to the output of methyl alcohol, when esterification yield reaches 95% at least, finished esterification; The feed ratio of raw material is (1, ammediol+1,2-Ucar 35): dimethyl isophthalate=2.2～2.4: 1, wherein 1, and ammediol and 1, the molar ratio of 2-Ucar 35 is adjustable;
Second step, polycondensation phase
In esterification products, add polycondensation catalyst, once carry out precondensation and polycondensation, the precondensation temperature is 200～230 ℃; React after 30 minutes; Progressively decompression is 0.5mbar until pressure, and polycondensation reaction time is 2～5 hours; Temperature of reaction is 230～270 ℃, and the gained multipolymer adopts extruding pelletization under the nitrogen protection;
Described transesterification catalyst is an antimony acetate;
Described polycondensation catalyst is selected from germanium dioxide, sodium germanate, C-94, stannous oxalate or rare earth catalyst.
3. according to claim 2ly contain 1, the preparation method of the polyester copolymer of 2-Ucar 35 chain structure is characterized in that, drives the air in the system away with high purity nitrogen before described esterification feeds intake, with anti-oxidation.
4. according to claim 2ly contain 1, the preparation method of the polyester copolymer of 2-Ucar 35 chain structure is characterized in that, the consumption of described transesterification catalyst is 100～300ppm of dimethyl isophthalate total amount in the system.
5. according to claim 2ly contain 1, the preparation method of the polyester copolymer of 2-Ucar 35 chain structure is characterized in that, the consumption of described polycondensation catalyst is 100～300ppm of dimethyl isophthalate total amount in the system.
6. according to claim 2ly contain 1, the preparation method of the polyester copolymer of 2-Ucar 35 chain structure is characterized in that, described polycondensation phase adds antioxidant 1010 or oxidation inhibitor 168, and consumption is 0～300ppm of dimethyl isophthalate total amount in the system.
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| CN 200810208106 CN101768254B (en) | 2008-12-29 | 2008-12-29 | Novel polyester copolymer containing chain structure of 1,2-propanediol and preparation method thereof |
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| CN101768254B true CN101768254B (en) | 2012-12-05 |
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Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1612907A (en) * | 2001-11-12 | 2005-05-04 | 因文塔-费希尔股份有限两合公司 | Method for the continuous production of high-molecular polyester and device for carrying out the method |
| CN1659208A (en) * | 2002-06-12 | 2005-08-24 | 三菱化学株式会社 | Process for producing polyester resin |
| CN101314637A (en) * | 2007-05-31 | 2008-12-03 | 中国科学院化学研究所 | Poly-p-benzene dicarboxylic acid 1,2-propylene glycol ester and copolyester, and preparation thereof |
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2008
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Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1612907A (en) * | 2001-11-12 | 2005-05-04 | 因文塔-费希尔股份有限两合公司 | Method for the continuous production of high-molecular polyester and device for carrying out the method |
| CN1659208A (en) * | 2002-06-12 | 2005-08-24 | 三菱化学株式会社 | Process for producing polyester resin |
| CN101314637A (en) * | 2007-05-31 | 2008-12-03 | 中国科学院化学研究所 | Poly-p-benzene dicarboxylic acid 1,2-propylene glycol ester and copolyester, and preparation thereof |
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