CN102585182A - Method for preparing amorphous copolyester by post-consumer polyester - Google Patents
Method for preparing amorphous copolyester by post-consumer polyester Download PDFInfo
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- CN102585182A CN102585182A CN2012100058060A CN201210005806A CN102585182A CN 102585182 A CN102585182 A CN 102585182A CN 2012100058060 A CN2012100058060 A CN 2012100058060A CN 201210005806 A CN201210005806 A CN 201210005806A CN 102585182 A CN102585182 A CN 102585182A
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- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
- Y02W—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO WASTEWATER TREATMENT OR WASTE MANAGEMENT
- Y02W30/00—Technologies for solid waste management
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- Y02W30/62—Plastics recycling; Rubber recycling
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Abstract
The invention discloses a method for preparing amorphous copolyester by using post-consumer polyester. The method comprises the following steps of: (1) alcoholysis, reacting post-consumer polyester with dihydric alcohol at the temperature of 120-250 DEG C under the effect of a catalyst so that the polyester is subjected to alcoholysis to form a corresponding lower polymer; (b) esterification, adding cyclization diphenyl carbinol to the low polymer, carrying out esterification reaction at the temperature of 200-270 DEG C, slipping out excess ethylene glycol, and obtaining a corresponding esterification product; (c) polycondensation: controlling the vacuum degree of a reaction system to be gradually reduced till the vacuum degree is less than 100Pa at the temperature of 260-270 DEG C to carry out polycondensation reaction on the esterification product, and obtaining the amorphous copolyester. According to the method, the post-consumer polyethylene terephthalate amorphous copolyester is adopted, thereby the recycling problem of the post-consumer polyester is solved, the secondary pollution is avoided, and the productive technology is simple, environment-friendly and low-carbon. The polyester material produced by the method has excellent mechanical property and attractive appearance.
Description
Technical field
The present invention relates to a kind of preparation method of non-crystalline copolyesters.
Background technology
PETG is a kind of non-crystalline type copolyester, and along with the increase of CHDM in the multipolymer, fusing point descends, and second-order transition temperature rises, and percent crystallinity descends, and forms amorphous polymer at last.The content of CHDM is more suitable at 30%-40% among the general PETG.The transparency of PETG goods is high, and glossiness is high, is a kind of brand-new transparent engineering plastics; In addition shock strength excellence, good heat resistance, heat sealability is good, bending is not whitened, mar-proof, anti-anti-aging, anti-electrostatic, chemical resistant properties excellent, low extractibility, hydrolytic resistance, good fluidity, strong coloring force, be easy to forming process, wholesomeness good (meeting FDA), belongs to environmentally-friendly plastic of new generation.
CN101328257A the present invention discloses a kind of method of manufacture of polybutylene terephthalate; With polyethylene terephthalate and butyleneglycol; Under the temperature condition of 190 ℃～260 ℃ of degree, through the normal pressure depolymerization, the condition that is reducing pressure again; Deviate from low molecular weight diols, obtain polybutylene terephthalate.This technology is after depolymerization, and nearly all terepthaloyl moietie is all replaced by butyleneglycol, and material obtains performance and the close basically material of pure PBT, and energy consumption is higher relatively.
CN 1807486 the invention belongs to the modified copolyester for non-fiber field, and particularly the non-fiber of 1,4 cyclohexane dimethanol modification polyethyleneterephthalate is with the method for vibrin.The present invention is through common big bright PET chips is carried out alcoholysis; Obtain the ethylene glycol terephthalate oligopolymer; With this oligopolymer is mother liquor; Under normal pressure, make PTA and mix divalent alcohol (EG+CHDM) and carry out esterification and polycondensation, prepared intrinsic viscosity at 0.65-0.85dL/g and have the modified copolyester product that use in the engineering plastics field that is applicable to of good transparency.This new operational path not only makes the esterification smooth operation, is easy to control, and side reaction is few, and makes the limiting viscosity and the transparent requirement that all can satisfy the polyester transparent board materials production of the section of the finished product modified copolyester.
Now, the white pollution problems of environment is serious day by day, and wherein most pollution comes from non-degraded polyester (PET) wrapping material that abandon after the consumption.The technology of much recycling about post-consumer polyester is also arranged at present; For example: the CN00815876 patent discloses a kind ofly processes the method for article by reclaiming the PET material, the principal feature of this method be with the PET material that reclaims in pre-treatment, heat, the dry and granulation of crystallization at high temperature simultaneously.No. 00803627 patent of CN discloses a kind of depolymerization and purification process that pollutes the back polyester.No. 00817514 patent of CN discloses a kind of method of from polyester (polyethyleneterephthalate (the PET)) waste material that contains inclusion, separating and reclaim DMT. Dimethyl p-benzenedicarboxylate and terepthaloyl moietie.
CN 97193738 the application relate to three one step process that preparation has the copolyester of neutralc tint, highly transparent and brightness increase.This method comprises makes terephthalic acid, terepthaloyl moietie and 1, and the 4-cyclohexane dimethyl carbinol is 1.7:1-6.0:1 in the reinforced mol ratio of total divalent alcohol and dicarboxylicacid, temperature 240-280 ℃ with pressure 200-650kPa reaction formation esterification products down; Add polycondensation catalyst and toning agent; With make down product carry out polycondensation formation high-molecular weight copolyester at temperature 260-290 ℃ with decompression.
Aforesaid method all is to adopt the synthetic non-crystalline copolyesters of brand-new starting material; The present invention adopts synthetic non-crystalline copolyesters of the polyester after the consumption and prior art to have tangible difference; With existing P ET recovery technology elder generation ratio, the present invention has the advantage that technology is simple, easy to operate, cost is low simultaneously.
Summary of the invention
For overcoming above technological deficiency, the invention provides a kind of method by the polyester manufacture non-crystalline copolyesters that reclaims after the consumption.Polyester material after this method can be directly reclaims consumption be converted into the non-crystalline copolyesters material, for the recycling of non-degraded polyester white pollution thing provides a benign cycle passage.
To achieve these goals, the present invention adopts following technical scheme:
A kind ofly prepare the method for non-crystalline copolyesters, may further comprise the steps by post-consumer polyester:
(a) alcoholysis: in 120-250 ℃ of reaction, making the polyester alcoholysis is corresponding oligopolymer under catalyst action for polyester after the consumption and divalent alcohol;
(b) esterification: in above-mentioned oligopolymer, add the cyclisation dimethanol, under 200-270 ℃, carry out esterification, slip out excessive terepthaloyl moietie, get corresponding esterification products;
(c) polycondensation: with above-mentioned esterification products under 260-270 ℃ temperature, control reaction system vacuum tightness reduces to less than 100Pa gradually, carries out polycondensation, makes non-crystalline copolyesters.
In aforesaid method, the said alcoholysis process of step (a) can be carried out under normal pressure or positive pressure, and temperature is 190-250 ℃, and the time is 120-240 minute.
In aforesaid method, the said esterification process of step (b) carries out under condition of normal pressure, and temperature is 200-270 ℃, and the time is 30-90 minute.
In aforesaid method, the said described polycondensation process of step (c) is following:
Reaction kettle was constantly reduced to pressure below the 100Pa in 80 minutes, slip out excessive terepthaloyl moietie and cyclisation divalent alcohol, the temperature of reaction kettle is controlled at 250-270 ℃; Reaction times 180-240 minute; Reaction adds nitrogen after finishing, and makes to be malleation in the reaction kettle, and polymkeric substance is emitted through end of extruded band; Pelletizing, drying.
In aforesaid method, the polyester after the described consumption is selected from one or more mixtures in polyethylene terephthalate, PTT, polybutylene terephthalate, the polyether ester.
In aforesaid method, polyester beverage bottle, polyester film or trevira that described polyethylene terephthalate reclaims from the consumption back.
In aforesaid method, described divalent alcohol is selected from one or more the mixture in straight chain aliphatic dihydroxy alcohol, the cyclisation aliphatic dihydroxy alcohol.
In aforesaid method, said straight chain aliphatic dihydroxy alcohol is selected from terepthaloyl moietie, 1,2-Ucar 35,1, ammediol, 1; 2-butyleneglycol, 1,4-butyleneglycol, 1,5-pentanediol, 2; 2-dimethyl--1, ammediol, the 2-ethyl-2-tertiary butyl-1, ammediol or 2; 2,4-trimethylammonium-1, the one or more kinds of mixtures in the 6-pinakon; Said cyclisation aliphatic dihydroxy alcohol is selected from pentamethylene glycol, 1,4 cyclohexane dimethanol, 1,2-cyclohexanedimethanol, 1, the one or more kinds of mixtures in 3-cyclohexanedimethanol, 1,4 cyclohexane dimethanol or the Isosorbide.
In aforesaid method, the mol ratio of divalent alcohol and polyester terephthalic acid group is 0.8-2:1 during the said alcoholysis of step (a).
In aforesaid method, the catalyzer of the said alcoholysis step of step (a) is selected from one or more the mixture in the organic metal salt of Ti, Ge, La, Ce, Zn, Fe, Mn, Co, V, Zr, Li, Ca or these elements; The catalyzer that the described polycondensation of step (c) is adopted is an organic titanium.
30% of whole pure content to 70 % are the cyclisation aliphatic dihydroxy alcohol in the above-mentioned non-crystalline copolyesters.
Thermoplastic polyester is the polymkeric substance that is obtained through polycondensation by divalent alcohol and diprotic acid in the prior art.Via different types of diprotic acid and divalent alcohol, can synthesize multiple polyester with different characteristics.Commercial principal item mainly contains: polybutylene terephthalate, polyethylene terephthalate, poly terephthalic acid-1,4-hexanaphthene dimethyl ester, PBN and polyester liquid crystalline polymers series, polyarylester, polyester elastomer etc.Different along with polyester kind and manufacturer, also there are difference in its synthesis and preparation process and compound method.Usually, production of polyester has two kinds of batch production process and continous way production processes.Basic, polyester synthetic chemical process is basically via esterification stage, transesterification reaction stage, polycondensation stage, different according to polyester kind and synthetic control method, and there are characteristics separately again in the equipment configuration and the processing requirement in each stage.
The method of the synthetic non-crystalline copolyesters of the present invention, its preparation method includes the alcoholysis reaction stage, esterification stage and polycondensation stage.
The source of post-consumer polyester that the present invention adopts mainly contains two portions, and a part is waste material, the scrap stock that produce in the process of manufacture; Second section then is the depleted polyester packages, like pet bottle, polyester film etc.First kind of useless polyester is cleaner, can directly utilize again; Second kind of waste material often has pollutent, must remove pollutent earlier and etcetera just can be recycled through separating.
Can come catalyzed reaction through in reaction process, adding appropriate amount of catalysts when preparing non-crystalline copolyesters through polycondensation; This type catalyzer is selected from the mixture of stibnide, titanium sub-group compound and these compounds, perhaps uses the material with same function.Catalyst levels is the 50-1000ppm of weight resin.
In polycondensation process, can add the compound that contains cobalt polymkeric substance is mixed colours, such as Cobaltous diacetate.
In polycondensation process; In order to prevent unnecessary degraded and/or branching reaction; Can in this reaction process, add an amount of stablizer, this type stablizer comprises: phosphoric acid, phosphorous acid, triphenylphosphate, trimethyl phosphite 99, trialkyl phosphite, tricresyl phosphite phenylester, phosphonic acids triphenyl ester, phosphonic acids trialkyl ester.In polycondensation process, also can add the oxidation inhibitor of hindered phenolic, like antioxidant 1010, oxidation inhibitor 168, antioxidant 1076.
Compared with prior art, the present invention has following beneficial effect:
1. the present invention adopts the polyethylene terephthalate non-crystalline copolyesters after the consumption, has both solved the recovery problem of post-consumer polyester, has avoided secondary pollution again, and the simple environmental protection low-carbon (LC) of production technique.
2. the polyester material of the present invention's production has excellent mechanical property and aesthetic appearance.
Embodiment
Provide embodiment below more specifying the present invention, but it is worthy of note that the present invention is not limited to these embodiment, some nonessential change and adjustment that one of skill in the art makes according to the invention described above still belong to protection scope of the present invention.
The testing method of index of correlation is following in the embodiment:
1. characteristic viscosity determining method: 25 ℃ of mensuration, as solvent, adopt the limiting viscosity of determination of ubbelohde viscometer sample with phenol-orthodichlorobenzene mixed solution (mass ratio 3:2), sample concentration is 0.005 g/mL.
2. content of carboxyl end group testing method: (mass ratio 7:3) is solvent with ortho-cresol-trichloromethane mixed solution; Adopt Switzerland's ten thousand logical Titrino series automatic potential titrator tests examination content of carboxyl end group, testing method is referring to standard FZ/T 50012-2006 " polyester middle-end carboxyl Content volumetry ".
3. plastics melt temperature testing method: adopt the melt temperature of Perkin Elmer DSC-6 analyser specimen, nitrogen flow rate is 20 mL/min, 10 ℃/min of temperature rise rate.
Embodiment 1
Join the carafe polyethylene terephthalate 35g after terepthaloyl moietie 18g, the consumption in the reaction kettle; Under the nitrogen protection, be warming up to 210 ℃, add tetrabutyl titanate 30mg; Keeping reactor temperature is 210 ℃, reacts the polyethylene terephthalate alcoholysis that made wherein in 4 hours.Add cyclohexanedimethanol 8g, carry out esterification, the temperature of CONTROL PROCESS top of tower is 196 ℃, and excessive terepthaloyl moietie slips out to make part; Terepthaloyl moietie amount through weighing reaction generates is judged level of response, adds Cobaltous diacetate 30mg, after the temperature to 240 ℃, reacts 30 minutes; Begin slowly to be warming up to 265 ℃ then, progressively increase vacuum tightness, keep temperature-resistant; Keep below the still internal pressure 80Pa, reacted 3.5 hours, promptly get product.
Obtain product index of correlation: viscosity 0.82dL/g, end carboxyl 30mol/t.
Embodiment 2
Join the carafe polyethylene terephthalate 60g after terepthaloyl moietie 25g, the consumption in the reaction kettle; Under the nitrogen protection, be warming up to 210 ℃, add tetrabutyl titanate 50mg; Keeping reactor temperature is 210 ℃; Condensing surface refluxes terepthaloyl moietie, makes polyethylene terephthalate alcoholysis wherein, reacts 3 hours.Add cyclohexanedimethanol 20g, carry out esterification, judge level of response through the water that the weighing reaction generates, esterification yield reaches at 95% o'clock; Add Cobaltous diacetate 50mg,, reacted 30 minutes after the temperature to 230 ℃; Begin slowly to be warming up to 245 ℃ then, progressively increase vacuum tightness, keep temperature-resistant; Keep below the still internal pressure 80Pa, reacted 3.5 hours, promptly get product.
Obtain product index of correlation: viscosity 0.80dL/g, end carboxyl 30mol/t.
Embodiment 3
Join carafe polyethylene terephthalate 60 g after terepthaloyl moietie 33g, cetomacrogol 1000 5g, the consumption in the reaction kettle; Under the nitrogen protection, be warming up to 210 ℃, add tetrabutyl titanate 30mg; Keeping reactor temperature is 210 ℃; Condensing surface refluxes terepthaloyl moietie, makes polyethylene terephthalate alcoholysis wherein, reacts 4 hours.Add 1,4 cyclohexane dimethanol 20g, carry out esterification, judge level of response through the water that the weighing reaction generates; Esterification yield reaches at 95% o'clock, after the temperature to 230 ℃, reacts 30 minutes; Begin slowly to be warming up to 245 ℃ then, progressively increase vacuum tightness, keep temperature-resistant; Keep below the still internal pressure 80Pa, reacted 3.5 hours, promptly get product.
Obtain product index of correlation: viscosity 0.85dL/g, end carboxyl 30mol/t.
Embodiment 4
Join the carafe polyethylene terephthalate 15kg after terepthaloyl moietie 17kg, the consumption in the reaction kettle; Under the nitrogen protection, be warming up to 210 ℃, add tetrabutyl titanate 30g; Keeping reactor temperature is 210 ℃; Make polyethylene terephthalate alcoholysis wherein, remove reaction terepthaloyl moietie through shunting simultaneously, reacted 4 hours.Add 1,4 cyclohexane dimethanol 10kg, carry out esterification, judge level of response through the terepthaloyl moietie that the weighing reaction generates; Esterification yield reaches at 95% o'clock, after the temperature to 240 ℃, reacts 30 minutes; Begin slowly to be warming up to 265 ℃ then, progressively increase vacuum tightness, keep temperature-resistant; Keep below the still internal pressure 80Pa, reacted 3.5 hours, promptly get product.
Obtain product index of correlation: viscosity 0.75dL/g, end carboxyl 25mol/t.
Claims (10)
1. one kind prepares the method for non-crystalline copolyesters by post-consumer polyester, it is characterized in that may further comprise the steps:
(a) alcoholysis: in 120-250 ℃ of reaction, making the polyester alcoholysis is corresponding oligopolymer under catalyst action for polyester after the consumption and divalent alcohol;
(b) esterification: in above-mentioned oligopolymer, add the cyclisation dimethanol, under 200-270 ℃, carry out esterification, slip out excessive terepthaloyl moietie, get corresponding esterification products;
(c) polycondensation: with above-mentioned esterification products under 260-270 ℃ temperature, control reaction system vacuum tightness reduces to less than 100Pa gradually, carries out polycondensation, makes non-crystalline copolyesters.
2. according to claims 1 described method, it is characterized in that the said alcoholysis process of step (a) can be carried out under normal pressure or positive pressure, temperature is 190-250 ℃, and the time is 120-240 minute.
3. according to claims 1 described method, it is characterized in that the said esterification process of step (b) carries out under condition of normal pressure, temperature is 200-270 ℃, and the time is 30-90 minute.
4. according to claims 1 described method, it is characterized in that the said described polycondensation process of step (c) is following:
Reaction kettle was constantly reduced to pressure below the 100Pa in 80 minutes, slip out excessive terepthaloyl moietie and cyclisation divalent alcohol, the temperature of reaction kettle is controlled at 250-270 ℃; Reaction times 180-240 minute; Reaction adds nitrogen after finishing, and makes to be malleation in the reaction kettle, and polymkeric substance is emitted through end of extruded band; Pelletizing, drying.
5. according to claims 1 described method, it is characterized in that: the polyester after the described consumption is selected from one or more mixtures in polyethylene terephthalate, PTT, polybutylene terephthalate, the polyether ester; Polyester beverage bottle, polyester film or trevira that described polyethylene terephthalate reclaims from the consumption back.
6. method according to claim 1 is characterized in that: described divalent alcohol is selected from one or more the mixture in straight chain aliphatic dihydroxy alcohol, the cyclisation aliphatic dihydroxy alcohol.
7. method according to claim 6 is characterized in that: said straight chain aliphatic dihydroxy alcohol is selected from terepthaloyl moietie, 1,2-Ucar 35,1, ammediol, 1; 2-butyleneglycol, 1,4-butyleneglycol, 1,5-pentanediol, 2; 2-dimethyl--1, ammediol, the 2-ethyl-2-tertiary butyl-1, ammediol or 2; 2,4-trimethylammonium-1, the one or more kinds of mixtures in the 6-pinakon; Said cyclisation aliphatic dihydroxy alcohol is selected from pentamethylene glycol, 1,4 cyclohexane dimethanol, 1,2-cyclohexanedimethanol, 1, the one or more kinds of mixtures in 3-cyclohexanedimethanol, 1,4 cyclohexane dimethanol or the Isosorbide.
8. method according to claim 1 is characterized in that: the mol ratio of divalent alcohol and polyester terephthalic acid group is 0.8-2:1 during the said alcoholysis of step (a).
9. method according to claim 1 is characterized in that: the catalyzer of the said alcoholysis step of step (a) is selected from one or more the mixture in the organic metal salt of Ti, Ge, La, Ce, Zn, Fe, Mn, Co, V, Zr, Li, Ca or these elements; The catalyzer that the described polycondensation of step (c) is adopted is an organic titanium.
10. method according to claim 1 is characterized in that: the said polycondensation process of step (c) also adds compound, catalyzer or the stablizer that contains cobalt; Said catalyzer is stibnide, titanium sub-group compound or its mixture.
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Cited By (9)
| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103483567A (en) * | 2013-08-15 | 2014-01-01 | 洛阳市柯莱尔清洗材料有限公司 | Recycled polyester |
| CN109467743A (en) * | 2018-12-26 | 2019-03-15 | 李宁（中国）体育用品有限公司 | Waste and old polyester textile chemistry regeneration method, recycled polyester and polyester hot melting silk |
| CN110777445A (en) * | 2019-11-22 | 2020-02-11 | 浙江海利环保科技股份有限公司 | Preparation method of regenerated polyester fiber |
| CN112608454A (en) * | 2020-11-06 | 2021-04-06 | 珠海华润化学材料科技有限公司 | Basic production formula for preparing non-crystalline copolyester PETG by using recycled PET plastic and process method thereof |
| CN114524924A (en) * | 2020-11-23 | 2022-05-24 | 华润化学材料科技股份有限公司 | Regenerated polyester and preparation method and application thereof |
| CN114736358A (en) * | 2022-04-21 | 2022-07-12 | 河南源宏高分子新材料有限公司 | Preparation method and recovery method of recyclable PETG material |
| CN114787256A (en) * | 2019-10-25 | 2022-07-22 | 伊士曼化工公司 | Copolyesters produced from recycled copolyesters |
| CN115490839A (en) * | 2022-09-21 | 2022-12-20 | 华东理工大学 | Method for preparing PETG/PCTG copolyester by depolymerizing waste PET with mixed alcohol |
| CN115784877A (en) * | 2022-12-06 | 2023-03-14 | 大连理工大学 | Method for recovering dimethyl terephthalate from waste poly (terephthalic acid) -butylene carbonate and repolymerization method |
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| Publication number | Priority date | Publication date | Assignee | Title |
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| CN103483567A (en) * | 2013-08-15 | 2014-01-01 | 洛阳市柯莱尔清洗材料有限公司 | Recycled polyester |
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| CN110777445A (en) * | 2019-11-22 | 2020-02-11 | 浙江海利环保科技股份有限公司 | Preparation method of regenerated polyester fiber |
| CN112608454A (en) * | 2020-11-06 | 2021-04-06 | 珠海华润化学材料科技有限公司 | Basic production formula for preparing non-crystalline copolyester PETG by using recycled PET plastic and process method thereof |
| CN114524924A (en) * | 2020-11-23 | 2022-05-24 | 华润化学材料科技股份有限公司 | Regenerated polyester and preparation method and application thereof |
| CN114736358A (en) * | 2022-04-21 | 2022-07-12 | 河南源宏高分子新材料有限公司 | Preparation method and recovery method of recyclable PETG material |
| CN114736358B (en) * | 2022-04-21 | 2022-12-13 | 河南源宏高分子新材料有限公司 | Preparation method and recovery method of recyclable PETG material |
| CN115490839A (en) * | 2022-09-21 | 2022-12-20 | 华东理工大学 | Method for preparing PETG/PCTG copolyester by depolymerizing waste PET with mixed alcohol |
| CN115490839B (en) * | 2022-09-21 | 2024-03-22 | 华东理工大学 | Method for preparing PETG/PCTG copolyester by depolymerizing waste PET through mixed alcohol |
| CN115784877A (en) * | 2022-12-06 | 2023-03-14 | 大连理工大学 | Method for recovering dimethyl terephthalate from waste poly (terephthalic acid) -butylene carbonate and repolymerization method |
| CN115784877B (en) * | 2022-12-06 | 2024-05-31 | 大连理工大学 | Method for recycling dimethyl terephthalate from waste poly (terephthalic acid) -carbonic acid-butanediol ester and repolymerization method |
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Application publication date: 20120718 |