CN116063664A - Elastic copolyester and preparation method thereof - Google Patents
Elastic copolyester and preparation method thereof Download PDFInfo
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- CN116063664A CN116063664A CN202111272815.1A CN202111272815A CN116063664A CN 116063664 A CN116063664 A CN 116063664A CN 202111272815 A CN202111272815 A CN 202111272815A CN 116063664 A CN116063664 A CN 116063664A
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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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/181—Acids containing aromatic rings
-
- 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
- C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
- C08G63/12—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/16—Dicarboxylic acids and dihydroxy compounds
- C08G63/18—Dicarboxylic acids and dihydroxy compounds the acids or hydroxy compounds containing carbocyclic rings
- C08G63/199—Acids or hydroxy compounds containing cycloaliphatic rings
-
- 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
- C08G63/78—Preparation processes
-
- 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
- C08G63/78—Preparation processes
- C08G63/82—Preparation processes characterised by the catalyst used
- C08G63/85—Germanium, tin, lead, arsenic, antimony, bismuth, titanium, zirconium, hafnium, vanadium, niobium, tantalum, or compounds thereof
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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
Abstract
The invention provides elastic copolyester and a preparation method thereof, which belong to the technical field of high polymer materials and comprise the following steps: 1) Esterification: taking terephthalic acid, isophthalic acid and ethylene glycol as raw materials, and adding a component A and a component B; under the action of titanium catalyst, esterification reaction is carried out; 2) Prepolymerization: carrying out prepolymerization reaction on the reaction system after the esterification reaction in the step 1) is finished to obtain a prepolymerization product; 3) Polycondensation: and (3) carrying out polycondensation reaction on the pre-polymerized product obtained in the step (2) to obtain the elastic copolyester. The elastic copolyester prepared by the invention has better physical properties than the common low-melting-point polyester, the physical properties of the spinning fiber are close to those of the low-melting-point polyamide on the market, the elastic recovery rate reaches 80% when the elongation rate is 10%, and the spinning fiber can be used in the fields of filament sewing threads, ultra-clean wiping cloth bonding, filament web bonding, monofilament web bonding and the like, and has a cost far lower than that of imported low-melting-point polyamide.
Description
Technical Field
The invention relates to the technical field of high polymer materials, in particular to elastic copolyester and a preparation method thereof.
Background
At present, there are two main categories of research and application of low-melting-point fibers at home and abroad: low melting polyesters and low melting polyamides. The development of low-melting point polyester products aims at solving the problem of adhesion with polyester fibers, and the novel modified polyester with lower melting point is realized by adding a modified component in the polymerization process of common polyester to change the molecular structure of PET and simultaneously reduce the crystallinity of PET, thereby achieving the purpose of reducing the melting point. From the development history of thermal bonding fiber, the development of low-melting polyester products is earlier in abroad, and the process technology is mature, for example, japanese imperial company selects a synthesis process similar to PET to prepare low-melting copolyester with good bonding performance for non-woven fabrics. Low melting point copolyester products are also developed in the United states, brazil and other countries. Domestic research on low-melting polyesters began late, beginning at the beginning of the 90 s of the 20 th century.
In the aspect of application of the low-melting-point polyester fiber, the low-melting-point polyester with the foreign melting point lower than 200 ℃ can be used for producing products such as sheath-core composite short fibers and filaments, and is mainly used for filter screens, clothes, bedding, medical care products and the like. Low-melting polyester products with melting points greater than 200 ℃ are generally used to prepare various polyester color master batches. The industrial production of the low-melting-point polyester fiber is realized in China, namely, the company of chemical fiber limited, katai seed fiber science and technology limited, the company of Yutao special fiber limited in Hubei province, xinfeng special fiber factory in Jiaxing city and the like.
The low-melting point polyamide fiber is a high-grade bonding material, is a relatively excellent thermal adhesive in the thermal bonding fiber, has low melting point, high thermal bonding strength and soft hand feeling, does not soften below the melting point, and has excellent oil resistance, wear resistance and solvent resistance. At present, the technology of the foreign low-melting-point polyamide and the fiber thereof is very mature and is widely used in the fields of high-grade textiles, non-woven fabrics, knitting wool, felt, automobile industry, electronics, shoemaking, electric appliances and the like. The nylon hot melt adhesive is researched from the last 80 th century in China, the production technology of low-melting-point polyamide is not mastered at present, and manufacturers of the low-melting-point polyamide are not seen in China. The low melting point polyamide raw material and its fiber still need to be imported and expensive.
The domestic low-melting-point polyester fiber and imported low-melting-point polyamide fiber both occupy a certain market share, and the imported low-melting-point polyamide has high adhesive strength, stable quality and high price when being analyzed from the aspect of product application, and is mainly used in high-grade products, while the low-melting-point polyester is mainly used in medium-low-grade products and mainly depends on the requirements of customer products. Chinese patent CN104558560a discloses a process for preparing a low melting polyester for manufacturing polyester sewing thread. The low-melting-point polyester is prepared by taking terephthalic acid, ethylene glycol, isophthalic acid and linear monomers with dihydroxyl reaction functional groups except ethylene glycol as reaction raw materials. The melting point and the intrinsic viscosity of the polyester product prepared by the invention are lower than those of the conventional polyester, and the polyester product has good solubility when being used for producing the adhesive for solvent bonding wires.
Chinese patent CN102732202a discloses a method for preparing a non-crystalline low-melting-point polyester hot melt adhesive, which uses neopentyl glycol, diethylene glycol, ethylene glycol, adipic acid, sebacic acid and isophthalic acid as raw materials, and makes them react under the action of catalyst, so that the melting point of the obtained copolyester is less than 120 ℃. The polyester hot melt adhesive prepared by the invention is transparent at high temperature and normal temperature, does not crystallize, has good fluidity in low-temperature use, and has excellent wettability.
Chinese patent CN101367915a provides a method for producing low melting point polyester by semi-continuous direct esterification, which is characterized in that terephthalic acid, isophthalic acid and adipic acid are added to ethylene terephthalate, and ethylene glycol and 1, 4-butanediol are intermittently added to react. The beneficial effects of the invention are as follows: the occurrence probability of side reaction can be effectively reduced; the LPET obtained by the reaction has a melting point less than 150 ℃ and good spinnability. The product of the invention can be used as the bonding fiber for the anti-felting treatment of wool products and the bonding fiber for the forming of non-woven fabrics.
Chinese patent CN1962716a discloses a method for synthesizing low-melting polyester, which uses terephthalic acid and ethylene glycol as basic raw materials, and adds isophthalic acid, azelaic acid and neopentyl glycol, and synthesizes the low-melting polyester with melting point of 100-160 ℃ through esterification reaction and polycondensation reaction.
Chinese patent CN1618832a discloses a process for the manufacture of low melting point polyesters from terephthalic acid, isophthalic acid, ethylene glycol and 1, 4-butanediol, by reaction in the presence of a catalyst. The key point of the invention is that the esterification reaction is divided into two stages, which is very effective for reducing the side reaction of 1, 4-butanediol during the esterification reaction. The melting point of the obtained product can be controlled between 100 ℃ and 200 ℃ and the intrinsic viscosity is more than 0.600 dl/g.
At present, the physical properties of the elastic copolyester product with a lower melting point prepared in the prior art document are general, the physical properties of the polyamide with a low melting point can not be achieved, and the application field of the product is limited to medium-low grade products.
Disclosure of Invention
The invention aims to provide elastic copolyester and a preparation method thereof, wherein the prepared elastic copolyester has relatively low melting point, is synthesized based on low melting point polyester, has better physical properties than the common low melting point polyester, and has the physical properties of spun fiber close to the low melting point polyamide on the market, and the elastic recovery rate reaches 80 percent when the elongation is 10 percent and is about one time higher than the common low melting point polyester; the elastic copolyester prepared by the invention can be used in the fields of filament sewing threads, ultra-clean wiping cloth bonding, filament netting bonding, monofilament netting and the like, can replace imported low-melting polyamide in the fields, and has a cost which is much lower than that of imported low-melting polyamide.
The technical scheme of the invention is realized as follows:
the invention provides a preparation method of elastic copolyester, which comprises the following steps:
1) Esterification: taking terephthalic acid, isophthalic acid and ethylene glycol as raw materials, and adding a component A and a component B; under the action of titanium catalyst, esterification reaction is carried out at 200-260 ℃ under normal pressure, and the reaction time is 2-4 hours; wherein, the component A is aliphatic or alicyclic dibasic acid with more than three carbon chains, the component B is aliphatic or alicyclic dibasic alcohol with more than three carbon chains, and the ratio of the total mole number of terephthalic acid, isophthalic acid and the component A to the total mole number of glycol and the component B is 1:1.1 to 1:2.0;
2) Prepolymerization: carrying out prepolymerization reaction on the reaction system after the esterification reaction in the step 1) is finished to obtain a prepolymerization product;
3) Polycondensation: and (3) carrying out polycondensation reaction on the pre-polymerized product obtained in the step (2) to obtain the elastic copolyester.
As a further development of the invention, in step 1), the molar ratio of terephthalic acid to isophthalic acid is 40: 50-95: 5, preferably 50: 50-70: 30, the mole number of the component A accounts for 8 to 25 percent, preferably 10 to 15 percent of the total mole number of the terephthalic acid, the isophthalic acid and the component A; the mole number of the component B accounts for 10 to 60 percent, preferably 20 to 40 percent of the total mole number of the glycol and the component B.
As a further improvement of the present invention, in step 1), the aliphatic dibasic acid is a C3 to C10 aliphatic dibasic acid, and the alicyclic dibasic acid is a C5 to C10 alicyclic dibasic acid; the aliphatic diol is C3-C6 aliphatic diol, and the alicyclic diol is C5-C10 alicyclic diol.
As a further improvement of the present invention, the aliphatic dibasic acid is at least one selected from sebacic acid, adipic acid, glutaric acid or succinic acid, tetrahydrophthalic acid; the aliphatic diol is at least one selected from 1, 4-butanediol, 1, 3-propanediol, 1, 4-cyclohexanedimethanol and neopentyl glycol.
As a further improvement of the invention, in step 1), the titanium catalyst is a silica modified nano-sized titanium dioxide, including products C-94, HOMBIFASTS-06, TY-1 produced by Sachtleben corporation, germany.
As a further improvement of the invention, the weight ratio of the metallic Ti component in the titanium catalyst to the total mass of all raw materials is 1: 10000-1: 100000. preferably, 1:30000-1:60000.
As a further improvement of the invention, in the step 2), the prepolymerization temperature is 240-265 ℃, the vacuum degree is 200-300 Pa, and the duration is 1-2.5 hours.
As a further improvement of the invention, in the step 3), the polycondensation temperature is 240-275 ℃, the vacuum degree is less than or equal to 200Pa, and the polycondensation time is 2-4 hours.
The invention further protects the elastic copolyester prepared by the preparation method.
As a further improvement of the invention, the elastic copolyester has a viscosity of more than 0.6, a breaking strength of more than 0.42N/tex, an elongation at break of more than 30%, an initial modulus of more than 2N/tex and a specific elongation rebound (elongation 10%) of more than 75%.
The invention has the following beneficial effects: the elastic copolyester prepared by the invention has relatively low melting point, is synthesized based on low melting point polyester, has better physical property than common low melting point polyester, and has the physical property of spinning fiber close to low melting point polyamide on the market, and when the elongation is 10 percent, the elastic recovery rate reaches 80 percent and is about doubled compared with common low melting point polyester; the elastic copolyester prepared by the invention can be used in the fields of filament sewing threads, ultra-clean wiping cloth bonding, filament netting bonding, monofilament netting and the like, can replace imported low-melting polyamide in the fields, and has a cost which is much lower than that of imported low-melting polyamide.
1) The elastic copolyester prepared by the invention has a melting point of 110-140 ℃ and an intrinsic viscosity of more than 0.630 dl/g; the physical property of the fiber is better than that of common low-melting-point polyester, the physical property of the spinning fiber is close to that of low-melting-point polyamide on the market, and when the elongation is 12 percent, the elastic recovery rate reaches 85 percent and is about doubled compared with that of common low-melting-point polyester.
2) The elastic copolyester prepared by the invention can be used in the fields of filament sewing threads, ultra-clean wiping cloth bonding, filament netting bonding, monofilament netting and the like, can replace imported low-melting polyamide in the fields, and has a cost which is much lower than that of imported low-melting polyamide.
3) The preparation method of the invention uses high-efficiency nontoxic titanium catalyst, has small addition amount, improves esterification and polymerization reaction speeds, ensures that the product does not contain heavy metals, and accords with environmental protection trend.
Detailed Description
The following description of the technical solutions in the embodiments of the present invention will be clear and complete, and it is obvious that the described embodiments are only some embodiments of the present invention, but not all embodiments. All other embodiments, which can be made by those skilled in the art based on the embodiments of the invention without making any inventive effort, are intended to be within the scope of the invention.
Example 1
The embodiment provides a preparation method of elastic copolyester, which specifically comprises the following steps:
1) Mixing 500g of terephthalic acid, 332g of isophthalic acid, 400g of ethylene glycol, 85g of sebacic acid and 260g of neopentyl glycol, carrying out esterification reaction at 245 ℃ under normal pressure, removing generated water in the reaction process, and finishing esterification when the esterification rate reaches 92%;
2) Prepolymerization: when the reaction is finished, slowly pumping low vacuum into the system, wherein the vacuum degree is 220Pa, the temperature is 262 ℃, and the duration is 1.5 hours;
3) Polycondensation: and then high vacuum is pumped, the vacuum degree is 25Pa, the temperature is 271 ℃, and the duration is 3 hours, so that the elastic copolyester is prepared.
The formulations of examples 2 to 3 and comparative examples 1 to 2 are shown in the following Table 1, and elastomeric copolyesters were prepared under the same conditions and procedures as in example 1.
TABLE 1
Test example 1
The elastic copolyesters prepared in examples 1 to 3 and comparative examples 1 to 2 of the present invention, and commercially available low-melting nylon (Yueyang petrochemical PA 6) were subjected to performance test, and the results are shown in Table 2.
The method for measuring the viscosity comprises the following steps: the test was performed using an automatic viscometer using the GB/T14189-93 standard. Using 1:1 phenol/tetrachloroethane as solvent, the dissolution temperature of the slice is 90-100 ℃, and the temperature control range of the water bath of the viscometer is 25+/-0.05 ℃.
The melting point test method comprises the following steps: the test was carried out by using a polarizing microscope using GB/T14189-93 standard.
TABLE 2
As shown in the table, the elastic copolyester has low melting point and good elasticity, the physical property of the elastic copolyester is better than that of common low-melting-point polyester, the physical property of the spinning fiber of the elastic copolyester is close to that of low-melting-point polyamide on the market, and when the elongation is 10%, the elastic recovery rate reaches 80%, which is about one time higher than that of common low-melting-point polyester; the spinning fiber can be used in the fields of filament sewing threads, ultra-clean wiping cloth bonding, filament netting bonding, monofilament netting and the like, can replace imported low-melting polyamide applied in the fields, and has a cost which is far lower than that of imported low-melting polyamide. The method is simple, convenient and easy to control, has low equipment requirement, saves energy and reduces emission, and has good prospect.
The foregoing description of the preferred embodiments of the invention is not intended to be limiting, but rather is intended to cover all modifications, equivalents, alternatives, and improvements that fall within the spirit and scope of the invention.
Claims (10)
1. A process for the preparation of an elastic copolyester comprising the steps of:
1) Esterification: taking terephthalic acid, isophthalic acid and ethylene glycol as raw materials, and adding a component A and a component B; under the action of titanium catalyst, esterification reaction is carried out at 200-260 ℃ under normal pressure, and the reaction time is 2-4 hours; wherein, the component A is aliphatic or alicyclic dibasic acid with more than three carbon chains, the component B is aliphatic or alicyclic dibasic alcohol with more than three carbon chains, and the ratio of the total mole number of terephthalic acid, isophthalic acid and the component A to the total mole number of glycol and the component B is 1:1.1 to 1:2.0;
2) Prepolymerization: carrying out prepolymerization reaction on the reaction system after the esterification reaction in the step 1) is finished to obtain a prepolymerization product;
3) Polycondensation: and (3) carrying out polycondensation reaction on the pre-polymerized product obtained in the step (2) to obtain the elastic copolyester.
2. The process according to claim 1, wherein in step 1), the molar ratio of terephthalic acid to isophthalic acid is 40: 50-95: 5, preferably 50: 50-70: 30, the mole number of the component A accounts for 8 to 25 percent, preferably 10 to 15 percent of the total mole number of the terephthalic acid, the isophthalic acid and the component A; the mole number of the component B accounts for 10 to 60 percent, preferably 20 to 40 percent of the total mole number of the glycol and the component B.
3. The method according to claim 1, wherein in step 1), the aliphatic dibasic acid is a C3 to C10 aliphatic dibasic acid, and the alicyclic dibasic acid is a C5 to C10 alicyclic dibasic acid; the aliphatic diol is C3-C6 aliphatic diol, and the alicyclic diol is C5-C10 alicyclic diol.
4. The method according to claim 3, wherein the aliphatic dibasic acid is at least one selected from the group consisting of sebacic acid, adipic acid, glutaric acid, succinic acid, and tetrahydrophthalic acid; the aliphatic diol is at least one selected from 1, 4-butanediol, 1, 3-propanediol, 1, 4-cyclohexanedimethanol and neopentyl glycol.
5. The process according to claim 1, wherein in step 1) the titanium catalyst is a silica modified nano-sized titanium dioxide, comprising products C-94, HOMBIFASTS-06, TY-1, manufactured by Sachtleben company, germany.
6. The preparation method according to claim 5, wherein the weight ratio of the metallic Ti component in the titanium catalyst to the total mass of all raw materials is 1: 10000-1: 100000. preferably, 1:30000-1:60000.
7. The process according to claim 1, wherein in step 2), the prepolymerization temperature is 240 to 265℃and the vacuum is 200 to 300Pa for 1 to 2.5 hours.
8. The process according to claim 1, wherein in step 3), the polycondensation temperature is 240 to 275℃and the vacuum degree is not more than 200Pa, and the polycondensation time is 2 to 4 hours.
9. An elastomeric copolyester obtainable by the process according to any one of claims 1 to 8.
10. The elastic copolyester of claim 9, wherein the elastic copolyester has a viscosity of greater than 0.6, a breaking strength of greater than 0.42N/tex, an elongation at break of greater than 30%, an initial modulus of greater than 2N/tex, and a specific elongation rebound (10% elongation) of greater than 75%.
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