CN104449520A - Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof - Google Patents
Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof Download PDFInfo
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- CN104449520A CN104449520A CN201410819740.8A CN201410819740A CN104449520A CN 104449520 A CN104449520 A CN 104449520A CN 201410819740 A CN201410819740 A CN 201410819740A CN 104449520 A CN104449520 A CN 104449520A
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- acid
- ethylene
- terpolymer
- terephthalic acid
- smelting point
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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
- C08G63/66—Polyesters containing oxygen in the form of ether groups
- C08G63/668—Polyesters containing oxygen in the form of ether groups derived from polycarboxylic acids and polyhydroxy compounds
- C08G63/672—Dicarboxylic acids and dihydroxy compounds
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J11/00—Features of adhesives not provided for in group C09J9/00, e.g. additives
- C09J11/08—Macromolecular additives
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09J—ADHESIVES; NON-MECHANICAL ASPECTS OF ADHESIVE PROCESSES IN GENERAL; ADHESIVE PROCESSES NOT PROVIDED FOR ELSEWHERE; USE OF MATERIALS AS ADHESIVES
- C09J167/00—Adhesives based on polyesters obtained by reactions forming a carboxylic ester link in the main chain; Adhesives based on derivatives of such polymers
- C09J167/02—Polyesters derived from dicarboxylic acids and dihydroxy compounds
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyesters Or Polycarbonates (AREA)
Abstract
The invention discloses a noncrystalline high-melting-point polyester hot melt adhesive and a preparation method thereof. Because a specific formula proportion and a specific ethylene terpolymer are adopted to modify polyester, the comprehensive performance of the polyester hot melt adhesive prepared according to the invention is improved, and has a relatively high melting point and a relatively soft handfeel, and therefore, the polyester hot melt adhesive and a preparation method thereof disclosed by the invention are extremely applicable to the field of textile adhesion.
Description
Technical field
The present invention relates to a kind of noncrystalline polyester thermosol with high smelting point and preparation method thereof.
Background technology
Polyester hot-melt adhesive known at present adopts the aromatic acids such as terephthalic acid (or dibasic acid dimethyl ester) and long-chain fat race diprotic acid (or dibasic acid dimethyl ester), dibasic alcohol to obtain after esterification (or transesterify), polycondensation mostly.Polyester hot melt adhesive product generally has two kinds of situations, and a kind of situation is that fusing point design is lower, and fusing point as whole in DSC is lower than 100 DEG C, the not easily crystallization of this hot melt adhesive, feel is relatively soft, but the caking that is easily clamminess during production discharging, bring difficulty to production, production efficiency is lower; Another kind of situation is that fusing point design is higher, fusing point as whole in DSC higher than 110 DEG C, the easy crystallization of this hot melt adhesive, but the feel of hot melt adhesive and quality are comparatively hard, crisp and easily break.
Summary of the invention
The object of the invention is to, solve the problems of the technologies described above, a kind of amorphism polyester thermosol with high smelting point and preparation method thereof is provided.
The technical solution adopted in the present invention is:
A kind of amorphism polyester thermosol with high smelting point, its composition comprises: the total dicarboxylic acid be made up of terephthalic acid, m-phthalic acid and aliphatic dibasic acid, by ethylene glycol, Diethylene Glycol and 1, total dibasic alcohol that 5-pentanediol forms, catalyzer, stablizer, oxidation inhibitor and ethylene-dien terpolymer, the proportioning of each composition is:
Above-mentioned total dicarboxylic acid: the mol ratio of total dibasic alcohol is 1:1.5 ~ 1.7;
Above-mentioned terephthalic acid
:m-phthalic acid: the mol ratio of aliphatic dicarboxylic acid is 1: 0.10 ~ 0.12: 0.125 ~ 0.2;
Above-mentioned ethylene glycol: Diethylene Glycol: the mol ratio of 1,5-PD is 1: 0.1 ~ 0.25:0.1 ~ 0.25;
Above-mentioned catalyzer is selected from the one in tetra-n-butyl titanate, titanium isopropylate, tetraethyl titanate, and its content is 0.06% ~ 0.2% of terephthalic acid quality;
Aforementioned stable agent is trimethyl phosphite 99 or triphenyl phosphite, and its content is 0.01% ~ 0.05% of terephthalic acid quality;
The content of above-mentioned oxidation inhibitor is 0.25% ~ 0.3% of terephthalic acid quality;
Above-mentioned ethylene-dien terpolymer is selected from the one in ethene-vinyl acetate-carbonyl terpolymer, ethylene/n-butyl acrylate-carbonyl terpolymer or ethylene/n-butyl acrylate-glycidyl ester terpolymer, and its content is the 1%-5% of terephthalic acid quality;
Above-mentioned aliphatic dibasic acid is selected from 1,6-hexanodioic acid, 1, the one in 10 sebacic acid, 1,12-dodecanedioic acid.
A preparation method for amorphism polyester thermosol with high smelting point, take mentioned component as raw material, carries out following step:
(1) by terephthalic acid, m-phthalic acid, aliphatic dibasic acid, ethylene glycol, Diethylene Glycol and 1,5-pentanediol carries out esterification under the effect of catalyzer, temperature of reaction 150 ~ 250 DEG C, when the quantity of distillate of water is 90 ~ 95% of theory, esterification terminates;
(2) stablizer, oxidation inhibitor are joined in the product of step (1), 250-260 DEG C, carry out decompression polycondensation, reaction times 2 ~ 3h under 100 ~ 133 Pa pressure, reaction terminates rear introducing nitrogen and removes vacuum;
(3) under nitrogen protection, added by ethylene-dien terpolymer in the product of step (2), open vacuum and continue to stir 0.5h, discharging while hot after releasing vacuum, can obtain target product.
Beneficial effect of the present invention
The present invention, owing to adopting specific formula rate, utilizes specific ethylene-dien terpolymer to carry out modified poly ester, makes to possess higher fusing point by the polyester hot-melt adhesive obtained by the present invention and feel flexible relative not easy fracture, is highly suitable for bonding of textiles field.
Embodiment
Embodiment 1
A kind of amorphism polyester thermosol with high smelting point, comprise: terephthalic acid 166g, m-phthalic acid 16.6g, 1,6-hexanodioic acid 29.29g, ethylene glycol 89.595 g, Diethylene Glycol 15.3g, 1,5-PD 37.5g, tetra-n-butyl titanate 0.0996g, trimethyl phosphite 99 0.0166g, oxidation inhibitor 0.415g, ethylene/n-butyl acrylate-carbonyl terpolymer 1.66g.
A preparation method for amorphism polyester thermosol with high smelting point, step is as follows:
(1) by above-mentioned terephthalic acid, m-phthalic acid, 1,6-hexanodioic acid, ethylene glycol, Diethylene Glycol and 1,5-pentanediol carries out esterification under the effect of catalyzer tetra-n-butyl titanate, temperature of reaction 150 ~ 250 DEG C, when the quantity of distillate of water is 90 ~ 95% of theory, esterification terminates;
(2) add stablizer trimethyl phosphite 99, oxidation inhibitor, 250-260 DEG C, carry out decompression polycondensation, reaction times 2 ~ 3h under 100 ~ 133 Pa pressure, reaction terminates rear introducing nitrogen and removes vacuum;
(3) add ethylene/n-butyl acrylate-carbonyl terpolymer, open vacuum stirring 0.5h, then remove vacuum discharging while hot.
A1 is designated as by the product obtained by embodiment 1.
Comparative example 1
A kind of polyester hot-melt adhesive, its raw material composition is not except comprising ethylene/n-butyl acrylate-carbonyl terpolymer beyond the region of objective existence, and all the other are identical with embodiment 1;
Its preparation method also duplicates with the method in embodiment 1, but because not containing ethylene-dien terpolymer, step (2) namely removes vacuum discharging while hot after having reacted;
Product obtained by comparative example 1 is designated as B1.
Embodiment 2
A kind of amorphism polyester thermosol with high smelting point, comprise: terephthalic acid 166g, m-phthalic acid 19.92g, 1,10-sebacic acid 18.25g, ethylene glycol 93 g, Diethylene Glycol 39.75g, 1,5-PD 15.62g, titanium isopropylate 0.332g, triphenyl phosphite 0.083g, oxidation inhibitor 0.498g, ethene-vinyl acetate-carbonyl terpolymer 8.3g.
A preparation method for amorphism polyester thermosol with high smelting point, step is as follows:
(1) by above-mentioned terephthalic acid, m-phthalic acid, 1,10-sebacic acid, ethylene glycol, Diethylene Glycol and 1,5-pentanediol carries out esterification under the effect of catalyzer titanium isopropylate, temperature of reaction 150 ~ 250 DEG C, when the quantity of distillate of water is 90 ~ 95% of theory, esterification terminates;
(2) add stablizer triphenyl phosphite, oxidation inhibitor, 250-260 DEG C, carry out decompression polycondensation, reaction times 2 ~ 3h under 100 ~ 133 Pa pressure, reaction terminates rear introducing nitrogen and removes vacuum;
(3) add ethene-vinyl acetate-carbonyl terpolymer, open vacuum stirring 0.5h, then remove vacuum discharging while hot.
A2 is designated as by the product obtained by embodiment 2.
Comparative example 2
A kind of polyester hot-melt adhesive, its raw material composition is not except comprising ethene-vinyl acetate-carbonyl terpolymer beyond the region of objective existence, and all the other are identical with embodiment 2;
Its preparation method also duplicates with the method in embodiment 2, but because not containing ethene-vinyl acetate-carbonyl terpolymer, step (2) namely removes vacuum discharging while hot after having reacted;
Product obtained by comparative example 2 is designated as B2.
Embodiment 3
A kind of amorphism polyester thermosol with high smelting point, comprise: terephthalic acid 166g, m-phthalic acid 18.26g, 1,12-dodecanedioic acid 21.9g, ethylene glycol 94.1g, Diethylene Glycol 32.178g, 1,5-PD 31.6g, tetraethyl titanate 0.166g, trimethyl phosphite 99 0.0498g, oxidation inhibitor 0.4648g, ethylene/n-butyl acrylate-glycidyl ester terpolymer 4.98g.
A preparation method for amorphism polyester thermosol with high smelting point, step is as follows:
(1) by above-mentioned terephthalic acid, m-phthalic acid, 1,12-dodecanedioic acid, ethylene glycol, Diethylene Glycol and 1,5-pentanediol carries out esterification under the effect of catalyzer tetraethyl titanate, temperature of reaction 150 ~ 250 DEG C, when the quantity of distillate of water is 90 ~ 95% of theory, esterification terminates;
(2) add stablizer trimethyl phosphite 99, oxidation inhibitor, 250-260 DEG C, carry out decompression polycondensation, reaction times 2 ~ 3h under 100 ~ 133 Pa pressure, reaction terminates rear introducing nitrogen and removes vacuum;
(3) add ethylene/n-butyl acrylate-glycidyl ester terpolymer, open vacuum stirring 0.5h, then remove vacuum discharging while hot.
A3 is designated as by the product obtained by embodiment 3.
Comparative example 3
A kind of polyester hot-melt adhesive, its raw material composition is not except comprising ethylene/n-butyl acrylate-glycidyl ester terpolymer beyond the region of objective existence, and all the other are identical with embodiment 3;
Its preparation method also duplicates with the method in embodiment 3, but because not containing ethylene/n-butyl acrylate-glycidyl ester terpolymer, step (2) namely removes vacuum discharging while hot after having reacted;
Product obtained by comparative example 3 is designated as B3.
Product index of correlation is tested
According to the index test of embodiment 1 ~ 3 and comparative example 1 ~ 3 products obtained therefrom, all carry out according to hot melt adhesive field traditional test methods and standard, concrete test result is as shown in table 1 below.
Table 1: embodiment and each product test result of comparative example
Can as apparent from upper table 1, by special formulation provided by the invention and preparation method, the over-all properties of obtained polyester hot-melt adhesive has obvious lifting, and particularly it possesses higher fusing point and feel flexible relative, is highly suitable for the daily necessities bonding fields such as the clothes of light colour, sofa.
Claims (5)
1. an amorphism polyester thermosol with high smelting point, its composition comprise be made up of terephthalic acid, m-phthalic acid and aliphatic dibasic acid total dicarboxylic acid, by ethylene glycol, Diethylene Glycol and 1, total dibasic alcohol, stablizer, catalyzer, the oxidation inhibitor of 5-pentanediol composition, it is characterized in that, its composition also comprises ethylene-dien terpolymer, and the proportioning of each composition is:
Described total dicarboxylic acid: the mol ratio of described total dibasic alcohol is 1:1.5 ~ 1.7;
Described terephthalic acid
:described m-phthalic acid: the mol ratio of described aliphatic dicarboxylic acid is 1: 0.10 ~ 0.12: 0.125 ~ 0.2;
Described ethylene glycol: described Diethylene Glycol: the mol ratio of described 1,5-PD is 1: 0.1 ~ 0.25:0.1 ~ 0.25;
The content of described catalyzer is 0.06% ~ 0.2% of described terephthalic acid quality;
The content of described stablizer is 0.01% ~ 0.05% of described terephthalic acid quality;
The content of described oxidation inhibitor is 0.25% ~ 0.3% of described terephthalic acid quality;
Described ethylene-dien terpolymer is selected from the one in ethene-vinyl acetate-carbonyl terpolymer, ethylene/n-butyl acrylate-carbonyl terpolymer or ethylene/n-butyl acrylate-glycidyl ester terpolymer, and its content is the 1%-5% of described terephthalic acid quality.
2. amorphism polyester thermosol with high smelting point as claimed in claim 1, it is characterized in that, described aliphatic dibasic acid is selected from the one in 1,6-hexanodioic acid, 1,10-sebacic acid, 1,12-dodecanedioic acid.
3. amorphism polyester thermosol with high smelting point as claimed in claim 1, it is characterized in that, described catalyzer is selected from the one in tetra-n-butyl titanate, titanium isopropylate, tetraethyl titanate.
4. amorphism polyester thermosol with high smelting point as claimed in claim 1, it is characterized in that, described stablizer is trimethyl phosphite 99 or triphenyl phosphite.
5. a preparation method for amorphism polyester thermosol with high smelting point, is characterized in that, consists of basis, carry out following step with the raw material of the amorphism polyester thermosol with high smelting point described in described any one of claim 1 ~ 4:
(1) by terephthalic acid, m-phthalic acid, aliphatic dibasic acid, ethylene glycol, Diethylene Glycol and 1,5-pentanediol carries out esterification under the effect of catalyzer, temperature of reaction 150 ~ 250 DEG C, when the quantity of distillate of water is 90 ~ 95% of theory, esterification terminates;
(2) stablizer, oxidation inhibitor are joined in the product of step (1), 250-260 DEG C, carry out decompression polycondensation, reaction times 2 ~ 3h under 100 ~ 133 Pa pressure, reaction terminates rear introducing nitrogen and removes vacuum;
(3) under nitrogen protection, added by ethylene-dien terpolymer in the product of step (2), open vacuum and continue to stir 0.5h, discharging while hot after releasing vacuum, can obtain target product.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410819740.8A CN104449520A (en) | 2014-12-25 | 2014-12-25 | Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof |
| PCT/CN2015/098468 WO2016101895A1 (en) | 2014-12-25 | 2015-12-23 | Non-crystalline high melting point polyester hot-melt adhesive and preparation method therefor |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN201410819740.8A CN104449520A (en) | 2014-12-25 | 2014-12-25 | Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof |
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| Publication Number | Publication Date |
|---|---|
| CN104449520A true CN104449520A (en) | 2015-03-25 |
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| CN201410819740.8A Pending CN104449520A (en) | 2014-12-25 | 2014-12-25 | Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof |
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| Country | Link |
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| CN (1) | CN104449520A (en) |
| WO (1) | WO2016101895A1 (en) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016101895A1 (en) * | 2014-12-25 | 2016-06-30 | 上海天洋热熔粘接材料股份有限公司 | Non-crystalline high melting point polyester hot-melt adhesive and preparation method therefor |
| CN115584218A (en) * | 2022-12-05 | 2023-01-10 | 广州鹿山新材料股份有限公司 | PES (polyether sulfone) hot melt adhesive film as well as preparation method and application thereof |
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|---|---|---|---|---|
| CN114075423A (en) * | 2020-08-17 | 2022-02-22 | 上海天洋热熔粘接材料股份有限公司 | Low-surface-energy copolyester hot melt adhesive and preparation method thereof |
| CN114573956B (en) * | 2022-01-25 | 2023-11-24 | 浙江恒逸石化研究院有限公司 | Preparation method of nano magnesium hydroxide modified degradable copolyester |
| CN115044348B (en) * | 2022-07-13 | 2023-05-16 | 广州市嘉雁粘合剂有限公司 | EMS (energy management system) label hot melt adhesive with strong stripping force and easy cutting and preparation method thereof |
| CN118459740B (en) * | 2024-07-10 | 2024-09-27 | 山东广垠新材料有限公司 | High damping polyester elastomer and preparation method thereof |
Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0984052A1 (en) * | 1998-08-24 | 2000-03-08 | Premark RWP Holdings, Inc. | Thin film adhesive, method of making, products made therefrom |
| CN103059359A (en) * | 2012-11-20 | 2013-04-24 | 深圳市沃尔核材股份有限公司 | Soft and flexible heat-shrinkable tube with properties of high fire retardance and oil resistance and production method thereof |
| CN103509511A (en) * | 2012-06-16 | 2014-01-15 | 上海天洋热熔胶有限公司 | Non-crystalline low-melting-point polyester hot-melt adhesive preparation method |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN104449520A (en) * | 2014-12-25 | 2015-03-25 | 上海天洋热熔粘接材料股份有限公司 | Noncrystalline high-melting-point polyester hot melt adhesive and preparation method thereof |
-
2014
- 2014-12-25 CN CN201410819740.8A patent/CN104449520A/en active Pending
-
2015
- 2015-12-23 WO PCT/CN2015/098468 patent/WO2016101895A1/en active Application Filing
Patent Citations (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0984052A1 (en) * | 1998-08-24 | 2000-03-08 | Premark RWP Holdings, Inc. | Thin film adhesive, method of making, products made therefrom |
| CN103509511A (en) * | 2012-06-16 | 2014-01-15 | 上海天洋热熔胶有限公司 | Non-crystalline low-melting-point polyester hot-melt adhesive preparation method |
| CN103059359A (en) * | 2012-11-20 | 2013-04-24 | 深圳市沃尔核材股份有限公司 | Soft and flexible heat-shrinkable tube with properties of high fire retardance and oil resistance and production method thereof |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2016101895A1 (en) * | 2014-12-25 | 2016-06-30 | 上海天洋热熔粘接材料股份有限公司 | Non-crystalline high melting point polyester hot-melt adhesive and preparation method therefor |
| CN115584218A (en) * | 2022-12-05 | 2023-01-10 | 广州鹿山新材料股份有限公司 | PES (polyether sulfone) hot melt adhesive film as well as preparation method and application thereof |
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| Publication number | Publication date |
|---|---|
| WO2016101895A1 (en) | 2016-06-30 |
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Application publication date: 20150325 |