CN114075423A - Low-surface-energy copolyester hot melt adhesive and preparation method thereof - Google Patents
Low-surface-energy copolyester hot melt adhesive and preparation method thereof Download PDFInfo
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- CN114075423A CN114075423A CN202010824324.2A CN202010824324A CN114075423A CN 114075423 A CN114075423 A CN 114075423A CN 202010824324 A CN202010824324 A CN 202010824324A CN 114075423 A CN114075423 A CN 114075423A
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- acid
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- 239000004831 Hot glue Substances 0.000 title claims abstract description 39
- 229920001634 Copolyester Polymers 0.000 title claims abstract description 26
- 238000002360 preparation method Methods 0.000 title claims abstract description 9
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims abstract description 44
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims abstract description 42
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 claims abstract description 37
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 claims abstract description 28
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 claims abstract description 28
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 claims abstract description 28
- 239000000463 material Substances 0.000 claims abstract description 26
- 239000002253 acid Substances 0.000 claims abstract description 25
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims abstract description 20
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 claims abstract description 19
- 229940075507 glyceryl monostearate Drugs 0.000 claims abstract description 15
- 239000001788 mono and diglycerides of fatty acids Substances 0.000 claims abstract description 15
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 claims abstract description 14
- 238000006243 chemical reaction Methods 0.000 claims description 36
- 239000003963 antioxidant agent Substances 0.000 claims description 15
- 230000003078 antioxidant effect Effects 0.000 claims description 15
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 14
- 238000006068 polycondensation reaction Methods 0.000 claims description 14
- 239000003054 catalyst Substances 0.000 claims description 13
- 238000005886 esterification reaction Methods 0.000 claims description 12
- 238000007599 discharging Methods 0.000 claims description 7
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- YHWCPXVTRSHPNY-UHFFFAOYSA-N butan-1-olate;titanium(4+) Chemical group [Ti+4].CCCC[O-].CCCC[O-].CCCC[O-].CCCC[O-] YHWCPXVTRSHPNY-UHFFFAOYSA-N 0.000 claims description 5
- 150000007513 acids Chemical class 0.000 claims description 3
- 150000001298 alcohols Chemical class 0.000 claims 2
- 238000004519 manufacturing process Methods 0.000 claims 2
- 230000001070 adhesive effect Effects 0.000 abstract description 3
- 239000002994 raw material Substances 0.000 abstract description 2
- 229920000728 polyester Polymers 0.000 description 13
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 5
- 230000032050 esterification Effects 0.000 description 5
- 229910052731 fluorine Inorganic materials 0.000 description 5
- 239000011737 fluorine Substances 0.000 description 5
- 238000002844 melting Methods 0.000 description 4
- 230000008018 melting Effects 0.000 description 4
- 238000012360 testing method Methods 0.000 description 4
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 3
- 150000001335 aliphatic alkanes Chemical class 0.000 description 3
- 239000004744 fabric Substances 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 229910052710 silicon Inorganic materials 0.000 description 3
- 239000010703 silicon Substances 0.000 description 3
- 238000005406 washing Methods 0.000 description 3
- 239000000853 adhesive Substances 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 230000009477 glass transition Effects 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 238000011056 performance test Methods 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- 230000032683 aging Effects 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 150000002009 diols Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002708 enhancing effect Effects 0.000 description 1
- 125000004185 ester group Chemical group 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
- 238000004806 packaging method and process Methods 0.000 description 1
- 238000007719 peel strength test Methods 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000011112 process operation Methods 0.000 description 1
- 230000003075 superhydrophobic effect Effects 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
Classifications
-
- 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
-
- 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
-
- 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
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (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 low surface energy copolyester hot melt adhesive and a preparation method thereof, wherein the raw materials of the hot melt adhesive comprise main materials and auxiliary materials, wherein the main materials comprise dibasic acid and dihydric alcohol, the dibasic acid is prepared by mixing terephthalic acid, isophthalic acid and sebacic acid according to a specific proportion, and the dihydric alcohol glyceryl monostearate, butanediol, diethylene glycol and ethylene glycol are mixed according to a specific proportion. The invention creatively introduces the glyceryl monostearate material into the system, designs the whole material proportion, reduces the surface energy of the product, and greatly improves the adhesive property and the water resistance of the product to the low-surface-energy material. Meanwhile, as the glyceryl monostearate material has wide source and lower price, the application field of the low surface energy copolyester hot melt adhesive can be effectively expanded.
Description
Technical Field
The invention relates to a copolyester hot melt adhesive and a synthesis preparation method thereof, in particular to the copolyester hot melt adhesive suitable for bonding low surface energy materials and the preparation method thereof.
Background
The polyester hot melt adhesive is a solvent-free green environment-friendly adhesive which is rapidly developed in recent ten years, is mainly connected through ester groups among chain links, has the advantages of rapid bonding, simple process, excellent heat resistance, aging resistance and the like, and can be widely applied to industries of clothes, packaging, wood and the like.
However, the conventional polyester hot melt adhesive structure contains a large amount of ester bonds, so that the polarity of the product is generally higher, thereby limiting the application of the product in the field of low surface energy materials. In order to reduce the surface energy of the polyester hot melt adhesive, CN107325272A discloses a semi-aromatic polyester hot melt adhesive containing an organic silicon macromolecular block and a preparation method thereof, which mainly introduces an organic silicon glycol macromolecular block into the semi-aromatic polyester hot melt adhesive, reduces the glass transition temperature of the product, improves the low-temperature flexibility and the bonding stability of the product, and simultaneously improves the bonding performance of the product to the difficult-to-bond materials such as silicon-treated fabrics. In addition, fluorine is the strongest among known elements, and the bond energy of the C-F bond is higher and the bond length is longer, so that the surface energy of the polyester hot melt adhesive can be reduced by introducing the fluorine into the polyester hot melt adhesive structure. However, because the raw materials of the organosilicon and fluorine products are expensive and not easily available, the introduction of the organosilicon and fluorine products into a polyester hot melt adhesive system will inevitably increase the cost of the polyester hot melt adhesive, and further limit the industrial application of the organosilicon and fluorine products.
Therefore, how to obtain a novel low surface energy copolyester hot melt adhesive to expand the application market of the copolyester hot melt adhesive becomes a problem to be solved.
Disclosure of Invention
The invention aims to solve the technical problems and provides a novel low-surface-energy copolyester hot melt adhesive and a preparation method thereof, so that the copolyester hot melt adhesive prepared by the invention has a low surface energy characteristic, and has excellent bonding effect and water washing resistance when a low-surface-energy material is bonded and applied.
The technical scheme adopted by the invention is as follows: the copolyester hot melt adhesive with low surface energy comprises main materials and auxiliary materials, wherein the main materials comprise dibasic acid and dihydric alcohol, and the auxiliary materials comprise a catalyst and an antioxidant. Wherein the dibasic acid is composed of a mixture of terephthalic acid, isophthalic acid and sebacic acid; the dihydric alcohol is composed of glyceryl monostearate, butanediol, diethylene glycol and ethylene glycol mixture
The molar ratio of the dibasic acid to the dihydric alcohol is 1: 1.5;
and among the dibasic acids, terephthalic acid: isophthalic acid: the mole ratio of sebacic acid is 1: 0.23-0.57: 0.03 to 0.1;
and among the diols, glyceryl monostearate: butanediol: diethylene glycol: the molar ratio of the ethylene glycol is as follows: 1: 0.3-0.75: 0.2-0.38: 0.17 to 0.38;
in the dihydric alcohol, the glycerin monostearate is dihydric alcohol containing 17 side alkane long chains, and the structural formula of the glycerin monostearate is specifically as follows:
the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.05 percent of the total mass of the dibasic acid;
the antioxidant is 1010, and the addition amount of the antioxidant is 0.03 percent of the total mass of the dibasic acid.
The preparation method of the low-surface-energy copolyester hot melt adhesive comprises the following steps:
(1) adding dibasic acid consisting of a mixture of terephthalic acid, isophthalic acid and sebacic acid, dihydric alcohol consisting of a mixture of glyceryl monostearate, butanediol, diethylene glycol and ethylene glycol, and a catalyst into a reaction kettle according to a preset proportion, wherein the reaction temperature is 165-225 ℃, and the esterification reaction is finished when the amount of water produced by the reaction reaches 9% or more of the theoretical water yield;
(2) adding a predetermined amount of antioxidant into the product obtained in the step (1), carrying out reduced pressure polycondensation reaction at 235-250 ℃ under the condition of 90-180 Pa, and finishing the polycondensation reaction after 1.5-2 h;
(3) introducing nitrogen, removing vacuum, and discharging when it is hot.
In the invention, the glyceryl monostearate is mainly used for reducing the surface energy of the system and enhancing the water resistance of the system; the terephthalic acid and the isophthalic acid are used for ensuring the bonding performance of the product; the sebacic acid is used for reducing the glass transition temperature of the system and improving the flexibility of the product; butanediol, diethylene glycol and ethylene glycol are mainly used for adjusting the melting point of the product and reducing the product cost.
The invention has the advantages that: the material of glyceryl monostearate is creatively introduced into the system, and the integral material proportion is designed. Because the glyceryl monostearate is dihydric alcohol containing 17 side alkane long chains, and methyl and methylene are hydrophobic chain segments, after the system is crystallized, the hydrophobic chain segments of the long alkane side chains of the glyceryl monostearate are transferred to the surface of the copolyester hot melt adhesive, so that the surface energy of the product is reduced, and the bonding performance and the water washing resistance of the product to the low-surface-energy material are greatly improved. Meanwhile, as the glyceryl monostearate material has wide source and lower price, the application field of the low-surface-energy polyester hot melt adhesive can be effectively expanded.
Detailed Description
The present invention will be further specifically described with reference to the following examples, but the present invention is not limited thereto.
Example 1
Adding mixed dibasic acid consisting of 109.65g of terephthalic acid, 62.13g of isophthalic acid and 13.35g of sebacic acid, mixed dihydric alcohol consisting of 236.65g of glycerin monostearate, 44.61g of butanediol, 26.26g of diethylene glycol and 15.36g of ethylene glycol and 0.09g of catalyst into an esterification kettle for reaction, wherein the initial reaction temperature is 165 ℃, gradually raising the temperature to 225 ℃, and finishing the esterification reaction when the water generated by the reaction reaches more than 95% of the theoretical water yield; adding 0.06g of antioxidant, controlling the reaction temperature to be 235-250 ℃ and the vacuum to be 90-180 Pa, performing polycondensation reaction, and finishing the polycondensation reaction after 1.5-2 h; and introducing nitrogen into the reaction kettle to relieve vacuum, and discharging while the reaction kettle is hot to obtain the low-surface-energy copolyester hot melt adhesive A1.
Example 2
Adding mixed dibasic acid consisting of 127.92g of terephthalic acid, 47.51g of isophthalic acid and 8.9g of sebacic acid, mixed dihydric alcohol consisting of 295.81g of glycerin monostearate, 35.69g of butanediol, 22.76g of diethylene glycol and 13.31g of ethylene glycol and 0.09g of catalyst into an esterification kettle for reaction, wherein the initial reaction temperature is 165 ℃, gradually raising the temperature to 225 ℃, and finishing the esterification reaction when the water generated by the reaction reaches more than 95% of the theoretical water yield; adding 0.06g of antioxidant, controlling the reaction temperature to be 235-250 ℃ and the vacuum to be 90-180 Pa, performing polycondensation reaction, and finishing the polycondensation reaction after 1.5-2 h; and introducing nitrogen into the reaction kettle to relieve vacuum, and discharging while the reaction kettle is hot to obtain the low-surface-energy copolyester hot melt adhesive A2.
Example 3
Adding mixed dibasic acid consisting of 146.19g of terephthalic acid, 32.89g of isophthalic acid and 4.45g of sebacic acid, mixed dihydric alcohol consisting of 354.97g of glycerin monostearate, 26.77g of butanediol, 21.01g of diethylene glycol and 10.24g of ethylene glycol, and 0.09g of catalyst into an esterification kettle for reaction, wherein the initial reaction temperature is 165 ℃, gradually raising the temperature to 225 ℃, and finishing the esterification reaction when the water generated by the reaction reaches more than 95% of the theoretical water yield; adding 0.06g of antioxidant, controlling the reaction temperature to be 235-250 ℃ and the vacuum to be 90-180 Pa, performing polycondensation reaction, and finishing the polycondensation reaction after 1.5-2 h; and introducing nitrogen into the reaction kettle to relieve vacuum, and discharging while the reaction kettle is hot to obtain the low-surface-energy copolyester hot melt adhesive A3.
Example 4
Adding mixed dibasic acid consisting of 127.92g of terephthalic acid, 51.17g of isophthalic acid and 4.45g of sebacic acid, mixed dihydric alcohol consisting of 295.81g of glycerin monostearate, 41.64g of butanediol, 21.01g of diethylene glycol and 10.24g of ethylene glycol and 0.09g of catalyst into an esterification kettle for reaction, wherein the initial reaction temperature is 165 ℃, gradually raising the temperature to 225 ℃, and finishing the esterification reaction when the water generated by the reaction reaches more than 95% of the theoretical water yield; adding 0.06g of antioxidant, controlling the reaction temperature to be 235-250 ℃ and the vacuum to be 90-180 Pa, performing polycondensation reaction, and finishing the polycondensation reaction after 1.5-2 h; and introducing nitrogen into the reaction kettle to relieve vacuum, and discharging while the reaction kettle is hot to obtain the low-surface-energy copolyester hot melt adhesive A4.
Example 5
Adding mixed dibasic acid consisting of 127.92g of terephthalic acid, 43.86g of isophthalic acid and 13.35g of sebacic acid, mixed dihydric alcohol consisting of 295.81g of glycerin monostearate, 29.74g of butanediol, 26.26g of diethylene glycol and 15.36g of ethylene glycol and 0.09g of catalyst into an esterification kettle for reaction, wherein the initial reaction temperature is 165 ℃, gradually raising the temperature to 225 ℃, and finishing the esterification reaction when the water generated by the reaction reaches more than 95% of the theoretical water yield; adding 0.06g of antioxidant, controlling the reaction temperature to be 235-250 ℃ and the vacuum to be 90-180 Pa, performing polycondensation reaction, and finishing the polycondensation reaction after 1.5-2 h; and introducing nitrogen into the reaction kettle to relieve vacuum, and discharging while the reaction kettle is hot to obtain the low-surface-energy copolyester hot melt adhesive A5.
Performance testing
The product A1-A5 obtained in each embodiment and three commercially available copolyester hot melt adhesives with the conventional melting point of 120-130 ℃ are subjected to performance test comparison. Wherein the melting point test is referred to GB/T19466-2004; the peel strength test is referred to GB 11402-; the contact angle test is referred to GB/T30693-; the surface energy calculation method refers to a van Os-Chaudhury-Good method.
The specific results are shown in table 1 below:
table 1: and (5) comparing the performance test with a table.
From the above table 1, it is apparent that the low surface energy polyester hot melt adhesive prepared by the present invention has a suitable melting point, has a suitable pressing temperature, and is suitable for the existing process operation; compared with a comparative example, the copolyester hot melt adhesive prepared by the invention has better peel strength to conventional polar fabrics such as polyester cotton and the like, and the water washing resistance is also improved; particularly, the adhesive has better peel strength to the super-hydrophobic fabric and the non-polar material PP; from the test of water contact angle, it can be seen that the copolyester hot melt adhesive prepared by the invention is hydrophobic; the further calculation of the surface energy data also shows that the polyester hot melt adhesive prepared by the invention has lower surface energy and can be effectively and widely applied to the bonding field of low-surface-energy materials.
Claims (5)
1. The low-surface-energy copolyester hot melt adhesive comprises main materials and auxiliary materials, and is characterized in that: the main material comprises dibasic acid and dihydric alcohol, the dibasic acid is formed by mixing terephthalic acid, isophthalic acid and sebacic acid according to a specific proportion, and the dihydric alcohol is formed by mixing glyceryl monostearate, butanediol, diethylene glycol and ethylene glycol according to a specific proportion; the main materials are prepared from the following components in percentage by weight:
the dibasic acid: the molar ratio of the dihydric alcohol is 1: 1.5;
among the dibasic acids, terephthalic acid: isophthalic acid: the mole ratio of sebacic acid is 1: 0.23-0.57: 0.03 to 0.1;
among the dihydric alcohols, glyceryl monostearate: butanediol: diethylene glycol: the molar ratio of the ethylene glycol is as follows: 1: 0.3-0.75: 0.2-0.38: 0.17 to 0.38;
the auxiliary material comprises a catalyst and an antioxidant, and the addition amount of the catalyst is 0.05 percent of the total mass of the dibasic acid; the addition amount of the antioxidant is 0.03 percent of the total mass of the dibasic acid.
2. The low surface energy copolyester hot melt adhesive of claim 1, wherein: the catalyst is tetrabutyl titanate; the antioxidant is 1010 in grade.
3. A preparation method of a low surface energy copolyester hot melt adhesive is characterized by comprising the following steps:
(1) adding dibasic acid consisting of a mixture of terephthalic acid, isophthalic acid and sebacic acid, dihydric alcohol consisting of a mixture of glyceryl monostearate, butanediol, diethylene glycol and ethylene glycol, and a catalyst into a reaction kettle according to a preset proportion, wherein the reaction temperature is 165-225 ℃, and the esterification reaction is finished when the amount of water produced by the reaction reaches 9% or more of the theoretical water yield;
(2) adding a predetermined amount of antioxidant into the product obtained in the step (1), carrying out reduced pressure polycondensation reaction at 235-250 ℃ under the condition of 90-180 Pa, and finishing the polycondensation reaction after 1.5-2 h;
(3) introducing nitrogen, removing vacuum, and discharging when the product is hot;
in the step (1), the ratio of dibasic acid: the molar ratio of the dihydric alcohol is 1: 1.5;
among the dibasic acids, terephthalic acid: isophthalic acid: the mole ratio of sebacic acid is 1: 0.23-0.57: 0.03 to 0.1;
among the dihydric alcohols, glyceryl monostearate: butanediol: diethylene glycol: the molar ratio of the ethylene glycol is as follows: 1: 0.3-0.75: 0.2-0.38: 0.17 to 0.38.
4. The process for preparing a low surface energy copolyester hot melt adhesive as claimed in claim 3, wherein: in the step (1), the catalyst is tetrabutyl titanate, and the addition amount of the tetrabutyl titanate is 0.05% of the total mass of the dibasic acid.
5. The process for preparing a low surface energy copolyester hot melt adhesive as claimed in claim 3, wherein: in the step (2), the antioxidant is 1010 in grade, and the addition amount of the antioxidant is 0.03 percent of the total mass of the dibasic acid.
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| CN202010824324.2A CN114075423A (en) | 2020-08-17 | 2020-08-17 | Low-surface-energy copolyester hot melt adhesive and preparation method thereof |
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| CN202010824324.2A CN114075423A (en) | 2020-08-17 | 2020-08-17 | Low-surface-energy copolyester hot melt adhesive and preparation method thereof |
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-
2020
- 2020-08-17 CN CN202010824324.2A patent/CN114075423A/en active Pending
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| CN104974337A (en) * | 2014-04-01 | 2015-10-14 | 中国科学院理化技术研究所 | Degradable branched polyester and preparation method thereof |
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| CN107652420A (en) * | 2017-09-22 | 2018-02-02 | 昆山天洋热熔胶有限公司 | A kind of preparation method of biodegradable copolyester hot melt adhesive |
| CN110818872A (en) * | 2019-11-15 | 2020-02-21 | 南京炫科材料科技有限公司 | Preparation of low-surface-energy waterborne polyurethane and application of low-surface-energy waterborne polyurethane in printing ink |
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| 沈一丁等: "阳离子聚酯施胶剂的制备及应用", 《中国造纸》 * |
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Address after: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Applicant after: Tianyang New Material (Shanghai) Technology Co.,Ltd. Applicant after: Kunshan Tianyang New Material Co.,Ltd. Applicant after: NANTONG TIANYANG NEW MATERIAL CO.,LTD. Address before: 201802 Shanghai City, Jiading District Hui Ping Lu Nanxiang Town, No. 505 Applicant before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Applicant before: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. Applicant before: NANTONG TIANYANG NEW MATERIAL CO.,LTD. |
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Application publication date: 20220222 |