CN107227140B - Polyesteramide hot melt adhesive and preparation method thereof - Google Patents
Polyesteramide hot melt adhesive and preparation method thereof Download PDFInfo
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- CN107227140B CN107227140B CN201710450020.2A CN201710450020A CN107227140B CN 107227140 B CN107227140 B CN 107227140B CN 201710450020 A CN201710450020 A CN 201710450020A CN 107227140 B CN107227140 B CN 107227140B
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- hot melt
- melt adhesive
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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
- C09J177/00—Adhesives based on polyamides obtained by reactions forming a carboxylic amide link in the main chain; Adhesives based on derivatives of such polymers
- C09J177/12—Polyester-amides
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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
- C08G69/00—Macromolecular compounds obtained by reactions forming a carboxylic amide link in the main chain of the macromolecule
- C08G69/44—Polyester-amides
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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
- C09J11/02—Non-macromolecular additives
- C09J11/06—Non-macromolecular additives organic
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/04—Oxygen-containing compounds
- C08K5/09—Carboxylic acids; Metal salts thereof; Anhydrides thereof
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- Organic Chemistry (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Polyamides (AREA)
Abstract
The invention discloses a polyesteramide hot melt adhesive and a preparation method thereof, in particular to a preparation method for preparing the polyesteramide hot melt adhesive by directly polymerizing a main material consisting of dicarboxylic acid, diamine and alcohol amine and matching with auxiliary materials. The invention mainly designs special raw materials and proportion, and particularly creatively introduces the material of aliphatic alcohol amine with specific proportion in the main material composition. Compared with the existing preparation method of the polyesteramide hot melt adhesive with the same performance, the preparation method disclosed by the invention is simpler and more convenient in preparation process, reduces the use variety of raw materials, greatly improves the preparation efficiency and reduces the production cost.
Description
Technical Field
The invention relates to a polyesteramide hot melt adhesive and a preparation method thereof, in particular to a polyesteramide hot melt adhesive which is prepared by directly polymerizing a main material consisting of dicarboxylic acid, diamine and alcohol amine and auxiliary materials, and a preparation method thereof.
Background
The hot melt adhesive is a plastic high-molecular adhesive without solvent, and various hot melt adhesives (such as EVA, polyamide, polyester and the like) are widely applied in different fields. Among them, the polyesteramide hot melt adhesive generally has lower crystallinity and wider melting range, has good weather resistance and washing resistance of the polyesteramide hot melt adhesive, and also has good flexibility, low melting point and good coating performance similar to those of the polyamide hot melt adhesive, and is more and more popular among customers.
At present, the preparation method and the production process of the polyesteramide hot melt adhesive are generally complicated. In the method for preparing polyesteramide provided by CN105646876A, the reaction time for preparing carbene precursor bromine salt is as long as 20-168 h, and the preparation time of the whole product is longer; also, as disclosed in CN104130744A and CN1157457C, the preparation methods related to polyesteramide hot melt adhesives are all that are relatively cumbersome processes of obtaining polyesteramide by polymerizing dibasic acid and diamine in advance and then adding diamine to react; CN101586015A is a polyesteramide hot melt adhesive prepared by adding a catalyst into amide hot melt adhesive and polyester hot melt adhesive finished products under a co-melting state to cause the amide hot melt adhesive and the polyester hot melt adhesive finished products to generate a chain exchange reaction, and the performance of the product is usually unstable due to the reliability of raw material products.
Therefore, how to provide a relatively simple and convenient polyesteramide hot melt adhesive and a preparation method thereof, which are convenient for production and implementation, becomes a problem to be solved.
Disclosure of Invention
The invention aims to solve the technical problems and provide a polyesteramide hot melt adhesive and a preparation method thereof. The polyesteramide hot melt adhesive prepared by the method effectively controls the types of raw materials, reduces the preparation time and improves the preparation efficiency while ensuring the performance of the product.
The technical scheme adopted by the invention is as follows: the raw materials of the polyesteramide hot melt adhesive comprise a main material and an auxiliary material, wherein the main material comprises aliphatic dicarboxylic acid, aliphatic diamine and aliphatic alcohol amine, and the auxiliary material comprises stearic acid and an antioxidant.
In the main material, the aliphatic dicarboxylic acid is selected from dimer acid, adipic acid, sebacic acid, dodecanedioic acid or tetradecanedioic acid; the aliphatic diamine is selected from one of ethylenediamine, hexamethylenediamine, decamethylenediamine or dodecanediamine; the aliphatic alcohol amine is selected from one of ethanolamine, n-propanol amine, isopropanol amine or n-butanol amine; and an aliphatic dicarboxylic acid: aliphatic diamine: the molar ratio of the aliphatic alcohol amine is 100: 60-95: 5-40.
In the auxiliary materials, the addition amount of stearic acid is 0.1-0.3% of the total mass of the main materials; the addition amount of the antioxidant is 0.1-0.7% of the total mass of the main materials.
Meanwhile, the invention provides a preparation method of the polyesteramide hot melt adhesive, which comprises the following preparation steps:
(1) selecting a main material consisting of aliphatic dicarboxylic acid, aliphatic diamine and aliphatic alcohol amine and an auxiliary material consisting of stearic acid and an antioxidant according to the proportion, and adding the main material and the auxiliary material into a reaction container connected with a reflux condensing device;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly raising the temperature to 240 ℃, then keeping the temperature between 230 ℃ and 250 ℃, and reacting for 1 h; then vacuumizing, and when the system pressure is less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃, and reacting for 1.5 h;
(3) and (4) releasing the negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The innovation point of the invention is that special raw materials and proportion are designed, particularly, aliphatic alcohol amine with a specific proportion is creatively introduced into the main material composition, the addition of the specific alcohol amine is too much or too little to meet the requirement, the water washing resistance of the product is affected when the addition of the specific alcohol amine is too little, and the coating performance and the bonding performance of the product are affected when the addition of the specific alcohol amine is too much.
Compared with the prior polyesteramide hot melt adhesive with the same performance and the preparation method thereof, the invention has the advantages that the reaction activity of the raw materials is good enough, no catalyst is needed, the types of the main materials are controlled, and the types of the auxiliary materials are reduced; meanwhile, the preparation method of directly carrying out polycondensation reaction by feeding materials once is adopted, so that the process is simpler and more convenient; the polyester amide hot melt adhesive with excellent comprehensive performance is prepared by the method, the time required in the preparation process can be controlled within 10 hours and is far shorter than the time required by the conventional preparation method at present (generally more than 12 hours), the preparation efficiency of the polyester amide hot melt adhesive is greatly improved, and the production cost is reduced.
Detailed Description
The present invention will be further illustrated by the following examples, but is not limited thereto.
Example 1:
a polyesteramide hot melt adhesive comprises the following raw materials: 476g of dimer acid, 59.2g of hexamethylene diamine, 20.7g of ethanolamine, 1.7g of stearic acid and 3.9g of antioxidant (brand 1010).
The preparation method of the polyesteramide hot melt adhesive comprises the following specific steps:
(1) adding 476g of dimer acid, 59.2g of hexamethylene diamine, 20.7g of ethanolamine, 1.7g of stearic acid and 3.9g of antioxidant (brand 1010) into a 1000ml reaction vessel provided with a reflux condenser tube;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly heating to 240 ℃, and keeping the temperature between 230 ℃ and 250 ℃ for reaction for 1 h; then opening a vacuum pump to start vacuumizing, enabling the pressure of the system to be less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃ and 0, and reacting for 1.5 h;
(3) and stopping vacuumizing to remove negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The product obtained by example 1 is labelled a 1.
Example 2:
a polyesteramide hot melt adhesive comprises the following raw materials: 255.5 g of adipic acid, 286 g of decamethylene diamine, 7.8 g of 2-amino n-butanol, 0.5g of stearic acid and 3.8g of antioxidant (brand number 168).
The preparation method of the polyesteramide hot melt adhesive comprises the following specific steps:
(1) adding 255.5 g of adipic acid, 286 g of decamethylene diamine, 7.8 g of 2-amino n-butanol, 0.5g of stearic acid and 3.8g of antioxidant (brand number 168) into a 1000ml reaction vessel provided with a reflux condenser tube;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly heating to 240 ℃, and keeping the temperature between 230 ℃ and 250 ℃ for reaction for 1 h; then opening a vacuum pump to start vacuumizing, enabling the pressure of the system to be less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃ and 0, and reacting for 1.5 h;
(3) and stopping vacuumizing to remove negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The product obtained by example 2 is labelled a 2.
Example 3:
a polyesteramide hot melt adhesive comprises the following raw materials: 431.3g of dodecyl diacid, 67.5g of ethylenediamine, 56.25 g of n-propanolamine, 0.6g of stearic acid and 0.6g of antioxidant (brand 1098).
The preparation method of the polyesteramide hot melt adhesive comprises the following specific steps:
(1) 431.3g of dodecyl diacid, 67.5g of ethylenediamine, 56.25 g of n-propanolamine, 0.6g of stearic acid and 0.6g of antioxidant (brand 1098) are added into a 1000ml reaction vessel provided with a reflux condenser tube;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly heating to 240 ℃, and keeping the temperature between 230 ℃ and 250 ℃ for reaction for 1 h; then opening a vacuum pump to start vacuumizing, enabling the pressure of the system to be less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃ and 0, and reacting for 1.5 h;
(3) and stopping vacuumizing to remove negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The product obtained by example 3 is labelled A3.
Example 4:
a polyesteramide hot melt adhesive comprises the following raw materials: 258 g of sebacic acid, 285 g of dodecyl diamine, 5.6g of isopropanolamine, 0.5g of stearic acid and 3.8g of antioxidant (brand 1010).
The preparation method of the polyesteramide hot melt adhesive comprises the following specific steps:
(1) adding 258 g of sebacic acid, 285 g of dodecyl diamine, 5.6g of isopropanolamine, 0.5g of stearic acid and 3.8g of antioxidant (brand 1010) into a 1000ml reaction vessel provided with a reflux condenser tube;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly heating to 240 ℃, and keeping the temperature between 230 ℃ and 250 ℃ for reaction for 1 h; then opening a vacuum pump to start vacuumizing, enabling the pressure of the system to be less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃ and 0, and reacting for 1.5 h;
(3) and stopping vacuumizing to remove negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The product obtained by example 4 is labelled A4.
Example 5:
a polyesteramide hot melt adhesive comprises the following raw materials: 354.8 g of tetradecyl diacid, 141.9 g of decanediamine, 33.6g of ethanolamine, 0.5g of stearic acid and 3.7 g of antioxidant (brand 1010).
The preparation method of the polyesteramide hot melt adhesive comprises the following specific steps:
(1) 354.8 g of tetradecyl diacid, 141.9 g of decanediamine, 33.6g of ethanolamine, 0.5g of stearic acid and 3.7 g of antioxidant (brand 1010) are added into a 1000ml reaction vessel provided with a reflux condenser tube;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly heating to 240 ℃, and keeping the temperature between 230 ℃ and 250 ℃ for reaction for 1 h; then opening a vacuum pump to start vacuumizing, enabling the pressure of the system to be less than 300Pa, continuously keeping the temperature between 230 ℃ and 250 ℃ and 0, and reacting for 1.5 h;
(3) and stopping vacuumizing to remove negative pressure, and discharging to obtain the polyesteramide hot melt adhesive.
The product obtained by example 5 is labelled A5.
Performance testing
And (3) performing related performance tests on the products A1-A5 obtained in the embodiments. Among them, melting point test standard references: GB/T19466-2004; fused finger test standard reference: GB/T3682-2000; peel strength test standard reference: GB/T11402-1989; washing performance test standard reference: FZ/T80007.2-2006. The test results are specifically shown in table 1 below.
Table 1: results of property testing of the products obtained in examples
Meanwhile, the inventor analyzes the performance of the common polyesteramide hot melt adhesive on the market at present and can compare the performance with the system of the polyesteramide hot melt adhesive prepared by the invention. The polyester amide hot melt adhesive prepared by the invention has little difference from similar products in melting point and melting finger, and is convenient for construction and application; and has equivalent peel strength, and also meets the application requirements of corresponding fields. Namely, the polyesteramide hot melt adhesive prepared by the invention can ensure the comprehensive performance of the product.
Furthermore, compared with the prior preparation method of the polyesteramide hot melt adhesive with the same performance, the preparation method adopts one-time feeding and directly carries out polycondensation reaction, and the process is simpler and more convenient; the reaction activity of the raw materials is good enough, so that a catalyst is not needed, the types of the main materials are controlled, and the types of the auxiliary materials are reduced; meanwhile, the polyesteramide hot melt adhesive with excellent comprehensive performance is prepared by the method, the time required in the preparation process can be controlled within 10 hours, which is far shorter than the time required by the conventional preparation method at present (generally more than 12 hours), the preparation efficiency of the polyesteramide hot melt adhesive is greatly improved, and the production cost is reduced.
Claims (6)
1. The polyesteramide hot melt adhesive is composed of two parts, namely a main material and an auxiliary material, and is characterized in that: the main material of the polyesteramide hot melt adhesive is composed of aliphatic dicarboxylic acid, aliphatic diamine and aliphatic alcohol amine, wherein the weight ratio of the aliphatic dicarboxylic acid: aliphatic diamine: the molar ratio of the aliphatic alcohol amine is 100: 60-95: 5-40; the auxiliary materials of the polyesteramide hot melt adhesive consist of stearic acid and an antioxidant, wherein the addition amount of the stearic acid is 0.1-0.3% of the total mass of the main materials, and the addition amount of the antioxidant is 0.1-0.7% of the total mass of the main materials.
2. The polyesteramide hot melt adhesive of claim 1, wherein: the aliphatic dicarboxylic acid is selected from dimer acid, adipic acid, sebacic acid, dodecanedioic acid or tetradecanedioic acid.
3. The polyesteramide hot melt adhesive of claim 2, wherein: the aliphatic diamine is selected from one of ethylenediamine, hexamethylenediamine, decamethylenediamine or dodecanediamine.
4. The polyesteramide hot melt adhesive of claim 3, wherein: the aliphatic alcohol amine is selected from one of ethanolamine, n-propanol amine, isopropanol amine or n-butanol amine.
5. The preparation method of the polyesteramide hot melt adhesive is characterized by comprising the following steps:
(1) selecting a main material consisting of aliphatic dicarboxylic acid, aliphatic diamine and aliphatic alcohol amine and an auxiliary material consisting of stearic acid and an antioxidant according to a preset proportion, and adding the main material and the auxiliary material into a reaction vessel connected with a reflux condensing device;
(2) firstly, replacing nitrogen for 2 times, then slowly heating to 120 ℃, and starting stirring; slowly raising the temperature to 240 ℃, then keeping the temperature between 230 ℃ and 250 ℃ and reacting for 1 h; then vacuumizing, and when the system pressure is less than 300Pa, continuously keeping the temperature between 230 and 250 ℃ and reacting for 1.5 h;
(3) releasing the negative pressure, and discharging to obtain the polyesteramide hot melt adhesive;
the total time of the reaction step of the step (2) is less than or equal to 10 hours;
in the main material in the step (1), the aliphatic dicarboxylic acid: aliphatic diamine: the molar ratio of the aliphatic alcohol amine is 100: 60-95: 5-40; in the auxiliary materials, the addition amount of stearic acid is 0.1-0.3% of the total mass of the main materials, and the addition amount of antioxidant is 0.1-0.7% of the total mass of the main materials.
6. The process for preparing a polyesteramide hot melt adhesive according to claim 5, wherein: the aliphatic dicarboxylic acid is selected from dimer acid, adipic acid, sebacic acid, dodecanedioic acid or tetradecanedioic acid; the aliphatic diamine is selected from one of ethylenediamine, hexamethylenediamine, decamethylenediamine or dodecanediamine; the aliphatic alcohol amine is selected from one of ethanolamine, n-propanol amine, isopropanol amine or n-butanol amine.
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| CN109957108B (en) * | 2017-12-25 | 2022-08-19 | 上海凯赛生物技术股份有限公司 | Polyesteramide hot melt adhesive and preparation method thereof |
| CN111196914B (en) * | 2018-11-20 | 2022-02-18 | 上海天洋热熔粘接材料股份有限公司 | Polyesteramide hot melt adhesive and preparation method thereof |
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| CN104231260A (en) * | 2014-08-11 | 2014-12-24 | 安庆昊业树脂材料科技有限公司 | Low-molecular-weight polyamide resin polyhydric alcohol and preparation method thereof |
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| CN103254868B (en) * | 2013-05-17 | 2014-12-10 | 上海凯赛生物技术研发中心有限公司 | Hot melt adhesive |
| CN105238337A (en) * | 2015-11-13 | 2016-01-13 | 上海天洋热熔粘接材料股份有限公司 | High-performance polyamide hot melt adhesive for surface decoration and preparing method thereof |
| CN106494021A (en) * | 2016-09-30 | 2017-03-15 | 临安金奥科技有限公司 | A kind of PET overlay films aluminium sheet and preparation method thereof |
| CN106753189A (en) * | 2016-12-30 | 2017-05-31 | 上海天洋热熔粘接材料股份有限公司 | A kind of preparation method of polyamide hot |
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| CN104231260A (en) * | 2014-08-11 | 2014-12-24 | 安庆昊业树脂材料科技有限公司 | Low-molecular-weight polyamide resin polyhydric alcohol and preparation method thereof |
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Address after: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee after: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee after: Kunshan Tianyang New Material Co.,Ltd. Patentee after: NANTONG TIANYANG NEW MATERIAL CO.,LTD. Address before: 505 Huiping Road, Nanxiang Town, Jiading District, Shanghai, 201802 Patentee before: SHANGHAI TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: KUNSHAN TIANYANG HOT MELT ADHESIVE Co.,Ltd. Patentee before: NANTONG TIANYANG NEW MATERIAL CO.,LTD. |