WO2016101895A1 - 一种非结晶性高熔点聚酯热熔胶及其制备方法 - Google Patents

一种非结晶性高熔点聚酯热熔胶及其制备方法 Download PDF

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WO2016101895A1
WO2016101895A1 PCT/CN2015/098468 CN2015098468W WO2016101895A1 WO 2016101895 A1 WO2016101895 A1 WO 2016101895A1 CN 2015098468 W CN2015098468 W CN 2015098468W WO 2016101895 A1 WO2016101895 A1 WO 2016101895A1
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acid
melt adhesive
melting point
ethylene
high melting
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PCT/CN2015/098468
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English (en)
French (fr)
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李哲龙
朱万育
马洪伟
曾作祥
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上海天洋热熔粘接材料股份有限公司
昆山天洋热熔胶有限公司
华东理工大学
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Publication of WO2016101895A1 publication Critical patent/WO2016101895A1/zh

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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
    • 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
    • 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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  • the invention relates to a non-crystalline high melting point polyester hot melt adhesive and a preparation method thereof.
  • polyester hot melt adhesives use aromatic dibasic acids such as terephthalic acid (or dimethyl dibasic acid) and long-chain aliphatic dibasic acids (or dimethyl dibasic acid), binary.
  • the alcohol is obtained by esterification (or transesterification) and polycondensation.
  • Polyester hot melt adhesive products generally have two cases, one case is a lower melting point design, such as the DSC final melting point measured under Differential Scanning Calorimetry (DSC) is lower than 100 ° C, this The hot melt adhesive is not easy to crystallize, and the hand feel is relatively soft. However, it is easy to produce a bond block when producing the material, which causes difficulty in production and low production efficiency.
  • the other case is that the melting point design is higher, such as the final melting point of DSC is higher than At 110 ° C, such hot melt adhesives are easy to crystallize, but the hot melt adhesive is hard and brittle and easy to break.
  • An object of the present invention is to solve the above technical problems and to provide a non-crystalline high melting point polyester hot melt adhesive and a preparation method thereof.
  • Non-crystalline high melting point polyester hot melt adhesive the composition thereof comprises: total dibasic acid composed of terephthalic acid, isophthalic acid and aliphatic dibasic acid, ethylene glycol, diethylene glycol and The total diol, catalyst, stabilizer, antioxidant and ethylene terpolymer composed of 1,5-pentanediol, the ratio of each component is:
  • the molar ratio of the above total dibasic acid: total glycol is 1:1.5-1.7;
  • terephthalic acid isophthalic acid: aliphatic dicarboxylic acid has a molar ratio of 1: 0.10-0.12: 0.125-0.2;
  • the catalyst is selected from the group consisting of tetra-n-butyl titanate, tetraisopropyl titanate, and tetraethyl titanate, and the content thereof is 0.06%-0.2% of the mass of the terephthalic acid;
  • the above stabilizer is trimethyl phosphate or triphenyl phosphite, and the content thereof is 0.01%-0.05% of the mass of terephthalic acid;
  • the content of the above antioxidant is 0.25%-0.3% of the mass of terephthalic acid
  • the above ethylene terpolymer is selected from the group consisting of ethylene-vinyl acetate-carbonyl terpolymer, ethylene-n-butyl acrylate-carbonyl terpolymer or ethylene-n-butyl acrylate-glycidyl terpolymer. , the content of which is 1% to 5% of the quality of terephthalic acid;
  • the above aliphatic dibasic acid is selected from one of 1,6-hexanedioic acid, 1,10-decanedioic acid, and 1,12-dodecanedioic acid.
  • a method for preparing a non-crystalline high melting point polyester hot melt adhesive which comprises the steps of:
  • the ethylene terpolymer is added to the product of the step (2), the vacuum is turned on and stirring is continued for 0.5 h, and the vacuum is discharged after the vacuum is released to obtain the target product.
  • the present invention utilizes a specific ethylene terpolymer to modify the poly-polymer due to the specific formulation ratio.
  • the ester makes the polyester hot melt obtained by the invention have a high melting point and is relatively soft and not easy to break, and is very suitable for the field of textile bonding.
  • a non-crystalline high melting point polyester hot melt adhesive comprising: 166 g (1.0 mol) of terephthalic acid, 16.6 g (0.1 mol) of isophthalic acid, and 29.29 g (0.2 mol) of 1,6-hexanedioic acid, Ethylene glycol 89.595g (1.443mol), diethylene glycol 15.3g (0.144mol), 1,5-pentanediol 37.5g (0.36mol), tetra-n-butyl titanate 0.0996g, trimethyl phosphate 0.0166g 0.415 g of an antioxidant, 1.66 g of an ethylene-n-butyl acrylate-carbonyl terpolymer.
  • a method for preparing a non-crystalline high melting point polyester hot melt adhesive the steps are as follows:
  • Example 1 The product obtained by Example 1 is referred to as A1.
  • polyester hot melt adhesive the raw material composition of which is the same as that of the first embodiment except that the ethylene-n-butyl acrylate-carbonyl terpolymer is not contained;
  • the preparation method is also the same as the method in the first embodiment, but since the ethylene terpolymer is not contained, the step (2) is completed, and the vacuum hot discharge is released;
  • a non-crystalline high melting point polyester hot melt adhesive comprising: 166 g (1.0 mol) of terephthalic acid, 19.92 g (0.12 mol) of isophthalic acid, and 25.28 g (0.125 mol) of 1,10-sebacic acid. 93 g (1.5 mol) of ethylene glycol, 39.75 g (0.375 mol) of diethylene glycol, 15.62 g (0.15 mol) of 1,5-pentanediol, 0.332 g of tetraisopropyl titanate, and triphenyl phosphite 0.083 g 0.498 g of an antioxidant and 8.3 g of an ethylene-vinyl acetate-carbonyl terpolymer.
  • a method for preparing a non-crystalline high melting point polyester hot melt adhesive the steps are as follows:
  • polyester hot melt adhesive the raw material composition of which is the same as that of the embodiment 2 except that the ethylene-vinyl acetate-carbonyl terpolymer is not contained;
  • the preparation method is similar to the method in the second embodiment, but since the ethylene-vinyl acetate-carbonyl terpolymer is not contained, the step (2) is completed, and the vacuum heat discharge is released;
  • a non-crystalline high melting point polyester hot melt adhesive comprising: 166 g (1.0 mol) of terephthalic acid, 18.26 g (0.112 mol) of isophthalic acid, and 34.54 g (0.15 mol) of 1,12-dodecanedioic acid. g, ethylene glycol 94.1g (1.516mol), diethylene glycol 32.178g (0.303mol), 1,5-pentanediol 31.6g (0.303mol), tetraethyl titanate 0.166g, trimethyl phosphate 0.0498 g, an antioxidant 0.4648 g, and an ethylene-n-butyl acrylate-glycidyl ester terpolymer 4.98 g.
  • a method for preparing a non-crystalline high melting point polyester hot melt adhesive the steps are as follows:
  • Example 3 The product obtained by Example 3 was designated as A3.
  • polyester hot melt adhesive the raw material composition of which is the same as that of the third embodiment except that the ethylene-n-butyl acrylate-glycidyl ester terpolymer is not included;
  • the preparation method is similar to the method in the third embodiment, but since the ethylene-n-butyl acrylate-glycidyl ester terpolymer is not contained, the step (2) is completed, and the vacuum hot discharge is released;

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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

本发明公开了一种非结晶性高熔点聚酯热熔胶及其制备方法，由于采用特定的配方比例并利用特定的乙烯三元共聚物来改性聚酯，使得通过本发明所制得的聚酯热熔胶的综合性能有所提高，具备较高的熔点且手感相对柔软，非常适用于纺织品粘合领域。

Description

一种非结晶性高熔点聚酯热熔胶及其制备方法 技术领域
本发明涉及一种非结晶性的高熔点聚酯热熔胶及其制备方法。
背景技术
目前已知的聚酯热熔胶大多采用对苯二甲酸等芳香族二元酸(或二元酸二甲酯)和长链脂肪族二元酸(或二元酸二甲酯)、二元醇经酯化(或酯交换)、缩聚后得到。聚酯类热熔胶产品一般有两种情形，一种情形是熔点设计较低，如在差示扫描量热法(Differential Scanning Calorimetry,DSC)下测得的DSC终熔点低于100℃，此类热熔胶不易结晶，手感相对较软，但生产出料时容易发粘结块，给生产带来困难，生产效率较低；另一类情形是熔点设计较高，如DSC终熔点高于110℃，此类热熔胶易结晶，但热熔胶的手感和质地较硬，脆且容易断。
发明内容
本发明的目的在于，解决上述技术问题，提供一种非结晶性高熔点聚酯热熔胶及其制备方法。
本发明所采用的技术方案为：
一种非结晶性高熔点聚酯热熔胶，其成分包括：由对苯二甲酸、间苯二甲酸及脂肪族二元酸组成的总二元酸、由乙二醇、二乙二醇及1,5-戊二醇组成的总二元醇、催化剂、稳定剂、抗氧剂以及乙烯三元共聚物，各成分的配比为：
上述总二元酸：总二元醇的摩尔比为1:1.5-1.7；
上述对苯二甲酸:间苯二甲酸:脂肪族二元羧酸的摩尔比为1: 0.10-0.12:0.125-0.2；
上述乙二醇：二乙二醇:1,5-戊二醇的摩尔比为1:0.1-0.25:0.1-0.25；
上述催化剂选自钛酸四正丁酯、钛酸四异丙酯、钛酸四乙酯中的一种，其含量为对苯二甲酸质量的0.06％-0.2％；
上述稳定剂为磷酸三甲酯或亚磷酸三苯酯，其含量为对苯二甲酸质量的0.01％-0.05％；
上述抗氧剂的含量为对苯二甲酸质量的0.25％-0.3％；
上述乙烯三元共聚物选自乙烯-醋酸乙烯-羰基三元共聚物、乙烯-丙烯酸正丁酯-羰基三元共聚物或乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物中的一种，其含量为对苯二甲酸质量的1％-5％；
上述脂肪族二元酸选自1,6-己二酸、1,10癸二酸、1,12-十二烷二酸中的一种。
一种非结晶性高熔点聚酯热熔胶的制备方法，以上述成分为原料，进行下述步骤：
(1)将对苯二甲酸、间苯二甲酸、脂肪族二元酸、乙二醇、二乙二醇及1,5-戊二醇在催化剂的作用下进行酯化反应，反应温度150-250℃，当水的馏出量为理论的90-95％时，酯化反应结束；
(2)将稳定剂、抗氧剂加入到步骤(1)的产物中，在250-260℃、100-133Pa压力下进行减压缩聚反应，反应时间2-3h，反应结束后引入氮气解除真空；
(3)在氮气保护下，将乙烯三元共聚物加入步骤(2)的产物中，开启真空并继续搅拌0.5h，解除真空后趁热出料，可得目标产物。
本发明的有益效果
本发明由于采用特定的配方比例，利用特定的乙烯三元共聚物来改性聚 酯，使得通过本发明所制得的聚酯热熔胶具备较高的熔点且手感相对柔软不易断裂，非常适用于纺织品粘合领域。
具体实施方式
实施例1
一种非结晶性高熔点聚酯热熔胶，包括：对苯二甲酸166g(1.0mol)、间苯二甲酸16.6g(0.1mol)、1,6-己二酸29.29g(0.2mol)、乙二醇89.595g(1.443mol)、二乙二醇15.3g(0.144mol)、1,5-戊二醇37.5g(0.36mol)、钛酸四正丁酯0.0996g、磷酸三甲酯0.0166g、抗氧剂0.415g、乙烯-丙烯酸正丁酯-羰基三元共聚物1.66g。
一种非结晶性高熔点聚酯热熔胶的制备方法，步骤如下：
(1)将上述对苯二甲酸、间苯二甲酸、1,6-己二酸、乙二醇、二乙二醇及1,5-戊二醇在催化剂钛酸四正丁酯的作用下进行酯化反应，反应温度150-250℃，当水的馏出量为理论的90-95％时，酯化反应结束；
(2)加入稳定剂磷酸三甲酯、抗氧剂，在250-260℃、100-133Pa压力下进行减压缩聚反应，反应时间2-3h，反应结束后引入氮气解除真空；
(3)在氮气保护下，加入乙烯-丙烯酸正丁酯-羰基三元共聚物，开启真空搅拌0.5h，然后解除真空趁热出料。
通过实施例1所制得的产品记为A1。
对比例1
一种聚酯热熔胶，其原料组成除不包含乙烯-丙烯酸正丁酯-羰基三元共聚物外，其余与实施例1相同；
其制备方法亦与实施例1中的方法雷同，但因不含有乙烯三元共聚物，步骤(2)反应完成后即解除真空趁热出料；
根据对比例1所制得的产品记为B1。
实施例2
一种非结晶性高熔点聚酯热熔胶，包括：对苯二甲酸166g(1.0mol)、间苯二甲酸19.92g(0.12mol)、1,10-癸二酸25.28g(0.125mol)、乙二醇93g(1.5mol)、二乙二醇39.75g(0.375mol)、1,5-戊二醇15.62g(0.15mol)、钛酸四异丙酯0.332g、亚磷酸三苯酯0.083g、抗氧剂0.498g、乙烯-醋酸乙烯-羰基三元共聚物8.3g。
一种非结晶性高熔点聚酯热熔胶的制备方法，步骤如下：
(1)将上述对苯二甲酸、间苯二甲酸、1,10-癸二酸、乙二醇、二乙二醇及1,5-戊二醇在催化剂钛酸四异丙酯的作用下进行酯化反应，反应温度150-250℃，当水的馏出量为理论的90-95％时，酯化反应结束；
(2)加入稳定剂亚磷酸三苯酯、抗氧剂，在250-260℃、100-133Pa压力下进行减压缩聚反应，反应时间2-3h，反应结束后引入氮气解除真空；
(3)在氮气保护下，加入乙烯-醋酸乙烯-羰基三元共聚物，开启真空搅拌0.5h，然后解除真空趁热出料。
通过实施例2所制得的产品记为A2。
对比例2
一种聚酯热熔胶，其原料组成除不包含乙烯-醋酸乙烯-羰基三元共聚物外，其余与实施例2相同；
其制备方法亦与实施例2中的方法雷同，但因不含有乙烯-醋酸乙烯-羰基三元共聚物，步骤(2)反应完成后即解除真空趁热出料；
根据对比例2所制得的产品记为B2。
实施例3
一种非结晶性高熔点聚酯热熔胶，包括：对苯二甲酸166g(1.0mol)、间苯二甲酸18.26g(0.112mol)、1,12-十二烷二酸34.54g(0.15mol)g、乙二醇94.1g(1.516mol)、二乙二醇32.178g(0.303mol)、1,5-戊二醇31.6g(0.303mol)、钛酸四乙酯0.166g、磷酸三甲酯0.0498g、抗氧剂0.4648g、乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物4.98g。
一种非结晶性高熔点聚酯热熔胶的制备方法，步骤如下：
(1)将上述对苯二甲酸、间苯二甲酸、1,12-十二烷二酸、乙二醇、二乙二醇及1,5-戊二醇在催化剂钛酸四乙酯的作用下进行酯化反应，反应温度150-250℃，当水的馏出量为理论的90-95％时，酯化反应结束；
(2)加入稳定剂磷酸三甲酯、抗氧剂，在250-260℃、100-133Pa压力下进行减压缩聚反应，反应时间2-3h，反应结束后引入氮气解除真空；
(3)在氮气保护下，加入乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物，开启真空搅拌0.5h，然后解除真空趁热出料。
通过实施例3所制得的产品记为A3。
对比例3
一种聚酯热熔胶，其原料组成除不包含乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物外，其余与实施例3相同；
其制备方法亦与实施例3中的方法雷同，但因不含有乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物，步骤(2)反应完成后即解除真空趁热出料；
根据对比例3所制得的产品记为B3。
产品相关指标测试
根据实施例1-3及对比例1-3所得产品的指标测试，均按照热熔胶领域常规测试方法及标准进行，具体测试结果如下表1所示。
表1：实施例及对比例各产品测试结果
Figure PCTCN2015098468-appb-000001
从上表1中可明显看出，通过本发明提供的特定配方及制备方法，所制得的聚酯热熔胶的综合性能有明显提升，特别是其具备较高的熔点且手感相对柔软，非常适用于浅颜色的服装、沙发等日用品粘合领域。

Claims (5)

  1. 一种非结晶性高熔点聚酯热熔胶，其成分包括由对苯二甲酸、间苯二甲酸及脂肪族二元酸组成的总二元酸、由乙二醇、二乙二醇及1,5-戊二醇组成的总二元醇、稳定剂、催化剂、抗氧剂，其特征在于，其成分还包括乙烯三元共聚物，且各成分的配比为：
    所述总二元酸：所述总二元醇的摩尔比为1:1.5-1.7；
    所述对苯二甲酸:所述间苯二甲酸:所述脂肪族二元羧酸的摩尔比为1:0.10-0.12:0.125-0.2；
    所述乙二醇：所述二乙二醇:所述1,5-戊二醇的摩尔比为1:0.1-0.25:0.1-0.25；
    所述催化剂的含量为所述对苯二甲酸质量的0.06％-0.2％；
    所述稳定剂的含量为所述对苯二甲酸质量的0.01％-0.05％；
    所述抗氧剂的含量为所述对苯二甲酸质量的0.25％-0.3％；
    所述乙烯三元共聚物选自乙烯-醋酸乙烯-羰基三元共聚物、乙烯-丙烯酸正丁酯-羰基三元共聚物或乙烯-丙烯酸正丁酯-缩水甘油酯三元共聚物中的一种，其含量为所述对苯二甲酸质量的1％-5％。
  2. 如权利要求1所述的非结晶性高熔点聚酯热熔胶，其特征在于，所述脂肪族二元酸选自1,6-己二酸、1,10-癸二酸、1,12-十二烷二酸中的一种。
  3. 如权利要求1所述的非结晶性高熔点聚酯热熔胶，其特征在于，所述催化剂选自钛酸四正丁酯、钛酸四异丙酯、钛酸四乙酯中的一种。
  4. 如权利要求1所述的非结晶性高熔点聚酯热熔胶，其特征在于，所述稳定剂为磷酸三甲酯或亚磷酸三苯酯。
  5. 一种非结晶性高熔点聚酯热熔胶的制备方法，其特征在于，以所述权利要求1-4任一项所述的非结晶性高熔点聚酯热熔胶的原料组成为基础，进行下述步骤：
    (1)将对苯二甲酸、间苯二甲酸、脂肪族二元酸、乙二醇、二乙二醇及1,5-戊二醇在催化剂的作用下进行酯化反应，反应温度150-250℃，当水的馏出量为理论的90-95％时，酯化反应结束；
    (2)将稳定剂、抗氧剂加入到步骤(1)的产物中，在250-260℃、100-133Pa压力下进行减压缩聚反应，反应时间2-3h，反应结束后引入氮气解除真空；
    (3)在氮气保护下，将乙烯三元共聚物加入步骤(2)的产物中，开启真空并继续搅拌0.5h，解除真空后趁热出料，可得目标产物。
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