Preparation method of high-heat-resistance diepoxide

文档序号:501379 发布日期:2021-05-28 浏览:19次 中文

阅读说明:本技术 一种高耐热双环氧化物的制备方法 (Preparation method of high-heat-resistance diepoxide ) 是由 肖尖 吴宏亮 贾泉 韩建伟 于 2021-01-11 设计创作,主要内容包括:本发明公开了一种高耐热双环氧化物的制备方法,在4-甲苯磺酰氯与吡啶的存在下,4,4’-二羟基二环己烷与金属卤化物反应;然后在碱性环境下脱卤素,制备[1,1’-二(环己烷)]-3,3’-二烯;或者在硫脲的存在下,4,4’-二羟基二环己烷与卤代丁二酰亚胺反应;然后在碱性环境下脱卤素,制备[1,1’-二(环己烷)]-3,3’-二烯;然后[1,1’-二(环己烷)]-3,3’-二烯与过氧乙酸反应,制备所述双环氧化物。现有方法中存在能耗高,选择性差等技术缺陷,羟基在强酸性环境下脱水存在异构体,需精馏提纯,产品收率低,基于以上问题,本发明进行了技术创新,先将羟基进行卤代后,在强碱性环境下形成双键,简化后处理步骤,尤其是避免了异构体的存在,能够高效率便捷的制备(3,4,3’,4’-二环氧)联环己烷。(The invention discloses a preparation method of a high heat-resistant diepoxide, which comprises the following steps of reacting 4,4' -dihydroxybicyclohexane with a metal halide in the presence of 4-tosyl chloride and pyridine; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene; or reacting 4,4' -dihydroxybicyclohexane with a halosuccinimide in the presence of thiourea; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene; the [1,1 '-bis (cyclohexane) ] -3,3' -diene is then reacted with peroxyacetic acid to prepare the diepoxide. The method has the technical defects of high energy consumption, poor selectivity and the like, the hydroxyl is dehydrated in a strong acid environment to form isomers, the product needs rectification and purification, the yield is low, and based on the problems, the method is technically innovative, firstly, the hydroxyl is halogenated, and then, double bonds are formed in a strong alkaline environment, so that the post-treatment steps are simplified, particularly, the isomers are avoided, and the (3,4, 3', 4' -diepoxy) bicyclohexane can be efficiently and conveniently prepared.)

1. A preparation method of a high heat-resistant diepoxide is characterized by comprising the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a metal halide in the presence of 4-toluenesulfonyl chloride and pyridine, followed by dehalogenation in an alkaline environment to prepare [1,1' -bis (cyclohexane) ] -3,3' -diene; or;

reacting 4,4' -dihydroxybicyclohexane with a halosuccinimide in the presence of thiourea, followed by dehalogenation in an alkaline environment to produce [1,1' -bis (cyclohexane) ] -3,3' -diene;

(2) the bis-epoxides are prepared by reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid.

2. The process for preparing a highly thermally stable diepoxide according to claim 1, wherein the metal halide is sodium halide; the halogenated succinimide is chlorosuccinimide or bromosuccinimide.

3. The method of claim 1, wherein the alkaline environment is sodium hydroxide or potassium hydroxide.

4. The method for preparing a high heat-resistant diepoxide according to claim 1, wherein the molar ratio of the 4-tosyl chloride, the pyridine, the 4,4' -dihydroxybicyclohexane and the metal halide is (2-4): (3-5): 1: (2-2.5); the molar weight ratio of the thiourea to the 4,4' -dihydroxybicyclohexane to the halogenated succinimide is (0.4-0.5) to 1 to (1-2).

5. The method for preparing a high heat-resistant diepoxide according to claim 1, wherein the molar ratio of [1,1 '-bis (cyclohexane) ] -3,3' -diene to peroxyacetic acid is 1: 3-4; the reaction of [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid is carried out in the presence of sodium carbonate, sodium polyphosphate.

6. The method for preparing a highly heat-resistant diepoxide according to claim 1, wherein the reaction of 4,4' -dihydroxybicyclohexane with the metal halide is carried out at 50 to 70 ℃ for 3 to 5 hours; the reaction of the 4,4' -dihydroxybicyclohexane and the halogenated succinimide is carried out for 5-7 hours at room temperature.

7. The method for preparing a highly heat-resistant diepoxide according to claim 1, wherein the dehalogenation is carried out at 50-70 ℃ for 4-6 hours in an alkaline environment.

8. The method of claim 1, wherein the reaction of the [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid is carried out at 10 ℃ to 15 ℃ for 4 to 6 hours.

9. The preparation method of the high heat-resistant epoxy cured material is characterized by comprising the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a metal halide in the presence of 4-toluenesulfonyl chloride and pyridine; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid to produce (3,4, 3', 4' -diepoxy) bicyclohexane;

(3) mixing (3,4, 3', 4' -diepoxy) bicyclohexane, a curing agent and a curing accelerator, and heating to obtain an epoxy cured product; or mixing 3(3,4, 3', 4' -diepoxy) bicyclohexane and a light curing agent, and then irradiating to obtain an epoxy cured material;

or the preparation method of the high heat-resistant epoxy cured product comprises the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a halosuccinimide in the presence of thiourea; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid to produce (3,4, 3', 4' -diepoxy) bicyclohexane;

(3) mixing (3,4, 3', 4' -diepoxy) bicyclohexane, a curing agent and a curing accelerator, and heating to obtain an epoxy cured product; or mixing 3(3,4, 3', 4' -diepoxy) bicyclohexane, a light curing agent and an auxiliary agent, and then irradiating to obtain an epoxy cured product.

10. The method for producing a highly heat-resistant cured epoxy product according to claim 9, wherein the auxiliary agent is a leveling agent.

Technical Field

The invention belongs to a preparation technology of an epoxy compound, and particularly relates to a method for conveniently preparing high-purity high-heat-resistant liquid epoxy resin.

Background

Currently, as for the preparation of (3,4, 3', 4' -diepoxy) bicyclohexane, the prior art is as follows: the diol is reacted for 26 hours at 145 ℃ under the catalysis of sodium bisulfate to prepare a product [1,1 '-bis (cyclohexane) ] -3,3' -diene, wherein the obtained product contains 12.5 percent of an isomerization product; or concentrated sulfuric acid and 1, 8-diazabicycloundecen-7-ene are used as dehydration catalyst, and the [1,1 '-di (cyclohexane) ] -3,3' -diene is obtained by rectification at the internal temperature of 137-140 ℃ and at 10 Torr. The method has the technical defects of high energy consumption, poor selectivity and the like, the hydroxyl is dehydrated in a strong acid environment to form isomers, rectification and purification are needed, the product yield is low, and based on the problems, the method is technically innovated, avoids the existence of the isomers, simplifies post-treatment steps, and can efficiently and conveniently prepare the (3,4, 3', 4' -diepoxy) bicyclohexane.

Disclosure of Invention

The invention aims to develop a preparation method of a high heat-resistant diepoxide, so that the preparation method is simple, convenient, high-efficiency, high in yield and low in energy consumption.

The invention adopts the following technical scheme:

the high heat-resistant diepoxide is high-purity high heat-resistant liquid epoxy resin, specifically (3,4, 3', 4' -diepoxy) bicyclohexane, and the chemical structural formula is as follows:

the invention discloses a preparation method of the (3,4, 3', 4' -diepoxy) bicyclohexane, which comprises the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a metal halide in the presence of 4-toluenesulfonyl chloride and pyridine; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) (3,4, 3', 4' -diepoxy) bicyclohexane is prepared by reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid.

The invention discloses a preparation method of the (3,4, 3', 4' -diepoxy) bicyclohexane, which comprises the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a halosuccinimide in the presence of thiourea; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) (3,4, 3', 4' -diepoxy) bicyclohexane is prepared by reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid.

The invention discloses application of the (3,4, 3', 4' -diepoxy) bicyclohexane in preparing an epoxy cured product, wherein the cured product can be a thermal cured product or a light cured product. Further, mixing (3,4, 3', 4' -diepoxy) bicyclohexane, a curing agent and a curing accelerator, and heating to obtain an epoxy thermal curing material; 3(3,4, 3', 4' -diepoxy) bicyclohexane, a light curing agent and an auxiliary agent are mixed and then irradiated by light to obtain an epoxy thermal curing material.

The invention discloses a preparation method of a high heat-resistant epoxy condensate, which comprises the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a metal halide in the presence of 4-toluenesulfonyl chloride and pyridine; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid to produce (3,4, 3', 4' -diepoxy) bicyclohexane;

(3) mixing (3,4, 3', 4' -diepoxy) bicyclohexane, a curing agent and a curing accelerator, and heating to obtain an epoxy cured product; or mixing 3(3,4, 3', 4' -diepoxy) bicyclohexane and a light curing agent, and then irradiating to obtain an epoxy cured material;

or the preparation method of the high heat-resistant epoxy cured product comprises the following steps:

(1) reacting 4,4' -dihydroxybicyclohexane with a halosuccinimide in the presence of thiourea; then dehalogenating in alkaline environment to prepare [1,1 '-bis (cyclohexane) ] -3,3' -diene;

(2) reacting [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid to produce (3,4, 3', 4' -diepoxy) bicyclohexane;

(3) mixing (3,4, 3', 4' -diepoxy) bicyclohexane, a curing agent and a curing accelerator, and heating to obtain an epoxy cured product; or (3,4, 3', 4' -diepoxy) bicyclohexane, a light curing agent and an auxiliary agent are mixed and then irradiated with light to obtain an epoxy cured product.

Wherein the auxiliary agent is a leveling agent.

In the invention, the metal halide is sodium halide, and is further sodium chloride or sodium bromide; the halogenated succinimide is chlorosuccinimide or bromosuccinimide.

In the present invention, the alkaline environment is sodium hydroxide or potassium hydroxide.

In the invention, the molar ratio of the 4-tosyl chloride to the pyridine to the 4,4' -dihydroxybicyclohexane to the metal halide is (2-4) to (3-5) to 1 to (2-2.5), and preferably 3: 4: 1: 2.1.

In the invention, the molar weight ratio of the thiourea, the 4,4' -dihydroxybicyclohexane and the halogenated succinimide is (0.4-0.5) to 1 to (1-2), and preferably 0.45 to 1 to 1.5.

In the invention, the molar ratio of the [1,1 '-bis (cyclohexane) ] -3,3' -diene to the peroxyacetic acid is 1: 3-4, preferably 1: 3.6-3.65; preferably, the reaction of the [1,1 '-bis (cyclohexane) ] -3,3' -diene with peroxyacetic acid is carried out in the presence of sodium carbonate, sodium polyphosphate.

In the invention, the reaction of the 4,4' -dihydroxybicyclohexane and the metal halide is carried out for 3-5 hours at 50-70 ℃, preferably for 4 hours at 60 ℃; the reaction of 4,4' -dihydroxybicyclohexane with the halogenated succinimide is carried out at room temperature for 5 to 7 hours, preferably at room temperature for 6 hours.

In the invention, dehalogenation is carried out in an alkaline environment by adding sodium hydroxide aqueous solution or potassium hydroxide aqueous solution at the temperature of less than 10 ℃, and then reacting at 50-70 ℃ for 4-6 hours, preferably 60 ℃ for 5 hours.

In the invention, peracetic acid is added into a mixture of [1,1 '-bis (cyclohexane) ] -3,3' -diene, sodium carbonate and sodium polyphosphate at the temperature of 10-15 ℃, and then the reaction is carried out for 4-6 hours, preferably 5 hours under the condition of heat preservation.

In the invention, after the dehalogenation in the step (1) is finished, standing, separating liquid, washing with water, and removing a solvent by rotary evaporation to obtain [1,1 '-bis (cyclohexane) ] -3,3' -diene; these post treatments are conventional techniques.

In the invention, after the reaction in the step (2) is finished, sequentially carrying out standing liquid separation, water washing, alkali washing with sodium hydroxide solution, water washing and solvent removal by rotary evaporation to obtain (3,4, 3', 4' -diepoxy) bicyclohexane, which is the liquid epoxy resin; these post treatments are conventional techniques. The synthetic route of the invention is as follows:

the invention has the advantages that:

the method for dehalogenating into double bonds in an alkaline environment is utilized to avoid the phenomenon of double bond displacement caused by leaving and dehydrating hydroxyl groups in the prior art, reduce the content of product impurities, simplify the purification difficulty of products, and improve the product quality by simple distillation without rectification.

Drawings

FIG. 1 is a nuclear magnetic hydrogen spectrum of TTA 800;

figure 2 is the sodium addition mass spectrum of TTA 800.

Detailed Description

The raw materials adopted by the invention are all the existing commercial products, the specific operation method and the test method are the conventional methods in the field, and the related stirring, purification and the like are the conventional methods. The method takes 4,4' -dihydroxyl dicyclohexyl as a raw material, and can efficiently, conveniently and rapidly prepare high-purity (3,4, 3', 4' -diepoxy) bicyclohexyl through halogen-substituted hydroxyl reaction, dehalogenation and double-bond epoxidation reaction in a solvent; the invention can obtain the product by simple conventional rotary evaporation without rectification. The synthetic route is as follows:

example one

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane as a solvent, adding 31.64g (0.4mol) of pyridine under stirring, adding 57.21g (0.3mol) of paratoluensulfonyl chloride (TsCl) into the system under 0 ℃, dropwise adding the mixture for 30 minutes, heating to room temperature, adding 21.6g (0.21mol) of NaBr, heating to 60 ℃, stirring for reaction, after 4 hours of reaction, cooling the system to 10 ℃, adding 50mL of 50 wt% NaOH aqueous solution dropwise, heating to 60 ℃, stirring and refluxing for 5 hours, standing for liquid separation, taking 100mL of the upper layer solution, washing for 2 times, removing the solvent by conventional rotary evaporation, collecting 10.37g (0.064mol) of [1,1' -bis (cyclohexane) ] -3,3' -diene, and obtaining the yield of 63.9%.

Example two

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane serving as a solvent, adding 31.64g (0.4mol) of pyridine under stirring, adding 57.21g (0.3mol) of paratoluensulfonyl chloride (TsCl) into the system under 0 ℃, after 30 minutes of dropwise addition, heating to room temperature, adding 12.27g (0.21mol) of NaCl, heating to 60 ℃, stirring for reaction, after 4 hours of reaction, cooling the system to 10 ℃, adding 50mL of 50 wt% NaOH aqueous solution, heating to 60 ℃, stirring and refluxing for 5 hours, standing for liquid separation, taking 100mL of upper solution, washing for 2 times, performing conventional rotary evaporation to remove the solvent, collecting [1,1' -di (cyclohexane) ] -3,3' -diene 9.24g (0.057mol) at 100 ℃ and 120 ℃ (60Pa), and obtaining the molar yield of 57.1%.

EXAMPLE III

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane serving as a solvent, adding pyridine (0.3mol) under stirring, dropwise adding 57.21g of p-toluenesulfonyl chloride (TsCl) (0.3mol) into the system at 0 ℃, heating to room temperature after 30 minutes of dropwise addition, adding 21.6g (0.21mol) of NaBr, heating to 60 ℃, stirring for reaction, cooling the system to 10 ℃ after 4 hours of reaction, dropwise adding 50mL of 50 wt% NaOH aqueous solution, heating to 60 ℃, stirring and refluxing for 5 hours, standing, separating, taking 100mL of upper layer solution, washing for 2 times, carrying out conventional rotary evaporation to remove the solvent, collecting [1,1' -di (cyclohexane) ] -3,3' -diene at 100-120 ℃ (60Pa), and obtaining the molar yield of 56.8%.

The synthetic route is as follows:

example four

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane as a solvent, adding 3.43g (0.045mol) of thiourea and 26.70g (0.15mol) of N-bromosuccinimide (NBS) into the mixture under stirring at room temperature, after reacting for 6h, cooling the system to 10 ℃, dropwise adding 50mL of 50 wt% NaOH aqueous solution, heating to 60 ℃, stirring and refluxing for 5h, standing and separating, taking 100mL of upper solution, washing 2 times with water, removing the solvent by conventional rotary evaporation, collecting 11.67g (0.072mol) of [1,1' -bis (cyclohexane) ] -3,3' -diene at 100-120 ℃ (60Pa), and obtaining the molar yield of 72.1%.

EXAMPLE five

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane as a solvent, adding 3.43g (0.045mol) of thiourea and 20.0g (0.15mol) of N-chlorosuccinimide (NCS) at room temperature under stirring, after reacting for 6h, cooling the system to 10 ℃, dropwise adding 50mL of 50 wt% NaOH aqueous solution, heating to 60 ℃, stirring and refluxing for 5h, standing and separating, taking 100mL of upper solution, washing 2 times with water, removing the solvent by conventional rotary evaporation, collecting 11.35g (0.070mol) of [1,1' -di (cyclohexane) ] -3,3' -diene at 100-120 ℃ (60Pa), and obtaining the molar yield of 70.0%.

EXAMPLE six

Adding 19.8g (0.1mol) of 4,4' -dihydroxybicyclohexane into a 500mL reaction bottle, adding 200mL dichloromethane as a solvent, adding 3.43g (0.045mol) of thiourea and 20.0g (0.15mol) of N-chlorosuccinimide (NCS) at room temperature under stirring, after reacting for 7h, cooling the system to 10 ℃, dropwise adding 50mL of 50 wt% NaOH aqueous solution, heating to 60 ℃, stirring and refluxing for 5h, standing and separating, taking 100mL of upper solution, washing for 2 times, removing the solvent by conventional rotary evaporation, collecting [1,1' -di (cyclohexane) ] -3,3' -diene at 100-120 ℃ (60Pa), and obtaining the molar yield of 69.9%.

The [1,1 '-bis (cyclohexane) ] -3,3' -diene prepared by the method solves the problem of isomerization in the prior art, and the obtained product has no isomerization by-product through conventional GC test; in the prior art, sulfuric acid/DBU, sodium bisulfate and the like are used as dehydrating agents, and the obtained [1,1 '-bis (cyclohexane) ] -3,3' -diene has isomerization products such as:

the synthetic route is as follows:

EXAMPLE seven

Adding 100g (0.62mol) of [1,1 '-bis (cyclohexane) ] -3,3' -diene into a 1000mL reaction bottle, adding 300g of dichloroethane, 42g (0.4mol) of sodium carbonate and 0.5g of sodium polyphosphate (DPN), maintaining the temperature to be 10-15 ℃, dropwise adding 152g (2.24mol) of 23 wt% peroxyacetic acid solution, maintaining the temperature for 5 hours after finishing dropwise adding, standing for liquid separation, washing with 100g of water for 2 times, washing with 100g of 10% NaOH aqueous solution for one time, washing with 100g of water for 2 times, removing the solvent by conventional rotary evaporation, collecting 103.4g (0.53mol) of (3,4, 3', 4' -diepoxy) dicyclohexyl product at 170 ℃ (60Pa) by 140 times, wherein the yield is 85.5%, and the product is abbreviated as TTA 800. FIG. 1 is a nuclear magnetic hydrogen spectrum of (3,4, 3', 4' -diepoxy) bicyclohexane; FIG. 2 is a sodium-added mass spectrum of (3,4, 3', 4' -diepoxy) bicyclohexane.

Example eight

Adding 100g (0.62mol) of [1,1 '-bis (cyclohexane) ] -3,3' -diene into a 1000mL reaction bottle, adding 300g of dichloroethane, 42g (0.4mol) of sodium carbonate and 0.5g of sodium polyphosphate (DPN), maintaining the temperature to be 10-15 ℃, dropwise adding 152g (2.24mol) of 23 wt% peroxyacetic acid solution, maintaining the temperature for 10h after finishing dropwise adding, standing for liquid separation, washing with 100g of water for 2 times, washing with 100g of 10% NaOH aqueous solution for one time, washing with 100g of water for 2 times, removing the solvent by conventional rotary evaporation, collecting 89.3g (0.46mol) of (3,4, 3', 4' -diepoxy) dicyclohexyl product at 170 ℃ (60Pa) by 140 times, and obtaining 74.2% of yield, which is abbreviated as TTA 800.

Example nine

100 parts by weight of TTA800, 130 parts by weight of MHHPA (methyl hexahydrophthalic anhydride) curing agent and 2 parts by weight of AO-4 curing accelerator are taken, and after being mixed conventionally, the mixture is heated for 1 hour at 80 ℃ and then heated for 4 hours at 120 ℃ to obtain a thermal cured material.

The TTA800 was replaced with TTA21P for comparison, and 100 parts by weight of TTA21P, 130 parts by weight of MHHPA (methyl hexahydrophthalic anhydride) curing agent, and 2 parts by weight of AO-4 curing accelerator were mixed conventionally, heated at 80 ℃ for 1 hour, and then heated at 120 ℃ for 4 hours to obtain a heat-cured product.

DSC (20 ℃/min), TMA (10 ℃/min) and DMA (2 ℃/min) are adopted to test the relevant performance, and the results are shown in Table 1.

TABLE 1 TTA800 and TTA21P thermoset test data

Example eight

TTA 21P: sample TTA21P 100 parts, TPO (2,4, 6-trimethylbenzoyl-diphenylphosphine oxide) 1 part, BYK333 (polyether modified polydimethylsiloxane) 0.1 part.

TTA 800: sample TTA 800100 parts, TPO 1 part, BYK 3330.1 part.

Temperature 25 ℃, humidity 50%, substrate: tinplate (common paint institute standard plate), light source: mercury lamps (Runw electromechanical RW-UVAP202-20 gl).

Coating thickness of the wire rod: 15 μm.

Heating treatment: the postbaking time is 30min and the temperature is 80 ℃.

Pencil hardness: the test load was 1500 g.

Flexibility: QTX paint film flexibility tester.

And (3) testing the adhesive force: grade 0-5, and grade 0 is most preferred.

The case of surface drying: judging the surface dryness condition by a finger touch method:

1-oil, not solid;

2-surface oil, bottom layer solidification;

3, sticking the surface, and keeping the fingerprint heavier after touching by hand;

4-basic surface dryness, slight astringent after touching with hands, light fingerprint;

5-complete curing, smooth surface and no fingerprint after hand touch.

The epoxy sample and the light curing agent are mixed according to the parts by weight to obtain the epoxy ultraviolet light curing paint, the test is carried out according to the standard, the result is shown in table 2, the curing speed of TTA800 is higher than TTA21P, and the hardness of TTA800 is higher than TTA 21P.

TABLE 2 TTA800 to TTA21P UV light cured data comparison

Test items TTA800 TTA21P Test standard
Curing speed (energy 80 mJ/cm)2) 5 4 GB/T 1728-1979
Hardness of pencil 5H 3H GB/T 6739-2006
Flexibility 1 1 GB/T 1731-1993
Adhesion force Level 0 Level 0 GB/T 9286-1998

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