UV viscosity-reducing adhesive and preparation method thereof

Abstract

The invention discloses a UV viscosity-reducing adhesive and a preparation method thereof, and relates to the technical field of adhesives, and the UV viscosity-reducing adhesive is prepared from the following raw materials in parts by weight: 10-15 parts of vinyl fluorosilicone oil, 1-3 parts of 1, 3, 5-triacryloylhexahydro-1, 3, 5-triazine, 1-3 parts of 2-(1-propylene-2-yl) benzo [D] oxazole, 0.5-1 part of 1, 1, 3, 3-tetramethyl-1, 3-divinyl disilazane, 0.5-1 part of 1, 4-diacryloyl-1, 2, 3, 5-tetramethyl-1, 3-divinyl disilazane, 0.5-1 part of 1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3, 5-trimethyl-1, 3 The photosensitive resin is prepared from the following components in parts by weight: 1 to 2 parts of 2, 3, 4-tetrahydro-6, 7-dimethyl quinoxaline, 5 to 8 parts of polyimide acrylate oligomer, 10 to 20 parts of photosensitive monomer, 1 to 3 parts of photoinitiator and 20 to 30 parts of diluent. The UV viscosity-reducing glue has the advantages of good environmental protection property, sufficient high temperature resistance, good bonding strength before UV curing, and no residual glue after UV curing.

Description

Technical Field

[0001] The present invention relates to the technical field of adhesives, and particularly relates to a UV tack-reducing adhesive and a preparation method thereof. Background Art

[0002] The UV tack-reducing adhesive is a new type of adhesive material, which has extremely high adhesion, can ensure that the object to be pasted remains stable, does not fall off, does not have burrs during the processing, and plays a protective role for the unprocessed part. After processing, its adhesion can be instantaneously decreased by ultraviolet radiation, and it can be easily removed from the adhered material without affecting the performance of the processed object. Therefore, it is widely used in the processing and manufacturing processes of products such as semiconductor chips, transistors, integrated circuits, printed circuit boards, and optical microscopes.

[0003] At present, most of the formulations of the UV tack-reducing adhesives on the market are prepared by uniformly stirring and mixing the current products containing hydroxyl group-containing unsaturated acrylate polymers, polyfunctional acrylate oligomers, photoinitiators, and curing agents. However, in this method system, the compatibility is limited and it is easy to have residual glue after crosslinking, and it is more difficult to meet the requirements of high-temperature processes, which is not conducive to the subsequent processing technology. Other existing types of UV tack-reducing adhesives also more or less have technical problems such as unsatisfactory bonding strength before UV curing, more residual glue after UV curing, and insufficient environmental protection performance.

[0004] In order to solve the above problems, the Chinese invention patent with the authorization announcement number of CN105086730B discloses a two-component curing UV tack-reducing adhesive, which has the following two components: (1) Component A: including 35-60 parts of a curing resin, 22-45 parts of a photosensitive monomer, 2-10 parts of a photopolymerization initiator, 2-15 parts of a diluent, and 2-10 parts of an auxiliary agent; (2) Component B is isocyanate and / or polythiol. The two-component curing UV tack-reducing adhesive has the advantages of high initial adhesion after curing into glue at normal temperature, good peeling effect and no residual glue after being reduced in viscosity by UV irradiation. However, its high-temperature resistance needs to be further explored.

[0005] It can be seen that developing a UV tack-reducing adhesive with good environmental protection performance, sufficient high-temperature resistance, good bonding strength before UV curing, and no residual glue after UV curing and its preparation method meets the market demand, has broad market value and application prospects, and has very important significance for promoting the development of the UV tack-reducing adhesive field. Summary of the Invention

[0006] The main purpose of the present invention is to provide a UV tack-reducing adhesive with good environmental protection performance, sufficient high-temperature resistance, good bonding strength before UV curing, and no residual glue after UV curing, and a preparation method thereof.

[0007] To achieve the above object, the present invention provides a UV tackifying adhesive, which is made from the following raw materials in parts by weight: 10-15 parts of vinyl fluorosilicone oil, 1-3 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 1-3 parts of 2-(1-propen-2-yl)benzoxazole [D], 0.5-1 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1-2 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 5-8 parts of polyimide acrylate oligomer, 10-20 parts of photosensitive monomer, 1-3 parts of photoinitiator, and 20-30 parts of diluent.

[0008] Preferably, the vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300, provided by Fuzhou Taipuda New Materials Co., Ltd.

[0009] Preferably, there is no special requirement for the source of the polyimide acrylate oligomer. In one embodiment of the present invention, the polyimide acrylate oligomer is prepared by the method of Example 4 of the Chinese invention patent with the authorization announcement number CN103122068B.

[0010] Preferably, the photosensitive monomer is at least one of dipentaerythritol pentaacrylate, pentaerythritol triacrylate, and trimethylolpropane triacrylate.

[0011] Preferably, the photoinitiator is at least one of photoinitiator TPO, photoinitiator 651, photoinitiator 184, and photoinitiator 907.

[0012] Preferably, the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:(1-2):(0.8-1.2).

[0013] Another object of the present invention is to provide a preparation method of the UV tackifying adhesive, which includes the following steps: After mixing the raw materials evenly by weight, vacuum degassing is carried out for 1-2 hours, and finally, it is stored after standing for defoaming to obtain the UV tackifying adhesive.

[0014] Due to the application of the above technical solution, the present invention has the following beneficial effects: (1) The preparation method of the UV tackifying adhesive disclosed in the present invention only needs to mix the raw materials evenly and then carry out degassing and defoaming, without special equipment, the process is simple, the labor intensity is low, the environmental impact is small, the preparation efficiency and the qualified rate of the finished product are high, it is suitable for continuous large-scale production, and has high popularization and application value.

[0015] (2)The UV pressure-sensitive adhesive disclosed by the present invention is prepared from the following raw materials by weight: 10-15 parts of vinyl fluorosilicone oil, 1-3 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 1-3 parts of 2-(1-propen-2-yl)benzoxazole[D], 0.5-1 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1-2 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 5-8 parts of polyimide acrylate oligomer, 10-20 parts of photosensitive monomer, 1-3 parts of photoinitiator, and 20-30 parts of diluent; through the mutual cooperation and joint action of the raw materials, the prepared UV pressure-sensitive adhesive has good environmental protection performance, sufficient high-temperature resistance performance, good bonding strength before UV curing, and no residual glue after UV curing.

[0016] (3)The UV pressure-sensitive adhesive disclosed by the present invention, through the reasonable selection of the raw material formula, enables the introduction of structures and groups such as fluorosilicone oil, triazine, benzoxazole, silazane, quinoxaline, polyimide, and ester into the pressure-sensitive adhesive. Under the multiple actions of electronic effect, steric effect, and conjugation effect, etc., these structures can effectively improve the bonding strength before UV curing, reduce the peeling strength after UV curing, and thus improve the pressure-sensitive adhesive's pressure-sensitive reduction effect; at the same time, it can also enhance the high-temperature resistance performance of the pressure-sensitive adhesive. Detailed implementation mode

[0017] The following description is used to disclose the present invention so that those skilled in the art can implement the present invention. The preferred embodiments in the following description are only examples, and those skilled in the art can think of other obvious variations. Example 1

[0018] A UV pressure-sensitive adhesive is prepared from the following raw materials by weight: 10 parts of vinyl fluorosilicone oil, 1 part of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 1 part of 2-(1-propen-2-yl)benzoxazole[D], 0.5 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1 part of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 5 parts of polyimide acrylate oligomer, 10 parts of photosensitive monomer, 1 part of photoinitiator, and 20 parts of diluent.

[0019] The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300, provided by Fuzhou Taipuda New Materials Co., Ltd.; the polyimide acrylate oligomer is prepared by the method of Example 4 of the Chinese invention patent with the authorized announcement number CN103122068B; the photosensitive monomer is dipentaerythritol pentaacrylate; the photoinitiator is photoinitiator TPO; the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:1:0.8.

[0020] A preparation method of the UV tackifier comprises the following steps: after mixing all raw materials evenly by weight, performing vacuum defoaming for 1 hour, and finally standing for defoaming and then storing to obtain the UV tackifier. Example 2

[0021] A UV tackifier is made from the following raw materials by weight: 11 parts of vinyl fluorosilicone oil, 1.5 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 1.5 parts of 2-(1-propen-2-yl)benzo[D]oxazole, 0.6 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1.2 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 6 parts of polyimide acrylate oligomer, 13 parts of photosensitive monomer, 1.5 parts of photoinitiator, and 23 parts of diluent.

[0022] The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300 provided by Fuzhou Taipuda New Materials Co., Ltd.; the polyimide acrylate oligomer is made by the method of Example 4 of the Chinese invention patent with the authorized announcement number CN103122068B; the photosensitive monomer is pentaerythritol triacrylate; the photoinitiator is photoinitiator 651; the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:1.3:0.9.

[0023] A preparation method of the UV tackifier comprises the following steps: after mixing all raw materials evenly by weight, performing vacuum defoaming for 1.2 hours, and finally standing for defoaming and then storing to obtain the UV tackifier. Example 3

[0024] A UV tackifier is made from the following raw materials by weight: 13 parts of vinyl fluorosilicone oil, 2 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 2 parts of 2-(1-propen-2-yl)benzo[D]oxazole, 0.75 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1.5 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 6.5 parts of polyimide acrylate oligomer, 15 parts of photosensitive monomer, 2 parts of photoinitiator, and 25 parts of diluent.

[0025] The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300, provided by Fuzhou Taipuda New Materials Co., Ltd.; the polyimide acrylate oligomer is prepared by the method of Example 4 of the Chinese invention patent with the authorized announcement number CN103122068B; the photosensitive monomer is trimethylolpropane triacrylate; the photoinitiator is photoinitiator 184; the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:1.5:1.

[0026] A preparation method of the UV tackifying adhesive includes the following steps: After mixing each raw material evenly by weight, vacuum degassing is carried out for 1.5 hours, and finally, it is stored after standing for defoaming to obtain the UV tackifying adhesive. Example 4

[0027] A UV tackifying adhesive is made from the following raw materials by weight: 14 parts of vinyl fluorosilicone oil, 2.5 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 2.5 parts of 2-(1-propen-2-yl)benzoxazole, 0.9 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1.8 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 7.5 parts of polyimide acrylate oligomer, 18 parts of photosensitive monomer, 2.5 parts of photoinitiator, and 28 parts of diluent.

[0028] The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300, provided by Fuzhou Taipuda New Materials Co., Ltd.; the polyimide acrylate oligomer is prepared by the method of Example 4 of the Chinese invention patent with the authorized announcement number CN103122068B; the photosensitive monomer is a mixture of dipentaerythritol pentaacrylate, pentaerythritol triacrylate, and trimethylolpropane triacrylate in a mass ratio of 1:2:3; the photoinitiator is a mixture of photoinitiator TPO, photoinitiator 651, photoinitiator 184, and photoinitiator 907 in a mass ratio of 1:1:2:1; the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:1.8:1.1.

[0029] A preparation method of the UV tackifying adhesive includes the following steps: After mixing each raw material evenly by weight, vacuum degassing is carried out for 1.8 hours, and finally, it is stored after standing for defoaming to obtain the UV tackifying adhesive. Example 5

[0030] A UV pressure-sensitive adhesive release agent is made from the following raw materials in parts by weight: 15 parts of vinyl fluorosilicone oil, 3 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 3 parts of 2-(1-propen-2-yl)benzoxazole, 1 part of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 2 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 8 parts of polyimide acrylate oligomer, 20 parts of photosensitive monomer, 3 parts of photoinitiator, and 30 parts of diluent.

[0031] The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300 provided by Fuzhou Taipuda New Materials Co., Ltd.; the polyimide acrylate oligomer is prepared by the method of Example 4 of the Chinese invention patent with the authorized announcement number CN103122068B; the photosensitive monomer is dipentaerythritol pentaacrylate; the photoinitiator is photoinitiator 907; the diluent is a mixture of methyl methacrylate, butyl methacrylate, and hydroxypropyl methacrylate in a mass ratio of 1:2:1.2.

[0032] A preparation method of the UV pressure-sensitive adhesive release agent includes the following steps: After mixing the raw materials evenly by weight, vacuum defoaming is carried out for 2 hours, and finally, it is stored after standing for defoaming to obtain the UV pressure-sensitive adhesive release agent.

[0033] Comparative Example 1 A UV pressure-sensitive adhesive release agent and its preparation method are basically the same as those in Example 1, except that an equal amount of vinyl fluorosilicone oil is used to replace the polyimide acrylate oligomer; and 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline is not added.

[0034] Comparative Example 2 A UV pressure-sensitive adhesive release agent and its preparation method are basically the same as those in Example 1, except that an equal amount of polyimide acrylate oligomer is used to replace the vinyl fluorosilicone oil; and 2-(1-propen-2-yl)benzoxazole is not added.

[0035] To further illustrate the beneficial technical effects of the UV pressure-sensitive adhesive release agent involved in each embodiment of the present invention, relevant performance tests are carried out on the UV pressure-sensitive adhesive release agents involved in Examples 1-5 and Comparative Examples 1-2. The test results are shown in Table 1, and the test method is as follows: The UV pressure-sensitive adhesive release agents prepared in the above examples and comparative examples are respectively coated on a PO substrate with a thickness of 150 μm, and the coating amount is 40 g / cm 2 , baked at 80°C for 4 min to form a uniform coating with a thickness of 10 μm to obtain a tape, and then tested according to the following method, (1) Peel strength before UV irradiation: The UV irradiation conditions are a UV irradiation intensity of 323 mJ / cm 2, the time is 5 seconds, and the 180° peel strength test with the stainless steel plate is carried out by the method of GB / T 2792-2014; the test result is accurate to 0.1 N / cm; (2) Peel strength after UV irradiation: The UV irradiation condition is that the UV irradiation intensity is 323 mJ / cm 2 , the time is 5 seconds, and the 180° peel strength test with the stainless steel plate is carried out by the method of GB / T 2792-2014; the test result is accurate to 0.0001 N / cm; (3) Residual glue after peeling: After the tape is peeled off, visually observe whether there is residual glue on the chip surface; (4) High temperature resistance: Observe the use situation of the tape at 130 °C. If the fixing property is good and there is no displacement, it is marked as "qualified", otherwise it is marked as "unqualified".

[0036] As can be seen from Table 1, the UV tackifying adhesive disclosed in the embodiments of the present invention has better adhesive strength before UV curing, more excellent UV tackifying performance and high temperature resistance than the products of the comparative examples; the combined use of vinyl fluorosilicone oil, polyimide acrylate oligomer, 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, and 2-(1-propen-2-yl)benzo[D]oxazole is beneficial to improving the above performances.

[0037] Table 1 Project Peeling strength before UV irradiation Peeling strength after UV irradiation Residual glue property after peeling High temperature resistance Unit N / cm N / cm — — Example 1 10.3 0.0084 No residual glue Qualified Example 2 10.9 0.0075 No residual glue Qualified Example 3 11.3 0.0060 No residual glue Qualified Example 4 11.8 0.0056 No residual glue Qualified Example 5 12.2 0.0048 No residual glue Qualified Comparative example 1 8.7 0.0369 Residual glue Unqualified Comparative example 2 9.3 0.0305 Residual glue Unqualified The above shows and describes the basic principles, main features and advantages of the present invention. Those skilled in the art should understand that the present invention is not limited by the above embodiments. What is described in the above embodiments and the specification is only the principle of the present invention. Without departing from the spirit and scope of the present invention, the present invention will have various changes and improvements, and these changes and improvements all fall within the scope of the present invention claimed. The scope of protection claimed by the present invention is defined by the appended claims and their equivalents.

Claims

1. A UV viscosity-reducing adhesive, characterized in that: The invention comprises the following raw materials in parts by weight: 10-15 parts of vinyl fluorosilicone oil, 1-3 parts of 1,3,5-triacryloyl hexahydro-1,3,5-triazine, 1-3 parts of 2-(1-propylene-2-yl)benzo[D]oxazole, 0.5-1 parts of 1,1,3,3-tetramethyl-1,3-divinyldisilazane, 1-2 parts of 1,4-diacryloyl-1,2,3,4-tetrahydro-6,7-dimethylquinoxaline, 5-8 parts of polyimide acrylate oligomer, 10-20 parts of photosensitive monomer, 1-3 parts of photoinitiator and 20-30 parts of diluent.

2. The UV viscosity reducing adhesive according to claim 1, characterized in that: The vinyl fluorosilicone oil is vinyl fluorosilicone oil TPD-FS8019-300.

3. The UV viscosity reducing adhesive according to claim 1, characterized in that: The photosensitive monomer is at least one of dipentaerythritol pentaacrylate, pentaerythritol triacrylate and trimethylolpropane triacrylate.

4. The UV viscosity reducing adhesive according to claim 1, characterized in that: The photoinitiator is at least one of photoinitiator TPO, photoinitiator 651, photoinitiator 184, and photoinitiator 907.

5. The UV viscosity reducing adhesive according to claim 1, characterized in that: The diluent is a mixture of methyl methacrylate, butyl methacrylate and hydroxypropyl methacrylate in a mass ratio of 1:(1-2):(0.8-1.2).

6. A method for preparing the UV viscosity-reducing adhesive according to any one of claims 1 to 5, characterized in that: The method comprises the following steps: mixing the raw materials uniformly according to weight, vacuuming and degassing for 1-2 hours, and finally standing and degassing before storing to obtain UV viscosity-reducing adhesive.