CN114085617A - Low-temperature-resistant high-transmittance optical adhesive and preparation method thereof - Google Patents
Low-temperature-resistant high-transmittance optical adhesive and preparation method thereof Download PDFInfo
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- CN114085617A CN114085617A CN202111628285.XA CN202111628285A CN114085617A CN 114085617 A CN114085617 A CN 114085617A CN 202111628285 A CN202111628285 A CN 202111628285A CN 114085617 A CN114085617 A CN 114085617A
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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
- C09J4/00—Adhesives based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; adhesives, based on monomers of macromolecular compounds of groups C09J183/00 - C09J183/16
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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
- C09J11/04—Non-macromolecular additives inorganic
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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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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Inorganic Chemistry (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention relates to a low-temperature-resistant high-transmittance optical adhesive and a preparation method thereof, in particular to an optical adhesive which is characterized by comprising the following components in parts by weight: a compound of formula (I): 45-70 parts of a solvent; filling: 1-10 parts; active diluent: 25-45 parts; light curing agent: 0.5-10 parts; antioxidant: 0.5-10 parts. The adhesive has higher light transmittance, low refractive index and good low-temperature impact resistance.
Description
Technical Field
The invention belongs to the technical field of chemical industry, and particularly relates to a low-temperature-resistant high-light-transmittance optical adhesive and a preparation method thereof.
Background
The adhesive is a substance that bonds adherends together by adhesion. The material can be organic or inorganic, natural or synthetic, and can be solidified to have enough strength. The optical adhesive is a special adhesive, and is characterized by colorless or light-colored transparent, light transmittance of over 90 percent in a specified light wave band, good bonding strength, capability of being cured at room temperature or intermediate temperature, small curing shrinkage and the like.
The optical adhesive is widely applied in the electronic industry, and the types of OCA adhesive films, LOCA and the like are common in the market at present. In the aspects of gap filling property and irregular surface filling, the OCA adhesive tape can only be used for filling gaps of not less than 0.1 mu m generally, and for the adhesion of rough surfaces with curved surfaces, complex surfaces, higher printing ink thickness or uneven surfaces and the like, the OCA adhesive tape can not completely meet the use requirements, and sometimes the problems of bubble residue, size insensitivity and the like exist. In addition, the quality of the cemented binding surface is often unstable due to the complex processes of rolling, vacuum bonding, defoaming and the like adopted in the production process of the OCA tape, and the defects of low light transmittance, large refractive index, easy yellowing and the like exist. The liquid optical adhesive (LOCA) has good bonding strength and appropriate soft ductility, and is suitable for bonding between glass and glass, between glass and a flexible film, between glass and other electronic devices, and the like, and is gradually replacing the traditional OCA tape gluing method. However, the existing liquid optical cement also has some disadvantages: if the low temperature resistance is low, the light transmission is poor, and the requirements of products cannot be met.
Disclosure of Invention
The invention aims to solve the defects in the prior art and provides a low-temperature-resistant high-light-transmittance optical adhesive and a preparation method thereof.
In order to achieve the purpose of the invention, the invention provides a low-temperature-resistant high-light-transmittance optical adhesive.
The invention provides an optical adhesive, which comprises the following components in parts by weight:
a compound of formula (I): 45-70 parts of (A) to (B),
filling: 1-10 parts;
active diluent: 25-45 parts;
light curing agent: 0.5-10 parts;
antioxidant: 0.5-10 parts.
In some preferred embodiments, the filler of the present invention is selected from one or two of quartz powder, fumed silica and titanium dioxide.
In some preferred embodiments, the reactive diluent of the present invention is selected from one or both of 6-hexanediol diacrylate and tripropylene glycol diacrylate.
In some preferred embodiments, the light curing agent of the present invention is selected from one or a mixture of two or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexyl phenyl ketone and benzophenone.
In some preferred embodiments, the antioxidant of the present invention is selected from one or more of pentaerythritol tetraphenylpropionate, distearyl pentaerythritol phosphite and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine.
In some preferred embodiments, the invention provides a low-temperature-resistant high-transmittance optical adhesive, which consists of the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts.
In some preferred embodiments, the invention provides a low-temperature-resistant high-transmittance optical adhesive, which consists of the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts;
wherein the weight ratio of the compound shown in the formula (I) to the filler is 5.5-65: 1.
in some preferred embodiments, the invention provides a low-temperature-resistant high-transmittance optical adhesive, which consists of the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts;
wherein the weight ratio of the compound shown in the formula (I) to the filler is 12: 1.
in some preferred embodiments, the invention provides a low-temperature-resistant high-transmittance optical adhesive, which consists of the following components in parts by weight:
a compound of formula (I): 60 parts of (a) to (b),
titanium dioxide: 5 parts of a mixture;
propylene glycol triacrylate: 34 parts of (a);
benzophenone: 0.5 part; and
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 0.5 part;
wherein the weight ratio of the compound shown in the formula (I) to the filler is 12: 1.
the invention also provides a preparation method of the low-temperature-resistant high-transmittance optical adhesive, which comprises the following steps:
1) respectively weighing the compound shown in the formula (I), the filler and the reactive diluent according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 0.5 to 3 hours at room temperature;
2) respectively weighing the light curing agent and the antioxidant according to the weight percentage, and stirring for 1.5-5 hours until the mixture is uniformly mixed;
3) carrying out vacuum defoaming on the mixture prepared in the step 2);
4) filtering the mixture prepared in the step 3) to obtain a finished product.
Compared with the prior art, the invention has the beneficial effects that:
the optical adhesive disclosed by the invention solves the problems of low-temperature resistance and poor light transmittance of a common optical adhesive by designing and synthesizing the compound shown in the formula (I) with a novel structure, and the compound containing the compound shown in the formula (I) disclosed by the invention is low-temperature resistant and high in light transmittance, so that the structural stability is ensured, and the optical adhesive is widely applied to various fields such as electronics, buildings, chemical building materials and the like.
Detailed Description
The following representative examples are intended to better illustrate the present invention and are not intended to limit the scope of the present invention. The materials used in the following examples are all commercially available unless otherwise specified.
Preparation of the Compounds of formula (I)
Oxalyl chloride (18.8 g) was added dropwise to a solution of 2- (aminomethyl) propane-1, 3-diamine (11.9 g) and methylene chloride (200 mL) under nitrogen at 0 ℃ and N, N-dimethylformamide (200 mL) was added thereto, and the mixture was warmed to room temperature and reacted for 1 hour. The reaction mixture was concentrated to dryness, methylene chloride (1500 mL) was added, and a solution of (E) -6-hydroxyhexane-4-enamine (38.7 g), triethylamine (140 mL) and methylene chloride (1500 mL) was added dropwise at 0 ℃ to complete the reaction at room temperature for 1 hour. The reaction mixture was poured into ice water, extracted with dichloromethane (1500 mL × 2), the combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a crude product.
Oxalyl chloride (14.8 g) was added dropwise to a solution of (E) -6-amino-6-oxohexane-4-enoic acid (38.7 g) and methylene chloride (200 mL) under nitrogen protection at 0 ℃ and N, N-dimethylformamide (200 mL) was added thereto, and the mixture was allowed to warm to room temperature for 1 hour. After the reaction mixture was concentrated to dryness, methylene chloride (1500 mL) was added, and a solution of the compound obtained in the above step, triethylamine (120 mL) and methylene chloride (1500 mL) was added dropwise at 0 ℃ to complete the reaction at room temperature for 1 hour. The reaction mixture was poured into ice water, extracted with dichloromethane (1500 mL × 2), the combined organic layers were washed with saturated brine, dried over anhydrous sodium sulfate and concentrated to give a crude product.
Oxalyl chloride (14.8 g) was added dropwise to a solution of the compound obtained in the above step and dichloromethane (200 mL) under nitrogen protection at 0 ℃, and N, N-dimethylformamide (200 mL) was added thereto, and the mixture was warmed to room temperature to react for 1 hour. The reaction mixture was concentrated to dryness, methylene chloride (1500 mL) was added, and a solution of 3-phenylpropan-1-amino group (38.7 g), triethylamine (100 mL) and methylene chloride (1500 mL) was added dropwise at 0 ℃ to complete the reaction at room temperature for 1 hour. Pouring the reaction solution into ice water, extracting with dichloromethane (1500 mL × 2), combining organic layers, washing with saturated saline solution, drying with anhydrous sodium sulfate, collecting the organic layer, and concentrating to dryness to obtain the compound shown in the formula (I). MS m/z (ESI): 1166.5 [ M + H]+。
Example 1
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
preparation examples prepared compounds of formula (I): 60 parts;
titanium dioxide: 5 parts of a mixture;
propylene glycol triacrylate: 34 parts of (a);
benzophenone: 0.5 part; and
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 0.5 part;
respectively weighing the compound shown in the formula (I) prepared in the preparation example, titanium dioxide and tripropylene glycol diacrylate according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 2 hours at room temperature; respectively weighing benzophenone and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine according to the weight percentage, and stirring for 1.5 hours until the mixture is uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Example 2
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
preparation examples prepared compounds of formula (I): 60 parts;
fumed silica: 5 parts of a mixture;
propylene glycol triacrylate: 34 parts of (a);
benzophenone: 0.5 part;
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 0.5 part.
Respectively weighing the compound shown in the formula (I) prepared in the preparation example, fumed silica and tripropylene glycol diacrylate according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 2 hours at room temperature; respectively weighing benzophenone and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine according to the weight percentage, and stirring for 1 hour until the mixture is uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Example 3
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
preparation examples prepared compounds of formula (I): 60 parts;
titanium dioxide: 5 parts of a mixture;
6-hexanediol diacrylate: 32 parts of (1);
benzophenone: 1 part;
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 1 part.
Respectively weighing the compound shown in the formula (I) prepared in the preparation example, titanium dioxide and 6-hexanediol diacrylate according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 2 hours at room temperature; respectively weighing benzophenone and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine according to the weight percentage, and stirring for 5 hours until the materials are uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Example 4
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
preparation examples prepared compounds of formula (I): 60 parts;
titanium dioxide: 5 parts of a mixture;
6-hexanediol diacrylate: 32 parts of (1);
2-hydroxy-2-methyl-1-phenyl-1-propanone: 1 part;
pentaerythritol tetraphenylpropionate: 1 part.
Respectively weighing the compound shown in the formula (I) prepared in the preparation example, titanium dioxide and 6-hexanediol diacrylate according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 1 hour at room temperature; respectively weighing 2-hydroxy-2-methyl-1-phenyl-1-acetone and pentaerythritol tetraphenylpropionate according to the weight percentage, and stirring for 2.5 hours until the materials are uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Example 5
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
preparation examples prepared compounds of formula (I): 60 parts;
fumed silica: 5 parts of a mixture;
6-hexanediol diacrylate: 34 parts of (a);
2-hydroxy-2-methyl-1-phenyl-1-propanone: 0.5 part;
distearyl pentaerythritol phosphite: 0.5 part.
Respectively weighing the compound shown in the formula (I) prepared in the preparation example, fumed silica and 6-hexanediol diacrylate according to the weight percentage, adding the mixture into a reaction kettle, and stirring the mixture for 1 hour at room temperature; respectively weighing 2-hydroxy-2-methyl-1-phenyl-1-acetone and distearyl pentaerythritol phosphite according to the weight percentage, and stirring for 2.5 hours until the components are uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Comparative example 1
A low-temperature-resistant high-transmittance optical adhesive comprises the following raw materials in parts by weight:
bisphenol a type epoxy resin: 60 parts;
titanium dioxide: 5 parts of a mixture;
propylene glycol triacrylate: 34 parts of (a);
benzophenone: 0.5 part; and
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 0.5 part;
respectively weighing bisphenol A epoxy resin, titanium dioxide and tripropylene glycol diacrylate according to the above weight percentages, adding into a reaction kettle, and stirring for 2 hours at room temperature; respectively weighing benzophenone and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine according to the weight percentage, and stirring for 2.5 hours until the mixture is uniformly mixed; and (3) defoaming again by using a high-speed centrifugal defoaming machine, wherein the defoaming rate is 2300 and 2800r/min, and the defoaming time is 3-5min, so as to obtain the optical adhesive.
Experimental examples Performance test
1. Light transmittance: the light transmittance of the cured optical adhesive with release liner was measured at a wavelength of 330nm using a spectrophotometer (V-660);
2. refractive index: the Abbe refractometer is used for testing, and the specific method is according to ASTM D-1218;
3. low-temperature impact resistance: carry out bonding laminating with glass apron and sensor, the solidification is back completely, uses cold and hot shock case to test, test condition: 150 ℃ C, 30min X50 cycles. Then, the mixture was allowed to stand at room temperature, and the presence or absence of abnormality in the adhesion was observed.
Table 1 results of performance testing
Compared with the comparative example, the adhesive has higher light transmittance, low refractive index and good low-temperature impact resistance.
Although the present invention has been described in detail above, those skilled in the art will appreciate that various modifications and changes can be made to the present invention without departing from the spirit and scope of the invention. The scope of the invention is not to be limited by the above detailed description but is only limited by the claims.
Claims (10)
1. The low-temperature-resistant high-transmittance optical adhesive is characterized by comprising the following components in parts by weight:
a compound of formula (I): 45-70 parts of (A) to (B),
filling: 1-10 parts;
active diluent: 25-45 parts;
light curing agent: 0.5-10 parts;
antioxidant: 0.5-10 parts.
2. The optical adhesive according to claim 1, wherein the filler is one or two selected from quartz powder, fumed silica, and titanium dioxide.
3. The low temperature resistant high light transmission optical adhesive according to claim 1, wherein the reactive diluent is selected from one or two of 6-hexanediol diacrylate and tripropylene glycol diacrylate.
4. The low temperature resistant high light transmittance optical adhesive according to claim 1, wherein the light curing agent is one or a mixture of two or more selected from 2-hydroxy-2-methyl-1-phenyl-1-propanone, 1-hydroxycyclohexyl phenyl ketone and benzophenone.
5. The low temperature resistant high light transmission optical adhesive according to claim 1, wherein the antioxidant is selected from one or more of pentaerythritol tetraphenylpropionate, distearyl pentaerythritol phosphite and N, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine.
6. The low-temperature-resistant high-transmittance optical adhesive according to claim 1, which is prepared from the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts.
7. The low-temperature-resistant high-transmittance optical adhesive according to claim 1, which is prepared from the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts;
wherein the weight ratio of the compound shown in the formula (I) to the filler is 5.5-65: 1.
8. the low-temperature-resistant high-transmittance optical adhesive according to claim 1, which is prepared from the following components in parts by weight:
a compound of formula (I): 55-65 parts of (by weight),
filling: 1-10 parts;
active diluent: 20-35 parts;
light curing agent: 0.5-6 parts; and
antioxidant: 0.5-5 parts;
wherein the weight ratio of the compound shown in the formula (I) to the filler is 12: 1.
9. the low-temperature-resistant high-transmittance optical adhesive according to claim 1, which is prepared from the following components in parts by weight:
a compound of formula (I): 60 parts of (a) to (b),
titanium dioxide: 5 parts of a mixture;
propylene glycol triacrylate: 30 parts of (1);
benzophenone: 2 parts of (1); and
n, N' -bis [3- (3, 5-di-tert-butyl-4-hydroxyphenyl) propionyl ] hydrazine: 2 parts of (1);
wherein the weight ratio of the compound shown in the formula (I) to the filler is 12: 1.
10. a method for preparing the low temperature resistant high light transmission optical adhesive of claims 1-9, comprising:
1) respectively weighing the compound shown in the formula (I), the filler and the reactive diluent according to the weight percentage of claims 1-9, adding the mixture into a reaction kettle, and stirring the mixture for 0.5-3 hours at room temperature;
2) respectively weighing the light curing agent and the antioxidant according to the weight percentage of claims 1-9, and stirring for 1.5-5 hours until the mixture is uniformly mixed;
3) carrying out vacuum defoaming on the mixture prepared in the step 2);
4) filtering the mixture prepared in the step 3) to obtain a finished product.
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Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
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CN103820038A (en) * | 2014-03-12 | 2014-05-28 | 深圳市中显微电子有限公司 | Optical liquid adhesive with high weather resistance and preparation method thereof |
CN107163903A (en) * | 2017-07-07 | 2017-09-15 | 东莞市德聚胶接技术有限公司 | Optical adhesive and preparation method thereof |
CN109337591A (en) * | 2018-09-17 | 2019-02-15 | 东莞市派乐玛新材料技术开发有限公司 | A kind of low volatility ultraviolet light solidification optical texture glue and preparation method thereof |
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2021
- 2021-12-29 CN CN202111628285.XA patent/CN114085617A/en active Pending
Patent Citations (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
CN103820038A (en) * | 2014-03-12 | 2014-05-28 | 深圳市中显微电子有限公司 | Optical liquid adhesive with high weather resistance and preparation method thereof |
CN107163903A (en) * | 2017-07-07 | 2017-09-15 | 东莞市德聚胶接技术有限公司 | Optical adhesive and preparation method thereof |
CN109337591A (en) * | 2018-09-17 | 2019-02-15 | 东莞市派乐玛新材料技术开发有限公司 | A kind of low volatility ultraviolet light solidification optical texture glue and preparation method thereof |
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Application publication date: 20220225 |