CN113930217A - High-refractive-index light-curable organic silicon adhesive and preparation method and application thereof - Google Patents
High-refractive-index light-curable organic silicon adhesive and preparation method and application thereof Download PDFInfo
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- CN113930217A CN113930217A CN202111307053.4A CN202111307053A CN113930217A CN 113930217 A CN113930217 A CN 113930217A CN 202111307053 A CN202111307053 A CN 202111307053A CN 113930217 A CN113930217 A CN 113930217A
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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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
- C09J183/08—Polysiloxanes containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
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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
- C09J183/00—Adhesives based on macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon, with or without sulfur, nitrogen, oxygen, or carbon only; Adhesives based on derivatives of such polymers
- C09J183/04—Polysiloxanes
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2203/00—Applications
- C08L2203/20—Applications use in electrical or conductive gadgets
- C08L2203/206—Applications use in electrical or conductive gadgets use in coating or encapsulating of electronic parts
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- Adhesives Or Adhesive Processes (AREA)
Abstract
The invention discloses a high-refractive-index light-curable organic silicon adhesive which comprises the following components in parts by mass: linear polysiloxane containing sulfydryl and phenyl, linear polysiloxane containing alkenyl and phenyl, fully inert polysiloxane resin and photoinitiator; the invention also provides a preparation method of the high-refractive-index light-curable organic silicon adhesive and application of the high-refractive-index light-curable organic silicon adhesive in attaching of a touch screen. According to the invention, a platinum catalyst is not used, a functional group containing sulfydryl and alkenyl generates crosslinking through a click chemical reaction under illumination, the bad curing phenomenon caused by platinum catalyst poisoning is avoided, and meanwhile, phenyl is introduced into a molecular structure as a high-refractive-index functional group, so that the refractive index of the adhesive is more than 1.5, and the brightness and the definition of initial display are improved.
Description
Technical Field
The invention relates to the field of high polymer materials, in particular to a high-refractive-index light-curable organic silicon adhesive and a preparation method and application thereof.
Background
Due to the development of technologies such as plasma display, liquid crystal display, and OLED display, the application of the touch screen full-lamination display technology in daily life is becoming more and more widespread, such as mobile phones, computers, tablets, and other consumer electronics, and the application of the full-lamination display technology in outdoor display and vehicle-mounted display is more popular among consumers in recent years.
A Liquid Optically Clear Adhesive (LOCA) is located between the cover glass and the liquid crystal panel, and is one of the key components of the display module. It not only plays the role of adhesive in the assembly link, but also can improve the optical definition, identifiability, contrast and the like of display by preventing the light reflection of an external light source. Ultraviolet (UV) cured acrylic LOCA has been used for several years in consumer electronics displays as an optically clear adhesive. However, when the UV light-curable acrylic acid is exposed to severe conditions such as high temperature, high humidity and light, yellowing, peeling, fogging and the like easily occur, which leads to a decrease in definition, contrast, brightness and the like of display, and thus it is not suitable for the industries such as outdoor, vehicle-mounted display and the like. The organosilicon material has a stable Si-O-Si structure, good chemical stability and excellent optical stability, so that the organosilicon-based liquid optical transparent adhesive is an ideal material for replacing the traditional UV light-cured acrylic liquid optical transparent adhesive.
Currently commercialized silicone liquid optically clear adhesives are based on hydrosilylation, and the curing type includes both photo/thermal dual curing and thermal curing. The catalyst used in the photo/thermal dual curing system is mainly a photosensitive platinum compound containing a conjugated diene structure, such as (trimethyl) cyclopentadienylplatinum (IV) (CAS:1271-07-4) and acetylacetonatoplatinum (15170-57-7), etc., and the catalyst used in the thermal curing system is mainly a vinyl complex of chloroplatinic acid, such as Karstedt's catalyst. In the use process of the system, the platinum catalyst is often poisoned and fails due to the contact with substrates such as a polaroid and the like, so that the poor curing condition is caused. And the currently used commercial liquid optical transparent organic silicon adhesive has methyl main chain side group of organic silicon molecule, refractive index of about 1.4, low refractive index compared with the traditional acrylic LOCA (the refractive index is generally more than 1.5), and initial display brightness and definition inferior to that of the acrylic LOCA.
Disclosure of Invention
The invention aims to solve the problems of poor curing and low refractive index of an organic silicon optical transparent adhesive in the prior art, provides a high-refractive-index light-curable organic silicon adhesive, and also provides a preparation method of the high-refractive-index light-curable organic silicon adhesive and application of the high-refractive-index light-curable organic silicon adhesive in attaching of a touch screen.
In order to solve the technical problems, the technical scheme adopted by the invention is as follows: the high-refractive-index light-curable organic silicon adhesive comprises the following components in parts by mass: 3-50 parts of linear polysiloxane containing sulfydryl and phenyl, 10-70 parts of linear polysiloxane containing alkenyl and phenyl, 1-50 parts of fully inert polysiloxane resin and 0.01-5 parts of photoinitiator;
the linear polysiloxane containing sulfydryl and phenyl has the viscosity of 100-100000 mPa.s at 25 ℃, and the refractive index is more than 1.5;
the linear polysiloxane containing alkenyl and phenyl has a viscosity of 100-100000 mPa.s at 25 ℃, and a refractive index > 1.5.
Preferably, the molar ratio of the mercapto group in the linear polysiloxane containing the mercapto group and the phenyl structure to the functional group of the alkenyl group in the linear polysiloxane containing the alkenyl group and the phenyl structure is 0.2: 1-5: 1.
Preferably, the content of mercapto group in the linear polysiloxane containing mercapto group and phenyl group is 0.1 wt% to 5 wt%.
Preferably, the linear polysiloxane containing mercapto and phenyl structures has the structural formula:
wherein n is>0，m≥0，x＞0；R1Is composed of C1～C10Alkyl of (a), said R1Is one of methyl, ethyl, propyl, aryl or mercapto-substituted alkyl; z is CnH2nThe structure of the alkylene, and the Z is one of ethylene, propylene and butylene.
Preferably, the content of the alkenyl double bond in the linear polysiloxane containing alkenyl and phenyl is 0.02 wt% to 5 wt%.
Preferably, the linear polysiloxane containing alkenyl and phenyl groups has the structural formula:
wherein r is>0，s≥0，t＞0；R2Is composed of C1～C10Alkyl of (a), said R2Is one of methyl, ethyl, propyl, aryl or alkyl substituted by alkenyl; r3Is a functional group containing an alkenyl group, said R3Is one of acryloyloxy, acryloyloxypropyl, methacryloyloxypropyl, ethenyl, propenyl, butenyl, pentenyl or hexenyl.
Preferably, the molecular structure of the polysiloxane resin with the all-inert structure is as follows:
(R4 3SiO0.5)a(R5SiO1.5)b(R6 2SiO)c(SiO2)d
the polysiloxane resin with the full inert structure is one or a mixture of MT resin, MDQ resin, MDT resin, MTQ resin and MTDQ resin containing a benzene ring structure.
Preferably, the photoinitiator is one or more of 2-hydroxy-2-methyl-1-phenyl-1-acetone, 2-diethoxyacetophenone, (2,4, 6-trimethylbenzoyl) diphenylphosphoric oxide, phenyl (2,4, 6-trimethylbenzoyl) phosphoric acid ethyl ester, and derivatives of 2-hydroxy-2-methyl-1-propanone-1- (4-C10-13-alkylbenzene).
The invention also provides a preparation method of the high-refractive-index light-curable organic silicon adhesive, which is prepared by respectively preparing linear polysiloxane containing sulfydryl and phenyl, linear polysiloxane containing alkenyl and phenyl, and fully inert polysiloxane resin and uniformly mixing with a photoinitiator.
The invention also provides application of the high-refractive-index light-curable organic silicon adhesive in attaching a touch screen.
The invention has the following beneficial effects: according to the invention, a platinum catalyst is not used, a functional group containing sulfydryl and alkenyl generates crosslinking through a click chemical reaction under illumination, the bad curing phenomenon caused by platinum catalyst poisoning is avoided, and meanwhile, phenyl is introduced into a molecular structure as a high-refractive-index functional group, so that the refractive index of the adhesive is more than 1.5, and the brightness and the definition of initial display are improved.
Detailed Description
To make the objects, technical solutions and advantages of the embodiments of the present invention clearer, the technical solutions of the present invention will be clearly and completely described below with reference to specific embodiments of the present invention, and it is obvious that the described embodiments are some, but not all embodiments of the present invention.
In the following examples, the raw material ratios are by weight.
Example 1
Preparing 45 parts of linear polysiloxane with 3000mPa.s, a refractive index of 1.51 and a theoretical mercapto content of 3.28 wt%; 35 parts of linear polysiloxane with the viscosity of 4000mPa.s, the refractive index of 1.51 and the theoretical content of carbon-carbon double bonds of 3.42 weight percent; 20 parts of phenyl MTQ resin, 0.2 part of photoinitiator ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphonate (TPO-L) and uniformly mixing to prepare the photocuring organic silicon adhesive.
Example 2
40 parts of linear polysiloxane with the viscosity of 5000mPa.s, the refractive index of 1.52 and the theoretical content of sulfydryl of 3.92 weight percent; 40 parts of linear polysiloxane with the viscosity of 4000mPa.s, the refractive index of 1.51 and the theoretical content of carbon-carbon double bonds of 3.42 weight percent; 20 parts of phenyl MTQ resin, 0.2 part of photoinitiator ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphonate (TPO-L) and uniformly mixing to prepare the photocuring organic silicon adhesive.
Example 3
40 parts of linear polysiloxane with 3000mPa.s, refractive index of 1.51 and theoretical mercapto content of 3.28 weight percent; 40 parts of linear polysiloxane with the viscosity of 4000mPa.s, the refractive index of 1.51 and the theoretical content of carbon-carbon double bonds of 2.48 weight percent; 20 parts of phenyl MDT resin, 0.2 part of photoinitiator ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphonate (TPO-L) and uniformly mixing to prepare the photocuring organic silicon adhesive.
Example 4
35 parts of linear polysiloxane with the viscosity of 5000mPa.s, the refractive index of 1.52 and the theoretical content of sulfydryl of 3.92 weight percent; 40 parts of linear polysiloxane with the viscosity of 4000mPa.s, the refractive index of 1.51 and the theoretical content of carbon-carbon double bonds of 2.48 weight percent; 20 parts of phenyl MDT resin, 0.2 part of photoinitiator ethyl phenyl (2,4, 6-trimethylbenzoyl) phosphonate (TPO-L) and uniformly mixing to prepare the photocuring organic silicon adhesive.
Comparative test for photo-curing adhesive
The photo-curing silicone adhesive prepared in examples 1-4 is divided into a test group and a control group, wherein the control group comprises a control group 1 and a control group 2, the control group 1 is a commercial photo-curing silicone LOCA (Waters Lumisil 203) for optical full-lamination, the viscosity of the component A is 3800mPa.s, the viscosity of the component B is 1000mPa.s, and the mixing ratio is 10: 1; control 2 was a commercial thermally curable silicone LOCA for full optical bonding (wacker Lumisil 102FC), with a component viscosity of 2000mpa.s for the a component and a viscosity of 2300mpa.s for the B component, mixed at a ratio of 1: 1.
Respectively carrying out photocuring on a test group and a control group, wherein the test group uses an LED light source with the wavelength of 395nm and the irradiation energy is 5000mJ/cm2(ii) a Curing conditions of control group were based on TDS curing conditions, wherein control group 1 employed a metal halide lamp2200mJ/cm2After the energy activation, the curing time is 50 ℃ for 30min, and the control group 2 is cured under the condition of 65 ℃ for 10 min.
The performance indexes of the test group and the control group are shown in table 1:
TABLE 1 Performance of the test and control groups
The above data fully illustrate that, compared with a control group, the adhesive prepared by the invention can be fully cured on the surface of the polarizer, and does not have the sticky phenomenon; meanwhile, the refractive index is higher, and the refractive index of each of the embodiment 1 to the embodiment 4 is higher than 1.5; and after curing, the cured product is equivalent to a commercial low-refractive-index product in transparency, haze and yellowing index, and the brightness and definition of initial display are obviously improved.
The present invention has been described in an illustrative rather than a restrictive sense, and it is within the scope of the present invention that certain changes and modifications may be effected therein without departing from the spirit and scope of the invention by one of ordinary skill in the art in light of the teachings of the disclosure.
Claims (10)
1. The high-refractive-index light-curable organic silicon adhesive is characterized by comprising the following components in parts by mass: 3-50 parts of linear polysiloxane containing sulfydryl and phenyl, 10-70 parts of linear polysiloxane containing alkenyl and phenyl, 1-50 parts of fully inert polysiloxane resin and 0.01-5 parts of photoinitiator;
the linear polysiloxane containing sulfydryl and phenyl has the viscosity of 100-100000 mPa.s at 25 ℃, and the refractive index is more than 1.5;
the linear polysiloxane containing alkenyl and phenyl has a viscosity of 100-100000 mPa.s at 25 ℃, and a refractive index > 1.5.
2. The photocurable silicone adhesive with high refractive index as recited in claim 1, wherein the molar ratio of mercapto groups in the linear polysiloxane containing mercapto groups and phenyl structures to functional groups of alkenyl groups in the linear polysiloxane containing alkenyl groups and phenyl structures is 0.2:1 to 5: 1.
3. The photocurable silicone adhesive of claim 2 wherein the mercapto group content of said linear polysiloxane containing mercapto groups and phenyl groups is between 0.1% and 5% by weight.
4. The high refractive index photocurable silicone adhesive according to claim 3, wherein said linear polysiloxane containing mercapto and phenyl structures has the structural formula:
wherein n is>0，m≥0，x＞0；R1Is composed of C1～C10Alkyl of (a), said R1Is one of methyl, ethyl, propyl, aryl or mercapto-substituted alkyl; z is CnH2nThe structure of the alkylene, and the Z is one of ethylene, propylene and butylene.
5. The photocurable silicone adhesive with high refractive index as recited in claim 2, wherein the content of alkenyl double bonds in said linear polysiloxane containing alkenyl and phenyl groups is 0.02-5 wt%.
6. The high refractive index photocurable silicone adhesive according to claim 5, wherein said linear polysiloxane containing alkenyl and phenyl groups has the formula:
wherein r is>0，s≥0，t＞0；R2Is composed of C1～C10Alkyl of (a), said R2Is one of methyl, ethyl, propyl, aryl or alkyl substituted by alkenyl; r3Is a functional group containing an alkenyl group, said R3Is one of acryloyloxy, acryloyloxypropyl, methacryloyloxypropyl, ethenyl, propenyl, butenyl, pentenyl or hexenyl.
7. A high refractive index photocurable silicone adhesive as recited in claim 1, wherein said polysiloxane resin of fully inert structure has the molecular structure:
(R4 3SiO0.5)a(R5SiO1.5)b(R6 2SiO)c(SiO2)d
the polysiloxane resin with the full inert structure is one or a mixture of MT resin, MDQ resin, MDT resin, MTQ resin and MTDQ resin containing a benzene ring structure.
8. The high refractive index photocurable silicone adhesive as recited in claim 1, wherein said photoinitiator is one or more of 2-hydroxy-2-methyl-1-phenyl-1-propanone, 2-diethoxyacetophenone, (2,4, 6-trimethylbenzoyl) diphenylphosphorus oxide, phenyl (2,4, 6-trimethylbenzoyl) ethyl phosphate, and derivatives of 2-hydroxy-2-methyl-1-propanone-1- (4-C10-13-alkylbenzene).
9. The preparation method of the high-refractive-index light-curable organic silicon adhesive is characterized by respectively preparing linear polysiloxane containing sulfydryl and phenyl, linear polysiloxane containing alkenyl and phenyl, and fully inert polysiloxane resin, and uniformly mixing the polysiloxane resin with a photoinitiator to obtain the high-refractive-index light-curable organic silicon adhesive.
10. Use of the high refractive index photocurable silicone adhesive according to any one of claims 1-8 for application to touch screens.
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Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN115710484A (en) * | 2022-12-02 | 2023-02-24 | 武汉科技大学 | Photocuring organic silicon adhesive and preparation method thereof |
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