CN113845622A - High-refractive-index and high-brightness prism resin for laminating film and preparation method thereof - Google Patents

High-refractive-index and high-brightness prism resin for laminating film and preparation method thereof Download PDF

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CN113845622A
CN113845622A CN202111192977.4A CN202111192977A CN113845622A CN 113845622 A CN113845622 A CN 113845622A CN 202111192977 A CN202111192977 A CN 202111192977A CN 113845622 A CN113845622 A CN 113845622A
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resin
parts
prism
acrylate
graphene oxide
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CN113845622B (en
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牛牧
郭凯
曹磊
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Suzhou Nuozhiwen Technology Development Co.,Ltd.
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Changzhou Bangrui New Material Technology Co ltd
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F279/00—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00
    • C08F279/02—Macromolecular compounds obtained by polymerising monomers on to polymers of monomers having two or more carbon-to-carbon double bonds as defined in group C08F36/00 on to polymers of conjugated dienes
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2/00—Processes of polymerisation
    • C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F289/00—Macromolecular compounds obtained by polymerising monomers on to macromolecular compounds not provided for in groups C08F251/00 - C08F287/00
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/02—Elements
    • C08K3/04—Carbon
    • C08K3/042—Graphene or derivatives, e.g. graphene oxides
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/02—Ingredients treated with inorganic substances
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K9/00—Use of pretreated ingredients
    • C08K9/04—Ingredients treated with organic substances
    • C08K9/06—Ingredients treated with organic substances with silicon-containing compounds
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
    • G02B1/10—Optical coatings produced by application to, or surface treatment of, optical elements
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K3/00—Use of inorganic substances as compounding ingredients
    • C08K3/18—Oxygen-containing compounds, e.g. metal carbonyls
    • C08K3/20—Oxides; Hydroxides
    • C08K3/22—Oxides; Hydroxides of metals
    • C08K2003/2244—Oxides; Hydroxides of metals of zirconium

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  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Adhesives Or Adhesive Processes (AREA)
  • Laminated Bodies (AREA)
  • Polymerisation Methods In General (AREA)

Abstract

The invention provides a prism resin film for a laminating film with high refractive index and high brightness and a preparation method thereof.

Description

High-refractive-index and high-brightness prism resin for laminating film and preparation method thereof
Technical Field
The invention relates to the field of high polymer materials, in particular to prism resin for a high-refractive-index and high-brightness laminating film and a preparation method thereof.
Background
The liquid crystal is a display technology which cannot self-emit light, the optical brightness of the liquid crystal depends on a backlight module at the rear part, and the quality of the backlight module determines the display effect of the product. The brightness of the LCD can be improved to more than twice of the original brightness by adding a plurality of thin brightness enhancement films for optical components such as backlight sources and the like, and the importance of the visible optical adhesive film in the liquid crystal technology is achieved. The backlight module optical laminating film is mainly used for various liquid crystal display backlight products such as televisions, mobile phone liquid crystal modules, monitors, MP4, digital cameras, vehicle-mounted series and the like.
Brightness enhancement films can be classified into three categories according to their effects: traditional brightness enhancement films, microlens films, prism films, and reflective polarizing brightness enhancement films. The prism adhesive film is widely and mature in domestic market, and the common prism adhesive film consists of three parts: a prism adhesive film and a front/back surface protective film. The prism attaching film is provided with a double-layer material: the base material is optical grade transparent plastic such as PET or PC, the prism structure layer on the base material is usually composed of prism resin formed by photocuring, and the prism resin enables light emitted by a light source to be reflected by a prism surface and finally to be emitted at an expected fixed angle by controlling the angle of the light. The refractive index is one of the most important hardness indexes of the prism resin. Prism resins are often acrylates, and the refractive index of conventional acrylate monomers and acrylate oligomers is 1.43-1.50, so in some high-end applications where refractive index requirements are above 1.6, there are few prism resins that can achieve refractive index, brightness and physical properties at the same time.
Therefore, the development of a prism resin for a bonding film having a high refractive index and high luminance is an urgent problem to be solved.
Disclosure of Invention
In order to overcome the defects in the prior art, the invention provides the prism resin film for the laminating film with high refractive index and high brightness and the preparation method thereof.
In the present invention, the content percentages are weight percentages unless otherwise specified.
In order to achieve the above object, the present invention is achieved by the following aspects:
in a first aspect, the present invention provides a prism resin for a high refractive index and high luminance laminating film, wherein the prism resin comprises the following raw materials, by weight:
20-70 parts of polybutadiene acrylate; 3-30 parts of tackifying resin; 30-60 parts of reactive diluent; 0.5-10 parts of graphene oxide modified nano-zirconia; 1-20 parts of a photoinitiator; 0.5-5 parts of thermal initiator.
Preferably, the raw materials for preparing the prism resin comprise the following components in parts by weight:
40-60 parts of polybutadiene acrylate; 8-10 parts of tackifying resin; 30-50 parts of a reactive diluent; 2-7 parts of graphene oxide modified nano-zirconia; 4-8 parts of a photoinitiator; 1-2 parts of thermal initiator.
In some embodiments, the polybutadiene acrylate is prepared by anionic reaction of hydroxyl-terminated polybutadiene and an acryloyl chloride compound.
In some specific embodiments, the hydroxyl-terminated polybutadiene is selected from one or a mixture of Krasol TM LBH-2000, Krasol TM LBH-3000, Krasol TM LBH-P-2000, Krasol TM LBH-P-3000, Poly R20LM, Poly R45HTLO, Poly R45V series from Krasol corporation;
preferably one or more of Krasol TM LBH-2000, Krasol TM LBH-P-2000 and Krasol TM LBH-P-2000.
In some specific embodiments, the acryloyl chloride compound is one or more of acryloyl chloride, methacryloyl chloride, 2-ethylacryloyl chloride, or 2-propylacryloyl chloride.
In some specific embodiments, the method for preparing the polybutadiene acrylate comprises: adding potassium and naphthalene which is sublimated to remove impurities into tetrahydrofuran in a mass ratio of 1:3-4, reacting for 24-48h under the protection of inert gas at room temperature, and filtering to obtain potassium naphthalene for later use; reacting hydroxyl-terminated polybutadiene and the potassium naphthalene under the protection of inert gas at room temperature for 1-5h, adding an acryloyl chloride compound, continuing to react for 0.5-1.5h, filtering, washing and drying to obtain polybutadiene acrylate, wherein the molar ratio of the hydroxyl-terminated polybutadiene to the potassium naphthalene to the acryloyl chloride compound is 1: 2.1-2.3: 2.1-2.3.
As a preferred embodiment, the hydroxyl-terminated polybutadiene reacts with potassium naphthalene to generate potassium alkoxide with high reactivity, and the potassium alkoxide can directly react with acryloyl chloride compound to generate polybutadiene acrylate without using organic amine catalyst. The traditional organic amine catalyst is avoided, amine impurities possibly caused by the polybutadiene acrylate serving as a main monomer raw material of the prism resin for the laminating film are greatly reduced, the overall stability and peel strength of the system can be effectively improved, and the transparency of the system is improved.
In some specific embodiments, the tackifying resin is selected from at least one of rosin resins, petroleum resins, coumarone resins, terpene resins, oil-soluble phenolics.
In some preferred specific embodiments, the tackifying resin is a carbon five resin, specifically selected from one or more of hydrogenated carbon five resin, carbon five aliphatic petroleum resin, carbon five alicyclic petroleum resin, and carbon five modified resin.
In some preferred specific embodiments, the reactive diluent is one or a mixture of hydroxypropyl methacrylate (HPMA), 1, 6-hexanediol diacrylate (HDDA), tripropylene glycol diacrylate (TPGDA), trimethylolpropane triacrylate (TMPTA), isobornyl methacrylate (IBOA), tetrahydrofuran acrylate (THFA), methyl laurate acrylate (LMA), ethoxyethoxyethyl acrylate (EOEOEA).
In some preferred specific embodiments, the reactive diluent is a combination of 1, 6-hexanediol diacrylate (HDDA), trimethylolpropane triacrylate (TMPTA), and ethoxyethoxyethyl acrylate (EOEOEA). Preferably, the mass ratio of the 1, 6-hexanediol diacrylate (HDDA), the trimethylolpropane triacrylate (TMPTA) and the ethoxyethoxyethyl acrylate (EOEOEA) is 1: 2-8: 0.5-1. As a preferred embodiment, the reactive diluents with different functional groups in the system of the present invention cooperate with each other to provide a large number of crosslinking sites for the photo-curing system, and the photo-initiated polymerization reaction increases the crosslinking degree of the prism resin, and enhances the mechanical properties and peel strength of the prism resin, especially under high temperature and high humidity conditions.
In some specific embodiments, the graphene oxide-modified nano-zirconia is a graphene oxide-modified nano-zirconia modified with a silane coupling agent.
In some specific embodiments, the graphene oxide modified nano-zirconia is prepared by the following steps:
(1) uniformly mixing 1-5g of graphene with 100-200mL of 95% concentrated sulfuric acid, stirring for 1-2h under an ice bath condition, then adding 5-20g of potassium permanganate solution, continuing stirring for 2-3h, adding 30-50mL of 35% sulfuric acid, standing for 1-2h, washing the mixed solution until the pH value of the solution is neutral, adding the mixture obtained through centrifugation and drying into 100-200mL of ethanol aqueous solution containing 2-4g of silane coupling agent, and stirring, centrifugally separating, washing and drying to obtain silane coupling agent modified graphene oxide;
(2) and (2) uniformly mixing 2-5g of the silane coupling agent modified graphene oxide prepared in the step (1), 10-20mg of nano-zirconia and 100mL of isopropanol 500mL, adding 10-20mL of reducing agent ammonia water and ethylenediamine (the volume ratio of the ammonia water to the ethylenediamine is 1: 2), heating to 80-90 ℃, refluxing for 4-6h, washing the product until the pH value is neutral, and drying to obtain the graphene oxide modified nano-zirconia.
Preferably, the silane coupling agent is any one or a mixture of more than two of a coupling agent KH550, a coupling agent KH560 and a coupling agent KH 570.
In some specific embodiments, the nano zirconia has a particle size of 30 to 40 nanometers.
The inventor finds that the graphene oxide modified nano-zirconia is added into the prism resin in a certain proportion, so that the mechanical property and the mechanical property of the prism resin are effectively improved, the refractive index of a resin system is improved, the reflection loss of an obtained prism structure is reduced, the luminance of a brightness enhancement film can be further improved, and the requirement of the brightness enhancement film on higher optical performance is met. After the graphene is oxidized, oxygen-containing functional groups on the graphene are increased, so that the graphene is more active than the graphene, and the graphene is more easily combined with zirconium oxide powder after being modified by a silane coupling agent and plays a synergistic effect in an acrylate matrix resin system.
Preferably, the mass ratio of the silane coupling agent modified graphene oxide to the nano-zirconia is 200-250: 1. The preferred embodiment can achieve better system performance, probably because the mass ratio is less agglomerated and easy to disperse, and can fully exert the crosslinking effect of the rigid particles.
The photoinitiator is a compound which can absorb energy with certain wavelength in an ultraviolet region (250-420 nm) or a visible light region (400-800 nm) to generate free radicals, cations and the like so as to initiate the polymerization, crosslinking and curing of monomers. In some specific embodiments, the photoinitiator is 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxycyclohexylphenylmethanone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate, 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone, or mixtures thereof, One or more of methyl benzoylformate. Preferably 2-hydroxy-2-methyl-1-phenylpropanone (otherwise known as photoinitiator 1173).
In some specific embodiments, the thermal initiator is one or a mixture of Azobisisobutyronitrile (AIBN), Azobisisoheptonitrile (ABVN), azobisisobutyramidine hydrochloride (AIBA) or azobisisobutyrimidazoline hydrochloride (AIBI).
In some specific embodiments, the raw materials for preparing the prism resin according to the present invention further include one or more of a stabilizer, a plasticizer, a coupling agent, an antioxidant, a light transmittance modifier, a compatibilizer, or an anti-fogging agent.
As examples of stabilizers, including, but not limited to, zinc stearate, calcium glycerophosphate, zinc carbonate; in one embodiment, the weight of the stabilizer of the present invention is 0 to 1 wt% of the total weight of the raw materials for preparing the prism resin.
Examples of plasticizers include, but are not limited to, hydrogenated terpene resins, polybutadiene oligomers, ether alcohol dibasic acid diesters, ether glycol monobasic acid diesters, dioctyl sebacate; in one embodiment, the weight of the plasticizer is 0 to 1 wt% of the total weight of the raw materials for preparing the prism resin.
Examples of the antioxidant include, but are not limited to, one or more of hindered phenol-based antioxidants and phosphite-based antioxidants, and specifically, may be selected from compounds such as Irganox 1141, 1010, 1076, 168, BNX1000, diphenylamine, p-phenylenediamine and dihydroquinoline, and derivatives or polymers thereof, 2, 6-t-butyl-4-methylphenol, bis (3, 5-t-butyl-4-hydroxyphenyl) sulfide, pentaerythrityl tetrakis [ β - (3, 5-t-butyl-4-hydroxyphenyl) propionate ], bisdodecanol ester, bistetradecanol ester and bisoctadecanol ester, trioctyl ester, tridecyl ester, tridodecanol ester and trihexadecanol ester; in one embodiment, the antioxidant is 0 to 3% by weight of the total weight of the raw materials for preparing the prism resin.
Examples of light transmission modifiers include, but are not limited to, 1,3, 5-tri-tert-butylaminobenzene, dibenzylidene sorbitol (DBS), 1,3:2, 4-di-p-methylbenzylidene sorbitol, p-chloro-p-methyldibenzylidene sorbitol, polyvinylcyclobutane, polyvinylcyclohexane, polyvinylcyclopentane, polyvinyl-2-methylcyclohexane, and poly-3-methyl-1-butene; in one embodiment, the weight of the light transmittance modifier is 0 to 1 wt% of the total weight of the raw materials for preparing the prism resin.
Examples of the anti-fogging agent include, but are not limited to, a polyamide methanol solution, an ionic surfactant methanol solution, a polyethylene glycol perfluoroalkyl ether isopropyl alcohol solution; in one embodiment, the weight of the antifogging agent of the present invention is 0 to 1 wt% of the total weight of the raw materials for preparing the prism resin.
In a second aspect, the present invention provides a method for preparing a prism resin for a high-refractive-index and high-luminance laminating film, comprising the steps of:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1-2h under the condition of nitrogen, and controlling the temperature to be 60-80 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with tackifying resin, an active diluent and a photoinitiator, mixing for 0.5-2h under the condition of nitrogen, controlling the temperature to be 40-50 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
In some preferred specific embodiments, in the step (2), the prepolymer and the tackifying resin are mixed for 0.5 to 1 hour under the condition of nitrogen, and the temperature is controlled to be 40 to 50 ℃; then adding reactive diluent and photoinitiator, continuously mixing for 0.5-1h, and controlling the temperature to be 40-50 ℃. The inventors have found that the preferred embodiment allows for more uniform mixing between the raw materials, which is beneficial for improving the stability and peel strength of the system.
In some preferred embodiments, step (2) further comprises adding an antioxidant.
The inventor of the application finds that the prism resin suitable for the optical film is obtained by adopting specific types of acrylate, tackifying resin and active diluent and adding the nano-zirconia modified by the graphene oxide through the interaction between the raw materials, so that the prism resin has high refractive index and brightness.
On the basis of the common knowledge in the field, the above preferred conditions can be combined randomly to obtain the preferred embodiments of the invention. The reagents and starting materials used in the present invention are not specifically described and are commercially available.
The positive progress effects of the invention are as follows: by controlling the selection and the proportion of the raw material components, the prism resin for the laminating film with excellent performance is obtained, and the optical film and the prism resin can be well bonded. The prism resin has simple preparation process and low cost.
Detailed Description
The invention is further illustrated by the following examples, which are not intended to limit the scope of the invention. The experimental methods without specifying specific conditions in the following examples were selected according to the conventional methods and conditions, or according to the commercial instructions.
When an amount, concentration, or other value or parameter is expressed as a range, preferred range, or as a range of upper preferable values and lower preferable values, this is to be understood as specifically disclosing all ranges formed from any pair of any upper range limit or preferred value and any lower range limit or preferred value, regardless of whether ranges are separately disclosed. For example, when a range of "1 to 5" is disclosed, the described range should be interpreted to include the ranges "1 to 4", "1 to 3", "1 to 2 and 4 to 5", "1 to 3 and 5", and the like. When a range of values is described herein, unless otherwise stated, the range is intended to include the endpoints thereof and all integers and fractions within the range.
The following examples are intended to illustrate the invention but are not intended to limit the scope of the invention. It should be understood that although a few embodiments of practicing the present invention have been illustrated herein, those skilled in the art will appreciate, in light of the present disclosure, that numerous modifications may be made without departing from the spirit and intended scope of the invention. It is also to be understood that the terminology used herein is for the purpose of describing particular embodiments only and is not intended to be limiting, since the scope of the present invention will be defined only by the appended claims and equivalents thereof.
The starting materials in the following examples and comparative examples are commercially available unless otherwise specified.
Wherein,
the graphene oxide modified nano-zirconia (self-made A) is prepared by the following steps:
(1) uniformly mixing 2g of graphene with 100mL of 95% concentrated sulfuric acid, stirring for 1h under an ice bath condition, then adding 10g of potassium permanganate solution, continuously stirring for 2h, adding 50mL of 35% sulfuric acid, standing for 2h, washing the mixed solution until the pH value of the solution is neutral, adding a mixture obtained through centrifugation and drying into 150mL of ethanol aqueous solution containing 2.5g of silane coupling agent KH560, and stirring, centrifugally separating, washing and drying to obtain silane coupling agent modified graphene oxide;
(2) and (2) uniformly mixing 4g of the silane coupling agent modified graphene oxide prepared in the step (1), 10mg of nano-zirconia and 500mL of isopropanol, adding 15mL of reducing agent ammonia water and ethylenediamine (the volume ratio of the ammonia water to the ethylenediamine is 1: 2), heating to 80 ℃, refluxing for 4h, washing the product until the pH value is neutral, and drying to obtain the graphene oxide modified nano-zirconia.
The preparation method of the graphene oxide modified nano zirconia (self-made B) is the same as that of the graphene oxide modified nano zirconia (self-made A), and the differences are as follows: and (2) uniformly mixing 4g of the silane coupling agent modified graphene oxide prepared in the step (1), 20mg of nano-zirconia and 500mL of isopropanol, adding 15mL of reducing agent ammonia water and ethylenediamine (the volume ratio of the ammonia water to the ethylenediamine is 1: 2), heating to 80 ℃, refluxing for 4h, washing the product until the pH value is neutral, and drying to obtain the graphene oxide modified nano-zirconia.
Example 1
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 50 parts of polybutadiene acrylate (NISSO-PB TE-2000 from Japan Caoda), 8 parts of tackifying resin hydrogenated carbon penta resin (ring-and-ball softening point is 100 ℃), 50 parts of active diluent (a mixture of HDDA, IBOA and EOEOEA according to the mass ratio of 1: 2: 7), 6 parts of graphene oxide modified nano zirconia (homemade A), 1 part of thermal initiator Azobisisobutyronitrile (AIBN) and 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173).
The preparation method of the prism resin comprises the following steps:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 65 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with tackifying resin, an active diluent and a photoinitiator, mixing for 2h under the condition of nitrogen, controlling the temperature to be 50 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
Example 2
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 50 parts of polybutadiene acrylate (NISSO-PB TE-2000 from Japan Caoda), 8 parts of tackifying resin hydrogenated carbon penta resin (the softening point of a ring-and-ball method is 100 ℃), 50 parts of active diluent (a mixture of HDDA, TMPTA and EOEOEA according to the mass ratio of 1: 5: 0.8), 6 parts of graphene oxide modified nano zirconia (self-made A), 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
The preparation method of the prism resin comprises the following steps:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 65 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with tackifying resin, reactive diluent, photoinitiator and antioxidant, mixing for 2h under the condition of nitrogen, controlling the temperature to be 50 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
Example 3
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 50 parts of polybutadiene acrylate (self-made), 8 parts of tackifying resin hydrogenated carbon penta resin (softening point of a ring-and-ball method is 100 ℃), 50 parts of active diluent (mixture of HDDA, TMPTA and EOEOEA according to a mass ratio of 1: 5: 0.8), 6 parts of graphene oxide modified nano-zirconia (self-made B), 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
The preparation method of the polybutadiene acrylate (self-made) comprises the following steps: adding potassium and naphthalene which is sublimated to remove impurities into tetrahydrofuran in a mass ratio of 1:3, reacting for 24 hours under the protection of inert gas at room temperature, and filtering to obtain potassium naphthalene for later use; and (2) reacting hydroxyl-terminated polybutadiene (Krasol TM LBH-2000) and the potassium naphthalene for 1h under the protection of inert gas at room temperature, adding acryloyl chloride, continuously reacting for 1.5h, filtering, washing and drying to obtain polybutadiene acrylate, wherein the molar ratio of the hydroxyl-terminated polybutadiene to the potassium naphthalene to the acryloyl chloride is 1: 2.2: 2.2.
the prism resin was prepared in the same manner as in example 2.
Example 4
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 50 parts of polybutadiene acrylate (self-made), 8 parts of tackifying resin hydrogenated carbon penta resin (softening point of a ring-and-ball method is 100 ℃), 50 parts of active diluent (mixture of HDDA, IBOA and EOEOEA according to a mass ratio of 1: 2: 7), 6 parts of graphene oxide modified nano-zirconia (self-made B), 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
Wherein the preparation method of polybutadiene acrylate (self-made) is the same as that of example 3; the prism resin was prepared in the same manner as in example 3.
Example 5
A prism resin for a high-refractive-index high-luminance laminating film, which is prepared from the same raw materials as in example 4, except that: 50 parts of active diluent (a mixture of HDDA, TMPTA and EOEOEA according to the mass ratio of 1: 3: 3).
Wherein the preparation method of polybutadiene acrylate (self-made) is the same as that of example 4; the prism resin was prepared in the same manner as in example 4.
Example 6
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 70 parts of polybutadiene acrylate (self-made), 7 parts of tackifying resin hydrogenated carbon penta resin (softening point of a ring-and-ball method is 100 ℃), 30 parts of active diluent (mixture of HDDA, TMPTA and EOEOEA according to a mass ratio of 1: 5: 0.8), 6 parts of graphene oxide modified nano-zirconia (self-made B), 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
Wherein the preparation method of polybutadiene acrylate (self-made) is the same as that of example 4; the prism resin was prepared in the same manner as in example 4.
Example 7
A prism resin for a high-refractive-index high-luminance laminating film, which is prepared from the same raw materials as those in example 3, except that: the preparation method of the prism resin is different, and comprises the following steps:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 65 ℃ to obtain a prepolymer for later use;
(2) firstly, mixing the prepolymer and tackifying resin for 0.5h under the condition of nitrogen, and controlling the temperature to be 50 ℃; then adding an active diluent, a photoinitiator and an antioxidant, continuously mixing for 0.5h, controlling the temperature to be 40 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
Example 8
A prism resin for a high-refractive-index and high-brightness laminating film comprises the following raw materials in parts by weight: 60 parts of polybutadiene acrylate (self-made), 15 parts of tackifying resin hydrogenated carbon penta resin (softening point of a ring-and-ball method is 100 ℃), 40 parts of active diluent (mixture of HDDA, TMPTA and EOEOEA according to a mass ratio of 1: 5: 0.8), 6 parts of graphene oxide modified nano-zirconia (self-made B), 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
The preparation method of the prism resin comprises the following steps:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 60 ℃ to obtain a prepolymer for later use;
(2) firstly, mixing the prepolymer and tackifying resin for 1h under the condition of nitrogen, and controlling the temperature to be 50 ℃; then adding an active diluent, a photoinitiator and an antioxidant, continuously mixing for 0.5h, controlling the temperature to be 40 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
Comparative example 1
The resin preparation raw material (without tackifying resin) comprises the following components in parts by weight: 58 parts of polybutadiene acrylate (NISSO-PB TE-2000 from Japan Caoda), 50 parts of active diluent (a mixture of HDDA, TMPTA and EOEOEA according to the mass ratio of 1: 5: 0.8), 6 parts of graphene oxide modified nano-zirconia (homemade B), 1 part of thermal initiator Azobisisobutyronitrile (AIBN) and 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173).
The preparation method of the resin comprises the following steps:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 65 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with an active diluent and a photoinitiator, mixing for 1.5h under the condition of nitrogen, and controlling the temperature to be 50 ℃ to obtain the resin.
Comparative example 2
The resin comprises the following raw materials in parts by weight: 50 parts of polybutadiene acrylate (NISSO-PB TE-2000 from Japan Caoda), 8 parts of tackifying resin hydrogenated carbon five resin (ring-and-ball softening point is 100 ℃), 50 parts of active diluent (a mixture of HDDA, TMPTA and EOEOEA according to the mass ratio of 1: 5: 0.8), 6 parts of unmodified nano-zirconia, 1 part of thermal initiator Azobisisobutyronitrile (AIBN), 5 parts of photoinitiator 2-hydroxy-2-methyl-1-phenyl acetone (1173) and 10100.6 parts of antioxidant.
The preparation method of the resin comprises the following steps:
(1) firstly, uniformly mixing polybutadiene acrylate and nano zirconia, adding a thermal initiator, mixing for 1.5 hours under the condition of nitrogen, and controlling the temperature to be 65 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with tackifying resin, reactive diluent, photoinitiator and antioxidant, mixing for 2h under the condition of nitrogen, and controlling the temperature to be 50 ℃ to obtain the resin.
And (3) performance testing:
the samples obtained in the above examples and comparative examples were subjected to the following performance tests, the test standards and methods, and the test results are shown in table 1:
(1) initial viscosity: referring to the test of GB4852-84, prism resin samples were tested by using a slant roll ball method, prism resin was coated on a PET film 100mm long and 50mm wide and uv-cured, the samples were placed on a slant table with a tilt of 30 ° during the test, initial adhesion was represented by testing the largest number of balls that could be stuck by the prism resin, and errors were excluded three times per sample test.
(2) 180 ° peel strength: referring to the test of GB/T2792-81, the 180-degree peeling force test is carried out on the prism resin by an intelligent electronic tensile machine (XLW, Jinan Languan optical motor technology Co., Ltd.). Coating prism resin on a PET film with the length of 100mm and the width of 25mm, carrying out ultraviolet light curing, then adhering the cured adhesive film on a special steel plate for carrying out a peeling test, wherein the peeling speed is 300mm/min, and the test temperature is 25 ℃.
(3) Refractive index: reference GB/T6488-;
(4) appearance: and (5) observing with naked eyes.
TABLE 1
Example 1 Example 2 Example 3 Example 4 Example 5 Example 6 Example 7 Example 8 Comparative example 1 Comparative example 2
Initial tack 10 9 12 11 11 9 14 12 6 5
180 degree peel strength (N/25 mm) 23 24 30 28 27 25 35 27 14 10
Refractive index (nD)25） 1.58 1.58 1.63 1.61 1.61 1.6 1.64 1.62 1.51 1.43
Appearance of the product Yellow transparent Light yellow transparent Colorless and transparent Colorless and transparent Colorless and transparent Colorless and transparent Colorless and transparent Colorless and transparent Yellow transparent Yellow transparent
As can be seen from Table 1, the prism resin suitable for the optical film is obtained by adopting specific types of acrylate, tackifying resin and reactive diluent and adding the graphene oxide modified nano-zirconia through interaction among raw materials, so that the prism resin has high initial viscosity and peel strength after film forming, has high refractive index and transparency, can reduce reflection loss of the obtained prism structure, further improves the brightness of the brightness enhancement film, and meets the requirement of the brightness enhancement film on high optical performance.
While specific embodiments of the invention have been described above, it will be appreciated by those skilled in the art that this is by way of example only, and that the scope of the invention is defined by the appended claims. Various changes and modifications to these embodiments may be made by those skilled in the art without departing from the spirit and scope of the invention, and these changes and modifications are within the scope of the invention.

Claims (10)

1. The prism resin for the laminating film with high refractive index and high brightness is characterized by comprising the following raw materials in parts by weight:
20-70 parts of polybutadiene acrylate;
3-30 parts of tackifying resin;
30-60 parts of reactive diluent;
0.5-10 parts of graphene oxide modified nano-zirconia;
1-20 parts of a photoinitiator;
0.5-5 parts of thermal initiator.
2. The prism resin for a bonding film according to claim 1, wherein the polybutadiene acrylate is prepared by anionic reaction of hydroxyl-terminated polybutadiene and an acryloyl chloride compound; the acryloyl chloride compound is one or a mixture of more of acryloyl chloride, methacryloyl chloride, 2-ethyl acryloyl chloride or 2-propyl acryloyl chloride.
3. The prism resin for a conformable film according to claim 1, wherein the tackifier resin is at least one selected from the group consisting of rosin resin, petroleum resin, coumarone resin, terpene resin, and oil-soluble phenol resin;
preferably, the tackifying resin is one or more selected from hydrogenated carbon five resin, carbon five aliphatic petroleum resin, carbon five alicyclic petroleum resin and carbon five modified resin.
4. The prism resin for a conformable film according to claim 1, wherein the reactive diluent is one or a mixture of hydroxypropyl methacrylate (HPMA), 1, 6-hexanediol diacrylate (HDDA), tripropylene glycol diacrylate (TPGDA), trimethylolpropane triacrylate (TMPTA), isobornyl methacrylate (IBOA), tetrahydrofuran acrylate (THFA), methyl laurate acrylate (LMA), and ethoxyethoxyethyl acrylate (EOEOEA);
preferably, the reactive diluent is a composition of 1, 6-hexanediol diacrylate (HDDA), trimethylolpropane triacrylate (TMPTA) and ethoxyethoxyethyl acrylate (EOEOEA) in a mass ratio of 1: 2-8: 0.5-1.
5. The prism resin for a conformable film according to claim 1, wherein the graphene oxide-modified nano zirconia is a graphene oxide-modified nano zirconia modified with a silane coupling agent;
the silane coupling agent is any one or more than two of a coupling agent KH550, a coupling agent KH560 or a coupling agent KH 570.
6. The prism resin for a bonding film according to claim 1, wherein the photoinitiator is 2-hydroxy-2-methyl-1-phenylpropanone, 1-hydroxycyclohexylphenylketone, 2-methyl-2- (4-morpholinyl) -1- [4- (methylthio) phenyl ] -1-propanone, 2,4, 6-trimethylbenzoyl-diphenylphosphine oxide, ethyl 2,4, 6-trimethylbenzoylphenylphosphonate, 2-dimethylamino-2-benzyl-1- [4- (4-morpholinyl) phenyl ] -1-butanone, 2-hydroxy-2-methyl-1- [4- (2-hydroxyethoxy) phenyl ] -1-propanone, 2-hydroxy-2-methyl-1- [4- (4-hydroxyethoxy) phenyl ] -1-propanone, or a mixture thereof, One or more of methyl benzoylformate; and/or the presence of a gas in the gas,
the thermal initiator is one or a mixture of Azodiisobutyronitrile (AIBN), Azodiisoheptanonitrile (ABVN), azodiisobutyl amidine hydrochloride (AIBA) or azodiisobutyl imidazoline hydrochloride (AIBI).
7. The prism resin for a conformable film according to claim 1, wherein the raw material for producing the prism resin further comprises one or more of a stabilizer, a plasticizer, a coupling agent, an antioxidant, a light transmittance modifier, a compatibilizer, and an antifogging agent.
8. A method for preparing a prism resin for a high-refractive-index high-luminance laminating film according to any one of claims 1 to 7, comprising the steps of:
(1) uniformly mixing polybutadiene acrylate and graphene oxide modified nano zirconia, adding a thermal initiator, mixing for 1-2h under the condition of nitrogen, and controlling the temperature to be 60-80 ℃ to obtain a prepolymer for later use;
(2) and (2) uniformly mixing the prepolymer obtained in the step (1) with tackifying resin, an active diluent and a photoinitiator, mixing for 0.5-2h under the condition of nitrogen, controlling the temperature to be 40-50 ℃, and obtaining the prism resin for the laminating film with high refractive index and high brightness.
9. The preparation method according to claim 8, wherein in the step (2), the prepolymer and the tackifying resin are mixed for 0.5 to 1 hour under the condition of nitrogen, and the temperature is controlled to be 40 to 50 ℃; then adding reactive diluent and photoinitiator, continuously mixing for 0.5-1h, and controlling the temperature to be 40-50 ℃.
10. The method according to claim 8, wherein the step (2) further comprises adding an antioxidant.
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