CN108003567A - A kind of UV-cured resin of high index of refraction and preparation method thereof - Google Patents

A kind of UV-cured resin of high index of refraction and preparation method thereof Download PDF

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Publication number
CN108003567A
CN108003567A CN201711076924.XA CN201711076924A CN108003567A CN 108003567 A CN108003567 A CN 108003567A CN 201711076924 A CN201711076924 A CN 201711076924A CN 108003567 A CN108003567 A CN 108003567A
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China
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parts
cured resin
acrylic acid
high index
refraction
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CN201711076924.XA
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Chinese (zh)
Inventor
朱焰焰
马苹苹
郑杰
陈士冰
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Beichuan Ruihui Technology Co Ltd
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Beichuan Ruihui Technology Co Ltd
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Priority to CN201711076924.XA priority Critical patent/CN108003567A/en
Publication of CN108003567A publication Critical patent/CN108003567A/en
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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/02—Polycondensates containing more than one epoxy group per molecule
    • C08G59/04—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof
    • C08G59/06—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols
    • C08G59/063—Polycondensates containing more than one epoxy group per molecule of polyhydroxy compounds with epihalohydrins or precursors thereof of polyhydric phenols with epihalohydrins
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
    • C08G59/14—Polycondensates modified by chemical after-treatment
    • C08G59/1433—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds
    • C08G59/1438—Polycondensates modified by chemical after-treatment with organic low-molecular-weight compounds containing oxygen
    • C08G59/1455—Monocarboxylic acids, anhydrides, halides, or low-molecular-weight esters thereof
    • C08G59/1461—Unsaturated monoacids
    • C08G59/1466—Acrylic or methacrylic acids
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L63/00—Compositions of epoxy resins; Compositions of derivatives of epoxy resins
    • C08L63/10—Epoxy resins modified by unsaturated compounds
    • 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
    • C08K2003/2237—Oxides; Hydroxides of metals of titanium
    • C08K2003/2241—Titanium dioxide
    • 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
    • C08K2201/00—Specific properties of additives
    • C08K2201/011—Nanostructured additives
    • 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

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Emergency Medicine (AREA)
  • General Chemical & Material Sciences (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Epoxy Resins (AREA)

Abstract

The invention discloses a kind of UV-cured resin of high index of refraction, is made of the raw material of following parts by weight：4,4 ' 10~30 parts of dihydroxy diphenyl sulfides, 100~200 parts of epoxychloropropane, 1~4 part of tetra-n-butyl ammonium bromide, 10~25 parts of lye, 10~35 parts of acrylic acid, 1~5 part of triphenylphosphine, 10~30 parts of acrylic resin containing sulfydryl, 2~20 parts of inorganic nano-particle titanium dioxide, 40~100 parts of reactive diluent.Preparation method is：In prepolymer（Sulfur-bearing acrylic acid epoxy resin）Middle introducing group containing sulfydryl, inorganic nano-particle.The UV-cured resin of the present invention, has high index of refraction（1.48~1.65）, refractive index is adjustable, light transmittance is high（≥90%）, cure times it is short（≤10s）The advantages that, it disclosure satisfy that the requirement of flexible display device core component CRF absorbed layer high molecular materials.

Description

A kind of UV-cured resin of high index of refraction and preparation method thereof
Technical field
The present invention relates to a kind of UV-cured resin of high index of refraction and preparation method thereof, belongs to new material technology neck Domain.
Background technology
Flexible Displays are the research hotspots of current Display Technique, are widely used in the fields such as communication, medium, mainly organic Light emitting diode (OLED), flexible liquid crystal (Flexible-LCD), Electronic Paper (EPD) etc..The display to shine as a kind of active Technology, the problem of being remarkably decreased under bright room condition and outdoor conditions there are contrast, is, it is necessary to should on flexible display device With bright room contrast functional membrane (Contrast Refined Film, CRF) is improved, realize and the strong of ambient light is absorbed and right The high transmission of light is sent inside display device, improves the bright room contrast of flexible display device within the specific limits, is met flexible Application requirement of the display device outdoors and under the conditions of portable use.
At present, conventional CRF is based on high-selenium corn coating, by film surface design optical texture (such as：High saturating Cross in the film layer of rate and imprint out the micro-structure groove of different shapes such as trapezoidal, triangle, rectangle, and fill in micro-structure groove black Color absorber coatings), realize the absorption to ambient light, there are the shortcomings of light transmittance is low, pliability is poor, thickness is big for this method.
Application demand of the applicant of the present invention for flexible display device to CRF, using the total reflection principle of light, uses The adjustable UV-cured resin of high and low refractive index, has been prepared a kind of by PET base membrane layers, optical microstructures functional layer, absorption The novel C RF (number of patent application CN201610143123.X, publication number 105824060A) of layer, protective layer four-layer structure composition, The optically functional film has the advantages that light transmittance is high, pliability is good, thickness is thin, while solves flexible display device in bright room bar The problem of contrast is remarkably decreased under part and outdoor conditions.
Correlation UV-cured resin respectively has feature both at home and abroad, but cures in existing optical microstructures absorbed layer ultraviolet light Problems with is still suffered from resin：High index of refraction, each functions of CRF of CRF requirements are such as unsatisfactory in the case of high transparency Adhesive force is poor between film layer, resin material poor in flexibility, the problems such as shrinking percentage is larger.Therefore, it is necessary to research and develop a kind of performance Excellent UV-cured resin.
The content of the invention
For the above-mentioned prior art, the deficiency for the requirement for being difficult to meet CRF for existing UV-cured resin Place, the present invention provides a kind of CRF use, high index of refraction, the UV light that refractive index is adjustable, light transmittance is high, cure times are short Change resin, and preparation method thereof.The ultraviolet light that the present invention goes out function admirable by being formulated design and performance test screen cures tree Fat and activated monomer, the performance such as the design and optimization of material prescription, comprehensive pliability, shrinking percentage is carried out by adding suitable auxiliary agents While, reach UV-cured resin high index of refraction under high transparency, and adjustable requirement (it is contour will to contain mercapto, sulphur The atom or group of Lorentz-Lorenz molar refraction are designed, and by controlling different functional groups and addition, prepare high index of refraction UV-cured resin, general radically curing shrinking percentage is larger, is 5%~10%, and cationic curing shrinking percentage is relatively low, For 0.5%~3.0%, the present invention by using cation-free radical dual cure reactive diluent, by the shrinking percentage of resin Control is 0.5%~3.0%；Acrylic resin containing sulfydryl, which introduces, at the same time can improve the flexible of overall UV-cured resin Property, pliability is up to 7 grades).On the basis of its coating performance is realized, emphasis solves refractive index, translucency and photocuring The technical problems such as speed.
The present invention is achieved by the following technical solutions：
A kind of UV-cured resin of high index of refraction, is made of the raw material of following parts by weight：
4,10~30 parts of 4 '-dihydroxy diphenyl sulfide, 100~200 parts of epoxychloropropane, tetra-n-butyl ammonium bromide 1~4 Part, mass fraction be 15%~25% 10~25 parts of lye, 10~35 parts of acrylic acid, 1~5 part of triphenylphosphine, containing sulfydryl third 10~30 parts of olefin(e) acid resin, 2~20 parts of inorganic nano-particle titanium dioxide, 40~100 parts of reactive diluent.
The lye is selected from combination more than one or both of sodium hydrate aqueous solution, potassium hydroxide aqueous solution.
The acrylic resin containing sulfydryl can conventional market be commercially available, the present invention is used limited purchased from the bright scientific and technological share of China Company, acrylic resin containing sulfydryl, BHS-0737.
The reactive diluent is selected from one or both of methyl acrylate (MA), siloxanes (BAPD) that phenyl substitutes Combination above.
Its preparation method comprises the following steps：
(1) 4,4 '-dihydroxy diphenyl sulfide, epoxychloropropane and tetra-n-butyl ammonium bromide are added into reaction kettle, 90 DEG C~105 DEG C, 1~1.5h is stirred under the conditions of nitrogen atmosphere, lye is then slowly added dropwise, reacts 6~7h, it is prepared 4,4 '- Dihydroxy diphenyl sulfide epoxy resin；
(2) above-mentioned reaction system is cooled to 80~90 DEG C, and acrylic acid and triphenylphosphine, nitrogen atmosphere are added into reaction kettle 3~4h of lower stirring reaction, is prepared sulfur-bearing acrylic acid epoxy resin；
(3) into sulfur-bearing acrylic acid epoxy resin add acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide and Reactive diluent, the mechanical agitation 1h under the conditions of 20~35 DEG C, is prepared the UV-cured resin of high index of refraction.
The UV-cured resin of the present invention, group containing sulfydryl is introduced in prepolymer (sulfur-bearing acrylic acid epoxy resin) (acrylic resin containing sulfydryl), inorganic nano-particle (titanium dioxide), improves the refractive index of UV-cured resin, and it is rolled over Penetrate that rate is adjustable (to realize the adjustable of refractive index by adjusting the proportion relation of group containing sulfydryl, inorganic nano-particle；Containing sulfydryl, group gets over It is more, inorganic nano-particle is more, can improve the high index of refraction of UV-cured resin, still, inorganic nano-particle can influence To the mechanical performance of whole glued membrane, such as morphotropism, mechanical property etc., so it cannot be added excessively, ratio should be appropriate).
The UV-cured resin of the present invention, can be used for preparing and improves bright room contrast functional membrane (CRF) (as optics The material of micro-structure absorbed layer), compared with prior art, have the following advantages that：
(1) present invention in prepolymer is reacted by introducing group containing sulfydryl, inorganic nano-particle raising ultraviolet light curing tree The refractive index of fat, and make its refractive index adjustable by the change of content, meet the requirement of CRF absorbed layers.
(2) present invention has the function of reactive diluent (such as MA, BAPD of dual cure by introducing in the reaction system Deng) substantially increase the photo-curing rate of UV-cured resin, meet in CRF serialization preparation process be coated with, cure, into Requirement of the type technique to UV-cured resin.
(3) UV-cured resin of the invention has high index of refraction (1.48~1.65), refractive index is adjustable, light transmittance is high The advantages that (>=90%), cure times short (≤10s), disclosure satisfy that flexible display device core component CRF absorbed layers height The requirement of molecular material.
Embodiment
With reference to embodiment, the present invention is further illustrated.
Involved instrument, reagent, material etc. in following embodiments, are existing in the prior art unless otherwise noted Conventional instrument, reagent, material etc., can be obtained by regular commercial sources.Involved experimental method in following embodiments, inspection Survey method etc., is existing normal experiment method, detection method etc. in the prior art unless otherwise noted.
Embodiment 1 prepares UV-cured resin
Step is as follows：
(1) in clean and dry reaction kettle, 4 are sequentially added, 4 '-dihydroxy diphenyl sulfide (30 parts), epoxy chloropropionate Alkane (200 parts), tetra-n-butyl ammonium bromide (3 parts), after heating stirring 1.5h under the conditions of 90 DEG C, nitrogen atmosphere, are slowly added dropwise matter The potassium hydroxide aqueous solution (20 parts) that fraction is 25% is measured, 7h is reacted, is prepared 4,4 '-dihydroxy diphenyl sulfide asphalt mixtures modified by epoxy resin Fat；
(2) 90 DEG C are cooled to, acrylic acid (30 parts) and triphenylphosphine (5 parts) are added into reaction kettle, is stirred under nitrogen atmosphere After mixing reaction 3h, sulfur-bearing acrylic acid epoxy resin is prepared；
(3) acrylic resin containing sulfydryl (30 parts), inorganic nano-particle are added in the sulfur-bearing acrylic acid epoxy resin of preparation Sub- TiO2(2 parts) and reactive diluent MA (40 parts), after mechanical agitation 1h under the conditions of 35 DEG C, it is adjustable to prepare high index of refraction UV-cured resin.After testing, which is 1.48, light transmittance 90.5%, cure times For 10s.
Embodiment 2 prepares UV-cured resin
Step is as follows：
(1) in clean and dry reaction kettle, 4 are sequentially added, 4 '-dihydroxy diphenyl sulfide (10 parts), epoxy chloropropionate Alkane (100 parts), tetra-n-butyl ammonium bromide (1 part), after heating stirring 1h under the conditions of 105 DEG C, nitrogen atmosphere, are slowly added dropwise quality Fraction is 15% sodium hydrate aqueous solution (10 parts), after reacting 6h, is prepared 4,4 '-dihydroxy diphenyl sulfide asphalt mixtures modified by epoxy resin Fat；
(2) 80 DEG C are cooled to, acrylic acid (10 parts) and triphenylphosphine (1 part) are added into reaction kettle, is stirred under nitrogen atmosphere After mixing reaction 4h, sulfur-bearing acrylic acid epoxy resin is prepared；
(3) acrylic resin containing sulfydryl (10 parts), inorganic nano-particle are added in the sulfur-bearing acrylic acid epoxy resin of preparation Sub- TiO2(20 parts), reactive diluent MA (50 parts) and BAPD (50 parts), after mechanical agitation 1h under the conditions of 30 DEG C, prepare high The adjustable UV-cured resin of refractive index.After testing, which is 1.65, light transmittance 92%, Cure times are 4s.
Embodiment 3 prepares UV-cured resin
Step is as follows：
(1) in clean and dry reaction kettle, 4 are sequentially added, 4 '-dihydroxy diphenyl sulfide (20 parts), epoxy chloropropionate Alkane (200 parts), tetra-n-butyl ammonium bromide (1 part), after heating stirring 1h under the conditions of 100 DEG C, nitrogen atmosphere, are slowly added dropwise quality Fraction is 20% sodium hydrate aqueous solution (20 parts), after reacting 6.5h, is prepared 4,4 '-dihydroxy diphenyl sulfide asphalt mixtures modified by epoxy resin Fat；
(2) 85 DEG C are cooled to, acrylic acid (21 parts) and triphenylphosphine (3 parts) are added into reaction kettle, is stirred under nitrogen atmosphere After mixing reaction 3.5h, sulfur-bearing acrylic acid epoxy resin is prepared；
(3) acrylic resin containing sulfydryl (20 parts), inorganic nano-particle are added in the sulfur-bearing acrylic acid epoxy resin of preparation Sub- TiO2(14 parts) and reactive diluent BAPD (60 parts), after mechanical agitation 1h under the conditions of 20 DEG C, preparing high index of refraction can The UV-cured resin of tune.After testing, which is 1.60, light transmittance 91.1%, photocuring Time is 7s.
Although above-mentioned be described the embodiment of the present invention in conjunction with the embodiments, not the present invention is protected The limitation of scope, those skilled in the art should understand that, on the basis of technical scheme, those skilled in the art The various modifications that can be made or deformation need not be made the creative labor still within protection scope of the present invention.

Claims (10)

  1. A kind of 1. UV-cured resin of high index of refraction, it is characterised in that：It is made of the raw material of following parts by weight：4, 10~30 parts of 4 '-dihydroxy diphenyl sulfide, 100~200 parts of epoxychloropropane, 1~4 part of tetra-n-butyl ammonium bromide, mass fraction For 15%~25% 10~25 parts of lye, 10~35 parts of acrylic acid, 1~5 part of triphenylphosphine, acrylic resin containing sulfydryl 10~ 30 parts, 2~20 parts of inorganic nano-particle titanium dioxide, 40~100 parts of reactive diluent.
  2. 2. the UV-cured resin of high index of refraction according to claim 1, it is characterised in that：The lye is selected from hydrogen-oxygen Change combination more than one or both of sodium water solution, potassium hydroxide aqueous solution.
  3. 3. the UV-cured resin of high index of refraction according to claim 1, it is characterised in that：The reactive diluent choosing Combination more than one or both of siloxanes substituted from methyl acrylate, phenyl.
  4. 4. the UV-cured resin of high index of refraction according to claim 1, it is characterised in that：It is by following parts by weight Made of raw material：4,30 parts of 4 '-dihydroxy diphenyl sulfide, 200 parts of epoxychloropropane, 3 parts of tetra-n-butyl ammonium bromide, potassium hydroxide 20 parts of aqueous solution, 30 parts of acrylic acid, 5 parts of triphenylphosphine, 30 parts of acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide 2 Part, 40 parts of methyl acrylate.
  5. 5. the UV-cured resin of high index of refraction according to claim 1, it is characterised in that：It is by following parts by weight Made of raw material：4,10 parts of 4 '-dihydroxy diphenyl sulfide, 100 parts of epoxychloropropane, 1 part of tetra-n-butyl ammonium bromide, sodium hydroxide 10 parts of aqueous solution, 10 parts of acrylic acid, 1 part of triphenylphosphine, 10 parts of acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide 20 Part, 50 parts of methyl acrylate, 50 parts of the siloxanes of phenyl substitution.
  6. 6. the UV-cured resin of high index of refraction according to claim 1, it is characterised in that：It is by following parts by weight Made of raw material：4,20 parts of 4 '-dihydroxy diphenyl sulfide, 200 parts of epoxychloropropane, 1 part of tetra-n-butyl ammonium bromide, sodium hydroxide 20 parts of aqueous solution, 21 parts of acrylic acid, 3 parts of triphenylphosphine, 20 parts of acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide 14 Part, 60 parts of the siloxanes of phenyl substitution.
  7. 7. according to the UV-cured resin of high index of refraction according to any one of claims 1 to 6, it is characterised in that：It is logical Cross what following methods were prepared：
    (1) 4,4 '-dihydroxy diphenyl sulfide, epoxychloropropane and tetra-n-butyl ammonium bromide are taken, in 90 DEG C~105 DEG C, nitrogen gas 1~1.5h is stirred under the conditions of atmosphere, lye is then added dropwise, 6~7h is reacted, is prepared 4,4 '-dihydroxy diphenyl sulfide asphalt mixtures modified by epoxy resin Fat；
    (2) above-mentioned reaction system is cooled to 80~90 DEG C, adds acrylic acid and triphenylphosphine, and stirring reaction 3 under nitrogen atmosphere~ 4h, is prepared sulfur-bearing acrylic acid epoxy resin；
    (3) acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide and activity are added into sulfur-bearing acrylic acid epoxy resin Diluent, mechanical agitation 1h, is prepared UV-cured resin under the conditions of 20~35 DEG C.
  8. 8. the preparation method of the UV-cured resin of high index of refraction according to any one of claims 1 to 7, its feature exists In：Comprise the following steps：
    (1) 4,4 '-dihydroxy diphenyl sulfide, epoxychloropropane and tetra-n-butyl ammonium bromide are taken, in 90 DEG C~105 DEG C, nitrogen gas 1~1.5h is stirred under the conditions of atmosphere, lye is then added dropwise, 6~7h is reacted, is prepared 4,4 '-dihydroxy diphenyl sulfide asphalt mixtures modified by epoxy resin Fat；
    (2) above-mentioned reaction system is cooled to 80~90 DEG C, adds acrylic acid and triphenylphosphine, and stirring reaction 3 under nitrogen atmosphere~ 4h, is prepared sulfur-bearing acrylic acid epoxy resin；
    (3) acrylic resin containing sulfydryl, inorganic nano-particle titanium dioxide and activity are added into sulfur-bearing acrylic acid epoxy resin Diluent, mechanical agitation 1h, is prepared UV-cured resin under the conditions of 20~35 DEG C.
  9. 9. the UV-cured resin of high index of refraction according to any one of claims 1 to 7 is preparing the bright room contrast of raising Application in functional membrane.
  10. 10. application according to claim 9, it is characterised in that：As the micro- knot of optics for improving bright room contrast functional membrane The material of structure absorbed layer is applied.
CN201711076924.XA 2017-11-06 2017-11-06 A kind of UV-cured resin of high index of refraction and preparation method thereof Pending CN108003567A (en)

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110804129A (en) * 2019-11-15 2020-02-18 江南大学 Preparation method of high-refractive-index optical material with ultraviolet shielding effect
CN111217987A (en) * 2020-01-08 2020-06-02 广东莱尔新材料科技股份有限公司 High-refractive-index UV resin, preparation method thereof and application of nano-imprinting
CN117447921A (en) * 2023-10-26 2024-01-26 东莞市诺尔斯有机硅科技有限公司 High refractive index optical organic glue composition and preparation method thereof

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110804129A (en) * 2019-11-15 2020-02-18 江南大学 Preparation method of high-refractive-index optical material with ultraviolet shielding effect
CN110804129B (en) * 2019-11-15 2021-04-02 江南大学 Preparation method of high-refractive-index optical material with ultraviolet shielding effect
CN111217987A (en) * 2020-01-08 2020-06-02 广东莱尔新材料科技股份有限公司 High-refractive-index UV resin, preparation method thereof and application of nano-imprinting
CN117447921A (en) * 2023-10-26 2024-01-26 东莞市诺尔斯有机硅科技有限公司 High refractive index optical organic glue composition and preparation method thereof

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