CN108484821B - High-refractive-index acrylate copolymer and preparation method thereof - Google Patents
High-refractive-index acrylate copolymer and preparation method thereof Download PDFInfo
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- CN108484821B CN108484821B CN201810175501.1A CN201810175501A CN108484821B CN 108484821 B CN108484821 B CN 108484821B CN 201810175501 A CN201810175501 A CN 201810175501A CN 108484821 B CN108484821 B CN 108484821B
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
- C08F220/02—Monocarboxylic acids having less than ten carbon atoms; Derivatives thereof
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- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F220/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride ester, amide, imide or nitrile thereof
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- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
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Abstract
The invention provides a high-refractive-index acrylate copolymer (I), which is prepared by copolymerizing benzyl alcohol acrylate and a hydroxyl-containing acrylate monomer (II) to form a copolymer with a structural formula, and polymerizing the copolymer with (methyl) isocyanate ethyl acrylate (III).
Description
Technical Field
The invention relates to the technical field of optical film materials, in particular to a high-refractive-index acrylate copolymer and a preparation method thereof.
Background
Optical materials are a class of materials with optical properties and functions, which are mainly classified into organic and inorganic materials. Compared with inorganic materials, organic polymers are more and more focused and widely used because of their properties such as light weight, easy molding and processing, and excellent optical properties.
Polyurethane-based optical resins are an important development direction for new optical resins in recent years because polyurethane materials have the advantages of impact resistance, high transmittance, wear resistance, and the like. Such resins have a small relative density, impact strength and a higher refractive index than vinyl optical resins. In terms of improving the refractive index of the resin material for an optical film, benzene rings have high susceptibility, but the single benzene ring has a limited range of improving the refractive index, and researchers often select a monomer containing a fluorene structure or introduce halogen and sulfur elements into a molecular chain.
At present, the method for improving the refractive index of the optical resin mainly introduces halogen and sulfur elements into the molecular structure of the resin or adds inorganic particles with high refractive index. The halogen introduced into the molecular chain can improve the refractive index of the optical resin, but after the optical resin is used for a period of time, the halogen atoms in the resin not only can corrode the surface of the optical material, but also has instability to light, and easily causes the defects of aging, discoloration and the like of the resin. The inorganic high-refractive-index particles are added into the optical material, so that although the refractive index of the optical resin is improved, on one hand, the production operation time is long, the production efficiency is reduced, and on the other hand, the compatibility stability of the inorganic high-refractive-index particles and the resin is poor, so that the defect that the inorganic high-refractive-index particles and the resin are easy to peel off is caused.
Disclosure of Invention
In view of the above, the technical problem to be solved by the present invention is to provide a high refractive index acrylate copolymer and a preparation method thereof, and the preparation method of the high refractive index acrylate copolymer provided by the present invention has the advantages of low production cost, convenient post production operation, excellent chemical and physical stability, and storage resistance.
A high refractive index acrylate copolymer (I) is prepared by copolymerizing benzyl alcohol acrylate and a hydroxyl-containing acrylate monomer (II) to form a copolymer with a structural formula, and then polymerizing the copolymer with (methyl) isocyanate ethyl acrylate (III), wherein the structural formula is as follows:
wherein the value of n1+ n2 in the formula I is 2-25;
n has a value of 1 to 5;
ra, Rb and Rc are hydrogen or methyl.
Further, the hydroxyl group-containing acrylate monomer (II) is selected from hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate.
Further, the contents of biphenyl methyl acrylate (BPMA), a hydroxyl-containing acrylate monomer (II) and (methyl) isocyanate ethyl acrylate (III) are respectively a mol, b mol and c mol, wherein a, b and c are (4.391-0.7318) to 1: 1.
Further, the high refractive index acrylate copolymer (I) has a refractive index of not less than 1.5.
A preparation method of a high-refractive-index acrylate copolymer comprises the following two steps: firstly, dripping a mixture of a hydroxyl-containing acrylate monomer (II), an initiator and a polymerization inhibitor into a biphenyl methyl methacrylate (BPMA) solution, controlling the reaction temperature and time, and polymerizing to obtain an intermediate copolymer (IV); secondly, dropwise adding the mixed solution of (methyl) isocyanate ethyl acrylate (III) and a catalyst into the intermediate copolymer with the structural formula (IV) for polymerization, controlling the reaction temperature and the reaction time, and finally polymerizing to obtain the copolymer (I) with the required structure
Further, firstly, dripping a mixture of a hydroxyl-containing acrylate monomer (II), an initiator and a polymerization inhibitor into a biphenyl methanol acrylate solution for 30-40 min at the reaction temperature of 100-120 ℃ for 6-8 h; and secondly, dropwise adding the mixed liquid of the (methyl) isocyanate ethyl acrylate and the catalyst into the intermediate copolymer (IV), wherein the dropwise adding time is 30-40 min, the polymerization reaction temperature range is 80-90 ℃, and the reaction time is 4-6 h.
Further, the mass of the initiator is 0.5-5.0 percent of the total mass of the biphenyl methyl acrylate (BPMA) and the acrylate monomer (II) containing hydroxyl; the monthly mass of the catalyst is (1.0-5.0)% of the total mass of biphenyl methyl acrylate (BPMA), the hydroxyl-containing acrylate monomer (II) and the (methyl) isocyanate ethyl acrylate (III).
Further, the mass of the initiator used was 1.0% of the total mass of biphenyl methyl acrylate (BPMA) and hydroxyl group-containing acrylate monomer (II); the catalyst used in the second step is 2.5 per mill of the total mass of biphenyl methyl acrylate (BPMA), acrylate monomer (II) containing hydroxyl and (methyl) isocyanate ethyl acrylate (III).
Further, the initiator is a peroxide, preferably Benzoyl Peroxide (BPO);
further, the catalyst is organic tin or organic bismuth, and is preferably bismuth laurate.
Compared with the prior art, the invention provides the high-refractive-index acrylate copolymer and the preparation method thereof, and biphenyl methyl methacrylate (BPMA) modified polyurethane resin is adopted, so that the copolymer has the advantages of high breaking rate, high wear resistance, low shrinkage rate and the like. The copolymer prepared by the method has higher functionality than that of a common light-cured monomer, and the later-stage curing effect is improved; on the other hand, copolymerization results in a long main chain, which causes the chain segment to grow and become flexible. The theoretical shrinkage rate of the conventional difunctional polyurethane is 12.92%, the theoretical shrinkage rate of the conventional difunctional polyurethane is about 5%, the theoretical maximum shrinkage rate of the hexafunctional polyurethane is about 21.76%, and the theoretical maximum shrinkage rate of the copolymer in the patent is 0.004410%, so that after the copolymer is cured into a film, the shrinkage rate of the film is effectively reduced, and the warpage of the film after the film is coated is further reduced.
Drawings
FIG. 1 is an infrared spectrum of a high refractive index acrylate copolymer of the present invention.
Detailed Description
The invention provides a high-refractive-index acrylate copolymer, which has a characteristic structural formula shown as the following formula I:
in formula I, n1+ n2 has a value of 2-25, n has a value of 1-5, and Ra, Rb and Rc are hydrogen or methyl. The polymer is prepared by copolymerizing benzyl alcohol acrylate (BPMA) and a hydroxyl-containing acrylate monomer (II) to form a copolymer with a structural formula, and then polymerizing the copolymer with (methyl) isocyanate ethyl acrylate (III). Wherein the hydroxyl group-containing acrylate monomer (II) includes, but is not limited to: hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, 2-hydroxypropyl (meth) acrylate, and the like. Such as:
the high-refractive-index characteristic of the (methyl) isocyanate ethyl acrylate (III) is determined by the material proportion of biphenyl methyl methacrylate (BPMA), hydroxyl-containing acrylate monomer (II) and (methyl) isocyanate ethyl acrylate (III), the molar weight of the (methyl) isocyanate ethyl acrylate (III) determines the high-refractive-index characteristic of the polymer, and the molar weight of the (methyl) isocyanate ethyl acrylate (III) is a mol, b mol and c mol, wherein a, b and c are (4.391-0.7318) to 1: 1. The copolymer (I) has excellent performances of high refractive index, high transparency and the like due to a skeleton structure formed by copolymerizing biphenyl methyl acrylate and a hydroxyl-containing acrylate monomer (II), and the copolymer (I) has a double bond capable of absorbing light and polymerizing due to the introduction of a structure of (methyl) isocyanate ethyl acrylate (III) containing a carbon-carbon double bond; and the refractive index of the resulting copolymer (I) is not less than 1.5.
The invention discloses a preparation method of the polymer, biphenyl methyl acrylate (BPMA) and hydroxyl-containing acrylate monomer (II) are firstly copolymerized into copolymer (IV), and the copolymer (IV) is polymerized with (methyl) isocyanate ethyl acrylate (III) to obtain copolymer (I), wherein the structures of the biphenyl methyl acrylate (BPMA), the (methyl) isocyanate ethyl acrylate (III) and the copolymer (IV) are
In another preferred embodiment of the present invention, biphenyl methyl acrylate (BPMA) and hydroxyl-containing acrylate monomer (II) are copolymerized to form a copolymer with a structural formula (IV), and then polymerized with (methyl) isocyanate ethyl acrylate (III) to obtain a copolymer with a high refractive index and a structural formula (I), wherein the specific embodiment comprises two steps: firstly, dripping a mixture of a hydroxyl-containing acrylate monomer, an initiator and a polymerization inhibitor into a biphenyl methanol acrylate solution for 30-40 min at a reaction temperature of 100-120 ℃ for 6-8 h; and secondly, dropwise adding the mixed liquid of the (methyl) isocyanate ethyl acrylate and the catalyst into the intermediate copolymer (IV), wherein the dropwise adding time is 30-40 min, the polymerization reaction temperature range is 80-90 ℃, and the reaction time is 4-6 h. The copolymer has good optical properties.
In another preferred embodiment of the present invention, in the first step, a mixture of a hydroxyl-containing acrylate monomer (ii), an initiator and a polymerization inhibitor is added dropwise to a biphenyl methyl methacrylate (BPMA) solution to polymerize an intermediate copolymer having a structural formula (iv); the initiator is peroxide, preferably Benzoyl Peroxide (BPO), and the BPO has short half-life and little residue after reaction, so that the BPO is selected, on one hand, the half-life is short, and on the other hand, BPO residue contains benzene rings and is left on a main chain to improve the refractive index; the mass of the initiator such as BPO is 0.5-5.0% of the total mass of the biphenyl methyl acrylate (BPMA) and the hydroxyl acrylate monomer (II), and the initiator is preferably 1.0%. And secondly, dropwise adding the mixed solution of (methyl) isocyanate ethyl acrylate and a catalyst into the intermediate copolymer (IV) for polymerization, controlling the reaction temperature and time, and finally polymerizing to obtain the copolymer with the required structural formula (I), wherein the catalyst is organic tin or organic bismuth, preferably bismuth laurate, and the mass of the used catalyst, such as the bismuth laurate, is (1.0-5.0)% thousandth, preferably 2.5% thousandth of the total mass of biphenyl methanol acrylate (BPMA) and hydroxyl acrylate monomer (II) and (methyl) isocyanate ethyl acrylate (III).
Example 1:
the specific scheme of the invention is as follows: the preparation method of the acrylate copolymer with high refractive index comprises the following steps:
A. in the first step, a mixture of 200.00g of hydroxyethyl acrylate, 10.00g of an initiator and 0.50g of a polymerization inhibitor was added dropwise to 800.00g of a biphenyl methyl acrylate solution.
B. And (3) raising the temperature to 80 ℃, slowly dripping the mixed solution for 30-40 min, raising the temperature to 100-120 ℃ after dripping, and keeping the temperature for 6-8 h to obtain the product which is the copolymer of the intermediate structural formula (IV).
C. After the first-step polymerization reaction is finished, the temperature is reduced to 80 ℃, and 243.06g of (methyl) isocyanate ethyl acrylate and 3.10g of catalyst organic bismuth are slowly dropped into the system.
D. After the dropwise addition is finished, the temperature is controlled to be 80-90 ℃, and the reaction time is 4-6 hours, so that the copolymer with the high-refractive-index acrylate structural formula (I) is obtained.
E. The target product has a refractive index of 1.5473(65 ℃ C.) and a viscosity of 2500cps (65 ℃ C.).
Example 2:
the specific scheme of the invention is as follows: the preparation method of the acrylate copolymer with high refractive index comprises the following steps:
A. in the first step, a mixture of 58.06g of hydroxyethyl acrylate, 33.87g of initiator and 0.56g of inhibitor was added dropwise to 1071.00g of a solution of biphenyl methanol acrylate.
B. And (3) raising the temperature to 80 ℃, slowly dripping the mixed solution for 30-40 min, raising the temperature to 100-120 ℃ after dripping, and keeping the temperature for 6-8 h to obtain the product which is the copolymer of the intermediate structural formula (IV).
C. After the first-step polymerization reaction is finished, the temperature is reduced to 80 ℃, and mixed solution of 70.56g of (methyl) isocyanate ethyl acrylate and 3.00g of catalyst organic bismuth is slowly dripped into the system.
D. After the dropwise addition is finished, the temperature is controlled to be 80-90 ℃, and the reaction time is 4-6 hours, so that the copolymer with the high-refractive-index acrylate structural formula (I) is obtained.
E. The target product has a refractive index of 1.6129(65 deg.C) and a viscosity of 4300cps (65 deg.C).
The performance index test was performed on the products obtained in example 1 and example 2, as shown in table 1.
TABLE 1 Performance index of the copolymers provided in the examples of the invention
In addition, the high refractive index copolymer obtained by the invention has an infrared spectrogram as shown in figure 1.
The above description of the embodiments is only intended to facilitate the understanding of the method of the invention and its core idea. It should be noted that, for those skilled in the art, it is possible to make various improvements and modifications to the present invention without departing from the principle of the present invention, and those improvements and modifications also fall within the scope of the claims of the present invention.
Claims (12)
1. A high-refractivity acrylate copolymer (I) is prepared from biphenyl methanol acrylate and hydroxyl acrylate monomer (II) through copolymerizing to obtain copolymer, and polymerizing with (methyl) isocyanate ethyl acrylate (III)
Wherein n in the formula I1+n2Has a value of 2 to 25;
n has a value of 1 to 5;
ra, Rb and Rc are hydrogen or methyl.
2. The acrylate copolymer (I) having a high refractive index according to claim 1, wherein the hydroxyl group-containing acrylate monomer (II) is selected from the group consisting of hydroxyethyl (meth) acrylate, hydroxypropyl (meth) acrylate, and 2-hydroxypropyl (meth) acrylate.
3. The high refractive index acrylate copolymer (I) according to claim 1, wherein the contents of biphenyl carbinol acrylate (BPMA), the hydroxyl group-containing acrylate monomer (II) and the (meth) isocyanate ethyl acrylate (III) are respectively a mol, b mol and c mol, wherein a, b and c are (4.391-0.7318) to 1: 1.
4. The high refractive index acrylate copolymer (I) according to claim 1, wherein the refractive index of the high refractive index acrylate copolymer (I) is not less than 1.5.
5. The preparation method of the high-refractive-index acrylate copolymer is characterized by comprising the following two steps of: firstly, dripping a mixture of acrylate monomer (II) containing hydroxyl, initiator and polymerization inhibitor into a biphenyl methanol acrylate BPMA solution, controlling the reaction temperature and time, and polymerizing to obtain an intermediate copolymer (IV), wherein the structural formula of the intermediate copolymer (IV) is shown in the specification
And secondly, dropwise adding the mixed solution of (methyl) isocyanate ethyl acrylate (III) and a catalyst into the intermediate copolymer with the structural formula (IV) for polymerization, controlling the reaction temperature and time, and finally polymerizing to obtain the copolymer (I) with the required structure.
6. The method for preparing a high refractive index acrylate copolymer according to claim 5, comprising: firstly, dripping a mixture of a hydroxyl-containing acrylate monomer (II), an initiator and a polymerization inhibitor into a biphenyl methanol acrylate solution for 30-40 min at a reaction temperature of 100-120 ℃ for 6-8 h; and secondly, dropwise adding the mixed liquid of the (methyl) isocyanate ethyl acrylate and the catalyst into the intermediate copolymer (IV), wherein the dropwise adding time is 30-40 min, the polymerization reaction temperature range is 80-90 ℃, and the reaction time is 4-6 h.
7. The method for preparing an acrylate copolymer having a high refractive index according to claim 5, wherein the mass of the initiator used is (0.5 to 5.0)% of the total mass of the biphenyl methanol acrylate BPMA and the hydroxyl group-containing acrylate monomer (II); the mass of the catalyst is 1.0-5.0 permillage of the total mass of the biphenyl methanol acrylate BPMA, the hydroxyl-containing acrylate monomer (II) and the (methyl) isocyanate ethyl acrylate (III).
8. The method for preparing a high refractive index acrylate copolymer according to claim 5, wherein the mass of the initiator is 1.0% of the total mass of the biphenyl methacrylate BPMA and the hydroxyl group-containing acrylate monomer (II); the mass of the catalyst used in the second step is 2.5 per mill of the total mass of the biphenyl methanol acrylate BPMA, the acrylate monomer (II) containing hydroxyl and the (methyl) isocyanate ethyl acrylate (III).
9. The method for preparing a high refractive index acrylate copolymer according to claim 5, wherein the initiator is a peroxide.
10. The method for preparing a high refractive index acrylate copolymer according to claim 9, wherein the initiator is Benzoyl Peroxide (BPO).
11. The method for preparing the acrylate copolymer with high refractive index according to claim 5, wherein the catalyst is organotin or organobismuth.
12. The method for preparing a high refractive index acrylate copolymer according to claim 11, wherein the catalyst is bismuth laurate.
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| CN109438672A (en) * | 2018-09-29 | 2019-03-08 | 张家港康得新光电材料有限公司 | Urethane acrylate and preparation method thereof |
| CN109810134A (en) * | 2018-12-29 | 2019-05-28 | 张家港康得新光电材料有限公司 | High refractive index flame retardant type UV resin, preparation method and optical film |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1234408A (en) * | 1999-05-14 | 1999-11-10 | 上海交通大学 | Transparent polymer material and preparation method thereof |
| JP2000075103A (en) * | 1998-08-27 | 2000-03-14 | Seizaburo Sakakibara | Production of resin for lens having high refractive index, high impact resistance and good dyeability |
| CN1252136A (en) * | 1997-02-13 | 2000-05-03 | Dsm有限公司 | Photocurable resin composition |
| JP2009155322A (en) * | 2007-12-03 | 2009-07-16 | Osaka Organic Chem Ind Ltd | Aromatic ring-containing monomer composition and polymer based thereon |
| CN101508875A (en) * | 2008-02-15 | 2009-08-19 | 日东电工株式会社 | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| EP2586802A1 (en) * | 2011-05-18 | 2013-05-01 | DIC Corporation | Radically polymerizable composition, cured product and plastic lens |
| CN103467706A (en) * | 2013-09-26 | 2013-12-25 | 烟台德邦科技有限公司 | Preparation method of high-UV activity polyurethane acrylate |
| KR20140141532A (en) * | 2013-05-31 | 2014-12-10 | 주식회사 엘지화학 | Light-scattering adhesive film, polarizing plate and liquid crystal display device |
-
2018
- 2018-03-02 CN CN201810175501.1A patent/CN108484821B/en active Active
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| CN1252136A (en) * | 1997-02-13 | 2000-05-03 | Dsm有限公司 | Photocurable resin composition |
| JP2000075103A (en) * | 1998-08-27 | 2000-03-14 | Seizaburo Sakakibara | Production of resin for lens having high refractive index, high impact resistance and good dyeability |
| CN1234408A (en) * | 1999-05-14 | 1999-11-10 | 上海交通大学 | Transparent polymer material and preparation method thereof |
| JP2009155322A (en) * | 2007-12-03 | 2009-07-16 | Osaka Organic Chem Ind Ltd | Aromatic ring-containing monomer composition and polymer based thereon |
| CN101508875A (en) * | 2008-02-15 | 2009-08-19 | 日东电工株式会社 | Pressure-sensitive adhesive composition for optical films, pressure-sensitive adhesive optical film and image display |
| EP2586802A1 (en) * | 2011-05-18 | 2013-05-01 | DIC Corporation | Radically polymerizable composition, cured product and plastic lens |
| KR20140141532A (en) * | 2013-05-31 | 2014-12-10 | 주식회사 엘지화학 | Light-scattering adhesive film, polarizing plate and liquid crystal display device |
| CN103467706A (en) * | 2013-09-26 | 2013-12-25 | 烟台德邦科技有限公司 | Preparation method of high-UV activity polyurethane acrylate |
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