CN108484821A - A kind of high refractive index acrylate copolymer and preparation method thereof - Google Patents
A kind of high refractive index acrylate copolymer and preparation method thereof Download PDFInfo
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- CN108484821A CN108484821A CN201810175501.1A CN201810175501A CN108484821A CN 108484821 A CN108484821 A CN 108484821A CN 201810175501 A CN201810175501 A CN 201810175501A CN 108484821 A CN108484821 A CN 108484821A
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- acrylate
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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
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- 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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- 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
- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
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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
- 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
- C08F220/10—Esters
- C08F220/12—Esters of monohydric alcohols or phenols
- C08F220/16—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms
- C08F220/18—Esters of monohydric alcohols or phenols of phenols or of alcohols containing two or more carbon atoms with acrylic or methacrylic acids
- C08F220/1818—C13or longer chain (meth)acrylate, e.g. stearyl (meth)acrylate
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- Chemical Kinetics & Catalysis (AREA)
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- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
The present invention provides a kind of high refractive index acrylate copolymers (I), it is copolymer by the first copolymerization structural formula of the acrylate monomer (II) of Acrylate benzyl alcohol ester and hydroxyl, it polymerize again with (methyl) isocyanates ethyl acrylate (III) and is made, high refractive index acrylate copolymer preparation method production cost provided by the invention is low, later stage production operation is convenient, and with excellent chemically and physically stability, shelf-stable.
Description
Technical field
The present invention relates to optical film material technical field more particularly to a kind of high refractive index acrylate copolymer and its systems
Preparation Method.
Background technology
Optical material is a kind of material with optical property and function, is broadly divided into organic and inorganic two major classes.With nothing
Machine class material is compared, more and more since organic polymer has light, easily molded processing, the excellent performances such as optical
Attract attention and extensive use.
Since polyurethane material has many advantages, such as that shock resistance, transmitance are high, wear-resisting, polyurethane-type optical resin is close
The important development direction of Novel optical resin over year.Compared with alkenes optical resin, this resinoid is small with relative density, impacts
Intensity and higher refractive index.In terms of the refractive index for improving optical film resin material, phenyl ring has the easily property changed, but single benzene
Ring improves refractive index limited extent, and researcher often selects to introduce halogen and sulphur member containing fluorene structured monomer or into strand
Element.
The method for improving optical resin refractive index at present mainly introduced into resinous molecular structure halogen and element sulphur or
The inorganic particle of high refractive index is added in person.Halogen is introduced in strand can improve the refractive index of optical resin, but use one section
When after will appear in its resin halogen atom can not only corrode optical material surface, while there is unstability to light, hold
The defects of easily causing the weather stain of resin.Inorganic high refractive index particle is added in optical material, although improving optical resin
Refractive index, but one side production operation is of long duration, reduces production efficiency, on the other hand inorganic high refractive index particle and resin
Compatible stability is poor, be easy to cause the defect of the two stripping.
Invention content
In view of this, technical problem to be solved by the present invention lies in provide a kind of high refractive index acrylate copolymer and
Preparation method, high refractive index acrylate copolymer preparation method production cost provided by the invention is low, later stage production operation
It is convenient, and with excellent chemically and physically stability, shelf-stable.
A kind of high refractive index acrylate copolymer (I), by the acrylate monomer of Acrylate benzyl alcohol ester and hydroxyl
(II) first copolymerization structural formula is copolymer, then polymerize with (methyl) isocyanates ethyl acrylate (III) and be made,
Structural formula is：
Wherein, the value of n1+n2 is 2-25 in Formulas I；
The value of n is 1-5；
Ra, Rb and Rc are hydrogen or methyl.
Further, the acrylate monomer (II) of the hydroxyl is selected from (methyl) hydroxy-ethyl acrylate, (methyl) third
Olefin(e) acid hydroxypropyl acrylate, (methyl) acrylic acid 2- hydroxy propyl esters.
Further, acrylate monomer (II) and (methyl) isocyanide of biphenylmethanol acrylate (BPMA), hydroxyl
Acid esters ethyl acrylate (III) content is respectively a moles, b moles and c moles, wherein a:b:C is (4.391~0.7318):
1:1。
Further, the refractive index of the high refractive index acrylate copolymer (I) is not less than 1.5.
A kind of preparation method of high refractive index acrylate copolymer, including following two step：The first step is by hydroxyl
The mixed liquor of acrylate monomer (II), initiator and polymerization inhibitor is added drop-wise in biphenylmethanol acrylate (BPMA) solution, control
Reaction temperature and time are made, polymerization obtains intermediary copolymer (IV)；Second step is by (methyl) isocyanates ethyl acrylate
(III) it is to polymerize in (IV) intermediary copolymer that structural formula is added drop-wise to catalyst mixed liquid, controls reaction temperature and time, most
Final polymerization and the copolymer (I) for obtaining required structure
Further, the mixed liquor of the acrylate monomer (II) of hydroxyl, initiator and polymerization inhibitor is added dropwise the first step
Into biphenylmethanol acrylate solution, time for adding is 30min~40min, and range of reaction temperature is 100~120 DEG C, instead
It is 6~8h between seasonable；(methyl) isocyanates ethyl acrylate and catalyst mixed liquid are added drop-wise to intermediary copolymer by second step
(IV) in, time for adding is 30min~40min, and ranging from 80~90 DEG C of polymeric reaction temperature, the reaction time is 4~6h.
Further, the quality of initiator used is the acrylate list of biphenylmethanol acrylate (BPMA) and hydroxyl
(0.5~5.0) % of the gross mass of body (II)；The catalyst moon quality is biphenylmethanol acrylate (BPMA), hydroxyl
Acrylate monomer (II) and (methyl) isocyanates ethyl acrylate (III) gross mass (1.0~5.0) ‰.
Further, the quality of initiator used is the acrylate list of biphenylmethanol acrylate (BPMA) and hydroxyl
The 1.0% of the gross mass of body (II)；Second step used catalyst is that quality is biphenylmethanol acrylate (BPMA), hydroxyl
The 2.5 ‰ of the gross mass of acrylate monomer (II) and (methyl) isocyanates ethyl acrylate (III).
Further, the initiator is peroxide, preferably benzoyl peroxide (BPO)；
Further, the catalyst is organotin or organo-bismuth class, preferably lauric acid bismuth.
Compared with prior art, the present invention provides a kind of high refractive index acrylate copolymers and its preparation to use biphenyl
Methanol acrylate (BPMA) modified polyurethane resin so that copolymer has high refractivity, while having high wearability, low receipts
The advantages that shrinkage.On the one hand copolymer prepared by this method has higher degree of functionality, after improving than general photo-curing monomer
The solidification effect of phase；Another aspect combined polymerization obtains long main chain so that segment increases, and becomes more flexible.Conventional two officials are poly-
Urethane theory shrinking percentage is 12.92%, and general shrinking percentage is in 5% or so, six official's polyurethane theoretical maximum shrinking percentage 21.76%
Or so, the theoretical maximum shrinking percentage of copolymer is 0.004410% in this patent, after promoting film-forming, significantly reduces film
Degree of shrinkage, and then reduce the warpage after film.
Description of the drawings
Fig. 1 is the infrared spectrogram of high refractive index acrylate copolymer of the present invention.
Specific implementation mode
The present invention provides a kind of high refractive index acrylate copolymer, the feature structure formula such as following formula I institutes of the compound
Show：
The value of n1+n2 is 2-25 in Formulas I, and the value of n is 1-5, and Ra, Rb and Rc are hydrogen or methyl.The polymer passes through benzene first
The first copolymerization structural formula of the acrylate monomer (II) of alcohol acrylate (BPMA) and hydroxyl is copolymer, then with (methyl)
Isocyanates ethyl acrylate (III) polymerize and is made.The acrylate monomer (II) of the wherein described hydroxyl, including but not only
It is limited to：(methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid 2- hydroxy propyl esters etc..Such as：
Wherein the feature of (methyl) isocyanates ethyl acrylate (III) its high refractive index depends on biphenylmethanol acrylic acid
Ester (BPMA) is determined with the acrylate monomer (II) of hydroxyl and the material proportion of (methyl) isocyanates ethyl acrylate (III)
The high refractive index feature of the polymer is determined, mole is respectively a moles, b moles and c moles, wherein a:b:C is (4.391
~0.7318):1:1.Since this copolymer (I) has the acrylate monomer (II) of biphenylmethanol acrylate and hydroxyl
The skeleton structure being copolymerized into has high refractive index, the high excellent properties of the transparency, while (methyl) that introduces carbon-carbon double bonds is different
The structure of cyanate ethyl acrylate (III) make in copolymer (I) structure have can extinction polymerization double bond；And gained is copolymerized
The refractive index of object (I) is not less than 1.5.
The invention discloses the preparation methods of the polymer, with the propylene of biphenylmethanol acrylate (BPMA) and hydroxyl
Acid ester monomer (II) is first copolymerized into copolymer (IV), and copolymer (IV) polymerize with (methyl) isocyanates ethyl acrylate (III) again
And copolymer (I) is obtained, wherein biphenylmethanol acrylate (BPMA), (methyl) isocyanates ethyl acrylate (III) and copolymerization
The structure of object (IV) is
, copolymer (I) obtained feature with a high refractive index, specific embodiment is divided into two steps：The first step, by hydroxyl
The mixed liquor of acrylate monomer (II), initiator and polymerization inhibitor is added drop-wise in biphenylmethanol acrylate solution, and polymerization obtains
Structural formula is (IV) intermediary copolymer；During (methyl) isocyanates ethyl acrylate and catalyst mixed liquid are added drop-wise to by second step
Between polymerization in copolymer (IV), control reaction temperature and time, final polymerization obtains the copolymerization that required structural formula is (I)
Object.
Another preferred embodiment of the present invention, with the acrylate monomer of biphenylmethanol acrylate (BPMA) and hydroxyl
(II) first copolymerization structural formula is (IV) copolymer, then polymerize with (methyl) isocyanates ethyl acrylate (III) and had
It is the copolymer of (I) to have high index structure formula, and specific embodiment is divided into two steps：The first step is by the acrylic acid of hydroxyl
The mixed liquor of ester monomer, initiator and polymerization inhibitor is added drop-wise in biphenylmethanol acrylate solution, time for adding be 30min~
40min, range of reaction temperature are 100~120 DEG C, and the reaction time is 6~8h；Second step is by (methyl) isocyanates acrylic acid second
Ester is added drop-wise to catalyst mixed liquid in intermediary copolymer (IV), and time for adding is 30min~40min, polymeric reaction temperature
Ranging from 80~90 DEG C, the reaction time is 4~6h.The copolymer has good optical property.
Another preferred embodiment of the present invention, the first step, by acrylate monomer (II), initiator and the polymerization inhibitor of hydroxyl
Mixed liquor be added drop-wise in biphenylmethanol acrylate (BPMA) solution, polymerization obtain structural formula be (IV) intermediary copolymer；Institute
It is peroxide to state initiator, preferably benzoyl peroxide (BPO), due to the general half-life short of peroxidating class initiator,
Less residue after reaction selects BPO, and one side half-life short, another aspect BPO relics contain phenyl ring, and staying on main chain can be with
Improve refractive index；The quality of initiator used such as BPO is the acrylate monomer of biphenylmethanol acrylate (BPMA) and hydroxyl
(II) (0.5~5.0) % of gross mass, preferably 1.0%.Second step is by (methyl) isocyanates ethyl acrylate and is catalyzed
Agent mixed liquor is added drop-wise to polymerization in intermediary copolymer (IV), controls reaction temperature and time, and final polymerization obtains required knot
Structure formula is the copolymer of (I), and the catalyst is organotin or organo-bismuth class, preferably lauric acid bismuth, matter used catalyst
Such as acrylate monomer (II), (methyl) isocyanates that lauric acid bismuth quality is biphenylmethanol acrylate (BPMA) and hydroxyl
(1.0~5.0) ‰ of the gross mass of ethyl acrylate (III), preferably 2.5 ‰.
Embodiment 1：
The present invention concrete scheme be：Containing a kind of preparation method of high refractive index acrylate copolymer, including walk as follows
Suddenly：
A. the mixed liquor of hydroxy-ethyl acrylate 200.00g, initiator 10.00g and polymerization inhibitor 0.50g are added drop-wise to by the first step
In biphenylmethanol acrylate 800.00g solution.
B. temperature rises to 80 DEG C, is slowly added dropwise mixed liquor, when dropwise addition a length of 30min~40min, be warming up to after completion of dropwise addition
100~120 DEG C, the insulation reaction time is 6~8h, and products therefrom is the copolymer of intermediate structure formula (IV).
C. 80 DEG C are cooled to after first step polymerisation, (methyl) isocyanates third is slowly added dropwise into the system
Olefin(e) acid ethyl ester 243.06g and catalyst organo-bismuth 3.10g mixed liquors.
D. after completion of dropwise addition, control temperature range is 80~90 DEG C, and the reaction time is 4~6h to get high refractive index propylene
Acrylate structure formula is the copolymer of (I).
E. target product refractive index is 1.5473 (65 DEG C), and viscosity is 2500cps (65 DEG C).
Embodiment 2：
The present invention concrete scheme be：Containing a kind of preparation method of high refractive index acrylate copolymer, including walk as follows
Suddenly：
A. the mixed liquor of hydroxy-ethyl acrylate 58.06g, initiator 33.87g and polymerization inhibitor 0.56g are added drop-wise to by the first step
In biphenylmethanol acrylate 1071.00g solution.
B. temperature rises to 80 DEG C, is slowly added dropwise mixed liquor, when dropwise addition a length of 30min~40min, be warming up to after completion of dropwise addition
100~120 DEG C, the insulation reaction time is 6~8h, and products therefrom is the copolymer of intermediate structure formula (IV).
C. 80 DEG C are cooled to after first step polymerisation, (methyl) isocyanates third is slowly added dropwise into the system
Olefin(e) acid ethyl ester 70.56g and catalyst organo-bismuth 3.00g mixed liquors.
D. after completion of dropwise addition, control temperature range is 80~90 DEG C, and the reaction time is 4~6h to get high refractive index propylene
Acrylate structure formula is the copolymer of (I).
E. target product refractive index is 1.6129 (65 DEG C), and viscosity is 4300cps (65 DEG C).
Testing performance index is carried out to embodiment 1,2 obtained product of embodiment, as shown in table 1.
The performance indicator of 1 copolymer provided in an embodiment of the present invention of table
In addition, the high refractive index copolymers infrared spectrogram that the present invention obtains is as shown in Figure 1.
The explanation of above example is only intended to facilitate the understanding of the method and its core concept of the invention.It should be pointed out that pair
For those skilled in the art, without departing from the principle of the present invention, the present invention can also be carried out
Some improvements and modifications, these improvement and modification also fall into the protection domain of the claims in the present invention.
Claims (10)
1. a kind of high refractive index acrylate copolymer (I), by the acrylate monomer of Acrylate benzyl alcohol ester and hydroxyl
(II) first copolymerization structural formula is copolymer, then polymerize with (methyl) isocyanates ethyl acrylate (III) and be made, and is tied
Structure formula is
Wherein, n in Formulas I1The value of+n2 is 2-25；
The value of n is 1-5；
Ra, Rb and Rc are hydrogen or methyl.
2. a kind of high refractive index acrylate copolymer (I) according to claim 1, which is characterized in that the hydroxyl
Acrylate monomer (II) is selected from (methyl) hydroxy-ethyl acrylate, (methyl) hydroxypropyl acrylate, (methyl) acrylic acid 2- hydroxyls
Propyl ester.
3. high refractive index acrylate copolymer (I) according to claim 1, which is characterized in that Acrylate benzyl alcohol ester
BPMA, the acrylate monomer (II) of hydroxyl and (methyl) isocyanates ethyl acrylate (III) content are respectively a moles, b
Mole and c moles, wherein a:b:C is (4.391~0.7318):1:1.
4. high refractive index acrylate copolymer (I) according to claim 1, which is characterized in that the high refractive index acrylic acid
The refractive index of ester copolymer (I) is not less than 1.5.
5. a kind of preparation method of high refractive index acrylate copolymer, which is characterized in that including following two step：The first step will
The mixed liquor of the acrylate monomer (II) of hydroxyl, initiator and polymerization inhibitor is added drop-wise to biphenylmethanol acrylate BPMA solution
In, reaction temperature and time are controlled, polymerization obtains intermediary copolymer (IV)；Second step is by (methyl) isocyanates acrylic acid second
It is to polymerize in (IV) intermediary copolymer that ester (III) is added drop-wise to structural formula with catalyst mixed liquid, controls reaction temperature and time,
Final polymerization obtains the copolymer (I) of required structure.
6. the preparation method of high refractive index acrylate copolymer according to claim 4, it is characterised in that including：First
The mixed liquor of the acrylate monomer (II) of hydroxyl, initiator and polymerization inhibitor is added drop-wise to biphenylmethanol acrylate solution by step
In, time for adding is 30min~40min, and range of reaction temperature is 100~120 DEG C, and the reaction time is 6~8h；Second step will
(methyl) isocyanates ethyl acrylate is added drop-wise to catalyst mixed liquid in intermediary copolymer (IV), and time for adding is
30min~40min, ranging from 80~90 DEG C of polymeric reaction temperature, reaction time are 4~6h.
7. the preparation method of high refractive index acrylate copolymer according to claim 4, which is characterized in that initiation used
The quality of agent be the gross mass of the acrylate monomer (II) of biphenylmethanol acrylate BPMA and hydroxyl (0.5~
5.0) %；The catalyst quality is the acrylate monomer (II) and (methyl) of biphenylmethanol acrylate BPMA, hydroxyl
(1.0~5.0) ‰ of the gross mass of isocyanates ethyl acrylate (III).
8. the preparation method of high refractive index acrylate copolymer according to claim 4, which is characterized in that the initiation
The quality of agent is the 1.0% of the gross mass of the acrylate monomer (II) of biphenylmethanol acrylate BPMA and hydroxyl；Second
Step used catalyst quality is biphenylmethanol acrylate (BPMA), the acrylate monomer (II) of hydroxyl and (methyl) isocyanide
The 2.5 ‰ of the gross mass of acid esters ethyl acrylate (III).
9. the preparation method of high refractive index acrylate copolymer according to claim 4, which is characterized in that the initiation
Agent is peroxide, preferably benzoyl peroxide BPO.
10. the preparation method of high refractive index acrylate copolymer according to claim 4, which is characterized in that described to urge
Agent is organotin or organo-bismuth class, preferably lauric acid bismuth.
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| 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 |
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| 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 |
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| CN108484821B (en) | 2020-12-08 |
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