CN103172826B - High-scratch-resistance optical resin monomer and preparation method thereof - Google Patents
High-scratch-resistance optical resin monomer and preparation method thereof Download PDFInfo
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- CN103172826B CN103172826B CN201310068688.2A CN201310068688A CN103172826B CN 103172826 B CN103172826 B CN 103172826B CN 201310068688 A CN201310068688 A CN 201310068688A CN 103172826 B CN103172826 B CN 103172826B
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Abstract
The invention relates to a preparation method of a resin monomer, and relates to a high-scratch-resistance optical resin monomer and a preparation method thereof. The optical resin monomer comprises the components of, by weight, 21-23 parts of dimethyl terephthalate, 3-5 parts of propylene glycol, 2-4 parts of propylene alcohol, 37-39 parts of oligomer, 16-19 parts of CR-39, 7-9 parts of dibutyl maleate, 2-4 parts of pentaerythritol tetramercapto acetate, 3-5 parts of a bismaleimide body, and 3-5 parts of diphenylmethane diisocyanate, wherein a total weight of the components is 100%. When the optical resin monomer provided by the invention is used for producing resin lens, the refractive index of the resin lens can be 1.56 and higher. Therefore, high refractive index is ensured, and relatively high scratch resistance can be obtained.
Description
Technical field
The present invention relates to a kind of preparation method of resin monomer, specifically a kind of high adhesion strength optical resin monomer and preparation method thereof.
Background technology
In recent years, optical resin lens at home and abroad on glasses market demand increasing, resin lens is compared with glass mirror, has that quality is light, shock-resistant, dyeing behavior, is easy to the advantages such as processing.Middle high refractive index optical resin lens more obtains user's favor with high transmission rate, anti-ultraviolet, the distinctive advantage such as ultra-thin.Conventionally, it is high refractive index that the specific refractory power of take in eyeglass industry reaches more than 1.60, and specific refractory power reaches 1.56 for middle specific refractory power, and specific refractory power is being low-refraction below 1.56.At present, very common for the production of the preparation of the optical resin monomer of low-refraction eyeglass, but be not still very ripe for the production of the technology of preparing of the optical resin monomer of middle high refractive index eyeglass, domestic Duo eyeglass manufacturer all needs dependence on import; Although still have at present the preparation technology of high refractive index lens optical resin monomer in some, resin monomer adds the eyeglass aberration after pigment moulding larger, and qualification rate is not high, and colour of lens stability is bad, and qualification rate is low.As everyone knows, resin lens shortcoming has: surface abrasion resistance power, and anti-chemical capacity is poorer than glass, and surface is cut easily, often needs to improve by film coating method, has increased use cost.
Summary of the invention
Technical problem to be solved by this invention is, the shortcoming existing for above prior art, a kind of high adhesion strength optical resin monomer and preparation method thereof is proposed, in can guaranteeing, can obtain higher adhesion strength when high refractive index, and add the eyeglass aberration after pigment moulding very little, qualification rate is high.
The technical scheme that the present invention solves above technical problem is:
A high adhesion strength optical resin monomer, the weight part of its each component is:
Dimethyl terephthalate (DMT) 21-23
Propylene glycol 3-5
Vinylcarbinol 2-4
Oligopolymer 37-39
CR-39 16-19
Dibutyl maleate 7-9
Tetramethylolmethane four mercaptoacetate 2-4
Bismaleimides body 3-5
Diphenylmethanediisocyanate 3-5,
The weight part sum of each component is 100% above;
Described oligopolymer carries out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 65-69%
Vinyl carbinol 29-33%
Calcium hydroxide 0.6-0.9%
Salt of wormwood 0.6-0.9%
Each component sum is 100% later,
Drop in reactor, heat to 120-135 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, reaction times 15-17 hour;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 160-180 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 80-83% after (ii) step distills
Propylene glycol 17-22%
Dibutyltin oxide 0.09-0.12%
Thermo-stabilizer 0.06-0.09%
Each component sum is 100% later,
Reactor is heated to 180-195 ℃, and intensification limit, limit is stirred and made each raw material reaction, and reaction 3-5 hour, is then cooled to room temperature;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 85-90% (iii)
Poly-propylene carbonate base glycol ether ester 5-7%
Toxilic acid dibutylester 5-10%
Stablizer 0.07-0.09%
Each component sum is 100% later,
Mix and blend 3-5 hour, filters and makes oligopolymer.
The preparation method of aforesaid high adhesion strength optical resin monomer, after oligopolymer prepares by above step, by proportioning, oligopolymer, dimethyl terephthalate (DMT), propylene glycol, vinylcarbinol, CR-39, dibutyl maleate, tetramethylolmethane four mercaptoacetates, bismaleimides body and diphenylmethanediisocyanate are added to mixing kettle, react 5-7 hour, after adjustment refractive index, obtain the high adhesion strength optical resin monomer of thick liquid nano.
In order to guarantee that resin monomer can obtain higher adhesion strength when having middle high refractive index, the inventor conducts in-depth research, after adding tetramethylolmethane four mercaptoacetates, bismaleimides body and mixtures of diisocyanates and diphenylmethane, the adhesion strength of the eyeglass that this alicyclic monomer is made is significantly improved, by detecting its specific refractory power, discovery is along with adding the difference of tetramethylolmethane four mercaptoacetates, bismaleimides body and each content of diphenylmethanediisocyanate, and specific refractory power can have different impacts; The inventor finds through research, and tetramethylolmethane four mercaptoacetates, bismaleimides body and mixtures of diisocyanates and diphenylmethane add when more, and adhesion strength increases, non-friable, but specific refractory power can decline; Tetramethylolmethane four mercaptoacetates, bismaleimides body and mixtures of diisocyanates and diphenylmethane add when less, and monomer viscosity is high, and eyeglass difficulty is done, and adhesion strength cannot improve; In addition, when oligopolymer is more, eyeglass solidifies difficult, and eyeglass is very crisp; By deep test, the inventor has finally determined above each component concentration, can obtain higher adhesion strength when high refractive index, and add the eyeglass aberration after pigment moulding very little in can guaranteeing, qualification rate is high, thereby has completed the present invention.
The technical scheme that the present invention further limits is:
Aforesaid high adhesion strength optical resin monomer, step (iii) in, the thermo-stabilizer adding is CAS 3287-06-7, CAS 522-21-1, CAS 12141-20-7, CAS 16038-76-9 or CAS 26544-22-9.
Aforesaid high adhesion strength optical resin monomer, step (iv) in, the stablizer adding is CAS 100-51-6 or CAS 75-08-1.
The invention has the beneficial effects as follows: product of the present invention is during for the production of resin lens, the refractive index that makes to guarantee resin lens reach 1.56 and more than, when guaranteeing high index, can also obtain higher adhesion strength, after testing, most of resin lens adhesion strength friction haze value (Hs) of making is 0.2-0.25, have even lower than 0.2, adhesion strength is good; In addition, product of the present invention is more stable compared with like product character, adds the eyeglass aberration after pigment moulding very little, and qualification rate is high, and colour of lens stability is better, and test does not change the high 5-10% of the more domestic like product of qualification rate after adjusting substantially.
Embodiment
embodiment 1
A high adhesion strength optical resin monomer, the weight part of its each component is:
Dimethyl terephthalate (DMT) 21
Propylene glycol 3
Vinylcarbinol 4
Oligopolymer 37
CR-39 16
Dibutyl maleate 7
Tetramethylolmethane four mercaptoacetates 4
Bismaleimides body 3
Diphenylmethanediisocyanate 5.
The preparation method of the high adhesion strength optical resin monomer of the present embodiment, carries out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 66%
Vinyl carbinol 32.5%
Calcium hydroxide 0.9%
Salt of wormwood 0.6%
Drop in reactor, heat to 120 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, 15 hours reaction times;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 160 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 80% after (ii) step distills
Propylene glycol 19.8%
Dibutyltin oxide 0.12%
Thermo-stabilizer 0.08%
Reactor is heated to 180 ℃, and intensification limit, limit is stirred and made each raw material reaction, reacts 3 hours, is then cooled to room temperature, and thermo-stabilizer is CAS 3287-06-7, CAS 522-21-1, CAS 12141-20-7, CAS 16038-76-9 or CAS 26544-22-9;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 85% (iii)
Poly-propylene carbonate base glycol ether ester 5%
Toxilic acid dibutylester 9.93%
Stablizer 0.07%
Mix and blend 3 hours, filters and makes described oligopolymer, and the stablizer adding is CAS 100-51-6 or CAS 75-08-1;
(v) by proportioning, oligopolymer, dimethyl terephthalate (DMT), propylene glycol, vinylcarbinol, CR-39, dibutyl maleate, tetramethylolmethane four mercaptoacetates, bismaleimides body and diphenylmethanediisocyanate are added to mixing kettle, react 5 hours, after adjustment refractive index, obtain the high adhesion strength optical resin monomer of thick liquid nano.
The present embodiment is during for the production of resin lens, the refractive index that makes to guarantee resin lens reach 1.56 and more than, when guaranteeing high index, can also obtain higher adhesion strength, resin lens adhesion strength friction haze value (Hs) is 0.25.
embodiment 2
A high adhesion strength optical resin monomer, the weight part of its each component is:
Dimethyl terephthalate (DMT) 21
Propylene glycol 5
Vinylcarbinol 2
Oligopolymer 37
CR-39 16
Dibutyl maleate 9
Tetramethylolmethane four mercaptoacetates 2
Bismaleimides body 5
Diphenylmethanediisocyanate 3.
The preparation method of the high adhesion strength optical resin monomer of the present embodiment, carries out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 66%
Vinyl carbinol 32.5%
Calcium hydroxide 0.6%
Salt of wormwood 0.9%
Drop in reactor, heat to 130 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, 16 hours reaction times;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 170 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 81% after (ii) step distills
Propylene glycol 17.85%
Dibutyltin oxide 0.09%
Thermo-stabilizer 0.06%
Reactor is heated to 190 ℃, and intensification limit, limit is stirred and made each raw material reaction, reacts 4 hours, is then cooled to room temperature, and thermo-stabilizer is CAS 3287-06-7, CAS 522-21-1, CAS 12141-20-7, CAS 16038-76-9 or CAS 26544-22-9;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 86% (iii)
Poly-propylene carbonate base glycol ether ester 5.91%
Toxilic acid dibutylester 8%
Stablizer 0.09%
Mix and blend 4 hours, filters and makes described oligopolymer, and the stablizer adding is CAS 100-51-6 or CAS 75-08-1;
(v) by proportioning, oligopolymer, dimethyl terephthalate (DMT), propylene glycol, vinylcarbinol, CR-39, dibutyl maleate, tetramethylolmethane four mercaptoacetates, bismaleimides body and diphenylmethanediisocyanate are added to mixing kettle, react 6 hours, after adjustment refractive index, obtain the high adhesion strength optical resin monomer of thick liquid nano.
The present embodiment is during for the production of resin lens, the refractive index that makes to guarantee resin lens reach 1.56 and more than, when guaranteeing high index, can also obtain higher adhesion strength, resin lens adhesion strength friction haze value (Hs) is 0.2.
embodiment 3
A high adhesion strength optical resin monomer, the weight part of its each component is:
Dimethyl terephthalate (DMT) 22
Propylene glycol 4
Vinylcarbinol 3
Oligopolymer 39
CR-39 17
Dibutyl maleate 7
Tetramethylolmethane four mercaptoacetates 2
Bismaleimides body 3
Diphenylmethanediisocyanate 3.
The preparation method of the high adhesion strength optical resin monomer of the present embodiment, carries out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 69%
Vinyl carbinol 29.5%
Calcium hydroxide 0.9%
Salt of wormwood 0.6%
Drop in reactor, heat to 135 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, 17 hours reaction times;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 180 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 82% after (ii) step distills
Propylene glycol 17.82%
Dibutyltin oxide 0.1%
Thermo-stabilizer 0.08%
Reactor is heated to 195 ℃, and intensification limit, limit is stirred and made each raw material reaction, reacts 5 hours, is then cooled to room temperature, and thermo-stabilizer is CAS 3287-06-7, CAS 522-21-1, CAS 12141-20-7, CAS 16038-76-9 or CAS 26544-22-9;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 87% (iii)
Poly-propylene carbonate base glycol ether ester 7%
Toxilic acid dibutylester 5.92%
Stablizer 0.08%
Mix and blend 5 hours, filters and makes described oligopolymer, and the stablizer adding is CAS 100-51-6 or CAS 75-08-1;
(v) by proportioning, oligopolymer, dimethyl terephthalate (DMT), propylene glycol, vinylcarbinol, CR-39, dibutyl maleate, tetramethylolmethane four mercaptoacetates, bismaleimides body and diphenylmethanediisocyanate are added to mixing kettle, react 7 hours, after adjustment refractive index, obtain the high adhesion strength optical resin monomer of thick liquid nano.
The present embodiment is during for the production of resin lens, the refractive index that makes to guarantee resin lens reach 1.56 and more than, when guaranteeing high index, can also obtain higher adhesion strength, resin lens adhesion strength friction haze value (Hs) is 0.21.
In addition to the implementation, the present invention can also have other embodiments.All employings are equal to the technical scheme of replacement or equivalent transformation formation, all drop on the protection domain of requirement of the present invention.
Claims (4)
1. a high adhesion strength optical resin monomer, is characterized in that: the weight part of its each component is:
Dimethyl terephthalate (DMT) 21-23
Propylene glycol 3-5
Vinylcarbinol 2-4
Oligopolymer 37-39
CR-39 16-19
Dibutyl maleate 7-9
Tetramethylolmethane four mercaptoacetate 2-4
Bismaleimides 3-5
Diphenylmethanediisocyanate 3-5,
The weight part sum of each component is 100 parts above;
Described oligopolymer carries out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 65-69%
Vinyl carbinol 29-33%
Calcium hydroxide 0.6-0.9%
Salt of wormwood 0.6-0.9%
Each component sum is 100% above,
Drop in reactor, heat to 120-135 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, reaction times 15-17 hour;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 160-180 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 80-83% after (ii) step distills
Propylene glycol 17-22%
Dibutyltin oxide 0.09-0.12%
Thermo-stabilizer 0.06-0.09%
Each component sum is 100% above,
Reactor is heated to 180-195 ℃, and intensification limit, limit is stirred and made each raw material reaction, and reaction 3-5 hour, is then cooled to room temperature;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 85-90% (iii)
Poly-propylene carbonate base glycol ether ester 5-7%
Toxilic acid dibutylester 5-10%
Stablizer 0.07-0.09%
Each component sum is 100% above,
Mix and blend 3-5 hour, filters and makes oligopolymer.
2. high adhesion strength optical resin monomer as claimed in claim 1, is characterized in that: step (iii) in, the thermo-stabilizer adding is CAS 3287-06-7, CAS 522-21-1, CAS 12141-20-7, CAS 16038-76-9 or CAS 26544-22-9.
3. high adhesion strength optical resin monomer as claimed in claim 1, is characterized in that: step (iv) in, the stablizer adding is CAS 100-51-6 or CAS 75-08-1.
4. the preparation method of high adhesion strength optical resin monomer as claimed in claim 1, is characterized in that: carry out according to the following steps:
(i) by dimethyl terephthalate (DMT), vinyl carbinol, calcium hydroxide and salt of wormwood, by following weight percent:
Dimethyl terephthalate (DMT) 65-69%
Vinyl carbinol 29-33%
Calcium hydroxide 0.6-0.9%
Salt of wormwood 0.6-0.9%
Each component sum is 100% above,
Drop in reactor, heat to 120-135 ℃, after material dissolution, stir and make each raw material reaction, and reclaim the methyl alcohol of vinyl carbinol and reaction generation, reaction times 15-17 hour;
(ii) by step (i) the material after reaction kettle for reaction proceed to still kettle and distill, at 160-180 ℃, distillation, steams vinyl carbinol and methyl alcohol, vinyl carbinol and methyl alcohol are collected in condensation;
(iii) the material after (ii) step being distilled proceeds to reactor, by following weight ratio, adds propylene glycol, Dibutyltin oxide and thermo-stabilizer:
Material 80-83% after (ii) step distills
Propylene glycol 17-22%
Dibutyltin oxide 0.09-0.12%
Thermo-stabilizer 0.06-0.09%
Each component sum is 100% above,
Reactor is heated to 180-195 ℃, and intensification limit, limit is stirred and made each raw material reaction, and reaction 3-5 hour, is then cooled to room temperature;
(iv) by step (iii) the material after reaction kettle for reaction proceed to mixing kettle, by following weight ratio, add poly-propylene carbonate base glycol ether ester, toxilic acid dibutylester and stablizer:
Step is reacted material 85-90% (iii)
Poly-propylene carbonate base glycol ether ester 5-7%
Toxilic acid dibutylester 5-10%
Stablizer 0.07-0.09%
Each component sum is 100% above,
Mix and blend 3-5 hour, filters and makes described oligopolymer;
(v) by proportioning, oligopolymer, dimethyl terephthalate (DMT), propylene glycol, vinylcarbinol, CR-39, dibutyl maleate, tetramethylolmethane four mercaptoacetates, bismaleimides and diphenylmethanediisocyanate are added to mixing kettle, react 5-7 hour, after adjustment refractive index, obtain the high adhesion strength optical resin monomer of thick liquid nano.
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| CN104277308A (en) * | 2014-10-30 | 2015-01-14 | 安徽电信器材贸易工业有限责任公司 | Sheath material for seafloor communication optical cable and preparation method thereof |
| CN104497547A (en) * | 2014-11-28 | 2015-04-08 | 李国金 | High-toughness and impact-resistant resin eyeglass and preparation method thereof |
| JP2018083901A (en) * | 2016-11-24 | 2018-05-31 | 昭和電工株式会社 | Curable composition and cured product thereof |
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| JPH072818B2 (en) * | 1989-04-12 | 1995-01-18 | ダイソー株式会社 | High refractive index organic glass |
| CN101319024B (en) * | 2008-07-15 | 2010-08-11 | 寿光市鲁源盐化有限公司 | Optical resin monomer material and preparation method thereof |
| CN101614831B (en) * | 2009-08-11 | 2010-10-27 | 杭州新顺化工有限公司 | High refractivity resin lens and preparation method thereof |
| CN102532825A (en) * | 2011-12-14 | 2012-07-04 | 江苏可奥熙光学材料科技有限公司 | Preparation method for high-stability resin monomer |
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