CN114605639B - Cyclothio compound composition and optical material thereof - Google Patents
Cyclothio compound composition and optical material thereof Download PDFInfo
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- CN114605639B CN114605639B CN202210228281.0A CN202210228281A CN114605639B CN 114605639 B CN114605639 B CN 114605639B CN 202210228281 A CN202210228281 A CN 202210228281A CN 114605639 B CN114605639 B CN 114605639B
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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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/30—Low-molecular-weight compounds
- C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
- C08G18/3855—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur
- C08G18/3876—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing mercapto groups
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/16—Catalysts
- C08G18/22—Catalysts containing metal compounds
- C08G18/24—Catalysts containing metal compounds of tin
- C08G18/244—Catalysts containing metal compounds of tin tin salts of carboxylic acids
- C08G18/246—Catalysts containing metal compounds of tin tin salts of carboxylic acids containing also tin-carbon bonds
-
- 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
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
-
- 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
- C08G75/00—Macromolecular compounds obtained by reactions forming a linkage containing sulfur with or without nitrogen, oxygen, or carbon in the main chain of the macromolecule
- C08G75/02—Polythioethers
- C08G75/06—Polythioethers from cyclic thioethers
- C08G75/08—Polythioethers from cyclic thioethers from thiiranes
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B1/00—Optical elements characterised by the material of which they are made; Optical coatings for optical elements
- G02B1/04—Optical elements characterised by the material of which they are made; Optical coatings for optical elements made of organic materials, e.g. plastics
- G02B1/041—Lenses
-
- G—PHYSICS
- G02—OPTICS
- G02C—SPECTACLES; SUNGLASSES OR GOGGLES INSOFAR AS THEY HAVE THE SAME FEATURES AS SPECTACLES; CONTACT LENSES
- G02C7/00—Optical parts
- G02C7/02—Lenses; Lens systems ; Methods of designing lenses
- G02C7/022—Ophthalmic lenses having special refractive features achieved by special materials or material structures
Abstract
The present invention relates to an episulfide compound and an optical materialThe material, in particular to an episulfide compound composition and an optical material thereof. The episulfide compound composition comprises a compound (a), a compound (b) and a compound (c),
Description
Technical Field
The invention relates to an episulfide compound and an optical material, in particular to an episulfide compound composition and an optical material thereof.
Background
In recent years, with the development of optical resin technology, the improvement of refractive index of an optical resin lens has been a target for future lens pursuits. The sulfur-containing compound, especially the polycyclic sulfur compound, which can be used as the raw material for preparing the resin lens with ultrahigh refractive index and the formulation technology thereof are developed successively.
However, the epoxy group compound contained in the episulfide compound has higher activity, the episulfide compound is extremely easy to self-polymerize in the storage process, the product is deteriorated, meanwhile, the episulfide compound is sometimes subjected to polymerization curing, and the polymerization speed is extremely high, even explosion polymerization is sometimes caused, so that the epoxy group compound has extremely high danger in the polymerization application process and can cause huge loss, and in the aspect of resin lens application, the episulfide compound is excessively high in polymerization, the diopter of the lens is extremely high, and the reject ratio of the resin lens is increased. Second, the content of allyl group compounds in the episulfide compound affects the polymerization rate and seriously affects the heat resistance of the polymer.
Although many patents have been reported to improve the storage stability and polymerization rate, such as patent CN107250124B and japanese patent laid-open No. 2005-272418, which mention the addition of an epoxy compound having a halogen group to improve the stability, the resulting cured optical material may suffer from cloudiness, poor transmittance of the optical material, and affect the quality of the optical material.
Disclosure of Invention
Aiming at the problems in the prior art, the invention provides an episulfide compound composition and an optical material thereof, wherein the episulfide compound composition can improve the storage stability of episulfide compounds and control the polymerization rate and the heat resistance of the optical material in the preparation process of the optical material. The composition is very suitable for optical materials such as lenses, prisms, optical fibers, filters and the like, and is particularly suitable for compositions for optical materials of lenses.
The episulfide compound composition provided by the invention comprises: compound (a), compound (b), compound (c), the structural formula of which is as follows:
wherein x represents an integer of 1 to 2.
The mass ratio of the compound (b) to the compound (a) in the episulfide compound composition is 0.01-0.15:1, preferably 0.03-0.08:1; the mass ratio of the compound (c) to the compound (a) is 0.01 to 0.20:1, preferably 0.03 to 0.15:1.
There is further provided an optical material composition comprising, from the above-mentioned episulfide compound composition: isocyanate, polythiol, catalyst and the above-mentioned episulfide compound composition provided by the invention.
The optical material composition comprises the following components in parts by weight: 55-90 parts of an episulfide compound composition; 1-20 parts of isocyanate; 1-20 parts of polythiol; the catalyst is 0.01-5 parts.
Preferably, the episulfide compound composition is 80 to 90 parts; 3-10 parts of isocyanate; 3-10 parts of polythiol; the catalyst is 0.01-1 part.
In the optical material composition, the polythiol may be a conventional technique, and may be selected from one or more of the following, among others: methyl dithiol, 1, 2-ethanedithiol, 1-propanedithiol, 1, 2-propanedithiol, 1, 3-propanedithiol, 2' -thiobis (ethanethiol), 1, 6-dimercaptohexane, 2, 3-bis (2-mercaptoethylthio) -3-propyl-1-thiol, pentaerythritol tetrakis (3-mercaptopropionate), 4-mercaptomethyl-1, 8-dimercapto-3, 6-dithiooctane, 2-bis (mercaptomethyl) -1, 3-propyldithiol, bis (2-mercaptoethyl) sulfide, tetrakis (mercaptomethyl) methane, 2- (2-mercaptoethylthio) propyl-1, 3-dithiol, 2- (2, 3-bis (2-mercaptoethylthio) propylthio) ethanethiol, bis (2, 3-dimercaptopropanol) sulfide, bis (2, 3-dimercaptopropanol) and 1, 2-bis (2-mercaptoethylthio) -3-mercaptopropane; more preferably bis (2-mercaptoethyl) sulfide.
In the optical material composition, the isocyanate may be a conventional technology, preferably one or more selected from norbornane diisocyanate, 4-dicyclohexylmethane diisocyanate, isophorone diisocyanate and hexamethylene diisocyanate, more preferably isophorone diisocyanate.
In the optical material composition, the catalyst may be one of conventional techniques, preferably imidazoles, phosphines, and the like.
The beneficial effects of the invention are as follows:
firstly, in the episulfide compound composition provided by the invention, the components of the compound (a), the compound (b) and the compound (c) simultaneously contain a certain amount of epoxy groups and allyl groups, so that the storage stability of the episulfide compound is improved, the polymerization speed in the manufacturing process of an optical material can be controlled, and the heat resistance of the optical material is improved. In particular, when the compositions of the compound (a), the compound (b) and the compound (c) are within the ratio range defined in the present application, the storage stability of the episulfide compound can be more excellent, and the control of the polymerization rate in the production process of the optical material and the improvement of the heat resistance of the optical material can be more effective.
Detailed Description
The above-described aspects of the present invention will be described in further detail by way of the following embodiments, but it should not be construed that the scope of the above-described subject matter of the present invention is limited to the following examples. All techniques realized based on the above description of the present invention are within the scope of the present invention, and the following examples are accomplished by conventional techniques unless otherwise specified.
The methods for evaluating the stability of the episulfide compound, the polymerization rate for producing an optical material, and the heat resistance of the optical material in examples and comparative examples were as follows:
1. stability evaluation
Storage evaluation conditions: the mixture was left to stand for 30 days at room temperature of 25℃with a humidity of 30%. Stability evaluation method: analysis was performed by a gas chromatograph, and the change in the content of the episulfide compound (a) was followed, and the content was reduced (0, 3% ], the content was preferably reduced (3%, 8% ], the content was good, and the content was reduced (8%, 100% ], the content was poor.
2. Evaluation of polymerization Rate
The polymerization rate was evaluated based on the cumulative time taken for the prepolymer to completely lose fluidity during one cure.
3. Evaluation of Heat resistance
The optical material was prepared to a thickness of 3mm, placed in a test crucible, heated at a rate of 10 ℃/min, and evaluated by determining the glass transition temperature (Tg) of the optical material according to the obtained test curve using a detection instrument of the METTLER-DSC3 type.
In the following examples and comparative examples, when x=1 in the structural formulae of the above-mentioned compound (a), compound (b) and compound (c), they are referred to as compound (a), respectively 1 ) Compound (b) 1 ) Compound (c) 1 ) The method comprises the steps of carrying out a first treatment on the surface of the When x=2, they are respectively referred to as compounds (a) 2 ) Compound (b) 2 ) Compound (c) 2 )。
Example 1
A bis (beta-cyclopropyl) sulfide composition comprising a compound (a) 1 ) Compound (b) 1 ) Compound (c) 1 ) Wherein compound (b) 1 ) With compound (a) 1 ) The mass ratio of (c) was 0.01:1, compound (c) 1 ) With compound (a) 1 ) The mass ratio of (2) is 0.01:1.
The optical material is prepared by adopting the above-mentioned episulfide compound composition, wherein, after 87 parts by mass of the bis (beta-episulfide propyl) sulfide composition, 7 parts by mass of the bis (2-mercaptoethyl) sulfide, 5 parts by mass of isophorone diisocyanate and 0.07 part by mass of the catalyst tetrabutylphosphonium bromide are fully and uniformly mixed. Then vacuum degassing is carried out, the mixture is poured into a mould, the temperature is raised by a primary curing program, the temperature is kept for 2 hours at 20 ℃ to 55 ℃, the temperature is kept for 12 hours at 55 ℃ to 80 ℃, the temperature is kept for 3 hours at 80 ℃ for 2 hours, and the temperature is kept for 80 ℃ to 60 ℃ for 1 hour; the secondary curing was carried out at 100 ℃.
Examples 2 to 10
An episulfide compound composition comprising a compound (a) 1 ) Compound (b) 1 ) Compound (c) 1 ) Compound (b) 1 ) With compound (a) 1 ) Mass ratio of (c) and compound (c) 1 ) With compound (a) 1 ) The mass ratio of (2) was used in the ratio shown in Table 1, and the method for producing the optical material was exactly the same as in example 1.
Example 11
A bis (beta-cyclopropyl) disulfide composition comprises a compound (a) 2 ) Compound (b) 2 ) Compound (c) 2 ) Compound (b) 2 ) With compound (a) 2 ) The mass ratio of (2) is 0.05:1, compound (c) 2 ) With compound (a) 2 ) The mass ratio of (2) is 0.05:1.
The optical material is prepared by adopting the above-mentioned episulfide compound composition, wherein, after 87 parts by mass of the bis (beta-episulfide propyl) disulfide composition, 7 parts by mass of the bis (2-mercaptoethyl) sulfide, 5 parts by mass of isophorone diisocyanate and 0.07 part by mass of the catalyst tetrabutylphosphonium bromide are fully and uniformly mixed. Then vacuum degassing and pouring into a mould, and carrying out primary curing, temperature programming and heat preservation for 2 hours at 20 ℃,20-55 ℃,12 hours, 55-80 ℃,3 hours, heat preservation for 2 hours at 80 ℃,80-60 ℃ and 1 hour; the secondary curing was carried out at 100 ℃.
Example 12
An episulfide compound composition comprising a compound (a 2 ) Compound (b) 2 ) Compound (c) 2 ) Wherein compound (b) 2 ) With compound (a) 2 ) Mass ratio of (c) and compound (c) 2 ) With compound (a) 2 ) The mass ratio of (2) was used in the ratio shown in Table 1, and the method for producing the optical material was exactly the same as in example 11.
Comparative example 1
Bis (beta-cyclopropyl) sulfide composition comprising compound (a) 1 ) Compound (c) 1 ) Wherein compound (c) 1 ) With compound (a) 1 ) The mass ratio of (2) is 0.10:1.
the optical material is prepared by adopting the above-mentioned episulfide compound composition, wherein, after 87 parts by mass of the bis (beta-episulfide propyl) sulfide composition, 7 parts by mass of the bis (2-mercaptoethyl) sulfide, 5 parts by mass of isophorone diisocyanate and 0.07 part by mass of the catalyst tetrabutylphosphonium bromide are fully and uniformly mixed. Then vacuum degassing and pouring into a mould, and carrying out primary curing, temperature programming and heat preservation for 2 hours at 20 ℃,20-55 ℃,12 hours, 55-80 ℃,3 hours, heat preservation for 2 hours at 80 ℃,80-60 ℃ and 1 hour; the secondary curing was carried out at 100 ℃.
Comparative examples 2 to 3
In the episulfide Compound composition, compound (b) 1 ) With compound (a) 1 ) Mass ratio of (c) and compound (c) 1 ) With compound (a) 1 ) The mass ratio of (2) was used in the ratio shown in Table 1, and the method for producing the optical material was exactly the same as that of comparative example 1.
Table 1 evaluation results
The data in Table 1 further demonstrates that the thiol compound composition of the present application has more excellent stability than the prior art, can control the polymerization rate better, and improves the heat resistance of the optical material.
The previous description of the disclosed embodiments is provided to enable any person skilled in the art to make or use the present invention. Various modifications to these embodiments will be readily apparent to those skilled in the art, and the generic principles defined herein may be applied to other embodiments without departing from the spirit or scope of the invention. Thus, the present invention is not intended to be limited to the embodiments shown herein but is to be accorded the widest scope consistent with the principles and novel features disclosed herein.
Claims (9)
1. An episulfide compound composition, characterized by comprising: compound (a), compound (b), compound (c), each having the following structural formula:
wherein x represents an integer of 1 to 2;
in the episulfide compound composition, the mass ratio of the compound (b) to the compound (a) is 0.01-0.15:1; the mass ratio of the compound (c) to the compound (a) is 0.01-0.20:1.
2. The episulfide compound composition according to claim 1, characterized in that the mass ratio of the compound (b) to the compound (a) is 0.03-0.08:1.
3. The episulfide compound composition according to claim 1, characterized in that the mass ratio of the compound (c) to the compound (a) is 0.03-0.15:1.
4. An optical material composition, characterized in that it comprises: an isocyanate, a polythiol, a catalyst, and the episulfide compound composition according to claim 1.
5. The optical material composition according to claim 4, wherein, in parts by weight: 55-90 parts of an episulfide compound composition; 1-20 parts of isocyanate; 1-20 parts of polythiol; the catalyst is 0.01-5 parts.
6. The optical material composition according to claim 4 or 5, wherein the episulfide compound composition is 80 to 90 parts by weight; 3-10 parts of isocyanate; 3-10 parts of polythiol; the catalyst is 0.01-1 part.
7. The optical material composition of claim 4, wherein the polythiol is selected from one or more of the following: methyl dithiol, 1, 2-ethanedithiol, 1-propanedithiol, 1, 2-propanedithiol, 1, 3-propanedithiol, 2' -thiobis (ethanethiol), 1, 6-dimercaptohexane, 2, 3-bis (2-mercaptoethylthio) -3-propyl-1-thiol, pentaerythritol tetrakis (3-mercaptopropionate), 4-mercaptomethyl-1, 8-dimercapto-3, 6-dithiooctane, 2-bis (mercaptomethyl) -1, 3-propyldithiol, bis (2-mercaptoethyl) sulfide, tetrakis (mercaptomethyl) methane, 2- (2-mercaptoethylthio) propyl-1, 3-dithiol, 2- (2, 3-bis (2-mercaptoethylthio) propylthio) ethane thiol, bis (2, 3-dimercaptopropanol) sulfide, bis (2, 3-dimercaptopropanol) and 1, 2-bis (2-mercaptoethylthio) -3-mercaptopropane.
8. The optical material composition according to claim 4, wherein the isocyanate is one or more selected from the group consisting of norbornane diisocyanate, 4' -dicyclohexylmethane diisocyanate, isophorone diisocyanate, and hexamethylene diisocyanate.
9. The optical material composition according to claim 4, wherein the catalyst is one selected from imidazoles and phosphines.
Priority Applications (3)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CN202210228281.0A CN114605639B (en) | 2022-03-08 | 2022-03-08 | Cyclothio compound composition and optical material thereof |
| KR1020220122768A KR20230132346A (en) | 2022-03-08 | 2022-09-27 | Episulfide Compound Composition and Optical Material Thereof |
| JP2022157201A JP7460311B2 (en) | 2022-03-08 | 2022-09-30 | Episulfide compound composition and optical material |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| CN202210228281.0A CN114605639B (en) | 2022-03-08 | 2022-03-08 | Cyclothio compound composition and optical material thereof |
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| Publication Number | Publication Date |
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| CN114605639A CN114605639A (en) | 2022-06-10 |
| CN114605639B true CN114605639B (en) | 2023-06-02 |
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| JP (1) | JP7460311B2 (en) |
| KR (1) | KR20230132346A (en) |
| CN (1) | CN114605639B (en) |
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| WO2024024918A1 (en) * | 2022-07-29 | 2024-02-01 | 三井化学株式会社 | Polymerizable composition, resin, molded article, optical material, and lens |
| CN116143767B (en) * | 2022-12-13 | 2024-02-23 | 益丰新材料股份有限公司 | Episulfide compound, composition for optical material, optical material and application |
| CN116425660A (en) * | 2023-03-31 | 2023-07-14 | 益丰新材料股份有限公司 | Composition for optical material and method for producing optical material |
| CN116478108B (en) * | 2023-03-31 | 2023-10-13 | 益丰新材料股份有限公司 | Sulfur-containing heterocyclic compound, optical material composition and application thereof |
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| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JP3563006B2 (en) * | 1999-12-10 | 2004-09-08 | 三井化学株式会社 | (Thio) epoxy polymerizable composition |
| KR100868131B1 (en) * | 2001-04-06 | 2008-11-10 | 미츠비시 가스 가가쿠 가부시키가이샤 | Polymerization regulator and composition for resin |
| AU2003221343A1 (en) * | 2002-03-12 | 2003-09-22 | Mitsui Chemicals, Inc. | Thioepoxy based polymerizable composition and method for production thereof |
| JP3973617B2 (en) * | 2003-11-04 | 2007-09-12 | 三井化学株式会社 | (Thio) epoxy polymerizable composition |
| US20100298519A1 (en) * | 2006-03-31 | 2010-11-25 | Mitsui Chemicals, Inc. | Polymerizable composition, and resin and optical part using the same |
| EP2805949B1 (en) * | 2012-01-20 | 2016-08-17 | KOC Solution Co. Ltd. | Method for preparing thioepoxy-based optical material and polymerizable composition thereof |
| US9518153B2 (en) * | 2012-03-01 | 2016-12-13 | Mitsubishi Gas Chemical Company, Inc. | Polymerizable composition for optical materials |
| CN103703044B (en) * | 2012-09-10 | 2015-03-18 | 三菱瓦斯化学株式会社 | Composition for optical material, and method for producing same |
| CN107250125B (en) * | 2015-03-31 | 2018-07-13 | 三菱瓦斯化学株式会社 | Novel episulfide compounds and the composition for optical material comprising it |
| US10132961B2 (en) * | 2015-03-31 | 2018-11-20 | Mitsubishi Gas Chemical Company, Inc. | Episulfide compound and optical material composition including same |
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2022
- 2022-03-08 CN CN202210228281.0A patent/CN114605639B/en active Active
- 2022-09-27 KR KR1020220122768A patent/KR20230132346A/en unknown
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| JP2023131089A (en) | 2023-09-21 |
| JP7460311B2 (en) | 2024-04-02 |
| KR20230132346A (en) | 2023-09-15 |
| CN114605639A (en) | 2022-06-10 |
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