WO2021206269A1 - Procédé de production d'un composé de polythiol, composition polymérisable pour un matériau optique le comprenant, et lentille optique - Google Patents

Procédé de production d'un composé de polythiol, composition polymérisable pour un matériau optique le comprenant, et lentille optique Download PDF

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WO2021206269A1
WO2021206269A1 PCT/KR2020/019176 KR2020019176W WO2021206269A1 WO 2021206269 A1 WO2021206269 A1 WO 2021206269A1 KR 2020019176 W KR2020019176 W KR 2020019176W WO 2021206269 A1 WO2021206269 A1 WO 2021206269A1
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compound
thiol
optical material
formula
present
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PCT/KR2020/019176
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Korean (ko)
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정대근
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주식회사 대원에프엔씨
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Priority to CN202080005058.9A priority Critical patent/CN113784998A/zh
Publication of WO2021206269A1 publication Critical patent/WO2021206269A1/fr

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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
    • 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
    • C08G75/0204—Polyarylenethioethers
    • C08G75/025—Preparatory processes
    • C08G75/0272—Preparatory processes using other sulfur sources
    • 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
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C319/00—Preparation of thiols, sulfides, hydropolysulfides or polysulfides
    • C07C319/02—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols
    • C07C319/12—Preparation of thiols, sulfides, hydropolysulfides or polysulfides of thiols by reactions not involving the formation of mercapto groups
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C321/00—Thiols, sulfides, hydropolysulfides or polysulfides
    • C07C321/12—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms
    • C07C321/14—Sulfides, hydropolysulfides, or polysulfides having thio groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
    • 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
    • C08G18/3874—Low-molecular-weight compounds having heteroatoms other than oxygen having sulfur containing heterocyclic rings having at least one sulfur atom in the ring
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • 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

Definitions

  • the present invention relates to a method for producing a polythiol compound, and to a polymerization composition for an optical material using the polythiol compound.
  • a lens manufactured using the polythiol compound is clear and transparent, has a uniform color, and is a high-purity poly
  • the present invention relates to a method and a composition for an optical material capable of producing a thiol compound inexpensively and having excellent optical properties with high heat resistance and high refractive index and ultra-high refractive index.
  • Lenses using plastic optical materials are lighter than optical materials made of inorganic materials such as glass, do not break easily, and can be dyed. is being used
  • An optical lens obtained by polymerization of a thiol compound and an isocyanate compound is widely used as an optical lens material having excellent optical properties such as transparency, Abbe's number, transmittance, heat resistance, and tensile properties.
  • the heat resistance of the 1.67 refractive index lens of the plastic optical material to which the conventionally known thiol-based compound is applied is as low as 100 ° C. it is necessary.
  • thiol-based compounds having various structures are known, and related preparation methods are also known in various ways. It is known that a thiol compound having a relatively high yield (87%) can be obtained when a compound containing a double unsaturated carbon bond is synthesized using a radical reaction and prepared by thiourea reaction. However, such a radical reaction still has problems such as low purity and low yield, and yellowing of by-products generated during the reaction.
  • the plastic optical material to which the conventionally known thiol-based compound is applied has a problem with low heat resistance of 100° C. or less, so there is a limitation in applying it to a high-temperature process. development is needed.
  • Patent Document 1 Republic of Korea Patent Publication No. 10-2014-0141723
  • Patent Document 2 Republic of Korea Patent Publication No. 10-2013-0050263
  • Patent Document 3 Republic of Korea Patent Publication No. 10-0078120
  • Patent Document 4 Republic of Korea Patent Publication No. 10-2017-0008679
  • Patent Document 5 International Patent Publication WO 2013/176506 A1
  • Patent Document 6 US Patent Publication No. US005608115A
  • An object of the present invention is to provide a method for preparing a composition containing a thiol compound having remarkably excellent heat resistance when applied to an optical material.
  • Another object of the present invention is to provide a method for preparing a composition containing a thiol compound having a high Abbe number when applied to an optical material.
  • Another object of the present invention is to provide a method for preparing a composition containing a thiol compound that meets the refractive index of a standard standard when applied to an optical material.
  • Another object of the present invention is to provide a method for preparing a composition containing a thiol compound having excellent yield and purity.
  • R 1 is an unsubstituted alcohol group having 2 to 3 carbon atoms.
  • R 2 is a halogen atom
  • the polythiol compound obtained by the above production method obtains a polythiol compound in which two positional isomers are mixed.
  • the present invention relates to a method for preparing a thiol-based composition for an optical material comprising the compound of Formula 1 as a starting material as epichlorohydrin.
  • the thiol-based composition for an optical material prepared by the method for preparing a composition for an optical material according to an embodiment of the present invention may further include a compound of Formula 2 below.
  • the thiol-based composition prepared by the method for preparing a thiol-based composition for an optical material according to an embodiment of the present invention may contain 4 to 7 parts by weight of the compound of Formula 2 based on 100 parts by weight of the compound of Formula 1 above.
  • the molar ratio of the hydrogen sulfide salt to the compound prepared in the first step may be 1:1 to 1.2.
  • the present invention also provides an optical material, and the optical material according to the present invention may be prepared by the method for producing a thiol-based compound for an optical material according to an embodiment of the present invention.
  • the optical material according to an embodiment of the present invention may be characterized in that the heat resistance temperature is 100 °C or more.
  • the optical lens prepared by using the composition containing the thiol-based compound prepared according to the present invention was clear and transparent and had excellent color.
  • the composition containing the thiol-based compound prepared in the present invention has excellent polymerizability with each polyisocyanate, so it is suitable for high-refractive ultra-high refractive (1.60, 1.67) lenses. It was possible to manufacture optical lenses with high purity and excellent thermal stability.
  • the optical material obtained according to the present invention has excellent impact resistance, heat resistance, moldability, dyeability, and light transmittance, and thus can be used in various fields.
  • composition containing the thiol-based compound for optical materials according to the present invention is prepared from epichlorohydrin as a starting material, and the compound of Formula 1 is include
  • composition containing the thiol-based compound for an optical material according to the present invention is characterized in that epichlorohydrin is used as a starting material, and the compound of formula 1 is prepared through reaction with mercapto alcohol, hydrogen sulfide, etc., which will be described later. can do.
  • epichlorohydrin is used as a starting material
  • the compound of formula 1 is prepared through reaction with mercapto alcohol, hydrogen sulfide, etc., which will be described later. can do.
  • the compound of Formula 1 is prepared in this way, there is an advantage that the compound of Formula 1 can be prepared in a remarkably high yield of 90% or more. It has characteristics that indicate
  • composition containing the thiol-based compound for an optical material according to an embodiment of the present invention further includes a compound of Formula 2 below.
  • the compound of Formula 2 is produced as a by-product as a structural isomer of Formula 1 in the process of preparing the compound of Formula 1, and finally, the composition containing the thiol-based compound for an optical material is a composition containing the compound of Formula 1 and the compound of Formula 2 simultaneously.
  • the composition containing the thiol-based compound for an optical material is a composition containing the compound of Formula 1 and the compound of Formula 2 simultaneously.
  • the thiol-based compound for an optical material in the composition containing the thiol-based compound for an optical material according to an embodiment of the present invention, 4 to 7 parts by weight of the compound of Formula 2 may be included relative to 100 parts by weight of the compound of Formula 1, preferably the compound of Formula 2 5 to 6 parts by weight may be included.
  • the thiol-based compound for an optical material according to an embodiment of the present invention can exhibit high heat resistance, and also exhibit refractive indices close to 1.60 and 1.67 meeting international standards, and exhibit a high Abbe's number. There is a characteristic.
  • the method for preparing a composition containing a thiol-based compound for an optical material specifically includes a first step of reacting epichlorohydrin with mercapto alcohol;
  • the method for preparing a thiol-based compound according to the present invention uses epichlorohydrin as a starting material, and by sequentially including the first to third steps, the yield of formula 1 and chemistry 2 is greater than 90%, preferably greater than or equal to 92%.
  • epichlorohydrin as a starting material, and by sequentially including the first to third steps, the yield of formula 1 and chemistry 2 is greater than 90%, preferably greater than or equal to 92%.
  • the first step is to open the epoxy group of epichlorohydrin to form a terminal hydroxyl group.
  • the molar ratio of mercapto alcohol: epichlorohydrin may be 1:1, and by satisfying the above-mentioned range, the ratio of mercapto alcohol or epichlorohydrin that is discarded without reaction is minimized and thiol-based compound is prepared in high yield.
  • the reaction temperature may be 20 °C or less, preferably 5 to 10 °C, there is a possibility that side reactions may occur when the temperature is too high, and a problem that the reaction rate is slowed when the temperature is low may occur.
  • the method for preparing Formula 1 includes a second step of reacting the product of the first step with a hydrogen sulfide salt to replace the chlorine at the end with a hydrogen sulfide group, and reacting with epichlorohydrin.
  • the chlorine at the terminal is derived from epichlorohydrin.
  • the second step includes a step 2-1 of reacting the product of the first step with a hydrogen sulfide salt to replace the chlorine at the end with a hydrogen sulfide group, and a step 2-2 of reacting with epichlorohydrin after substitution with a hydrogen sulfide group.
  • the hydrogen sulfide salt includes a -SH group and a cation and can be used without limitation if it is a compound that is soluble in water, and the cation may be lithium, sodium, potassium, calcium or magnesium, preferably lithium, sodium or potassium. may be, but the present invention is not limited thereto.
  • the second step includes the step of slowly adding the compound prepared in the first step to a solution in which the hydrogen sulfide salt is dissolved, and the molar ratio of the hydrogen sulfide salt to the compound prepared in the first step is 1:1 to 1.2.
  • Step 2-1 may be performed at a temperature of 40 to 60 ° C. for 3 to 10 hours, and when the temperature is too high, there is a risk of side reactions, and when the temperature is too low, a problem of lengthening the reaction time may occur. .
  • step 2-2 includes adding sodium hydroxide to the product of step 2-1, and then further adding epichlorohydrin, wherein the product of step 2-1: sodium hydroxide: epichlorohydrin
  • the molar ratio of dried may be 1: 0.5: 0.5.
  • step 2-2 the temperature of step 2-2 may be carried out at 5 to 10 °C, and then the reaction may proceed while stirring at a temperature of 35 to 50 °C.
  • the third step can be used without limitation in the case of a method of substituting a -OH group with a -SH group using a commonly known thiourea, and the present invention is not limited thereto.
  • the third step includes a step of stirring the product of the second step in a container by adding hydrochloric acid and thiourea and raising the temperature.
  • the molar ratio of the product of the second step: hydrochloric acid: thiourea may be 1: 5.5: 5.5 to 1: 6: 6, and in this range, the unsubstituted hydroxyl group is prevented from remaining and the thiol-based compound is produced in a high yield.
  • the reaction may be performed by raising the temperature to 90 to 110° C. In this case, the reaction may be performed for 4 to 8 hours, but the present invention is not limited thereto.
  • the method for producing a thiol-based compound according to an embodiment of the present invention may further include a washing step of washing the product generated after the third step, wherein the washing may use an aqueous hydrochloric acid solution, brine, etc., but the present invention does not It is not limited.
  • the present invention also provides an optical material, the optical material according to the present invention is an optical material according to an embodiment of the present invention, a thiol and an isocyanate compound for an optical material prepared by the manufacturing method according to an embodiment of the present invention are polymerized it has become
  • the manufactured optical material when an optical material is manufactured using the thiol-based compound of the present invention, the manufactured optical material exhibits a high Abbe's number, can exhibit a refractive index conforming to international standards, and has high heat resistance.
  • the optical material according to an embodiment of the present invention may have a heat resistance temperature of 100 °C or more, preferably 110 °C or more, and thus, there is an advantage that can be applied to an optical material having a relatively high temperature in use.
  • the isocyanate compound may be used without limitation if it is an isocyanate compound typically used in an optical material, and the present invention is not limited thereto.
  • the isocyanate compound is isophorone diisocyanate (IPDI), dicyclohexylmethane-4-4-diisocyanate (H 12 MDI), hexamethylene diisocyanate (HDI), 1,3- Bis (methyl isocyanate) cyclohexane (H 6 XDI) and m, o, P - may include one or two or more selected from xylene diisocyanate, but the present invention is not limited thereto.
  • IPDI is isophorone diisocyanate
  • H 12 MDI dicyclohexylmethane-4-4-diisocyanate
  • HDI hexamethylene diisocyanate
  • the amount of isocyanate added is controlled through the ratio of functional groups, and the molar ratio of -SH functional group: NCO functional group included in the isocyanate compound may be 1: 1 to 2.5, preferably 1.5 to 2, and by satisfying this range, the residual after curing It minimizes unreacted monomers and has the advantage of being able to manufacture an optical material that is strong and has excellent mechanical properties.
  • the heat resistance temperature of the optical material manufactured by satisfying the above-described functional group ratio is 100 ° C. or higher, preferably 110 ° C. or higher, which can significantly broaden the application range of the plastic-based optical material.
  • the optical material according to an embodiment of the present invention may include a UV absorber, a release agent, a dye, etc. as necessary in addition to the thiol-based compound and isocyanate compound of the present invention, but the present invention is not limited thereto.
  • the ultraviolet absorber can be used without limitation if it is an ultraviolet absorber typically used in optical materials, and the present invention is not limited thereto.
  • the ultraviolet absorber may be one or two or more selected from benzophenone-based, benzotriazo-based, salicylate-based, cyanoacrylate-based and oxanilite-based, etc., but the present invention is limited thereto. it's not going to be
  • the dye can also be used without limitation if it is a dye used in a conventional plastic optical material, and the present invention is not limited thereto.
  • the dye may be one or two or more selected from perinone-based dyes, heterocyclic dyes, perylene-based dyes, heterocyclic dyes, anthraquinone-based dyes, azo-based dyes and indigoid-based dyes. , the present invention is not limited thereto.
  • the optical material according to an embodiment of the present invention may include a polymerization initiator for polymerization of the isocyanate and the compound of Formula 1 above.
  • the polymerization initiator can be used without limitation if it is a polymerization initiator for thermal polymerization of isocyanate, and the present invention is not limited thereto.
  • the polymerization initiator may be an amine-based polymerization initiator or a tin-based polymerization initiator, preferably a tin-based polymerization initiator.
  • the tin-based polymerization initiator is specifically dibutyltin laurate, dibutyltin chloride, dibutyltin acetate, stannous oxylate, dibutyltin dilaurate, tetrafluorotin, tetrachlorotin and tetrabrorotin It may be one or two or more selected from the like, but the present invention is not limited thereto.
  • Tg glass transition temperature
  • Polymerization imbalance 100 lenses are manufactured and observed with the naked eye in the arc lamp. Lenses with different refractive indices around the lenses, which have an arc image, are judged to have polymerization imbalance, and if 5 or less, 0 is displayed, If there are 5 or more polymerization imbalances, it is indicated by ⁇ .
  • Cloudiness 100 lenses are produced and visually observed with the arc lamp. Lenses with variable or central cloudiness are judged to have cloudiness. If there is more than one, it is marked with ⁇
  • isocyanate 54.77 g of isocyanate was used. Among them, 21.64 g of dicyclohexylmethane-4,4'-diisocyanate (H12MDI), 17.75 g of isophorone diisocyanate (IPDI) and 15.37 g of hexamethylene diisocyanate (HDI) were mixed, followed by vacuum defoaming at 20 ° C. Put into a mixer capable of stirring, and to this, Zelec UNTM 0.08g, HOPET 1.2g, DBTC 0.08g.
  • H12MDI dicyclohexylmethane-4,4'-diisocyanate
  • IPDI isophorone diisocyanate
  • HDI hexamethylene diisocyanate
  • Meta-xylene diisocyanate (XDI) 49.78g was placed in a mixer capable of vacuum degassing and stirring at 20°C, and here Zelec UNTM 0.08g, HOPET 1.2g, DBTC 0.08g. Put HTAQ 30PPm, and PRD20PPm, and after stirring for 30 minutes under a nitrogen stream, 50 g of the thiol-based composition (monomer) prepared in Preparation Example of the present invention was added to obtain a polymerizable composition, and then degassed under reduced pressure at 0.1 torr or less for 1 hour and 20 minutes and injected into a glass mold fixed with an adhesive tape under nitrogen pressure.
  • the glass mold injected with the polymerizable composition into a circulating oven, heated to 20-35 °C 6 hours, 35-50 °C 7 hours, 50-90 °C 7 hours, 90-130 °C 4 hours, 130 °C After holding for 2 hours and cooling at 120-80°C for 1 hour, the solid material is removed from the mold to obtain an optical lens.
  • the optical lens thus obtained is processed to have a diameter of 72 mm and then annealed at a temperature of 120 to 130° C. for 2 hours to obtain a plastic optical lens.
  • Comparative Examples 1 to 4 are 2,3-bis(2-mercaptoethylthio)-propane-1- which is a known thiol-based compound (refer to Korean Patent Publication No. 10-2017-0008679 and Korean Patent Publication No. 10-2013-0050263).
  • Thiol (GST) is a known thiol-based compound (refer to Korean Patent Publication No. 10-2017-0008679 and Korean Patent Publication No. 10-2013-0050263).
  • DMDDU 4,8-dimercaptomethyl-1.11-dimercapto-3,6,9-trithioundecane
  • 2-(2-mercaptoethylthio)-3-(3-mercapto-2- [3-mercapto-2-(2-mercaptoethylthio)-propylthio]propylthio)-propane-1-thiol (MMPT) is shown in Table 2 by comparing the results of measurement of physical properties with Table 1 with reference to .
  • DMDDU 4,8-dimercaptomethyl-1.11-dimercapto-3,6,9-trithiaundecane.
  • PETMP pentaerythritol-tetrakis (3-mercaptopropionate)
  • IPDI isophorone diisocyanate
  • HOPBT 2-(2'-hydroxyl-5'-t-octiphenyl)-2H-benzotriazole

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Physics & Mathematics (AREA)
  • General Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Abstract

L'invention concerne une composition à base de thiol pour un matériau optique, caractérisée en ce qu'elle comprend un composé de formule chimique 1 et un composé de formule chimique 2.
PCT/KR2020/019176 2020-04-09 2020-12-28 Procédé de production d'un composé de polythiol, composition polymérisable pour un matériau optique le comprenant, et lentille optique WO2021206269A1 (fr)

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CN202080005058.9A CN113784998A (zh) 2020-04-09 2020-12-28 制备多硫醇化合物的方法、使用其的用于光学材料的可聚合组合物、以及光学透镜

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KR102122703B1 (ko) * 2020-04-09 2020-06-26 주식회사 대원에프엔씨 폴리티올 화합물의 제조 방법과 이를 포함한 광학 재료용 중합성 조성물 및 광학 렌즈
KR102448166B1 (ko) * 2020-09-22 2022-09-27 에스케이씨 주식회사 폴리티올 조성물 및 이를 포함하는 광학용 중합성 조성물
KR102707088B1 (ko) * 2020-11-27 2024-09-19 에스케이피유코어 주식회사 폴리티올 조성물, 광학 조성물 및 광학 제품
EP4253443A4 (fr) * 2020-11-27 2024-10-23 Sk Pucore Co Ltd Composition de polythiol, composition optique et produit optique

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