WO2015163313A1 - 光学材料用重合性組成物、光学材料および光学材料の製造方法 - Google Patents
光学材料用重合性組成物、光学材料および光学材料の製造方法 Download PDFInfo
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- WO2015163313A1 WO2015163313A1 PCT/JP2015/062080 JP2015062080W WO2015163313A1 WO 2015163313 A1 WO2015163313 A1 WO 2015163313A1 JP 2015062080 W JP2015062080 W JP 2015062080W WO 2015163313 A1 WO2015163313 A1 WO 2015163313A1
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- ZMZDMBWJUHKJPS-UHFFFAOYSA-N hydrogen thiocyanate Natural products SC#N ZMZDMBWJUHKJPS-UHFFFAOYSA-N 0.000 description 1
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- 238000003384 imaging method Methods 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- BGXUHYCDVKDVAI-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfanyl)methane Chemical compound O=C=NCSCN=C=O BGXUHYCDVKDVAI-UHFFFAOYSA-N 0.000 description 1
- ZHWJTCDUSSCFOZ-UHFFFAOYSA-N isocyanato(isocyanatomethylsulfanylmethylsulfanyl)methane Chemical compound O=C=NCSCSCN=C=O ZHWJTCDUSSCFOZ-UHFFFAOYSA-N 0.000 description 1
- OFUBORBAMWUXTI-UHFFFAOYSA-N isocyanato-(isocyanatomethyldisulfanyl)methane Chemical compound O=C=NCSSCN=C=O OFUBORBAMWUXTI-UHFFFAOYSA-N 0.000 description 1
- NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 description 1
- CMXVCNCLYPZFPK-UHFFFAOYSA-N isothiocyanato(isothiocyanatomethylsulfanyl)methane Chemical compound S=C=NCSCN=C=S CMXVCNCLYPZFPK-UHFFFAOYSA-N 0.000 description 1
- 239000004611 light stabiliser Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 239000012046 mixed solvent Substances 0.000 description 1
- 239000006082 mold release agent Substances 0.000 description 1
- PJUIMOJAAPLTRJ-UHFFFAOYSA-N monothioglycerol Chemical compound OCC(O)CS PJUIMOJAAPLTRJ-UHFFFAOYSA-N 0.000 description 1
- 238000000465 moulding Methods 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000001451 organic peroxides Chemical class 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 230000000704 physical effect Effects 0.000 description 1
- 238000013001 point bending Methods 0.000 description 1
- 238000005498 polishing Methods 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 229920000582 polyisocyanurate Polymers 0.000 description 1
- 239000011495 polyisocyanurate Substances 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 229920005862 polyol Polymers 0.000 description 1
- 239000005077 polysulfide Substances 0.000 description 1
- 229920001021 polysulfide Polymers 0.000 description 1
- 150000008117 polysulfides Polymers 0.000 description 1
- 238000012545 processing Methods 0.000 description 1
- YPVDWEHVCUBACK-UHFFFAOYSA-N propoxycarbonyloxy propyl carbonate Chemical compound CCCOC(=O)OOC(=O)OCCC YPVDWEHVCUBACK-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- VUTVSWPVTJZPFU-UHFFFAOYSA-N propylsulfanylmethanethiol Chemical compound CCCSCS VUTVSWPVTJZPFU-UHFFFAOYSA-N 0.000 description 1
- LVTJOONKWUXEFR-FZRMHRINSA-N protoneodioscin Natural products O(C[C@@H](CC[C@]1(O)[C@H](C)[C@@H]2[C@]3(C)[C@H]([C@H]4[C@@H]([C@]5(C)C(=CC4)C[C@@H](O[C@@H]4[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@@H](O)[C@H](O[C@H]6[C@@H](O)[C@@H](O)[C@@H](O)[C@H](C)O6)[C@H](CO)O4)CC5)CC3)C[C@@H]2O1)C)[C@H]1[C@H](O)[C@H](O)[C@H](O)[C@@H](CO)O1 LVTJOONKWUXEFR-FZRMHRINSA-N 0.000 description 1
- 238000004080 punching Methods 0.000 description 1
- 230000002940 repellent Effects 0.000 description 1
- 239000005871 repellent Substances 0.000 description 1
- 239000011342 resin composition Substances 0.000 description 1
- 239000003566 sealing material Substances 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000003381 stabilizer Substances 0.000 description 1
- 150000005846 sugar alcohols Polymers 0.000 description 1
- WTSBJMAOQNCZBF-UHFFFAOYSA-N sulfanylmethylsulfanylmethanethiol Chemical compound SCSCS WTSBJMAOQNCZBF-UHFFFAOYSA-N 0.000 description 1
- QNITWMBGUWZSSI-UHFFFAOYSA-N sulfanylmethylsulfanylmethylsulfanylmethanethiol Chemical compound SCSCSCS QNITWMBGUWZSSI-UHFFFAOYSA-N 0.000 description 1
- 229910052717 sulfur Inorganic materials 0.000 description 1
- 239000011593 sulfur Substances 0.000 description 1
- NMOALOSNPWTWRH-UHFFFAOYSA-N tert-butyl 7,7-dimethyloctaneperoxoate Chemical compound CC(C)(C)CCCCCC(=O)OOC(C)(C)C NMOALOSNPWTWRH-UHFFFAOYSA-N 0.000 description 1
- SWAXTRYEYUTSAP-UHFFFAOYSA-N tert-butyl ethaneperoxoate Chemical compound CC(=O)OOC(C)(C)C SWAXTRYEYUTSAP-UHFFFAOYSA-N 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 238000010998 test method Methods 0.000 description 1
- 125000000383 tetramethylene group Chemical group [H]C([H])([*:1])C([H])([H])C([H])([H])C([H])([H])[*:2] 0.000 description 1
- 235000019303 thiodipropionic acid Nutrition 0.000 description 1
- 229940071127 thioglycolate Drugs 0.000 description 1
- 150000003573 thiols Chemical class 0.000 description 1
- 150000003606 tin compounds Chemical class 0.000 description 1
- JOXIMZWYDAKGHI-UHFFFAOYSA-N toluene-4-sulfonic acid Chemical compound CC1=CC=C(S(O)(=O)=O)C=C1 JOXIMZWYDAKGHI-UHFFFAOYSA-N 0.000 description 1
- 238000005829 trimerization reaction Methods 0.000 description 1
- QXJQHYBHAIHNGG-UHFFFAOYSA-N trimethylolethane Chemical compound OCC(C)(CO)CO QXJQHYBHAIHNGG-UHFFFAOYSA-N 0.000 description 1
- 229920002554 vinyl polymer Polymers 0.000 description 1
Classifications
-
- 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
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00355—Production of simple or compound lenses with a refractive index gradient
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29D—PRODUCING PARTICULAR ARTICLES FROM PLASTICS OR FROM SUBSTANCES IN A PLASTIC STATE
- B29D11/00—Producing optical elements, e.g. lenses or prisms
- B29D11/00009—Production of simple or compound lenses
- B29D11/00432—Auxiliary operations, e.g. machines for filling the moulds
- B29D11/00442—Curing the lens material
-
- 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
- C08G18/242—Catalysts containing metal compounds of tin organometallic compounds containing 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
- C08G18/08—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
- C08G18/28—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
- C08G18/3878—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus
- C08G18/3882—Low-molecular-weight compounds having heteroatoms other than oxygen having phosphorus having phosphorus bound to oxygen only
- C08G18/3885—Phosphate compounds
-
- 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
- C08G18/81—Unsaturated isocyanates or isothiocyanates
-
- 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
- C08G18/81—Unsaturated isocyanates or isothiocyanates
- C08G18/8108—Unsaturated isocyanates or isothiocyanates having only one isocyanate or isothiocyanate group
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/36—Sulfur-, selenium-, or tellurium-containing compounds
- C08K5/37—Thiols
-
- 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
- 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
-
- 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
- C08G2120/00—Compositions for reaction injection moulding processes
Definitions
- the present invention relates to a polymerizable composition for an optical material, an optical material, and a method for producing the optical material.
- Plastic lenses are lighter and harder to break than inorganic lenses, and can be dyed, so in recent years, they have rapidly spread to optical elements such as eyeglass lenses and camera lenses.
- a plastic material having a high refractive index is desired from the viewpoint of reducing the thickness of the lens
- a plastic material having a high Abbe number is desired from the viewpoint of reducing chromatic aberration.
- a plastic lens made of a polythiourethane resin obtained by reacting polythiol and a polyiso (thio) cyanate compound has a high refractive index and is excellent in impact resistance, dyeability, workability, and the like.
- Patent Document 1 discloses a polymerizable composition for an optical material containing phenylene diisocyanate and a predetermined polythiol compound, and an ultrahigh refractive index polythiourethane plastic lens having a refractive index of 1.7 or more obtained from the composition. It is disclosed.
- Patent Document 2 discloses an optical material polymerizable composition containing episulfide (thioepoxide), and an episulfide plastic lens having a refractive index of 1.7 or more obtained from the composition.
- Patent Document 3 discloses a polysulfide resin composition comprising a polythiol having 4 or more functional groups and a compound having a reactive unsaturated bond and / or an epoxy group and / or an iso (thio) cyanato group in one molecule.
- a polythioether-based transparent resin obtained from the composition.
- Patent Document 4 discloses a curable liquid unsaturated thiol compound, a method for producing the compound, and a method for producing a solid polythioether product using the compound.
- Example 1 describes an example in which a film was produced using pentaerythritol tetrakis (2-mercaptopropionate) and allyl isocyanate.
- the plastic lens obtained from the polymerizable composition for optical materials described in Patent Document 1 has a high refractive index, the Abbe number is low and the chromatic aberration may be relatively large. In other words, there was room for improvement in the Abbe number.
- the plastic lens obtained from the polymer composition for optical materials described in Patent Document 2 has a high refractive index and a high Abbe number, it is subjected to a two-point frame process in which holes are formed at both ends of the spectacle lens and held in the frame. However, there was room for improvement due to insufficient processability and strength.
- Patent Document 3 discloses an example of a specific combination of a compound having a carbon-carbon double bond, one or more groups selected from isocyanato groups and isothiocyanato groups, and a polythiol compound.
- the refractive index of the thiourethane material containing polyisocyanate is in the range of 1.58 to 1.63, and there is room for improvement in the refractive index. was there.
- Patent Document 4 does not relate to an optical material, and particularly does not disclose any plastic lens.
- the present invention has been made in view of such circumstances, and provides a thiourethane optical material having a higher refractive index, a higher Abbe number, an excellent balance of optical properties, and an excellent strength. Objective.
- A a compound having, in the molecule, a carbon-carbon double bond and one or more groups selected from an isocyanato group and an isothiocyanato group;
- B a polythiol compound;
- a polymerizable composition for an optical material comprising: [2]
- the compound (A) is represented by the following general formula (1) (In the formula (1), A 1 represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted phenylene group, n is an integer of 0 or 1, and R 1 is Represents an isocyanato group or an isothiocyanato group, and R 2 represents a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or the following formula (In the formula, A 2 and R 4 have the same meanings as A 1 and R 1 , respectively, and may be the same as or different from these groups.
- Compound (A) is represented by the following general formula (2) (In Formula (2), A 3 represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted phenylene group, R 5 represents an isocyanato group or an isothiocyanato group, and n represents It is an integer of 0 or 1.
- the polymerizable composition for optical materials represented by: [4]
- the polythiol compound (B) is Pentaerythritol tetrakis (3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-tri Thiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3 -Dithietane, 1,1,2,2-te
- polythiol compound (B) 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1 , 11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 1,1,3,3-tetrakis (mercapto Methylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane, 1,1,2,2-tetrakis [1] to [3], which are at least one selected from the group consisting of (mercaptomethylthio) ethane and 3-mercap
- the optical material for the polymerizable composition according to any one.
- the functional group molar ratio represented by (total number of isocyanato groups + total number of isothiocyanato groups + number of double bonds) / (total number of thiol groups) in the polymerizable composition is 0.5 to 2.0.
- an optical material having a high refractive index and a high Abbe number, an excellent balance of optical properties, and an excellent strength can be obtained.
- the polymerizable composition for optical materials of the present invention will be described with reference to embodiments.
- the polymerizable composition for an optical material of the present embodiment includes (A) a compound having, in the molecule, a carbon-carbon double bond and one or more groups selected from an isocyanato group and an isothiocyanate group, and (B And a polythiol compound.
- the present inventors have particularly a compound having a relatively small molecular weight and having at least one group selected from an isocyanato group and an isothiocyanato group and a carbon-carbon double bond in the molecule ( It has been found that an optical material having a high refractive index can be obtained by using A). Furthermore, it has been found that by using the compound (A) in combination with the polythiol compound (B), an optical material having a high refractive index and a high Abbe number and excellent in strength and the like can be obtained. The present invention has been completed based on such findings. Hereinafter, each component will be described.
- the compound (A) used in the present embodiment has a carbon-carbon double bond and one or more groups selected from an isocyanato group and an isothiocyanato group.
- the compound (A) can be represented by the following general formula (1).
- a 1 represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted phenylene group.
- substituent of the alkylene group having 1 to 4 carbon atoms which may be substituted include a monomethyl group and a dimethyl group.
- a methyl group etc. can be mentioned as a substituent of the phenylene group which may be substituted.
- a 1 is preferably a methylene group, an ethylene group, a propylene group, a butylene group, an o-phenylene group, a p-phenylene group, or an m-phenylene group.
- n is an integer of 0 or 1.
- R 1 represents an isocyanato group or an isothiocyanato group, preferably an isocyanato group.
- R 2 is a hydrogen atom, an alkyl group having 1 to 4 carbon atoms, or a group represented by the following formula.
- a 2 and R 4 have the same meanings as A 1 and R 1 , respectively, and may be the same as or different from these groups. * Indicates a bond.
- R 2 in the general formula (1) is preferably a hydrogen atom, a methyl group, or an isocyanatomethylene group.
- R 3 represents a hydrogen atom or a methyl group, preferably a hydrogen atom.
- a 3 represents an optionally substituted alkylene group having 1 to 4 carbon atoms or an optionally substituted phenylene group.
- substituent of the alkylene group having 1 to 4 carbon atoms which may be substituted include a monomethyl group and a dimethyl group.
- a methyl group etc. can be mentioned as a substituent of the phenylene group which may be substituted.
- a 3 is preferably a methylene group, an ethylene group or a phenylene group.
- R 5 represents an isocyanato group or an isothiocyanato group, preferably an isocyanato group.
- n is an integer of 0 or 1.
- Examples of the compound represented by the general formula (2) include allyl isocyanate, vinyl isocyanate, 2-methyl-2-propenyl isocyanate, 3-butenyl isocyanate, 2-butenyl isocyanate, vinyl phenylene isocyanate, allyl isothiocyanate, vinyl iso Examples include thiocyanate, 2-methyl-2-propenyl isothiocyanate, 3-butenyl isothiocyanate, 2-butenyl isothiocyanate, and vinylphenylene isothiocyanate. At least one of them can be used.
- the compound represented by the general formula (2) is a compound in which A 3 is a methylene group or a phenylene group, R 5 is an isocyanato group or an isothiocyanato group, and n is an integer of 0 or 1.
- Specific examples include at least one selected from the group consisting of allyl isocyanate, allyl isothiocyanate, vinyl isocyanate, vinyl phenylene isocyanate, and vinyl phenylene isothiocyanate.
- a compound in which A 3 is a methylene group, R 5 is an isocyanato group or isothiocyanato group, and n is an integer of 1 is particularly preferable, and specifically, a group consisting of allyl isocyanate and allyl isothiocyanate There may be mentioned at least one selected from By using the compound as described above as the compound (A) and using it in combination with the polythiol compound (B), it has a higher refractive index and a higher Abbe number, and is further excellent in the balance of optical properties, and has a high tensile strength. An optical material having further improved strength and the like can be suitably obtained.
- the polythiol compound (B) is a bifunctional or higher polythiol compound having one or more sulfide bonds and / or one or more ester bonds, and may be a single type or a mixture of two or more types of compounds.
- polythiol compound (B) Bifunctional or higher functional polythiol compound (b1) having one or more sulfide bonds (hereinafter sometimes abbreviated as “polythiol compound (b1)”), A bifunctional or more polythiol compound (b2) having one or more ester bonds (hereinafter sometimes abbreviated as “polythiol compound (b2)”); Bifunctional or higher polythiol compound (b3) having one or more ester bonds and one or more sulfide bonds (hereinafter sometimes abbreviated as “polythiol compound (b3)”) Can be mentioned.
- polythiol compound (B) examples include one or more compounds selected from compounds included in any one of the polythiol compounds (b1) to (b3), and any two of the polythiol compounds (b1) to (b3).
- One or more compounds selected from the included compounds, or one or more compounds selected from the compounds included in the polythiol compounds (b1) to (b3) can be given.
- the polythiol compound (B) is preferably one or more selected from the polythiol compound (b1) and the polythiol compound (b2), more preferably a compound selected only from the polythiol compound (b1).
- one or more compounds selected from compounds included in the polythiol compound (b1) and one or more compounds selected from compounds included in the polythiol compound (b2) can be used in combination.
- the polythiol compound (b1) is a compound having one or more sulfide bonds and two or more SH groups.
- Specific examples of the polythiol compound (b1) include 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-tri Thiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane Tetrakis (mercaptomethyl) methane, bis (mercaptomethyl) sulfide, 2,5-bis (mercaptomethyl) -1,4-dithiane, bis (mercaptomethyl) disulfide, bis (mercaptoethyl) sulfide, bis (mercaptoethyl) Disulfide
- polythiol compound (b1) 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto-3,6,9-tri Thiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane Bis (mercaptoethyl) sulfide, 2,5-bis (mercaptomethyl) -1,4-dithiane, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1 , 3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3-dithietane, 1,1,2,2-tetrakis (
- the polythiol compound (b2) is a compound having one or more ester bonds and two or more SH groups.
- Specific examples of the polythiol compound (b2) include 2,3-dimercapto-1-propanol (3-mercaptopropionate), 3-mercapto-1,2-propanediol bis (2-mercaptoacetate), 3- Mercapto-1,2-propanediol di (3-mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate), trimethylolpropane tris (3-mercaptopropionate), trimethylolethane tris (2-mercapto) Acetate), trimethylolethane tris (3-mercaptopropionate), pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), pentaerythritol bis (3-mercap) Propionate), pentaerythri
- l, m, and r independently represent an integer of 1 to 4, and n represents an integer of 1 to 3.
- R represents hydrogen or a methyl group, and when a plurality of Rs are present, they may be the same or different.
- l and m each independently represents an integer of 1 to 2, r is preferably an integer of 1 to 3, and n is preferably 1 or 2.
- the polythiol compound represented by the general formula (3) is a condensate of ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol and mercaptoalkylcarboxylic acid.
- Triethylene glycol bis (mercaptopropionate) triethylene glycol bis (mercaptobutyrate), bis (3-mer (Captopropionic acid) 1,4-butanediol and the like.
- it can use 1 type or in combination of 2 or more types.
- diethylene glycol bis (mercaptopropionate) or bis (3-mercaptopropionic acid) 1,4-butanediol can be preferably used.
- the polythiol compound (b2) is selected from the group consisting of pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), and the polythiol compound represented by the general formula (3). It is preferable that there is at least one.
- the polythiol compound (b2) is more preferably pentaerythritol tetrakis (3-mercaptopropionate), diethylene glycol bis (mercaptopropionate), bis (3-mercaptopropionic acid) 1,4-butane. Diols can be used.
- the polythiol compound (b3) is a compound having one or more ester bonds and one or more sulfide bonds and having two or more SH groups.
- Specific examples of the polythiol compound (b3) include 2,2′-thiodiethanol bis (2-mercaptoacetate), 2,2′-thiodiethanol bis (3-mercaptopropionate), thiodimethanol bis (2 -Mercaptoacetate), thiodimethanol bis (3-mercaptopropionate) and the like. Among these, it can use 1 type or in combination of 2 or more types.
- polythiol compound (B) pentaerythritol tetrakis (3-mercaptopropionate), 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane, 5,7-dimercaptomethyl-1,11-dimercapto -3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11-dimercapto-3 , 6,9-trithiaundecane, 1,1,3,3-tetrakis (mercaptomethylthio) propane, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercapto) Methylthio) ethyl) -1,3-dithietane, 1,1,2,2-tetrakis (mercaptomethylthio) ethane
- the polymerizable composition for an optical material of the present embodiment includes a reaction catalyst, a radical polymerization initiator, a polyisocyanate compound, an isocyanate compound having an isothiocyanato group, or a polyisothiocyanate in addition to the compound (A) and the polythiol compound (B).
- a compound, a substituted or modified product of an isocyanate compound, a thiol compound having a mercapto group or an amino group, a polyol compound, a polyamine compound, and the like can be included.
- reaction catalyst examples include tin compounds such as dibutyltin dilaurate, dibutyltin dichloride, and dimethyltin dichloride, and amine compounds such as tertiary amines. One or two or more can be used in combination. A known urethanization catalyst or thiourethanization catalyst can be used.
- the amount of the reaction catalyst used is not particularly limited, but is usually in the range of 0 to 10 parts by weight with respect to 100 parts by weight of the polymerizable component.
- the radical polymerization initiator is not particularly limited as long as it is sensitive to heat or active energy rays such as ultraviolet rays.
- heat polymerization conventionally known organic peroxides and azo compounds can be used. Although depending on the heating conditions, compounds having a 10-hour half-life temperature of 120 ° C. or lower are usually preferred.
- cumyl peroxyneodecanoate di-n-propyl peroxydicarbonate, di (2-ethylhexyl) Peroxydicarbonate, t-butylperoxyneodecanoate, 2,4-dichlorobenzoyl peroxide, lauroyl peroxide, acetyl peroxide, t-butylperoxy-2-ethylhexanoate, benzoyl peroxide, t -Butyl peroxyisobutyrate, t-butyl peroxylaurate, t-butyl peroxy-3,5,5-trimethylhexanoate, t-butyl peroxyisopropyl carbonate, t-butyl peroxyacetate, t- Butyl peroxybenzoate, methyl ether Le ketone peroxide, dicumyl peroxide, and the like t- butyl cumyl peroxide.
- azo compound examples include azobisisobutyronitrile, 2,2′-azobis (4-methoxy-2,4-dimethylvaleronitrile), azobis (methylbutylnitrile), and the like. These catalysts may be used individually by 1 type, and may use 2 or more types together. The reaction catalyst and the radical polymerization initiator may be used alone or in combination.
- Polyisocyanate compounds include hexamethylene diisocyanate, 2,2,4-trimethylhexane diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate, lysine diisocyanatomethyl ester, lysine triisocyanate, m-xylylene diisocyanate, ⁇ , ⁇ , ⁇ ', ⁇ '-tetramethylxylylene diisocyanate, bis (isocyanatomethyl) naphthalene, mesityrylene triisocyanate, bis (isocyanatomethyl) sulfide, bis (isocyanatoethyl) sulfide, bis (isocyanatomethyl) Disulfide, bis (isocyanatoethylthio) disulfide, bis (isocyanatomethylthio) methane, bis (isocyanatoethylthio) methane, bis (isocyanatoethylthi
- Examples of the isocyanate compound having an isothiocyanate group include those obtained by changing a part of the isocyanato group of the polyisocyanate compound exemplified above to an isothiocyanate group.
- Polyisothiocyanate compounds include hexamethylene diisothiocyanate, lysine diisothiocyanate methyl ester, lysine triisothiocyanate, m-xylylene diisothiocyanate, bis (isothiocyanatomethyl) sulfide, bis (isothiocyanatoethyl) sulfide Aliphatic polyisothiocyanate compounds such as bis (isothiocyanatoethyl) disulfide; Isophorone diisothiocyanate, bis (isothiocyanatomethyl) cyclohexane, dicyclohexylmethane diisothiocyanate, cyclohexane diisothiocyanate, methylcyclohexane diisothiocyanate, 2,5-bis (isothiocyanatomethyl) bicyclo- [2.2.1 ] -Heptane, 2,6-bis (isothiocyan
- halogen-substituted products such as chlorine-substituted products and bromine-substituted products of these isocyanate compounds, alkyl-substituted products, alkoxy-substituted products, nitro-substituted products, prepolymer-modified products with polyhydric alcohols, carbodiimide-modified products, and urea-modified products.
- Biuret modified products, dimerization or trimerization reaction products, and the like can also be used.
- Examples of the thiol compound having a hydroxy group include 2-mercaptoethanol, 3-mercapto-1,2-propanediol, glycerin bis (mercaptoacetate), 4-mercaptophenol, 2,3-dimercapto-1-propanol, penta Examples include erythritol tris (3-mercaptopropionate) and pentaerythritol tris (thioglycolate). Examples of the thiol compound having an amino group include aminoethanethiol.
- the polymerizable composition for an optical material according to the present embodiment is prepared by using, as necessary, a UV absorber such as a benzotriazole type, an internal release agent such as an acidic phosphate, Substances such as a stabilizer, an antioxidant, a chain extender, a crosslinking agent, an anti-coloring agent, an oil-soluble dye, and a filler may be added.
- a UV absorber such as a benzotriazole type
- an internal release agent such as an acidic phosphate
- Substances such as a stabilizer, an antioxidant, a chain extender, a crosslinking agent, an anti-coloring agent, an oil-soluble dye, and a filler may be added.
- the optical material of this embodiment can be manufactured by the following steps. In the following, the case where the optical material is a plastic spectacle lens will be described.
- the manufacturing method of the optical material of this embodiment includes the manufacturing method of the polymeric composition for optical materials as a process (a). Step (a): Compound (A) and polythiol compound (B) are mixed to prepare a polymerizable composition for an optical material. Step (b): The polymerizable composition is poured into a lens casting mold. Step (c): The polymerizable composition is polymerized and cured in the mold.
- Step (a) In the step (a), the compound (A) and the polythiol compound (B) are mixed, and if necessary, various polymerizable compounds are used in combination. The method of mixing and dissolving after adding various additives is mentioned.
- the compound (A) and the polythiol compound (B) include NCO: the number of moles of functional groups of all isocyanate groups in the polymerizable composition containing the compound (A).
- NCS contains the compound (A) It is represented by (NCO + NCS + double bond number) / (SH), where the functional group moles of all isothiocyanato groups in the polymerizable composition are SH: the functional group moles of mercapto groups in all polythiol compounds including the compound (B).
- the functional group molar ratio can be used in the range of 0.5 to 2.0, preferably in the range of 0.5 to 1.5. If it is the said range, it will become rubbery at the time of hardening, the deterioration of a hue, etc. are suppressed, and the molded object suitable for an optical material use can be obtained.
- the temperature at the time of mixing is set suitably, it may be preferable to make it low temperature from a viewpoint of the pot life of polymeric composition.
- additives such as a catalyst and a release agent do not show good solubility in the compound (A), the polythiol compound (B), and other polymerizable compounds
- the compound is heated in advance. It may be dissolved in (A) and the polythiol compound (B) or a mixture thereof.
- the mixing order and mixing method of each component in the composition are not particularly limited as long as each component can be uniformly mixed, and can be performed by a known method.
- Step (b) the polymerizable composition for an optical material obtained in the step (a) is injected into a lens casting mold held by a gasket or a tape.
- a gasket or a tape it is preferable to carry out defoaming treatment under reduced pressure, filtration treatment under pressure, reduced pressure, etc., if necessary.
- Step (c) In the step (c), after the composition is injected, the lens casting mold is cured by heating it for several hours to several tens of hours with a predetermined temperature program in a heatable apparatus such as an oven or water. Mold.
- the polymerization curing temperature is not limited because the conditions vary depending on the composition of the polymerizable composition, the type of catalyst, the shape of the mold, etc., but is approximately 1 to 100 hours at a temperature of ⁇ 50 to 200 ° C. Usually, it is started at a temperature in the range of 5 ° C. to 40 ° C., and then gradually raised to a range of 80 ° C. to 130 ° C. for curing.
- the plastic spectacle lens of this embodiment can be obtained by taking out from the lens casting mold after completion of the curing molding.
- the annealing temperature is usually in the range of 80 to 150 ° C., preferably in the range of 100 to 130 ° C., more preferably in the range of 110 to 130 ° C.
- the annealing time is usually in the range of 0.5 to 5 hours, preferably in the range of 1 to 4 hours.
- the plastic spectacle lens of this embodiment is used with a coating layer on one side or both sides as required.
- the coating layer include a primer layer, a hard coat layer, an antireflection film layer, an antifogging coat layer, a stainproof layer, and a water repellent layer. These coating layers may be used singly or in a multilayered form. When a coating layer is applied to both sides, a similar coating layer or a different coating layer may be applied to each surface.
- Each of these coating layers contains an ultraviolet absorber for the purpose of protecting the lens and eyes from ultraviolet rays, an infrared absorber for the purpose of protecting the eyes from infrared rays, a light stabilizer and an antioxidant for the purpose of improving the weather resistance of the lens, Dyes and pigments for the purpose of enhancing the fashionability of the lens, photochromic dyes and photochromic pigments, antistatic agents, and other known additives may be used in combination for the purpose of enhancing the performance of the lens. Various leveling agents may be used for the purpose of improving coatability.
- the plastic spectacle lens of the present embodiment may be subjected to back surface polishing, antistatic treatment, dyeing treatment, light control treatment, and the like as necessary.
- the plastic spectacle lens of the present embodiment thus obtained has a high refractive index, and the refractive index of e-line is in the range of 1.6 to 1.8.
- the optical material of the present invention has been described as an example of using as a plastic spectacle lens.
- eyeglass lenses for correcting vision lenses for imaging devices, Fresnel lenses for liquid crystal projectors, lenticular lenses, contact lenses, and other plastic lenses, light emission Sealing materials for diodes (LEDs), optical waveguides, optical adhesives used for bonding optical lenses and optical waveguides, antireflection films used for optical lenses, liquid crystal display device members (substrates, light guide plates, films, sheets, etc.) It can also be used as a transparent coating or a transparent substrate used in the above.
- the lens obtained by polymerization was evaluated by performing a performance test.
- the refractive index / Abbe number and specific gravity were evaluated and evaluated by the following test methods.
- Refractive index (ne) Abbe number ( ⁇ e) Measured at 20 ° C. using a Purfrich refractometer KPR-30 manufactured by Shimadzu Corporation.
- Specific gravity Measured by Archimedes method at 20 ° C.
- Bending test Measured by AUTOGRAPH AGS-J manufactured by Shimadzu Corporation.
- polythiol compound A After removing the solvent to remove chloroform and low-boiling components, 340.0 g of polythiol compound A was obtained after filtration through a 3 ⁇ m Teflon (registered trademark) filter. Two other polythiol compound components were detected by LC analysis of polythiol compound A (9.8% and 9.8% in chromatogram area ratio, respectively). When these components were purified and analyzed by preparative LC, 4,6-bis (mercaptomethylthio) -1,3-dithiane, 2- (2,2-bis (mercaptomethylthio) ethyl) -1,3- Dithietan. The analysis results are shown below. Moreover, the thiol equivalent of the polythiol compound A was measured by the following method.
- a 0.05 mol / L iodine solution was gradually added dropwise to a mixed solvent solution of 95.1 mg of polythiol compound A in 30 ml of chloroform and 30 ml of methanol.
- 9.7 ml was added dropwise, the brown color of the dropped iodine did not disappear, and the amount of SH groups contained in the polythiol compound A was calculated using this point as the equivalent point, resulting in 9.64 meq / g.
- Example 1 32 parts by weight of allyl isocyanate represented by Compound No. 1-1 (manufactured by Tokyo Chemical Industry Co., Ltd.), polythiol compound A synthesized by the method described in Production Example 1 as a thiol compound, (1,1,3,3-tetrakis ( 68 parts by weight of polythiol compound based on mercaptomethylthio) propane), 150 ppm of dimethyltin dichloride, 2500 ppm of “perbutyl (R) O”, 1500 ppm of a 1: 9 mixture of monobutyl phosphoric acid and dibutyl phosphoric acid are mixed and dissolved at room temperature.
- Examples 2 to 9 The same operation as in Example 1 was performed except that the composition shown in Table 1 was changed. The composition and evaluation results are shown in Table 1. In addition, the molded body obtained in Example 2 was subjected to a bending test and a punching tensile test. The results are shown in Table-2.
- the catalyst is dimethyltin dichloride 100 ppm, Zelec-UN (product name: Stepan); 1500 ppm, m-xylene diisocyanate 44 parts by weight, 1,1,3,3-tetrakis (mercaptomethylthio) 56 parts by weight of polythiol compound A mainly composed of propane was charged and stirred at room temperature and mixed. The mixed compound is degassed under reduced pressure, and the polymerizable composition is poured into a mold composed of a glass mold and a tape, then placed in a heating oven and gradually heated to 25-120 ° C. and polymerized for 20 hours. Went. The obtained molded article had good transparency and good appearance without distortion, but the Abbe number was 30. The evaluation results are shown in Table-1.
- the mixed compound is degassed under reduced pressure, and the polymerizable composition is poured into a mold composed of a glass mold and a tape, then placed in a heating oven and gradually heated to 25-120 ° C. and polymerized for 20 hours. Went.
- the obtained molded article had good transparency and good appearance without distortion, but the Abbe number was 31.
- the evaluation results are shown in Table-1.
- an internal mold release agent trade name: Zelec-UN (Product name, Stepan product) 1200 ppm
- UV absorber Product name: Viosorb-583, Kyodo Yakuhin Co., Ltd. product
- Example 1 to 6 and Comparative Example 1 and Example 7 and Comparative Example 2 revealed that “in the molecule, a carbon-carbon double bond and one or more groups selected from isocyanato groups and isothiocyanato groups”
- the compound (A) having a high refractive index a molded article having a high Abbe number was obtained. Furthermore, similar results were obtained even when different thiol compounds were used as in Example 8.
- Example 9 and Comparative Example 3 were compared, a molded product having a higher Abbe number was obtained in Example 9 while having the same refractive index.
- the molded product obtained by the present invention was a molded product that was excellent in terms of tensile strength and the like.
- a polymerizable composition for an optical material containing, in the molecule, a compound (A) having a carbon-carbon double bond, one or more groups selected from isocyanato groups and isothiocyanato groups, and a polythiol compound (B). From the product, it was possible to obtain a thiourethane optical material that was excellent in strength and the like, had a high refractive index and at the same time had a high Abbe number.
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Abstract
Description
特許文献2には、エピスルフィド(チオエポキシド)を含む光学材料重合性組成物が開示されており、該組成物から得られた屈折率1.7以上のエピスルフィド系プラスチックレンズが開示されている。
特許文献4には、硬化性の液体不飽和チオール化合物、その製造方法および該化合物を用いた固体ポリチオエーテル製品の製造方法が開示されている。実施例1には、ペンタエリスリトールテトラキス(2-メルカプトプロピオネート)とアリルイソシアネートとを用いて、フィルムが製造された例が記載されている。
本発明は、このような事情に鑑みてなされたものであり、より高屈折率であり、よりアッベ数が高く光学物性のバランスに優れ、強度にも優れたチオウレタン光学材料を提供することを目的とする。
[1] (A)分子内に、炭素-炭素二重結合と、イソシアナト基およびイソチオシアナト基から選択される1以上の基と、を有する化合物と、
(B)ポリチオール化合物と、
を含む、光学材料用重合性組成物。
[2] 化合物(A)は、下記一般式(1)
で表される、[1]に記載の光学材料用重合性組成物。
[3]化合物(A)は、下記一般式(2)
[4] ポリチオール化合物(B)は、
ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタンおよび3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタンよりなる群から選ばれる少なくとも1種である、[1]乃至[3]のいずれかに記載の光学材料用重合性組成物。
[5] ポリチオール化合物(B)は、
4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタンおよび3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタンよりなる群から選ばれる少なくとも1種である、[1]乃至[3]のいずれかに記載の光学材料用重合性組成物。
[6]重合性組成物中の(全イソシアナト基数+全イソチオシアナト基数+2重結合数)/(全チオール基数)で表される官能基モル比が、0.5~2.0である、[1]乃至[5]のいずれかに記載の光学材料用重合性組成物。
[7] 化合物(A)とポリチオール化合物(B)とを混合し、[1]乃至[6]のいずれかに記載の光学材料用重合性組成物を調製する工程と、
前記重合性組成物を、注型用鋳型内に注入する工程と、
前記鋳型内で、前記重合性組成物を重合硬化する工程と、
を含む、光学材料の製造方法。
[8] [7]に記載の製造方法で得られた光学材料。
[9] e線の屈折率が1.6~1.8の範囲である[8]に記載の光学材料。
[10] [8]または[9]に記載の光学材料からなる、プラスチック眼鏡レンズ。
本実施形態の光学材料用重合性組成物は、(A)分子内に、炭素-炭素二重結合と、イソシアナト基およびイソチオシアナト基から選択される1以上の基と、を有する化合物と、(B)ポリチオール化合物と、を含む。
以下、各成分について説明する。
本実施形態において用いられる化合物(A)は、炭素-炭素二重結合と、イソシアナト基およびイソチオシアナト基から選択される1以上の基と、を有する。
化合物(A)は、下記一般式(1)で表すことができる。
置換されてもよい炭素数1~4のアルキレン基の置換基としては、モノメチル基、ジメチル基等を挙げることができる。置換されてもよいフェニレン基の置換基としては、メチル基等を挙げることができる。
A1として好ましくは、メチレン基、エチレン基、プロピレン基、ブチレン基、o-フェニレン基、p-フェニレン基、m-フェニレン基である。
式(1)中、nは0もしくは1の整数である。
式(1)中、R1は、イソシアナト基またはイソチオシアナト基を示し、好ましくはイソシアナト基である。
式(1)中、R2は水素原子、炭素数1~4のアルキル基、または下記式で表される基である。
一般式(1)のR2として、好ましくは、水素原子、メチル基、またはイソシアナトメチレン基である。
式(1)中、R3は水素原子、メチル基を示し、好ましくは水素原子ある。
置換されてもよい炭素数1~4のアルキレン基の置換基としては、モノメチル基、ジメチル基等を挙げることができる。置換されてもよいフェニレン基の置換基としては、メチル基等を挙げることができる。A3として好ましくは、メチレン基、エチレン基、フェニレン基である。
R5は、イソシアナト基またはイソチオシアナト基を示し、好ましくはイソシアナト基である。
nは0もしくは1の整数である。
これらのうちでも、A3がメチレン基であり、R5がイソシアナト基またはイソチオシアナト基であり、nが1の整数である化合物が特に好ましく、具体的には、アリルイソシアネートおよびアリルイソチオシアネートよりなる群から選ばれる少なくとも1種を挙げることができる。
化合物(A)として上記のような化合物を用い、ポリチオール化合物(B)と組み合わせて用いることにより、より高屈折率を有すると同時により高アッベ数であり、光学物性のバランスにさらに優れるとともに、引っ張り強度等がさらに改善された光学材料を好適に得ることができる。
ポリチオール化合物(B)は、1以上のスルフィド結合および/または1以上のエステル結合を有する二官能以上のポリチオール化合物であり、一種類または二種類以上の化合物の混合物でもよい。
ポリチオール化合物(B)として、具体的には、
1以上のスルフィド結合を有する二官能以上のポリチオール化合物(b1)(以下、「ポリチオール化合物(b1)」と略することもある。)、
1以上のエステル結合を有する二官能以上のポリチオール化合物(b2)(以下、「ポリチオール化合物(b2)」と略することもある。)、
1以上のエステル結合および1以上のスルフィド結合を有する二官能以上のポリチオール化合物(b3)(以下、「ポリチオール化合物(b3)」と略することもある。)
を挙げることができる。
本実施形態において、ポリチオール化合物(B)は、ポリチオール化合物(b1)とポリチオール化合物(b2)から選択される一種以上を用いることが好ましく、より好ましくは、ポリチオール化合物(b1)からのみ選択される化合物、または、ポリチオール化合物(b1)に含まれる化合物から選択される一種以上の化合物と、ポリチオール化合物(b2)に含まれる化合物から選択される一種以上の化合物と、を組み合わせて用いることができる。
ポリチオール化合物(b1)として、具体的には、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、テトラキス(メルカプトメチル)メタン、ビス(メルカプトメチル)スルフィド、2,5-ビス(メルカプトメチル)-1,4-ジチアン、ビス(メルカプトメチル)ジスルフィド、ビス(メルカプトエチル)スルフィド、ビス(メルカプトエチル)ジスルフィド、ビス(メルカプトメチルチオ)メタン、ビス(2-メルカプトエチルチオ)メタン、1,2-ビス(メルカプトメチルチオ)エタン、1,2-ビス(2-メルカプトエチルチオ)エタン、1,3-ビス(メルカプトメチルチオ)プロパン、1,3-ビス(2-メルカプトエチルチオ)プロパン、1,2,3-トリス(メルカプトメチルチオ)プロパン、1,2,3-トリス(2-メルカプトエチルチオ)プロパン、1,2,3-トリス(3-メルカプトプロピルチオ)プロパン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、テトラキス(メルカプトメチルチオメチル)メタン、テトラキス(2-メルカプトエチルチオメチル)メタン、ビス(2,3-ジメルカプトプロピル)スルフィド、1,1,2,2-テトラキス(メルカプトメチルチオ)エタン、3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタン等を挙げることができ、少なくとも1種を用いることができる。
ポリチオール化合物(b2)として、具体的には、2,3-ジメルカプト-1-プロパノール(3-メルカプトプロピオネート)、3-メルカプト-1,2-プロパンジオールビス(2-メルカプトアセテート)、3-メルカプト-1,2-プロパンジオールジ(3-メルカプトプロピオネート)、トリメチロールプロパントリス(2-メルカプトアセテート)、トリメチロールプロパントリス(3-メルカプトプロピオネート)、トリメチロールエタントリス(2-メルカプトアセテート)、トリメチロールエタントリス(3-メルカプトプロピオネート)、ペンタエリスリトールテトラキス(2-メルカプトアセテート)、ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、ペンタエリスリトールビス(3-メルカプトプロピオネート)、ペンタエリスリトールトリス(3-メルカプトプロピオネート)、グリセリントリス(2-メルカプトアセテート)、グリセリントリス(3-メルカプトプロピオネート)、1,4-シクロヘキサンジオールビス(2-メルカプトアセテート)、1,4-シクロヘキサンジオールビス(3-メルカプトプロピオネート)、ヒドロキシメチルスルフィドビス(2-メルカプトアセテート)、ヒドロキシメチルスルフィドビス(3-メルカプトプロピオネート)、チオグリコール酸ビス(2-メルカプトエチルエステル)、チオジプロピオン酸ビス(2-メルカプトエチルエステル)、ヒドロキシエチルスルフィド(2-メルカプトアセテート)、ヒドロキシエチルスルフィド(3-メルカプトプロピオネート)、下記一般式(3)で表されるポリチオール化合物等が挙げられる。
ポリチオール化合物(b3)として、具体的には、2,2´-チオジエタノールビス(2-メルカプトアセテート)、2,2´-チオジエタノールビス(3-メルカプトプロピオネート)、チオジメタノールビス(2-メルカプトアセテート)、チオジメタノールビス(3-メルカプトプロピオネート)等を挙げることができる。これらのうちから1種または2種以上組み合わせて用いることができる。
4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタンおよび3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタンよりなる群から選ばれる少なくとも1種であることが特に好ましい。
このようなポリチオール化合物(B)を、上記のような化合物(A)と組み合わせて用いることにより、より高屈折率な光学材料を得ることができ、さらに高アッベ数であって光学物性のバランスに優れるとともに、引っ張り強度等がさらに改善された光学材料を好適に得ることができる。
本実施形態の光学材料用重合性組成物は、上記の化合物(A)およびポリチオール化合物(B)以外に、反応触媒、ラジカル重合開始剤、ポリイソシアネート化合物、イソチオシアナト基を有するイソシアネート化合物またはポリイソチオシアネート化合物、イソシアネート化合物の置換体や変性体、メルカプト基やアミノ基を有するチオール化合物、ポリオール化合物、ポリアミン化合物等を含むことができる。
反応触媒の使用量は、特に限定されるものではないが、通常、重合性成分100重量部に対して0~10重量部の範囲である。
反応触媒とラジカル重合開始剤とは、単独で使用してもよいし、両方を併用してもよい。
イソホロンジイソシアネート、ビス(イソシアナトメチル)シクロヘキサン、ジシクロヘキシルメタンジイソシアネート、シクロヘキサンジイソシアネート、メチルシクロヘキサンジイソシアネート、ジシクロヘキシルジメチルメタンイソシアネート、2,5-ビス(イソシアナトメチル)ビシクロ-[2.2.1]-ヘプタン、2,6-ビス(イソシアナトメチル)ビシクロ-[2.2.1]-ヘプタン、3,8-ビス(イソシアナトメチル)トリシクロデカン、3,9-ビス(イソシアナトメチル)トリシクロデカン、4,8-ビス(イソシアナトメチル)トリシクロデカン、4,9-ビス(イソシアナトメチル)トリシクロデカン等の脂環族ポリイソシアネート化合物;
ジフェニルスルフィド-4,4-ジイソシアネート等の芳香族ポリイソシアネート化合物;
2,5-ジイソシアナトチオフェン、2,5-ビス(イソシアナトメチル)チオフェン、2,5-ジイソシアナトテトラヒドロチオフェン、2,5-ビス(イソシアナトメチル)テトラヒドロチオフェン、3,4-ビス(イソシアナトメチル)テトラヒドロチオフェン、2,5-ジイソシアナト-1,4-ジチアン、2,5-ビス(イソシアナトメチル)-1,4-ジチアン、4,5-ジイソシアナト-1,3-ジチオラン、4,5-ビス(イソシアナトメチル)-1,3-ジチオラン等の複素環ポリイソシアネート化合物等を挙げることができる。
イソホロンジイソチオシアネート、ビス(イソチオシアナトメチル)シクロヘキサン、ジシクロヘキシルメタンジイソチオシアネート、シクロヘキサンジイソチオシアネート、メチルシクロヘキサンジイソチオシアネート、2,5-ビス(イソチオシアナトメチル)ビシクロ-[2.2.1]-ヘプタン、2,6-ビス(イソチオシアナトメチル)ビシクロ-[2.2.1]-ヘプタン、3,8-ビス(イソチオシアナトメチル)トリシクロデカン、3,9-ビス(イソチオシアナトメチル)トリシクロデカン、4,8-ビス(イソチオシアナトメチル)トリシクロデカン、4,9-ビス(イソチオシアナトメチル)トリシクロデカン等の脂環族ポリイソチオシアネート化合物;
ジフェニルジスルフィド-4,4-ジイソチオシアネート等の芳香族ポリイソチオシアネート化合物;
2,5-ジイソチオシアナトチオフェン、2,5-ビス(イソチオシアナトメチル)チオフェン、2,5-ジイソチオシアナトテトラヒドロチオフェン、2,5-ビス(イソチオシアナトメチル)テトラヒドロチオフェン、3,4-ビス(イソチオシアナトメチル)テトラヒドロチオフェン、2,5-ジイソチオシアナト-1,4-ジチアン、2,5-ビス(イソチオシアナトメチル)-1,4-ジチアン、4,5-ジイソチオシアナト-1,3-ジチオラン、4,5-ビス(イソチオシアナトメチル)-1,3-ジチオラン等の含硫複素環ポリイソチオシアネート化合物等を挙げることができる。
ヒドロキシ基を有するチオール化合物としては、例えば、2-メルカプトエタノール、3-メルカプト-1,2-プロパンジオール、グリセリンビス(メルカプトアセテート)、4-メルカプトフェノール、2,3-ジメルカプト-1-プロパノール、ペンタエリスリトールトリス(3-メルカプトプロピオネート)、ペンタエリスリトールトリス(チオグリコレート)等を挙げることができる。
アミノ基を有するチオール化合物としては、アミノエタンチオール等を挙げることができる。
本実施形態の光学材料は、以下の工程により製造することができる。以下においては、光学材料が、プラスチック眼鏡レンズである場合により説明する。なお、本実施形態の光学材料の製造方法は、光学材料用重合性組成物の製造方法を工程(a)として含む。
工程(a):化合物(A)とポリチオール化合物(B)とを混合して、光学材料用重合性組成物を調製する。
工程(b):前記重合性組成物を、レンズ注型用の鋳型内に注入する。
工程(c):前記鋳型内で、前記重合性組成物を重合硬化する。
工程(a)においては、化合物(A)とポリチオール化合物(B)とを混合して、さらに必要に応じて種々の重合性化合物を併用して、調整した混合液に、触媒、必要に応じて種々の添加剤を加えた後、混合、溶解させる方法が挙げられる。
上記範囲であれば、硬化時にゴム状となったり、色相の悪化などが抑制され、光学材料用途に適した成形体を得ることができる。
組成物中の各成分の混合順序や混合方法は、各成分を均一に混合することができれば特に限定されず、公知の方法で行うことができる。公知の方法としては、例えば、添加剤を所定量含むマスターバッチを作製して、このマスターバッチを溶媒に分散・溶解させる方法などがある。
また、化合物(A)とポリチオール化合物(B)の一部を反応させた化合物を用いてもよい。
工程(b)においては、ガスケットまたはテープ等で保持されたレンズ注型用鋳型内に、工程(a)で得られた光学材料用重合性組成物を注入する。
得られるプラスチック眼鏡レンズに要求される物性によっては、必要に応じて、減圧下での脱泡処理や加圧、減圧等での濾過処理等を予め行っておくことが好ましい。
工程(c)においては、組成物が注入された後、レンズ注型用鋳型をオーブン中または水中等の加熱可能装置内で所定の温度プログラムにて数時間から数十時間かけて加熱して硬化成型する。
さらに、本実施形態のプラスチック眼鏡レンズは、必要に応じ、裏面研磨、帯電防止処理、染色処理、調光処理等を施してもよい。
このようにして得られた本実施形態のプラスチック眼鏡レンズは高屈折率であり、e線の屈折率が1.6~1.8の範囲にある。
重合により得られたレンズは性能試験を行い評価した。性能試験は、屈折率・アッベ数、比重とし、以下の試験法により評価した。
・ 屈折率(ne)アッベ数(νe): 島津製作所社製、プルフリッヒ屈折計KPR-30を用いて、20℃で測定した。
・ 比重:20℃にてアルキメデス法により測定した。
・ 曲げ試験:島津製作所製AUTOGRAPH AGS-Jにより測定した。厚さ3.0mm、長さ75mm、幅25.0mmの樹脂試験片を用いて、試験片中央に下降速度1.2mm/minにて荷重を負荷させた時の最大点応力(N/mm2)を測定した。
・ 引張り強度試験:レンズ径45mm、厚さ2.5mmに調製された樹脂平板に、ツーポイントフレーム加工を想定して、ドリルにて両端の2箇所に直径1.6mmの穴を開けた。そして、島津製作所製AUTOGRAPH AGS-Jを用いて、1.6mmの金属製シャフトを穴に通し、サンプルの両端を固定治具に取り付けた後、5の速度で引張り、最大点の試験力を測定した。得られた最大点試験力を樹脂平板の厚さで割った値(kgf/mm)を算出した。
特開2004-2820号公報の製造例2に記載の方法に準拠して、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分として含むポリチオール化合物Aを合成した。
攪拌羽根、温度計、蒸留塔、窒素導入用キャピラリーを設置した2リットル底抜きコック付きフラスコに、1,1,3,3-テトラメトキシプロパン164.2 g(1 mol)、アセチルチオメチルチオール488.8 g(4 mol)およびパラトルエンスルホン酸7.6 g(0.04 mol)を加え、1kPa以下の真空度を保ち且つ攪拌しながら40℃に加熱した。メタノールの留出が停止するまで18時間程加熱を続けた。冷却後、真空を解除し、蒸留塔の代わりにコンデンサーを取り付けた後、メタノール400mlとクロロホルム400mlおよび36%塩酸200mlを加え、60℃に加熱してアルコリシスを行い、目的化合物である1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分として含むポリチオール化合物Aを合成した。
適量の水およびクロロホルムを加えて分液させ、クロロホルム層を数回水洗した。脱溶媒してクロロホルムおよび低沸分を除いた後、3μmテフロン(登録商標)フィルターで濾過後340.0 gのポリチオール化合物Aを得た。ポリチオール化合物AのLC分析により、その他ポリチオール化合物成分が2成分検出された(クロマトグラム面積比でそれぞれ9.8%、9.8%)。これらの成分を分取LCによって精製し分析したところ、それぞれ4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタンであった。以下に分析結果を示す。
また、ポリチオール化合物Aのチオール当量を以下の方法により測定した。ポリチオール化合物A 95.1 mgのクロロホルム30ml、メタノール30ml混合溶媒溶液に0.05mol/Lヨウ溶液を徐々に滴下した。9.7mlを滴下した時点で、滴下したヨウ素の褐色が消失しなくなり、この点を当量点としてポリチオール化合物Aに含まれるSH基の量を算出した結果、9.64meq/gであった。
1H-NMR δ(CDCl3):2.18(t, 4H)、2.49(t, 2H)、3.78-3.90(m, 8H)、4.64(t, 2H)
13C-NMR δ(CDCl3):26.7, 41.3, 48.7
FT-IR :538cm-1
MS :m/z=356(M+)
1H-NMR δ(CDCl3):2.02(t, 2H)、2.56(t, 2H)、3.77-3.91(m, 8H)、3.97(s, 2H)、4.66(t, 2H)
13C-NMR δ(CDCl3):27.1, 28.8, 38.1, 44.6
FT-IR :2538cm-1
MS:m/z=276(M+)
1H-NMR δ(CDCl3):2.03(t, 2H)、2.13-2.21(m, 1H)、2.75-2.80(m, 1H)、3.79-3.84(m, 1H)、3.90-3.96(m, 3H)、4.32-4.35(m, 2H)
13C-NMR δ(CDCl3):27.2, 32.3, 38.9, 46.2
FT-IR:2538cm-1
MS :m/z=276(M+)
化合物No.1-1で表されるアリルイソシアネート(東京化成社製)32重量部、チオール化合物として製造例1記載の方法にて合成したポリチオール化合物A、(1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とするポリチオール化合物)68重量部、ジメチル錫ジクロリド150ppm、「パーブチル(R)O」2500ppm、モノブチルリン酸とジブチルリン酸の1:9混合物1500ppmを室温にて混合溶解させてPTFE製フィルターで減圧濾過した後、150kPa~200kPaの減圧下に発泡が認められなくなるまで十分脱気させた。続いて、ガラスモールドとテープよりなるモールド中へ該重合性組成物を注入した後、加熱オーブン中へ入れ25~120℃まで徐々に昇温し22時間重合を行った。
得られた成形体は透明性良好であり、歪みのない外観良好なものであった。
評価結果を表-1に示す。
表-1に示した組成に変更した以外は実施例1と同様な操作を行った。組成および評価結果を表-1に示す。また、実施例2で得られた成形体については曲げ試験および穴開け引張試験を実施した。結果を表―2に示す。
ガラス製ビーカーに触媒のジメチル錫ジクロリド100ppm、Zelec-UN(商品名Stepan社製品;酸性リン酸エステル)1500ppm、m-キシレンジイソシアネートを44重量部、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とするポリチオール化合物Aを56重量部装入し、室温で攪拌し混合した。混合した化合物を減圧下、脱気操作をおこない、ガラスモールドとテープよりなるモールド中へ該重合性組成物を注入した後、加熱オーブン中へ入れ25~120℃まで徐々に昇温し20時間重合を行った。
得られた成形体は透明性良好であり、歪みのない外観良好なものであったが、アッベ数は30であった。評価結果を表-1に示す。
ガラス製ビーカーに触媒のジメチル錫ジクロリド100ppm、Zelec-UN(商品名、Stepan社製品;酸性リン酸エステル)1500ppm、m-キシレンジイソシアネートを51重量部、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とするポリチオール化合物Bを49重量部装入し、室温で攪拌し混合した。混合した化合物を減圧下、脱気操作をおこない、ガラスモールドとテープよりなるモールド中へ該重合性組成物を注入した後、加熱オーブン中へ入れ25~120℃まで徐々に昇温し20時間重合を行った。
得られた成形体は透明性良好であり、歪みのない外観良好なものであったが、アッベ数は31であった。評価結果を表-1に示す。
m-フェニレンジイソシアネートを43.5重量部、製造例1記載の方法にて合成したポリチオール化合物Aを56.5重量部、硬化触媒としてジブチル錫ジクロリド200ppm、内部離型剤(商品名:Zelec-UN(商品名、Stepan社製品)1200ppm、紫外線吸収剤(商品名:Viosorb-583、共同薬品株式会社製品)500ppmを混合して、60℃にて10分間加熱撹拌して均一なモノマー混合溶液とした(モノマー混合物中のメルカプト基とイソシアナト基のモル比は、SH/NCO=1.0)。このモノマー混合物を5分間減圧脱気した後、3μm PTFE製フィルターで濾過を行い、ガラスモールドとテープからなるモールド型へ注入し、50℃~120℃まで20時間かけて徐々に昇温して重合させた。重合終了後、ガラスモールドを離型させて樹脂成形体を得た。得られた成形体をさらに120℃で4時間アニール処理を行った。アッベ数は23であった。評価結果を表-1に示す。
ビス(2,3-エピチオプロピル)ジスルフィド90.9重量部、紫外線吸収剤(商品名:Tinuvin PS)1重量部を20℃にて混合溶解して均一溶液とした。この溶液にポリチオール化合物として4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とするポリチオール化合物B 9.1重量部を添加、混合溶解させた後、3μmPTFE製フィルターで濾過を行なった。続いて、この溶液にジシクロヘキシルメチルアミン910ppmおよびジメチルシクロヘキシルアミン190ppmを添加、混合溶解させた後、ガラスモールドとテープからなるモールド型へ注入し、30℃~80℃まで21時間かけて徐々に昇温して重合させた。重合終了後、ガラスモールド型を離型させて成形体を得た。得られた成形体をさらに120℃で3時間アニール処理を行った。穴開け引張り試験および三点曲げ試験のデータを表-2に示す。
化合物(a):m-キシレンジイソシアネート
化合物(b):m-フェニレンジイソシアネート
No.1-1:アリルイソシアネート
No.1-2:アリルイソチオシアネート
E-1: ビス(2,3-エピチオプロピル)ジスルフィド
A:1,1,3,3-テトラキス(メルカプトメチルチオ)プロパンを主成分とするポリチオール化合物
B:4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカンを主成分とするポリチオール化合物
C:4-メルカプトメチル-1,8ージメルカプト-3,6-ジチアオクタン
また、実施例9と比較例3を比較すると、屈折率は同程度ながら、実施例9方がよりアッベ数が高い成形体が得られた。さらに、実施例2と比較例4の結果から、本発明で得られる成形体は、引張り強度などの点でも優れた成形体であることが分かった。
以上より、分子内に、炭素-炭素二重結合と、イソシアナト基およびイソチオシアナト基から選択される1以上の基を有する化合物(A)と、ポリチオール化合物(B)とを含む光学材料用重合性組成物から、強度などにも優れ、高屈折率を有すると同時に高アッベ数でもあるバランスに優れたチオウレタン光学材料を得ることができた。
Claims (10)
- (A)分子内に、炭素-炭素二重結合と、イソシアナト基およびイソチオシアナト基から選択される1以上の基と、を有する化合物と、
(B)ポリチオール化合物と、
を含む、光学材料用重合性組成物。 - ポリチオール化合物(B)は、
ペンタエリスリトールテトラキス(3-メルカプトプロピオネート)、4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタンおよび3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタンよりなる群から選ばれる少なくとも1種である、請求項1乃至3のいずれかに記載の光学材料用重合性組成物。 - ポリチオール化合物(B)は、
4-メルカプトメチル-1,8-ジメルカプト-3,6-ジチアオクタン、5,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,7-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、4,8-ジメルカプトメチル-1,11-ジメルカプト-3,6,9-トリチアウンデカン、1,1,3,3-テトラキス(メルカプトメチルチオ)プロパン、4,6-ビス(メルカプトメチルチオ)-1,3-ジチアン、2-(2,2-ビス(メルカプトメチルチオ)エチル)-1,3-ジチエタン、1,1,2,2-テトラキス(メルカプトメチルチオ)エタンおよび3-メルカプトメチル-1,5-ジメルカプト-2,4-ジチアペンタンよりなる群から選ばれる少なくとも1種である、請求項1乃至3のいずれかに記載の光学材料用重合性組成物。 - 重合性組成物中の(全イソシアナト基数+全イソチオシアナト基数+2重結合数)/(全メルカプト基数)で表される官能基モル比が、0.5~2.0である、請求項1乃至5のいずれかに記載の光学材料用重合性組成物。
- 化合物(A)とポリチオール化合物(B)とを混合し、請求項1乃至6のいずれかに記載の光学材料用重合性組成物を調製する工程と、
前記重合性組成物を、注型用鋳型内に注入する工程と、
前記鋳型内で、前記重合性組成物を重合硬化する工程と、
を含む、光学材料の製造方法。 - 請求項7に記載の製造方法で得られた光学材料。
- e線の屈折率が1.6~1.8の範囲である請求項8に記載の光学材料。
- 請求項8または9に記載の光学材料からなる、プラスチック眼鏡レンズ。
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JP6275247B2 (ja) | 2018-02-07 |
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KR20160134767A (ko) | 2016-11-23 |
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CN106164124A (zh) | 2016-11-23 |
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