WO2016104744A1 - 内部離型剤、該内部離型剤を含む組成物および該組成物を用いたプラスチックレンズの製造方法 - Google Patents
内部離型剤、該内部離型剤を含む組成物および該組成物を用いたプラスチックレンズの製造方法 Download PDFInfo
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- WO2016104744A1 WO2016104744A1 PCT/JP2015/086334 JP2015086334W WO2016104744A1 WO 2016104744 A1 WO2016104744 A1 WO 2016104744A1 JP 2015086334 W JP2015086334 W JP 2015086334W WO 2016104744 A1 WO2016104744 A1 WO 2016104744A1
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Images
Classifications
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
- C07F9/00—Compounds containing elements of Groups 5 or 15 of the Periodic Table
- C07F9/02—Phosphorus compounds
- C07F9/06—Phosphorus compounds without P—C bonds
- C07F9/08—Esters of oxyacids of phosphorus
- C07F9/09—Esters of phosphoric acids
- C07F9/091—Esters of phosphoric acids with hydroxyalkyl compounds with further substituents on alkyl
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C33/00—Moulds or cores; Details thereof or accessories therefor
- B29C33/56—Coatings, e.g. enameled or galvanised; Releasing, lubricating or separating agents
- B29C33/60—Releasing, lubricating or separating agents
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- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29C—SHAPING OR JOINING OF PLASTICS; SHAPING OF MATERIAL IN A PLASTIC STATE, NOT OTHERWISE PROVIDED FOR; AFTER-TREATMENT OF THE SHAPED PRODUCTS, e.g. REPAIRING
- B29C39/00—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor
- B29C39/02—Shaping by casting, i.e. introducing the moulding material into a mould or between confining surfaces without significant moulding pressure; Apparatus therefor for making articles of definite length, i.e. discrete articles
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F2/00—Processes of polymerisation
- C08F2/44—Polymerisation in the presence of compounding ingredients, e.g. plasticisers, dyestuffs, fillers
-
- 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
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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
-
- 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
- C08K5/49—Phosphorus-containing compounds
- C08K5/51—Phosphorus bound to oxygen
- C08K5/52—Phosphorus bound to oxygen only
- C08K5/521—Esters of phosphoric acids, e.g. of H3PO4
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L101/00—Compositions of unspecified macromolecular compounds
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- 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
-
- 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
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- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B3/00—Simple or compound lenses
-
- B—PERFORMING OPERATIONS; TRANSPORTING
- B29—WORKING OF PLASTICS; WORKING OF SUBSTANCES IN A PLASTIC STATE IN GENERAL
- B29L—INDEXING SCHEME ASSOCIATED WITH SUBCLASS B29C, RELATING TO PARTICULAR ARTICLES
- B29L2011/00—Optical elements, e.g. lenses, prisms
-
- 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
- C08G2125/00—Compositions for processes using internal mould release agents
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2666/00—Composition of polymers characterized by a further compound in the blend, being organic macromolecular compounds, natural resins, waxes or and bituminous materials, non-macromolecular organic substances, inorganic substances or characterized by their function in the composition
- C08L2666/28—Non-macromolecular organic substances
- C08L2666/40—Phosphorus-containing compounds
Definitions
- the present invention relates to an internal mold release agent used as an additive in cast polymerization, a composition containing the internal mold release agent, and a method for producing a plastic lens using the composition.
- plastic lenses are polymerized and cured by injecting a composition containing a polymerization reactive compound into a cavity formed by a glass mold and a tape or a resin gasket, and then heating or radiating radiation.
- a composition containing a polymerization reactive compound into a cavity formed by a glass mold and a tape or a resin gasket, and then heating or radiating radiation.
- Manufactured by a mold polymerization method since the cured resin is not easily released by adhering to a glass mold, in consideration of productivity, an internal release agent is added in advance to a composition containing a polymerization reactive compound to be injected, Many proposals regarding the internal mold release agent have been made.
- Patent Document 1 a method using an alkoxy polyethylene glycol phosphate as an internal mold release agent
- Patent Document 2 a method using an alkoxy polyethylene glycol phosphate as an internal mold release agent
- Patent Document 3 a method using an alkoxy polyethylene glycol phosphate as an internal mold release agent
- Patent Document 4 a method using an alkoxy polyethylene glycol phosphate as an internal mold release agent
- Patent Document 5 a method using an alkoxy polyethylene glycol phosphate as an internal mold release agent.
- Patent Document 6 an alkoxy polypropylene glycol phosphate ester as an internal mold release agent
- Patent Document 9 a method using a sulfur-containing phosphate ester
- Patent Document 12 a method using a metal catalyst other than tin such as zinc and an alkoxy polyethylene glycol phosphate ester or alkoxy polypropylene glycol phosphate ester
- Patent Document 13 the proposal about the manufacturing method of phosphate ester which is surfactant is also performed (patent document 13).
- the present invention provides an internal mold release agent that is more excellent in mold release and transparency than conventional internal mold release agents, a composition containing the internal mold release agent, and a method for producing a plastic lens using the composition.
- the task is to do.
- a phosphoric diester compound (hereinafter referred to as phosphorus) having a poly (oxyalkylene) alkyl ether group and an alkyl group represented by the following general formula (1):
- the acid diester compound A "was used as an internal mold release agent, it was found that the molded product obtained even when added in a large amount was suppressed in cloudiness and maintained high transparency. That is, by using the phosphoric acid diester compound A represented by the general formula (1), the molded product is released from the mold as compared with the phosphoric acid monoester compound and the phosphoric acid diester compound that have been used conventionally. As a result, the present invention has been found to be excellent in transparency and also in the transparency of the resulting molded article.
- R 1 and R 2 independently represent a hydrocarbon group having 1 to 30 carbon atoms which may be substituted with at least one hydroxyl group, and R 3 represents an alkylene group having 2 to 4 carbon atoms
- a plurality of R 3 may be the same or different
- M represents a hydrogen atom, an ammonium ion, an alkali metal ion, or a half-valent alkaline earth metal ion
- n represents an integer of 1 to 60. .
- the polymerization reactive compound is a polyiso (thio) cyanate compound, a poly (thio) epoxy compound, a polyoxetanyl compound, a polythietanyl compound, a poly (meth) acryloyl compound, a polyalkene compound, an alkyne compound, or a poly (thi) ol compound.
- [5] A molded product obtained by polymerizing the composition according to any one of [2] to [4].
- An optical material comprising the molded article according to [5].
- [7] A plastic lens comprising the molded article according to [5].
- [8] A method for producing a plastic lens, comprising a step of cast polymerization of the composition according to any one of [2] to [4].
- the molded product obtained by releasing from the mold has high transparency, and can be suitably used as a plastic lens such as a spectacle lens, a camera lens, and a pickup lens.
- FIG. 2 is a 1 H-NMR spectrum chart of a phosphate ester (110A) containing a phosphate diester (110) obtained in Preparation Example 1.
- FIG. 3 is an IR spectrum chart of a phosphoric ester (110A) containing the phosphoric diester (110) obtained in Preparation Example 1.
- 3 is a 1 H-NMR spectrum chart of phosphoric acid diester (100) obtained in Preparation Example 2.
- 3 is an electrospray mass spectrometry chart of phosphoric acid diester (100) obtained in Preparation Example 2.
- 4 is an IR spectrum chart of phosphoric acid diester (100) obtained in Preparation Example 2.
- the internal mold release agent according to the present invention a composition containing the internal mold release agent, and a method for producing a plastic lens using the composition will be described.
- the internal mold release agent of the present invention contains at least one phosphodiester compound A represented by the following general formula (1).
- the groups (R 1 , R 2 , R 3 , M) of the following general formula (1) may be the same or different for each phosphoric acid diester compound A.
- the phosphoric diester compound A may be a mixture of structural isomers.
- R 1 and R 2 independently represent a hydrocarbon group having 1 to 30 carbon atoms which may be substituted with at least one hydroxyl group.
- the hydrocarbon group having 1 to 30 carbon atoms include an alkyl group having 1 to 30 carbon atoms, an aryl group having 6 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, Examples thereof include an alkylarylalkyl group having 8 to 30 carbon atoms.
- alkyl group having 1 to 30 carbon atoms examples include, for example, an alkyl group having 1 to 3 carbon atoms such as methyl group, ethyl group, 1-propyl group, isopropyl group, 1-butyl group, 2-butyl group, isobutyl group, tert.
- aryl group having 6 to 30 carbon atoms examples include phenyl group, naphthyl group, anthracenyl group, phenanthrenyl group, benzoanthracenyl group, benzophenanthrenyl group, naphthacenyl group, pyrenyl group, dibenzoanthracenyl group, pentacenyl group , Picenyl group, benzopyrenyl group, and the like.
- alkylaryl group having 7 to 30 carbon atoms examples include tolyl group (methylphenyl group), dimethylphenyl group, trimethylphenyl group, ethylphenyl group, propylphenyl group, butylphenyl group, pentylphenyl group, cyclohexylphenyl group, and trimethylphenyl group.
- tolyl group methylphenyl group
- dimethylphenyl group trimethylphenyl group
- ethylphenyl group propylphenyl group
- butylphenyl group pentylphenyl group
- cyclohexylphenyl group examples include tolyl group (methylphenyl group), dimethylphenyl group, trimethylphenyl group, ethylphenyl group, propylphenyl group, butylphenyl group, pentylphenyl group, cyclohexylphenyl group, and trimethylphenyl group.
- Examples of the arylalkyl group having 7 to 30 carbon atoms include benzyl group, phenethyl group, 1-phenylpropyl group, naphthylmethyl group, naphthylethyl group and the like.
- Examples of the alkylarylalkyl group having 8 to 30 carbon atoms include methylbenzyl group, dimethylbenzyl group, trimethylbenzyl group, butylbenzyl group and dibutylbenzyl group.
- the hydrogen atom in these hydrocarbon groups may be substituted with one or more hydroxyl groups.
- R 1 and R 2 are not limited to these exemplified functional groups.
- the mold release agent of the present invention tends to improve releasability when the number of carbon atoms of the hydrocarbon group increases, while it tends to decrease solubility and dispersibility when it increases excessively.
- hydrocarbon groups having 1 to 30 carbon atoms hydrocarbon groups having 4 to 30 carbon atoms are relatively preferable, and hydrocarbon groups having 7 to 30 carbon atoms are more preferable.
- the hydrocarbon groups having 1 to 30 carbon atoms the most preferable form is an alkyl group having 7 to 30 carbon atoms, an alkylaryl group having 7 to 30 carbon atoms, an arylalkyl group having 7 to 30 carbon atoms, and carbon. Examples thereof include an alkylarylalkyl group of several 8 to 30.
- R 3 represents an alkylene group having 2 to 4 carbon atoms.
- R 3 when a plurality of R 3 are present, they may be the same or different.
- Specific examples of R 3 include, for example, 1,2-ethylene group, 1,2-propylene group, 1,2-butylene group, 1,3-propylene group, 1,3-butylene group, 1,4-butylene. Groups and the like. Among these, preferred forms include 1,2-ethylene groups or 1,2-propylene groups, and most preferred are 1,2-ethylene groups.
- M represents a hydrogen atom, an ammonium ion, an alkali metal ion, and a half-valent alkaline earth metal ion.
- the ammonium ion represents an ammonium ion, a primary ammonium ion, a secondary ammonium ion, a tertiary ammonium ion, and a quaternary ammonium ion, and may contain a functional group other than an ammonium group.
- Preferred ammonium ions include, for example, ammonium ion, methyl ammonium ion, dimethyl ammonium ion, trimethyl ammonium ion, tetramethyl ammonium ion, ethyl ammonium ion, diethyl ammonium ion, triethyl ammonium ion, 1-propyl ammonium ion, isopropyl ammonium ion, Tris (1-butyl) ammonium ion, 2-hydroxypropylammonium ion, bis (2-hydroxyethyl) ammonium ion, tris (2-hydroxyethyl) ammonium ion, half-valent bis ⁇ N-octyloxy-N- Hydro-2,2,6,6-tetramethyl-4-piperazinyl ⁇ decanedionic acid ammonium ion and the like
- a hydrogen atom, an alkali metal ion, and a quaternary ammonium ion are preferable, and an alkali metal ion and a hydrogen atom are more preferable.
- preferable alkali metal ions include lithium ions, sodium ions, potassium ions, rubidium ions, and the like.
- n represents an integer of 1 to 60, preferably in the range of 1 to 40, and more preferably in the range of 1 to 30.
- a novel compound represented by the following general formula (2) can be preferably used.
- x represents an integer of 1 to 23
- n represents an integer of 4 to 13
- m is 12 or 13.
- Q 1 and Q 2 represent either a hydrogen atom or a methyl group, and a plurality of Q 1 or Q 2 may be the same or different. However, the case where both Q 1 and Q 2 are methyl groups in the repeating unit in parentheses is excluded.
- a compound represented by the following general formula (3) or (4) can be preferably used. These compounds can be used as a mixture of structural isomers.
- x represents an integer of 1 to 23.
- Q 1 and Q 2 represent either a hydrogen atom or a methyl group, and a plurality of Q 1 or Q 2 may be the same or different. However, the case where both Q 1 and Q 2 are methyl groups in the repeating unit in parentheses is excluded.
- Q 1 and Q 2 represent either a hydrogen atom or a methyl group, and a plurality of Q 1 or Q 2 may be the same or different. However, in the repeating unit in parentheses, the case where Q 1 and Q 2 are both hydrogen atoms and the case where both are methyl groups are excluded.
- the compound represented by the general formula (1) of the present invention is synthesized by a known production method.
- a typical compound represented by the following general formula (h) selected from the compounds represented by the general formula (1) is taken as an example, and the main production route is shown in the following reaction formula. .
- tertiary amines such as triethylamine and pyridine may be added.
- the amount of tertiary amine added is 0.1 to 4.0 equivalents, preferably 1.8 to 2.2 equivalents, relative to phosphorus oxyhalide.
- the phosphorus oxyhalide include phosphorus oxychloride and phosphorus oxybromide, among which phosphorus oxychloride is preferable.
- the alcohol (d) is added to the phosphorus oxyhalide in an amount of 0.1 to 2 equivalents, preferably 0.8 to 1.2 equivalents, and -60 ° C to 100 ° C, preferably -40 to 50 ° C. React for 1-36 hours.
- the reaction mixture containing phosphoric acid diester monohalide (e) is obtained.
- the reaction temperature is 0 ° C to 100 ° C, preferably 10 ° C to 50 ° C.
- the liquid property of the solution is preferably pH 8 or less, and more preferably pH 7 or less.
- a solvent may be added according to the properties of the raw materials, intermediates, and final target product.
- acetate compounds such as butyl acetate, ketone compounds such as acetone, ether compounds such as diethyl ether and tetrahydrofuran, nitrile compounds such as acetonitrile, aprotic polar compounds such as N, N-dimethylformamide, chloroform and chlorobenzene, etc.
- halogen compounds hydrocarbon compounds such as hexane and toluene.
- Step (A) Water is added to the compound (c) obtained in the step (A), and hydrolysis is performed in the same manner as in the step (C) to obtain a phosphoric acid monoester (f).
- a method of neutralizing one of the two hydroxyl groups bonded to the phosphorus atom with a base is preferably used.
- the base used is not specifically limited, Alkali metals, such as sodium hydroxide, sodium carbonate, sodium hydrogencarbonate, potassium hydroxide, are used preferably.
- the reaction solvent used in the reaction of step (A) to step (E) is appropriately selected depending on the raw materials, intermediates, properties of the final target product, and the like.
- water alcohol compounds such as methanol, acetate compounds such as butyl acetate, ketone compounds such as acetone, ether compounds such as THF (tetrahydrofuran), nitrile compounds such as acetonitrile, aprotic such as N, N-dimethylformamide
- examples thereof include polar compounds, halogen compounds such as chloroform and chlorobenzene, and hydrocarbon compounds such as hexane and toluene.
- the present invention is characterized in that one or a mixture of two or more selected from the phosphoric acid diester compound A represented by the general formula (1) is used as an internal mold release agent.
- the specific effect produced by the structure represented by the general formula (1) will be described by taking a typical compound as an example.
- the phosphoric diester compound A of an alkoxypolyalkylene glycol and an alkyl alcohol which is a phosphoric diester compound of the present invention is a phosphoric diester compound of an alkyl alcohol (a structure in which two identical alkyl ether groups are bonded to a P atom).
- the phosphoric acid diester compound A tends to hardly form micelles and has good dispersibility, and therefore exhibits high transparency and excellent releasability.
- the phosphoric diester compound of alkoxy polyalkylene glycol (a structure in which two identical poly (oxyalkylene) alkyl ether groups are bonded to the P atom) and the phosphoric monoester compound of alkoxy alkylene glycol
- the phosphoric acid diester compound A exhibits more excellent releasability while maintaining high transparency. That is, the phosphoric acid diester compound A of the present invention is more useful as an internal mold release agent because it is more excellent in releasability and transparency than the conventional phosphoric acid diester compound or phosphoric acid monoester compound. It is.
- the internal mold release agent of the present invention may contain a compound other than the phosphodiester compound A represented by the general formula (1) within a range in which the effect of the present invention is obtained.
- compounds other than the compound of the general formula (1) include a phosphoric acid diester compound B which is a by-product, a phosphoric acid monoester compound C derived from an intermediate, and an alcohol D represented by the following general formula.
- R 1, R 2, R 3, M, n is as in formula (1) synonymous.
- phosphoric acid derived from a raw material, a reaction solvent, and the like can be included.
- the phosphoric diester compound A represented by the general formula (1) is in the range of 0.1 to 100% by weight, preferably in the range of 1 to 100% by weight, in the internal mold release agent (100% by weight) of the present invention. More preferably, it is in the range of 5 to 100% by weight. It is preferable for the purity of the phosphoric acid diester compound A represented by the general formula (1) to be in the above range because of excellent mold releasability.
- the allowable content of the compounds B to D is 100% by weight in total of the compounds A to D. 0.1 to 99.9% by weight, preferably 1 to 99% by weight, and more preferably 5 to 95% by weight.
- the content of compounds B to D other than compound A of general formula (1) is preferably in the above range because of excellent release properties.
- the internal mold release agent of the present invention can contain compounds B to D in addition to the phosphoric diester compound A represented by the general formula (1).
- Phosphoric acid diester compound A is 0.1 to 99.9% by weight, preferably 1 to 99% by weight, more preferably 5 to 95% by weight, particularly preferably 5 to 80% by weight
- the phosphoric acid diester compound B is 0 to 99.8% by weight, preferably 0 to 98% by weight, more preferably 0 to 90% by weight, particularly preferably 5 to 80% by weight, 0.05 to 99.85% by weight of phosphoric monoester compound C, preferably 0.5 to 98.5% by weight, more preferably 2.5 to 92.5% by weight, particularly preferably 5 to 80% by weight
- Alcohol D is 0.05 to 99.85% by weight, preferably 0.5 to 98.5% by weight, more preferably 2.5 to 92.5% by weight, particularly preferably 10 to 85% by weight, Can be included in amounts.
- the internal mold release agent containing the phosphoric acid diester of this invention can also be mixed and used with another internal mold release agent.
- composition of this invention contains a polymerization reactive compound and the above-mentioned internal mold release agent.
- the addition amount of the phosphoric acid diester compound A of the general formula (1) contained in the internal mold release agent of the present invention varies depending on various compounds including the polymerization reactive compound, the shape of the mold, etc. Thus, it is in the range of 1 ⁇ 10 ⁇ 1 ppm to 5 ⁇ 10 4 ppm, preferably in the range of 1 ppm to 2 ⁇ 10 4 ppm, and more preferably in the range of 5 ppm to 1 ⁇ 10 4 ppm.
- the phosphoric acid diester compound of the general formula (1) within the range, it is possible to obtain a molded article having excellent releasability and excellent transparency.
- the polymerization-reactive compound contained in the composition of the present invention contains self-polymerization, copolymerization, or addition polymerization in the presence or absence of additives such as an initiator and a catalyst that are added as necessary.
- additives such as an initiator and a catalyst that are added as necessary.
- Polymerizable compounds having at least one polymerizable functional group that can be produced are included.
- the compound having a polymerizable functional group capable of self-polymerization, copolymerization, or addition polymerization will be described more specifically.
- Polythietanyl compound having, poly (meth) acryloyl compound having at least two selected from methacryloyloxy group, acryloyloxy group, methacryloylthio group, acryloylthio group, methacrylamide group, or acrylamide group, methacrylo Polyalkene compound having two or more
- Polyiso (thio) cyanate compounds include tetramethylene diisocyanate, pentamethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, octamethylene diisocyanate, 2,2,4-trimethylhexamethylene diisocyanate, 2,4,4-trimethylhexamethylene diisocyanate.
- Aliphatic polyisocyanate compounds such as lysine diisocyanatomethyl ester, lysine triisocyanate, xylylene diisocyanate; Isophorone diisocyanate, bis (isocyanatomethyl) cyclohexane, dicyclohexylmethane diisocyanate, dicyclohexyldimethylmethane isocyanate, 2,5-bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane, 2,6-bis (isocyanato) Methyl) bicyclo- [2.2.1] -heptane, 3,8-bis (isocyanatomethyl) tricyclodecane, 3,9-bis (isocyanatomethyl) tricyclodecane, 4,8-bis (isocyanato) Alicyclic polyisocyanate compounds such as methyl) tricyclodecane and 4,9-bis (isocyanatomethyl) tricyclodecane
- poly (thio) epoxy compound examples include polyepoxy compounds such as bisphenol A diglycidyl ether; Bis (2,3-epoxypropyl) sulfide, bis (2,3-epoxypropyl) disulfide, bis (2,3-epoxypropylthio) methane, 1,2-bis (2,3-epoxypropylthio) ethane, 1,2-bis (2,3-epoxypropylthio) propane, 1,3-bis (2,3-epoxypropylthio) propane, 1,3-bis (2,3-epoxypropylthio) -2-methyl Propane, 1,4-bis (2,3-epoxypropylthio) butane, 1,4-bis (2,3-epoxypropylthio) -2-methylbutane, 1,3-bis (2,3-epoxypropylthio) ) Butane, 1,5-bis (2,3-epoxypropylthio) pentane,
- polyoxetanyl compound examples include 3-ethyl-3-hydroxymethyloxetane, 1,4-bis ⁇ [(3-ethyl-3-oxetanyl) methoxy] methyl ⁇ benzene, 3-ethyl-3- (phenoxymethyl) oxetane, Examples include di [1-ethyl- (3-oxetanyl)] methyl ether, 3-ethyl-3- (2-ethylhexyloxymethyl) oxetane, phenol novolac oxetane, and the like.
- polythietanyl compound examples include 1- ⁇ 4- (6-mercaptomethylthio) -1,3-dithianylthio ⁇ -3- ⁇ 2- (1,3-dithietanyl) ⁇ methyl-7,9-bis (mercaptomethylthio) -2 , 4,6,10-tetrathiaundecane, 1,5-bis ⁇ 4- (6-mercaptomethylthio) -1,3-dithianylthio ⁇ -3- ⁇ 2- (1,3-dithietanyl) ⁇ methyl-2, 4-dithiapentane, 4,6-bis [3- ⁇ 2- (1,3-dithietanyl) ⁇ methyl-5-mercapto-2,4-dithiapentylthio] -1,3-dithiane, 3- ⁇ 2- (1,3-dithietanyl) ⁇ methyl-7,9-bis (mercaptomethylthio) -1,11-dimercapto-2,4,6,10-
- Poly (meth) acryloyl compounds include ethylene glycol diacrylate, 1,3-butylene glycol diacrylate, 1,4-butanediol diacrylate, 1,6-hexanediol diacrylate, cyclohexanedimethanol diacrylate, alkoxylated hexane Diol diacrylate, neopentyl glycol diacrylate, caprolactone modified neopentyl glycol hydroxypivalate diacrylate, cyclohexane dimethanol diacrylate, diethylene glycol diacrylate, dipropylene glycol diacrylate, bisphenol A diacrylate, ethoxylated bisphenol A diacrylate, hydroxy Pivalaraldehyde modified trimethylolpropane diacrylate, neopentyl Recall diacrylate, polyethylene glycol diacrylate, propoxylated neopentyl glycol diacrylate, tetraethylene glycol diacrylate, tricyclode
- polyalkene compound examples include polyethylene, polypropylene, polyisobutylene, diethylene glycol bis (allyl carbonate), divinylbenzene, and the like.
- alkyne compounds examples include 2-butyne, 2-pentyne, 2-hexyne, 3-hexyne, 2-heptin, 3-heptin, 2-octyne, 3-octyne, 4-octyne, diisopropylacetylene, 2-nonine, 3- Nonine, 4-nonine, 5-nonine, 2-decyne, 3-decyne, 4-decyne, 5-decyne, di-tert-butylacetylene, diphenylacetylene, dibenzylacetylene, methyl-iso-propylacetylene, methyl-tert -Butylacetylene, ethyl-iso-propylacetylene, ethyl-tert-butylacetylene, n-propyl-iso-propylacetylene, n-propyl-tert-butylacetylene, phenylmethylacety
- examples of polyol compounds include ethylene glycol, diethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butylene glycol, and neopentyl glycol.
- Glycerin trimethylolethane, trimethylolpropane, ditrimethylolpropane, butanetriol, 1,2-methylglucoside, pentaerythritol, dipentaerythritol, tripentaerythritol, sorbitol, erythritol, threitol, ribitol, arabinitol, xylitol, allitol , Manitol, Dorsitol, Iditol, Glycol, Inositol, Hexanetriol, Trig Cellose, diglycerol, triethylene glycol, polyethylene glycol, tris (2-hydroxyethyl) isocyanurate, cyclobutanediol, cyclopentanediol, cyclohexanediol, cycloheptanediol, cyclooctanediol, cyclohexanedimethanol
- polyol compounds include oxalic acid, glutamic acid, adipic acid, acetic acid, propionic acid, cyclohexanecarboxylic acid, ⁇ -oxocyclohexanepropionic acid, dimer acid, phthalic acid, isophthalic acid, salicylic acid, 3-bromopropionic acid, 2
- a condensation reaction product of an organic acid such as bromoglycol, dicarboxycyclohexane, pyromellitic acid, butanetetracarboxylic acid, bromophthalic acid and the above polyol
- An addition reaction product of the above polyol with an alkylene oxide such as ethylene oxide or propylene oxide
- An addition reaction product of an alkylene polyamine and an alkylene oxide such as ethylene oxide or propylene oxide
- Polythiol compounds include methanedithiol, 1,2-ethanedithiol, 1,2,3-propanetrithiol, 1,2-cyclohexanedithiol, bis (2-mercaptoethyl) ether, tetrakis (mercaptomethyl) methane, diethylene glycol bis (2-mercaptoacetate), diethylene glycol bis (3-mercaptopropionate), ethylene glycol bis (2-mercaptoacetate), ethylene glycol bis (3-mercaptopropionate), trimethylolpropane tris (2-mercaptoacetate) , Trimethylolpropane tris (3-mercaptopropionate), trimethylolethanetris (2-mercaptoacetate), trimethylolethanetris (3-mercaptopropionate) ), Pentaerythritol tetrakis (2-mercaptoacetate), pentaerythritol tetrakis (3-mercaptopropionate), bis (
- Polyamine compounds include ethylenediamine, 1,2-, or 1,3-diaminopropane, 1,2-, 1,3-, or 1,4-diaminobutane, 1,5-diaminopentane, 1,6-diamino Hexane, 1,7-diaminoheptane, 1,8-diaminooctane, 1,10-diaminodecane, 1,2-, 1,3- or 1,4-diaminocyclohexane, o-, m- or p-diamino Benzene, 3,4- or 4,4'-diaminobenzophenone, 3,4- or 4,4'-diaminodiphenyl ether, 4,4'-diaminodiphenylmethane, 4,4'-diaminodiphenyl sulfide, 3,3'- Or 4,4'-diaminodiphenylsulfone, 2,7-di
- acid anhydride examples include succinic anhydride, phthalic anhydride, maleic anhydride, tetrabromophthalic anhydride, tetrahydrophthalic anhydride, trimellitic anhydride, dodecyl succinic anhydride, and the like.
- Polycarboxylic acid compounds include succinic acid, adipic acid, sebacic acid, azelaic acid, dodecanedioic acid, terephthalic acid, isophthalic acid, orthophthalic acid, phthalic anhydride, tetrahydrophthalic acid, hexahydrophthalic acid, naphthalenedicarboxylic acid, biphenyl Examples thereof include dicarboxylic acid, dimer acid, trimellitic acid, pyromellitic acid, and ⁇ -caprolactone.
- the polymerization reactive compounds may be used alone or in combination of two or more.
- the polymerization reactive compound contained in the composition of the present invention will be described in more detail.
- the above-mentioned polymerization reactive compounds can be classified into (Group A) and (Group B) depending on the reactivity.
- Group B Poly (thi) ol compounds, polyamine compounds, acid anhydrides, or polycarboxylic acid compounds can be classified as (group B) as addition polymerizable compounds. However, the above (Group A) is not included in (Group B).
- any one selected from (Group A) or (Group B) is selected.
- one kind selected from self-polymerization or copolymerization is one kind selected from addition polymerizability (group B). It is preferable because it hardens more easily.
- Polyiso (thio) cyanate compounds classified as self-polymerizable or copolymerizable compounds are more self-polymerizable than other compounds classified as (Group A), or copolymerization reactions with (Group A) compounds.
- a self-polymerization reaction type polymer such as a 1-nylon type polymer and an isocyanurate type polymer may be obtained.
- an ethylene carbonate type copolymer may be obtained in the copolymerization with a poly (thio) epoxy compound.
- the compounding ratio of the acid anhydride to the poly (thiol) or polyamine is approximately 8/2 in terms of the molar ratio of the acid anhydride group of the acid anhydride / the mercapto group of the poly (thiol) (or the amino group of the polyamine).
- the range is from ⁇ 2 / 8, preferably from 6/4 to 4/6, and more preferably from 55/45 to 45/55.
- the blending ratio in the case of using both (Group A) and (Group B) is approximately 999/1 when expressed in terms of the functional group molar ratio of (Group A) polymerizable functional group / (Group B) polymerizable functional group.
- the range is from 1/9, preferably from 99/1 to 10/90, more preferably from 9/1 to 3/7, and most preferably from 7/3 to 4/6.
- composition of the present invention may contain components other than the polymerization reactive compound.
- the composition containing the polymerization reactive compound contains as little solvent and water as possible. Accordingly, the amount of the solvent and water contained in the composition of the present invention immediately before being injected into the cavity is preferably at least 20% by weight, more preferably 5% by weight or less, and even more preferably 1% by weight or less.
- Examples of the solvent that is highly likely to be contained in the composition of the present invention include, for example, the reaction solvent and polymerizable compound remaining in the phosphoric diester compound A for internal release agent represented by the general formula (1) of the present invention.
- the solvent mixed in by various routes such as the reaction solvent remaining in the solvent, the solvent added for the purpose of lowering the viscosity of the composition, or the solvent added for dissolving various additives for the purpose of improving the operability.
- Solvents that are likely to remain include, for example, water such as water, methanol, ethanol, 1-propanol, isopropanol, 1-butanol, isobutanol, t-butanol, 1-pentanol, 2-pentanol, Alcohols such as 3-pentanol, isopentanol, 1-hexanol, 2-ethylhexanol, 1-octanol, 2-methoxyethanol, 1-methoxy-2-propanol, acetone, methyl ethyl ketone, methyl-n-propyl ketone, Ketones such as methyl isopropyl ketone, methyl-n-butyl ketone, methyl isobutyl ketone, cyclohexanone, esters such as ethyl acetate, acetic acid-n-propyl, isopropyl acetate, acetic acid-n-butyl, iso
- Aliphatic hydrocarbons aromatic hydrocarbons such as benzene, toluene, xylene, nitrogen-containing compounds such as N, N-dimethylformamide, N, N-dimethylacetamide, n-methylpyrrolidone, nitrobenzene, dichloromethane, chloroform, And halogen-containing compounds such as dichloroethane, 1,1,2-trichloro-1,1,2-trifluoroethane, 1,1,2,2-tetrachloro-1,2-difluoroethane, and the like.
- a polymerization catalyst or a thermal polymerization initiator is added, and other than infrared rays (heat) such as ultraviolet rays.
- a photopolymerization initiator is added in the case of curing by the radiation.
- polymerization catalyst examples include a tertiary amine compound and an inorganic acid salt or organic acid salt thereof, a metal compound, a quaternary ammonium salt, or an organic sulfonic acid.
- the amount of the polymerization catalyst used is preferably in the range of 5 ppm to 15% by weight, more preferably in the range of 10 ppm to 10% by weight, and still more preferably in the range of 50 ppm to 3% by weight with respect to the composition.
- thermal polymerization initiator examples include ketone peroxide compounds such as methyl isobutyl ketone peroxide and cyclohexanone peroxide; Diacyl peroxide compounds such as isobutyryl peroxide, o-chlorobenzoyl peroxide, benzoyl peroxide; Dialkyl peroxide compounds such as tris (t-butylperoxy) triazine, t-nutylcumyl peroxide; 1,1-di (t-hexylperoxy) cyclohexane, 2,2-bis (4,4-di-t-butylperoxycyclohexyl) propane, 2,2-di (t-butylperoxy) butane, etc.
- ketone peroxide compounds such as methyl isobutyl ketone peroxide and cyclohexanone peroxide
- Diacyl peroxide compounds such as isobutyryl peroxide, o-chlorobenzoyl
- Peroxyketal compounds ⁇ -cumylperoxyneodecanoate, t-butylperoxypivalate, 2,4,4-trimethylpentylperoxy-2-ethylhexanoate, t-butylperoxy-2-ethylhexanoate, alkyl perester compounds such as t-butylperoxy-3,5,5-trimethylhexanoate; Peroxycarbonate compounds such as di-3-methoxybutylperoxydicarbonate, bis (4-t-butylcyclohexyl) peroxydicarbonate, t-butylperoxyisopropylcarbonate, diethylene glycol bis (t-butylperoxycarbonate), etc. Is mentioned.
- Examples of the photopolymerization initiator used include a photoradical polymerization initiator, a photocationic polymerization initiator, and a photoanionic polymerization initiator. Among these photopolymerization initiators, a photoradical polymerization initiator is preferable.
- photo radical polymerization initiator examples include Irgacure 127 (manufactured by BASF), Irgacure 651 (manufactured by BASF), Irgacure 184 (manufactured by BASF), Darocur 1173 (manufactured by BASF), benzophenone, 4- Phenylbenzophenone, Irgacure 500 (made by BASF), Irgacure 2959 (made by BASF), Irgacure 907 (made by BASF), Irgacure 369 (made by BASF), Irgacure 1300 (made by BASF), Irgacure 819 (BASF), Irgacure 1800 (BASF), Darocur TPO (BASF), Darocur 4265 (BASF), Irgacure OXE01 (BASF), Irgacure OXE02 (BASF) Escaure KT55 (Lamberti), Escaure ONE (Lamberti
- Irgacure 127 (manufactured by BASF), Irgacure 184 (manufactured by BASF), Darocur 1173 (manufactured by BASF), Irgacure 500 (manufactured by BASF), Irgacure 819 (BASF) Darocur TPO (manufactured by BASF), Esacure ONE (manufactured by Lamberti), Esacure KIP100F (manufactured by Lamberti), Esacure KT37 (manufactured by Lamberti) and Esacure KTO46 (manufactured by Lamberti) are preferable.
- photocationic polymerization initiator examples include Irgacure 250 (manufactured by BASF), Irgacure 784 (manufactured by BASF), Esacure 1064 (manufactured by Lamberti), CYRAURE UVI 6990 (manufactured by Union Carbide Japan), Adeka Optomer SP-172 (made by ADEKA), Adeka optomer SP-170 (made by ADEKA), Adeka optomer SP-152 (made by ADEKA), Adeka optomer SP-150 (made by ADEKA), etc. are mentioned. .
- a photopolymerization accelerator When using the photopolymerization initiator, a photopolymerization accelerator may be used in combination.
- the photopolymerization accelerator include 2,2-bis (2-chlorophenyl) -4,5′-tetraphenyl-2′H- ⁇ 1,2 ′> biimidazolol, tris (4-dimethylaminophenyl) methane, Examples include 4,4′-bis (dimethylamino) benzophenone, 2-ethylanthraquinone, camphorquinone, and the like.
- the amount of the photopolymerization initiator and thermal polymerization initiator used in the composition is preferably in the range of 0.1 to 20% by weight, more preferably in the range of 0.5 to 10% by weight, still more preferably 1 to It is in the range of 5% by weight.
- an ultraviolet absorber and a hindered amine light stabilizer are further added to the composition of the present invention to improve weather resistance.
- the composition is given.
- the ultraviolet absorber is not particularly limited.
- a benzotriazole ultraviolet absorber a triazine ultraviolet absorber, a benzophenone ultraviolet absorber, a benzoate ultraviolet absorber, a propanedioic acid ester ultraviolet absorber, or an oxanilide type.
- Various ultraviolet absorbers such as an ultraviolet absorber can be used.
- HALS hindered amine light stabilizer
- HALS Hindered Amine Light Stabilizers
- the molecular weight is roughly divided into low molecular weight HALS, medium molecular weight HALS, high molecular weight HALS, and reactive HALS.
- hindered amine light stabilizer for example, trade name Tinuvin 111FDL (manufactured by BASF), bis (1-octyloxy-2,2,6,6-tetramethyl-4-piperidyl) sebacate (trade name) Tinuvin 123 (manufactured by BASF), trade name Tinuvin 144 (manufactured by BASF), trade name Tinuvin 292 (manufactured by BASF), trade name Tinuvin 765 (manufactured by BASF), trade name Tinuvin 770 (manufactured by BASF), N , N′-bis (3-aminopropyl) ethylenediamine-2,4-bis [N-butyl-N- (1,2,2,6,6-pentamethyl-4-piperidyl) amino] -6-chloro-1 , 3,5-triazine condensate (trade name CHIMASSORB119FL (manufactured by BASF)), trade name CHIMASSORB2020
- the addition amount of the ultraviolet absorber and the hindered amine light stabilizer is not particularly limited, but the ultraviolet absorber in the composition is usually 0.1 to 20% by weight, preferably 0.5 to 10% by weight.
- the hindered amine light stabilizer is usually in the range of 0.1 to 10% by weight, preferably 0.5 to 5% by weight, more preferably 1 to 3% by weight.
- the addition amount of the ultraviolet absorber and the hindered amine light stabilizer is within the above range, the effect of improving the weather resistance of the cured resin obtained by polymerizing the composition of the present invention and a molded article comprising the resin is increased. .
- the addition amount of the ultraviolet absorber and the hindered amine light stabilizer is less than the above range, the effect of improving the weather resistance of the obtained molded product tends to be small.
- the addition amount of the ultraviolet absorber or the hindered amine light stabilizer exceeds the above range, it may be insufficient when the composition containing the polymerization reactive compound is polymerized with radiation such as UV.
- a light control dye or a light control pigment may be added.
- typical photochromic dyes or photochromic dyes for example, one or two or more of spiropyran compounds, spirooxazine compounds, fulgide compounds, naphthopyran compounds, and bisimidazole compounds may be used depending on the desired coloration. Can be used.
- spiropyran compounds examples include indole and spirobenzopyran indole rings and benzene rings substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl groups, etc., indolinospironaphthopyran indole rings and Each substituted product in which the naphthalene ring is substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., each substitution in which the indole ring of indinospiroquinolinopyran is substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc. And indolinospiropyridopyran indole ring substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group and the like.
- spirooxazine-based compounds examples include indolinospirobenzoxazine substituted with indole ring and benzene ring substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc., indolinospironaphthoxazine
- indole and naphthalene ring is substituted with halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc.
- indole ring of indinospirophenanthrooxazine is halogen, methyl, ethyl, methylene, ethylene, hydroxyl group, etc.
- Examples of the fulgide compound include N-cyanomethyl-6,7-dihydro-4-methyl-2-phenylspiro (5,6-benzo [b] thiophenedicarboximide-7,2′-tricyclo [3. 3.1.1 3,7 ] decane], N-cyanomethyl-6,7-dihydro-2- (p-methoxyphenyl) -4-methylspiro (5,6-benzo [b] thiophenedicarboximide-7, 2′-tricyclo [3.3.1.1 3,7 ] decane), 6,7-dihydro-N-methoxycarbonylmethyl-4-methyl-2-phenylspiro (5,6-benzo [b] thiophene Carboximido-7,2′-tricyclo [3.3.1.1 3,7 ] decane), 6,7-dihydro-4-methyl-2- (p-methylphenyl) -N-nitromethylspiro (5 , 6-Benzo [b Thiophene-dicarboximi
- naphthopyran compounds examples include spiro [norbornane-2,2 ′-[2H] benzo [h] chromene], spiro [bicyclo [3.3.1] nonane-9,2 ′-[2H] benzo [ h] chromene], 7'-methoxyspiro [bicyclo [3.3.1] nonane-9,2 '-[2H] benzo [h] chromene], 7'-methoxyspir [norbornane-2,2'-[2H] ] Benzo [f] chromene], 2,2-dimethyl-7-octoxy [2H] benzo [h] chromene, spiro [2-bicyclo [3.3.1] nonene-9,2 '-[2H] benzo [ h] chromene], spiro [2-bicyclo [3.3.1] nonene-9,2 ′-[2H] benzo [f] chromene], 6-morpholino-3,3-bis (3-
- the amount of these light control dyes or light control pigments is not particularly limited, but is in the range of about 0.01 to 10000 ppm (by weight), preferably 0.1 to 1000 ppm, based on the composition containing the polymerization reactive compound.
- the range is (weight), more preferably 1 to 100 ppm (weight).
- the composition of the present invention further includes a polymerization accelerator, a catalyst, an infrared absorber, a radical scavenger, an antioxidant, a polymerization inhibitor, a non-light-controlling dye and dye, a binder, a dispersant, and a leveling.
- a polymerization accelerator such as aluminum silicate, aluminum silicate, aluminum silicate, aluminum silicate, aluminum silicate, aluminum silicate, aluminum silicates, sodium silicate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium bicarbonate, sodium
- the cured resin of the present invention and a molded body made of the resin are produced by adding a polymerization reactive compound and, if necessary, the above-mentioned various additives. Moreover, you may add to the composition of this invention the polymerization reactive compound and additive which are not described in this application in the range which does not impair the effect of this invention.
- the cured resin constituting the molded body of the present invention is preferably a cured resin obtained from a liquid composition that can be easily cast, and among these cured resins, the cured resins described in the following (a) to (z): Is preferred.
- poly (thio) urethane resin means polyurethane resin, polythiourethane resin and polydithiourethane resin. To do.
- poly (thio) urea resin means polyurea resin and polythiourea resin.
- C Poly (thio) epoxy resin polymerized with poly (thio) epoxy compound
- d Poly (thio) epoxy-poly (thi) ol resin polymerized with poly (thio) epoxy compound and poly (thio) ol compound
- e Poly (thio) epoxy-polyamine resin polymerized with poly (thio) epoxy compound and polyamine compound
- f Poly (thio) epoxy-acid anhydride resin polymerized with poly (thio) epoxy compound and acid anhydride
- g Poly (meth) acryloyl resin polymerized by poly (meth) acryloyl compound
- h Poly (meth) acryloyl-poly (thi) ol resin polymerized by poly (meth) acryloyl compound and
- More preferable cured resins include the cured resins described in (a) to (f), (s) to (v), and (z) and mixed resins thereof.
- ⁇ Optical material> various shapes of molded articles can be obtained by changing the mold during polymerization.
- the molded body of the present invention can be used as various optical materials by forming a desired shape and providing a coat layer or other members formed as necessary.
- the optical material include a plastic lens, a light emitting diode (LED), a prism, an optical fiber, an information recording substrate, a filter, and a light emitting diode.
- LED light emitting diode
- prism prism
- an optical fiber an information recording substrate
- a filter a light emitting diode
- it is suitable as a plastic lens.
- the plastic lens which consists of a molded object of this invention is demonstrated.
- the plastic lens can be manufactured as follows.
- the plastic lens of the present invention is usually produced by a casting polymerization method using the above-described composition. Specifically, first, an internal mold release agent containing at least one phosphoric acid diester compound A of the general formula (1) is added to a composition containing a polymerization reactive compound, mixed and stirred, and reduced in pressure as necessary. Defoaming is performed.
- composition of the present invention is injected into a cavity composed of a glass mold and a gasket or tape, and is cured or cured by irradiation with radiation such as ultraviolet rays other than infrared rays, and the cured resin of the present invention and the resin thereof.
- radiation such as ultraviolet rays other than infrared rays
- a plastic lens is manufactured.
- the heating is usually gradually raised from a low temperature for several days for the purpose of preventing nonuniform polymerization (stria) due to convection.
- stria nonuniform polymerization
- the temperature is gradually raised from a low temperature in the range of 0 to 200 ° C. for 64 hours, similarly in the range of 5 to 150 ° C. for 40 hours, and similarly in the range of 20 to 120 ° C. for 16 hours.
- the polymerization in order to prevent polymerization nonuniformity (striasis) due to convection, the polymerization is usually performed gradually by dividing the irradiation of radiation or reducing the illuminance. It is done. In order to prevent more convection, after injecting a uniform polymerizable reaction composition into the cavity, it is cooled once to form a state in which convection hardly occurs, and then a weak radiation is irradiated to form a uniform gel state. In some cases, a dual cure method or the like in which the formed semi-cured composition is completely cured by heating may be employed.
- the plastic lens obtained by releasing from the mold may be subjected to a reheating treatment (annealing) as necessary for the purpose of completing the polymerization or removing distortion caused by residual stress.
- heat treatment is performed in the range of 1 to 24 hours at a temperature Tg to Tg ⁇ 2 times that of the obtained plastic lens. More preferably, the heat treatment conditions are 1 to 16 hours at a temperature of Tg to Tg ⁇ 1.5 times, and more preferably the heat treatment conditions are 1 to 4 hours at a temperature of Tg to Tg ⁇ 1.2 times. It is done.
- the curable resin of the present invention and a plastic lens made of the resin are produced by radiation
- energy rays having a wavelength region of 0.0001 to 800 nm are usually used as radiation.
- the radiation is classified into ⁇ -rays, ⁇ -rays, ⁇ -rays, X-rays, electron beams, ultraviolet rays, visible light, and the like, and can be appropriately selected and used according to the composition of the mixture.
- ultraviolet rays are preferable, and the output peak of ultraviolet rays is preferably in the range of 200 to 450 nm, more preferably in the range of 230 to 445 nm, still more preferably in the range of 240 to 430 nm, and particularly preferably in the range of 250 to 400 nm.
- the output peak of ultraviolet rays is preferably in the range of 200 to 450 nm, more preferably in the range of 230 to 445 nm, still more preferably in the range of 240 to 430 nm, and particularly preferably in the range of 250 to 400 nm.
- ultraviolet absorber or a hindered amine stabilizer when added to the composition, it is preferable to use ultraviolet rays having an ultraviolet energy output peak in the range of 250 to 280 nm or 370 to 430 nm. It is in.
- the cured resin of the present invention thus obtained and the plastic lens comprising the resin have functions such as a hard coat, antireflection coat, light control coat, slipperiness coat or slipperiness treatment, and antistatic coat on the surface.
- a protective coat layer, dyeing treatment for imparting fashion, polishing the surface and edges, etc., and putting a polarizing film inside or attaching it to the surface for the purpose of imparting polarization You may perform processing etc. which attach or give various functionality.
- the surface of the obtained cured resin of the present invention and the plastic lens made of the resin is subjected to corona treatment, ozone treatment, oxygen gas or nitrogen.
- Physical or chemical treatment such as low-temperature plasma treatment using gas or the like, glow discharge treatment, oxidation treatment with chemicals, or flame treatment can also be performed.
- the surface of the cured resin of the present invention and the plastic lens made of the resin and the outermost layer (atmospheric contact surface) formed by the above physical or chemical treatment or the like may be provided therebetween.
- the coating agent used for the primer layer examples include polyester resins, polyamide resins, polyurethane resins, epoxy resins, phenol resins, (meth) acrylic resins, polyvinyl acetate resins, polyethylene, and polypropylene.
- a coating agent containing a resin such as a polyolefin resin or a copolymer or modified resin thereof, or a cellulose resin as a main component of the vehicle can be used.
- the coating agent may be either a solvent type coating agent or an aqueous type coating agent.
- modified polyolefin coating agents ethyl vinyl alcohol coating agents, polyethyleneimine coating agents, polybutadiene coating agents, polyurethane coating agents; Polyester polyurethane emulsion coating agent, polyvinyl chloride emulsion coating agent, retane acrylic emulsion coating agent, silicone acrylic emulsion coating agent, vinyl acetate acrylic emulsion coating agent, acrylic emulsion coating agent; Styrene-butadiene copolymer latex coating agent, acrylonitrile-butadiene copolymer latex coating agent, methyl methacrylate-butadiene copolymer latex coating agent, chloroprene latex coating agent, rubber-based latex coating agent of polybutadiene latex, polyacrylic acid ester A latex coating agent, a polyvinylidene chloride latex coating agent, a polybutadiene latex coating agent, or a coating agent comprising a carboxylic acid-modified latex or
- These coating agents can be applied by, for example, a dipping coating method, a spin coating method, and a spray coating method, and the coating amount on the substrate is usually 0.05 g / m in a dry state. 2 to 10 g / m 2 .
- polyurethane-based coating agents are more preferable.
- the polyurethane-based coating agent has a urethane bond in the main chain or side chain of the resin contained in the coating agent.
- a polyurethane-type coating agent is a coating agent containing the polyurethane obtained by making polyol and isocyanate compounds, such as polyester polyol, polyether polyol, or acrylic polyol, react, for example.
- polyurethane coating agents obtained by mixing polyester polyols such as condensation polyester polyols and lactone polyester polyols with isocyanate compounds such as tolylene diisocyanate, hexamethylene diisocyanate, and xylene diisocyanate are closely attached. It is preferable because of its excellent properties.
- the method of mixing the polyol compound and the isocyanate compound is not particularly limited.
- the mixing ratio is not particularly limited, but if the isocyanate compound is too small, it may cause curing failure, so that the OH group of the polyol compound and the NCO group of the isocyanate compound are in the range of 2/1 to 1/40 in terms of equivalents. Is preferred.
- the cured resin of the present invention can be applied to other than plastic lenses, and examples of applications other than plastic lenses include sheets and films manufactured in the same manner as plastic lenses using a flat mold. . Sheets and films made of the cured resin of the present invention are functionally formed by physically or chemically treating their surfaces in the same manner as plastic lenses, or by the primer layer and physical or chemical treatment described above. The outermost layer (atmospheric contact surface) may be laminated.
- the plastic lens made of the cured resin of the present invention is a laminate comprising the above-mentioned primer layer between the functional outermost layer (atmospheric contact surface) formed by the physical or chemical treatment and the cured resin surface. There may be.
- the plastic lens of the present invention thus obtained can be used for various lens applications such as eyeglass lenses, camera lenses, pickup lenses, Furnell lenses, prism lenses, and lenticular lenses.
- lens applications such as eyeglass lenses, camera lenses, pickup lenses, Furnell lenses, prism lenses, and lenticular lenses.
- particularly preferred applications include eyeglass lenses, camera lenses, and pickup lenses having a smooth surface.
- bubbles are likely to form near the interface with the mold (after the mold release, near the lens surface). Therefore, in addition to the internal mold release agent of the present invention, this is an application that requires further contrivance.
- the sheet and film of the present invention obtained in the same manner are display members such as flat panels and smartphone panels, scattering prevention films, specific wavelength cut films, film members such as decorative films, building material window glass, vehicle window glass, mirrors, etc. It can be used for various planar member applications that require high transparency, such as glass replacement members.
- the molded body made of a cured resin and the plastic lens were evaluated by the following method.
- ⁇ Releasability> The releasability when peeling the mold from the molded body at room temperature was evaluated according to the following criteria. ⁇ Very good When the surface is cooled to room temperature, the entire contact surface between the mold and the molded body already peels naturally. ⁇ : Good At the time of cooling to room temperature, a part of the adhesion surface between the mold and the molded body has already peeled naturally, and the mold release operation (to the adhesion surface between the obtained molded body and the molded mold, wedge type The mold release tool is inserted and the molded body is peeled off from the mold.).
- ⁇ Slightly defective Even when cooled to room temperature, the mold and the molded body are in close contact with each other, and a mold release operation (a wedge-shaped mold release jig is inserted into the contact surface between the obtained molded body and the molded mold to remove the molded body. It can be finally peeled off by removing from the mold. The lens or mold may be missing.
- ⁇ Poor even after cooling to room temperature, and then performing a mold release operation (insert a wedge-shaped mold release jig into the adhesion surface of the obtained molded product and the molded mold and peel the molded product from the mold). And the compact are in close contact.
- the phosphate ester (110A) containing the following phosphate diester (110) was obtained by the following known method. 27.0 g of phosphorus oxychloride (manufactured by Wako Pure Chemical Industries, Ltd.) was dissolved in 30 g of tetrahydrofuran and cooled to 0 ° C. To this solution was added dropwise a mixed solution of 43.7 g of a tri (propylene glycol) n-butyl ether isomer mixture (DOWANOL TPnB manufactured by Dow), 17.8 g of triethylamine and 20 g of tetrahydrofuran over 30 minutes.
- DOWANOL TPnB a tri (propylene glycol) n-butyl ether isomer mixture
- the temperature of the reaction solution was 5 to 10 ° C. After completion of dropping, the mixture was aged at 35 ° C. for 2 hours. Thereafter, the reaction solution was further cooled to 0 ° C., and a solution of 32.8 g of 1-dodecanol (manufactured by Wako Pure Chemical Industries, Ltd.), 17.8 g of triethylamine and 20 g of tetrahydrofuran was added dropwise over 30 minutes. At the time of dropwise addition, the temperature of the reaction solution was 5 to 10 ° C. After completion of the dropwise addition, the temperature was gradually raised and the mixture was further aged at 20 ° C. for 10 hours.
- reaction solution was cooled to 0 ° C., a solution obtained by dissolving 28.2 g of sodium hydroxide in 40 g of ion-exchanged water was added dropwise over 30 minutes, and the mixture was stirred at 0 ° C. for 2 hours.
- a solution obtained by dissolving 28.2 g of sodium hydroxide in 40 g of ion-exchanged water was added dropwise over 30 minutes, and the mixture was stirred at 0 ° C. for 2 hours.
- 300 mL of 3N hydrochloric acid was added to the reaction solution to make the reaction solution acidic
- the produced phosphate ester was extracted with 200 g of diethyl ether.
- the organic layer was separated and further washed with ion exchange water (100 mL ⁇ 4).
- Identification data of phosphoric acid diester (110) is shown in FIG. 1 ( 1 H-NMR spectrum chart) and FIG. 2 (IR spectrum chart).
- Preparation Example 2 The following phosphoric acid diester (100) was obtained by the following known method.
- the raw material tri (propylene glycol) n-butyl ether isomer mixture and 1-dodecanol were changed to alcohol (300) and tridecanol represented by the following formula (300), respectively, and synthesis was performed.
- the phosphoric acid diester (100) represented by the following formula (100) was obtained. Identification data of the obtained phosphoric acid diester (100) are shown in FIG. 3 ( 1 H-NMR spectrum chart), FIG. 4 (electrospray mass spectrometry chart) and FIG. 5 (IR spectrum chart).
- a phosphoric acid diester (120) represented by the following formula (120) was produced. That is, 100 g of monotrioxyethylene lauryl phosphoric acid, 66.6 g of potassium hydroxide, and 157.0 g of ion-exchanged water were mixed, heated to 70 ° C. and dissolved. To this solution, 117.0 g of diethyl sulfuric acid was added dropwise over 8 hours. After completion of dropping, the mixture was aged at 70 ° C. for 4 hours. The reaction mixture was acidified with hydrochloric acid and extracted three times with 250 mL of ether. The residue obtained by distilling off ether under reduced pressure was recrystallized from ethanol to obtain phosphoric acid diester (120).
- phosphoric acid diester (130) represented by the following formula (130) was produced. That is, 300 g of isooctylphenylnonoxyethylene glycol and 54 g of ethyl metaphosphate were placed in a reaction vessel and stirred at 70 ° C. for 3.5 hours to obtain a phosphoric acid diester (130).
- Example 1 As an internal mold release agent, 0.01 parts by weight (500 ppm) of the phosphoric acid diester (100) represented by the above formula (100), and 2- (2′-hydroxy-5′-t-octylphenyl) as a UV absorber Benzotriazole (trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.) 0.3 parts by weight (15,000 ppm), 0.01 parts by weight (500 ppm) of dimethyltin (II) dichloride as a catalyst, and tolylene diisocyanate as a polymerization reactive compound 14 parts by weight and 3.19 parts by weight of hexamethylene diisocyanate were stirred and mixed at 20 ° C.
- Benzotriazole trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.
- This polymerizable composition was degassed for 30 minutes under a reduced pressure of 0.13 kPa, and then filtered through a 1 ⁇ m PTFE filter to form a cavity made of a glass mold and a tape (curve shape: 4 curves on both concave and convex surfaces, Center thickness: 2 mm) and sealed with tape.
- This was placed in a polymerization oven, gradually heated from 25 ° C. to 130 ° C. over 19 hours, and then held at 130 ° C. for 2 hours for polymerization. After cooling, the glass mold and the tape were peeled off, and a molded body (plastic lens) made of a cured resin formed inside was taken out.
- Example 2 The amount of the phosphoric acid diester (100) represented by the above formula (100) was changed as shown in Table 1 to prepare a molded body (plastic lens) in the same manner as in Example 1, The transparency was confirmed. The results are shown in Table 1.
- Example 3 The phosphor diester (100) was changed to a phosphoric acid ester (110A) containing the phosphoric acid diester (110) represented by the above formula (110), and the addition amount was 1000 ppm. (Plastic lens) was prepared, and the releasability and transparency were confirmed. The results are shown in Table 2.
- Example 4 The phosphoric acid diester (100) was changed to the phosphoric acid diester (120) represented by the above formula (120), and the addition amount was 1000 ppm to prepare a molded body (plastic lens) in the same manner as in Example 1, The moldability and transparency were confirmed. The results are shown in Table 2.
- Example 5 A molded article (plastic lens) was prepared in the same manner as in Example 1 except that the phosphoric acid diester (100) was changed to the phosphoric acid diester (130) represented by the above formula (130) and the addition amount was 1000 ppm. The moldability and transparency were confirmed. The results are shown in Table 2.
- Example 6 The phosphoric diester (100) was changed to the above internal mold release agent A, and the amount of internal mold release agent A added was changed as shown in Table 3 to obtain a molded product (plastic) as in Example 1. Lens) was prepared, and the releasability and transparency were confirmed. The results are shown in Table 3.
- a molded product (plastic lens) was prepared in the same manner as in Example 6 by changing the internal mold release agent A to internal mold release agents B, C, and D containing the compound at the following composition ratio. The sex was confirmed. The results are shown in Table 3.
- the internal mold release agent B was synthesized based on the description in JP-A No. 2000-281687, the internal mold release agent C was JP-506H manufactured by Johoku Chemical Industry Co., Ltd., and the internal mold release agent D was Stepan. ZelecUN made by the company.
- Example 7 A molded body (plastic lens) was prepared in the same manner as in Example 1 except that the phosphoric acid diester (100) was changed to the internal mold release agent A (1000 ppm) and the internal mold release agent D (500 ppm). And the transparency was confirmed. The results are shown in Table 3.
- Preparation Example 6 At room temperature, the internal mold release agent A obtained in Preparation Example 5 was neutralized with 28 wt% sodium methoxide (PH 7.3), and the mixed methanol was removed under reduced pressure to obtain the compound at the following composition ratio. An internal release agent A-Na containing was obtained.
- Example 8 A molded body (plastic lens) was prepared in the same manner as in Example 6 except that the internal release agent A-Na was used in place of the internal release agent A, and the release property and transparency were confirmed. The results are shown in Table 4.
- Example 9 A molded body (plastic lens) was prepared in the same manner as in Example 6 except that the internal mold release agent A-Amine containing the compound at the following composition ratio was used in place of the internal mold release agent A. The transparency was confirmed. The results are shown in Table 4.
- Example 4 A molded body (plastic lens) was prepared in the same manner as in Example 6 except that the internal release agent B-Na was used in place of the internal release agent A, and the release property and transparency were confirmed. The results are shown in Table 4.
- Example 10 To a 100 ml sample bottle, the addition amount of the internal mold release agent A was changed in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm), and then 2- (2′-hydroxy-5 as UV absorber) '-T-octylphenyl) benzotriazole (trade name Biosorb 583 manufactured by Kyodo Yakuhin Co., Ltd.) 0.3 parts by weight (15,000 ppm), dibutyltin (II) dichloride 0.01 parts by weight (500 ppm) as a catalyst, polymerization reactivity As a compound, 10.12 parts by weight of 2,5 (6) -bis (isocyanatomethyl) bicyclo- [2.2.1] -heptane was added and mixed with stirring at 20 ° C.
- 2- (2′-hydroxy-5 as UV absorber) '-T-octylphenyl) benzotriazole trade name Biosorb 583 manufactured by Kyodo Yakuhin Co., Ltd.
- compositions were degassed for 30 minutes under a reduced pressure of 0.13 kPa, then filtered through a 1 ⁇ m PTFE filter, and a cavity formed of a glass mold and tape (curve shape: 4 curves for both concave and convex surfaces, center thickness) : 2 mm) and sealed with tape. These were placed in a polymerization oven, gradually heated from 25 ° C. to 120 ° C. over 19 hours, and then held at 120 ° C. for 2 hours for polymerization. After cooling, the glass mold and the tape were peeled off, and a molded body (plastic lens) made of a cured resin formed inside was taken out.
- a molded body plastic lens
- the obtained molded body (plastic lens) was colorless and transparent and had a refractive index of ne1.60, an Abbe number ⁇ e40, and a Tg of 114 ° C.
- Table 5 shows the evaluation results of releasability and transparency.
- Example 11 To a 100 ml sample bottle, the addition amount of the internal mold release agent A was changed in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm), and then 2- (2′-hydroxy-5 as UV absorber) '-T-octylphenyl) benzotriazole (trade name Biosorb 583 manufactured by Kyodo Yakuhin Co., Ltd.) 0.3 parts by weight (15,000 ppm), dibutyltin (II) dichloride 0.01 parts by weight (500 ppm) as a catalyst, polymerization reactivity As a compound, 10.12 parts by weight of m-xylylene diisocyanate was stirred and mixed at 20 ° C.
- 2- (2′-hydroxy-5 as UV absorber) '-T-octylphenyl) benzotriazole trade name Biosorb 583 manufactured by Kyodo Yakuhin Co., Ltd.
- dibutyltin (II) dichloride 0.01 parts by weight (500 pp
- compositions were degassed for 30 minutes under a reduced pressure of 0.13 kPa, then filtered through a 1 ⁇ m PTFE filter, and a cavity composed of a glass mold and a tape (curve shape: 4 curves on both concave and convex surfaces, Center thickness: 2 mm) and sealed with tape. These were placed in a polymerization oven, gradually heated from 25 ° C. to 120 ° C. over 19 hours, and then held at 120 ° C. for 2 hours for polymerization. After cooling, the glass mold and the tape were peeled off, and a molded body (plastic lens) made of a cured resin formed inside was taken out. The obtained molded body (plastic lens) was colorless and transparent, had a refractive index of 1.67, an Abbe number ⁇ e31, and a Tg of 98 ° C. Table 5 shows the evaluation results of releasability and transparency.
- Example 12 In seven 100 ml sample bottles, 0.004 parts by weight of N, N-dimethylcyclohexylamine as a catalyst, 0.018 parts by weight of N, N-dicyclohexylmethylamine, and 5,7-dimercaptomethyl-1 as a polymerization reactive compound , 11-dimercapto-3,6,9-trithiaundecane, 4,7-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane, 4,8-dimercaptomethyl-1,11 -1.83 parts by weight of a mixture of dimercapto-3,6,9-trithiaundecane was added and stirred and mixed at 20 ° C.
- the internal mold release agent A was added to 7 different 100 ml sample bottles in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm) with the addition amount changed as shown in Table 5, and then 2 as a UV absorber.
- -(2-Hydroxy-5-t-butylphenyl) -2H-benzotriazole (trade name Tinuvin PS manufactured by BASF) 0.2 parts by weight (10,000 ppm), and bis (2,3-epi After adding 17.17 parts by weight of thiopropyl) disulfide, the mixture was stirred and mixed at 20 ° C. to obtain 7 kinds of uniform solution (2).
- the uniform solution (1) was added to these seven kinds of uniform solutions (2) and stirred at 20 ° C.
- the obtained molded body (plastic lens) was colorless and transparent, had a refractive index of ne1.74, an Abbe number ⁇ e32, and a Tg of 78 ° C.
- Table 5 shows the evaluation results of releasability and transparency.
- Example 13 To seven 100 ml sample bottles, the addition amount of the internal release agent A was added in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm) as shown in Table 5, and then tetrabutyl as a catalyst.
- molded body made of a cured resin formed inside was taken out.
- the obtained molded body (plastic lens) was colorless and transparent, had a refractive index of ne1.64, an Abbe number ⁇ e35, and a Tg of 64 ° C. Table 5 shows the evaluation results of releasability and transparency.
- Example 14 To the 100 ml sample bottle, the addition amount of the internal release agent A was added in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm) as shown in Table 5, and then 2-hydroxy-as a UV absorber. 4-methylbenzophenone 0.01 part by weight (500 ppm), 1,1-di (t-hexylperoxy) cyclohexane 0.6 part by weight (30,000 ppm) as a polymerization initiator, and diethylene glycol bis ( 20.0 parts by weight of allyl carbonate) were stirred and mixed at 20 ° C. to obtain 7 kinds of polymerizable compositions.
- 1,1-di (t-hexylperoxy) cyclohexane 0.6 part by weight (30,000 ppm) as a polymerization initiator
- diethylene glycol bis 20.0 parts by weight of allyl carbonate
- Example 15 To the 100 ml sample bottle, the addition amount of the internal release agent A was added in the range of 0 to 0.1 parts by weight (0 to 5,000 ppm) as shown in Table 5, and then 2-hydroxy-as a UV absorber. 4-methylbenzophenone 0.01 part by weight (500 ppm), 1,1-di (t-hexylperoxy) cyclohexane 0.6 part by weight (30,000 ppm) as a polymerization initiator, and divinylbenzene 5 as a polymerization reactive compound 0.0 part by weight, ethoxybisphenol A diacrylate (NK Ester A-BPE-10 (manufactured by Shin-Nakamura Chemical Co., Ltd.)) Obtained.
- 4-methylbenzophenone 0.01 part by weight (500 ppm), 1,1-di (t-hexylperoxy) cyclohexane 0.6 part by weight (30,000 ppm) as a polymerization initiator, and divinylbenzene 5 as
- Example 16 In a 100 ml sample bottle, 0.02 part by weight (1,000 ppm) of internal mold release agent A and 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole (manufactured by Kyodo Yakuhin Co., Ltd.) as UV absorber Biosorb 583) 0.3 parts by weight (15,000 ppm), dimethyltin (II) dichloride 0.008 parts by weight (400 ppm) as a catalyst, 2,5 (6) -bis (isocyanatomethyl) bicyclo as a polymerization reactive compound -[2.2.1] -Heptane (5.84 parts by weight) and hexamethylene diisocyanate (3.89 parts by weight) were added and stirred and mixed at 20 ° C.
- 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole manufactured by Kyodo Yakuhin Co., Ltd.
- UV absorber Biosorb 583 0.3 parts by weight (1
- Example 17 Internal release agent A 0.10 parts by weight, biosorb 583 (ultraviolet absorber: registered trademark, manufactured by Kyodo Pharmaceutical Co., Ltd.) 1.5 parts by weight, N-benzyl-2-methylimidazole 0.028 parts by weight, and 1,5 -23.9 parts by weight of pentamethylene diisocyanate was mixed and dissolved by stirring for 15 minutes at room temperature, and then 27.9 parts by weight of the 1,5-pentamethylene diisocyanate modified composition was mixed to prepare a polyisocyanate liquid. The isocyanurate mononuclear concentration of this polyisocyanate liquid was 35%.
- This homogeneous solution was degassed for 30 minutes at room temperature and under reduced pressure, filtered through a 1 ⁇ m Teflon (registered trademark) filter, and then a mold mold composed of a glass mold and a tape (curve shape: 4 curves on both concave and convex surfaces, Center thickness: 2 mm).
- a mold mold composed of a glass mold and a tape (curve shape: 4 curves on both concave and convex surfaces, Center thickness: 2 mm).
- This was put into an oven and polymerized by gradually raising the temperature from 25 ° C. to 120 ° C. over about 24 hours. After completion of the polymerization, the mold was taken out of the oven, released from the mold, and then annealed at 120 ° C. for 2 hours to obtain a resin molded body.
- the resin molded body had a colorless and transparent appearance, and had a refractive index (ne) of 1.60, an Abbe number ( ⁇ e) of 39, and a heat resistance of 89 ° C.
- Table 6 shows the evaluation results of releasability and transparency.
- Example 18 Internal release agent A 0.1 parts by weight (1,000 ppm), 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole (trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.) as a UV absorber 5 parts by weight (15,000 ppm) and 58.9 parts by weight of bis (4-isocyanatocyclohexyl) methane were stirred and mixed at 20 ° C. to obtain a uniform solution.
- 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.
- This mixed solution was defoamed at 600 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then poured into a 4C glass plate for a planar plate having a center thickness of 2 mm and a diameter of 80 mm.
- This mold was put into a polymerization oven and polymerized by gradually raising the temperature from 20 ° C. to 130 ° C. over 21 hours. After completion of the polymerization, the mold was taken out from the oven. The obtained planar lens was further annealed at 130 ° C. for 2 hours.
- the obtained planar lens with a thickness of 2 mm was transparent, had a refractive index (ne) of 1.60, an Abbe number ( ⁇ e) of 39, and a heat resistance of 136 ° C., and was suitable as a transparent resin for optical materials.
- Table 6 shows the evaluation results of releasability and transparency.
- a composition was prepared by mixing 47.0 parts by weight of a mixture of 4,8-dimercaptomethyl-1,11-dimercapto-3,6,9-trithiaundecane.
- the obtained polymerization raw material was filtered through a 1.0 ⁇ m Teflon (registered trademark) filter and degassed for 60 minutes under a vacuum of 400 Pa or less.
- the degassed composition was poured into a mold mold made of 4C Plano glass mold having a center thickness of 2 mm and a diameter of 80 mm and a tape. Thereafter, polymerization was carried out in a heating furnace at 25 ° C. to 120 ° C. for 20 hours, and after cooling, the glass mold and the tape were removed to obtain a thiourethane molded product. Furthermore, annealing was performed at 130 ° C. for 2 hours.
- the obtained planar lens having a thickness of 2 mm was transparent, had a refractive index (ne) of 1.60, an Abbe number ( ⁇ e) of 38, and a heat resistance of 130 ° C., and was suitable as a transparent resin for optical materials. Table 6 shows the evaluation results of releasability and transparency.
- Example 20 0.10 parts by weight of internal mold release agent A, 0.17 parts by weight of dibutyltin (II) dichloride, 1.50 parts by weight of 2- (2-hydroxy-5-tert-octylphenyl) -2H-benzotriazole Kogyo Co., Ltd., trade name Viosorb583), isophorone diisocyanate 23.2 parts by weight, hexamethylene diisocyanate 19.8 parts by weight were mixed with stirring. Thereafter, 57.0 parts by weight of pentaerythritol tetrakis (3-mercaptopropionate) was mixed to prepare a composition.
- II dibutyltin
- the obtained polymerization raw material was filtered through a 1.0 ⁇ m Teflon (registered trademark) filter and degassed for 60 minutes under a vacuum of 400 Pa or less.
- the degassed composition was poured into a mold mold made of 4C Plano glass mold having a center thickness of 2 mm and a diameter of 80 mm and a tape. Thereafter, polymerization was carried out in a heating furnace at 35 ° C. to 130 ° C. for 21 hours, and after cooling, the glass mold and tape were removed to obtain a thiourethane molded product. Furthermore, annealing was performed at 130 ° C. for 2 hours.
- the obtained planar lens having a thickness of 2 mm was transparent, had a refractive index (ne) of 1.56, an Abbe number ( ⁇ e) of 41 and a heat resistance of 82 ° C., and was suitable as a transparent resin for optical materials.
- Table 6 shows the evaluation results of releasability and transparency.
- Example 21 Internal release agent A 0.1 part by weight (1,000 ppm), 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole (trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.) as a UV absorber 0 parts by weight (20,000 ppm), 27.6 parts by weight of bis (4-isocyanatocyclohexyl) methane and 27.6 parts by weight of isophorone diisocyanate were stirred and mixed at 20 ° C. to obtain a uniform solution.
- 2- (2′-hydroxy-5′-t-octylphenyl) benzotriazole trade name Biosorb 583, manufactured by Kyodo Yakuhin Co., Ltd.
- This mixed solution was defoamed at 600 Pa for 1 hour, filtered through a 1 ⁇ m PTFE filter, and then poured into a 4C glass plate for a planar plate having a center thickness of 2 mm and a diameter of 80 mm.
- This mold was put into a polymerization oven and polymerized by gradually raising the temperature from 20 ° C. to 130 ° C. over 21 hours. After completion of the polymerization, the mold was taken out from the oven. The obtained planar lens was further annealed at 130 ° C. for 2 hours.
- the obtained planar lens having a thickness of 2 mm was transparent, had a refractive index (ne) of 1.60, an Abbe number ( ⁇ e) of 38, and a heat resistance of 117 ° C., and was suitable as a transparent resin for optical materials.
- Table 6 shows the evaluation results of releasability and transparency.
- Example 22 Internal release agent A 1.0 part by weight (10,000 ppm) and propylene oxide adduct of trimethylolpropane (manufactured by Bayer; Desmophen 4011T) 58.8 parts by weight, TINUVIN 292 (manufactured by BASF; light stabilizer) 40 parts by weight (4,000 ppm) was mixed and dissolved to obtain a uniform solution.
- a benzotriazole compound manufactured by Kyodo Yakuhin; Biosorb 583 (2- (2′-hydroxy-5′-tert- Octylphenyl) benzotriazole) 1.50 parts by weight (15,000 ppm) was mixed and dissolved to obtain a uniform solution.
- the respective solutions were mixed at 20 ° C., defoamed at 400 Pa, and then poured into a 4C planar mold for molding having a diameter of 80 mm. This was put into a polymerization oven and polymerized by gradually raising the temperature from 15 ° C. to 120 ° C. over 24 hours.
- the product was taken out from the oven and released from the mold.
- the releasability was good and no mold peeling was observed.
- the obtained molded body was further annealed at 120 ° C. for 2 hours.
- the obtained molded body was transparent, no striae were observed, the refractive index (ne) was 1.54, and Tg was 81 ° C., which was suitable for use as an optical material.
- Table 6 shows the evaluation results of releasability and transparency.
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Abstract
Description
また、界面活性剤であるリン酸エステルの製造方法についての提案も行われている(特許文献13)。
即ち、本発明は、従来の内部離型剤よりも離型性と透明性に優れる内部離型剤、この内部離型剤を含む組成物および該組成物を用いたプラスチックレンズの製造方法を提供することを課題とする。
[1] 下記一般式(1)
で表されるリン酸ジエステル化合物を少なくとも1種含む、内部離型剤。
[2] 重合反応性化合物と、[1]に記載の前記内部離型剤を含む、組成物。
[3] 該重合反応性化合物に対する一般式(1)で表される前記リン酸ジエステル化合物の量が、1×10-1~5×104ppmの範囲である、[2]に記載の組成物。
[4] 前記重合反応性化合物が、ポリイソ(チオ)シアネート化合物、ポリ(チオ)エポキシ化合物、ポリオキセタニル化合物、ポリチエタニル化合物、ポリ(メタ)アクリロイル化合物、ポリアルケン化合物、アルキン化合物、ポリ(チ)オール化合物、ポリアミン化合物、酸無水物、またはポリカルボン酸化合物から選択される1種または2種以上である、[2]または[3]に記載の組成物。
[5] [2]~[4]のいずれかに記載の組成物を重合した成形体。
[6] [5]に記載の成形体からなる、光学材料。
[7] [5]に記載の成形体からなる、プラスチックレンズ。
[8] [2]~[4]のいずれかに記載の組成物を注型重合する工程を含む、プラスチックレンズの製造方法。
[9] [8]に記載の製造方法で得られたプラスチックレンズ。
[10] 下記一般式(2)
本発明の内部離型剤は、下記一般式(1)で表されるリン酸ジエステル化合物Aを少なくとも1種含む。なお、2種以上のリン酸ジエステル化合物Aを含む場合、下記一般式(1)の基(R1,R2,R3,M)は、リン酸ジエステル化合物Aごとに同一でも異なっていてもよい。リン酸ジエステル化合物Aは、構造異性体の混合物であってもよい。
炭素数7~30のアルキルアリール基としては、トリル基(メチルフェニル基)、ジメチルフェニル基、トリメチルフェニル基、エチルフェニル基、プロピルフェニル基、ブチルフェニル基、ペンチルフェニル基、シクロヘキシルフェニル基、トリメチルフェニル基、メチルナフチル基、メチルフェナントリル基、エチルフェナントリル基、プロピルフェナントリル基等を挙げることができる。
炭素数8~30のアルキルアリールアルキル基としては、メチルベンジル基、ジメチルベンジル基、トリメチルベンジル基、ブチルベンジル基またはジブチルベンジル基等を挙げることができる。
これらの炭化水素基中の水素原子は、1つ以上の水酸基で置換されていてもよい。ただし、R1およびR2はこれら例示官能基のみに限定されるものではない。
R3として具体的には、例えば、1,2-エチレン基、1,2-プロピレン基、1,2-ブチレン基、1,3-プロピレン基、1,3-ブチレン基、1,4-ブチレン基等が挙げられる。これらの中で好ましい形態としては、1,2-エチレン基、または1,2-プロピレン基が挙げられ、最も好ましくは1,2-エチレン基が挙げられる。
好ましいアルカリ金属イオンとしては、例えば、リチウムイオン、ナトリウムイオン、カリウムイオン、ルビジウムイオン等が挙げられる。
nは1~60の整数を表し、1~40の範囲がより好ましく、1~30の範囲であれば更に好ましい。
例えば、モノメチルモノ-3,6,9-トリオキサウンデカ-1-イルリン酸、モノメチルモノ-3,6,9-トリオキサウンデカ-1-イルリン酸ナトリウム、モノエチルモノ(14-ヒドロキシ-3,6,9,12-テトラオキサテトラデカ-1-イル)リン酸、モノ(14-ヒドロキシ-3,6,9,12-テトラオキサテトラデカ-1-イル)モノオクチルリン酸、モノエチルモノ-3,6,9-トリオキサヘンイコサ-1-イルリン酸、モノブチルモノ-3,6,9,12,15,18,21-ヘプタオキサテトラトリアコント-1-イルリン酸、モノブチルモノ-3,6,9,12,15,18,21-ヘプタオキサテトラトリアコント-1-イルリン酸、モノメチルモノ(23-(ノニルフェノキシ)-3,6,9,12,15,18,21-ヘプタオキサトリコサ-1-イル)リン酸、モノメチルモノ(23-(ノニルフェノキシ)-3,6,9,12,15,18,21-ヘプタオキサトリコサ-1-イル)リン酸ナトリウム、モノメチルモノ(29-(4-ノニルフェノキシ)-3,6,9,12,15,18,21,24,27-ノナオキサノナコサ-1-イル)リン酸、モノエチルモノ(26-(イソオクチルフェノキシ)-3,6,9,12,15,18,21,24-オクタオキサヘキサコサ-1-イル)リン酸、モノヘキサデシルモノ(14-ヒドロキシ-3,6,9,12-テトラオキサテトラデカ-1-イル)リン酸、モノドデシルモノ(17-ヒドロキシ-1,4,7,10-テトラメチル-3,6,9,12,15-ペンタオキサヘプタデカ-1-イル)リン酸等が挙げられる。
なお、下記において化合物の番号は、上記反応式中の化合物の番号に対応する。
工程(A):
オキシハロゲン化リン(a)にポリアルキレングリコールモノアルキルエーテル(b)を反応させる。オキシハロゲン化リンに対してポリアルキレングリコールモノアルキルエーテルを、0.1~2当量、好ましくは0.8~1.2当量の量で加え、-60℃~100℃、好ましくは-40~50℃で1~36時間反応させる。当該工程により、化合物(c)を含む反応混合物が得られる。
工程(A)で得られた化合物(c)を含む反応混合物に、化合物(b)とは別のアルコール(d)(アルキレンオキシ構造を持たないアルコール)を添加する。オキシハロゲン化リンに対してアルコール(d)を、0.1~2当量、好ましくは0.8~1.2当量の量で加え、-60℃~100℃、好ましくは-40~50℃で1~36時間反応させる。当該工程により、リン酸ジエステルモノハライド(e)を含む反応混合物が得られる。
反応終了後、工程(B)で得られた反応混合物に、オキシハロゲン化リンに対して1~2当量の水を加え、リン酸ジエステルモノハライド(e)を加水分解することにより、リン酸ジエステル(h)を得る。この時、水酸化ナトリウム、水酸化カリウム、炭酸ナトリウム、炭酸水素ナトリウム、炭酸カリウム、炭酸水素カリウム、リン酸ナトリウム、酢酸ナトリウム、アンモニア、酢酸、塩酸、硫酸等の塩基及び酸を添加してもよい。反応温度は、0℃~100℃、好ましくは10℃~50℃である。溶液の液性はpH8以下が好ましく、pH7以下がさらに好ましい。
なお、工程(A)は前述と同様に実施することができるので、説明を省略する。
工程(D):
工程(A)で得られた化合物(c)に水を加え、工程(C)と同様に加水分解し、リン酸モノエステル体(f)を得る。
工程(D)で得られたリン酸モノエステル体(f)に、ジアルキル硫酸(g)を加えて、リン原子に結合した水酸基をエステル化して目的物(化合物(h))を得る。この際反応速度と選択性を向上させる目的で、リン原子に結合した2個の水酸基の1個を塩基で中和する方法が好ましく用いられる。用いられる塩基は特に限定されないが、水酸化ナトリウム、炭酸ナトリウム、炭酸水素ナトリウム、水酸化カリウム等のアルカリ金属が好ましく用いられる。
一般式(1)で表される構造が生み出す特異的な効果について、典型的な化合物を例に挙げて説明する。例えば、本発明のリン酸ジエステル化合物であるアルコキシポリアルキレングリコールとアルキルアルコールのリン酸ジエステル化合物Aは、アルキルアルコールとのリン酸ジエステル化合物(P原子に、2つの同一のアルキルエーテル基が結合した構造)およびアルキルアルコールとのリン酸モノエステル化合物と比較すると、リン酸ジエステル化合物Aはミセルを形成しにくい傾向にあり分散性も良好なため、透明性が高く優れた離型性を発揮する。同様に、アルコキシポリアルキレングリコールのリン酸ジエステル化合物(P原子に、2つの同一のポリ(オキシアルキレン)アルキルエーテル基が結合した構造)およびアルコキシアルキレングリコールのリン酸モノエステル化合物と比較しても、リン酸ジエステル化合物Aは高い透明性を維持しながらより優れた離型性を発揮する。即ち、本発明のリン酸ジエステル化合物Aは、従来使用されてきた、このようなリン酸ジエステル化合物またはリン酸モノエステル化合物よりも離型性および透明性に優れるため、内部離型剤として極めて有用である。
さらに、その他の成分として、原料由来のリン酸、反応溶剤等を含むことができる。
リン酸ジエステル化合物Aを0.1~99.9重量%、好ましくは1~99重量%、より好ましくは5~95重量%、特に好ましくは5~80重量%、
リン酸ジエステル化合物Bを0~99.8重量%、好ましくは0~98重量%、より好ましくは0~90重量%、特に好ましくは5~80重量%、
リン酸モノエステル化合物Cを0.05~99.85重量%、好ましくは0.5~98.5重量%、より好ましくは2.5~92.5重量%、特に好ましくは5~80重量%、
アルコールDを0.05~99.85重量%、好ましくは0.5~98.5重量%、より好ましくは2.5~92.5重量%、特に好ましくは10~85重量%、
となる量で含むことができる。
これらの数値範囲は、適宜組み合わせることができる。上記範囲であると、離型性に優れるため好ましい。
なお、本発明のリン酸ジエステルを含む内部離型剤は、他の内部離型剤と混合して用いることもできる。
本発明の組成物は、重合反応性化合物と、上述の内部離型剤とを含む。
本発明の内部離型剤に含まれる一般式(1)のリン酸ジエステル化合物Aの添加量は、重合反応性化合物を含む各種化合物、モールドの形状等によって変化するものの、重合反応性化合物に対して、1×10-1ppm~5×104ppmの範囲であり、好ましくは1ppm~2×104ppmの範囲、さらに好ましくは5ppm~1×104ppmの範囲である。
当該範囲内で一般式(1)のリン酸ジエステル化合物が含まれることにより、離型性に優れるとともに、透明性に優れる成形体を得ることができる。
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、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;
トリレンジイソシアネート、4,4'-ジフェニルメタンジイソシアネート、ジフェニルスルフィド-4,4-ジイソシアネート、フェニレン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;
ヘキサメチレンジイソチオシアネート、リジンジイソチオシアネートメチルエステル、リジントリイソチオシアネート、m-キシリレンジイソチオシアネート、ビス(イソチオシアナトメチル)スルフィド、ビス(イソチオシアナトエチル)スルフィド、ビス(イソチオシアナトエチル)ジスルフィド等の脂肪族ポリイソチオシアネート化合物;
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;
トリレンジイソチオシアネート、4,4-ジフェニルメタンジイソチオシアネート、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-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。
ビス(2,3-エポキシプロピル)スルフィド、ビス(2,3-エポキシプロピル)ジスルフィド、ビス(2,3-エポキシプロピルチオ)メタン、1,2-ビス(2,3-エポキシプロピルチオ)エタン、1,2-ビス(2,3-エポキシプロピルチオ)プロパン、1,3-ビス(2,3-エポキシプロピルチオ)プロパン、1,3-ビス(2,3-エポキシプロピルチオ)-2-メチルプロパン、1,4-ビス(2,3-エポキシプロピルチオ)ブタン、1,4-ビス(2,3-エポキシプロピルチオ)-2-メチルブタン、1,3-ビス(2,3-エポキシプロピルチオ)ブタン、1,5-ビス(2,3-エポキシプロピルチオ)ペンタン、1,5-ビス(2,3-エポキシプロピルチオ)-2-メチルペンタン、1,5-ビス(2,3-エポキシプロピルチオ)-3-チアペンタン、1,6-ビス(2,3-エポキシプロピルチオ)ヘキサン、1,6-ビス(2,3-エポキシプロピルチオ)-2-メチルヘキサン、3,8-ビス(2,3-エポキシプロピルチオ)-3,6-ジチアオクタン、1,2,3-トリス(2,3-エポキシプロピルチオ)プロパン、2,2-ビス(2,3-エポキシプロピルチオ)-1,3-ビス(2,3-エポキシプロピルチオメチル)プロパン、2,2-ビス(2,3-エポキシプロピルチオメチル)-1-(2,3-エポキシプロピルチオ)ブタン、1,5-ビス(2,3-エポキシプロピルチオ)-2-(2,3-エポキシプロピルチオメチル)-3-チアペンタン、1,5-ビス(2,3-エポキシプロピルチオ)-2,4-ビス(2,3-エポキシプロピルチオメチル)-3-チアペンタン、1-(2,3-エポキシプロピルチオ)-2,2-ビス(2,3-エポキシプロピルチオメチル)-4-チアヘキサン、1,5,6-トリス(2,3-エポキシプロピルチオ)-4-(2,3-エポキシプロピルチオメチル)-3-チアヘキサン、1,8-ビス(2,3-エポキシプロピルチオ)-4-(2,3-エポキシプロピルチオメチル)-3,6-ジチアオクタン、1,8-ビス(2,3-エポキシプロピルチオ)-4,5-ビス(2,3-エポキシプロピルチオメチル)-3,6-ジチアオクタン、1,8-ビス(2,3-エポキシプロピルチオ)-4,4-ビス(2,3-エポキシプロピルチオメチル)-3,6-ジチアオクタン、1,8-ビス(2,3-エポキシプロピルチオ)-2,5-ビス(2,3-エポキシプロピルチオメチル)-3,6-ジチアオクタン、1,8-ビス(2,3-エポキシプロピルチオ)-2,4,5-トリス(2,3-エポキシプロピルチオメチル)-3,6-ジチアオクタン、1,1,1-トリス[[2-(2,3-エポキシプロピルチオ)エチル]チオメチル]-2-(2,3-エポキシプロピルチオ)エタン、1,1,2,2-テトラキス[[2-(2,3-エポキシプロピルチオ)エチル]チオメチル]エタン、1,11-ビス(2,3-エポキシプロピルチオ)-4,8-ビス(2,3-エポキシプロピルチオメチル)-3,6,9-トリチアウンデカン、1,11-ビス(2,3-エポキシプロピルチオ)-4,7-ビス(2,3-エポキシプロピルチオメチル)-3,6,9-トリチアウンデカン、1,11-ビス(2,3-エポキシプロピルチオ)-5,7-ビス(2,3-エポキシプロピルチオメチル)-3,6,9-トリチアウンデカン等の鎖状脂肪族の2,3-エポキシプロピルチオ化合物;
1,3-ビス(2,3-エポキシプロピルチオ)シクロヘキサン、1,4-ビス(2,3-エポキシプロピルチオ)シクロヘキサン、1,3-ビス(2,3-エポキシプロピルチオメチル)シクロヘキサン、1,4-ビス(2,3-エポキシプロピルチオメチル)シクロヘキサン、2,5-ビス(2,3-エポキシプロピルチオメチル)-1,4-ジチアン、2,5-ビス[[2-(2,3-エポキシプロピルチオ)エチル]チオメチル]-1,4-ジチアン、2,5-ビス(2,3-エポキシプロピルチオメチル)-2,5-ジメチル-1,4-ジチアン等の環状脂肪族の2,3-エポキシプロピルチオ化合物;
1,2-ビス(2,3-エポキシプロピルチオ)ベンゼン、1,3-ビス(2,3-エポキシプロピルチオ)ベンゼン、1,4-ビス(2,3-エポキシプロピルチオ)ベンゼン、1,2-ビス(2,3-エポキシプロピルチオメチル)ベンゼン、1,3-ビス(2,3-エポキシプロピルチオメチル)ベンゼン、1,4-ビス(2,3-エポキシプロピルチオメチル)ベンゼン、ビス[4-(2,3-エポキシプロピルチオ)フェニル]メタン、2,2-ビス[4-(2,3-エポキシプロピルチオ)フェニル]プロパン、ビス[4-(2,3-エポキシプロピルチオ)フェニル]スルフィド、ビス[4-(2,3-エポキシプロピルチオ)フェニル]スルフォン、4,4'-ビス(2,3-エポキシプロピルチオ)ビフェニル等の芳香族の2,3-エポキシプロピルチオ化合物等を挙げることができる。
グリセロールトリアクリレート、エトキシル化トリメチロールプロパントリアクリレート、ペンタエリスリトールトリアクリレート、プロポキシル化グリセリルトリアクリレート、プロポキシル化トリメチロールプロパントリアクリレート、トリス(2-ヒドロキシエチル)イソシアヌレートトリアクリレート等のトリアクリロイル化合物;
ジトリメチロールプロパンテトラアクリレート、ジペンタエリスリトールペンタアクリレート、エトキシル化ペンタエリスリトールテトラアクリレート、ペンタエリスリトールテトラアクリレート、カプロラクトン修飾ジペンタエリスリトールヘキサアクリレート等のテトラアクリロイル化合物、等が挙げられる。
アセチレンジオール、プロピンオール、ブチンオール、ペンチンオール、ヘキシンオール、ヘキシンジオール、ヘプチンオール、ヘプチンジオール、オクチンオール、オクチンジオール等のアルキニルアルコール類、および上記アルキニルアルコール類の一部または全部のOH基がNH2基に置換されたアルキニルアミン類などが挙げられる。
ジヒドロキシナフタレン、トリヒドロキシナフタレン、テトラヒドロキシナフタレン、ジヒドロキシベンゼン、ベンゼントリオール、ビフェニルテトラオール、ピロガロール、(ヒドロキシナフチル)ピロガロール、トリヒドロキシフェナントレン、ビスフェノールA、ビスフェノールF、キシリレングリコール、ジ(2-ヒドロキシエトキシ)ベンゼン、ビスフェノールA-ビス-(2-ヒドロキシエチルエーテル)、テトラブロムビスフェノールA、テトラブロムビスフェノールA-ビス-(2-ヒドロキシエチルエーテル)等の芳香族ポリオール;
ジブロモネオペンチルグリコール等のハロゲン化ポリオール;
エポキシ樹脂等の高分子ポリオールが挙げられる。本実施形態においては、これらから選択される少なくとも1種を組み合わせて用いることができる。
上記ポリオールとエチレンオキサイドやプロピレンオキサイドなどアルキレンオキサイドとの付加反応生成物;
アルキレンポリアミンとエチレンオキサイドや、プロピレンオキサイドなどアルキレンオキサイドとの付加反応生成物;さらには、
ビス-[4-(ヒドロキシエトキシ)フェニル]スルフィド、ビス-[4-(2-ヒドロキシプロポキシ)フェニル]スルフィド、ビス-[4-(2,3-ジヒドロキシプロポキシ)フェニル]スルフィド、ビス-[4-(4-ヒドロキシシクロヘキシロキシ)フェニル]スルフィド、ビス-[2-メチル-4-(ヒドロキシエトキシ)-6-ブチルフェニル]スルフィドおよびこれらの化合物に水酸基当たり平均3分子以下のエチレンオキシドおよび/またはプロピレンオキシドが付加された化合物;
ジ-(2-ヒドロキシエチル)スルフィド、1,2-ビス-(2-ヒドロキシエチルメルカプト)エタン、ビス(2-ヒドロキシエチル)ジスルフィド、1,4-ジチアン-2,5-ジオール、ビス(2,3-ジヒドロキシプロピル)スルフィド、テトラキス(4-ヒドロキシ-2-チアブチル)メタン、ビス(4-ヒドロキシフェニル)スルホン(ビスフェノールS)、テトラブロモビスフェノールS、テトラメチルビスフェノールS、4,4'-チオビス(6-tert-ブチル-3-メチルフェノール)、1,3-ビス(2-ヒドロキシエチルチオエチル)-シクロヘキサンなどの硫黄原子を含有したポリオール等が挙げられる。本実施形態においては、これらから選択される少なくとも1種を組み合わせて用いることができる。
1,2-ジメルカプトベンゼン、1,3-ジメルカプトベンゼン、1,4-ジメルカプトベンゼン、1,2-ビス(メルカプトメチル)ベンゼン、1,3-ビス(メルカプトメチル)ベンゼン、1,4-ビス(メルカプトメチル)ベンゼン、1,2-ビス(メルカプトエチル)ベンゼン、1,3-ビス(メルカプトエチル)ベンゼン、1,4-ビス(メルカプトエチル)ベンゼン、1,3,5-トリメルカプトベンゼン、1,3,5-トリス(メルカプトメチル)ベンゼン、1,3,5-トリス(メルカプトメチレンオキシ)ベンゼン、1,3,5-トリス(メルカプトエチレンオキシ)ベンゼン、2,5-トルエンジチオール、3,4-トルエンジチオール、1,5-ナフタレンジチオール、2,6-ナフタレンジチオール等の芳香族ポリチオール化合物;
2-メチルアミノ-4,6-ジチオール-sym-トリアジン、3,4-チオフェンジチオール、ビスムチオール、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-ジチエタン等の複素環ポリチオール化合物等が挙げられる。
ジエチルアミン、ジプロピルアミン、ジ-n-ブチルアミン、ジ-sec-ブチルアミン、ジイソブチルアミン、ジ-n-ペンチルアミン、ジ-3-ペンチルアミン、ジヘキシルアミン、ジオクチルアミン、ジ(2-エチルヘキシル)アミン、メチルヘキシルアミン、ジアリルアミン、N-メチルアリルアミン、ピペリジン、ピロリジン、ジフェニルアミン、N-メチルアミン、N-エチルアミン、ジベンジルアミン、N-メチルベンジルアミン、N-エチルベンジルアミン、ジシクロヘキシルアミン、N-メチルアニリン、N-エチルアニリン、ジナフチルアミン、1-メチルピペラジン、モルホリン等の単官能2級アミン化合物;
N,N'-ジメチルエチレンジアミン、N,N'-ジメチル-1,2-ジアミノプロパン、N,N'-ジメチル-1,3-ジアミノプロパン、N,N'-ジメチル-1,2-ジアミノブタン、N,N'-ジメチル-1,3-ジアミノブタン、N,N'-ジメチル-1,4-ジアミノブタン、N,N'-ジメチル-1,5-ジアミノペンタン、N,N'-ジメチル-1,6-ジアミノヘキサン、N,N'-ジメチル-1,7-ジアミノヘプタン、N,N'-ジエチルエチレンジアミン、N,N'-ジエチル-1,2-ジアミノプロパン、N,N'-ジエチル-1,3-ジアミノプロパン、N,N'-ジエチル-1,2-ジアミノブタン、N,N'-ジエチル-1,3-ジアミノブタン、N,N'-ジエチル-1,4-ジアミノブタン、N,N'-ジエチル-1,5-ジアミノペンタン、N,N'-ジエチル-1,6-ジアミノヘキサン、N,N'-ジエチル-1,7-ジアミノヘプタン、ピペラジン、2-メチルピペラジン、2,5-ジメチルピペラジン、2,6-ジメチルピペラジン、ホモピペラジン、1,1-ジ-(4-ピペリジル)メタン、1,2-ジ-(4-ピペリジル)エタン、1,3-ジ-(4-ピペリジル)プロパン、1,4-ジ-(4-ピペリジル)ブタン、テトラメチルグアニジン等の2級ポリアミン化合物;等が挙げられる。
上記の重合反応性化合物は1種または2種以上を混合して用いてもよい。
本発明の組成物には、上記重合反応性化合物以外の成分が含まれていてもよい。例えば、単官能のイソ(チオ)シアネート化合物、単官能の(チオ)エポキシ化合物、単官能のオキセタニル化合物、単官能のチエタニル化合物、メタクリロイルオキシ基、アクリロイルオキシ基、メタクリロイルチオ基、アクリロイルチオ基、メタクリルアミド基、またはアクリルアミド基から任意に選ばれた官能基を1個有する単官能の(メタ)アクリロイル化合物、メタクリロイルオキシ基、アクリロイルオキシ基、メタクリロイルチオ基、アクリロイルチオ基、メタクリルアミド基、またはアクリルアミド基以外の重合性炭素炭素2重結合を1個有する単官能のアルケン化合物、溶剤として使用されたアルコール以外の単官能のアルコール化合物、単官能のチオール化合物、アミノ基、第二アミノ基から任意に選ばれた1個の官能基有する単官能のアミン化合物、カルボキシル基を1個有する単官能のカルボン酸化合物、溶剤、および水分などが挙げられる。
イソブチリルパーオキサイド、o-クロロベンゾイルパーオキサイド、ベンゾイルパーオキサイド等のジアシルパーオキサイド化合物;
トリス(t-ブチルパーオキシ)トリアジン、t-ヌチルクミルパーオキサイド等のジアルキルパーオキサイド化合物;
1,1-ジ(t-ヘキシルパーオキシ)シクロヘキサン、2,2-ビス(4,4-ジ-t-ブチルパーオキシシクロヘキシル)プロパン、2,2-ジ(t-ブチルパーオキシ)ブタン等のパーオキシケタール化合物;
α-クミルパーオキシネオデカノエート、t-ブチルパーオキシピバレート、2,4,4-トリメチルペンニルパーオキシ-2-エチルヘキサノエート、t-ブチルパーオキシ-2-エチルヘキサノエート、t-ブチルパーオキシ-3,5,5-トリメチルヘキサノエート等のアルキルパーエステル化合物;
ジ-3-メトキシブチルパーオキシジカーボネート、ビス(4-t-ブチルシクロヘキシル)パーオキシジカーボネート、t-ブチルパーオキシイソプロピルカーボネート、ジエチレングリコールビス(t-ブチルパーオキシカーボネート)等のパーオキシカーボネート化合物等が挙げられる。
(a)ポリイソ(チオ)シアネート化合物とポリ(チ)オール化合物が重合したポリ(チオ)ウレタン樹脂
本願においてポリ(チオ)ウレタン樹脂とは、ポリウレタン樹脂、ポリチオウレタン樹脂およびポリジチオウレタン樹脂を意味する。
(b)ポリ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と、ポリアミン化合物が重合したポリ(チオ)ウレア樹脂
本願においてポリ(チオ)ウレア樹脂とは、ポリウレア樹脂およびポリチオウレア樹脂を意味する。
(c)ポリ(チオ)エポキシ化合物が重合したポリ(チオ)エポキシ樹脂
(d)ポリ(チオ)エポキシ化合物とポリ(チ)オール化合物が重合したポリ(チオ)エポキシ-ポリ(チ)オール樹脂
(e)ポリ(チオ)エポキシ化合物とポリアミン化合物が重合したポリ(チオ)エポキシ-ポリアミン樹脂
(f)ポリ(チオ)エポキシ化合物と酸無水物が重合したポリ(チオ)エポキシ-酸無水物樹脂
(g)ポリ(メタ)アクリロイル化合物が重合したポリ(メタ)アクリロイル樹脂
(h)ポリ(メタ)アクリロイル化合物とポリ(チ)オール化合物が重合したポリ(メタ)アクロイル-ポリ(チ)オール樹脂
(i)ポリ(メタ)アクリロイル化合物とポリアルケン化合物が重合したポリ(メタ)アクリル-ポリアルケン樹脂
(j)ポリ(メタ)アクリロイル化合物とアルキン化合物が重合したポリ(メタ)アクリル-ポリアルキン樹脂
(k)ポリ(メタ)アクリロイル化合物とポリアミン化合物が重合したポリ(メタ)アクリル-ポリアミン樹脂
(l)ポリアルケン化合物が重合したポリアルケン樹脂
(m)ポリアルケン化合物とポリ(チ)オール化合物が重合したポリアルケン-ポリ(チ)オール樹脂
(n)ポリアルケン化合物とポリアミン化合物が重合したポリアルケン-ポリアミン樹脂
(o)アルキン化合物が重合したポリアルキン樹脂
(p)アルキン化合物とポリ(チ)オール化合物が重合したポリアルキン-ポリ(チ)オール樹脂
(q)アルキン化合物とポリアミン化合物が重合したポリアルキン-ポリアミン樹脂
(r)アルキン化合物とポリアルケン化合物が重合したポリアルキン-ポリアルケン樹脂
(s)ポリオキセタニル化合物が重合したポリオキセタニル樹脂
(t)ポリオキセタニル化合物とポリ(チ)オール化合物が重合したポリオキセタニル-ポリ(チ)オール樹脂
(u)ポリオキセタニル化合物とポリアミン化合物が重合したポリオキセタニル-ポリアミン樹脂
(v)ポリオキセタニル化合物と酸無水物が重合したポリオキセタニル-酸無水物樹脂
(w)ポリチエタニル化合物とポリ(チ)オール化合物が重合したポリチエタニル-ポリ(チ)オール樹脂
(x)ポリチエタニル化合物とポリアミン化合物が重合したポリチエタニル-ポリアミン樹脂
(y)ポリチエタニル化合物と酸無水物が重合したポリチエタニル-酸無水物樹脂
(z)(a)~(y)から選ばれた2種以上が共重合した混合樹脂
本発明においては、重合時のモールドを変えることにより種々の形状の成形体を得ることができる。本発明の成形体は、所望の形状とし、必要に応じて形成されるコート層や他の部材等を備えることにより、様々な光学材料として用いることができる。
光学材料としては、プラスチックレンズ、発光ダイオード(LED)、プリズム、光ファイバー、情報記録基板、フィルター、発光ダイオード等を挙げることができる。特に、プラスチックレンズとして好適である。
以下、本発明の成形体からなるプラスチックレンズについて説明する。プラスチックレンズは以下のように製造することができる。
本発明のプラスチックレンズは、通常、上述の組成物を用いた注型重合法によって製造される。
具体的には、まず、一般式(1)のリン酸ジエステル化合物Aを少なくとも1種含む内部離型剤を、重合反応性化合物を含む組成物に添加し、混合撹拌し、必要に応じて減圧脱泡を行う。
ポリエステル系ポリウレタンエマルジョンコート剤、ポリ塩化ビニルエマルジョンコート剤、レタンアクリルエマルジョンコート剤、シリコンアクリルエマルジョンコート剤、酢酸ビニルアクリルエマルジョンコート剤、アクリルエマルジョンコート剤;
スチレン-ブタジエン共重合体ラテックスコート剤、アクリルニトリル-ブタジエン共重合体ラテックスコート剤、メチルメタクリレート-ブタジエン共重合体ラテックスコート剤、クロロプレンラテックスコート剤、ポリブタジエンラテックスのゴム系ラテックスコート剤、ポリアクリル酸エステルラテックスコート剤、ポリ塩化ビニリデンラテックスコート剤、ポリブタジエンラテックスコート剤、あるいはこれらラテックスコート剤に含まれる樹脂のカルボン酸変性物ラテックスもしくはディスパージョンからなるコート剤が好ましい。
島津製作所社製デジタル精密屈折計KPR-30Vを用い、20℃で測定した。
<耐熱性(Tg)>
熱機械分析装置TMA-60/60Hを用い、TMAペネートレーション法(50g荷重、ピン先0.5mmφ、昇温速度10℃/min)でのガラス転移温度Tgを測定した。
室温で成形体からモールドを剥離する際の離型性を以下の基準に従い評価した。
◎ 非常に良好
室温まで冷却された時点で、既にモールドと成形体との密着面の全面が自然に剥離する。
○:良好
室温まで冷却された時点で、既にモールドと成形体との密着面の一部が自然に剥離しており、離型操作(得られた成形体と成型モールドの密着面へ、クサビ型の離型治具を入れ込み、成形体をモールドから剥がす。)で容易に剥離する。
△:やや不良
室温まで冷却されてもモールドと成形体が密着しており、離型操作(得られた成形体と成型モールドの接面へ、クサビ型の離型治具を入れ込み、成形体をモールドから剥がす。)でようやく剥離することができる。レンズまたはモールドが欠損している場合がある。
×:悪い
室温まで冷却し、その後離型操作(得られた成形体と成型モールドの密着面へ、クサビ型の離型治具を入れ込み、成形体をモールドから剥がす。)を行っても、モールドと成形体とが密着している。
キャビン工業社製 CS-15MT ハロゲンランプ出力300W の光を試料(硬化樹脂およびプラスチックレンズ)に照射して、目視により評価を行った。
○: 良好(濁り無)
△: やや不良(微濁)
×: 不良(明らかに濁り有)
以下の公知の方法にて下記リン酸ジエステル(110)を含むリン酸エステル(110A)を得た。
オキシ塩化リン27.0g(和光純薬社製)をテトラヒドロフラン30gに溶解し、0℃に冷却した。この溶液にトリ(プロピレングリコール)n-ブチルエーテル異性体混合物(ダウ社製DOWANOL TPnB)43.7g、トリエチルアミン17.8g及びテトラヒドロフラン20gの混合溶液を30分で滴下した。滴下時、反応溶液の温度は5~10℃であった。滴下終了後35℃で2時間熟成させた。その後更にこの反応溶液を0℃に冷却し、1-ドデカノール(和光純薬社製)32.8g、トリエチルアミン17.8g及びテトラヒドロフラン20gの溶液を30分間かけて滴下した。滴下時、反応溶液の温度は5~10℃であった。滴下終了後、温度を徐々にあげ、20℃で更に10時間熟成させた。反応終了後、反応溶液を0℃に冷却し、水酸化ナトリウム28.2gをイオン交換水40gに溶解した溶液を30分かけて滴下し、0℃で2時間撹拌した。反応溶液に3N塩酸300mLを加え反応液を酸性とした後に、生成したリン酸エステルをジエチルエーテル200gで抽出した。有機層を分取し、さらにイオン交換水(100mL×4)で洗浄した。有機層を分取した後、溶媒を減圧留去し、リン酸エステル(110A)85.5gを得た(1-ドデカノールリン酸モノエステル:下記式(110)で表されるリン酸ジエステル(110)=16:84)。リン酸ジエステル(110)の同定データを図1(1H-NMRスペクトルチャート)及び図2(IRスペクトルチャート)に示す。
以下の公知の方法にて下記リン酸ジエステル(100)を得た。
調製例1において、原料のトリ(プロピレングリコール)n-ブチルエーテル異性体混合物と1-ドデカノールを、それぞれ後述の式(300)で表されるアルコール(300)とトリデカノールに変更し、合成を行うことにより、下記式(100)で表されるリン酸ジエステル(100)を得た。得られたリン酸ジエステル(100)の同定データを図3(1H-NMRスペクトルチャート)、図4(エレクトロスプレー質量分析チャート)および図5(IRスペクトルチャート)に示す。
特開平04-134088号に従い、下記式(120)で表されるリン酸ジエステル(120)を製造した。すなわち、モノトリオキシエチレンラウリルリン酸100gと水酸化カリウム66.6g、イオン交換水157.0gを混合し、70℃に昇温し溶解した。この溶液にジエチル硫酸117.0gを8時間かけて滴下した。滴下終了後、70℃で4時間熟成した。この反応混合物を塩酸酸性とした後、エーテル250mLで3回抽出した。エーテルを減圧留去して得られた残渣をエタノールから再結晶し、リン酸ジエステル(120)を得た。
US3666843 Aに従い、下記式(130)で表されるリン酸ジエステル(130)を製造した。すなわち、イソオクチルフェニルノナオキシエチレングリコール300gと、メタリン酸エチル54gを反応容器に入れ、70℃で3.5時間撹拌し、リン酸ジエステル(130)を得た。
内部離型剤として、上記式(100)で表されるリン酸ジエステル(100) 0.01重量部(500ppm)、UV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 0.3重量部(15,000ppm)、触媒としてジメチル錫(II)ジクロリド 0.01重量部(500ppm)、重合反応性化合物としてトリレンジイソシアネート 6.14重量部とヘキサメチレンジイソシアネート 3.19重量部を20℃で撹拌混合し均一溶液を得た。この均一溶液に、さらに重合反応性化合物として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の混合物 10.67重量部を加えて20℃にて撹拌混合し、重合性の組成物を得た。この重合性の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これを重合オーブンに入れ、25℃から130℃まで19時間かけて徐々に昇温した後130℃で2時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。剥離は非常に容易で、それにより成形体(プラスチックレンズ)の破断およびガラスモールドの破損等の不具合もなく、成形体(プラスチックレンズ)は無色透明で屈折率ne1.67、アッベ数νe28、Tg116℃であった。離型性および透明性を確認した。結果を表1に示す。
上記式(100)で表されるリン酸ジエステル(100)の添加量を表1に記載のように変更して、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表1に示す。
リン酸ジエステル(100)を、上記式(110)で表されるリン酸ジエステル(110)を含むリン酸エステル(110A)に変更し、添加量を1000ppmとして、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表2に示す。
リン酸ジエステル(100)を、上記式(120)で表されるリン酸ジエステル(120)に変更し、添加量を1000ppmとして、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表2に示す。
リン酸ジエステル(100)を、上記式(130)で表されるリン酸ジエステル(130)に変更し、添加量を1000ppmとして、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表2に示す。
以下の公知の方法にて内部離型剤Aを得た。
まず、調製例1において、原料のトリ(プロピレングリコール)n-ブチルエーテル異性体混合物を加える工程を省き、1-ドデカノールを加える工程において、1-ドデカノールの代わりに下記式(300)で表されるアルコール(300)を加え、合成を行うことにより、下記式(200)で表されるリン酸モノエステル(200)を得た。
調製例2で得たリン酸ジエステル(100)16重量部、及び上記のリン酸モノエステル(200)16重量部、下記式(300)で表されるアルコール(300)68重量部を混合することによって、内部離型剤Aを得た。
リン酸ジエステル(100)を、上記の内部離型剤Aに変更し、且つ内部離型剤Aの添加量を表3に記載のように変更して、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表3に示す。
内部離型剤Aを、下記の組成比で化合物を含む内部離型剤B、C、Dに変更して、実施例6と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表3に示す。
なお、内部離型剤Bは、特開2000-281687号の記載に基づいて合成されたものであり、内部離型剤Cは城北化学工業株式会社製 JP-506H、内部離型剤DはStepan社製 ZelecUNである。
リン酸ジエステル(100)を、内部離型剤A(1000ppm)及び内部離型剤D(500ppm)に変更した以外は、実施例1と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表3に示す。
室温にて、調製例5で得られた内部離型剤Aを28重量%ナトリウムメトキシドで中和(PH7.3)し、混入したメタノールを減圧除去することにより、下記の組成比で化合物を含む内部離型剤A-Naを得た。
内部離型剤Aに代えて、内部離型剤A-Naを用いた以外は、実施例6と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表4に示す。
内部離型剤Aに代えて、下記の組成比で化合物を含む内部離型剤A-Amineを用いた以外は、実施例6と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表4に示す。
室温にて、比較例1で用いた内部離型剤Bを28重量%ナトリウムメトキシドで中和(PH7.5)し、混入したメタノールを減圧除去することにより、下記の組成比で化合物を含む内部離型剤B-Naを得た。
内部離型剤Aに代えて、内部離型剤B-Naを用いた以外は、実施例6と同様に成形体(プラスチックレンズ)を調製し、離型性および透明性を確認した。結果を表4に示す。
100mlサンプル瓶に、内部離型剤Aの添加量を0~0.1重量部(0~5,000ppm)の範囲で変化させて加え、次いでUV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 0.3重量部(15,000ppm)、触媒としてジブチル錫(II)ジクロリド 0.01重量部(500ppm)、重合反応性化合物として2,5(6)-ビス(イソシアナトメチル)ビシクロ-[2.2.1]-ヘプタン10.12重量部を添加し20℃で撹拌混合し均一溶液を計7種得た。これら7種の均一溶液に、さらに重合反応性化合物として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) 4.78重量部、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5.1重量部を加えて20℃にて撹拌混合し、計7種の均一な組成物を得た。これらの組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、25℃から120℃まで19時間かけて徐々に昇温した後120℃で2時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.60、アッベ数νe40、Tg114℃であった。離型性および透明性の評価結果を表5に示す。
100mlサンプル瓶に、内部離型剤Aの添加量を0~0.1重量部(0~5,000ppm)の範囲で変化させて加え、次いでUV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 0.3重量部(15,000ppm)、触媒としてジブチル錫(II)ジクロリド 0.01重量部(500ppm)、重合反応性化合物としてm-キシリレンジイソシアネート10.12重量部を20℃で撹拌混合し均一溶液を計7種得た。これら7種の均一溶液に、さらに重合反応性化合物として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の混合物9.88重量部を加えて20℃にて撹拌混合し、計7種の均一な組成物を得た。これら7種の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、25℃から120℃まで19時間かけて徐々に昇温した後120℃で2時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.67、アッベ数νe31、Tg98℃ であった。離型性および透明性の評価結果を表5に示す。
7個の100mlサンプル瓶に、触媒としてN,N-ジメチルシクロヘキシルアミン 0.004重量部、N,N-ジシクロヘキシルメチルアミン 0.018重量部、重合反応性化合物として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の混合物1.83重量部をそれぞれ加え、20℃で撹拌混合して均一溶液(1)を得た。別の100mlサンプル瓶7個に内部離型剤Aを0~0.1重量部(0~5,000ppm)の範囲で添加量を表5のように変えて添加し、次いでUV吸収剤として2-(2-ヒドロキシ-5-t-ブチルフェニル)-2H-ベンゾトリアゾール(BASF社製 商品名Tinuvin PS) 0.2重量部(10,000ppm)、重合反応性化合物としてビス(2,3-エピチオプロピル)ジスルフィド18.17重量部を加えた後、20℃で撹拌混合し均一溶液(2)を7種得た。これら7種の均一溶液(2)に、均一溶液(1)を加えて20℃で攪拌し重合性の組成物を得た。この7種の重合性の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、30℃から80℃まで19時間かけて徐々に昇温した後80℃で2時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.74、アッベ数νe32、Tg78℃ であった。離型性および透明性の評価結果を表5に示す。
7個の100mlサンプル瓶に、内部離型剤Aの添加量を0~0.1重量部(0~5,000ppm)の範囲で表5のように変えて添加し、次いで、触媒としてテトラブチルホスホニウムブロミド 0.3重量部(15,000ppm)、重合反応性化合物として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の混合物 7.0重量部を40℃で撹拌混合し均一溶液を7種得た。これらの均一溶液に、さらにUV吸収剤としてBASF社製 商品名Tinuvin384-2 0.2重量部(10,000ppm)、重合反応性化合物としてビスフェノールAジグリシジルエーテル13.0重量部を40℃で撹拌混合し均一な重合性の組成物を7種得た。これら重合性の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、70℃から120℃まで9時間かけて徐々に昇温した後120℃で6時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.64、アッベ数νe35、Tg64℃ であった。離型性および透明性の評価結果を表5に示す。
100mlサンプル瓶に、内部離型剤Aの添加量を0~0.1重量部(0~5,000ppm)の範囲で表5のように変化させて加え、次いでUV吸収剤として2-ヒドロキシ-4-メチルベンゾフェノン 0.01重量部(500ppm)、重合開始剤として、1,1-ジ(t-ヘキシルパーオキシ)シクロヘキサン 0.6重量部(30,000ppm)、重合反応性化合物としてジエチレングリコールビス(アリルカーボネート)20.0重量部を20℃で撹拌混合し重合性の組成物を7種得た。この7種の重合性の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、75℃から130℃まで20時間かけて徐々に昇温した後130℃で3時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.50、アッベ数νe58であった。離型性および透明性の評価結果を表5に示す。
100mlサンプル瓶に、内部離型剤Aの添加量を0~0.1重量部(0~5,000ppm)の範囲で表5のように変化させて加え、次いでUV吸収剤として2-ヒドロキシ-4-メチルベンゾフェノン 0.01重量部(500ppm)、重合開始剤として、1,1-ジ(t-ヘキシルパーオキシ)シクロヘキサン 0.6重量部(30,000ppm)、重合反応性化合物としてジビニルベンゼン 5.0重量部、エトキシビスフェノールAジアクリレート(NKエステルA-BPE-10(新中村化学工業株式会社製)) 15.0重量部を20℃で撹拌混合し均一な重合性の組成物を7種得た。これらの重合性の組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、75℃から130℃まで20時間かけて徐々に昇温した後130℃で3時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.56、アッベ数νe38であった。離型性および透明性の評価結果を表5に示す。
100mlサンプル瓶に、内部離型剤A 0.02重量部(1,000ppm)、UV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 0.3重量部(15,000ppm)、触媒としてジメチル錫(II)ジクロリド 0.008重量部(400ppm)、重合反応性化合物として2,5(6)-ビス(イソシアナトメチル)ビシクロ-[2.2.1]-ヘプタン5.84重量部、ヘキサメチレンジイソシアネート3.89重量部を添加し20℃で撹拌混合し均一溶液を得た。さらに重合反応性化合物として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) 4.70重量部、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5.57重量部を加えて20℃にて撹拌混合し、均一な組成物を得た。これらの組成物を0.13kPaの減圧下にて30分間脱泡を行った後、1μmPTFE製フィルターでろ過を行い、ガラスモールドとテープからなるキャビティー(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)に注入しテープで密封した。これらを重合オーブンに入れ、25℃から120℃まで15時間かけて徐々に昇温した後120℃で4時間保持して重合した。冷却後、ガラスモールドとテープを剥離して、内部に形成された硬化樹脂からなる成形体(プラスチックレンズ)を取り出した。得られた成形体(プラスチックレンズ)は無色透明で屈折率ne1.60、アッベ数νe39、Tg92℃ であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 0.10重量部、viosorb583(紫外線吸収剤:登録商標、共同薬品株式会社製)1.5重量部、N-ベンジル-2-メチルイミダゾール0.028重量部、および1,5-ペンタメチレンジイソシアネート23.9重量部を混合し、室温で15分間攪拌溶解させた後、1,5-ペンタメチレンジイソシアネート変性体組成物27.9重量部を混合してポリイソシアネート液を調製した。このポリイソシアネート液のイソシアヌレート1核体濃度は35%であった。これに4,8および4,7および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29.1重量部、および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)19.1重量部を加えて室温で撹拌混合させモノマー混合物の均一溶液を得た。この均一溶液の粘度は40mPa・sであった。この均一溶液を、室温、減圧下にて30分間脱泡し、1μmテフロン(登録商標)フィルターにてろ過を行った後、ガラスモールドとテープからなるモールド型(カーブ形状:凹凸面共に4カーブ、中心厚:2mm)へ注入した。これをオーブンへ投入し、25℃~120℃までおよそ24時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出し、離型した後、さらに120℃で2時間アニールを行い樹脂成形体を得た。樹脂成形体は、無色透明な外観を有し、屈折率(ne)1.60、アッベ数(νe)39、耐熱性89℃であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 0.1重量部(1,000ppm)、UV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 1.5重量部(15,000ppm)、ビス(4-イソシアナトシクロへキシル)メタン58.9重量部を20℃で撹拌混合し、均一溶液を得た。この均一溶液に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の混合物 41.1重量部、ジブチル錫(II)ジクロリド0.15重量部(1,500ppm)を加えて20℃にて撹拌混合し、混合液を得た。この混合液を600Paにて1時間脱泡を行い、1μmPTFEフィルターにて濾過を行った後、中心厚2mm、直径80mmの4Cのプラノー用ガラスモールドに注入した。このモールド型を重合オーブンへ投入、20℃~130℃まで21時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出した。得られたプラノーレンズをさらに130℃で2時間アニール処理を行った。得られた2mm厚のプラノーレンズは透明性があり、屈折率(ne)1.60、アッベ数(νe)39、耐熱性136℃であり、光学材料用透明樹脂として好適であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 0.10重量部及びジメチルスズジクロライド0.20重量部 (本荘ケミカル株式会社製、商品名 ネスチンP)、2-(2-ヒドロキシ-5-tert-オクチルフェニル)-2H-ベンゾトリアゾール1.50重量部 (堺化学工業株式会社製、商品名Viosorb583)、イソホロンジイソシアネート53.0重量部を撹拌混合した。その後、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の混合物47.0重量部を混合し組成物を調製した。得られた重合原料を1.0μmのテフロン(登録商標)フィルターによりろ過し、400Pa以下の真空下で60分間脱気した。脱気した組成物を中心厚2mm、直径80mmの4Cのプラノー用ガラス型とテープからなるモールド型に注入した。その後25℃~120℃の加熱炉中で20時間重合を行い、冷却後、ガラス型とテープを除去し、チオウレタン成形体を得た。更に130℃で2時間アニールを行った。得られた2mm厚のプラノーレンズは透明性があり、屈折率(ne)1.60、アッベ数(νe)38、耐熱性130℃であり、光学材料用透明樹脂として好適であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 0.10重量部及びジブチル錫(II)ジクロリド0.17重量部、2-(2-ヒドロキシ-5-tert-オクチルフェニル)-2H-ベンゾトリアゾール1.50重量部 (堺化学工業株式会社製、商品名Viosorb583)、イソホロンジイソシアネート23.2重量部、ヘキサメチレンジイソシアネート19.8重量部を撹拌混合した。その後、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)57.0重量部を混合し組成物を調製した。得られた重合原料を1.0μmのテフロン(登録商標)フィルターによりろ過し、400Pa以下の真空下で60分間脱気した。脱気した組成物を中心厚2mm、直径80mmの4Cのプラノー用ガラス型とテープからなるモールド型に注入した。その後35℃~130℃の加熱炉中で21時間重合を行い、冷却後、ガラス型とテープを除去し、チオウレタン成形体を得た。更に130℃で2時間アニールを行った。得られた2mm厚のプラノーレンズは透明性があり、屈折率(ne)1.56、アッベ数(νe)41、耐熱性82℃であり、光学材料用透明樹脂として好適であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 0.1重量部(1,000ppm)、UV吸収剤として2-(2'-ヒドロキシ-5'-t-オクチルフェニル)ベンゾトリアゾール(共同薬品社製 商品名バイオソーブ583) 2.0重量部(20,000ppm)、ビス(4-イソシアナトシクロへキシル)メタン27.6重量部、イソホロンジイソシアネート27.6重量部を20℃で撹拌混合し、均一溶液を得た。この均一溶液に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の混合物44.8重量部、ジメチル錫(II)ジクロリド0.17重量部(1,700ppm)を加えて20℃にて撹拌混合し、混合液を得た。この混合液を600Paにて1時間脱泡を行い、1μmPTFEフィルターにて濾過を行った後、中心厚2mm、直径80mmの4Cのプラノー用ガラスモールドに注入した。このモールド型を重合オーブンへ投入、20℃~130℃まで21時間かけて徐々に昇温して重合した。重合終了後、オーブンからモールド型を取り出した。得られたプラノーレンズをさらに130℃で2時間アニール処理を行った。得られた2mm厚のプラノーレンズは透明性があり、屈折率(ne)1.60、アッベ数(νe)38、耐熱性117℃であり、光学材料用透明樹脂として好適であった。離型性および透明性の評価結果を表6に示す。
内部離型剤A 1.0重量部(10,000ppm)及びトリメチロールプロパンのプロピレンオキサイド付加体(Bayer社製;Desmophen 4011T)58.8重量部、TINUVIN292(BASF社製;光安定剤)0.40重量部(4,000ppm)を混合溶解し、均一溶液とした。2,4-トリレンジイソシアネートと2,6-トリレンジイソシアネートの混合物41.2重量部に、ベンゾトリアゾール系化合物(共同薬品社製;バイオソーブ583(2-(2'-ヒドロキシ-5'-tert-オクチルフェニル)ベンゾトリアゾール))1.50重量部(15,000ppm)を混合溶解し、均一溶液とした。それぞれの溶液を20℃で混合して、400Paにて脱泡を行った後に直径80mmの4Cのプラノー用成型モールドへ注入した。これを重合オーブンへ投入して、15℃~120℃まで24時間かけて徐々に昇温して重合した。重合終了後、オーブンから取り出して成型モールドからの離型作業を行った。離型性は良好であり、モールドの剥離は見られなかった。得られた成形体をさらに120℃で2時間アニール処理を行った。得られた成形体は透明性があり、脈理は認められず、屈折率(ne)1.54、Tgは81℃であり、光学材料用途として好適であった。離型性および透明性の評価結果を表6に示す。
Claims (10)
- 重合反応性化合物と、請求項1に記載の前記内部離型剤を含む、組成物。
- 前記重合反応性化合物に対する一般式(1)で表される前記リン酸ジエステル化合物の量が、1×10-1~5×104ppmの範囲である、請求項2に記載の組成物。
- 前記重合反応性化合物が、ポリイソ(チオ)シアネート化合物、ポリ(チオ)エポキシ化合物、ポリオキセタニル化合物、ポリチエタニル化合物、ポリ(メタ)アクリロイル化合物、ポリアルケン化合物、アルキン化合物、ポリ(チ)オール化合物、ポリアミン化合物、酸無水物、またはポリカルボン酸化合物から選択される1種または2種以上である、請求項2または3に記載の組成物。
- 請求項2~4のいずれかに記載の組成物を重合した成形体。
- 請求項5に記載の成形体からなる、光学材料。
- 請求項5に記載の成形体からなる、プラスチックレンズ。
- 請求項2~4のいずれかに記載の組成物を注型重合する工程を含む、プラスチックレンズの製造方法。
- 請求項8に記載の製造方法で得られたプラスチックレンズ。
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KR102647150B1 (ko) * | 2019-01-31 | 2024-03-14 | 다이킨 고교 가부시키가이샤 | 이형제 |
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