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US 8,012,596 B2Granted
Photochromic lens substrate
AssigneeTokuyama Corporation
InventorsJunji Takenaka, Hironobu Nagoh, Junji Momoda
Life of this patent
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Abstract
A polymerization curable composition comprising a specific polyfunctional polymerizable monomer having a hard molecular structure with an L-scale Rockwell hardness of its homopolymer of 60 or more, a specific polyfunctional polymerizable monomer and a photochromic compound, a photochromic lens substrate composed of a cured product of the polymerization curable composition, and a lens comprising the photochromic lens substrate. The substrate and lens show excellent photochromic properties such as high color development density and high fading rate, and the cured product has excellent substrate properties such as hardness, heat resistance and impact resistance as well as strength (toughness) that allows for its use in rimless spectacles.
Claims8
A photochromic lens substrate, which comprises a cured product of a polymerization curable composition comprising:
- (I) a polyfunctional polymerizable monomer represented by the following formula (1):
- wherein R1 is a hydrogen atom or methyl group, the group —R2— is —CH2CH2O—, —CH2CH(CH3)O— or —C(═O)CH2CH2CH2CH2CH2O—, R3 is a trivalent to hexafunctional organic residue, a is an integer of 0 to 3 and b is an integer of 3 to 6;
- (II) a bifunctional polymerizable monomer represented by the following formula (2):
- wherein R4 and R5 are each independently a hydrogen atom or methyl group, R6 and R7 are each independently a hydrogen atom or alkyl group having 1 or 2 carbon atoms, the group —X— is —O—, —S—, —S(═O)2—, —C(═O)—O—, —CH2—, —CH═CH— or —C(CH3)2—, and m and n satisfy (m+n)=0 to 30;
- and
- (III) another polymerizable monomer different than the above polymerizable monomers (I) and (II), selected from the group consisting of polyethylene glycol methacrylate having an average molecular weight of 526, polyethylene glycol methacrylate having an average molecular weight of 360, methyl ether polyethylene glycol methacrylate having an average molecular weight of 475, methyl ether polyethylene glycol methacrylate having an average molecular weight of 1,000, polypropylene glycol methacrylate having an average molecular weight of 375, polypropylene glycol methacrylate having an average molecular weight of 430, stearyl methacrylate, lauryl methacrylate, ethylene glycol glycidyl ether, propylene glycol glycidyl ether, tetraethylene glycol diacrylate, nonaethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, nonaethylene glycol dimethacrylate, nonapropylene glycol dimethacrylate, ethylene glycol bisglycidyl methacrylate, 1, 4-butylene glycol dimethacrylate, 1, 9-nonylene glycol dimethacrylate, neopentylene glycol dimethacrylate, polyallyl compounds, acrylate and methacrylate compounds, vinyl compounds, bifunctional to hexafunctional polymerizable polyurethane oligomers and bifunctional to hexafunctional polymerizable polyester oligomers;
- (IV) a photochromic compound;
- and
- (V) a thermal polymerization initiator,
- wherein the amounts of the polyfunctional polymerizable monomer (I), the bifunctional polymerizable monomer (II) and the other polymerizable monomer (III) are 1 to 15 wt %, 10 to 80 wt % and 5 to 89 wt % based on the total of all the polymerizable monomers, respectively, the fading half-life period of the photochromic compound (IV) in the cured product is 30 times or less shorter than the fading half-life period of the photochromic compound (IV) in the polymerization curable composition, and said cured product has a tensile strength of 20 Kgf or more.
7 more elements
A polymerization curable composition for a photochromic lens substrate, the polymerization curable composition comprising:
- (I) a polyfunctional polymerizable monomer represented by the following formula (1):
- wherein R1 is a hydrogen atom or methyl group, the group —R2— is —CH2CH2O—, —CH2CH(CH3)O— or —C(═O)CH2CH2CH2CH2CH2O—, R3 is a trivalent to hexafunctional organic residue, a is an integer of 0 to 3 and b is an integer of 3 to 6;
- (II) a bifunctional polymerizable monomer represented by the following formula (2):
- wherein R4 and R5 are each independently a hydrogen atom or methyl group, R6 and R7 are each independently a hydrogen atom or alkyl group having 1 or 2 carbon atoms, the group —X— is —O—, —S—, —S(═O)2—, —C(═O)—O—, —CH2—, —CH═CH— or —C(CH3)2—, and m and n satisfy (m+n)=0 to 30;
- (III) another polymerizable monomer different from the above polymerizable monomers (I) and (II), selected from the group consisting of polyethylene glycol methacrylate having an average molecular weight of 526, polyethylene glycol methacrylate having an average molecular weight of 360, methyl ether polyethylene glycol methacrylate having an average molecular weight of 475, methyl ether polyethylene glycol methacrylate having an average molecular weight of 1,000, polypropylene glycol methacrylate having an average molecular weight of 375, polypropylene glycol methacrylate having an average molecular weight of 430, stearyl methacrylate, lauryl methacrylate, ethylene glycol glycidyl ether, propylene glycol glycidyl ether, tetraethylene glycol diacrylate, nonaethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, nonaethylene glycol dimethacrylate, nonapropylene glycol dimethacrylate, ethylene glycol bisglycidyl methacrylate, 1, 4-butylene glycol dimethacrylate, 1, 9-nonylene glycol dimethacrylate, neopentylene glycol dimethacrylate, polyallyl compounds, acrylate and methacrylate compounds, vinyl compounds, bifunctional to hexafunctional polymerizable polyurethane oligomers and bifunctional to hexafunctional polymerizable polyester oligomers;
- (IV) a photochromic compound;
- and
- (V) a thermopolymerization initiator,
- wherein the amounts of the polyfunctional polymerizable monomer (I), the bifunctional polymerizable monomer (II) and the other polymerizable monomer (III) are 1 to 15 wt %, 10 to 80 wt % and 5 to 89 wt % based on the total of all the polymerizable monomers, respectively, the fading half-life period of the photochromic compound (IV) in the cured product is 30 times or less shorter than the fading half-life period of the photochromic compound (IV) in the polymerization curable composition, and a cured product of said polymerization curable composition has a tensile strength of 20 Kgf or more.
6 more elements
A polymerization curable composition for a photochromic lens substrate, the polymerization curable composition comprising:
- (I) a polyfunctional polymerizable monomer represented by the following formula (1):
- wherein R1 is a hydrogen atom or methyl group, the group —R2— is —CH2CH2O—, —CH2CH(CH3)O— or —C(═O)CH2CH2CH2CH2CH2O—, R3 is a trivalent to hexafunctional organic residue, a is an integer of 0 to 3 and b is an integer of 3 to 6;
- (II) a bifunctional polymerizable monomer represented by the following formula (2):
- wherein R4 and R5 are each independently a hydrogen atom or methyl group, R6 and R7 are each independently a hydrogen atom or alkyl group having 1 or 2 carbon atoms, the group —X— is —O—, —S—, —S(═O)2—, —C(═O)—O—, —CH2—, —CH═CH—or —C(CH3)2—, and m and n satisfy (m+n)=0 to 30;
- (III) another polymerizable monomer different from the above polymerizable monomers (I) and (II), selected from the group consisting of polyethylene glycol methacrylate having an average molecular weight of 526, polyethylene glycol methacrylate having an average molecular weight of 360, methyl ether polyethylene glycol methacrylate having an average molecular weight of 475, methyl ether polyethylene glycol methacrylate having an average molecular weight of 1,000, polypropylene glycol methacrylate having an average molecular weight of 375, polypropylene glycol methacrylate having an average molecular weight of 430, stearyl methacrylate, lauryl methacrylate, ethylene glycol glycidyl ether, propylene glycol glycidyl ether, tetraethylene glycol diacrylate, nonaethylene glycol diacrylate, diethylene glycol dimethacrylate, triethylene glycol dimethacrylate, tetraethylene glycol dimethacrylate, tripropylene glycol dimethacrylate, tetrapropylene glycol dimethacrylate, nonaethylene glycol dimethacrylate, nonapropylene glycol dimethacrylate, ethylene glycol bisglycidyl methacrylate, 1, 4-butylene glycol dimethacrylate, 1, 9-nonylene glycol dimethacrylate, neopentylene glycol dimethacrylate, polyallyl compounds, acrylate and methacrylate compounds, vinyl compounds, bifunctional to hexafunctional polymerizable polyurethane oligomers and bifunctional to hexafunctional polymerizable polyester oligomers;
- (IV) a photochromic compound;
- and
- (V) a thermopolymerization initiator,
- wherein:
- the amounts of the polyfunctional polymerizable monomer (I), the bifunctional polymerizable monomer (II) and the other polymerizable monomer (III) are 1 to 15 wt %, 10 to 80 wt % and 5 to 89 wt % based on the total of all the polymerizable monomers, respectively;
- the fading half-life period of the photochromic compound (IV) in the cured product is 30 times or less shorter than the fading half-life period of the photochromic compound (IV) in the polymerization curable composition;
- a cured product of said polymerization curable composition has a tensile strength of 20 Kgf or more;
- and
- the polyfunctional polymerizable monomer represented by formula (1) is at least one selected from the group consisting of caprolactam modified ditrimethylolpropane tetraacrylate, caprolactam modified ditrimethylolpropane tetramethacrylate and caprolactam modified dipentaerythritol hexaacrylate.
11 more elements
Dependencies are inferred from the claim text.