Polythiourethane-based polymerizable composition and optical resin obtained from the same

A technology of polymeric composition and polythiol compound, which is applied in the field of resin and optical components, and polymeric composition, and can solve problems such as cracks in the coating film and poor dyeability

Active Publication Date: 2008-07-23
MITSUI CHEM INC
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

[0009] Usually, there is a trade-off relationship between dyeability and the heat resistance of the base material, and when the heat resistance is too high, the dyeability deteriorates
In addition, when the heat resistance is lowered in order to improve the dyeability, the difference in heat resistance between the above-mentioned hard coat film, anti-reflection coating film, and lens substrate causes cracks to occur on the coating film during use.

Method used

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  • Polythiourethane-based polymerizable composition and optical resin obtained from the same
  • Polythiourethane-based polymerizable composition and optical resin obtained from the same
  • Polythiourethane-based polymerizable composition and optical resin obtained from the same

Examples

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preparation example Construction

[0126] The preparation method of the resin of the present invention is explained below.

[0127] The resin of this invention is obtained by making said (A)-(C) component react. The mixing order of the ingredients is not particularly limited, for example, the following methods can be mentioned:

[0128] (i) A method in which (A) component and (C) component are reacted in advance, and (B) component is added and polymerized, and

[0129] (ii) A method of mixing (A), (B) and (C) components together and polymerizing them. In addition, as a polymerization method, for example, a heat curing method can be used.

[0130] When the component (C) is a compound that does not contain any ether bond or thioether bond in its molecular structure, the method (i) above is preferable. Thereby, it is possible to further suppress severe heat generation and rapid viscosity increase at the time of mixing the components.

[0131] The resin obtained by the method (i) or (ii) above has excellent imp...

Embodiment 1

[0171] At 20°C, in 57.38g of 2,5(6)-bis(isocyanatomethyl)-bicyclo[2.2.1]heptane, 0.10g of dibutyltin chloride as a curing catalyst was mixed and dissolved, 0.25 g of an internal release agent (trade name: ZelecUN), and 0.05 g of an ultraviolet absorber (trade name: BioSorb583) were prepared into a homogeneous solution. After adding 7.52 g of 1,4-butanediol to this homogeneous solution and stirring at 30° C. for 20 minutes, it was cooled to 20° C. and stirred for an additional 30 minutes. Then, 3 to 5.10 g of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane were added, mixed and dissolved.

[0172] After defoaming the homogeneous solution at 600 Pa for 1 hour, it was filtered through a filter made of 1 μm PTFE, and injected into an injection mold composed of a glass mold and a tape. The injection mold was put into an oven, and the temperature was gradually raised from 25°C to 120°C over 20 hours to carry out polymerization. After the polymerization is completed, the injection...

Embodiment 2

[0175] At 20°C, 0.10 g of dibutyltin chloride, 0.25 g of an internal release agent (trade name: ZelecUN), and 0.05 g of an ultraviolet absorber (trade name: BioSorb583) were prepared into a homogeneous solution. After adding 7.89 g of triethylene glycol to this homogeneous solution and stirring at 30° C. for 20 minutes, it was cooled to 20° C. and then stirred for 30 minutes. Then, 37.89 g of 4-mercaptomethyl-1,8-dimercapto-3,6-dithiaoctane was added, mixed and dissolved.

[0176] After defoaming the homogeneous solution at 600 Pa for 1 hour, it was filtered through a filter made of 1 μm PTFE, and injected into an injection mold composed of a glass mold and a tape. The injection mold was put into an oven, and the temperature was gradually raised from 25°C to 120°C over 20 hours to carry out polymerization. After the polymerization is completed, the injection mold is taken out from the oven, and the resin is obtained by demoulding. The resulting resin was further annealed at...

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Abstract

The present invention provides a polymerizable composition for giving a resin which has a high refractive index and low dispersion, and is especially excellent in impact resistance and tintability; and a resin and an optical component each obtained by curing the composition. There used a polymerizable composition comprising (A) a compound represented by Formula (1) and/or by Formula (2), at least one compound as the following component (B), and at least one compound as the following component (C): (B) polythiol compounds optionally having at least one (poly)sulfide bond in a molecule, and (C) compounds represented by Formula (3): HO-[R1-(Y) n ] m -R2-X (3) (in above Formula (3), X is an OH group or a SH group; Y is an oxygen atom or a sulfur atom; R1 and R2 are each independently an optionally substituted methylene group or an optionally substituted alkylene group having carbon atoms of not smaller than 2 and not larger than 4; n is an integer of 0 or 1 when Y is an oxygen atom, or 0 or an integer of not smaller than 1 and not larger than 2 when Y is a sulfur atom; and m is 0 or an integer of not smaller than 1 and not larger than 3, provided that (carbon number of R1+n) m + (carbon number of R2) is 3 or larger).

Description

technical field [0001] The present invention relates to a polymerizable composition, resin and optical components. Background technique [0002] Compared with inorganic lenses, plastic lenses are lighter, less prone to damage, and can be dyed. Therefore, in recent years, they have been rapidly popularized as optical elements such as eyeglass lenses and camera lenses. [0003] Spectacle lenses, in particular, are required to have (1) high refractive index, (2) low dispersion (high Abbe number) optical performance, (3) excellent heat resistance, ( 4) Excellent impact resistance, (5) easy to dye, (6) excellent processability such as cutting, etc., so far, various resin materials for lenses have been developed and used. [0004] Among them, polythiourethane resins are mentioned as typical examples (Patent Documents 1 and 2). [0005] In addition, among polythiourethane-based resins, a polythiourethane-based resin (Patent Document 3) using an isocyanate compound represented by ...

Claims

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Application Information

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Patent Type & Authority Applications(China)
IPC IPC(8): C08G18/75C08G18/38G02C7/02
Inventor 龙昭宪田中守奥村邦雄
Owner MITSUI CHEM INC
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