Optical material composition and optical material

Abstract

The present invention makes it possible to provide an optical material composition containing an episulfide compound (A), a polythiol compound (B), and a photochromic compound (C). The episulfide compound (A) is preferably a compound represented by formula (1), and the polythiol compound (B) is preferably a compound represented by formula (6). ##STR00001##
(In formula (1), m represents an integer of 0 to 4, and n represents an integer of 0 to 2.) ##STR00002##
(In formula (6), n represents an integer of 4 to 20, and R.sub.1 and R.sub.2 may be the same or different and represent H, SH, C.sub.1-10 alkyl groups, or C.sub.1-10 alkylthiol groups.)

Claims

1. A composition for optical materials, consisting of: an episulfide compound (A) in an amount of 65 to 90 parts by mass with respect to 100 parts by mass of the composition, a polythiol compound (B) in an amount of 10 to 35 parts by mass with respect to 100 parts by mass of the composition, a photochromic compound (C) in an amount of 0.01 to 0.5 parts by mass with respect to 100 parts by mass of the composition, and sulfur as an optional component, an optional polymerization catalyst and an optional curing catalyst; wherein the photochromic compound (C) is selected from the group consisting of a spiropyran compound, a spirooxazine compound, a spiroperimidine compound, a benzopyran compound, a fulgide compound, a naphthopyran compound, a diarylethene compound, and an azobenzene compound.

2. The composition for optical materials according to claim 1, wherein the episulfide compound (A) is a compound represented by formula (1): ##STR00016## wherein: m represents an integer of 0 to 4; and n represents an integer of 0 to 2.

3. The composition for optical materials according to claim 1, wherein the polythiol compound (B) is a compound represented by formula (5):
HSXSH(5) wherein: X represents an alkylene group having at least one selected from the group consisting of S, O and CO in the main chain, wherein the carbon number of the main chain is 4 to 20; and X may have SH, a C.sub.1-10 alkyl group, a C.sub.1-10 alkylthiol group or a C.sub.1-10 mercaptoalkylcarbonyloxy group in the side chain.

4. The composition for optical materials according to claim 1, wherein the polythiol compound (B) is a compound represented by formula (6): ##STR00017## wherein: n represents an integer of 4 to 20; and R.sub.1 and R.sub.2 may be the same or different and represent H, SH, a C.sub.1-10 alkyl group or a C.sub.1-10 alkylthiol group.

5. The composition for optical materials according to claim 4, wherein the polythiol compound (B) is a compound represented by formula (7): ##STR00018## wherein n represents an integer of 4 to 20.

6. The composition for optical materials according to claim 5, wherein n in formula (7) represents an integer of 5 to 20.

7. An optical material obtained by polymerizing and curing the composition for optical materials according to claim 1.

8. The optical material according to claim 7, having a refractive index from 1.670 to 1.701.

Description

EXAMPLES

(1) Hereinafter, the present invention will be specifically described by way of examples. However, the present invention is not limited thereto. Note that evaluation was carried out in manners described below.

(2) <Refractive index>: The e-line was measured at 20 C. using a refractometer KPR-2000 manufactured by Shimadzu Corporation.

(3) In the present invention, the refractive index is preferably 1.67 or higher, more preferably 1.68 or higher, and particularly preferably 1.69 or higher.

(4) <Photochromic performance>: The absorbance at 380 to 780 nm was measured using an absorbance measurement apparatus UV-2450 manufactured by Shimadzu Corporation.

(5) In the test, a resin flat plate having a thickness of 2 mm was irradiated with light at 365 nm using an UV irradiation apparatus SUPERCURE-204S manufactured by SAN-EI ELECTRIC CO., LTD., and irradiation was stopped when the absorbance reached the maximum value.

(6) The time from when irradiation is started till when the absorbance reaches half the maximum value (R1), the visible transmittance obtained when the absorbance reaches the maximum value (T1), the transmittance at the maximum light absorption wavelength obtained when the absorbance reaches the maximum value (T2) and the time from when irradiation is stopped till when the absorbance reaches half the maximum value (R2) were evaluated.

(7) R1 is an indication of the time required for color development, and R2 is an indication of the time required for decolorization. The shorter they are, the better the responsiveness is. In the present invention, R1 is preferably 40 seconds or less, more preferably 30 seconds or less, even more preferably 20 seconds or less, and particularly preferably 15 seconds or less. R2 is preferably 300 seconds or less, more preferably 200 seconds or less, and particularly preferably 100 seconds or less.

(8) Further, the smaller T1 is, the better the photochromic efficiency is. In the present invention, T1 is preferably 30% or less, more preferably 25% or less, and particularly preferably 20% or less. T2 is preferably 50% or less, more preferably 40% or less, and particularly preferably 30% or less.

Example 1

(9) To 100 parts by mass of a composition consisting of 85% by mass of bis(-epithiopropyl)sulfide as the episulfide compound (A), 15% by mass of 1,10-dimercaptodecane as the polythiol compound (B) and 0.02% by mass of 4-[3-phenyl-3-(4-piperidin-1-yl-phenyl)-3H-benzo[f]chromen-6-yl]morpholine as the photochromic compound (C), 0.1 parts by mass of tetrabutylphosphonium bromide as the polymerization catalyst was added, and it was homogenously mixed at room temperature and then subjected to the deaeration treatment.

(10) After that, it was filtered with a PTFE filter of 1 injected into a mold, and polymerized and cured with the temperature being elevated from 30 C. to 100 C. over 20 hours. After that, it was released from the mold and annealed at 100 C. for 1 hour, thereby obtaining a plate optical material having a thickness of 2 mm. Photochromic performance thereof is shown in Table 1.

Examples 2-5

(11) The process was carried out in a manner similar to that in Example 1, except that the composition was as shown in Table 1, thereby obtaining an optical material. Photochromic performance (R1, R2, T1, T2) thereof is shown in Table 1.

Comparative Examples 1 and 2

(12) The process was carried out in a manner similar to that in Example 1, except that the composition was as shown in Table 1, thereby obtaining an optical material. Photochromic performance (R1, R2, T1, T2) thereof is shown in Table 1.

Examples 6-28

(13) A photochromic dye manufactured by Vivimed Labs was used as the photochromic compound, and the process was carried out in a manner similar to that in Example 1 using the composition shown in Table 2, thereby obtaining an optical material. Photochromic performance (R1, R2, T2) thereof is shown in Table 2.

Comparative Examples 3 and 4

(14) The process was carried out in a manner similar to that in Examples 6-28, except that the composition was as shown in Table 2, thereby obtaining an optical material. Photochromic performance (R1, R2, T2) thereof is shown in Table 2.

(15) TABLE-US-00001 TABLE 1 Episulfide Polythiol Photochromic Other T1 (visible T2 (transmittance at compound (A) compound (B) compound (C) components Refractive R1 transmittance) maximum light absorption R2 (% by mass) (% by mass) (% by mass) (% by mass) index (sec) (%) wavelength) (%) (sec) Example 1 A-1 B-1 C-1 Not used 1.683 7 23 19 55 (85) (15) (0.02) Example 2 A-1 B-1 C-1 Sulfur (6) 1.691 15 20 17 33 (79) (15) (0.11) Example 3 A-1 B-2 C-1 Not used 1.686 10 20 17 64 (85) (15) (0.02) Example 4 A-1 B-3 C-1 Not used 1.689 15 22 18 82 (85) (15) (0.02) Example 5 A-2 B-1 C-1 Not used 1.683 12 12 10 57 (85) (15) (0.02) Comparative A-1 Not used C-1 Not used 1.707 Photochromic function did not work Example 1 (100) (0.02) Comparative A-1 Not used C-1 Sulfur (6) 1.715 Photochromic function did not work Example 2 (94) (0.02) A-1: bis(-epithiopropyl)sulfide A-2: 2,5-bis(-epithiopropylthioethylthiomethyl)-1,4-dithiane B-1: 1,10-dimercaptodecane (carbon number of main chain: 10) B-2: 1,8-dimercaptooctane (carbon number of main chain: 8) B-3: 1,6-dimercaptohexane (carbon number of main chain: 6) C-1: 4-[3-phenyl-3-(4-piperidin-1-yl-phenyl)-3H-benzo[f]chromen-6-yl]morpholine

(16) TABLE-US-00002 TABLE 2 Episulfide Polythiol Photochronic Other T2 (transmittance at compound (A) compound (B) compound (C) components Refractive R1 maximum light absorption R2 (% by mass) (% by mass) (% by mass) (% by mass) index (sec) wavelength) (%) (sec) Example 6 A-1 B-5 C-2 Not used 1.698 15 50 >300 (85) (15) (0.08) Example 7 A-1 B-5 C-2 Not used 1.700 28 6 171 (80) (20) (0.08) Example 8 A-1 B-5 C-2 Not used 1.701 8 8 19 (75) (25) (0.08) Example 9 A-1 B-6 C-2 Not used 1.670 32 50 >300 (75) (25) (0.08) Example 10 A-1 B-6 C-2 Not used 1.666 31 40 >300 (70) (30) (0.08) Example 11 A-1 B-6 C-2 Not used 1.656 8 5 54 (60) (40) (0.08) Example 12 A-1 B-1 C-2 Not used 1.686 26 4 248 (90) (10) (0.08) Example 13 A-1 B-1 C-2 Not used 1.683 12 2 77 (85) (15) (0.08) Example 14 A-1 B-1 C-2 Not used 1.678 10 2 56 (80) (20) (0.08) Example 15 A-1 B-1 C-2 Not used 1.674 8 2 46 (75) (25) (0.08) Example 16 A-1 B-1 C-2 Not used 1.671 8 2 43 (70) (30) (0.08) Example 17 A-1 B-1 C-2 Not used 1.683 10 5 70 (85) (15) (0.02) Example 18 A-1 B-1 C-3 Not used 1.683 19 1 90 (85) (15) (0.08) Example 19 A-1 B-1 C-4 Not used 1.683 12 13 20 (85) (15) (0.08) Example 20 A-1 B-2 C-2 Not used 1.686 14 3 105 (85) (15) (0.08) Example 21 A-1 B-3 C-2 Not used 1.690 17 3 136 (85) (15) (0.08) Example 22 A-1 B-4 C-2 Not used 1.693 22 6 149 (85) (15) (0.08) Example 23 A-1 B-7 C-2 Not used 1.684 38 25 >300 (85) (15) (0.08) Example 24 A-1 B-8 C-2 Not used 1.695 15 50 >300 (85) (15) (0.08) Example 25 A-1 B-1 C-2 Sulfur (6) 1.691 13 10 82 (79) (15) (0.08) Example 26 A-1 B-1 C-2 Sulfur (4) 1.686 11 5 66 (81) (15) (0.08) Example 27 A-1 B-1 C-2 Sulfur (2) 1.680 9 4 52 (83) (15) (0.08) Example 28 A-1 B-1 C-2 Sulfur (6) 1.691 13 20 33 (79) (15) (0.08) Comparative A-1 Not used C-2 Not used 1.707 Photochronic function did not work Example 3 (100) (0.08) Comparative A-1 Not used C-2 Sulfur (6) 1.715 Photochronic function did not work Example 4 (94) (0.08) A-1: bis(-epithiopropyl)sulfide B-1: 1,10-dimercaptodecane (carbon number of main chain: 10) B-2: 1,8-dimercaptooctane (carbon number of main chain: 8) B-3: 1,6-dimercaptohexane (carbon number of main chain: 6) B-4: 1,5-dimercaptopentane (carbon number of main chain: 5) B-5: 3-thia-1,5-dimercaptopentane (carbon number of main chain: 4) B-6: pentaerythritol tetrakis(3-mercaptopropionate) (carbon number of main chain: 9) B-7: 3,6-dioxa-1,8-dimercaptooctane (carbon number of main chain: 6) B-8: 3,7-dithia-1,9-dimercaptononane (carbon numer of main chain: 7) C-1: 4-[3-phenyl-3-(4-piperidin-1-yl-phenyl)-3H-benzo[f]chromen-6-yl]morpholine C-2: photochromic dye Mulberry manufactured by Vivimed Labs C-3: photochromic dye Flame manufactured by Vivimed Labs C-4: Photochromic dye Rush manufactured by Vivimed Labs