Patent US4720356A successfully refreshed from Google Patents.
US4720356A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Photochromic composition resistant to fatigue
Assignee: AO Inc
•
Filing: 1987-06-04
•
Granted: 1988-01-19
•
Expires: 2007-06-04
Abstract
Abstract An organic photochromic composition comprising spiro [indoline-2,3'-[3H]-naphth [2,1-b] [1,4] oxazine] dye (spirooxazine dye) and unconventional ultraviolet stabilizers. The ultraviolet stabilizers improve the light fatigue resistance of the spirooxazine (S.O.) dye and will not hinder the photocolorability of the photochromic composition. The unconventional ultraviolet stabilizers belong to the class of hindered amine light stabilizers (HALS) and excited state quenchers.
Inventors
- 👤 Nori Y. C. Chu
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 05:23
CPC Classifications
G; G03; G03C; G03C1/00; G03C1/685; G03C1/72; G03C1/73
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
76 words
A photochromic composition comprising at least one photochromic compound having the structural formula ##STR12## wherein one of R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, halogen, lower alkoxy, and lower alkyl and the others are hydrogen; R 4 and R 5 are selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, and trifluoromethyl; and R 6 is lower alkyl; and a hindered amine light stabilizer.
Claim 2
Dependent Claim
76 words
A photochromic composition comprising at least one photochromic compound having the structural formula ##STR12## wherein one of R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, halogen, lower alkoxy, and lower alkyl and the others are hydrogen; R 4 and R 5 are selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, and trifluoromethyl; and R 6 is lower alkyl; and a hindered amine light stabilizer.
Claim 3
Dependent Claim
14 words
A composition according to claim 1 additionally comprising a singlet oxygen quencher ultraviolet stabilizer.
Claim 4
Dependent Claim
23 words
A composition according to claim 2 wherein said singlet oxygen quencher ultraviolet stabilizer is a Ni 2+ ion complex with an organic ligand.
Claim 5
Dependent Claim
38 words
A composition according to claim 2 wherein said singlet oxygen quencher ultraviolet stabilizer is selected from [2,2'-thiobis [4-(1,1,3,3-tetramethylbutyl)phenolato] (butylamine)] nickel, nickel [0-ethyl(3,5-di-tert-butyl-4-hydroxybenzyl)] phosphonate, nickel dibutyldithiocarbamate, nickel di-isopropyl dithiophosphate, bis [2,2'-thiobis-4-(1,1,3,3-tetramethylbutyl)phenolato] nickel, cobalt (III) tris-di-n-butyldithiocarbamate, and cobalt (II) diisopropyldithiocarbamate.
Claim 6
Dependent Claim
19 words
A spirooxazine photochromic composition having incorporated therein a hindered amine light stabilizer to increase the light fatigue resistance thereof.
Claim 7
Dependent Claim
19 words
A spirooxazine photochromic composition having incorporated therein a hindered amine light stabilizer to increase the light fatigue resistance thereof.
Claim 8
Dependent Claim
289 words
A composition according to claim 5, 1, 2, 3 or 4 wherein said hindered amine light stabilizer is selected from one or more compounds of the following formulae: ##STR13## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are lower alkyl, R 3 and R 8 are selected from lower alkyl and hydrogen, and n is 1-12; ##STR14## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are lower alkyl, and R 3 and R 8 are selected from lower alkyl and hydrogen; ##STR15## wherein R 1 , R 4 , R 5 , R 11 and R 16 are selected from lower alkyl and hydrogen, R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 17 and R 18 are lower alkyl; n 1 is 1-12, and n 2 is 1-15; ##STR16## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are lower alkyl, R 3 and R 8 are selected from lower alkyl and hydrogen, n 1 is 1-12 and n 2 is 1-15; ##STR17## wherein R 1 , R 2 , R 3 , and R 4 are lower alkyl, and n is 1-15; and (C 26 H 52 N 4 ) n wherein n is 1-15.
Claim 9
Dependent Claim
35 words
A composition according to claim 6 wherein said hindered amine light stabilizer is selected from one or more of bis(2,2,6,6-tetramethyl-4-piperidinyl) sebacate; bis(1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate; di(1,2,2,6,6-pentamethyl-4-piperdinyl)-butyl(3',5'-ditertbutyl-4-hydroxybenzyl)malonate; poly[(6-[(1,1,3,3-tetramethylbutyl)amino]1,3,5-triazine-2,4-diyl)(1,6-[2,2,6,6-tetramethyl-4-piperidinyl] amino-hexamethylene)]; poly[[6-(morpholino)-s-triazine-2,4-diyl] [1,6-(2,2,6,6-tetramethyl-4-piperidyl) amino]-hexamethylene]; and dimethyl succinate polymer with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol.
Claim 10
Dependent Claim
11 words
A composition according to claim 6 additionally comprising a plastic host.
Claim 11
Dependent Claim
31 words
A composition according to claim 8 containing about 0.1% to about 15% by weight of said photochromic compound and about 0.01% to about 5% by weight of said stabilizer or stabilizers.
Claim 12
Independent Claim
24 words
A method of increasing the light fatigue resistance of a spirooxazine photochromic composition which comprises incorporating in said composition a hindered amine light stabilizer.
Claim 13
Independent Claim
24 words
A method of increasing the light fatigue resistance of a spirooxazine photochromic composition which comprises incorporating in said composition a hindered amine light stabilizer.
Claim 14
Dependent Claim
18 words
A method according to claim 10 wherein said photochromic composition additionally contains a singlet oxygen quencher ultraviolet stabilizer.
Claim 15
Dependent Claim
23 words
A method according to claim 11 wherein said singlet oxygen quencher ultraviolet stabilizer is a Ni 2+ ion complex with an organic ligand.
Claim 16
Dependent Claim
40 words
A method according to claim 11 wherein said singlet oxygen quencher ultraviolet stabilizer is selected from [2,2'-thiobis [4-(1,1,3,3-tetramethylbutyl) phenolato] (butylamine)] nickel, nickel [0-ethyl(3,5-di-tert-butyl-4-hydroxybenzyl)] phosphonate, nickel dibutyldithiocarbamate, nickel di-isopropyl dithiophosphate, bis [2,2'-thiobis-4-(1,1,3,3-tetramethylbutyl) phenolato] nickel, cobalt (III) tris-di-n-butyldithiocarbamate, and cobalt (II) diisopropyldithiocarbamate.
Claim 17
Dependent Claim
24 words
A method according to claim 13 wherein said photochromic composition comprises a polymer containing about 0.1% to about 15% by weight spirooxazine photochromic dye.
Claim 18
Dependent Claim
37 words
A method according to claim 14 wherein said hindered amine light stabilizer and said singlet oxygen quencher ultraviolet stabilizer are incorporated in said photochromic composition in a total amount of about 0.01% to about 5% by weight.
Claim 19
Dependent Claim
17 words
A method according to claim 15 wherein said hindered amine light stabilizer is a tetramethyl piperidine derivative.
Claim 20
Independent Claim
290 words
A method according to claims 10, 11, 12, 13, 14 or 15 wherein said hindered amine light stabilizer is selected from one or more compounds of the following formulae: ##STR18## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are lower alkyl, R 3 and R 8 are selected from lower alkyl and hydrogen, and n is 1-12; ##STR19## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , R 10 , R 11 , R 12 , R 13 , R 14 , R 15 , R 16 and R 17 are lower alkyl, and R 3 and R 8 are selected from lower alkyl and hydrogen; ##STR20## wherein R 1 , R 4 , R 5 , R 11 and R 16 are selected from lower alkyl and hydrogen, R 2 , R 3 , R 7 , R 8 , R 9 , R 10 , R 12 , R 13 , R 14 , R 15 , R 17 and R 18 are lower alkyl; n 1 is 1-12, and n 2 is 1-15; ##STR21## wherein R 1 , R 2 , R 4 , R 5 , R 6 , R 7 , R 9 , and R 10 are lower alkyl, R 3 and R 8 are selected from lower alkyl and hydrogen, n 1 is 1-12 and n 2 is 1-15; ##STR22## wherein R 1 , R 2 , R 3 , and R 4 are lower alkyl, and n is 1-15; and (C 26 H 52 N 4 ) n wherein n is 1-15.
Claim 21
Dependent Claim
79 words
A method according to claim 17 wherein said photochromic composition contains one or more of a spirooxazine photochromic dye of the formula ##STR23## wherein one of R 1 , R 2 and R 3 is selected from the group consisting of hydrogen, halogen, lower alkoxy, and lower alkyl and the others are hydrogen; R 4 and R 5 are selected from the group consisting of hydrogen, lower alkyl, lower alkoxy, halogen, and trifluoromethyl; and R 6 is lower alkyl.
Claim 22
Dependent Claim
38 words
A method according to claim 18 wherein said hindered amine light stabilizer is selected from one or more of bis (2,2,6,6-tetramethyl-4-piperidinyl) sebacate; bis (1,2,2,6,6-pentamethyl-4-piperidinyl) sebacate; di(1,2,2,6,6-pentamethyl-4-piperidinyl)-butyl(3',5'-diterbutyl-4-hydroxybenzyl) malonate; poly[(6-[(1,1,3,3-tetramethylbutyl)amino]-1,3,5-triazine-2,4-diyl)(1,6-[2,2,6,6-tetramethyl-4-piperidinyl] amino-hexamethylene)]; poly[[6-(morpholino)-s-triazine-2,4-diyl] [1,6-(2,2,6,6-tetramethyl-4-piperidyl) amino]-hexamethylene]; and dimethyl succinate polymer with 4-hydroxy-2,2,6,6-tetramethyl-1-piperidineethanol.
References Cited (Backward Citations)
US3212898A
Cited
US3666352A
Cited
US4046737A
Cited
US4049647A
Cited
JPS4953180A
Cited
US4215010A
Cited
US4342668A
Cited
US4289497A
Cited
US4440672A
Cited
JPS6042482A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1991-01-18 | 1991-07-20 | 1992-01-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1995-01-18 | 1995-07-20 | 1996-01-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1999-01-18 | 1999-07-20 | 2000-01-19 | $7700.00 | Window Closed / Lapsed |