Photochromic spirooxazine monomers and polysiloxanes

• US 5,473,068 A
• Filed: 02/17/1994
• Issued: 12/05/1995
• Est. Priority Date: 02/19/1993
• Status: Expired due to Term

• Current Assignee: Innovene USA LLC
• Original Assignee: Yeda Research and Development Co. Ltd. (Weizmann Institute of Science)
• Inventors: Zelichenok, Alexander, Buchhultz, Frida, Yitzchaik, Shlomo, Krongauz, Valeri
• Primary Examiner(s): Shaver, Paul F.
• Application Number:
  US08/197,967
• Time in Patent Office: 656 Days
• Field of Search: 544/71, 544/69
• US Class Current: 544/71
• CPC Class Codes: C07D 498/10 Spiro-condensed systems
• CPC Class Codes: C07F 7/21 Cyclic compounds having at least one ring containing silicon, but no carbon in the ring
• CPC Class Codes: C08G 77/388 containing nitrogen
• CPC Class Codes: C09D 183/08 containing silicon bound to organic groups containing atoms other than carbon, hydrogen, and oxygen
• CPC Class Codes: G02B 5/23 Photochromic filters

Abstract

A method of making a photochromic polysiloxane includes the steps of forming a photochromic spironaphthooxazine monomer including an alkene terminated side and, by addition reaction, covalently bonding the alkene carbon to [SiH] moieties of a siloxane polymer. Novel spironaphthooxazine monomers and photochromic polysiloxanes are disclosed.

Claims

1. A photochromic compound of the formula:

##STR9## wherein R¹ is selected from the group consisting of (A) hydrogen, alkyl, phenyl, benzyl, or an alkyl substituted by halogen, hydroxy, lower alkoxy, carboxyl, lower alkoxycarbonyl, and phenyl and benzyl substituted by cyano or by one or more halogens; and

(B) (CH₂)_n --CH═

CH₂ wherein n is an integer from 1 to 20;

when R¹ is (B), then R² through R⁸ are each selected from the group consisting of hydrogen, lower alkyl, and lower alkyl including substitutions from the group consisting of halogen, hydroxy, and lower alkoxy;

when R¹ is (A) then one of R² through R⁸ is (C) --X--(CH₂)_n --CH═

CH₂, wherein n is an integer from 4 to 20 and X is selected from the group consisting of a covalent bond, O, N--R'"'"', (wherein R'"'"' is H or lower alkyl), CO--O, CO--NH, and --CH═

N and the remaining ones of R² through R⁸ are selected from the group consisting of hydrogen, alkyl, and alkyl substituted by halogen, hydroxy and lower alkoxy; and

R⁹ and R¹⁰ form a condensed benzene or pyridine ring.

2. A compound of claim 1 of the formula ##STR10## wherein n is an integer from 1 through 20.

3. A compound of claim 2 wherein n is 1.

4. A compound of claim 1 of the formula ##STR11## wherein R¹, R² and R³ are lower alkyl and n is an integer from 1 through 20.

5. A compound of claim 4 wherein R¹, R², and R³ are CH₃ and n is 4.

6. A compound of claim 1 wherein the condensed benzene or pyridine ring is substituted by lower alkyl, lower alkoxy, halogen or CF₃.