Organic compounds -- part of the class 532-570 series – Organic compounds – Unsubstituted hydrocarbyl chain between the ring and the -c-...
Patent
1998-02-05
1999-11-23
Higel, Floyd D.
Organic compounds -- part of the class 532-570 series
Organic compounds
Unsubstituted hydrocarbyl chain between the ring and the -c-...
544 61, 544150, 546144, 546167, 546196, 5483114, 548427, 548465, 548525, 548962, 549389, B07D31192, B07D40504, B07D40704, B07D40904, C08K 515, C09K 900
Patent
active
059903058
DESCRIPTION:
BRIEF SUMMARY
This application is a national stage application (371) of PCT/DE96/02049, filed on Oct. 28, 1996.
TECHNICAL FIELD
The present invention relates to photochromic diaryl-3H-naphthopyrans.
STATE OF THE ART
Photochromic compounds possess the property that they change color reversibly under the influence of light containing a certain amount of ultra-violet radiation, such as for instance sunlight or the light from a mercury vapor lamp. This coloring is due to a bond opening in the pyran ring of the photochromic naphthopyran induced by the high-energy ultra-violet light. After removing the ultraviolet radiation source, the compound returns to its original closed state.
A variety of classes of photochromic compounds have been known for some time and are used in various applications requiring reversible light-dependent coloring, by way of illustration by means of the ultraviolet part of the sunlight.
A variety of methods for coloring plastic articles using photochromic compounds are described in the state of the art. With regard to this reference is made , by way of example, to U.S. Pat. No. 4,286,957, DE-A 35 16 568 and EP 0 227 337 B1.
The basic chemical structure of benzopyrans and naphthopyrans is described by Becker in U.S. Pat. No. 3,567,605. However these compounds, which were patented as early as in 1971, are hardly of significance for use in the production of photochromic articles, because their color is dependent on irradiation with ultraviolet light only at temperatures in the -40.degree. C. range.
Moreover, U.S. Pat. No.: 5,066,818 discloses that photochromic compounds that are suited for use at normal temperatures are obtained by introducing at least one ortho-substituted phenyl group in the 3H-position of the pyran ring. These compounds can be employed, by way of illustration, in optical lenses or other transparent plastic articles.
A further development of the general naphthopyran compounds known from U.S. Pat. No. 5,066,818 is described in U.S. Pat. No. 5,369,158. According to this printed publication, the photochromic naphthopyrans possess particularly advantageous properties if they are substituted at the 8-position of the naphthalene portion. Compared to other naphthopyrans with substitutents in the 5-, 7- or 9- position, these photochromic compounds exhibit a considerable bathochromic shift of the absorption maximum in the activated as well as in the non-activated state. Furthermore, this shift leads to increased darkening velocity and greater optical density in the photochromic compound.
The naphthopyrans of U.S. Pat. No. 5,369,158 have the following structure: ##STR1## with R5 and R9 being H, C.sub.1 -C.sub.4 alkoxy or C.sub.1 -C.sub.4 alkyl, R8 being halogen, C.sub.1 -C.sub.5 acyloxy, benzoyloxy, methoxybenzoyloxy or di(C.sub.1 -C.sub.5)alkylamino or LO-, wherein L is C.sub.1 -C.sub.12 alkyl, C.sub.6 -C.sub.9 aryl (C.sub.1 -C.sub.3) alkyl, C.sub.5 -C.sub.7 cycloalkyl or C.sub.5 -C.sub.7 cycloalkyl substituted by C.sub.1 -C.sub.4 alkyl and B and B' are substituted or unsubstituted phenyl or naphthyl, pyridyl, thienyl, benzothienyl, furyl or benzofuryl, with the substituent or substituents being C.sub.1 -C.sub.4 alkyl, C.sub.1 -C.sub.4 halogen alkyl, C.sub.1 -C.sub.4 alkoxy, C.sub.1 -C.sub.4 -alkoxy(C.sub.1 -C.sub.4) alkyl, di (C.sub.1 -C.sub.5) alkylamino or halogen provided that at least one of the residues B or B' is substituted or unsubstituted phenyl or B and B' together form an adamantane residue.
Furthermore this printed publication mentions that ultra-violet absorbers or stabilizers like hindered amine functions (HALS) or singulet oxygen removers can be added to the photochromic compounds in order to improve the stability and the lifetime.
Photochromic naphthopyrans having an amide substituent, which can be a acyclic amide, at the 9-position of the basic naphthopyran structure are known from PCT/WO 95/00867. This substitution causes the absorption maximum to shift into the longwave range but also results in diminished maximum darkening and slower darkening velocity.
DESCRIPTION
REFERENCES:
patent: 3567605 (1971-03-01), Becker
patent: 5066818 (1991-11-01), Gemert et al.
patent: 5274132 (1993-12-01), VanGemert
patent: 5369158 (1994-11-01), Knowles
patent: 5411679 (1995-05-01), Kumar
patent: 5656206 (1997-08-01), Knowles et al.
patent: 5658500 (1997-08-01), Kumar et al.
patent: 5658501 (1997-08-01), Kumar et al.
Momota et al, Chemical Abstracts, vol. 125, No. 15, #195483Z, 1996.
Matsuoka et al, Chemical Abstracts, vol. 125, No. 17, #221584V, 1996.
Melzig Manfred
Zinner Herbert
Higel Floyd D.
Optische Werke G. Rodenstock
LandOfFree
Photochromic diaryl-3H-naphthopyrane does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Photochromic diaryl-3H-naphthopyrane, we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Photochromic diaryl-3H-naphthopyrane will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-1223324