Photochromatic compounds, process for their preparation and...

Details Photochromatic compounds, process for their preparation and... Photochromatic compounds, process for their preparation and...

2000-03-06

2002-07-02

Sanders, Kriellion A. (Department: 1714)

Synthetic resins or natural rubbers -- part of the class 520 ser

Synthetic resins

Processes of preparing a desired or intentional composition...

C252S583000, C252S586000, C544S071000, C524S090000

Reexamination Certificate

active

06414057

ABSTRACT:

The present invention relates to photochromatic compounds.
More specifically, the present invention relates to photochromatic compounds belonging to the group of spiro-isoindolino-oxazines, a process for their preparation and their use in polymeric materials.
A further object of the present invention relates to polymeric compositions containing said photochromatic compounds and the photochromatic articles obtained from their processing.
Photochromatic compounds are substances which have the characteristic of reversibly changing colour and/or degree of light transmission when exposed to solar or artificial light in the band ranging from UV to visible, or to some types of electromagnetic radiation, returning to their original state of colour and transmission when the initial light source is removed.
There are numerous substances with photochromatic characteristics, which belong to various groups of both organic and inorganic compounds such as, for example, those described in the texts “Photochromism”, by G. H. Brown (Ed.), Vol. III of the Weissberger series “Techniques of Organic Chemistry”, Wiley Interscience, New York (1971) and in “Photochromsim: Molecules and Systems”, by H. Duerr and H. Bouas-Laurent (Ed.), Vol. 40 of the series “Studies in Organic Chemistry” Elsevier (1990).
Among organic photochromatic compounds, those belonging to the groups of spiro-indolino-oxazines, spiro-pyranes and chromenes, are particularly known and used.
The above compounds are capable of giving photochromatic characteristics to polymerized organic materials used, for example, in the production of photochromatic lenses for eye-glasses, special inks, toys, and in many other applications.
As an example, the following patents can be mentioned: U.S. Pat. Nos. 3,562,172, 3,578,602, 4,215.010, 4,342,668, 5,055,576, 5,110,922, 5,186,867, EP 146.135, EP 134.633, EP 141.407, EP 245.020, IT 1.223.348 and IT 1.238.694.
Compounds belonging to the group of spiro-indolino-oxazines have, with respect to other known compounds such as, for example, compounds belonging to the group of spiro-pyranes, the advantage of having a much higher stress resistance when subjected to light and darkness cycles and also have good dyability characteristics.
The Applicant has now found photochromatic compounds belonging to the group of spiro-isoindolino-oxazines which have excellent photochromatic characteristics, excellent stress resistance and high dyability characteristics.
The present invention therefore relates to photochromatic compounds belonging to the group of spiro-isoindolino-oxazines having general formula (I):
wherein:
a) R represents a linear or branched C
1
-C
10
alkyl group, said alkyl group optionally substituted with 1-10 halogen atoms selected from fluorine, chlorine and bromine, or with hydroxyl groups, linear or branched C
1
-C
6
alkoxyl groups, carboxyl groups, cyano groups, or with a 2,2,6,6-tetramethylpiperidine group; a linear or branched C
2
-C
6
alkenyl group; an aryl group selected from phenyl, biphenyl and naphthyl, said aryl group optionally substituted with linear or branched (C
1
-C
6
) alkoxyl groups, carboxyl groups, amine groups, N,N-dialkyl (C
1
-C
6
) amine groups; a benzyl group;
b) R
1
and R
2
, the same or different, represent a linear or branched C
1
-C
10
alkyl group, said alkyl group optionally substituted with 1-10 halogen atoms selected from fluorine, chlorine and bromine, or with hydroxyl groups, linear or branched C
1
-C
6
alkoxyl groups, carboxyl groups, cyano groups; a linear or branched C
2
-C
10
alkenyl group; a benzyl group; a linear or branched C
1
-C
6
alkoxyl group; an N-alkyl (C
1
-C
6
) amine group; an N,N-dialkyl (C
1
-C
6
) amine group; or R
1
and R
2
, considered jointly with the carbon atom to which they are bound, represent a C
4
-C
10
cycloalkyl group, said cycloalkyl group optionally substituted with halogen atoms selected from fluorine, chlorine and bromine, or with hydroxyl groups, linear or branched C
1
-C
6
alkoxyl groups, carboxyl groups, cyano groups, amine groups, N-alkyl (C
1
-C
6
) amine groups, N,N-dialkyl (C
1
-C
6
) amine groups; an N,N-dialkyl (C
1
-C
6
) amide group; a cyano group; an aryl group selected from phenyl and biphenyl;
c) R
3
, R
4
, R
5
and R
6
the same or different, represent a hydrogen atom; a halogen atom selected from fluorine, chlorine, bromine and iodine; a linear or branched C
1
-C
6
alkyl group, said alkyl group optionally substituted with 1-6 halogen atoms selected from fluorine, chlorine and bromine, or with hydroxyl groups, linear or branched C
1
-C
6
alkoxyl groups, cyano groups; a benzyl group; a hydroxyl group; a linear or branched C
1
-C
6
alkoxyl group; an amine group; an N-alkyl (C
1
-C
6
) amine group; an N,N-dialkyl (C
1
-C
6
) amine group; a piperidine, piperazine or morpholine group; a C
1
-C
6
carboxyalkyl group; a C
2
-C
6
carboxyalkenyl group; a carboxyamide group; an N-alkyl (C
1
-C
6
) carboxyamide group; an N,N-dialkyl (C
1
-C
6
) carboxyamide group; a cyano group; a nitro group; a sulfonic group; an aryl group selected from phenyl, biphenyl and naphthyl, said aryl group optionally substituted with N,N-dialkyl (C
1
-C
6
) amine groups, linear or branched C
1
-C
6
alkoxyl groups, hydroxyl groups, linear or branched C
1
-C
6
alkyl groups; an acyl group of the alkyl ketone, aryl ketone or benzyl ketone type; a linear or branched C
2
-C
6
alkenyl group, said alkenyl group optionally subsituted with one or two N,N-dialkyl (C
1
-C
6
) 4-aniline groups; an N-2,3-dihydroindoline group; a linear or branched C
1
-C
6
thioether group;
d) two consecutive substituents between R
3
and R
6
, can represent condensation points with other aromatic, heterocyclic or quinonic rings;
e) R
7
represents a hydrogen atom; a halogen atom selected from fluorine, chlorine and bromine; a linear or branched C
1
-C
6
alkyl group; a linear or branched C
1
-C
6
alkoxyl group; a phenyl group; a phenoxyl group;
f) P represents a monocyclic or polycyclic aromatic nucleus, belonging to one of the following types: benzenic represented by general formula (II); naphthalenic represented by general formula (III); quinolinic represented by general formula (IV); isoquinolinic represented by general formula (V); cumarinic represented by general formula (VI); quinazolinic represented by general formula (VII); phenanthrenic represented by general formula (VIII); anthracenic represented by general formula (IX):
 wherein:
at least two adjacent substituents between R
8
and R
13
, R
14
and R
21
, R
22
and R
28
, R
30
and R
35
, R
36
and R
41
, R
44
and R
47
, R
48
and R
57
, R
58
and R
67
, represent the condensation points with the oxazine ring, the other substituents having the same meaning described under point c).
Preferred compounds having general formula (I) for the purposes of the present invention are those in which:
R represents one of the following groups: methyl, ethyl, isopropyl, 2-allyl, 2-hydroxyethyl, 2-carboxymethyl, phenyl, 4-N,N-dimethylaminoaniline, 4-methoxybenzene, 4-cyanobenzene;
R
1
and R
2
, the same or different, represent a methyl or phenyl group; or considered jointly with the carbon atom to which they are bound, represent a cyclohexyl group;
R
3
, R
4
, R
5
and R
6
, the same or different, represent a hydrogen atom, a fluorine atom, a chlorine atom, a bromine atom, or one of the following groups: methyl, isopropyl, hydroxyl, methoxyl, N,N-dimethylamine, piperidine, morpholine, carboxyl, carboxymethyl, N,N-dimethylcarboxyamide, cyano, nitro, methylketone, phenylketone, phenyl;
R
7
represents a hydrogen atom, a chlorine atom, a bromine atom, a methyl group or a phenyl group;
P represents one of the groups having general formula (II) to (IX), wherein:
i) two adjacent substituents between R
8
and R
13
, R
14
and R
21
, R
22
and R
28
, R
30
and R
35
, R
36
and R
41
, R
44
and R
47
, R
48
and R
57
, R
58
and R
67
, independently represent the condensation point with the oxazine ring and the other substituents each independently represent a hydrogen atom, a fluorine atom, a chlorine atom, a b

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