Merocyanine derivatives
Disclosed are compounds of formula (1) and (2) and/or E/E-, E/Z- or Z/Z geometrical isomer forms thereof; wherein R1-R5, R1-R11 and A are defined as in description. The compounds are used as UV absorbers for protecting household products from photolytic and oxidative degradation, as plastic additives, preferably for food and pharmaceutical packaging applications, for preventing photo-degradation of food by incorporation of the compounds of formula (1′) and/or (2′) into transparent food containers, for protection of UV-A sensitive drugs from photo-degradation by incorporation of UV absorber in transparent blister foils or transparent pharmacy containers, as additives for photographic and printing applications, as additives for electronic applications and protecting the ingredients in agriculture applications.
1. A compound of formula
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms; wherein
R 1 and R 2 independently of each other are hydrogen; C 4 -C 12 alkyl; or hydroxyl-C 3 -C 12 alkyl;
R 3 is a —(C═O)OR 6 group; or a —(CO)NHR 6 group;
R 6 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally substituted by one or more than one OH;
R 4 and R 5 are hydrogen; or R 4 and R 5 form a —(CH 2 ) n — ring which is optionally interrupted by one or more than one —O— or by —NH—;
n is a number from 2 to 7;
R 7 and R 8 independently of each other are hydrogen; C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, which is interrupted by one or more than one O or substituted by one or more than one OH, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, wherein said C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl is optionally interrupted by one or more than one —O—;
or R 7 and R 8 together with the nitrogen atom linking them form a —(CH 2 ) n — ring which is optionally interrupted by one or more than one —O—;
R 9 and R 10 are hydrogen; or R 9 and R 10 form a —(CH 2 ) n — ring which is optionally interrupted by —O— or by —NH—;
A is —O—; or —NH;
R 11 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally interrupted by one or more than one O; or C 1 -C 22 alkyl or C 2 -C 22 alkenyl which is substituted by C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, wherein said C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl is optionally interrupted by one or more than one —O—;
with the proviso that
(I) at least one of R 1 , R 2 , and R 6 is substituted by hydroxyl;
(II) if one of R 1 is hydroxyethyl, R 2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if R 1 is hydrogen, R 2 is not 1-hydroxy-3-methyl-but-2-yl;
(III) if R 6 is substituted by one or more than one OH; one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the linking nitrogen form a piperidyl or morpholinyl radical; and
(IV) at least one of R 7 and R 8 , or R 11 is interrupted by one or more than one —O—.
2. The compound according to claim 1 , wherein
R 1 and R 2 independently of each other are hydrogen; C 4 -C 12 alkyl; or hydroxyl-C 3 -C 12 alkyl;
R 3 is a —(C═O)OR 6 group; or a —(CO)NHR 6 group;
R 6 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally substituted by one or more than one OH;
R 4 and R 5 are hydrogen; or R 4 and R 5 form a —(CH 2 ) n — ring which is optionally interrupted by —O— or by —NH—;
n is a number from 2 to 7;
R 7 and R 8 independently of each other are hydrogen; C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, which is interrupted by one or more than one O or substituted by one or more than one OH; or R 7 and R 8 together with the nitrogen atom linking them form a —(CH 2 ) n — ring which is optionally interrupted by one or more than one —O—;
R 9 and R 10 are hydrogen; or R 9 and R 10 form a —(CH 2 ) n — ring which is optionally interrupted by —O— or by —NH—;
A is —O—; or —NH;
R 11 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally interrupted by one or more than one O;
with the proviso that
(I) at least one of R 1 , R 2 , and R 6 is substituted by hydroxyl;
(II) if one of R 1 is hydroxyethyl, R 2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if R 1 is hydrogen, R 2 is not 1-hydroxy-3-methyl-but-2-yl;
(III) if R 6 is substituted by one or more than one OH; one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the linking nitrogen form a piperidyl or morpholinyl radical; and
(IV) at least one of R 7 and R 8 , or R 1 is interrupted by one or more than one —O—.
3. A compound which corresponds to one of the following formulas
4. A compound which is 2-ethoxyethyl(2Z)-cyano{3-[(3-methoxypropyl)amino]cyclohex-2-en-1-ylidene}ethanoate in its E/Z geometrical isomer corresponding to the formula
and/or its E/E geometrical form of formula
5. A compound of formula
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms; wherein
R 1 and R 2 independently of each other are hydrogen; C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, which are optionally substituted by at least one hydroxyl; or R 1 and R 2 together with the nitrogen atom linking them form a —(CH 2 ) n — ring which is optionally interrupted by —O— or by —NH—;
R 3 is a —(C═O)OR 6 group; or a —(CO)NHR 6 group;
R 6 is C 1 -C 12 alkyl, which is optionally substituted by one or more than one hydroxyl;
R 4 and R 5 are hydrogen; or R 4 and R 5 form a —(CH 2 ) n — ring which is optionally interrupted by one or more than one —O— or by —NH—;
n is a number from 2 to 7;
with the proviso that
(I) at least one of R 1 , R 2 , and R 6 is substituted by hydroxyl;
(II) if one of R 1 is hydroxyethyl, R 2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if R 1 is hydrogen, R 2 is not 1-hydroxy-3-methyl-but-2-yl; and
(III) if R 6 is substituted by one or more than one OH; one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the linking nitrogen form a piperidyl or morpholinyl radical.
6. The compound of formula (1) according to claim 5 , wherein
one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the nitrogen atom linking them form a —(CH 2 ) n -ring which is optionally interrupted by —O— and/or —NH—.
7. A compound of formula
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms; wherein
R 1 and R 2 respectively together with the linking nitrogen atom to form a piperidyl, radical, or a morpholinyl radical;
R 3 is a —(C═O)OR 6 group; or a —(CO)NHR 6 group;
R 6 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally substituted by one or more than one OH;
R 4 and R 5 are hydrogen; or R 4 and R 5 form a —(CH 2 ) n — ring which is optionally interrupted by one or more than one —O— or by —NH—;
n is a number from 2 to 7;
R 7 and R 8 respectively together with the linking nitrogen atom form a piperidyl radical or a morpholinyl radical;
R 9 and R 10 are hydrogen; or R 9 and R 10 form a —(CH 2 ) n — ring which is optionally interrupted by —O— or by —NH—;
A is —O—; or —NH;
R 11 is C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, which is optionally interrupted by one or more than one O; or C 1 -C 22 alkyl or C 2 -C 22 alkenyl which is substituted by C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, wherein said C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl is optionally interrupted by one or more than one —O—;
with the proviso that
(I) at least one of R 1 , R 2 , and R 6 is substituted by hydroxyl;
(II) if one of R 1 is hydroxyethyl, R 2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if R 1 is hydrogen, R 2 is not 1-hydroxy-3-methyl-but-2-yl;
(III) if R 6 is substituted by one or more than one OH; one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the linking nitrogen form a piperidyl or morpholinyl radical; and
(IV) at least one of R 7 and R 8 , or R 11 is interrupted by one or more than one —O—.
8. A compound of formula
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms; wherein
R 1 and R 2 independently of each other are hydrogen or C 1 -C 22 alkyl; or hydroxyl-C 1 -C 22 alkyl; or R 1 and R 2 together with the nitrogen atom are linked together to form a piperidyl or morpholinyl radical;
R 3 is a —(C═O)OR 6 group; or a —(CO)NHR 6 group;
R 6 is C 1 -C 22 alkyl, which may be substituted by one or more than one —OH;
R 4 and R 5 are hydrogen; or R 4 and R 5 are linked together to form a carbocyclic ring which contains 6 carbon atoms;
n is a number from 2 to 7;
with the proviso that
(I) at least one of R 1 , R 2 , and R 6 is substituted by hydroxyl;
(II) if one of R 1 is hydroxyethyl, R 2 is not hydrogen, methyl or ethyl or hydroxyethyl; and if R 1 is hydrogen, R 2 is not 1-hydroxy-3-methyl-but-2-yl; and
(III) if R 6 is substituted by one or more than one OH; one of R 1 and R 2 is C 4 -C 22 alkyl; or R 1 and R 2 together with the linking nitrogen form a piperidyl or morpholinyl radical.
9. The compound of formula (1) according to claim 8 , wherein
R 1 and R 2 independently of each other are hydrogen; or hydroxyl-C 1 -C 22 alkyl;
wherein at least one of R 1 and R 2 is hydroxyl-C 1 -C 22 alkyl;
R 3 is a —(C═O)OR 6 group; or a —(C═O)NHR 6 group;
R 6 is C 1 -C 22 alkyl; and
R 4 and R 5 are hydrogen; or R 4 and R 5 are linked together to form a carbocyclic ring which contains 6 carbon atoms.
10. A compound of formula
and/or its E/E-, E/Z- or Z/Z geometrical isomer forms; wherein
R 7 and R 8 independently of each other are hydrogen; C 1 -C 22 alkyl, C 2 -C 22 alkenyl, C 2 -C 22 alkinyl, which is interrupted by one or more than one O or substituted by one or more than one OH, C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl, wherein said C 3 -C 22 cycloalkyl or C 3 -C 22 cycloalkenyl is optionally interrupted by one or more than one —O—;
or R 7 and R 8 together with the nitrogen atom form a morpholinyl or piperidyl radical;
R 9 and R 10 are hydrogen; or R 9 and R 10 are linked together to form a carbocylic ring which contains 6 carbon atoms;
A is —O—; or —NH;
R 11 is C 1 -C 22 alkyl, which is optionally interrupted by one or more than one O;
with the proviso that
at least one of R 7 and R 8 , or R 11 is interrupted by one or more than one —O—.