Merocyanine derivatives

Patent metadata

Field	Value
Publication number	US-9550730-B2
Application number	US-201214232915-A
Country	US
Kind code	B2
Filing date	Jul 19, 2012
Priority date	Jul 21, 2011
Publication date	Jan 24, 2017
Grant date	Jan 24, 2017

Abstract

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.

First claim

The invention claimed is:

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

Assignees

• Winkler Barbara
• Hueglin Dietmar
• Eichin Kai
• Ehrsam Larissa
• Marat Xavier
• Richard Hervé
• Kienzle Ilona Marion
• Schroeder Ute
• Basf Se

Inventors

• Winkler Barbara
• Hueglin Dietmar
• Eichin Kai
• Ehrsam Larissa
• Marat Xavier
• Richard Hervé
• Kienzle Ilona Marion
• Schroeder Ute

Classifications

• C07D307/52

  Radicals substituted by nitrogen atoms not forming part of a nitro radical · CPC title

• C08K5/3435

  Piperidines · CPC title

• C07C255/30 Primary

  containing cyano groups and singly-bound nitrogen atoms, not being further bound to other hetero atoms, bound to the same unsaturated acyclic carbon skeleton · CPC title

• C07D295/14

  substituted by carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals · CPC title

• C07D317/28

  Radicals substituted by nitrogen atoms (nitro radicals C07D317/16) · CPC title