Claims
- 1. A cationic phthalocyanine dyestuff in which at least two phthalocyanine groups, which may be metallized or unmetallized, are joined by a group --CH.sub.2 --R--CH.sub.2 -- wherein R is a group of one of the formulae (a) to (d) ##STR127## where each B independently is ##STR128## R.sub.3 is C.sub.1-10 alkyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen;
- R.sub.4 is hydrogen, C.sub.1-10 alkyl unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen;
- Q is a direct bond or a bridging group; and A.sup..crclbar. is a non-chromophoric anion, the phthalocyanine groups being attached to the methylene moieties of the group --CH.sub.2 --R--CH.sub.2 --.
- 2. A cationic phthalocyanine dyestuff of the formula I ##STR129## in which Pc is a metallised or unmetallised phthalocyanine group,
- R is a group of one of the formulae (a) to (d) ##STR130## where each B independently is ##STR131## R.sub.1 is a group of the formula ##STR132## where R.sub.3 is C.sub.1-10 alkyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen;
- R.sub.4 is hydrogen, C.sub.1-10 alkyl unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen;
- Q is a direct bond or a bridging group;
- R.sub.2 is ##STR133## where either R.sub.5 and R.sub.6 independently are selected from hydrogen; C.sub.1-10 alkyl unsubstituted or substituted by one substituent selected from CN, OH, unsubstituted phenyl, halogen, --CONH.sub.2 and --COO(C.sub.1-4 alkyl); C.sub.2-10 alkenyl unsubstituted or substituted by one substituent selected from CN, OH, unsubstituted phenyl, halogen, --CONH.sub.2 and COO(C.sub.1-4 alkyl); C.sub.6-8 cycloalkyl, unsubstituted or substituted by up to three C.sub.1-4 alkyl or C.sub.1-4 alkoxy groups, which alkyl or alkoxy groups may be substituted by up to three substituents selected from OH, CN and halogen; and C.sub.6-10 aryl substituted by up to two C.sub.1-4 alkyl or C.sub.1-4 alkoxy groups which alkyl or alkoxy groups may be substituted by one substituent selected from OH, CN and halogen; or
- R.sub.5 and R.sub.6 together with the N-atom to which they are attached form a morpholine, piperidine, pyrrolidine or piperazine group each of which may be substituted by up to three C.sub.1-4 alkyl groups, which alkyl groups may be substituted by one OH, CN or halogen groups;
- and either R.sub.5a, R.sub.6a independently have the non-heterocyclic significances of R.sub.5 and R.sub.6 except for hydrogen,
- and R.sub.7 is C.sub.1-10 alkyl, unsubstituted or substituted by up to three substituents selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl, unsubstituted or substituted by one substituent selected from CN, OH, unsubstituted phenyl and halogen;
- or R.sub.5a, R.sub.6a and R.sub.7 together with the N.sup..sym. atom to which they are attached form a pyridinium ring which may be substituted by up to two C.sub.1-4 alkyl groups, which alkyl groups may be substituted by one OH, CN or halogen, or a group of formula ##STR134## A.sup..crclbar. is a non-chromophoric anion r is a number from 0 to 20;
- s is a number from 0 to 6; x is a number from 0 to 6;
- t is 0 or 1;
- q is a number from 0 to 6; y is a number from 0 to 6;
- v is a number from 0 to 1;
- w is a number from 0 to 0.5;
- with the provisos that
- (i) s+q+v on each terminal phthalocyanine moiety is 1 to 6 and
- (ii) s+q=y+1 where one of s and q is at least 1.
- 3. A phthalocyanine product according to claim 2 of formula Ia ##STR135## in which Pc' is copper-, nickel-, iron-, cobalt-, zinc or aluminium-phthalocyanine;
- R' is a group of the formula ##STR136## R.sub.1 ' is ##STR137## R.sub.2 ' is ##STR138## R.sub.3 ' is (C.sub.1-4)alkyl unsubstituted or substituted by one CN, OH or halogen group;
- R.sub.4 ' is hydrogen or C.sub.1-4 alkyl unsubstituted or substituted by one CN, OH or halogen group;
- R.sub.5 ' is selected from hydrogen; unsubstituted C.sub.1-4 alkyl; C.sub.1-4 alkyl substituted by one --COO(C.sub.1-4)alkyl, unsubstituted phenyl or --CONH.sub.2 group; C.sub.2-4 -alkyl substituted by one chloro, bromo, CN and OH group; cyclohexyl unsubstituted or substituted by one unsubstituted (C.sub.1-4)alkyl or unsubstituted (C.sub.1-4)alkoxy group; and phenyl, unsubstituted or substituted by one (C.sub.1-4)alkyl or one (C.sub.1-4)alkoxy group, where the alkyl or alkoxy group may be substituted by one substituent selected from halogen, OH and CN;
- R.sub.6 ' is selected from hydrogen, unsubstituted C.sub.1-4 alkyl, unsubstituted cyclohexyl, (C.sub.2-4)alkyl substituted by one chloro, bromo, OH or CN group and unsubstituted phenyl;
- or R.sub.5 ' and R.sub.6 ' together with the N-atom to which they are attached form an unsubstituted morpholine, an unsubstituted piperidine, an unsubstituted pyrrolidine, an N-methyl piperazine or an unsubstituted piperazine and
- R.sub.5a ' and R.sub.6a ' independently, have the non-heterocyclic significances of R.sub.5 ' and R.sub.6 ' except for hydrogen; and
- R.sub.7 ' is unsubstituted C.sub.1-4 alkyl; or
- R.sub.5a ', R.sub.6a ' and R.sub.7 ' together with the N.sup..crclbar. atom to which they are attached form a pyridinium ring, unsubstituted or substituted by a methyl group, ##STR139## Q' is selected from a direct bond; --O--; --S--; ##STR140## a branched or straight chain (C.sub.1-10)alkylene group which may be interrupted by one --O--, --S-- or ##STR141## group or which may be substituted by one CN, OH or halogen group; or a group of the formula ##STR142## where m is 0, 1, 2, 3, 4, 5 or 6;
- R.sub.9 is hydrogen, C.sub.1-4 alkyl unsubstituted or substituted by one OH, CN or halogen group; naphthyl unsubstituted or substituted by one C.sub.1-4 alkyl group or phenyl, unsubstituted or substituted by one C.sub.1-4 alkyl group, the alkyl of which may be substituted by one OH, CN or halogen group,
- X is --NH--CO--NH; --NH--CO--(CH.sub.2).sub.m --CO--NH--; ##STR143## R.sub.10 is OH, Cl or ##STR144## each R.sub.11 independently is hydrogen, unsubstituted C.sub.1-4 alkyl or unsubstituted phenyl,
- B' is ##STR145## s' is a number not greater than 3 r' is a number from 0 to 6
- x' is s' or s'-1
- with the provisos that
- (i) s'+q+v is a number from 1 to 3; and
- (ii) s'+q=x'+y+1.
- 4. A phthalocyanine product according to claim 3 of formula (Ib) ##STR146## where R.sub.a is ##STR147## and r" is a number from 0 to 4, with the provisos that (i) y+1=q and
- (ii) q+v is a number from 1 to 3.
- 5. A phthalocyanine product according to claim 2 of the formula (Ic) ##STR148## in which Ro is --(CH.sub.2).sub.3 --, --(CH.sub.2).sub.4 --, --(CH.sub.2).sub.5 --, --(CH.sub.2).sub.6 --, ##STR149## B" is --NH--, N(CH.sub.3)-- or ##STR150## r" is a number from 0 to 4, s' is a number not greater than 3
- and x' is s' or s'-1
- with the provisos that
- (i) s'+v is a number from 1 to 3
- and (ii) s'=x'+1.
- 6. A compound according to claim 2 wherein Q is Q' where Q' is selected from a direct bond; --O--; --S--; ##STR151## a branched or straight clain (C.sub.1-10)alkylene group which may be interrupted by one --O--, --S-- or ##STR152## group or which may be substituted by one CN, OH or halogen group; or a group of the formula ##STR153## where m is 0, 1, 2, 3, 4, 5 or 6;
- R.sub.9 is hydrogen, C.sub.1-4 alkyl unsubstituted or substituted by one OH, CN or halogen group; naphthyl unsubstituted or substituted by one C.sub.1-4 alkyl group or phenyl, unsubstituted or substituted by one C.sub.1-4 alkyl group, the alkyl of which may be substituted by one OH, CN or halogen group,
- R.sub.4 ' is hydrogen or C.sub.1-4 alkyl unsubstituted or substituted by one --CN, --OH or halogen group;
- X is --NH--CO--NH; --NH--CO--(CH.sub.2).sub.m --CO--NH--; ##STR154## R.sub.10 is OH, Cl or ##STR155## and each R.sub.11 independently is hydrogen, unsubstituted C.sub.1-4 alkyl or unsubstituted phenyl.
- 7. A compound according to claim 2 wherein R is a group of one of the formulae (a) to (c).
- 8. A compound according to claim 1 wherein R is a group of one of the formulae (a) to (c).
- 9. A compound according to claim 6 wherein R is a group of one of the formulae (a) to (c).
- 10. A compound according to claim 7 wherein B is B" where B" is --N.sup..sym. (CH.sub.3).sub.2 --A.sup..crclbar..
- 11. A compound according to claim 8 wherein B is B" where B" is --N.sup..sym. (CH.sub.3).sub.2 --A.sup..crclbar..
- 12. A compound according to claim 9 where B is B" where B" is --N.sup..sym. (CH.sub.3).sub.2 --A.sup..crclbar..
- 13. A compound according to claim 2 of the formula ##STR156## where each R.sub.a is ##STR157##
- 14. A mixture of compounds according to claim 2.
- 15. A mixture of compounds according to claim 6.
- 16. A mixture of compounds according to claim 12.
- 17. A mixture comprising a phthalocyanine product according to claim 2 and a phthalocyanine product of formula II ##STR158## in which Pc, q, w, v, R.sub.1 and R.sub.2 are defined in claim 2
- p is a number from 0 to 7;
- with the provisos that
- (i) p and q are not both zero
- (ii) p+q+v is not greater than 7.
- 18. A mixture to claim 17 in which the phthalocyanine of formula II is of formula IIa ##STR159## in which ##STR160## ##STR161## R.sub.4 ' is hydrogen or C.sub.1-4 alkyl unsubstituted or substituted by one CN, OH or halogen group; R.sub.5 ' is selected from hydrogen; unsubstituted C.sub.1-4 alkyl; C.sub.1-4 alkyl substituted by one --COO(C.sub.1-4)alkyl, unsubstituted phenyl or --CONH.sub.2 group; C.sub.2-4 -alkyl substituted by one chloro, bromo, CN and OH group; cyclohexyl unsubstituted or substituted by one unsubstituted (C.sub.1-4)alkyl or unsubstituted (C.sub.1-4)alkoxy group; and phenyl, unsubstituted or substituted by one (C.sub.1-4)alkyl or one (C.sub.1-4)alkoxy group, where the alkyl or alkoxy group may be substituted by one substituent selected from halogen, OH and CN;
- R.sub.6 ' is selected from hydrogen, unsubstituted C.sub.1-4 alkyl, unsubstituted cyclohexyl, (C.sub.2-4)alkyl substituted by one chloro, bromo, OH or CN group and unsubstituted phenyl;
- or R.sub.5 ' and R.sub.6 ' together with the N-atom to which they are attached form an unsubstituted morpholine, an unsubstituted piperidine, an unsubstituted pyrrolidine, an N-methyl piperazine or an unsubstituted piperazine; and
- R.sub.5a ' and R.sub.6a ' independently, have the non-heterocyclic significances of R.sub.5 ' and R.sub.6 ' except for hydrogen; and
- R.sub.7 ' is unsubstituted C.sub.1-4 alkyl; or
- R.sub.5a ', R.sub.6a ' and R.sub.7 ' together with the N.sym. atom to which they are attached form a pyridinium ring, unsubstituted or substituted by a methyl group, ##STR162## Q' is selected from a direct bond; --0--; --S--; ##STR163## a branched or straight chain (C.sub.1-10)alkylene group which may be interrupted by one --O--, --S-- or ##STR164## group or which may be substituted by one CN, OH or halogen group; or a group of the formula ##STR165## R.sub.9 is hydrogen, C.sub.1-4 alkyl unsubstituted or substituted by one OH, CN or halogen group; naphthyl unsubstituted or substituted by one C.sub.1-4 alkyl group or phenyl, unsubstituted or substituted by one C.sub.1-4 alkyl group, the alkyl of which may be substituted by one OH, CN or halogen group; ##STR166## R.sub.3 is C.sub.1-10 alkyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; or C.sub.2-10 alkenyl, unsubstituted or substituted by one group selected from CN, OH, unsubstituted phenyl and halogen; ##STR167## each R.sub.11 independently is hydrogen, unsubstituted C.sub.1-4 alkyl or unsubstituted phenyl; ##STR168## A.crclbar. is a non-chromophoric anion; m is 0, 1, 2, 3, 4, 5 or 6;
- p' is a number from 0 to 4;
- q is a number from 0 to 6;
- t is 0 or 1;
- v is a number from 0 to 1;
- and w is a number from 0 to 0.5; with the proviso that p'+q+v is a number from 2 to 4.
Priority Claims (2)
Number |
Date |
Country |
Kind |
3126458 |
Jul 1981 |
DEX |
|
3200455 |
Jan 1982 |
DEX |
|
Parent Case Info
This application is a continuation-in-part of application Ser. No. 394,400, filed July 2, 1982, abandoned.
US Referenced Citations (4)
Number |
Name |
Date |
Kind |
2513098 |
Kropa et al. |
Jun 1950 |
|
3320275 |
Dien et al. |
May 1967 |
|
3784599 |
Jefferies et al. |
Jan 1974 |
|
4394125 |
Holzle et al. |
Jul 1983 |
|
Foreign Referenced Citations (1)
Number |
Date |
Country |
1082967 |
Sep 1967 |
GBX |
Continuation in Parts (1)
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Number |
Date |
Country |
Parent |
394400 |
Jul 1982 |
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