# US 4,393,005 A · Cationic phthalocyanine dyes

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- Number: US 4,393,005 A
- Document ID: US4393005A
- Status: Granted
- Kind: A
- Application number: 06/357,808
- Filed: 1982-03-15
- Granted: 1983-07-12
- Earliest claimed: 1981-03-21
- Assignees: BASF SE
- Inventors: Manfred Patsch; Manfred Ruske; Erwin Hahn
- Web page: https://patentgrep.com/patent/US4393005A

## CPC

- D21H 21/28: Colorants {; Pigments or opacifying agents}
- C09B 47/16: having alkyl radicals substituted by nitrogen atoms
- C09B 47/24: Obtaining compounds having —COOH or —SO3H radicals, or derivatives thereof, directly bound to the phthalocyanine radical
- C09B 47/32: Cationic phthalocyanine dyes
- D21H: PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- C09B: ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES {, e.g. PIGMENTS}; MORDANTS; LAKES (fermentation or enzyme using processes to synthesise a desired chemical compound C12P)

## Abstract

Cationic phthalocyanine dyes of the formula ##STR1## where Pc is an (m+n+p)-valent phthalocyanine radical, R.sup.1 is H or alkyl, R.sup.2 and R.sup.3 independently of one another are alkyl, hydroxyalkyl, cycloalkyl, benzyl, phenyl or tolyl, or ##STR2## is pyrrolidinyl, imidazolyl, 2-ethyl-4-methylimidazolyl, morpholinyl, piperazinyl or N'-alkylpiperazinyl, or is ##STR3## R.sup.4 is H or methyl, R.sup.5 is alkyl, hydroxyalkyl or benzyl, X.sup..sym. is one equivalent of an anion, M.sup..crclbar. is one equivalent of a cation, z is 1 or 2, p is 0 or 1, m is 0 or 1 and n is from 1 to 4, and 1<(m+n)<4, are readily or highly soluble in water and very substantive on paper, and accordingly are particularly suitable for dyeing and printing paper. Paper dyed with (I) has very good bleeding fastness, and a colorless effluent is obtained when paper is wet-end dyed.

## Claims

### Claim 1

A cationic phthalocyanine dye of the formula ##STR36## where Pc is an (n+m+p)-valent radical of a phthalocyanine, R.sup.1 is hydrogen or C.sub.1 -C.sub.4 -alkyl, R.sup.2 and R.sup.3 independently of one another are C.sub.1 -C.sub.14 -alkyl, C.sub.2 -C.sub.4 -hydroxyalkyl, C.sub.5 -C.sub.8 -cycloalkyl, benzyl, phenyl or tolyl, or ##STR37## is a pyrrolidine, imidazole, 2-ethyl-4-methylimidazole, morpholine, piperazine or N'--C.sub.1 -C.sub.4 -alkylpiperazine radical, or is ##STR38## R.sup.4 is hydrogen or methyl, R.sup.5 is C.sub.1 -C.sub.12 -alkyl, C.sub.2 -C.sub.4 -hydroxyalkyl, chlorine-substituted C.sub.2 -C.sub.4 -hydroxyalkyl or benzyl, X.sup..crclbar. is one equivalent of an anion, M.sup..sym. is one equivalent of a cation, z is a 1 or 2, p is 0 or 1, m is 0 or 1 and n is 1, 2, 3 or 4, and 1<(m+n)<4.

### Claim 2 (depends on 1)

A dye as claimed in claim 1, wherein Pc is an (m+n+p)-valent radical of copper phthalocyanine.

### Claim 3 (depends on 1, 2)

A dye as claimed in claim 1 or 2, wherein R.sup.1 and R.sup.4 are hydrogen.

### Claim 4 (depends on 1, 2)

A dye as claimed in claim 1 or 2, wherein R.sup.2 and R.sup.3 are C.sub.1 -C.sub.5 -alkyl, or ##STR39## is morpholinyl, piperidinyl or pyrrolidinyl, and R.sup.5 is C.sub.1 -C.sub.4 -alkyl, 2-hydroxyethyl, 2-hydroxy-3-chloropropyl or benzyl and X.sup..crclbar. and Cl.sup..crclbar., H.sub.3 COSO.sub.3.sup..crclbar., benzenesulfonate, toluenesulfonate, acetate, methoxyacetate, lactate or HO.sup..crclbar..

### Claim 5 (depends on 3)

A dye as claimed in claim 3, wherein R.sup.2 and R.sup.3 are C.sub.1 -C.sub.5 -alkyl, or ##STR40## is morpholinyl, piperidinyl or pyrrolidinyl, and R.sup.5 is C.sub.1 -C.sub.4 -alkyl, 2-hydroxyethyl, 2-hydroxy-3-chloropropyl or benzyl and X.sup..crclbar. is Cl.sup..crclbar., H.sub.3 COSO.sub.3.sup..crclbar., benzenesulfonate, toluenesulfonate, acetate, methoxyacetate, lactate or HO.sup..crclbar..

### Claim 6 (depends on 3)

A dye as claimed in claim 3, wherein the average value of p is from 0 to 0.5.

### Claim 7 (depends on 4)

A dye as claimed in claim 4, wherein p is 0.

### Claim 8

A cationic phthalocyanine dye of the formula: ##STR41## where n' is 1, 2 or 3, R.sup.6 and R.sup.7 are C.sub.1 -C.sub.5 -alkyl, or ##STR42## is morpholinyl or pyrrolidinyl, and R.sup.8 is C.sub.1 -C.sub.4 -alkyl, 2-hydroxyethyl, 2-hydroxy-3-chloropropyl or benzyl and Y.sup..crclbar. is HO.sup..crclbar., benzenesulfonate, toluenesulfonate, H.sub.3 COSO.sub.3.sup..crclbar., Cl.sup..crclbar., acetate, methoxyacetate or lactate.

### Claim 9 (depends on 8)

A cationic dye as claimed in claim 8, wherein ##STR43## is di-n-propylamino, di-n-butylamino or pyrrolidinyl, R.sup.8 is 2-hydroxyethyl or benzyl and Y.sup..crclbar. is HO.sup..crclbar., acetate, methoxyacetate or lactate.