# US 4,397,651 A · Polymeric dyes derived from bis-reactive methylene compounds and aromatic di-aldehydes for paper

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- Number: US 4,397,651 A
- Document ID: US4397651A
- Status: Granted
- Kind: A
- Application number: 06/291,500
- Filed: 1981-08-10
- Granted: 1983-08-09
- Earliest claimed: 1979-03-07
- Assignees: BASF SE
- Inventors: Hans-Juergen Degen; Klaus Grychtol
- Web page: https://patentgrep.com/patent/US4397651A

## CPC

- D21H 21/28: Colorants {; Pigments or opacifying agents}
- C09B 23/10: The polymethine chain containing an even number of >CH- groups {(styryl dyes C09B23/14, C09B23/14 takes precedence)}
- C09B 69/105: {containing a methine or polymethine dye}
- Y10S 8/919: Paper
- 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)
- Y10S: TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS

## Abstract

Polymeric dyes of the general formula I ##STR1## where A is the radical of a methylene-active compound, which may or may not be quaternized, B.sup.1 and B.sup.2 are bridge members which may or may not be quaternized or B.sup.2 may be a direct bond, n is number >1, p is the number of positive charges, R is hydrogen, chlorine, bromine, hydroxyl, C.sub.1 -C.sub.8 -alkyl, nitro, C.sub.1 -C.sub.8 -alkoxy, C.sub.1 -C.sub.8 -alkoxycarbonyl, cyano, hydroxycarbonyl, unsubstituted or substituted carbamyl or unsubstituted or substituted amino, R.sup.1 is hydrogen, chlorine, hydroxyl, C.sub.1 -C.sub.4 -alkyl or C.sub.1 -C.sub.4 -alkoxy or R and R.sup.1 together are an unsubstituted or substituted fused ring, or R and R.sup.1 together with B.sup.2 are a heterocyclic radical and A.sup..crclbar. is an anion.

## Claims

### Claim 1

A paper stock dyed with a polymeric dye of the formula I ##STR214## wherein, B.sup.1 is a bridge member selected from the group consisting of: lower alkylene, substituted lower alkylene, lower alkylene and substituted lower alkylene containing --NH--, --S--, --O--, carbamyl, carbonyloxy, ##STR215## phenylene, substituted phenylene, napthylene, cycloalkylene, and heteroatom containing cycloalkylene radicals;
B.sup.2 is a direct bond between dye molecule units or is a bridge member selected from the group consisting of: ##STR216## wherein R is lower alkylene, hydroxy-substituted lower alkylene, C.sub.1 -C.sub.4 alkoxy, chloro, bromo or phenylene radicals; R.sup.2 is hydrogen, lower alkyl, or substituted lower alkyl radical; B.sup.1 is as already defined; and r is an integer from 1 to 6,
n is a number>1,
p is the number of positive charges,
A.sup.- is an anion,
R is hydrogen, chloro, bromo, hydroxyl, C.sub.1 -C.sub.8 alkyl, nitro, C.sub.1 -C.sub.8 alkoxy, C.sub.1 -C.sub.8 alkoxycarbonyl, cyano, hydroxycarbonyl, unsubstituted or substituted carbamyl or unsubstituted or substituted amino,
R.sup.1 is hydrogen, chloro, hydroxyl, C.sub.1 -C.sub.4 alkyl or C.sub.1 -C.sub.4 alkoxy or,
R and R.sup.1 together are an unsubstituted or substituted fused ring, or R and R.sup.1 together with B.sup.2 are a heterocyclic radical,
T is a straight-chain or branched alkylene radical which is unsubstituted or substituted by hydroxyl, C.sub.1 -C.sub.4 alkoxy, chlorine or bromine, or is a phenylene radical,
A is the radical of a methylene-active compound selected from the group consisting of: ##STR217## wherein R and R.sup.2 are as already defined; R.sup.3 is lower alkyl or substituted lower alkyl; X is hydrogen, cyano, C.sub.1 -C.sub.8 carbamyl, C.sub.1 -C.sub.4 alkyl, or a heterocyclic radical; M is an oxygen atom or an imino group, having the structure ##STR218## and X and M may form a ring structure incorporating heteroatoms therein.

### Claim 2 (depends on 1)

The paper stock dyed with a polymeric dye as in claim 1, wherein the dye has the formula: ##STR219## wherein, A, B.sup.1, n, p and A.sup.- are as claimed in claim 1; and R.sup.4 is C.sub.1 -C.sub.4 alkyl, .beta.-cyanoethyl, cyanomethyl, .beta.-chloroethyl, .beta.-hydroxyethyl, 2-hydroxy-3-chloropropyl, and B-C.sub.1 -C.sub.4 -alkoxyethyl.