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US 8,697,792 B2Granted
Migration-free coloured copolycondensates for colouring polymers
AssigneeBASF SE
InventorsThomas Ruch, Thomas Eichenberger, Peter Sutter, Christoph Krebs, Ursula Luterbacher
Life of this patent
Estimating the term…
Abstract
The invention relates to colored and/or fluorescent copolycondensates which are obtained by reaction of colorants substituted by at least two reactive groups which do not interfere with one another, with selected cyclic dicarboxylic acids (especially 1,4-cyclohexanedicarboxylic acid), aliphatic diols (especially ethylene glycol), cyclic diamines (especially isophoronediamine) and/or amino acids in particular amounts.
Claims21
A copolycondensate obtained by copolycondensation of
- at least one 1,2-C4-C8cycloalkanedicarboxylic acid, 1,3-C4-C8cycloalkanedicarboxylic acid or 1,4-C4-C8cycloalkanedicarboxylic acid, or an ester, anhydride or acid chloride thereof;
- from 0.3 to 0.8 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one 1,2-C6-C12-cycloalkanediamine, 1,3-C6-C12cycloalkanediamine or 1,4-C6-C12cycloalkanediamine, or of a latent form thereof;
- from 0.2 to 0.6 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one 1,2-C2-C6-alkanediol, 1,3-C2-C6alkanediol or 1,4-C2-C6alkanediol, of which from 0 to 0.05 mol of one hydroxyl group may be esterified with a monocarboxylic acid, where the C2-C6alkanediol may be uninterrupted or interrupted by —O—, with the proviso that no carbon atom of the C2-C6alkanediol is bonded to more than one oxygen atom;
- optionally from 0 to 0.1 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of one or more amino acids;
- optionally from 0 to 0.1 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of one or more monofunctional components selected from the group consisting of monoalcohols, primary monoamines and monoacids each containing from 1 to 18 carbon atoms;
- and
- from 0.001 to 0.15 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one colourant which has at least two chlorosulphonyl groups, at least two 4-chloro-3-oxo-2-azabutyl groups, a 3,5-dicarboxyphenyl group or both a reactive chlorine or bromine and a carboxyl, hydroxyl or amino group bonded to the chromophore of the colourant by an aliphatic chain containing at least 4 members selected from the group consisting of methylene, oxy, carbonyl, sulpho and amino, with the proviso that at least two of these substituents must be removed from one another to such an extent that they are not condensable with one another to form a fewer than 10-membered intramolecular ring;
- with the proviso that the molar ratio of the total amount of all hydroxyl and primary amino groups or latent forms thereof to the total amount of all carboxyl and sulpho groups is from 5:4 to 4:5.
5 more elements
A process for preparing a copolycondensate, wherein
- at least one 1,2-C4-C8cycloalkanedicarboxylic acid, 1,3-C4-C8cycloalkanedicarboxylic acid or 1,4-C4-C8cycloalkanedicarboxylic acid, or an ester, anhydride or acid chloride thereof;
- from 0.3 to 0.8 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one 1,2-C6-C12-cycloalkanediamine, 1,3-C6-C12cycloalkanediamine or 1,4-C6-C12cycloalkanediamine, or of a latent form thereof;
- from 0.2 to 0.6 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one 1,2-C2-C6-alkanediol, 1,3-C2-C6alkanediol or 1,4-C2-C6alkanediol, of which from 0 to 0.05 mol of one hydroxyl group may be esterified with a monocarboxylic acid, where the C2-C6alkanediol may be uninterrupted or interrupted by —O—, with the proviso that no carbon atom of the C2-C6alkanediol is bonded to more than one oxygen atom;
- optionally from 0 to 0.1 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of one or more amino acids;
- optionally from 0 to 0.1 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of one or more monofunctional components selected from the group consisting of monoalcohols, primary monoamines and monoacids each containing from 1 to 18 carbon atoms;
- and
- from 0.001 to 0.15 mol, based on 1 mol of C4-C8cycloalkanedicarboxylic acid, of at least one colourant which has at least two chlorosulphonyl groups, at least two 4-chloro-3-oxo-2-azabutyl groups, a 3,5-dicarboxyphenyl group or both a reactive chlorine or bromine and a carboxyl, hydroxyl or amino group bonded to the chromophore of the colourant by an aliphatic chain containing at least 4 members selected from the group consisting of methylene, oxy, carbonyl, sulpho and amino, with the proviso that at least two of these substituents must be removed from one another to such an extent that they are not condensable with one another to form a fewer than 10-membered intramolecular ring;
- with the proviso that the molar ratio of the total amount of all hydroxyl and primary amino groups or latent forms thereof to the total amount of all carboxyl and sulpho groups is from 5:4 to 4:5;
- are heated to approximately 50 to 300° C. over 1 s to 100 hours at a pressure of 102 to 107 Pa in the presence of an acidic catalyst.
6 more elements
Dependencies are inferred from the claim text.