Ionically hydrophilized polyisocyanates, water content
View Patent ↗The invention relates to a process for producing polyisocyanates containing sulfonate groups, the products obtainable or obtained by said process and also to the use thereof as starting component for producing polyurethane plastics. The invention further relates to coating compositions comprising polyisocyanates containing sulfonate groups and also to the substrates coated with said coating compositions.
1. A process for producing polyisocyanates containing sulfonate groups, comprising a reaction of
A) at least one polyisocyanate component with
B) at least one aminosulfonic acid comprising at least one amino group and at least one sulfonic acid group, and optionally
C) at least one non-ionic hydrophilic or hydrophobic organic compound comprising at least one group reactive to isocyanates, in the presence of
D) at least one tertiary amine and optionally in the presence of
E) other auxiliaries and additives
characterized in that
the aminosulfonic acid B) has a water content of 0.05 to 1.5% by weight.
2. The process as claimed in claim 1 , characterized in that the polyisocyanate component A) are polyisocyanates having a uretdione, isocyanurate, allophanate, biuret, iminooxadiazinedione and/or oxadiazinetrione structure having exclusively aliphatically and/or cycloaliphatically bonded isocyanate groups.
3. The process as claimed in claim 1 , characterized in that the aminosulfonic acid B) are substituted aromatic sulfonic acids which have up to three sulfonic acid groups and comprises up to three primary or secondary amino groups, wherein the positions on the aromatic ring in the position ortho to the amino group are unsubstituted.
4. The process as claimed in claim 3 , characterized in that the aminosulfonic acid component B) is 4-aminotoluene-2-sulfonic acid, 5-aminotoluene-2-sulfonic acid and/or 2-aminonaphthalene-4-sulfonic acid.
5. The process as claimed in claim 1 , characterized in that the aminosulfonic acid component B) is an amino-functional sulfonic acid of the general formula (II)
in which R 4 and R 5 are each independently identical or different radicals and are hydrogen or saturated or unsaturated, linear or branched, aliphatic or cycloaliphatic or aromatic organic radicals having 1 to 18 carbon atoms, which are substituted or unsubstituted and/or comprise heteroatoms in the chain, wherein R 4 and R 5 , also in combination with each other and optionally with one further nitrogen atom or one oxygen atom, may form cycloaliphatic or heterocyclic rings having 3 to 8 carbon atoms, which may optionally be further substituted, and R 6 is a linear or branched aliphatic radical having 2 to 6 carbon atoms.
6. The process as claimed in claim 5 , characterized in that the aminosulfonic acid component B) is 2-isopropylaminoethane-1-sulfonic acid, 3-isopropylaminopropane-1-sulfonic acid, 4-isopropylaminobutane-1-sulfonic acid, 2-cyclohexylaminoethane-1-sulfonic acid, 3-cyclohexylaminopropane-1-sulfonic acid and/or 4-cyclohexylaminobutane-1-sulfonic acid.
7. The process as claimed in claim 1 , characterized in that the aminosulfonic acid component B) is used in an amount of 0.3 to 25.0% by weight, based on the total weight of the components A) and B).
8. The process as claimed in claim 1 , characterized in that the non-ionic hydrophilic or hydrophobic organic compounds C) are pure polyethylene oxide polyether alcohols and/or mixed polyalkylene oxide polyether alcohols, the alkylene oxide units of which consist of ethylene oxide units to an extent of at least 70 mol %, and/or aliphatic alcohols or fatty acid ester alcohols, which comprise in each case at least 8 carbon atoms.
9. The process as claimed in claim 1 , characterized in that the tertiary amines D) are N,N-dimethylbutylamine, N,N-dimethyl-2-ethylhexylamine, N,N-diethylmethylamine, N,N-diisopropylethylamine, N,N-diisopropyl-2-ethylhexylamine, N,N-dimethylcyclohexylamine, N,N-dicyclohexylmethylamine, N-methylpyrrolidine, N-methylpiperidine, N-ethylpiperidine, N-methylmorpholine, N-ethylmorpholine, N-isobutylmorpholines, and mixtures thereof.
10. The process as claimed in claim 1 , characterized in that the auxiliaries and additives E) are antioxidants and/or catalysts.
11. The process as claimed in claim 1 , characterized in that the aminosulfonic acids B) have a water content of 0.1 to 1.0% by weight, or 0.15 to 0.9% by weight, or 0.2 to 0.6% by weight.
12. The polyisocyanates containing sulfonate groups obtained by the process as claimed in claim 1 .
13. A coating composition comprising polyisocyanates containing sulfonate groups as claimed in claim 12 .