Radiation-curing binders and a process for their preparation
View Patent ↗The invention relates to a process for preparing binders which contain 1) allophanate groups, 2) groups that react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation (radiation-curing groups) and 3) optionally NCO-reactive groups, by reacting at temperatures ≦130° C. A) one or more NCO-functional compounds containing uretdione groups with B) one or more compounds that contain isocyanate-reactive groups and groups that react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation (radiation-curing groups), and then C) with one or more saturated, hydroxyl-containing compounds other than B), at least one of these compounds having an OH functionality of ≧2, in the presence of D) a catalyst containing one or more ammonium salts or phosphonium salts of aliphatic or cycloaliphatic carboxylic acids, the reaction with compounds C) taking place at least proportionally with the formation of allophanate groups. The present invention also relates to the binders obtained by the process of the invention.
1. A binder which contains 1) allophanate groups, 2) groups that react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation (radiation-curing groups) and 3) optionally NCO-reactive groups, which is prepared by a process comprising reacting at temperatures ≦130° C.
A) one or more NCO-functional compounds containing uretdione groups with
B) one or more compounds that contain isocyanate-reactive groups and contain groups that react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation (radiation-curing groups), and then with
C) one or more saturated, hydroxyl-containing compounds other than B),
at least one of these compounds having an OH functionality of ≧2, in the presence of
D) a catalyst containing one or more ammonium salts or phosphonium salts of aliphatic or cycloaliphatic carboxylic acids,
the reaction with compounds C) taking place at least proportionally with the formation of allophanate groups.
2. The binder of claim 1 wherein said compounds containing uretdione groups are prepared from hexamethylene diisocyanate.
3. The binder of claim 2 wherein component B) comprises a member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, polyethylene oxide mono(meth)acrylate, polypropylene oxide mono(meth)acrylate and the reaction product of acrylic acid with glycidyl methacrylate.
4. The binder of claim 3 wherein component C) comprises a member selected from the group consisting of monomeric diols, monomeric triols, polyethers and polyacetones derived therefrom having a number average molecular weight of below 1000 g/mol.
5. The binder of claim 2 wherein component C) comprises a member selected from the group consisting of monomeric diols, monomeric triols, polyethers and polyacetones derived therefrom having a number average molecular weight of below 1000 g/mol.
6. The binder of claim 1 wherein component B) comprises a member selected from the group consisting of 2-hydroxyethyl acrylate, 2-hydroxypropyl acrylate, 4-hydroxybutyl acrylate, polyethylene oxide mono(meth)acrylate, polypropylene oxide mono(meth)acrylate and the reaction product of acrylic acid with glycidyl methacrylate.
7. The binder of claim 1 wherein component C) comprises a member selected from the group consisting of monomeric diols, monomeric triols, polyethers and polyacetones derived therefrom having a number average molecular weight of below 1000 g/mol.
8. A coating composition comprising
a) one or more of the binders of claim 1 ,
b) optionally one or more polyisocyanates which contain free or blocked isocyanate groups and optionally contain groups which react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation,
c) optionally compounds other than the binders a) which contain groups which react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation and optionally contain NCO-reactive groups,
d) optionally one or more isocyanate-reactive compounds which are free from groups which react with ethylenically unsaturated compounds with polymerization on exposure to actinic radiation, and
e) one or more initiators.
9. A substrate coated with a coating obtained from the radiation-string binder containing allophanate groups of claim 1 .