Process for the preparation of low-viscosity, water-emulsifiable allophanates with radiation-curable groups
View Patent ↗The present invention relates to a process for the preparation of low-viscosity polyisocyanate reaction products which contain allophanate groups, can be readily emulsified in water and contain activated groups which react, by polymerization, with ethylenically unsaturated compounds under the action of actinic radiation. The present invention furthermore relates to the products which can be prepared by the process according to the invention and their use.
1. A process for preparing a water-emulsifiable, radiation-curing allophanate having residual monomer contents of less than 0.5 weight % and an NCO content of less than 1 weight %, comprising forming urethanes which contain NCO groups and have radiation-curing groups from
A) at least one compound containing isocyanate groups,
B) at least one hydroxy-functional compound which has groups which react, by polymerization, with ethylenically unsaturated compounds under the action of actinic radiation (radiation-curing groups),
C) at least one polyoxyalkylene mono-ol,
E) optionally in the presence of a catalyst, and subsequently reacting said urethanes which contain NCO groups and have radiation-curing groups, without further addition of compounds containing isocyanate groups, in the presence of
F) an allophanation catalyst, and
G) optionally a tertiary amine,
wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and C) is 1.80:1.0 to 1.46:1.0.
2. The process of claim 1 , wherein at least one compound which differs from B) and/or C) and has NCO-reactive groups is employed as component D), wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B), C) and D) is 1.80:1.0 to 1.46:1.0.
3. The process of claim 1 , wherein hexamethylene-diisocyanate (HDI), isophorone-diisocyanate (IPDI), and/or 4,4′-diisocyanatodicyclohexylmethane are employed in component A).
4. The process of claim 1 , wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B), C) and D) is 1.7:1.0 to 1.47:1.0.
5. The process of claim 1 , wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B), C) and D) is 1.65:1.0 to 1.48:1.0.
6. The process of claim 1 , wherein polyoxyalkylene mono-ols which contain a content of from 30 to 100 weight % of units which are derived from ethylene oxide are employed in C).
7. The process of claim 1 , wherein hydroxyethyl (meth)acrylate and/or hydroxypropyl (meth)acrylate are employed in component B).
8. The process of claim 1 , wherein the allophanation is carried out until the end product has an NCO content of less than 0.1 weight %.
9. The process of claim 1 , wherein component A) is employed in amounts of from 20 to 60 weight %, component B) in amounts of from 25 to 50 weight %, component C) in amounts of from 10 to 35 weight %, component D) in amounts of from 0 to 40 weight %, component E) in amounts of from 0 to 5 weight %, component F) in amounts of from 0.001 to 5 weight % and component G) in amounts of from 0 to 5 weight %, with the proviso that the sum of the weight % of components A) to G) is 100.
10. The process of claim 1 , wherein the urethanation of components A) to D) is optionally carried out in the presence of E), according to determination of the NCO content an NCO value is reached which deviates from the theoretical % NCO content by up to 1.5 weight % NCO (absolute), and the allophanation is subsequently carried out by addition of component E) and optionally F), without further addition of compounds containing isocyanate groups.