Process for preparing low-viscosity allophanates containing actinically curable groups
View Patent ↗The present invention provides a process for preparing radiation-curing allophanates having residual monomer contents of less than 0.5% by weight and an NCO content of less than 1% by weight, wherein (A) compounds containing isocyanate groups, (B) hydroxy-functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation (radiation-curing groups) and (C) optionally further compounds containing NCO-reactive groups, also optionally in the presence of a catalyst, are used to form NCO-group-containing urethanes having radiation-curing groups, which are subsequently reacted, without further addition of compounds containing isocyanate groups, in the presence of an allophanatization catalyst, the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and, where used, C) being 1.45:1.0 to 1.1:1.0.
1. Process for preparing radiation-curing allophanates having residual monomer content of less than 0.5% by weight and an NCO content of less than 1% by weight, wherein
A) compounds containing isocyanate groups,
B) hydroxy-functional compounds which contain at least one group selected from vinyl ethers, acrylates and methacrylates which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation and
C) optionally further compounds containing NCO-reactive groups
D) optionally in the presence of a catalyst
are used to form NCO-group-containing urethanes having radiation-curing groups, which are subsequently reacted, without further addition of compounds containing isocyanate groups, in the presence
E) of an allophanatization catalyst,
the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and, where used, C) being 1.45:1.0 to 1.1:1.0, and
wherein no distillation is required to yield the radiation-curing allophanates having a residual monomer content of less than 0.5% by weight and an NCO content of less than 1% by weight.
2. Process for preparing radiation-curing allophanates according to claim 1 , wherein in component A) hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI) and/or 4,4′-diisocyanatodicyclohexylmethane are used.
3. Process for preparing radiation-curing allophanates according to claim 1 , wherein in component B) hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate and/or hydroxybutyl (meth)acrylate are used.
4. Process for preparing radiation-curing allophanates according to claim 1 , wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and, where used, C) is 1.35:1.0 to 1.3:1.0.
5. Process for preparing radiation-curing allophanates according to claim 1 , wherein catalyst E) is added at a rate of 200-600 ppm/h.
6. Process for preparing radiation-curing allophanates according to claim 1 , wherein the allophanatization is carried out until the end product has an NCO content of below 0.1% by weight.
7. Process for preparing radiation-curing allophanates comprising reacting, optionally in the presence of a catalyst,
A) compounds containing isocyanate groups,
B) hydroxy-functional compounds which contain at least one group selected from vinyl ethers, acrylates and methacrylates which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation and
C) optionally further compounds containing NCO-reactive groups to form NCO-group-containing urethanes having radiation-curing groups, and subsequently reacting the NCO-group containing urethanes, without further addition of compounds containing isocyanate groups, in the presence
E) of an allophanatization catalyst,
to form the radiation-curing allophanates,
wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and, where used, C) is from 1.45:1.0 to 1.1:1.0,
wherein the radiation-curing allophanates have an NCO content of less than 1% by weight and have a residual monomer content of less than 0.5% by weight,
with the proviso that no distillation step is performed.
8. Process for preparing radiation-curing allophanates according to claim 7 , wherein in component A) hexamethylene diisocyanate (HDI), isophorone diisocyanate (IPDI) and/or 4,4′-diisocyanatodicyclohexylmethane are used.
9. Process for preparing radiation-curing allophanates according to claim 7 , wherein in component B) hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate and/or hydroxybutyl (meth)acrylate are used.
10. Process for preparing radiation-curing allophanates according to claim 7 , wherein the ratio of NCO groups of the compounds from A) to the OH groups of the compounds from B) and, where used, C) is 1.35:1.0 to 1.3:1.0.
11. Process for preparing radiation-curing allophanates according to claim 7 , wherein catalyst E) is added at a rate of 200-600 ppm/h.
12. Process for preparing radiation-curing allophanates according to claim 7 , wherein the allophanatization is carried out until the end product has an NCO content of below 0.1% by weight.