Process for preparing low-viscosity allophanates containing actinically curable groups

Patent metadata

Field	Value
Publication number	US-9988485-B2
Application number	US-201514757650-A
Country	US
Kind code	B2
Filing date	Dec 23, 2015
Priority date	Oct 7, 2004
Publication date	Jun 5, 2018
Grant date	Jun 5, 2018

Abstract

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.

First claim

The invention claimed is:

1. A radiation-curing allophanate having a residual monomer content of less than 0.5% by weight, obtained by a process comprising
forming an NCO-group-containing urethane having radiation curing groups, by reacting, optionally in the presence of a catalyst,
A) one or more compounds containing isocyanate groups,
B) one or more 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 one or more compounds containing NCO-reactive groups selected from the group consisting of polyether polyols, polyester polyols, polycarbonate polyols, and polyhydric alcohols; and

subsequently reacting the NCO-group-containing urethane, without further addition of compounds containing isocyanate groups, in the presence of an allophanatization catalyst, until the end product has an NCO content of 0.0-0.05% by weight,
wherein the ratio of NCO groups of the compounds A) to the OH groups of the one or more compounds B) and C) is from 1.45:1.0 to 1.1:1.0.

2. The radiation-curing allophanate according to claim 1 , with the proviso that no distillation is performed in the process.

3. The radiation-curing allophanate according to claim 1 , wherein A) comprises hexamethylene diisocyanate, isophorone diisocyanate or 4,4′-diisocyanatodicyclohexylmethane.

4. The radiation-curing allophanate according to claim 1 , wherein B) comprises hydroxyethyl (meth)acrylate, hydroxypropyl (meth)acrylate or hydroxybutyl (meth)acrylate.

5. The radiation-curing allophanate according to claim 1 , wherein the ratio of NCO groups of the one or more compounds A) to the OH groups of the one or more compounds B) and compounds C) is 1.35:1.0 to 1.3:1.0.

6. The radiation-curing allophanate according to claim 1 , wherein the allophanatization catalyst is added at a rate of 200-600 ppm/h.

7. The radiation-curing allophanate according to claim 1 , wherein no distillation is required to yield the radiation-curing allophanate having a residual monomer content of less than 0.5% by weight and an NCO content of 0.0-0.05% by weight.

8. A coating composition comprising
a) the radiation-curing allophanate according to claim 1 ,
b) optionally one or more polyisocyanates containing free or blocked isocyanate groups, which are free from groups that react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
c) optionally other compounds, different from a), which contain groups that react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation, and optionally contain free or blocked NCO groups,
d) optionally one or more isocyanate-reactive compounds containing active hydrogen,
e) initiators,
f) optionally solvents, and
g) optionally auxiliaries and additives.

9. A substrate coated with the coating composition according to claim 8 .

10. The radiation-curing allophanate according to claim 1 , wherein A) comprises hexamethylene diisocyanate.

11. The radiation-curing allophanate according to claim 1 , wherein A) comprises isophorone diisocyanate.

12. The radiation-curing allophanate according to claim 1 , wherein A) comprises 4,4′-diisocyanatodicyclohexylmethane.

13. The radiation-curing allophanate according to claim 1 , wherein B) comprises hydroxyethyl (meth)acrylate.

14. The radiation-curing allophanate according to claim 1 , wherein B) comprises hydroxypropyl (meth)acrylate.

15. The radiation-curing allophanate according to claim 1 , wherein B) comprises hydroxybutyl (meth)acrylate.

Assignees

• Allnex Ip S Ar L
• Allnex Netherlands Bv

Inventors

• Ludewig Michael
• Weikard Jan

Classifications

• C09D175/16

  having terminal carbon-to-carbon unsaturated bonds · CPC title

• C08G18/6715

  Unsaturated monofunctional alcohols or amines · CPC title

• C08G18/73 Primary

  acyclic · CPC title

• C07C269/06

  by reactions not involving the formation of carbamate groups · CPC title

• C08G18/2835

  having less than 5 ether groups · CPC title