Low viscosity allophanates containing actinically curable groups
View Patent ↗The present invention relates to a process for preparing radiation-curing binders containing allophanate groups by reacting at temperatures of ≦130° C. A) one or more compounds containing uretdione groups with B) one or more OH-functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation, (radiation-curing groups), C) optionally NCO-reactive compounds other than B), in the presence of D) a catalyst containing at least one tetrasubstituted ammonium or phosphonium salt of an aliphatic or cycloaliphatic carboxylic acid, to form allophanate groups by opening the uretdione ring. The present invention also relates to the binders obtained by the process of the invention.
1. A process for preparing a radiation-curing binder containing allophanate groups which comprises reacting at a temperature of 40 to 100° C.,
A) one or more compounds containing uretdione groups with
B) one or more OH-functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO-reactive compounds other than B),
in the presence of
D) a catalyst selected from the group consisting of tetrabutylaminonium 2-ethylhexanoate, tetrabutylammonium pivalate, choline 2-ethylhexanoate, choline pivalate, methylcholine 2-ethylhexanoate and methylcholine pivalate,
to form allophanate groups by opening the uretdione ring.
2. The process of claim 1 wherein said compounds containing uretdione groups are prepared from hexamethylene diisocyanate.
3. The process of claim 1 wherein component B) comprises 2-hydroxyethyl acrylate and/or 4-hydroxybutyl acrylate.
4. The process of claim 2 wherein component B) comprises 2-hydroxyethyl acrylate and/or 4-hydroxybutyl acrylate.
5. A radiation-curing binder containing allophanate groups which is prepared by a process comprising reacting at a temperature of 40 to 100° C.,
A) one or more compounds containing uretdione groups with
B) one or more OH-functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO-reactive compounds other than B),
in the presence of
D) a catalyst selected from the group consisting of tetrabutylammonium 2-ethylhexanoate, tetrabutylammonium pivalate, choline 2-ethylhexanoate, choline pivalate, methylcholine 2-ethylhexanoate and methylcholine pivalate,
to form allophanate groups by opening the uretdione ring.
6. The radiation-curing binder of claim 5 wherein said compounds containing uretdione groups are prepared from hexamethylene diisocyanate.
7. The radiation-curing binder of claim 5 wherein component B) comprises 2-hydroxyethyl acrylate and/or 4-hydroxybutyl acrylate.
8. The radiation-curing binder of claim 6 wherein component B) comprises 2-hydroxyethyl acrylate and/or 4-hydroxybutyl acrylate.
9. A coating composition comprising
a) one or more of the radiation-curing binders containing allophanate groups of claim 5 ,
b) optionally one or more polyisocyanates containing free or blocked isocyanate groups, which are free from groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
c) optionally compounds other than a), which contain groups which 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,
e) one or more initiators, and
f) optionally solvents.
10. A substrate coated with a coating obtained from the radiation-curing binder containing allophanate groups of claim 5 .
11. A process for preparing a radiation-curing binder containing allophanate groups, wherein the radiation-curing binder has a number average molecular weight from 600 to 1500 g/mol, which comprises reacting at a temperature of 40 to 100° C.
A) one or more compounds containing uretdione groups with
B) one or more OH functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO reactive compounds other than B),
in the presence of
D) a catalyst selected from the group consisting of tetrabutylammonium 2-ethylhexanoate, tetrabutylammonium pivalate, choline 2-ethylhexanoate, choline pivalate, methylcholine 2-ethylhexanoate and methylcholine pivalate,
to form allophanate groups by opening the uretdione ring.
12. A radiation curing binder containing allophanate groups, wherein the radiation-curing binder has a number average molecular weight from 600 to 1500 g/mol, which is prepared by a process comprising reacting at a temperature of 40 to 100° C.
A) one or more compounds containing uretdione groups with
B) one or more OH functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO reactive compounds other than B),
in the presence of
D) a catalyst selected from the group consisting of tetrabutylammonium 2-ethylhexanoate, tetrabutylammonium pivalate, choline 2-ethylhexanoate, choline pivalate, methylcholine 2-ethylhexanoate and methylcholine pivalate,
to form allophanate groups by opening the uretdione ring.
13. The process of claim 11 , wherein the radiation-curing binder has a number average molecular weight of from 750 to 1500 g/mol.
14. The radiation curing binder of claim 12 , wherein the radiation-curing binder has a number average molecular weight of from 750 to 1500 g/mol.
15. A process for preparing a radiation-curing binder containing allophanate groups which comprises reacting at a temperature of 40 to 100° C.
A) one or more compounds containing uretdione groups with
B) one or more OH functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO reactive compounds other than B),
in the presence of
D) a catalyst comprising choline 2-ethylhexanoate,
to form allophanate groups by opening the uretdione ring.
16. A radiation-curing binder containing allophanate groups which is prepared by a process comprising reacting at a temperature of 40 to 100° C.
A) one or more compounds containing uretdione groups with
B) one or more OH functional compounds which contain groups which react, with polymerization, with ethylenically unsaturated compounds on exposure to actinic radiation,
C) optionally NCO reactive compounds other than B),
in the presence of
D) a catalyst comprising choline 2-ethylhexanoate,
to form allophanate groups by opening the uretdione ring.