Polymers of a compound comprising a monothiocarbonate group and an ethylenically unsaturated group

Patent metadata

Field	Value
Publication number	US-12060458-B2
Application number	US-201917270187-A
Country	US
Kind code	B2
Filing date	Aug 19, 2019
Priority date	Aug 28, 2018
Publication date	Aug 13, 2024
Grant date	Aug 13, 2024

Abstract

A polymer obtainable by reacting a compound A) comprising at least one five-membered cyclic monothiocarbonate group and at least one polymerizable, ethylenically unsaturated group, a compound B) comprising at least one amino group, selected from primary or secondary amino groups, optionally a compound C) which is different from compound A) and comprises at least one five-membered cyclic monothiocarbonate group, and optionally a compound D) which is different from compound A) and comprises at least one functional group that reacts with a group —SH.

First claim

The invention claimed is:

1. A polymer, obtained by reacting:
a compound A) comprising one to three five-membered cyclic monothiocarbonate groups and at least one polymerizable, ethylenically unsaturated group,
a compound B) comprising at least one amino group, selected from the group consisting of primary and secondary amino groups,
optionally, a compound C) which is different from compound A) and comprises at least one five-membered cyclic monothiocarbonate group, and
optionally, a compound D) which is different from compound A) and comprises at least one functional group that reacts with a group —SH wherein the five-membered cyclic monothiocarbonate group of compound A) is opened by the reaction with the amino groups of compound B) to form an adduct comprising a SH group and a polymerizable, ethylenically unsaturated group, followed by a reaction of the SH group with the polymerizable, ethylenically unsaturated group.

2. The polymer according to claim 1 , wherein compound A) comprises one five-membered cyclic monothiocarbonate group and one polymerizable, ethylenically unsaturated group.

3. The polymer according to claim 1 , wherein the polymerizable, ethylenically unsaturated group is a vinyl group or an acrylic or methacrylic group.

4. The polymer according to claim 1 , wherein compound A) is a compound of formula I

wherein one of R 1 to R 4 represents an organic group comprising a vinyl group or a (meth)acrylic group and the remaining three of R 1 to R 4 represent hydrogen or an organic group with at maximum 20 carbon atoms.

5. The polymer according to claim 1 , wherein compound A) is 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-on or 5-(acryloyloxy)methyl-1,3-oxathiolane-2-on.

6. The polymer according to claim 1 , wherein compound B) comprises one to five amino groups.

7. The polymer according to claim 1 , wherein compound D) is present, wherein the functional group of compound D) that reacts with —SH is selected from the group consisting of polymerizable, ethylenically unsaturated groups and epoxy groups.

8. The polymer according to claim 1 , wherein the polymer comprises at least 60% by weight of compounds A) and B).

9. The polymer according to claim 1 , wherein compounds A), B) and optionally C) and D) are used in an amount to give a molar ratio of 0.8 to 1.2 mol of groups reactive with —SH to 1 mol of —SH groups.

10. A two component curable system, consisting of:
a first component comprising a compound A) comprising one to three five-membered cyclic monothiocarbonate groups and at least one polymerizable, ethylenically unsaturated group,
optionally, a compound C) which is different from compound A) and comprises at least one five-membered cyclic monothiocarbonate group, and
optionally, a compound D) which is different from compound A) and comprises at least one functional group that reacts with a group —SH, and
a second component comprising a compound B) comprising at least one amino group, selected from the group consisting of primary and secondary amino groups wherein when compound A) and compound B) are combined, the five-membered cyclic monothiocarbonate group of compound A) is opened by the reaction with the amino groups of compound B) to form an adduct comprising a SH group and a polymerizable, ethylenically unsaturated group, followed by a reaction of the SH group with the polymerizable, ethylenically unsaturated group.

11. A process for the manufacturing of a polymer, the process comprising:
reacting
a compound A) comprising one to three five-membered cyclic monothiocarbonate groups and at least one polymerizable, ethylenically unsaturated group,
a compound B) comprising at least one amino group, selected from the group consisting of primary and secondary amino groups,
optionally, a compound C) which is different from compound A) and comprises at least one five-membered cyclic monothiocarbonate group, and
optionally, a compound D) which is different from compound A) and comprises at least one functional group that reacts with a group —SH,
wherein compound B) is used in an amount to transfer at least 10 mol % of the monothiocarbonate groups of compounds A) and optionally C) into —SH group, and wherein the five-membered cyclic monothiocarbonate group of compound A) is opened by the reaction with the amino groups of compound B) to form an adduct comprising a SH group and a polymerizable, ethylenically unsaturated group, followed by a reaction of the SH group with the polymerizable, ethylenically unsaturated group.

12. The polymer according to claim 1 , wherein compound A) comprises 1 to 3 cyclic monothiocarbonate groups and 1 to 3 polymerizable, ethylenically unsaturated groups.

13. The two-component curable system according to claim 10 , wherein compound A) comprises 1 to 3 cyclic monothiocarbonate groups and 1 to 3 polymerizable, ethylenically unsaturated groups.

14. The process according to claim 11 , wherein compound A) comprises 1 to 3 cyclic monothiocarbonate groups and 1 to 3 polymerizable, ethylenically unsaturated groups.

15. The two-component curable system according to claim 10 , wherein compound B) is used in an amount to transfer at least 10 mol % of the monothiocarbonate groups of compounds A) and optionally C) into —SH groups.

16. The polymer according to claim 1 , wherein compound C) is present.

17. The polymer according to claim 1 , wherein compound D) is present.

18. The two-component curable system according to claim 10 , wherein compound C) is present.

19. The two-component curable system according to claim 10 , wherein compound D) is present.

20. The polymer according to claim 1 , wherein compound B) is used in an amount to transfer at least 10 mol % of the monothiocarbonate groups of compounds A) and optionally C) into —SH groups.

Assignees

• Basf Se

Inventors

• Thiel Indre
• Jegelka Markus
• Rudolf Peter

Classifications

• C08G71/04 Primary

  Polyurethanes · CPC title

• C08G75/28 Primary

  Polythiocarbonates · CPC title

• C08G75/02

  Polythioethers · CPC title