Process for the manufacturing of a polymer with urethane groups

Patent metadata

Field	Value
Publication number	US-11958823-B2
Application number	US-201816639339-A
Country	US
Kind code	B2
Filing date	Aug 7, 2018
Priority date	Aug 17, 2017
Publication date	Apr 16, 2024
Grant date	Apr 16, 2024

Abstract

Object of the invention is a process for the manufacturing of a polymer with urethane groups, wherein in a first alternative A) a five-membered cyclic monothiocarbonate B) a compound with at least two amino groups, selected from primary or secondary amino groups, and C) a compound which at least two functional groups that react with a group —SH or, in case of a carbon-carbon triple bond as functional group that react with a group —SH, a compound with at least one carbon-carbon triple bond are reacted or wherein in a second alternative A) a five-membered cyclic monothiocarbonate and D) a compound with at least one primary or secondary amino group and at least one functional group that reacts with a group —SH.

First claim

The invention claimed is:

1. A process for manufacturing a polymer comprising urethane groups, the process comprising:
in a first alternative, reacting
A) a five-membered cyclic monothiocarbonate, and
B) a compound comprising at least two amino groups, selected from primary or secondary amino groups, and
C) a compound comprising at least one carbon-carbon triple bond or at least two functional groups that react with a —SH group; or

in a second alternative, reacting
A) a five-membered cyclic monothiocarbonate, and
D) a compound with at least one primary or secondary amnmo group and at least one functional group that reacts with a group —SH,

wherein
A) is a monothiocarbonate of formula I

wherein R 1 , R 2 , R 3 , and R 4 each independently represent hydrogen or an organic group comprising up to 50 carbon atoms; and
R 2 and R 4 and the two carbon atoms to which R 2 and R 4 are bonded optionally form a five to ten membered carbon ring,
where in the first alternative when the at least two functional groups of compound C) that react with the —SH group are present they are selected from the group consisting of non-aromatic, ethylenically unsaturated groups, isocyanate groups, groups with a non-aromatic carbon-nitrogen double bond, carbonyl groups and halides, and
where in the second alternative, the compound D) includes as the at least one functional group a functional group selected from the group consisting of non-aromatic, ethylenically unsaturated groups; a carbon-carbon triple bond; isocyanate groups; groups with a non-aromatic carbon-nitrogen double bond; carbonyl groups; and halides.

2. The process of claim 1 , comprising the first alternative, wherein B) is a compound comprising at least two aliphatic or cycloaliphatic primary amino groups.

3. The process of claim 1 , comprising the first alternative, wherein the at least two functional groups of compound C) that react with the —SH group are present and are selected from non-aromatic, ethylenically unsaturated groups.

4. The process of claim 1 , comprising the first alternative, wherein the at least two functional groups of compound C) that react with the —SH group are present and are methacryl groups.

5. The process of claim 1 , comprising the first alternative, wherein the reacting of the first alternative comprises:
reacting A), B), and C) simultaneously; or
reacting A) with B), to obtain an intermediate, and then reacting the intermediate with C).

6. The process of claim 1 , comprising the second alternative, wherein D) is a compound comprising one primary amino group and one non-aromatic carbon-carbon double bond or triple bond.

7. A polymer comprising urethane groups, wherein the polymer comprising the urethane groups is produced according to the process of claim 1 .

8. A curable composition, comprising:
A) a five-membered cyclic monothiocarbonate,
B) a compound comprising at least two amino groups, selected from primary or secondary amino groups, and
C) a compound comprising at least one carbon-carbon triple bond or at least two functional groups that react with a —SH group; selected from the group consisting of non-aromatic, ethylenically unsaturated groups, isocyanate groups, groups with a non-aromatic carbon-nitrogen double bond, carbonyl groups and halides, or

a reaction product of A) and B), and C),
wherein
A) is a monothiocarbonate of formula I

wherein R 1 , R 2 , R 3 , and R 4 each independently represent hydrogen or an organic group comprising up to 50 carbon atoms, and
R 2 and R 4 and the two carbon atoms to which R 2 and R 4 are bonded optionally form a five to ten membered carbon ring.

9. A two-component curable system, comprising; a first component of A) and C) and a second component B), wherein
A) is a five-membered cyclic monothiocarbonate,
B) is a compound comprising at least two amino groups, selected from primary or secondary amino groups, and
C) is a compound comprising at least one carbon-carbon triple bond or at least two functional groups that react with a —SH group, selected from the group consisting of non-aromatic, ethylenically unsaturated groups, isocyanate groups, groups with a non-aromatic carbon-nitrogen double bond, carbonyl groups and halides

wherein
A) is a monothiocarbonate of formula I

wherein R 1 , R 2 , R 3 , and R 4 each independently represent hydrogen or an organic group comprising up to 50 carbon atoms, and
R 2 and R 4 and the two carbon atoms to which R 2 and R 4 are bonded optionally form a five to ten membered carbon ring.

10. A monothiocarbonate, which satisfies the following formula I,

wherein R 2 , R 3 , and R 4 each represent hydrogen and R 1 is CH 2 —O—R 5 or —CH 2 —O—C(═O)—R 6 , wherein R 5 and R 6 are each independently a C1 to C14 alkyl group.

11. The process of claim 1 , wherein R 1 is selected from the group consisting of —CH 2 —O—R 5 , —CH 2 —O—C(C═O)—R 6 , and —CH 2 —NR 7 R 8 , and R 5 to R 8 is an organic group with up to 30 carbon atoms.

12. The process of claim 1 , wherein R 1 is selected from the group consisting of CH 2 —O—R 5 and —CH 2 —O—C(═O)—R 6 , wherein R 5 and R 6 are each independently a C 1 to C 14 alkyl group.

13. A polymer according to claim 7 , wherein R 1 is selected from the group consisting of CH 2 —O—R 5 and —CH 2 —O—C(═O)—R 6 , wherein R 5 and R 6 are each independently a C 1 to C 14 alkyl group.

14. A curable composition according to claim 8 , wherein R 1 is selected from the group consisting of CH 2 —O—R 5 and —CH 2 —O—C(═O)—R 6 , wherein R 5 and R 6 are each independently a C 1 to C 14 alkyl group.

15. A two-component curable system according to claim 9 , wherein R 1 is selected from the group consisting of CH 2 —O—R 5 and —CH 2 —O—C(═O)—R 6 , wherein R 5 and R 6 are each independently a C 1 to C 14 alkyl group.

16. The process of claim 1 , comprising the first alternative, wherein the compound C) includes at least two functional groups that react with the —SH group that are selected from the group consisting of non-aromatic, ethylenically unsaturated groups; isocyanate groups; groups with a non-aromatic carbon-nitrogen double bond; carbonyl groups; and halides.

17. The process of claim 1 , comprising the second alternative, wherein the compound D) includes as the at least one function group a functional group selected from the group consisting of non-aromatic, ethylenically unsaturated groups; isocyanate groups; groups with a non-aromatic carbon-nitrogen double bond; carbonyl groups; and halides.

18. A curable composition according to claim 8 , comprising a reaction product of A) and B), and C).

19. A curable composition according to claim 8 , comprising A) and B), and C).

20. A curable composition according to claim 1 , wherein R 1 , R 2 , R 3 , and R 4 each represent hydrogen.

Assignees

• Basf Se

Inventors

• Rudolf Peter
• Thiel Indre
• Thomas Hans-Josef
• Blattmann Hannes

Classifications

• C07D327/04 Primary

  Five-membered rings · CPC title

• C08G71/04 Primary

  Polyurethanes · CPC title