Cyclic carbonates

Patent metadata

Field	Value
Publication number	US-10407534-B2
Application number	US-201615567513-A
Country	US
Kind code	B2
Filing date	Apr 15, 2016
Priority date	Apr 23, 2015
Publication date	Sep 10, 2019
Grant date	Sep 10, 2019

Abstract

Compounds of the formula

in which
R 1 is an organic radical having a (meth)acryloyl group and R 2 , R 3 , and R 4 independently of one another are an H atom or a C1 to C10 alkyl group.

First claim

What is claimed is:

1. A compound of formula (I)

in which
R 1 is an organic radical having a (meth)acryloyl group and
R 2 , R 3 , and R 4 independently of one another are an H atom or a C1 to C10 alkyl group.

2. The compound according to claim 1 , wherein
R 1 is an organic radical having a total of not more than 24 C atoms and comprising no heteroatoms other than oxygen atoms.

3. The compound according to claim 1 , wherein
R 1 is a group of formula (II)

in which X is a bond or an alkylene group having 1 to 18 C atoms and R 5 is an H atom or a methyl group,
or R 1 is a group of formula (III)

in which m and p independently of one another are 0 or an integer from 1 to 10, R 5 is an H atom or a methyl group, and R 6 is an H atom or a C1 to C10 alkyl group,
or R 1 is a group of formula (IV)

in which s and t independently of one another are 0 or an integer from 1 to 10, R 5 is an H atom or a methyl group, and R 7 is an H atom or a C1 to C10 alkyl group.

4. The compound according to claim 1 , wherein R 2 is a methyl group and R 3 and R 4 are an H atom.

5. A process for preparing the compound of claim 3 , in which R 1 is a group of the formula (II), comprising:
reacting, in a first stage, a compound having a terminal triple bond with a hydroxyalkanone or hydroxyalkanal, the triple bond undergoing addition to the carbonyl group of the hydroxyalkanone or hydroxyalkanal to form a dihydroxy compound,
protecting, in a second stage, the hydroxyl group of the dihydroxy compound that did not originate from the carbonyl group with a protecting group,
ring closing, in a third stage, to form a carbonate group with carbon dioxide, and
replacing, in a fourth stage, the protecting group with a (meth)acryloyl group.

6. A process for preparing the compound of claim 3 , in which R 1 is a group of the formula (III), comprising:
reacting, in a first stage, a compound having a terminal triple bond with an alkanone or alkanal which comprises an acetal group, the triple bond undergoing addition to the carbonyl group of the alkanone or alkanal to form a hydroxy compound,
ring closing, in a second stage, to form a carbonate group with carbon dioxide,
ring closing, in a third stage, to form a 1,3-dioxane ring by reaction of the acetal group with a compound having a total of at least three hydroxyl groups, with two of the hydroxyl groups being located in 1,3 position, and
introducing, in a fourth stage, the (meth)acryloyl group by esterification or transesterification of the remaining hydroxyl group.

7. A process for preparing the compound of claim 3 , in which R 1 is a group of the formula (IV), comprising:
reacting, in a first stage, a compound having a terminal triple bond with an alkanone or alkanal which comprises an acetal group, the triple bond undergoing addition to the carbonyl group of the alkanone or alkanal to form a hydroxy compound,
ring closing, in a second stage, to form a carbonate group with carbon dioxide,
ring closing, in a third stage, to form a 1,3-dioxolane ring by reaction of the acetal group with a compound having a total of at least three hydroxyl groups, with two of the hydroxyl groups being located in 1,2 position, and
introducing, in a fourth stage, the (meth)acryloyl group by esterification or transesterification of the remaining hydroxyl group.

8. An epoxy resin composition comprising the compound of claim 1 .

9. An epoxy resin composition comprising
a) a compound of claim 1 ,
b) an epoxy compound having at least one epoxy group
c) optionally a hardener for the epoxy compound, and
d) optionally a further constituent.

10. The epoxy resin composition according to claim 9 , comprising 0.1 to 10 000 parts by weight of the compound of the formula (I) per 100 parts by weight of the epoxy compound.

11. The epoxy resin composition according to claim 9 , wherein the hardener is present, and has at least one primary or secondary amino group.

12. A two-component binder system comprising:
a component A comprising
a) the compound of claim 1 ,
b) an epoxy compound having at least one epoxy group, and
a component B comprising
c) a hardener for the epoxy compound.

13. A coating material, casting material, or adhesive comprising the epoxy resin composition of claim 9 .

Assignees

• Basf Se

Inventors

• Mormul Verena
• Klopsch Rainer
• Yu Miran
• Scherr Guenter
• Ghislieri Diego

Classifications

• C07D407/06

  linked by a carbon chain containing only aliphatic carbon atoms · CPC title

• C08G59/504

  containing an atom other than nitrogen belonging to the amine group, carbon and hydrogen · CPC title

• C07D317/40 Primary

  Vinylene carbonate; Substituted vinylene carbonates · CPC title

• C08G59/245

  aromatic · CPC title

• C08G59/5026

  cycloaliphatic · CPC title