POLYMERS OF A COMPOUND COMPRISING A MONOTHIOCARBONATE GROUP AND AN ETHYLENICALLY UNSATURATED GROUP

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.

Claims

1: 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 the group consisting of primary ad 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.

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 ##STR00016## wherein one of R.sup.1 to R.sup.4 represents an organic group comprising a vinyl group or a (meth)acrylic group and the remaining three of R.sup.1 to R.sup.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 40% by weight of compounds A) and B).

9: 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.

10: The polymer according to claim 9, 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.

11: A two component curable system, consisting of: a first component comprising all compounds with monothiocarbonate groups, and a second component comprising all compounds with primary or secondary amino groups.

12: A process for the manufacturing of a polymer, the process comprising: 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 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.

Description

EXAMPLES

Example 1

[0207] Polymer of Compound A) with One Methacryl Group and Compound B) with One Amino Group

[0208] In a 10 ml flask fitted with a magnetic stirrer 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-on (1.01 g) were melted. Butylamine (0.37 g) was added at 40° C. under stirring. Viscosity of the mixture increased over time. The polymer was still viscous after 24 h.

Example 2

Polymer of Compound A) with One Methacryl Group and Compound B) with Two Amino Groups in Presence of Solvent

[0209] In a 50 ml flask fitted with a magnetic stirrer 1,4 dioxane (0.75 g) and 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-on (2.02 g) were stirred and heated to 50° C. until homogenous solution was obtained. The solution was cooled to 25° C. Subsequently, 1,3 diaminocyclohexane (0.71 g) was added under stirring. The polymer solidified within 30 minutes at room temperature, tack-free polymer was obtained after 2 h.

Example 3

Polymer of Compound A) with One Methacryl Group and Compound B) with Three Amino Groups in Presence of Solvent

[0210] In a 50 ml flask fitted with a magnetic stirrer 1,4 dioxane (1.5 g) and 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-on (3.03 g) were stirred and heated to 50° C. until homogenous solution was obtained. The solution was cooled to 30° C. Subsequently, tris(2-aminoethyl)amine (0.74 g) was added under stirring. The polymer solidified within 4 minutes.

Example 4

Polymer of Compound A) with One Methacryl Group and Compound B) with Three Amino Groups without Solvent

[0211] In a 50 ml flask fitted with a magnetic stirrer 5-(methacryloyloxy)methyl-1,3-oxathiolane-2-on (3.03 g) was heated and subsequently cooled to 40° C. To the melt was added tris(2-aminoethyl)amine (0.74 g). The reaction mixture solidified within seconds under rapid increase of temperature.