Oxalate ester—polyamine thermosetting compositions

Patent metadata

Field	Value
Publication number	US-10196548-B2
Application number	US-201615781851-A
Country	US
Kind code	B2
Filing date	Dec 13, 2016
Priority date	Dec 22, 2015
Publication date	Feb 5, 2019
Grant date	Feb 5, 2019

Abstract

Polymeric materials are disclosed herein that include a reaction product of components comprising: a) a first amine component having at least two and at most three primary amino groups, secondary amino groups, or a mixture thereof, with the proviso that the first amine component is not a silicone diamine; b) a second amine component having (i) greater than three primary amino groups, or (ii) at least three primary amino groups and a plurality of secondary amino groups, wherein the second amine component is a polymeric material having a carbon backbone or a polymeric material having a carbon backbone with a plurality of catenated nitrogen atoms; and c) an oxalate ester.

First claim

What is claimed is:

1. A two-part reactive composition comprising:
a) a first part comprising an oxalamido-containing compound and a compound of Formula (IV);
wherein the oxalamido-containing compound has at least two groups of the formula
—NR 5 —(CO)—(CO)—OR 4 ;

wherein the groups of the formula —NR 5 —(CO)—(CO)—OR 4 are the reaction products of a first amine component with a compound of Formula (IV);
wherein the first amine component has at least two and at most three primary amino groups, secondary amino groups, or a mixture thereof;
wherein the oxalamido-containing compound is free of a siloxane segment; and
wherein the compound of Formula (IV) is of the formula:
R 4 O—(CO)—(CO)—OR 4   (IV),

wherein each R 4 is independently alkyl, substituted alkyl, aralkyl, substituted aralkyl, alkenyl, aryl, or substituted aryl; and
wherein each R 5 is independently H, alkyl, substituted alkyl, alkylene, aralkyl, substituted aralkyl, alkenyl, aryl, or substituted aryl; and

b) a second part comprising a second amine component having (i) greater than three primary amino groups, or (ii) at least three primary amino groups and a plurality of secondary amino groups, wherein the second amine component is a polymeric material having a carbon backbone or a polymeric material having a carbon backbone with a plurality of catenated nitrogen atoms.

2. The two-part reactive composition of claim 1 , wherein the first amine component comprises one or more C2-C48 or higher amines.

3. The two-part reactive composition of claim 1 , wherein the first amine component comprises one or more C2-C16 amines, and 30 or less equivalent percent of the total amine content of the components for the reaction product forming the polymeric material comprises the one or more C2-C16 amines.

4. The two-part reactive composition of claim 1 , wherein the first amine component comprises one or more C17-C48 or higher amines, and 5 to 40 equivalent percent of the total amine content of the components for the reaction product forming the polymeric material comprises the one or more C17-C48 or higher amines.

5. The two-part reactive composition of claim 1 , wherein the second amine component comprises a polyethylene imine having a number average molecular weight (M n ) of 600 to 100,000 Daltons.

6. The two-part reactive composition of claim 1 , wherein the second amine component comprises a Polymer B comprising:
at least 80 weight percent of a plurality of first monomeric units of Formula (I):

wherein:
each R 1 is independently hydrogen or methyl;
each R 2 and R 3 are independently a linear or branched alkyl having 4 to 14 carbon atoms; and

at least three monomeric units having a primary amino group.

7. The two-part reactive composition of claim 6 , wherein Polymer B has a weight average molecular weight (M w ) of at least 12,000 Daltons and a weight average molecular weight (M w ) of no greater than 100,000 Daltons.

8. The two-part reactive composition of claim 6 , wherein a monomeric unit of the plurality of monomeric units of Polymer B having a primary amino group is a reaction product of an amine or a polyamine with a monomeric unit formed from maleic anhydride or a monomeric unit formed from vinyl dimethyl azlactone.

9. The two-part reactive composition of claim 8 , wherein the amine is ethylene diamine, propylene diamine, butanediamine, hexanediamine, piperazine, a polyether-amine, a dimer diamine, 3(4),8(9)-bis-(aminomethyl)-tricyclo-[5,2,1,02,6] decane, or a combination thereof; and/or the polyamine is a polyether-amine.

10. The two-part reactive composition of claim 1 , wherein 10 to 80 equivalent percent of the total amine content of the components for the reaction product forming the polymeric material comprises the second amine component.

11. The two-part reactive composition of claim 1 , further comprising a component selected from the group consisting of a non-ionic surfactant, a polyethylene glycol, a filler, a dye, an antioxidant, a tackifier, a solvent, a diluent, a viscosity modifier, an antimicrobial agent, and combinations thereof.

12. A multi-chambered mixing and/or dispensing device containing the two-part reactive composition of claim 1 , wherein the first part is present in a first chamber of the multi-chambered mixing and/or dispensing device, and the second part is present in a second chamber of the multi-chambered mixing and/or dispensing device.

13. A method of preparing a polymeric material comprising:
providing a two-part reactive composition according to claim 1 ; and
combining the first part and the second part under conditions effective for the reaction of the first part and the second part to form the polymeric material.

14. The method of claim 13 , wherein combining the first part and the second part comprises mixing the first part and the second part.

15. The method of claim 13 , wherein conditions effective for the reaction of the first part and the second part to form the polymeric material comprise room temperature or body temperature.

Assignees

• 3M Innovative Properties Co

Inventors

• Rasmussen Jerald K
• Demirgöz Döne
• Christian Taylor M
• Kipke Cary A
• Beveridge Nicole Morozowich
• Klein Andrew P
• Hays David S
• Dizio James P
• Griesgraber George W
• Asmus Robert A

Classifications

• C08F224/00

  Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a heterocyclic ring containing oxygen (cyclic esters of polyfunctional acids C08F218/00; cyclic anhydrides of unsaturated acids C08F220/00, C08F222/00) · CPC title

• C09J133/14 Primary

  of esters containing halogen, nitrogen, sulfur or oxygen atoms in addition to the carboxy oxygen · CPC title

• C09J11/06

  organic · CPC title

• C09J4/06 Primary

  {Organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond} in combination with a macromolecular compound other than an unsaturated polymer of groups C09J159/00 - C09J187/00 · CPC title

• C08F2500/02

  Low molecular weight, e.g. <100,000 Da. · CPC title