Recyclable crosslinked polymeric compositions

Patent metadata

Field	Value
Publication number	US-11945947-B2
Application number	US-202318138277-A
Country	US
Kind code	B2
Filing date	Apr 24, 2023
Priority date	Apr 25, 2022
Publication date	Apr 2, 2024
Grant date	Apr 2, 2024

Abstract

A crosslinked polymeric composition comprising A, B, C, D, and E units having the following structures, respectively:andwherein dashed bonds represent optional bonds; the asterisks (*) in C units represent covalent bond connection points with asterisks in A units and E units; the asterisks (*) in D units represent covalent bond connection points with asterisks in B units and E units; wherein a portion of E units are bound to C units, a portion of E units are bound to D units, and a portion of E units are bound to both C and D units; and the composition contains a multiplicity of A, B, C, D, and E units. Also described is a method for producing the crosslinked polymeric composition by reacting epoxy-containing molecules (A molecules), isocyanate-containing molecules (B molecules), and disulfide-containing molecules (C molecules).

First claim

What is claimed is:

1. A crosslinked polymeric composition comprising A, B, C, D, and E units, defined as follows:
A units:

wherein G is a hydrocarbon linker;
B units:

wherein M is a hydrocarbon linker;
C units:

wherein J is a linkage resulting from reaction between an epoxy group and a group reactive with an epoxy group;
D units:

wherein K is a linkage resulting from reaction between an isocyanate group and a group reactive with an isocyanate group; and
E units:

wherein L 1 and L 2 are independently hydrocarbon linkers;
wherein:
dashed bonds represent optional bonds;
the asterisks (*) in C units represent covalent bond connection points with asterisks in A units and E units;
the asterisks (*) in D units represent covalent bond connection points with asterisks in B units and E units;
wherein a portion of E units are bound to C units, a portion of E units are bound to D units, and a portion of E units are bound to both C and D units; and
the composition contains a multiplicity of A units, multiplicity of B units, multiplicity of C units, multiplicity of D units, and multiplicity of E units.

2. The composition of claim 1 , wherein J is a linkage resulting from reaction between an epoxy group and a group reactive with an epoxy group, wherein the group reactive with an epoxy group is selected from an amino, hydroxy, or carboxylic acid group.

3. The composition of claim 2 , wherein C units have the following structure:

wherein Y is selected from

and C(O)O—; and the dashed bond represents an optional bond that can only be present when Y is

4. The composition of claim 1 , wherein K is a linkage resulting from reaction between an isocyanate group and a group reactive with an isocyanate group, wherein the group reactive with an isocyanate group is selected from an amino, hydroxy, or carboxylic acid group.

5. The composition of claim 4 , wherein D units have the following structure:

wherein Z is —NH—, —O—, or a bond.

6. The composition of claim 1 , wherein G (in A units) contains at least one aromatic ring.

7. The composition of claim 1 , wherein G (in A units) contains at least two aromatic rings interconnected by an alkylene linkage.

8. The composition of claim 1 , wherein A units comprise the following structure:

wherein R 1 and R 2 are independently selected from H and CH 3 groups.

9. The composition of claim 1 , wherein M (in B units) is an alkylene linker of the formula —(CH 2 ) n —, wherein n is an integer in a range of 1-12.

10. The composition of claim 1 , wherein M (in B units) is an alkylene linker of the formula —(CH 2 ) n —, wherein n is an integer in a range of 3-12.

11. The composition of claim 1 , wherein M (in B units) contains at least one aromatic ring.

12. The composition of claim 1 , wherein the crosslinked polymeric composition further comprises a solid filler material homogeneously distributed throughout the crosslinked polymeric composition.

13. The composition of claim 12 , wherein the solid filler material is selected from carbon particles, glass particles, basalt particles, cellulose particles, and metallic particles.

14. The composition of claim 12 , wherein the solid filler material comprises carbon particles.

15. A method for producing the crosslinked polymeric composition of claim 1 , the method comprising reacting the following components:
A molecules:

wherein G is a hydrocarbon linkage connected to at least E 1 and E 2 and optionally to one or both of E 3 and E 4 , if present, wherein E 1 , E 2 , E 3 , and E 4 are epoxy groups;
B molecules:

wherein M is a hydrocarbon linkage connected to at least I 1 and I 2 and optionally I 3 , if present, wherein I 1 , I 2 and I 3 represent isocyanate groups;
C molecules:

wherein L 1 and L 2 are independently hydrocarbon linkers, and V 1 and V 2 are independently functional groups reactive with epoxy groups (E 1 , E 2 , E 3 , and E 4 groups) and isocyanate groups (I 1 , I 2 , and I 3 groups);
wherein:
dashed bonds represent optional bonds;
V 1 and V 2 react with E 1 and E 2 , and optionally E 3 and/or E 4 , if present, to produce first linking units having the formula:

wherein J is a linkage resulting from reaction between an epoxy group, selected from E 1 , E 2 , E 3 , and E 4 groups, and a group reactive with an epoxy group, selected from V 1 and V 2 groups, to result in said first linking units covalently bonding between G hydrocarbon linkages of A molecules and L 1 and L 2 of C molecules; and
V 1 and V 2 react with I 1 and I 2 , and optionally I 3 , if present, to produce second linking units having the formula:

wherein K is a linkage resulting from reaction between an isocyanate group, selected from I 1 , I 2 , and I 3 groups, and a group reactive with an isocyanate group, selected from V 1 and V 2 groups, to result in said second linking units covalently bonding between M hydrocarbon linkages of B molecules and L 1 and L 2 of C molecules.

16. The method of claim 15 , wherein G (in A molecules) contains at least one aromatic ring.

17. The method of claim 15 , wherein G (in A molecules) contains at least two aromatic rings interconnected by an alkylene linkage.

18. The method of claim 15 , wherein A molecules have the following structure:

wherein R 1 and R 2 are independently selected from H and CH 3 groups.

19. The method of claim 15 , wherein M (in B molecules) is an alkylene linker of the formula —(CH 2 ) n —, wherein n is an integer in a range of 1-12.

20. The method of claim 15 , wherein M (in B molecules) is an alkylene linker of the formula —(CH 2 ) n —, wherein n is an integer in a range of 3-12.

21. The method of claim 15 , wherein B molecules have the following structure:

Assignees

• Ut Battelle Llc

Inventors

• Saito Tomonori
• Zhou Zhengping
• Rahman Md Anisur

Classifications

• C08L75/02 Primary

  Polyureas · CPC title

• C08G18/3857

  having nitrogen in addition to sulfur · CPC title

• C08G18/3863

  containing groups having sulfur atoms between two carbon atoms, the sulfur atoms being directly linked to carbon atoms or other sulfur atoms · CPC title

• C08G18/58

  Epoxy resins {(C08G18/42, C08G18/48 take precedence; reaction products of epoxy resins with at least equivalent amounts of compounds containing active hydrogen C08G18/6407, with at least equivalent amounts of amines C08G18/6415; polymeric products of isocyanates or isothiocyanates with epoxy compounds having no active hydrogen C08G18/003)} · CPC title

• C08G18/73

  acyclic · CPC title