Chemical methods for preparation of covalent adaptable networks

Patent metadata

Field	Value
Publication number	US-2020317841-A1
Application number	US-201816958061-A
Country	US
Kind code	A1
Filing date	Mar 9, 2018
Priority date	Mar 9, 2018
Publication date	Oct 8, 2020
Grant date	—

Abstract

A process for forming covalently cross-linked macromolecular networks, comprising reacting a compound of Formula (I), defined as R1-L-X—R3, with a compound of Formula (II), defined as HZ-R2, to form a macromolecular compound of Formula (III), defined as R1-L-Y, wherein R1 represents a macromolecular polymer backbone, L represents an aryl or arylalkyl, R2 independently represents an optionally substituted branched or linear C1-C10 alkane, a C2-C10 alkene, a C2-C10 alkyne, wherein the optional substituent is a second HZ-moiety or a carboxylic ester moiety, R3 represents CF3, H or C1-C10 alkane, X represents —C(O)—, —C(O)—C(CH2)— or —C(CH2)—C(O)—, Y represents —C(OH)(R3)—Z—R2, —C(O)—CH(R3)—CH2—Z—R2 or —CH(C(O)R3)—CH2—Z—R2; and Z represents S or NH. A covalently connected adaptable network formed by the process is also described.

First claim

1 - 10 . (canceled)

11 . A process for forming covalently cross-linked macromolecular networks, comprising:
reacting a compound of Formula (I), defined as R 1 -L-X—R 3 , with a compound of Formula (II), defined as HZ-R 2 , to form a macromolecular compound of Formula (III), defined as R 1 -L-Y; wherein:
R 1 represents a macromolecular polymer backbone,
L represents an aryl or an arylalkyl,
R 2 independently represents an optionally substituted branched or linear C 1 -C 10 alkane, or a C 2 -C 10 alkene, or a C 2 -C 10 alkyne, wherein the optional substituent is a second HZ-moiety or a carboxylic ester moiety,
R 3 represents CF 3 , H or C 1 -C 10 alkane,
X represents —C(O)—, —C(O)—C(CH 2 )— or —C(CH 2 )—C(O)—,
Y represents —C(OH)(R 3 )—Z—R 2 , —C(O)—CH(R 3 )—CH 2 —Z—R 2 or —CH(C(O)R 3 )—CH 2 —Z—R 2 ; and
Z represents S or NH.

12 . The process of claim 11 , wherein the process is reversible.

13 . The process of claim 11 , wherein the process further includes using an energy source.

14 . The process of claim 13 , wherein the cross-linking is thermally induced, by exposing the compounds of Formula (I) and (II) to a temperature from 40° C.-200° C.

15 . The process of claim 13 , wherein the cross-linking is activated by light, by exposing the compounds of Formula (I) and (II) to a light source of 200 nm-500 nm.

16 . The process of claim 11 , wherein the cross-linking reaction is an addition reaction.

17 . The process of claim 11 , wherein R 3 represents CF 3 , X represents —C(O)—, Z represents NH, and Y represents —C(OH)(CF 3 )—NH—R 2 .

18 . The process of claim 11 , wherein R 3 represents H, X represents —C(O)—, Z represents S, and Y represents —CH(OH)—S—R 2 .

19 . The process of claim 11 , wherein R 3 represents —C 1 -C 10 alkane, X represents —C(O)—C(CH 2 )—, Z represents S, and Y represents —C(O)—CH(—C 1 -C 10 alkane)-CH 2 —Z—R 2 .

20 . A covalently connected adaptable network formed by a process comprising:
reacting a compound of Formula (I), defined as R 1 -L-X—R 3 , with a compound of Formula (II), defined as HZ-R 2 , to form a macromolecular compound of Formula (III), defined as R 1 -L-Y; wherein:
R 1 represents a macromolecular polymer backbone,
L represents an aryl or an arylalkyl,
R 2 independently represents an optionally substituted branched or linear C 1 -C 10 alkane, or a C 2 -C 10 alkene, or a C 2 -C 10 alkyne, wherein the optional substituent is a second HZ-moiety or a carboxylic ester moiety,
R 3 represents CF 3 , H or C 1 -C 10 alkane,
X represents —C(O)—, —C(O)—C(CH 2 )— or —C(CH 2 )—C(O)—,
Y represents —C(OH)(R 3 )—Z—R 2 , —C(O)—CH(R 3 )—CH 2 —Z—R 2 or —CH(C(O)R 3 )—(CH 2 )—Z—R 2 ; and
Z represents S or NH.

Assignees

• Bosch Gmbh Robert

Inventors

• Sagar Kaushal
• Palale Suresh

Classifications

• C08F8/32

  by reaction with amines · CPC title

• C08F12/22

  Oxygen · CPC title

• C08J3/28

  Treatment by wave energy or particle radiation · CPC title

• C08J2325/06

  Polystyrene · CPC title

• C08F2810/20

  leading to a crosslinking, either explicitly or inherently · CPC title