Compositions comprising a polymeric network

Patent metadata

Field	Value
Publication number	US-10246548-B2
Application number	US-201515533648-A
Country	US
Kind code	B2
Filing date	Dec 17, 2015
Priority date	Dec 19, 2014
Publication date	Apr 2, 2019
Grant date	Apr 2, 2019

Abstract

The present invention relates to a composition comprising a polymeric network having at least one unit of formula (I), (II), and/or (III);

wherein the composition is obtained by contacting at least one compound A comprising at least two functions selected from the group of function of formula —X—C(═O)—CHR1-C(═O)—R 2 , —C(═O)—C≡C—R 2 ; or —C(═O)—CR 1 ═CR 2 —NR 4 R 5 ; wherein at least 25% by weight of compounds A have a functionality ≤5, with % by weight relative to the total weight of compounds A; with at least one compound B comprising at least one —NH 2 , or —NH 3 + groups; wherein X, R 1 , R 2 , R 3 , R 4 , R 5 , L 1 and L 2 have the same meaning as that defined in the claims. The present invention also relates to a compound comprising at least two units and at most 5 units of formula (I), (II), and/or (III), described hereinabove. The present invention also relates to processes for preparing the composition and the compounds, to material, articles, and polymers comprising or using the compositions and compounds, and the use thereof.

First claim

The invention claimed is:

1. A composition comprising a polymeric network having at least one unit of formula (I), (II), and/or (III);

wherein said composition is obtained by contacting at least one compound A comprising at least two functions selected from the group of function of formula —X—C(═O)—CHR 1 —C(═O)—R 2 , —C(═O)—C≡C—R 2 ; or —C(═O)—CR 1 ═CR 2 —NR 4 R 5 ; wherein at least 25% by weight of compounds A have a functionality ≤5, with % by weight relative to the total weight of compounds A;
with at least one compound B comprising at least one —NH 2 , or —NH 3 + groups, or at least one functional group that generates —NH 2 or —NH 3 + in situ;
wherein the ratio R=(sum(functionality of compound A×number of moles of compound A))/(sum(functionality of compound B×number of moles of all compound B)) is <1;

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⁢

f
a

⁢

N
a

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b

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b

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wherein f a N a denotes the number of moles of —X—C(═O)—CHR 1 —C(═O)—R 2 , —C(═O)—C≡C—R 2 ; or —C(═O)—CR 1 ═CR 2 —NR 4 R 5 functions of the at least one compound A, and f b N b denotes the number of moles of —NH 2 , and/or —NH 3 + groups or the number of moles of functional groups which could generate —NH 2 or NH 3 + in situ, of the at least one compound B;
R 1 is hydrogen or is selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl; C 2-20 alkynyl; C 6-12 aryl, C 3-8 cycloalkyl; C 6-12 arylC 1-20 alkyl; C 3-8 cycloalkylC 1-20 alkyl; heteroC 1-20 alkyl; heterocyclyl; heterocyclylC 1-20 alkyl; heteroaryl; and heteroarylC 1-20 alkyl; wherein said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 3-8 cycloalkylC 1-20 alkyl; C 6-12 arylC 1-20 alkyl, heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
wherein at least one carbon atom or heteroatom of said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;
wherein said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl; can be unsubstituted or substituted with one or more Z 1 ; each Z 1 is independently selected from the group consisting of halogen; C 1-20 alkyl; C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; heteroarylC 1-20 alkyl; haloC 1-20 alkyl; haloC 1-20 alkyloxy; —OR 10 ; —SR 10 ; —S(O)R 9 ; —S(O) 2 R 9 ; —SO 2 NR 11 R 12 ; nitro; —NR 10 C(O)R 9 ; —NR 10 S(O) 2 R 9 ; —NR 10 C(O)NR 11 R 12 ; NR 11 R 12 ; cyano; —CO 2 R 10 ; —C(O)NR 11 R 12 ; and —C(O)R 9 ; and

R 4 is selected from the group consisting of C 1-20 alkyl, C 2-20 alkenyl; C 2-20 alkynyl; C 6-12 aryl, C 3-8 cycloalkyl; C 6-12 arylC 1-20 alkyl; C 3-8 cycloalkylC 1-20 alkyl; heteroC 1-20 alkyl; heterocyclyl; heterocyclylC 1-20 alkyl; heteroaryl; and heteroarylC 1-20 alkyl;
wherein said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 3-8 cycloalkylC 1-20 alkyl; C 6-12 arylC 1-20 alkyl, heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl, optionally comprises one or more heteroatoms in the alkyl, alkenyl, alkynyl moiety, said heteroatoms being each independently selected from O, S and N;
wherein at least one carbon atom or heteroatom of said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl; can be oxidized to form at least one C═O, C═S, N═O, N═S, S═O or S(O) 2 ;
wherein said C 1-20 alkyl, C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; and heteroarylC 1-20 alkyl; can be unsubstituted or substituted with one or more Z 4 ; each Z 4 is independently selected from the group consisting of NR 11 R 12 ; halogen; C 1-20 alkyl; C 2-20 alkenyl, C 2-20 alkynyl, C 6-12 aryl, C 3-8 cycloalkyl, C 6-12 arylC 1-20 alkyl, heteroC 1-20 alkyl; heterocyclyl; heteroaryl; C 3-8 cycloalkylC 1-20 alkyl; heterocyclylC 1-20 alkyl; heteroarylC 1-20 alkyl; haloC 1-20 alkyl; haloC 1-20 alkyloxy; —OR 10 ; —SR 10 ; —S(O)R 9 ; —S(O) 2 R 9 ; —SO 2 NR 11 R 12 ; nitro; —NR 10 C(O)R 9 ; —NR 10 S(O) 2 R 9 ; —NR 10 C(O)NR 11 R 12 ; cyano; —CO 2 R 10 ; —C(O)NR 11 R 12 ; and —C(O)R 9 ;

or wherein the ratio R=(sum(functionality of compound A×number of moles of compound A ))/(sum(functionality of compound A×number of moles of compound A)+sum(functionality of compound B×number of moles of all compound B)) is <1;

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f
a

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N
a

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when R 1 a

Assignees

• Univ Gent
• Ecole Superieure Physique & Chimie Ind Ville De Paris
• Centre National De La Rech Scientifique—Cnrs

Inventors

• Du Prez Filip
• Winne Johan
• Denissen Wim
• Leibler Ludwik
• Nicolaÿ Renaud

Classifications

• C07D295/185

  from aliphatic carboxylic acids · CPC title

• C07C225/16

  and containing six-membered aromatic rings · CPC title

• C07C229/30

  the carbon skeleton being acyclic and unsaturated · CPC title

• Y02W30/62

  Plastics recycling; Rubber recycling · CPC title

• C08J2375/14

  Polyurethanes having carbon-to-carbon unsaturated bonds · CPC title