Non explosive bis-sulfonyl azides

Abstract

The invention relates to a compound of the general formula (I) N 3 O 2 S—Ar-L-Ar′—SO 2 N 3 , wherein: —Ar and Ar′ are aromatic building blocks; and —L is a linking group comprising at least one heteroatom as well as an organic chain denoted as Sp″ and having at least two carbon atoms. The invention also relates to a compound of the general formula (II) wherein: —Ar and Ar′ are aromatic building blocks; —L is a covalent bond or a linking group; —m and n are both 0 or 1, at least one of m and n being 1; —Sp and Sp′ are organic chains having at least two carbon atoms. The invention also relates to the use of these compounds as cross linking agents in the manufacture of polymers.

The invention claimed is: 
     
       1. A compound of the general formula
   N 3 O 2 S—Ar-L-Ar′—SO 2 N 3 ,  (I)
 
 wherein: 
 Ar and Ar′ are each independently a substituted or unsubstituted phenyl group; 
 L is a linking group —O-Sp″-O; and 
 Sp″ is an aliphatic group having at least two carbon atoms; 
 not including compounds of the general formula:
   N 3 O 2 S—(Ar- z )-R 1 -Sp′″-(R 2 —(Ar- z )-SO 2 N 3 ) x ,  (III)
 
 
 wherein: 
 Ar is an aromatic building block; 
 z is a hydrogen atom or a chlorine atom 
 x is superior or equal to 1 
 R 1  is selected from the group consisting of —CO—NH—, —NH—CO—, and —CO—N—CH 3 ; 
 R 2  is selected from the group consisting of —CO—NH—, —NH—CO—, and —CO—N—CH 3  or —CH═CH—; and 
 Sp′″ is an organic chain with at least one carbon atom or a covalent bond. 
 
     
     
       2. The compound according to  claim 1 , wherein Sp″ is an aliphatic chain having at least 3 carbon atoms. 
     
     
       3. The compound according to  claim 1 ,
 wherein Ar and Ar′ are identical phenyl groups. 
 
     
     
       4. The compound of  claim 1 , wherein the compound is:
 1,6-bis-(4-azidosulfonylphenoxy)-hexane, 
 1,10-bis-(4-azidosulfonylphenoxy)-decane, 
 1,2-bis-(4-azidosulfonylphenoxy)-hexadecane, 
 an isomeric mixture of 4,8-bis-(4-azidosulfonylphenoxymethyl)-tricyclo[5.2.1.0 2.6 ]decane, 
 1,4-bis-(4-azidosulfonylphenoxymethyl)-cyclohexane, or 
 1,n-bis-(4-azidosulfonylphenyl)-polyethylene glycol ether. 
 
     
     
       5. A composition comprising the compound according to  claim 1 , and containing at most 50% (w/w) of a phlegmatizing agent or is without phlegmatizing agent. 
     
     
       6. A method of cross-linking a substrate, comprising the use of the reacting the substrate with a compound of the general formula
   N 3 O 2 S—Ar-L-Ar′—SO 2 N 3 ,  (I)
 
 wherein: 
 Ar and Ar′ are each independently a substituted or unsubstituted phenyl group; 
 L is a linking group —O—Sp″—O—; and 
 Sp″ is an aliphatic group having at least two carbon atoms; and 
 not including compounds of the general formula:
   N 3 O 2 S—(Ar- z )-R 1 -Sp′″-(R 2 —(Ar- z )-SO 2 N 3 ) x ,  (III)
 
 
 wherein: 
 Ar is an aromatic building block; 
 z is a hydrogen atom or a chlorine atom 
 x is superior or equal to 1 
 R 1  is selected from the group consisting of —CO—NH—, —NH—CO—, and —CO—N—CH 3    
 R 2  is selected from the group consisting of —CO—NH—, —NH—CO—, and —CO—N—CH 3  or —CH═CH—; and 
 Sp′″ is an organic chain with at least one carbon atom or a covalent bond. 
 
     
     
       7. The method according to  claim 6 , wherein the compound is selected from the group consisting of:
 1,6-bis-(4-azidosulfonylphenoxy)-hexane, 
 1,10-bis-(4-azidosulfonylphenoxy)-decane, 
 1,2-bis-(4-azidosulfonylphenoxy)-hexadecane, 
 an isomeric mixture of 4,8-bis-(4-azidosulfonylphenoxymethyl)-tricyclo[5.2.1.0 2.6 ]decane or 
 1,4-bis-(4-azidosulfonylphenoxymethyl)-cyclohexane, and 
 1,n-bis-(4-azidosulfonylphenyl)-polyethylene glycol ether. 
 
     
     
       8. The method according to  claim 6 , wherein the reacting step yields a polymer. 
     
     
       9. The method according to  claim 6 , wherein the reacting step yields polyolefins, polyolefin copolymers, and/or blends of polyolefins. 
     
     
       10. The method according to  claim 6 , wherein the reacting step yields elastomers, elastomer copolymers, and/or blends of elastomers. 
     
     
       11. The method of  claim 7 , wherein the reacting step is performed with a composition comprising the compound and at most 50% (w/w) of a phlegmatizing agent or comprising the compound without a phlegmatizing agent. 
     
     
       12. A compound of the general formula:
   (N 3 O 2 S—Ar—Y) 2 Sp″,  (I″)
 
 wherein
 Ar is a substituted or unsubstituted phenyl group; 
 Sp″ is an aliphatic group having at least two carbon atoms; and 
 Y is a functional group selected from the group consisting of —O—, —C(═O)O— and —OC(═O)—. 
 
 
     
     
       13. A composition comprising the compound according to  claim 12 , and containing at most 50% (w/w) of a phlegmatizing agent or is without phlegmatizing agent. 
     
     
       14. A method of cross-linking a substrate, comprising reacting the substrate with the compound of  claim 12 . 
     
     
       15. The method of  claim 14 , wherein the reacting step is performed with a composition comprising the compound and at most 50% (w/w) of a phlegmatizing agent or comprising the compound without a phlegmatizing agent. 
     
     
       16. The method of  claim 14 , wherein the reacting step yields a polymer. 
     
     
       17. The method of  claim 14 , wherein the reacting step yields polyolefins, polyolefin copolymers, and/or blends of polyolefins. 
     
     
       18. The method of  claim 14 , wherein the reacting step yields elastomers, elastomer copolymers, and/or blends of elastomers.