ROMP with alkoxy ether groups

Abstract

The invention relates to metathesis oligomers wherein one or more alkoxy ether groups are attached to the oligomer moiety. Also disclosed is a polymerisable composition comprising a catalytically effective amount of a penta- or hexavalent ruthenium or osmium carbene catalyst, the process for preparing the metathesis polymer by applying the reaction conditions of Ring Opening Metathesis Polymerisation (=ROMP) to the polymerisable composition; and various technical applications of the metathesis oligomers as antifog agents.

1 . A compound of the formula  
       A-[X-(Y-Z) p ] m [X′(Y′-Z′) q ] n B-Z″  (1),  
     wherein 
 one of m and n represents zero, one or a numeral greater than one and the other one represents one or a numeral greater than one, with the proviso that the sum of m and n is at least two;  
 p and q independently of one another represent zero, one or a numeral greater than one and the other one represents one or a numeral greater than one;  
 A and B represent chain terminal groups from the chain transfer agent A-B;  
 X and X′ independently of one another represent unsaturated or hydrogenated repeating units from cycloolefins polymerised by metathesis;  
 Y and Y′ represent identical or different bivalent groups; and  
 Z, Z′ and Z″ independently of one another represent alkoxy ether groups selected from the group consisting of 
 hydroxy-C 2 -C 3 alkoxy-poly-C 2 -C 3 alkoxy and C 1 -C 4 alkoxy-poly-C 2 -C 3 alkoxy; or  
 
 Z, Z′ and Z″ independently of one another represent alkoxy ether groups selected from the group consisting of dihydroxy-C 3 -C 7 alkoxy and dihydroxy-C 2 -C 3 alkoxy-poly-C 2 -C 3 alkoxy, wherein hydroxy is etherified by another group  
   A-X″-B,  
  wherein A-B represent chain terminal groups from the chain transfer agent A-B and X″ represents unsaturated or hydrogenated repeating units from cycloolefins polymerised by metathesis.  
 
   
   
       2 . A compound (I) according to  claim 1 , wherein 
 X and X′ independently of one another represent an unsaturated or hydrogenated repeating unit from cycloolefins polymerised by metathesis selected from the group consisting of cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclooctene, cyclopentadiene, dicyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene, norbornadiene, norbornene and norbornene derivatives; and 
 A, B, Y, Y′, Z, Z′, Z″, p, q, m and n are as defined in  claim 1 .  
   
   
   
       3 . A compound (I) according to  claim 1 , wherein 
 one of m and n represents a numeral from 2 to 20; and the other one represents zero; and    A, B, X, X′, Y, Y′, Y″, Z, Z′, Z″, p and q are as defined in  claim 1 .    
   
   
       4 . A compound (I) according to  claim 1 , wherein 
 Z, Z′ and Z″ independently of one another represent alkoxy ether groups selected from the group consisting of 2-hydroxyethoxy-polyethoxy, 2-C 1 -C 4 alkoxy-polyethoxy, 3-hydroxypropoxypoly-n-propoxy and 3-C 1 -C 4 alkoxy-poly-n-propoxy; and    A, B, X, X′, Y, Y′, Y″, p, q, m and n are as defined in  claim 1 .    
   
   
       5 . A compound (I) according to  claim 1 , wherein 
 Z, Z′ and Z″ independently of one another represent methoxy-polyethoxy, polyethoxy, methoxy-poly-n-propoxy, and ethoxy-poly-n-propoxy; and    A, B, X, X′, Y, Y′, Y″, p, q, m and n are as defined in  claim 1 .    
   
   
       6 . A compound (I) according to  claim 1 , wherein 
 p and q represent zero;    one of m and n represents a numeral from 2 to 20 and the other one represents zero;    A and B represent chain terminal groups from the chain transfer agent C 3 -C 8 alkene;    X and X′ independently of one another represent an unsaturated or hydrogenated repeating unit from cycloolefins polymerised by metathesis selected from the group consisting of cyclopropene, cyclobutene, cyclopentene, cycloheptene, cyclooctene, cyclopentadiene, dicyclopentadiene, cyclohexadiene, cycloheptadiene, cyclooctadiene, norbornadiene, norbornene and norbornene derivatives;    Y and Y′ independently of one another represent bivalent groups selected from the group consisting of —C(═O)—, —O—C(═O)— and C 1 -C 8 alkylene; and    Z, Z′ and Z″ independently of one another represent an alkoxy ether group selected from the group consisting of methoxy-polyethoxy, polyethoxy, methoxy-poly-n-propoxy, and ethoxy-poly-n-propoxy.    
   
   
       7 . A compound (I) according to  claim 1 , wherein 
 p and q represent zero;    one of m and n represents a numeral from 2 to 20 and the other one represents zero;    A and B represent chain terminal groups from the chain transfer agent C 3 -C 8 alkene;    X and X′ independently of one another represent an unsaturated or hydrogenated repeating unit from cycloolefins polymerised by metathesis selected from the group consisting of cyclopentadiene, dicyclopentadiene, norbornadiene, norbornene and norbornene derivatives; and    Z″ represents an alkoxy ether group selected from the group consisting of methoxy-polyethoxy, polyethoxy, methoxy-poly-n-propoxy, and ethoxy-poly-n-propoxy.    
   
   
       8 . A compound according to  claim 1  selected from the group consisting of  
     
       
         
         
             
             
         
       
     
     wherein m and a represent numerals from 5 to 20.  
   
   
       9 - 14 . (canceled)  
   
   
       15 . A method for increasing the antifog properties of polymers which comprises incorporating within film polymer material a compound according to  claim 1 .  
   
   
       16 . A method according to  claim 15 , wherein the film material is a greenhouse or food packaging film material.