Use of protected n-hydroxyimide derivates and transition metal as oxygen scavenger system in transparent polyolefin films

Abstract

An oxygen-scavenging composition containing (I) a polymeric resin, (II) an organic oxidation additive based on a cyclic oxyimide, (III) a metal salt, preferably a transition metal salt, (IV) a sacrificial oxidizable substrate, and optionally, (V) an additional component; wherein components (I) and (IV) are different.

1 . An oxygen-scavenging composition comprising
 (I) a polymeric resin,   (II) an organic oxidation additive based on a cyclic oxyimide,   (III) a metal salt,   (IV) a sacrificial oxidizable substrate, and   optionally (V) an additional component; with the proviso that components (I) and (IV) are different.   
     
     
         2 . An oxygen-scavenging composition according to  claim 1 ,
 wherein   component (II) is present in an amount of 0.001-10 wt %, based on the polymeric resin,   component (III) is present in an amount of 0.001-10 wt %, based on the polymeric resin,   Component (IV) is present in an amount of 0.001-10 wt %, based on the polymeric resin, and   optionally component (V) is present in an amount of 0.001-10 wt %, based on the polymeric resin.   
     
     
         3 . The oxygen-scavenging composition according to  claim 2 , wherein the polymeric resin is a thermoplastic polymer selected from the group consisting of homopolymer of an olefin, a copolymer of olefin monomers, copolymer of olefin monomer with diolefin monomer, cyclic olefin, copolymer of one or more 1-olefin or diolefin with carbon monoxide, copolymer of one or more 1-olefin and diolefin with carbon monoxide, and polyvinyl alcohol. 
     
     
         4 . The oxygen-scavenging composition according to  claim 1 , wherein the organic oxidation additive is a compound selected from the group consisting of N-(trityloxy)-phthalimide, N-(stearoyloxy)phthalimide, N-(toluene-4-sulfonyloxy)-phthalimide, N-(2-benzoylbenzoyloxy)-phthalimide, N,N′-dihydroxypyromellitic diimine and N,N′-distearoyloxypyromelitimide. 
     
     
         5 . The oxygen-scavenging composition according to  claim 1 , wherein the metal salt is based on Co, Ce, Mn, Cu, Ni or Vd. 
     
     
         6 . The oxygen-scavenging composition according to  claim 1 , wherein the sacrificial oxidizable substrate is selected from the group consisting of polybutadiene, polyester, squalane, squalene, polystyrene, poly-limonene, poly alpha pinene, poly beta pinene, poly-norbornene, polylactic acid and a mixture of linear and branched alkyl chain C 6 -C 30  alcohol. 
     
     
         7 . The oxygen-scavenging composition according to  claim 1 , wherein the sacrificial oxidizable substrate is a polyterpenic resin. 
     
     
         8 . The oxygen-scavenging composition according to  claim 1 , wherein the oxygen-scavenging composition further comprises one or more additional components selected from the group consisting of filler, reinforcing agent, pigment, light stabilizer, antioxidant, antislip or antiblock additive, plasticizer, optical brightener, antistatic agent and blowing agent. 
     
     
         9 . The oxygen-scavenging composition according to  claim 1 , wherein the organic oxidation additive is a cyclic oxyimide of the formula (I) 
       
         
           
           
               
               
           
         
         wherein 
         n is 1, 2 or 4; 
         X is >C═O, >S(O) 2  or >C(X 1 )(X 2 ); 
         X 1  and X 2  independently of one another are hydrogen, C 1 -C 20  alkyl, C 3 -C 12  cycloalkyl unsubstituted or substituted by 1, 2 or 3 identic or different C 1 -C 4  alkyl; or phenyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; 
         Y is C 1 -C 30  alkyl, C 2 -C 30  alkenyl, C 3 -C 12  cycloalkyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; C 5 -C 12  cycloalkenyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms, C 7 -C 9  phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; diphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; triphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; C 2 -C 30  acyl, —COOY 0 , C 1 -C 30  sulfonyl, —Si(Y 1 ) 3  or —Si(OY 2 ) 3 ; 
         Y 0 , Y 1  and Y 2  independently of one another are hydrogen, C 1 -C 18  alkyl, C 3 -C 18  alkenyl, C 3 -C 12  cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; or C 7 -C 9  phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; and 
         Z is an organic radical; 
         with the provisos that 
         (1) when Y is C 1 -C 30  alkyl, C 2 -C 30  alkenyl or C 1 -C 30  sulfonyl, component (I) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer; and
 (2) when n is 2 or 4 and, at the same time, component (I) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer, Y is additionally hydrogen. 
 
       
     
     
         10 . A polymer article containing the oxygen-scavenging composition according to  claim 1 . 
     
     
         11 . The polymer article according to  claim 10  which is a film, a sheet or a laminate. 
     
     
         12 . A polymer article which is a coextruded multilayer film comprising:
 (A) a natural and/or a synthetic polymer and   (B) an organic oxidation additive based on a cyclic oxyimide of the formula (I)   
       
         
           
           
               
               
           
         
         wherein 
         n is 1, 2 or 4; 
         X is >C═O, >S(O) 2  or >C(X 1 )(X 2 ); 
         X 1  and X 2  independently of one another are hydrogen, C 1 -C 20  alkyl, C 3 -C 12  cycloalkyl unsubstituted or substituted by 1, 2 or 3 identic or different C 1 -C 4  alkyl; or phenyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; 
         Y is C 1 -C 30  alkyl, C 2 -C 30  alkenyl, C 3 -C 12  cycloalkyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; C 5 -C 12  cycloalkenyl unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; a bicyclic or tricyclic hydrocarbyl having 6 to 10 carbon atoms, C 7 -C 9  phenylalkyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; diphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; triphenylmethyl unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; C 2 -C 30  acyl, —COOY 0 , C 1 -C 30  sulfonyl, —Si(Y 1 ) 3  or —Si(OY 2 ) 3 ; 
         Y 0 , Y 1  and Y 2  independently of one another are hydrogen, C 1 -C 18  alkyl, C 3 -C 18  alkenyl, C 3 -C 12  cycloalkyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; phenyl which is unsubstituted or substituted by 1, 2 or 3 C 1 -C 4  alkyl; or C 7 -C 9  phenylalkyl which is unsubstituted or substituted on the phenyl by 1, 2 or 3 C 1 -C 4  alkyl; and 
         Z is an organic radical; 
         with the provisos that 
         (1) when Y is C 1 -C 30  alkyl, C 2 -C 30  alkenyl or C 1 -C 30  sulfonyl, component (I) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer; and
 (2) when n is 2 or 4 and, at the same time, component (I) is a polyolefin homo- or copolymer or a blend of a polyolefin homo- or copolymer with another synthetic polymer, Y is additionally hydrogen. 
 
       
     
     
         13 . A polymer article according to  claim 12  which is a food packaging.