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

Abstract

An oxygen scavenger composition for food packaging application comprising (I) a polymeric resin, (II) one or more oligomeric photosensitizers, (III) a metal salt, preferably Cu stearate or Mn stearate; (IV) a sacrificial oxidizable substrate, and optionally (V) additional components.

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 homo- or copolymers of olefin monomers, copolymers of olefin monomers with diolefin monomers, cyclic olefins, copolymers of one or more 1-olefins or diolefins with carbon monoxide, copolymers of one or more 1-olefins and diolefins 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 alcohols. 
     
     
         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 fillers, reinforcing agents, pigments, light stabilizers, antioxidants, antislip or antiblock additives, plasticizers, optical brighteners, antistatic agents and blowing agents. 
     
     
         9 . The oxygen-scavenging composition according to  claim 1 , wherein the organic oxidation additive is a cyclic oxyimide of 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 identical 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 (1) 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 containing:
 (A) a natural and/or a synthetic polymer and   (B) an organic oxidation additive based on a cyclic oxyimide of 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 identical 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 (A) 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 (A) 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. 
     
     
         14 - 15 . (canceled)