Polymer compositions containing benzimidazole based stabilizer compounds
View Patent ↗The invention discloses a stabilized resin composition comprising a thermoplastic resin and a stabilizing benzimidazole based additive compound. In a second embodiment, the invention discloses a method to make a stabilized composition comprising a benzimidazole based stabilizing compound and a resin, said method comprising mixing said benzimidazole based stabilizing compound with said resin.
1. A stabilized composition comprising:
a) a polymeric resin, and
b) a non photo sensitive benzimidazole based stabilizer compound.
2. The composition of claim 1 wherein said benzimidazole based stabilizer compound is selected from thiazolobenzimidazolone based compounds and thioalkylsubstituted benzimidazole compounds.
3. The composition according to claim 1 wherein said benzimidazole based stabilizer compound is selected from compounds of structure (I):
wherein in structure (I) R 1 , R 2 , R 3 , R 4 are independently a carbocyclic structure, a fused structure, H, Cl, Br, F, OCH 3 , NO 2 , CH 3 , COOCH 2 CH 3 , alkyl, aryl, alkaryl, and OH, SH, O-alkyl, O-aryl, COOR, CONHR, halogen and R 2 and R 3 taken together form part of a saturated or an unsaturated, 5- or a 6-membered carbocyclic ring and A is independently S and O, and n is independently 1 and 2, R m is independently 2-naphthyl, H, C 1 -C 6 alkyl, phenoxy, cycloalkyl, and a trisubstituted aromatic radical, of the formula C 6 H 3 Y 1 Y 2 wherein Y 1 and Y 2 are independently H, Cl, Br, CH 3 , CF 3 , OCH 3 and NO 2 ,
and benzimidazole based compounds of structure (II) shown below:
wherein in structure (II) R x is H, —CO—(CH2) 16 —(CH 3 ) and —CO—CH 2 —C 6 H 5 , and R 1 , R 2 , R 3 , and R 4 are independently H, Cl, Br F, OCH 3 NO 2 , CH 3 , COOCH3CH 2 and R z is independently H, Cl, CH 3 and OCH 3 , and one or two atoms is present on the sulfur atom forming the corresponding sulfone and sulfoxide structures.
4. The composition of claim 1 wherein said resin is at least one polymeric resin selected from the group consisting of polyolefin homopolymers and copolymers, polyesters, polyurethanes, polyalkylene terephthalates, polysulfones, polyimides, polyphenylene ethers, styrenic polymers, polycarbonates, acrylic polymers, polyamides, polyacetals, polyvinyl chloride and combinations comprising the foregoing resins.
5. The composition of claim 1 wherein said stabilizing benzimidazole based compound is present at a level between about 0.0001 and about 5 percent by weight based on the total weight of the composition.
6. The composition of claim 1 wherein said stabilizing benzimidazole based compound is present at a level between about 0.0005 and about 1.0 percent by weight based on the total weight of the composition.
7. The composition of claim 1 , wherein said stabilising benzimidazole based compound is selected from the group consisting thiazolo[3,2-a]benzimidazole-3(2H)-one, 2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one, 6-chloro-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one, ethyl-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one-6-carboxylate, ethyl-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one-7-carboxylate, 7-methoxy-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one and combinations comprising the foregoing additive compounds.
8. The composition of claim 1 wherein said composition further comprises a compound selected from the group consisting of an alkaline metal salt of a fatty acid, metal oxides, hydroxycarbonates and combinations thereof.
9. The composition of claim 8 , wherein said alkaline metal salt of a fatty acid is calcium stearate.
10. The composition of claim 8 , wherein said metal oxide comprises an oxide selected from the group consisting of CaO, MgO, ZnO.
11. The composition of claim 8 , wherein said hydroxycarbonate is selected from the group consisting of MgAl hydroxycarbonate, ZnAl hydroxycarbonate and ZnMg hydroxycarbonate.
12. The composition of claim 1 , wherein the resin is a polyolefin resin.
13. The composition of claim 12 wherein polyolefin resin is selected from the group consisting of polypropylene, low density polyethylene, medium density polyethylene, high density polyethylene, linear low density polyethylene, ethylene/vinyl acetate copolymer, ethylene/propylene copolymer, and copolymers of ethylene or of propylene with other alpha-olefins.
14. The composition of claim 1 further comprising a stabilizer or mixture of stabilizers selected from the group consisting of phenolic antioxidants, 3-arylbenzofuranones, hindered amine stabilizers, ultraviolet light absorbers, phosphites, phosphonites, alkaline metal salts of fatty acids, metal oxides, hydrotalcites, epoxydized soybean oils, hydroxylamines, tertiary amine oxides, and/or thiosynergists.
15. Articles comprising the composition of claim 1 .
16. A method for producing a stabilized resin composition, said method comprising admixing a benzimidazole based stabilizing compound with a resin.
17. The method of claim 16 wherein said stabilizing benzimidazole based compound is selected from thiazolobenzimidazolone based compounds and thioalkylsubstituted benzimidazole compounds.
18. The method of claim 16 wherein said stabilizing benzimidazole based compound is selected from benzimidazole based stabilizing compounds of the structural formula (I):
wherein R 1 , R 2 , R 3 , R 4 in structure (I) are independently a carbocyclic structure, a fused structure, H, Cl, Br, F, OCH 3 , NO 2 , CH 3 , COOCH 2 CH 3 alkyl, aryl, alkaryl, and OH, SH, O-alkyl, O-Aryl, COOR, CONHR, halogen and R 2 and R 3 taken together form part of a saturated or an unsaturated, 5- or a 6-membered carbocyclic ring and A is independently S and O, and n is independently 1 and 2, R m in structure (I) is independently 2-naphthyl, H, C 1 -C 6 alkyl, phenoxy, cycloalkyl, and a trisubstituted aromatic radical, of the formula C 6 H 3 Y 1 Y 2 wherein Y 1 and Y 2 are independently H, Cl, Br, CH 3 , CF 3 , OCH 3 and NO 2 .
and benzimidazole based stabilizing compounds of structure (II) below:
wherein R x in structure (II) is independently H, CO—(CH2) 16 —(CH 3 ) and CO—CH 2 —C 6 H 5 , wherein R 1 , R 2 , R 3 , R 4 in structure (II) are independently H, Cl, Br, F, OCH 3 , NO 2 , CH 3 , COOCH 3 CH 2 , and R z in structure (II) is independently from H, Cl, CH 3 and OCH 3 and one or two atoms is present on the sulfur atom forming the corresponding sulfone and sulfoxide structures.
19. The method of claim 16 wherein said resin comprises a thermoplastic resin selected from the group consisting of polyolefin homopolymers and copolymers, polyesters, polyurethanes, polyalkylene terephthalates, polysulfones, polyimides, polyphenylene ethers, styrenic polymers, polycarbonates, acrylic polymers, polyamides, polyacetals, polyvinyl chloride and combinations comprising the foregoing resins.
20. The method of claim 16 , wherein said stabilizing benzimidazole based compound is selected from the group consisting of thiazolo[3,2-a]benzimidazole-3(2H)-one, 2-phenylthiazolo[3,2-a]benzimidazole-3(2H)-one, 2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one, 6-chloro-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one, ethyl-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one-6-carboxylate, ethyl-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one-7-carboxylate, 7-methoxy-2-phenylthiazolo[3,2-a]benzimidazol-3(2H)-one and combinations comprising the foregoing additive compounds.
21. The method of claim 16 further comprising a stabilizer or mixture of stabilizers selected from the group consisting of phenolic antioxidants, 3-arylbenzofuranones, hindered amine stabilizers, ultraviolet light absorbers, phosphites, phosphonites, alkaline metal salts of fatty acids, metal oxides, hydrotalcites, epoxydized soybean oils, hydroxylamines, tertiary amine oxides, and/or thiosynergists.