Cyclic bis and tris phosphites and stabilized synthetic resin compositions

• US 4,670,492 A
• Filed: 10/22/1985
• Issued: 06/02/1987
• Est. Priority Date: 12/01/1983
• Status: Expired due to Fees

• Current Assignee: Adeka Argus Chemical Company Limited (Adeka Corporation)
• Original Assignee: Adeka Argus Chemical Company Limited (Adeka Corporation)
• Inventors: Tobita, Etsuo, Nakahara, Yutaka, Haruna, Tohru
• Primary Examiner(s): Kight, John
• Assistant Examiner(s): Morgan, Kriellion
• Application Number:
  US06/790,282
• Time in Patent Office: 588 Days
• Field of Search: 260/927 R, 529/119, 557/819, 558/77, 558/78
• US Class Current: 524/119
• CPC Class Codes: C07F 9/65744 condensed with carbocyclic or heterocyclic rings or ring systems
• CPC Class Codes: C07F 9/65746 the molecule containing more than one cyclic phosphorus atom
• CPC Class Codes: C08K 5/527 Cyclic esters

Abstract

Cyclic bis and tris phosphites are provided having the formula: ##STR1## wherein: A is selected from the group consisting of sulfur; oxygen; alkylidene having from one to about six carbon atoms; cycloalkylidene having from three to about eight carbon atoms; and phenyl and alkyl phenyl alkylidene having from seven to about fourteen carbon atoms;

R is selected from the group consisting of alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; and phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;

R₁ is selected from the group consisting of hydrogen; alkyl having from one to about eighteen carbon atoms; cycloalkyl having from three to about eight carbon atoms; and phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;

n is 2 or 3;

R₂ is ##STR2## wherein: m=0 when n is 2; and 1 when n is 3;

R₃, R₄, R₅, R₆ are hydrogen or lower alkyl; and, when the rings are aromatic, at least two of R₃, R₄, R₅ and R₆ in each ring is lower alkyl; and

Y is alkylidene having from three to about six carbon atoms; or ##STR3## the rings in R₂ being saturated or aromatic, and, when the rings are aromatic, at least two of R₃, R₄, R₅ and R₆ in each ring is lower alkyl, as well as stabilized synthetic resin compositions containing such phosphites.

Claims

1. Cyclic tris phosphites having the formula:

##STR116## wherein;

A is selected from the group consisting of sulfur;

oxygen;

alkylidene having from one to about six carbon atoms;

cycloalkylidene having from three to about eight carbon atoms; and

phenyl and alkyl phenyl alkylidene having from seven to about fourteen carbon atoms;

R is selected from the group consisting of alkyl having from one to about eighteen carbon atoms;

cycloalkyl having from three to about eight carbon atoms; and

phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;

R₁ is selected from the group consisting of hydrogen;

alkyl having from one to about eighteen carbon atoms;

cycloalkyl having from three to about eight carbon atoms; and

phenalkylidene and alkyl phenalkylidene having from seven to about twelve carbon atoms;

n is 3;

R₂ is ##STR117## wherein;

m=1;

R₃, R₄, R₅, R₆ are hydrogen or lower alkyl; and

, when the rings are aromatic, at least two of R₃, R₄, R₅ and R₆ in each ring is lower alkyl; and

Y is alkylidene having from three to about six carbon atoms.

2. A cyclic phosphite according to claim 1 in which R and R₁ are iso, secondary or tertiary alkyl having from three to about ten carbon atoms;

or cycloalkyl having from six to eight carbon atoms.

3. A cyclic phosphite according to claim 1 in which R₁ is in a para position and the formula is ##STR118## wherein:

A, R, R₁, n, R₂, M, R₃, R₄, R₅, R₆ and Y are as in claim 1.

4. A cyclic phosphite according to claim 1 in which R and R₁ are each isopropyl.

5. A cyclic phosphite according to claim 1 in which R is tertiary butyl.

6. A cyclic phosphite according to claim 1 in which R and R₁ are each tertiary butyl.

7. A cyclic phosphite according to claim 1 in which A is methylene.

8. A cyclic phosphite according to claim 1 in which A is alkylidene.

9. A cyclic phosphite according to claim 1 having the formula:

##STR119##

10. A polyvinyl chloride resin composition having improved resistance to deterioration when heated at 350°

F., comprising a polyvinyl chloride resin formed at least in part of the recurring group ##STR120## and having a chlorine content in excess of 40%, where X is either hydrogen or chlorine; and

a phosphite in accordance with claim 1.

11. A polyvinyl chloride resin composition in accordance with claim 10, in which the polyvinyl chloride resin is polyvinyl chloride homopolymer.

12. A polyvinyl chloride resin composition in accordance with claim 10, in which the polyvinyl chloride resin is a copolymer of vinyl chloride and vinyl acetate.

13. A olefin polymer composition having improved resistance to deterioration comprising an olefin polymer selected from the group consisting of polymers of alphaolefins having from two to six carbon atoms and polystyrene, and a phosphite in accordance with claim 1.

14. An olefin polymer composition in accordance with claim 13 wherein the polyolefin is polypropylene.

15. An olefin polymer composition in accordance with claim 13 wherein the polyolefin is polyethylene.

16. An acrylonitrile-butadiene-styrene terpolymer having improved resistance to deterioration comprising acrylonitrile-butadiene-styrene terpolymer and a phosphite in accordance with claim 1.

17. An ethylene-vinyl acetate copolymer composition having improved resistance to deterioration comprising ethylene-vinyl acetate copolymer and a phosphite in accordance with claim 1.

18. A polycarbonate resin composition having improved resistance to deterioration comprising a polycarbonate resin and a phosphite in accordance with claim 1.

19. A polyester polymer composition having improved resistance to deterioration comprising a polyester resin and a phosphite in accordance with claim 1.

20. A mixed polyphenylene-oxide-polystyrene-polycarbonate polymer composition having improved resistance to deterioration comprising polyphenylene oxide, polystyrene, polycarbonate, and a phosphite in accordance with claim 1.

21. A polyisoprene resin composition having improved resistance to deterioration comprising a polyisoprene resin formed at least in part of the recurring isoprene group;

and a phosphite in accordance with claim 1.