Amine phosphite antioxidants

• US 4,006,117 A
• Filed: 06/06/1975
• Issued: 02/01/1977
• Est. Priority Date: 01/24/1973
• Status: Expired due to Term

• Current Assignee: Occidental Chemical Corporation (Occidental Petroleum Corporation)
• Original Assignee: Hooker Chemicals & Plastics Corp. (Occidental Petroleum Corporation)
• Inventors: Colson, James G., Pawlak, Joseph A., Merrifield, D. Bruce
• Primary Examiner(s): Hoke, V. P.
• Application Number:
  US05/584,445
• Time in Patent Office: 606 Days
• Field of Search: 260/45.9 NP, 260/809
• US Class Current: 524/128
• CPC Class Codes: C07F 9/1411 with hydroxyalkyl compounds with further substituents on alkyl
• CPC Class Codes: C08K 5/524 Esters of phosphorous acids, e.g. of H3PO3
• CPC Class Codes: C10M 137/02 having no phosphorus-to-carbon bond
• CPC Class Codes: C10M 153/04 Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2207/281 of (cyclo)aliphatic monocarboxylic acids
• CPC Class Codes: C10M 2207/282 of (cyclo)aliphatic oolycarboxylic acids
• CPC Class Codes: C10M 2207/283 of polyhydroxy compounds
• CPC Class Codes: C10M 2207/286 of polymerised unsaturated acids
• CPC Class Codes: C10M 2209/103 Polyethers, i.e. containing di- or higher polyoxyalkylene groups
• CPC Class Codes: C10M 2211/02 containing carbon, hydrogen and halogen only
• CPC Class Codes: C10M 2223/04 Phosphate esters
• CPC Class Codes: C10M 2223/042 Metal salts thereof
• CPC Class Codes: C10M 2225/00 Organic macromolecular compounds containing phosphorus as ingredients in lubricant compositions
• CPC Class Codes: C10M 2225/02 Macromolecular compounds from phosphorus-containg monomers, obtained by reactions involving only carbon-to-carbon unsaturated bonds
• CPC Class Codes: C10M 2227/02 Esters of silicic acids
• CPC Class Codes: C10M 2229/02 Unspecified siloxanes; Silicones
• CPC Class Codes: C10M 2229/05 containing atoms other than silicon, hydrogen, oxygen or carbon
• CPC Class Codes: C10N 2040/04 Oil-bath; Gear-boxes; Automatic transmissions; Traction drives
• CPC Class Codes: C10N 2040/042 for automatic transmissions
• CPC Class Codes: C10N 2040/044 for manual transmissions
• CPC Class Codes: C10N 2040/046 : for traction drives
• CPC Class Codes: C10N 2040/08 : Hydraulic fluids, e.g. brake-fluids
• CPC Class Codes: C10N 2040/22 : with essential removal of material , e.g. cutting, grinding or drilling
• CPC Class Codes: C10N 2050/10 : Semi-solids; greasy
• CPC Class Codes: Y10S 524/925 : Natural rubber compositions having nonreactive materials, i.e. NRM, other than: carbon, silicon dioxide, glass titanium dioxide, water, hydrocarbon or halohydrocarbon

Abstract

Compounds of the formula ##STR1## WHEREIN R is selected from the group consisting of ethylene, 1,2 propylene, 1,2 butylene, 2,3 butylene, styrylene and mixtures thereof,

x is an integer from 1 to 12,

R¹ is substituted or unsubstituted alkyl or aryl,

n is an integer from 1 to 3,

Each m is a member, selected independently from the group consisting of hydrocarbon of 1 to 20 carbon atoms, --RO-- , --RO-- H and --RO-- P(OR'"'"')₃^-n,

Wherein R, R'"'"', n and x are as above described, providing where m is --RO-- , the O-- bond thereof is attached to the phosphorus of an adjacent P(OR'"'"') moiety of a common nitrogen, and

P is 0 or 1, providing that when p is ##STR2## IS HYDROGEN, ARE DISCLOSED HAVING UTILITY AS NON-STAINING ANTIOXIDANTS.

Claims

1. A method of stabilizing organic substrates against atmospheric degradation comprising incorporating therein a stabilizing amount of at least one compound of the formula ##STR9## wherein R is selected from the group consisting of ethylene, 1,2-propylene, 1,2-butylene, 2,3-butylene, styrylene and mixtures thereof,

X is an integer from 1 to 12,

R'"'"' is substituted or unsubstituted alkyl or aryl,

n is an integer from 1 to 3,

each m is a member, selected independently from the group consisting of hydrocarbon of 1 to 20 carbon atoms, --RO-- H and --RO-- P(OR'"'"')_3-n, wherein R, R'"'"', n and x are as above described, and z is 0 or 1, providing that when z is 0, ##STR10## is hydrogen.

2. The method of claim 1 wherein the organic substrate contains a rubber selected from the group consisting of natural rubber, synthetic rubber and mixtures thereof.

3. The method of claim 1 wherein said compound is ##STR11##

4. The method of claim 1 wherein said compound is ##STR12##

5. The method of claim 1 wherein said compound is ##STR13##

6. The method of claim 1 wherein said compound is ##STR14##

7. The method of claim 1 wherein z is 0.

8. The method of claim 1 wherein R'"'"' is substituted or unsubstituted aryl.

9. The method of claim 1 wherein R'"'"' is phenyl or alkyl substituted phenyl.

10. The method of claim 1 wherein m is --RO-- P(OR'"'"')_3-n and z is 0.

11. The method of claim 1 wherein m is alkyl of 1-20 carbon atoms.

12. The method of claim 1 wherein m is cyclohexyl.