Surfactants

• US 5,944,650 A
• Filed: 10/29/1997
• Issued: 08/31/1999
• Est. Priority Date: 10/29/1997
• Status: Expired due to Fees

• Current Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Original Assignee: Xerox Corporation (Xerox Holdings Corp.)
• Inventors: Smith, Paul F., Hu, Nan-Xing, Ong, Beng S.
• Primary Examiner(s): Lovering, Richard D.
• Application Number:
  US08/960,754
• Time in Patent Office: 671 Days
• Field of Search: 252/351, 558/102, 558/132, 558/164, 558/186, 558/99, 558/165, 516/57, 516/908
• US Class Current: 516/57
• CPC Class Codes: C11D 1/78 Neutral esters of acids of phosphorus
• CPC Class Codes: G03G 9/0806 whereby chemical synthesis of at least one of the toner components takes place
• CPC Class Codes: Y10S 516/908 The compound contains repeating -OCnH2n-, i.e. repeating unsubstituted oxyalkylene

Abstract

A surfactant composition represented by Formulas (I), (II) or (III); or optionally mixtures thereof ##STR1## wherein R¹ is a hydrophobic moiety of alkyl or aryl, and wherein alkyl contains from about 4 to about 60 carbon atoms and aryl contains from about 6 to about 60 carbon atoms; R² is selected from the group consisting of alkyl and aryl, wherein alkyl contains from 1 to about 60 carbon atoms and aryl contains from about 6 to about 60; R³ is hydrogen or alkyl of from 1 to about 10 carbon atoms; A is a hydrophilic polymer chain; m is the number of repeating segments of the hydrophilic polymer chain and is a number of from about 2 to about 500.

Claims

1. A process for the preparation of nonionic surfactant compositions of Formula (I) ##STR24## wherein R¹ is a hydrophobic moiety of alkyl or aryl;

R² is selected from the group consisting of hydrogen, alkyl and aryl;

R³ is hydrogen or alkyl;

A is a hydrophilic polymer chain; and

m is the number of repeating segments of the hydrophilic polymer chain A comprising;

(A) reacting from about 1 to about 5 molar equivalents of a phosphorus oxyhalide with about 1 molar equivalent of a hydroxylic component R¹ OH (IV) at a temperature ranging from about 5°

C. to about 120°

C. to provide a dihalophosphate (VII) ##STR25## wherein R¹ is an alkyl or aryl, and X is a halide;

(B) reacting about 1 molar equivalent of a dihalophosphate (VII) with about 1 molar equivalent of an hydroxylic component R² OH (V) at a temperature ranging from about 0°

C. to about 80°

C. in an inert solvent and in the presence of a base to provide a halophosphate (VIII) ##STR26## wherein R¹ and R² are an alkyl or aryl, and X is a halide;

(C) reacting about 1 molar equivalent of a halophosphate (VIII) with about 1 molar equivalent of a hydrophilic polymer (VI) at a temperature ranging from 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base ##STR27## wherein R³ is an alkyl, A is a hydrophilic polymer chain with m representing the number of repeating segments;

or comprising

(A) reacting from about 1 to about 5 molar equivalents of a phosphorus oxyhalide with about 1 molar equivalent of a hydroxylic component (IV) R¹ OH at a temperature ranging from 5°

C. to about 120°

C. to provide a dihalophosphate (VII) ##STR28## wherein R¹ is an alkyl or aryl, and X is a halide;

(B) reacting about 1 molar equivalent of a dihalophosphate (VII) of (A) with about 1 molar equivalent of a hydrophilic polymer (VI) at a temperature ranging from about 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base to provide a halophosphate (IX) ##STR29## wherein R¹ is an alkyl or aryl, R³ is an alkyl, X is a halide, and A is a hydrophilic polymer chain with m representing the number of repeating segments; and

(C) reacting 1 molar equivalent of a halophosphate (IX) of (B) with about 1 molar equivalent of a hydroxylic component R² OH (V) at a temperature ranging from about 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base.

2. A process in accordance with claim 1 wherein (A) further comprises from 0.5 to about 5 molar percent of a metal catalyst.

3. A process in accordance with claim 2 wherein said metal catalyst is magnesium chloride.

4. A process in accordance with claim 1 wherein said inert solvent is a hydrocarbon or a halogenated hydrocarbon, and wherein said base is a tertiary amine.

5. A process for the preparation of nonionic surfactant compositions of Formula (III) ##STR30## wherein R¹ is a hydrophobic moiety of alkyl or aryl;

R² is selected from the group consisting of hydrogen, alkyl and aryl;

A is a hydrophilic polymer chain; and

m is the number of repeating segments of the hydrophilic polymer chain A comprising;

(A) reacting from about 1 to about 5 molar equivalents of a phosphorus oxyhalide with about 1 molar equivalent of a hydroxylic component (IV) R¹ OH at a temperature ranging from about 5°

C. to about 120°

C. to provide a dihalophosphate (VII) ##STR31## wherein R¹ is an alkyl or aryl, and X is a halide;

(B) reacting 1 molar equivalent of a dihalophosphate (VII) of (A) with from about 1 molar equivalent of a hydroxylic component R² OH (V) at a temperature ranging from about 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base to provide a halophosphate (VIII) ##STR32## wherein R¹ and R² are an alkyl or aryl, X is a halide; and

(C) reacting about 2 molar equivalents of a halophosphate (VIII) of (B) with 1 molar equivalent of a hydroxylic component (X) at a temperature ranging from 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base ##STR33## wherein A is a hydrophilic polymer chain with m representing the number of repeating segments.

6. A process for the preparation of nonionic surfactant compositions of Formula (II) ##STR34## wherein R¹ is a hydrophobic moiety of alkyl or aryl;

R³ is hydrogen or alkyl;

A is a hydrophilic polymer chain; and

m is the number of repeating segments of the hydrophilic polymer chain A comprising;

(A) reacting about 1 to about 5 molar equivalents of a phosphorus oxyhalide with about 1 molar equivalent of a hydroxylic component (IV) of the formula R¹ OH at a temperature ranging from about 5°

C. to about 120°

C. to provide a dihalophosphate (VII) ##STR35## wherein R¹ is an alkyl or aryl, and X is a halide; and

(B) reacting about 1 molar equivalent of a dihalophosphate (VII) as prepared in (A) with about 2 molar equivalents of a hydrophilic polymer component (VI) at a temperature ranging from about 0°

C. to about 80°

C. in an inert solvent, and in the presence of a base ##STR36## wherein R³ is an alkyl, and A is a hydrophilic polymer chain with m representing the number of repeating segments.

7. A process in accordance with claim 6 wherein (A) further comprises from about 0.5 to about 5 molar percent of a metal catalyst.

8. A process in accordance with claim 7 wherein said metal catalyst is magnesium chloride.

9. A process in accordance with claim 6 wherein said inert solvent is a hydrocarbon or a halogenated hydrocarbon;

and wherein said base is a tertiary amine.

10. A surfactant composition represented by Formulas (I), (II);

or optionally mixtures thereof ##STR37## wherein R¹ is a hydrophobic moiety of alkyl or aryl;

R² is selected from the group consisting of hydrogen, methyl and aryl;

R³ is hydrogen or methyl;

A is a hydrophilic polymer chain; and

m is the number of repeating segments of the hydrophilic polymer chain A.

11. A surfactant composition wherein said surfactant is selected from the group consisting of poly(ethylene glycol) methyl p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-methyl p-tert-octylphenyl phosphate, poly(ethylene glycol) methyl decylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-methyl dodecylphenyl phosphate, poly(ethyleneglycol) methyl dodecylphenyl phosphate, bis poly(ethylene glycol)-α

-methyl ether!-ω

-p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

,ω

-methyl p-tert-octylphenyl phosphate, poly(ethylene glycol) ethyl p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-ethyl p-tert-octylphenyl phosphate, poly(ethylene glycol) phenyl p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-phenyl p-tert-octylphenyl phosphate, poly(ethylene glycol) tolyl p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-tolyl p-tert-octylphenyl phosphate, and poly(ethylene oxide-co-propylene oxide) methyl p-tert-octylphenyl phosphate, wherein the polymer chain contains from about 5 to about 50 repeating units or segments.

12. A surfactant composition wherein said surfactant is selected from the group consisting of poly(ethylene glycol) methyl p-tert-octylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-methyl p-tert-octylphenyl phosphate, poly(ethylene glycol) methyl decylphenyl phosphate, poly(ethylene glycol)-α

-methyl ether-ω

-methyl dodecylphenyl phosphate, poly(ethylene glycol) methyl dodecylphenyl phosphate, bis poly(ethylene glycol)-α

-methyl ether!-ω

-p-tert-octylphenyl phosphate, and poly(ethylene glycol)-α

,ω

-methyl p-tert-octylphenyl phosphate.

13. The surfactants ##STR38## wherein m is about 17;

and ##STR39## wherein m is about 17.