US4888437A
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Alkyl hydroxyalkyl phosphoric acid esters
Assignee: Henkel AG and Co KGaA
•
Filing: 1987-07-02
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Granted: 1989-12-19
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Expires: 2007-07-02
Abstract
Abstract Alkyl hydroxyalkyl orthophosphoric acid esters, particularly mixtures thereof, corresponding to the following formula ##STR1## in which R 1 and R 2 represent C 6 -C 22 alkyl groups and R 3 is hydrogen, a group R 1 or a group --CH 2 --CH(OH)--R 2 . The esters are prepared by reaction of phosphorus pentoxide with fatty alcohol and reaction of the phosphoric acid partial esters formed with long-chain α-epoxides. After conversion of the compounds corresponding to formula I, in which R 3 is hydrogen, into the salt form, the new alkyl hydroxyalkyl orthophosphoric acid ester mixtures are particularly suitable as emulsifiers for oil-water emulsion.
Inventors
- 👤 Ulrich Zeidler
- 👤 Alfred Meffert
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 04:21
CPC Classifications
C; C09; C09K; C09K23/00; C09K23/14; A; A61; A61K; A61K8/00; A61K8/02; A61K8/04; A61K8/06; A61K8/062; A61K8/18; A61K8/30; A61K8/55; A61Q; A61Q19/00; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C07F9/09; C07F9/091
Claims Analysis
Total Claims: 21
Claim 1
Independent Claim
41 words
An alkyl hydroxyalkyl orthophosphoric acid ester having the formula ##STR7## in which R 1 and R 2 is an alkyl group having from 6 to 22 carbon atoms and R 3 is hydrogen, R 1 or --CH 2 --CH(OH)R 2 .
Claim 2
Dependent Claim
41 words
An alkyl hydroxyalkyl orthophosphoric acid ester having the formula ##STR7## in which R 1 and R 2 is an alkyl group having from 6 to 22 carbon atoms and R 3 is hydrogen, R 1 or --CH 2 --CH(OH)R 2 .
Claim 3
Dependent Claim
48 words
A mixture of alkyl hydroxyalkyl orthophosphoric acid esters having the formula ##STR8## in which R 1 and R 2 are alkyl groups having from 6 to 22 carbon atoms and R 3 is selected from the group consisting of hydrogen, R 1 and --CH 2 --CH(OH)R 2 .
Claim 4
Dependent Claim
48 words
A mixture of alkyl hydroxyalkyl orthophosphoric acid esters having the formula ##STR8## in which R 1 and R 2 are alkyl groups having from 6 to 22 carbon atoms and R 3 is selected from the group consisting of hydrogen, R 1 and --CH 2 --CH(OH)R 2 .
Claim 5
Dependent Claim
11 words
A salt of the mixture of esters defined in claim 2.
Claim 6
Dependent Claim
43 words
A salt as defined in claim 3 in which said salt is selected from the group consisting of an alkali metal, an amine salt, an ammonium salt and an alkanolamine salt in which the alkanol group contains from 1 to 12 carbon atoms.
Claim 7
Dependent Claim
17 words
A salt as defined in claim 4 in which said salt is the dimethyl ethanol ammonium salt.
Claim 8
Dependent Claim
30 words
A mixture of esters as defined in claim 2 wherein R 1 and R 2 are alkyl groups having from 10 to 18 carbon atoms and R 3 is hydrogen.
Claim 9
Dependent Claim
19 words
A mixture of esters as defined in claim 6 wherein R 1 and R 2 are different alkyl groups.
Claim 10
Dependent Claim
34 words
A mixture of esters as defined in claim 2 wherein R 1 and R 2 are alkyl groups having from 10 to 18 carbon atoms and R 3 is --CH 2 --CH(OH)R 2 .
Claim 11
Dependent Claim
20 words
A mixture of esters as defined in claim 8 in which R 1 and R 2 are different alkyl groups.
Claim 12
Dependent Claim
22 words
A mixture of esters as defined in claim 2 having an acid number in the range of about 70 to about 175.
Claim 13
Dependent Claim
128 words
A process for preparing alkyl hydroxyalkyl orthophosphoric acid esters comprising the steps of: (a) reacting phosphorus pentoxide with a fatty alcohol of the formula R 1 OH in which R 1 is an alkyl group having from 6 to 22 carbon atoms to provide a mixture of phosphoric acid esters of said fatty alcohol, and (b) subsequently reacting said mixture of phosphoric acid esters of step (a) with an epoxide of the formula ##STR9## where R 2 is an alkyl group having 6 to 22 carbon atoms, thereby providing a mixture of alkyl hydroxyalkyl esters of the formula ##STR10## where R 1 and R 2 are as defined above and R 3 is selected from the group consisting of hydrogen, R 1 and --CH 2 --CH(OH)R 2 .
Claim 14
Dependent Claim
128 words
A process for preparing alkyl hydroxyalkyl orthophosphoric acid esters comprising the steps of: (a) reacting phosphorus pentoxide with a fatty alcohol of the formula R 1 OH in which R 1 is an alkyl group having from 6 to 22 carbon atoms to provide a mixture of phosphoric acid esters of said fatty alcohol, and (b) subsequently reacting said mixture of phosphoric acid esters of step (a) with an epoxide of the formula ##STR9## where R 2 is an alkyl group having 6 to 22 carbon atoms, thereby providing a mixture of alkyl hydroxyalkyl esters of the formula ##STR10## where R 1 and R 2 are as defined above and R 3 is selected from the group consisting of hydrogen, R 1 and --CH 2 --CH(OH)R 2 .
Claim 15
Dependent Claim
47 words
A process as defined in claim 11 in which at least 2 moles of said fatty alcohol are reacted with 1 mole of said phosphorus pentoxide and the resulting mixture of phosphoric acid esters from step (a) are reacted with 0.5 to 3 moles of said epoxide.
Claim 16
Dependent Claim
29 words
A process as defined in claim 12 in which from 0.5 to 2 moles of said epoxide are reacted with the mixture of phosphoric acid esters from step (a).
Claim 17
Dependent Claim
24 words
A process as defined in claim 12 in which 3 moles of said fatty alcohol is reacted with 1 mole of said phosphorus pentoxide.
Claim 18
Dependent Claim
20 words
A process as defined in claim 14 in which said fatty alcohol is a mixture of lauryl and myristyl alcohols.
Claim 19
Dependent Claim
18 words
A process as defined in claim 15 in which said epoxide is a mixture of 1-epoxydodecane and 1-epoxytetradecane.
Claim 20
Dependent Claim
18 words
A process as defined in claim 15 in which said epoxide is a mixture of 1-epoxyhexadecane and 1-epoxyoctadecane.
Claim 21
Dependent Claim
52 words
A process as defined in claim 11 in which the reaction in step (a) is conducted at a temperature in the range of from about 70° to about 100° C. and the reaction in step (b) is conducted at a temperature in the range of from about 70° to about 120° C.
References Cited (Backward Citations)
DE1812849A1
Cited
US4258448A
Cited
US4382042A
Cited
US4350645A
Cited
FR2517985A1
Cited
US4736051A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1992-12-18 | 1993-06-19 | 1993-12-19 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1996-12-18 | 1997-06-19 | 1997-12-19 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2000-12-18 | 2001-06-19 | 2001-12-19 | $7700.00 | Window Closed / Lapsed |