US4244827A
Expired / Lapsed
US
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Mixture of di- or trithiophosphoric acid diesters, processes for producing it and its use
Assignee: BASF Corp
•
Filing: 1978-01-24
•
Granted: 1981-01-13
•
Expires: 1998-01-24
Abstract
Abstract Mixtures of di- or trithiophosphoric acid diesters produced from 1,2-diols or 1-mercapto-2-hydroxy compounds by reaction with P 2 S 5 are excellent stabilizing additives for lubricants.
Inventors
- 👤 Klaus P. Michaelis
- 👤 Hermann O. Wirth
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-02 15:58
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/16; C07F9/165; C10; C10M; C10M137/00; C10M137/02; C10M137/04; C10M137/10; C10M2203/00; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/026; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/025; C10M2207/026; C10M2207/028; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/123; C10M2207/129; C10M2207/16; C10M2207/22; C10M2207/28; C10M2207/283; C10M2207/284; C10M2207/285; C10M2207/287; C10M2207/289; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/084; C10M2211/00; C10M2211/08; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/044; C10M2215/06; C10M2215/064; C10M2215/065; C10M2215/066; C10M2215/08; C10M2215/082; C10M2215/086; C10M2215/14; C10M2215/22; C10M2215/221; C10M2215/223; C10M2215/224; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/28; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/06; C10M2219/062; C10M2219/066; C10M2219/068; C10M2219/08; C10M2219/082; C10M2219/084; C10M2219/085; C10M2219/086; C10M2219/087; C10M2219/089; C10M2219/09; C10M2219/10; C10M2219/104; C10M2219/108; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/043; C10M2223/045; C10M2223/047; C10M2229/00; C10M2229/02; C10M2229/04; C10M2229/05; C10N; C10N2010/00; C10N2010/04; C10N2010/08; C10N2010/10; C10N2010/12
Claims Analysis
Total Claims: 38
Claim 1
Independent Claim
191 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR17## wherein Y represents the groups ##STR18## n represents a value of 0.5 to 10, both X's independently of one another represent an oxygen atom or sulfur atom, and R represents linear or branched alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulfur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl of 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 mol of phosphorus pentasulfide per mole of OH or SH groups of compounds I, II or III, at 0° to 150° C.; and adding and neutralizing at 20°-40° C. the product of (a) and (b) with (c) sufficient ammonia; or primary, secondary or tertiary amine to neutralize the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding ammonium salt.
Claim 2
Dependent Claim
191 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR17## wherein Y represents the groups ##STR18## n represents a value of 0.5 to 10, both X's independently of one another represent an oxygen atom or sulfur atom, and R represents linear or branched alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulfur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl of 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 mol of phosphorus pentasulfide per mole of OH or SH groups of compounds I, II or III, at 0° to 150° C.; and adding and neutralizing at 20°-40° C. the product of (a) and (b) with (c) sufficient ammonia; or primary, secondary or tertiary amine to neutralize the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding ammonium salt.
Claim 3
Dependent Claim
11 words
Product according to claim 1 wherein X represents an oxygen atom.
Claim 4
Dependent Claim
14 words
Product according to claim 1 wherein n represents a value of 0.5 to 4.
Claim 5
Dependent Claim
14 words
Product according to claim 2 wherein n represents a value of 1 to 2.
Claim 6
Dependent Claim
15 words
Product according to claim 1 wherein R represents alkyl of 1 to 24 carbon atoms.
Claim 7
Dependent Claim
16 words
Product according to claim 5 wherein R is branched alkyl of 4 to 18 carbon atoms.
Claim 8
Dependent Claim
31 words
Product according to claim 1 wherein the amine contains at least one hydrocarbon group which is optionally interrupted by oxygen or sulfur atoms and which contains 6 to 24 carbon atoms.
Claim 9
Dependent Claim
15 words
Product according to claim 7 wherein the hydrocarbon group contains 8 to 18 carbon atoms.
Claim 10
Dependent Claim
17 words
Product according to claim 1 wherein component (a) consists of a compound of formula I or II.
Claim 11
Dependent Claim
23 words
Product according to claim 9 wherein R in formula I or II represents i-octyl, X represents an oxygen atom and n represents 1.
Claim 12
Dependent Claim
18 words
Product according to claim 10 wherein the ammonium salt is derived from an aliphatic primary or secondary amine.
Claim 13
Dependent Claim
15 words
Product according to claim 9 wherein component (a) consists of a compound of formula I.
Claim 14
Dependent Claim
32 words
A lubricant composition which comprises a mineral oil, a synthetic oil or mixture thereof, and from 0.01 to 5% by weight relevant to the lubricant of a product according to claim 1.
Claim 15
Dependent Claim
191 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR19## wherein Y represents the groups ##STR20## n represents a value of 0.5 to 10, both X's independently of one another represent an oxygen atom or sulphur atom, and R represents linear or branched alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulphur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 mol of phosphorus pentasulfide per mol of OH or SH groups of compounds I, II or III, at 0° to 150° C.; and adding and neutralizing at 20°-110° C. the product of (a) and (b) with (c) sufficient metal oxide, metal hydroxide or metal acetate to react with the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding metal salt.
Claim 16
Dependent Claim
191 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR19## wherein Y represents the groups ##STR20## n represents a value of 0.5 to 10, both X's independently of one another represent an oxygen atom or sulphur atom, and R represents linear or branched alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulphur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 mol of phosphorus pentasulfide per mol of OH or SH groups of compounds I, II or III, at 0° to 150° C.; and adding and neutralizing at 20°-110° C. the product of (a) and (b) with (c) sufficient metal oxide, metal hydroxide or metal acetate to react with the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding metal salt.
Claim 17
Dependent Claim
11 words
Product according to claim 14 wherein X represents an oxygen atom.
Claim 18
Dependent Claim
14 words
Product according to claim 14 wherein n represents a value of 0.5 to 4.
Claim 19
Dependent Claim
14 words
Product according to claim 16 wherein n represents a value of 1 to 2.
Claim 20
Dependent Claim
15 words
Product according to claim 14 wherein R represents alkyl of 1 to 24 carbon atoms.
Claim 21
Dependent Claim
16 words
Product according to claim 18 wherein R is branched alkyl of 4 to 18 carbon atoms.
Claim 22
Dependent Claim
17 words
Product according to claim 14 wherein the metal salts are barium, calcium, titanium, zinc, molybdenum or molybdenyl.
Claim 23
Dependent Claim
17 words
Product according to claim 14 wherein component (a) consists of a compound of formula I or II.
Claim 24
Dependent Claim
23 words
Product according to claim 21 wherein R in formula I or II represents i-octyl, X represents an oxygen atom and n represents 1.
Claim 25
Dependent Claim
15 words
Product according to claim 21 wherein component (a) consists of a compound of formula I.
Claim 26
Dependent Claim
32 words
A lubricant composition which comprises a mineral oil, a synthetic oil or mixture thereof, and from 0.01 to 5% by weight relevant to the lubricant of a product according to claim 14.
Claim 27
Dependent Claim
193 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR21## wherein Y represents the groups ##STR22## n represents a value from 0.5 to 10, both X's independently of one another represent an oxygen atom or sulfur atom, and R represents linear or brached alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulphur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl of 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 of phosphorus pentasulfide per mol of OH or SH groups of compounds I, II or III, at 0° to 150° C. and adding and reacting at 80°-90° C. the product of (a) and (b) with (c) sufficient olefin, alkyl halide, cycloalkyl halide, epoxy or epithio compound to react with the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding thiolthionophosphoric ester.
Claim 28
Dependent Claim
193 words
A product obtained by reacting (a) a compound of the general formula I, II or III or mixtures thereof ##STR21## wherein Y represents the groups ##STR22## n represents a value from 0.5 to 10, both X's independently of one another represent an oxygen atom or sulfur atom, and R represents linear or brached alkyl of 1 to 30 carbon atoms; said alkyl interrupted by oxygen or sulphur; cycloalkyl of 5 to 12 carbon atoms; cycloalkylalkyl of 5 to 12 carbon atoms in the cycloalkyl ring; phenyl; benzyl; or said cycloalkyl, said cycloalkylalkyl, said phenyl or said benzyl substituted by 1 or 2 alkyl groups having 1 to 12 carbon atoms, with (b) phosphorus pentasulfide; in a molar ratio of 1/4 of phosphorus pentasulfide per mol of OH or SH groups of compounds I, II or III, at 0° to 150° C. and adding and reacting at 80°-90° C. the product of (a) and (b) with (c) sufficient olefin, alkyl halide, cycloalkyl halide, epoxy or epithio compound to react with the free acidic PSH groups formed by the reaction of phosphorus pentasulfide with compounds I, II or III to give the corresponding thiolthionophosphoric ester.
Claim 29
Dependent Claim
11 words
Product according to claim 25 wherein X represents an oxygen atom.
Claim 30
Dependent Claim
14 words
Product according to claim 25 wherein n represents a value of 0.5 to 4.
Claim 31
Dependent Claim
14 words
Product according to claim 27 wherein n represents a value of 1 to 2.
Claim 32
Dependent Claim
15 words
Product according to claim 25 wherein R represents alkyl of 1 to 24 carbon atoms.
Claim 33
Dependent Claim
16 words
Product according to claim 29 wherein R is branched alkyl of 4 to 18 carbon atoms.
Claim 34
Dependent Claim
22 words
Product according to claim 25 wherein the olefin, alkyl halide, cycloalkyl halide, epoxy or epithio compound contains 2 to 20 carbon atoms.
Claim 35
Dependent Claim
17 words
Product according to claim 25 wherein component (a) consists of a compound of formula I or II.
Claim 36
Dependent Claim
23 words
Product according to claim 53 wherein R in formula I or II represents i-octyl, X represents an oxygen atom and n represents 1.
Claim 37
Dependent Claim
15 words
Product according to claim 32 wherein component (a) consists of a compound of formula I.
Claim 38
Dependent Claim
32 words
A lubricant composition which comprises a mineral oil, a synthetic oil or mixture thereof, and from 0.01 to 5% by weight relevant to the lubricant of a product according to claim 25.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-01-13 | 1984-07-14 | 1985-01-13 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-01-13 | 1988-07-14 | 1989-01-13 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-01-13 | 1992-07-14 | 1993-01-13 | $7700.00 | Window Closed / Lapsed |