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US4194886A
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Haloalkyl hydroxy-aromatic condensation products as fuel additives
Assignee: Lubrizol Corp
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Filing: 1979-02-05
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Granted: 1980-03-25
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Expires: 1999-02-05
Abstract
Abstract Condensation products made by reacting an alpha-haloalkyl hydroxy-aromatic compound also having at least one non-fused hydrocarbyl substituent with at least one olefinic nitrile, carboxylic acid or carboxylic acid derivative are useful as additives for fuels and lubricants. The number of carbon atoms in the aromatic hydrocarbyl compound's substituents are each about 25 while the haloalkyl group contains from one to about 36 carbons. The acid or nitrile reactant usually contains three to about forty carbons. Products made from halomethyl alkyl-substituted phenols and α,β-olefinic diacid derivatives such as maleic anhydride are particularly useful. Similarly useful products can be made from these condensation products by further reacting their acid, acid derivative or nitrile groups with alcohols, polyols, monoamines, polyamines, metal salts or metals.
Inventors
- 👤 David E. Ripple
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 12:30
CPC Classifications
C; C10; C10M; C10M159/00; C10M159/12; C08; C08F; C08F8/00; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/1817; C10L1/22; C10L1/221; C10M1/00; C10M1/08; C10M2203/00; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/287; C10M2207/289; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/02; C10M2209/10; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/04; C10M2211/042; C10M2211/044; C10M2211/06; C10M2213/00; C10M2213/02; C10M2213/06; C10M2213/062; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/044; C10M2215/06; C10M2215/068; C10M2215/16; C10M2215/18; C10M2215/20; C10M2215/202; C10M2215/22; C10M2215/221; C10M2215/223; C10M2215/224; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/30; C10M2217/00; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/08; C10M2219/082; C10M2219/087; C10M2219/088; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/041; C10M2223/042; C10M2223/06; C10M2223/065; C10M2227/00; C10M2227/02; C10M2229/00; C10M2229/04; C10M2229/041; C10M2229/042; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/06; C10N2010/08; C10N2010/10; C10N2010/12; C10N2010/14; C10N2010/16; C10N2020/00; C10N2020/01; C10N2040/00; C10N2040/02; C10N2040/08; C10N2040/20; C10N2040/25; C10N2040/251; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/26; C10N2040/28; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 8
Claim 1
Independent Claim
268 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor cleaning or anti-screen clogging amount of a product made by the process comprising reacting at a temperature ranging from 100° C. to about 300° C. (A) at least one alpha haloalkyl aromatic compound of the general formula ##STR21## wherein Ar is a hydrocarbyl aromatic nucleus of 6 to about 30 carbon atoms, or a substituted analog of such an aromatic nucleus substituted with one or more up to 3 each of lower alkoxy, lower alkylthio, chloro, or nitro substituents, each R is a nonfused hydrocarbyl group of about 25 to about 700 carbon atoms, X is a halogen atom, each R' is independently a hydrogen atom, an alkyl group of 1 to 36 carbon atoms, or a halogen-substituted alkyl group of 1 to about 36 carbon atoms, n is 1 to 3 and m is 1 to 5 with the provisos that (i) the total number of carbon atoms in both the R' groups does not exceed 36 and (ii) where m exceeds 1, one of the R groups can also be ##STR22## group, with (B) at least one alpha-beta olefinically unsaturated compound selected from the group consisting of C 2-40 hydrocarbyl nitriles, C 2-40 hydrocarbyl carboxylic acids and anhydrides, esters, amides and ammonium and metal salts of said C 2-40 carboxylic acids; the ratio of (A) to (B) is between about 0.5:1 to about 2:1, the reaction of (A) with (B) resulting in the formation of a carbon-to-carbon bond, said bond including the carbon of at least one ##STR23## group.
Claim 2
Dependent Claim
268 words
A fuel composition comprising a major amount of a normally liquid fuel and a minor but carburetor cleaning or anti-screen clogging amount of a product made by the process comprising reacting at a temperature ranging from 100° C. to about 300° C. (A) at least one alpha haloalkyl aromatic compound of the general formula ##STR21## wherein Ar is a hydrocarbyl aromatic nucleus of 6 to about 30 carbon atoms, or a substituted analog of such an aromatic nucleus substituted with one or more up to 3 each of lower alkoxy, lower alkylthio, chloro, or nitro substituents, each R is a nonfused hydrocarbyl group of about 25 to about 700 carbon atoms, X is a halogen atom, each R' is independently a hydrogen atom, an alkyl group of 1 to 36 carbon atoms, or a halogen-substituted alkyl group of 1 to about 36 carbon atoms, n is 1 to 3 and m is 1 to 5 with the provisos that (i) the total number of carbon atoms in both the R' groups does not exceed 36 and (ii) where m exceeds 1, one of the R groups can also be ##STR22## group, with (B) at least one alpha-beta olefinically unsaturated compound selected from the group consisting of C 2-40 hydrocarbyl nitriles, C 2-40 hydrocarbyl carboxylic acids and anhydrides, esters, amides and ammonium and metal salts of said C 2-40 carboxylic acids; the ratio of (A) to (B) is between about 0.5:1 to about 2:1, the reaction of (A) with (B) resulting in the formation of a carbon-to-carbon bond, said bond including the carbon of at least one ##STR23## group.
Claim 3
Dependent Claim
13 words
A composition as claimed in claim 1 wherein n is 1 or 2.
Claim 4
Dependent Claim
13 words
A composition as claimed in claim 2 wherein Ar is a benzene nucleus.
Claim 5
Dependent Claim
23 words
A composition as claimed in claim 1 or 3 wherein each R is a homo- or interpolymer of ethylene, propylene, butylene or isobutylene.
Claim 6
Dependent Claim
24 words
A composition as claimed in claim 1, 2, 3 or 4 wherein both R' groups are hydrogen atoms and X is a chlorine atom.
Claim 7
Dependent Claim
17 words
A composition as claimed in claim 1, 2, or 5 wherein (B) is an acid or anhydride.
Claim 8
Dependent Claim
12 words
A composition as claimed in claim 6 wherein (B) is maleic anhydride.
References Cited (Backward Citations)
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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) | 1983-03-25 | 1983-09-24 | 1984-03-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-03-25 | 1987-09-24 | 1988-03-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-03-25 | 1991-09-24 | 1992-03-25 | $7700.00 | Window Closed / Lapsed |