US4053428A
Expired / Lapsed
US
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Hydrocarbon-substituted methylol phenols
Assignee: Lubrizol Corp
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Filing: 1975-09-15
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Granted: 1977-10-11
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Expires: 1995-09-15
Abstract
Abstract Hydroxy aromatic compositions containing (a) a hydroxyl group bonded directly to a carbon of an aromatic nucleus, (b) a hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of an aromatic nucleus, (c) at least one methylol or lower hydrocarbyl substituted methylol substituent bonded directly to a carbon atom of an aromatic nucleus, and not having any alkylene linkages between carbon atoms of two aromatic nuclei are useful as additives for normally liquid fuels and lubricating oils. These hydroxy aromatic compositions are also useful as intermediates for preparing other additives for fuels and lubricants. Typical hydroxy aromatic compositions of the present invention are formed by reaction of formaldehyde with an alkenyl- or alkyl-substituted phenol wherein the alkyl or alkenyl substituent contains an average of about 50 carbon atoms.
Inventors
- 👤 John Francis Pindar
- 👤 Jerome Martin Cohen
- 👤 Charles Peterson Bryant
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 03:22
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/192; C10L1/198; C08; C08G; C08G14/00; C08G14/02; C08G14/04; C08G14/06; C10L1/20; C10L1/206; C10L1/22; C10L1/234; C10L1/238; C10L1/24; C10L1/2462; C10L1/2475; C10M; C10M129/00; C10M129/02; C10M129/04; C10M129/10; C09; C09K; C09K23/00; C09K23/16; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2205/028; C10M2205/06; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/026; C10M2207/04; C10M2207/046; C10M2207/10; C10M2207/12; C10M2207/121; C10M2207/123; C10M2207/125; C10M2207/129; C10M2207/22; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/30; C10M2207/302; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/086; C10M2209/10; C10M2209/101; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/106; C10M2209/107; C10M2209/108; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/02; C10M2211/022; C10M2211/04; C10M2211/042; C10M2211/06; C10M2211/08; C10M2213/00; C10M2213/02; C10M2213/06; C10M2213/062; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/042; C10M2215/044; C10M2215/06; C10M2215/062; C10M2215/10; C10M2215/102; C10M2215/14; C10M2215/16; C10M2215/18; C10M2215/20; C10M2215/202; C10M2215/22; C10M2215/221; C10M2215/222; C10M2215/223; C10M2215/224; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/022; C10M2217/023; C10M2217/024; C10M2217/028; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/02; C10M2219/022; C10M2219/024; C10M2219/04; C10M2219/044; C10M2219/046; C10M2219/06; C10M2219/062; C10M2219/064; C10M2219/066; C10M2219/068; C10M2219/08; C10M2219/082; C10M2219/083; C10M2219/086; C10M2219/087; C10M2219/089; C10M2219/10; C10M2219/102; C10M2219/104; C10M2219/106; C10M2227/00; C10M2227/06; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2020/00; C10N2020/01; C10N2030/00; C10N2030/08; C10N2040/00; C10N2040/02; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/06; C10N2040/12; C10N2040/13; C10N2040/135; C10N2040/20; C10N2040/25; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/26; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
114 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of a composition comprising at least one hydroxy aromatic compound having: a. at least one hydroxyl substituent bonded directly to a carbon atom of an aromatic moiety, Ar, b. at least one hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of the aromatic moiety, Ar, and c. at least one methylol or lower hydrocarbon-based substituted methylol substituent bonded directly to a carbon atom of the aromatic moeity, Ar, said compound containing no alkylene linkages between carbon atoms of two aromatic nuclei.
Claim 2
Dependent Claim
114 words
A fuel or lubricant composition containing a major proportion of a normally liquid fuel or a lubricating oil of lubricating viscosity and a minor proportion of a composition comprising at least one hydroxy aromatic compound having: a. at least one hydroxyl substituent bonded directly to a carbon atom of an aromatic moiety, Ar, b. at least one hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of the aromatic moiety, Ar, and c. at least one methylol or lower hydrocarbon-based substituted methylol substituent bonded directly to a carbon atom of the aromatic moeity, Ar, said compound containing no alkylene linkages between carbon atoms of two aromatic nuclei.
Claim 3
Dependent Claim
15 words
A composition as claimed in claim 1 wherein substituent (c) is methylol, -CH 2 OH.
Claim 4
Dependent Claim
47 words
A composition as claimed in claim 1 wherein hydrocarbon-based substituent (b) has no more than about 300 aliphatic carbon atoms and is derived from homopolymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms, and substituent (c) is at least one methylol substituent.
Claim 5
Dependent Claim
54 words
A composition as claimed in claim 1 wherein the hydroxy aromatic compound is of the general formula ##STR9## wherein R° is an alkyl substituent of about 50 to about 300 carbon atoms derived from polymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms and m is 1 or 0.
Claim 6
Dependent Claim
115 words
A composition as claimed in claim 1 wherein the hydroxy aromatic compound is made by reacting at a temperature up to about 160° C. (i) at least one phenol, naphthol, X-substituted phenol or X-substituted naphthol wherein X is selected from the group consisting of lower alkyl substituents, lower alkoxy substituents, lower alkyl mercapto substituents, fluorine atoms, chlorine atoms and nitro substituents wherein said (i) has a hydrocarbon-based substituent of at least 50 aliphatic carbon atoms and at least one unsubstituted aromatic ring carbon with (ii) formaldehyde or a functional equivalent thereof in the presence of an alkaline reagent selected from the group consisting of alkali metal and alkaline earth metal oxides, hydroxides and lower alkoxides.
Claim 7
Dependent Claim
109 words
An additive concentrate comprising at least one substantially inert, normally liquid organic solvent/diluent and about 20 to about 90 percent of a composition comprising at least one hydroxy aromatic compound having: a. at least one hydroxyl substituent bonded directly to a carbon atom of an aromatic moiety, Ar, b. at least one hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of the aromatic moiety, Ar, and c. at least one methylol or lower hydrocarbon-based substituted methylol substituent bonded directly to a carbon atom of the aromatic moiety, Ar, said compound containing no alkylene linkages between carbon atoms of two aromatic nuclei.
Claim 8
Dependent Claim
109 words
An additive concentrate comprising at least one substantially inert, normally liquid organic solvent/diluent and about 20 to about 90 percent of a composition comprising at least one hydroxy aromatic compound having: a. at least one hydroxyl substituent bonded directly to a carbon atom of an aromatic moiety, Ar, b. at least one hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms bonded directly to a carbon atom of the aromatic moiety, Ar, and c. at least one methylol or lower hydrocarbon-based substituted methylol substituent bonded directly to a carbon atom of the aromatic moiety, Ar, said compound containing no alkylene linkages between carbon atoms of two aromatic nuclei.
Claim 9
Dependent Claim
15 words
A concentrate as claimed in claim 6 wherein substituent (c) is methylol, --CH 2 OH.
Claim 10
Dependent Claim
48 words
A concentrate as claimed in claim 6 wherein hydrocarbon-based substituent (b) has no more than about 300 aliphatic carbon atoms and is derived from homopolymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms, and the substituent (c) is at least one methylol substituent.
Claim 11
Dependent Claim
54 words
A concentrate as claimed in claim 6 wherein the hydroxy aromatic compound is of the general formula ##STR10## wherein R° is an alkyl substituent of about 50 to about 300 carbon atoms derived from polymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms and m is 1 or 0.
Claim 12
Dependent Claim
115 words
A concentrate as claimed in claim 6 wherein the hydroxy aromatic compound is made by reacting at a temperature up to about 160° C. (i) at least one phenol, naphthol, X-substituted phenol or X-substituted naphthol wherein X is selected from the group consisting of lower alkyl substituents, lower alkoxy substituents, lower alkyl mercapto substituents, fluorine atoms, chlorine atoms and nitro substituents wherein said (i) has a hydrocarbon-based substituent of at least 50 aliphatic carbon atoms and at least one unsubstituted aromatic ring carbon with (ii) formaldehyde or a functional equivalent thereof in the presence of an alkaline reagent selected from the group consisting of alkali metal and alkaline earth metal oxides, hydroxides and lower alkoxides.
Claim 13
Dependent Claim
13 words
A composition as claimed in claim 1 wherein substituent (b) is purely hydrocarbyl.
Claim 14
Dependent Claim
13 words
A concentrate as claimed in claim 6 wherein substituent (b) is purely hydrocarbyl.
Claim 15
Dependent Claim
74 words
A composition as claimed in claim 1 wherein the hydroxy aromatic compound is of the general formula ##STR11## wherein Ar' is a benzene, naphthalene, X-substituted benzene or X-substituted naphthalene nucleus, n is 1 or 2, and R is a hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms, X being selected from the group consisting of lower alkyl substituents, lower alkoxy substituents, lower alkyl mercapto substituents, fluorine atoms, chlorine atoms and nitro substituents.
Claim 16
Dependent Claim
73 words
A concentrate as claimed in claim 6 wherein the hydroxy aromatic compound is of the general formula ##STR12## wherein Ar' is a benzene, naphthalene, X-substituted benzene or X-substituted naphthalene nucleus, n is 1 or 2, and R is a hydrocarbon-based substituent of at least about 50 aliphatic carbon atoms, X being selected from the group consisting of lower alkyl substituents, lower alkoxy substituents, lower mercapto substituents, fluorine atoms, chlorine atoms and nitro substituents.
Claim 17
Dependent Claim
12 words
A composition as claimed in claim 1 which is a fuel composition.
Claim 18
Dependent Claim
12 words
A composition as claimed in claim 4 which is a fuel composition.
Claim 19
Dependent Claim
12 words
A composition as claimed in claim 5 which is a fuel composition.
Claim 20
Dependent Claim
12 words
A composition as claimed in claim 1 which is a lubricant composition.
Claim 21
Dependent Claim
12 words
A composition as claimed in claim 4 which is a lubricant composition.
Claim 22
Dependent Claim
12 words
A composition as claimed in claim 5 which is a lubricant composition.
References Cited (Backward Citations)
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1980-10-10 | 1981-04-11 | 1981-10-11 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1984-10-10 | 1985-04-11 | 1985-10-11 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1988-10-10 | 1989-04-11 | 1989-10-11 | $7700.00 | Window Closed / Lapsed |