US4273891A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Hydrocarbon-substituted methylol phenols
Assignee: Lubrizol Corp
•
Filing: 1977-09-06
•
Granted: 1981-06-16
•
Expires: 1997-09-06
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 F. Pindar
- 👤 Jerome M. Cohen
- 👤 Charles P. Bryant
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-29 22:32
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/192; C10L1/198; C07; C07C; C07C37/00; C07C37/11; C07C37/115; C07C37/14; C07C37/18; C07C37/20; C07C39/00; C07C39/02; C07C39/11; C07C39/12; C07C39/14; C07C39/24; C07C39/26; C07C39/38; C08; C08G; C08G8/00; C08G8/04; C08G8/08; C10L1/20; C10L1/206; C10L1/22; C10L1/234; C10L1/238; C10L1/24; C10L1/2462; C10L1/2475; C10M; C10M129/00; C10M129/86; C10M129/88; C10M129/91; C10M145/00; C10M145/18; C10M145/20; C10M2203/00; C10M2203/02; C10M2203/022; C10M2203/024; C10M2203/04; C10M2203/06; C10M2205/00; C10M2205/02; C10M2205/024; C10M2205/026; C10M2205/028; C10M2207/00; C10M2207/02; C10M2207/023; C10M2207/024; C10M2207/026; C10M2207/04; C10M2207/046; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2207/34; C10M2207/40; C10M2207/402; C10M2207/404; C10M2209/00; C10M2209/02; C10M2209/10; C10M2209/101; C10M2209/103; C10M2209/104; C10M2209/105; C10M2209/106; C10M2209/108; C10M2209/109; C10M2209/11; C10M2209/111; C10M2211/00; C10M2211/02; C10M2211/022; C10M2211/04; C10M2211/042; C10M2211/06; C10M2213/00; C10M2213/02; C10M2213/06; C10M2213/062; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/06; C10M2215/062; C10M2215/20; C10M2215/202; C10M2215/22; C10M2215/221; 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; C10M2219/086; C10M2219/087; 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; C10M2227/04; C10M2229/00; C10M2229/04; C10M2229/042; C10M2229/043; C10M2229/044; C10M2229/05; C10N; C10N2030/00; C10N2030/08; C10N2040/00; C10N2040/04; C10N2040/042; C10N2040/044; C10N2040/046; C10N2040/06; C10N2040/08; C10N2040/12; C10N2040/13; C10N2040/20; C10N2040/25; C10N2040/252; C10N2040/253; C10N2040/255; C10N2040/26; C10N2050/00; C10N2050/10; C10N2070/00; C10N2070/02
Claims Analysis
Total Claims: 17
Claim 1
Independent Claim
119 words
A lubricant and liquid fuel additive or intermediate for such additives selected from the group consisting of (I) hydroxy aromatic compounds 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 and up to about 300 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, (II) ether condensates of said hydroxy aromatic compounds and mixtures of (I) and (II).
Claim 2
Dependent Claim
119 words
A lubricant and liquid fuel additive or intermediate for such additives selected from the group consisting of (I) hydroxy aromatic compounds 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 and up to about 300 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, (II) ether condensates of said hydroxy aromatic compounds and mixtures of (I) and (II).
Claim 3
Dependent Claim
22 words
An additive or intermediate as claimed in claim 1 wherein the hydrocarbon-based substituent has no more than about 300 aliphatic carbon atoms.
Claim 4
Dependent Claim
20 words
An additive or intermediate as claimed in claim 1 wherein the substituent (c) is a methylol substituent, CH 2 OH.
Claim 5
Dependent Claim
31 words
An additive or intermediate as claimed in claim 2 wherein the hydrocarbon-based substituent (b) is derived from homopolymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms.
Claim 6
Dependent Claim
25 words
An additive or intermediate as claimed in claim 4 wherein said monoolefin contains predominantly isobutene and the substituent (c) is at least one methylol substituent.
Claim 7
Dependent Claim
77 words
An additive or intermediate as claimed in claim 1 wherein the hydroxy aromatic compounds (I) are represented by the general formula ##STR9## 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 8
Dependent Claim
36 words
An additive or intermediate as claimed in claim 6 wherein R has up to about 300 carbon atoms and is derived from homopolymerization or interpolymerization of at least one 1-monoolefin of 2 to 10 carbon atoms.
Claim 9
Dependent Claim
58 words
An additive or intermediate as claimed in claim 7 wherein the hydroxy aromatic compounds (I) are represented by 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 monoolefin of 2 to 10 carbon atoms, and m is 1 or 0.
Claim 10
Dependent Claim
69 words
An additive or intermediate as claimed in claim 1 made by reacting at a temperature up to about 160° C. at least one hydroxy aromatic compound having a hydrocarbon-based substituent of at least 50 and up to about 300 aliphatic carbon atoms, and at least one unsubstituted aromatic ring carbon, with formaldehyde or a lower hydrocarbon substituted formaldehyde or functional equivalent thereof in the presence of an alkaline reagent.
Claim 11
Dependent Claim
40 words
An additive or intermediate as claimed in claim 9 wherein formaldehyde or a functional equivalent thereof is used and the alkaline reagent is selected from the group consisting of alkali metal and alkaline earth metal oxides, hydroxides and lower alkoxides.
Claim 12
Dependent Claim
48 words
An additive or intermediate as claimed in claim 10 wherein the hydroxy aromatic compound is phenol, naphthol, X-substituted phenol or X-substituted naphthol and 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.
Claim 13
Dependent Claim
26 words
An additive or intermediate as claimed in claim 8 wherein R° is an alkyl group of at least about 80 carbons containing predominantly isobutane repeat units.
Claim 14
Dependent Claim
111 words
A lubricant and liquid fuel additive or intermediate for such additives selected from the group consisting of (I) hydroxy aromatic compounds which can be represented by the general formula ##STR11## wherein x, z and g are each at least one; y' is 0 or at least one, the sum of x, y', z and g does not exceed the available valences of Ar; each R' is hydrogen or a hydrocarbon-based substituent of up to seven carbon atoms and each R is a hydrocarbon-based substituent of at least about 50 and up to about 300 aliphatic carbon atoms, (II) ether condensates of said hydroxy aromatic compounds and mixtures of (I) and (II).
Claim 15
Dependent Claim
111 words
A lubricant and liquid fuel additive or intermediate for such additives selected from the group consisting of (I) hydroxy aromatic compounds which can be represented by the general formula ##STR11## wherein x, z and g are each at least one; y' is 0 or at least one, the sum of x, y', z and g does not exceed the available valences of Ar; each R' is hydrogen or a hydrocarbon-based substituent of up to seven carbon atoms and each R is a hydrocarbon-based substituent of at least about 50 and up to about 300 aliphatic carbon atoms, (II) ether condensates of said hydroxy aromatic compounds and mixtures of (I) and (II).
Claim 16
Dependent Claim
79 words
An additive or intermediate as claimed in claim 13 wherein the hydroxy aromatic compounds (I) are represented by the formula ##STR12## and the ether condensate (II) is represented by the formula ##STR13## wherein Ar is a benzene, naphthalene, X-substituted benzene or X-substituted naphthalene nucleus, X being selected from the group consisting of lower alkyl substituents, lower alkoxy substituents, lower mercapto substituents, fluorine atoms, chlorine atoms and nitro substituents, and q is a number ranging from 2 to about 10.
Claim 17
Dependent Claim
62 words
An additive or intermediate as claimed in claim 14 wherein the hydroxy aromatic compounds (I) are para alkyl phenol-formaldehyde reaction products which are represented by the formula ##STR14## wherein m is 1 or zero and R" is an alkyl group of at least 50 and up to about 300 carbon atoms and the ether condensate (II) is represented by the formula ##STR15##
References Cited (Backward Citations)
US3127251A
Cited
CA738028A
Cited
GB502080A
Cited
US2163637A
Cited
GB634960A
Cited
US2707715A
Cited
US2796423A
Cited
US2912395A
Cited
US2962442A
Cited
US3211804A
Cited
US3539646A
Cited
US3306938A
Cited
US3501527A
Cited
US3336226A
Cited
US3981929A
Cited
US3637430A
Cited
GB1278582A
Cited
US3737465A
Cited
US3703494A
Cited
US4038327A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1984-06-15 | 1984-12-15 | 1985-06-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1988-06-15 | 1988-12-15 | 1989-06-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1992-06-15 | 1992-12-15 | 1993-06-16 | $7700.00 | Window Closed / Lapsed |