Patent US3365983A successfully refreshed from Google Patents.
Patent US4113725A successfully refreshed from Google Patents.
US4113725A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Multifunctional additives
Assignee: Mobil Oil AS
•
Filing: 1975-04-03
•
Granted: 1978-09-12
•
Expires: 1995-04-03
Abstract
Abstract As a new class of multifunctional additives for industrial fluids, the compounds having the following general formula: ##STR1## IN WHICH EACH X and Y represents a heterocyclic nitrogen radical and may be the same or different for each occurrence of X and Y; Z is a basic nitrogen-containing radical; n is 0 or an integer of at least 1, preferably 1 to 10; and A, B, C, and D are linked groups derived from compounds which may provide desired functions, such as detergent, antioxidant, and antiwear properties, or indirectly useful functions, such as adsorbency. At least one of A, B, C, or D is amino or anilino or is derived from an alkenylsuccinimide or an alkyl lactam or tetrahydropyrrolidine, or alkyl-substituted Mannich base, having at least 8 carbon atoms in the alkenyl or alkyl radical, or combinations of any of these. The reaction between these products and metal compounds particularly alkali and alkaline earth metal compounds provides more improved properties.
Inventors
- 👤 John C. Nnadi
- 👤 Israel J. Heilweil
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-08 07:21
CPC Classifications
C; C10; C10M; C10M133/00; C10M133/52; C10M133/58; C10M133/02; C10M133/38; C10M2207/00; C10M2207/28; C10M2207/281; C10M2207/282; C10M2207/283; C10M2207/286; C10M2215/00; C10M2215/02; C10M2215/04; C10M2215/22; C10M2215/221; C10M2215/222; C10M2215/225; C10M2215/226; C10M2215/24; C10M2215/26; C10M2215/30; C10M2217/00; C10M2217/02; C10M2217/028; C10M2217/04; C10M2217/042; C10M2217/043; C10M2217/046; C10M2217/06; C10M2219/00; C10M2219/04; C10M2219/044; C10M2219/09; C10M2221/00; C10M2223/00; C10M2223/02; C10M2223/04; C10M2223/042; C10M2223/045; C10M2223/049; C10M2223/06; C10M2223/061; C10M2223/065; C10M2225/00; C10M2225/02; C10N; C10N2010/00; C10N2010/02; C10N2010/04; C10N2010/14; C10N2010/16; C10N2040/00; C10N2040/08; C10N2040/20; C10N2040/24; C10N2040/241; C10N2040/242; C10N2040/243; C10N2040/244; C10N2040/245; C10N2040/246; C10N2040/247; C10N2050/00; C10N2050/10; F; F02; F02B; F02B75/00; F02B75/02; F02B2075/022; F02B2075/027
Claims Analysis
Total Claims: 32
Claim 1
Independent Claim
179 words
A heterocyclic nitrogen compound selected from the class consisting of (a) a compound comprising two monovalent amine substituted mononuclear diazine nuclei in which each said monovalent amine substituent is bonded through an amino nitrogen atom to a carbon atom of one of said diazine nuclei, said diazine nuclei being linked one to the other through a bivalent amine radical bonded through an amino nitrogen atom to a carbon atom of each of said diazine nuclei; (b) a monovalent amine substituted mononuclear diazine in which said monovalent amine substituent is bonded through an amino nitrogen atom to a carbon atom of the diazine nucleus, the amine of said monovalent amine substituent being selected from the group consisting of: ##STR17## the amine of said bivalent amine radical being selected from the group consisting of: ##STR18## wherein: m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms.
Claim 2
Dependent Claim
179 words
A heterocyclic nitrogen compound selected from the class consisting of (a) a compound comprising two monovalent amine substituted mononuclear diazine nuclei in which each said monovalent amine substituent is bonded through an amino nitrogen atom to a carbon atom of one of said diazine nuclei, said diazine nuclei being linked one to the other through a bivalent amine radical bonded through an amino nitrogen atom to a carbon atom of each of said diazine nuclei; (b) a monovalent amine substituted mononuclear diazine in which said monovalent amine substituent is bonded through an amino nitrogen atom to a carbon atom of the diazine nucleus, the amine of said monovalent amine substituent being selected from the group consisting of: ##STR17## the amine of said bivalent amine radical being selected from the group consisting of: ##STR18## wherein: m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms.
Claim 3
Dependent Claim
92 words
The compound of claim 1 in which said heterocyclic nitrogen compound also includes at least one additional substituent bonded to a carbon atom of at least one of said diazine nuclei, said additional substituent being selected from the group consisting of (a) amino, anilino, alkyl amino and alkyl anilino radicals having from 1 to 100 carbon atoms bonded directly through an amino nitrogen to a carbon atom of at least one of said diazine nuclei; (b) N-phenyl-p-phenylene diamine; (c) 2-(2-aminoethylamino)-ethanol and (d) an alkyl group having from 1 to 100 carbon atoms.
Claim 4
Dependent Claim
58 words
The compound of claim 1 in which each of the diazine nuclei of compound (a) also includes at least one additional amine substituent bonded directly through an amino nitrogen to a carbon atom of each said diazine nucleus, said additional amine substituent selected from the group consisting of members (1) through (6) inclusive, as defined in claim 1.
Claim 5
Dependent Claim
12 words
The compound of claim 1 in which the diazine nucleus is pyrimidine.
Claim 6
Dependent Claim
43 words
The compound of claim 1 in which the diazine nucleus is pyrimidine and in which the amine of said monovalent and said bivalent amine radicals is a bis(alkenylsuccinimide)amine having the structure of member (2) of the group of amines defined in claim 1.
Claim 7
Dependent Claim
55 words
The compound of claim 1 in which the diazine nucleus is pyrimidine including an additional monovalent amine substituent bonded through an amino nitrogen to a carbon atom of said pyrimidine nucleus, the additional monovalent amine of said monovalent amine radical havig the structure of member (1) of the group of amines defined in claim 1.
Claim 8
Dependent Claim
36 words
A compound comprising the compound of claim 1 which has been reactively combined with from 0.005% to about 10% by weight, based upon the total weight of said composition, of an alkali or alkaline earth metal.
Claim 9
Dependent Claim
17 words
The compound of claim 7 including of from 0.005% to about 1% by weight of said metal.
Claim 10
Dependent Claim
28 words
A compound comprising a product of the reaction of the compound of claim 1 and an alkali or alkaline earth metal oxide, hydroxide, carbonate, carboxylate, alcoholate or phenolate.
Claim 11
Dependent Claim
68 words
A compound of the formula ##STR19## where A is a monovalent amine radical bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure ##STR20## wherein: m is an integer from 1 to 3; e is an integer from 1 to 10; and R is an alkenyl group containing from 8 to about 300 carbon atoms.
Claim 12
Dependent Claim
68 words
A compound of the formula ##STR19## where A is a monovalent amine radical bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure ##STR20## wherein: m is an integer from 1 to 3; e is an integer from 1 to 10; and R is an alkenyl group containing from 8 to about 300 carbon atoms.
Claim 13
Dependent Claim
68 words
A compound of the formula ##STR21## where A is a monovalent amine radical bonded through an amino nitrogen to a carbon of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure of ##STR22## wherein: m is an integer from 1 to 3; e is an integer from 1 to 10; and R is an alkenyl group containing from 8 to about 300 carbon atoms.
Claim 14
Dependent Claim
68 words
A compound of the formula ##STR21## where A is a monovalent amine radical bonded through an amino nitrogen to a carbon of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure of ##STR22## wherein: m is an integer from 1 to 3; e is an integer from 1 to 10; and R is an alkenyl group containing from 8 to about 300 carbon atoms.
Claim 15
Dependent Claim
135 words
A compound of the formula ##STR23## wherein A is a monovalent amine radical bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical being selected from the group consisting of ##STR24## wherein: m is an integer from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; R' is an alkyl group containing from 8 to about 300 carbon atoms, and B and D are members selected from the group consisting of (a) hydrogen; (b) A; (c) amino, anilino, alkyl amino and alkyl anilino radicals having from 1 to 100 carbon atoms; (d) N-phenyl-p-phenylene diamine; (e) 2-(2-aminoethylamino)-ethanol, and (f) an alkyl group having from 1 to 100 carbon atoms.
Claim 16
Dependent Claim
135 words
A compound of the formula ##STR23## wherein A is a monovalent amine radical bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical being selected from the group consisting of ##STR24## wherein: m is an integer from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; R' is an alkyl group containing from 8 to about 300 carbon atoms, and B and D are members selected from the group consisting of (a) hydrogen; (b) A; (c) amino, anilino, alkyl amino and alkyl anilino radicals having from 1 to 100 carbon atoms; (d) N-phenyl-p-phenylene diamine; (e) 2-(2-aminoethylamino)-ethanol, and (f) an alkyl group having from 1 to 100 carbon atoms.
Claim 17
Dependent Claim
43 words
The compound of claim 12 having the structure ##STR25## wherein n is an integer from 1 to 3; e is an integer from 1 to 10; R is a polybutenyl group; and R' is an alkyl group having up to 100 carbon atoms.
Claim 18
Dependent Claim
54 words
The compound of claim 12 having the structure ##STR26## where A, B and D are monovalent amine radicals bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of each said monovalent amine radical having the structure of member (2) of the group of amines defined in claim 12.
Claim 19
Dependent Claim
23 words
A compound comprising the compound of claim 14 which has been reactively combined with from 0.005% to about 1% of an alkali metal.
Claim 20
Dependent Claim
57 words
The compound of claim 12 having the structure ##STR27## where B is an amino group and A is a monovalent amine radical bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure of member (2) of the group of amines defined in claim 12.
Claim 21
Dependent Claim
23 words
A compound comprising the compound of claim 16 which has been reactively combined with from 0.005% to about 1% of an alkali metal.
Claim 22
Dependent Claim
54 words
The compound of claim 12 having the structure ##STR28## where A, B and D are monovalent amine radicals bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of each said monovalent amine radical having the structure of member (4) of the group of amines defined in claim 12.
Claim 23
Dependent Claim
54 words
The compound of claim 12 having the structure ##STR29## where A, B and D are monovalent amine radicals bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of each said monovalent amine radical having the structure of member (6) of the group of amines defined in claim 12.
Claim 24
Dependent Claim
66 words
The compound of claim 12 having the structure ##STR30## wherein A, B and D are monovalent amine radicals bonded through an amino nitrogen to a carbon atom of the pyrimidine ring, the amines of said monovalent amine radicals being selected from the group consisting of N-phenyl-p-phenylene diamine 2-(2-aminoethylamino)-ethanol, and an amine having the structure of member (2) of the group of amines defined in claim 12.
Claim 25
Dependent Claim
82 words
The compound of claim 12 having the structure ##STR31## where A is a monovalent amine radical bonded through an amino nitrogen to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure of member (2) of the group of amines defined in claim 12; B is NH 2 or a monovalent amine radical bonded through an amine nitrogen to a carbon atom of the pyrimidine ring, the amine of said amine radical being N-phenyl-p-phenylene diamine.
Claim 26
Dependent Claim
64 words
The compound of claim 12 having the structure ##STR32## where D is an alkyl group having from 1 to 100 carbon atoms, and A is a monovalent amine radical bonded through an amino nitrogen to a compound atom of the pyrimidine nucleus, the amine of said monovalent amine radical having the structure of member (2) of the group of amines defined in claim 12.
Claim 27
Dependent Claim
202 words
A compound of the formula ##STR33## wherein B is a monovalent amine radical bonded through an amino nitrogen atom to a carbon atom of each of said pyrimidine nuclei, the amine of said monovalent amine radical being selected from the group consisting of: ##STR34## D is selected from the group consisting of (a) hydrogen; (b) a monovalent amine radical substituent bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine raidical being selected from the group consisting of members (1) through (6) inclusive of the group of amines defined above; (c) amino, anilino, alkyl amino and alkyl anilino radicals having from 1 to 100 carbon atoms; (d) N-phenyl-p-phenylene diamine; (e) 2-(2-aminoethylamino)-ethanol, and (f) an alkyl group having from 1 to 100 carbon atoms A is selected from the group consisting of (7) --HN (C m H 2m NH) e-1 C m H 2m NH and ##STR35## wherein: m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms.
Claim 28
Dependent Claim
202 words
A compound of the formula ##STR33## wherein B is a monovalent amine radical bonded through an amino nitrogen atom to a carbon atom of each of said pyrimidine nuclei, the amine of said monovalent amine radical being selected from the group consisting of: ##STR34## D is selected from the group consisting of (a) hydrogen; (b) a monovalent amine radical substituent bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus, the amine of said monovalent amine raidical being selected from the group consisting of members (1) through (6) inclusive of the group of amines defined above; (c) amino, anilino, alkyl amino and alkyl anilino radicals having from 1 to 100 carbon atoms; (d) N-phenyl-p-phenylene diamine; (e) 2-(2-aminoethylamino)-ethanol, and (f) an alkyl group having from 1 to 100 carbon atoms A is selected from the group consisting of (7) --HN (C m H 2m NH) e-1 C m H 2m NH and ##STR35## wherein: m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms.
Claim 29
Dependent Claim
209 words
A compound of the formula ##STR36## wherein X and Y are mononuclear diazine nuclei, Z is a bivalent amine radical connected through an amino nitrogen to a carbon atom of each of diazine nuclei to which said Z is bonded, the amine of said bivalent amine radical being selected from the group consisting of: H 2 n (c m H 2m NH) e H and ##STR37## A is a monovalent amine substituent bonded through an amino nitrogen to a carbon atom of X, the amine of said monovalent amine substituent being selected from the group consisting of ##STR38## wherein: n is from 0 to 10 m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; R' is an alkyl group containing from 8 to about 300 carbon atoms, and B and D are selected from the group consisting of (a) hydrogen; (b) A; (c) alkyl, alkenyl, hydroxyalkyl, and alkyl carboxy radicals having from one to about 500 carbon atoms; (d) aralkyl, aryl, alkaryl and hydroxyaryl radicals having from 1 to about 100 carbon atoms; (e) carboxy, hydroxy, phosphono phosphato sulfonoto and mercapto radicals; (f) N-phenyl-p-phenylene diamine; (g) 2-(a-aminoethylamino)-ethanol.
Claim 30
Dependent Claim
209 words
A compound of the formula ##STR36## wherein X and Y are mononuclear diazine nuclei, Z is a bivalent amine radical connected through an amino nitrogen to a carbon atom of each of diazine nuclei to which said Z is bonded, the amine of said bivalent amine radical being selected from the group consisting of: H 2 n (c m H 2m NH) e H and ##STR37## A is a monovalent amine substituent bonded through an amino nitrogen to a carbon atom of X, the amine of said monovalent amine substituent being selected from the group consisting of ##STR38## wherein: n is from 0 to 10 m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; R' is an alkyl group containing from 8 to about 300 carbon atoms, and B and D are selected from the group consisting of (a) hydrogen; (b) A; (c) alkyl, alkenyl, hydroxyalkyl, and alkyl carboxy radicals having from one to about 500 carbon atoms; (d) aralkyl, aryl, alkaryl and hydroxyaryl radicals having from 1 to about 100 carbon atoms; (e) carboxy, hydroxy, phosphono phosphato sulfonoto and mercapto radicals; (f) N-phenyl-p-phenylene diamine; (g) 2-(a-aminoethylamino)-ethanol.
Claim 31
Dependent Claim
203 words
A compound of the formula ##STR39## wherein Z is a bivalent amine radical bonded through an amino nitrogen to a carbon atom of each of said heterocyclic nuclei, the amine of said bivalent amine radical being selected from the group consisting of H 2 n(c m H 2m NH) e H and ##STR40## B is a monovalent amine substituent bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus to which B is bonded, the amine of said monovalent amine substituent being selected from the group consisting of: ##STR41## wherein: n is from 0 to 10; m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms, D is selected from the group consisting (a) hydrogen (b) B; (c) alkyl, alkenyl, hydroxyalkyl and alkyl carboxy radicals having from 1 to about 100 carbon atoms; (d) aralkyl, aryl, alkaryl and hydroxyaryl radicals having from 1 to about 100 carbon atoms; (e) carboxy, hydroxy, phosphono, phosphato, sulfonato and mercapto radicals; (f) N-phenyl-p phenylene diamine; and (g) 2-(a-aminoethylamino)-ethanol.
Claim 32
Dependent Claim
203 words
A compound of the formula ##STR39## wherein Z is a bivalent amine radical bonded through an amino nitrogen to a carbon atom of each of said heterocyclic nuclei, the amine of said bivalent amine radical being selected from the group consisting of H 2 n(c m H 2m NH) e H and ##STR40## B is a monovalent amine substituent bonded through an amino nitrogen atom to a carbon atom of the pyrimidine nucleus to which B is bonded, the amine of said monovalent amine substituent being selected from the group consisting of: ##STR41## wherein: n is from 0 to 10; m is an integer of from 1 to 3; e is an integer of from 1 to 10; R is an alkenyl group containing from 8 to about 300 carbon atoms; and R' is an alkyl group containing from 8 to about 300 carbon atoms, D is selected from the group consisting (a) hydrogen (b) B; (c) alkyl, alkenyl, hydroxyalkyl and alkyl carboxy radicals having from 1 to about 100 carbon atoms; (d) aralkyl, aryl, alkaryl and hydroxyaryl radicals having from 1 to about 100 carbon atoms; (e) carboxy, hydroxy, phosphono, phosphato, sulfonato and mercapto radicals; (f) N-phenyl-p phenylene diamine; and (g) 2-(a-aminoethylamino)-ethanol.
References Cited (Backward Citations)
US2544071A
Cited
US2506351A
Cited
US2568876A
Cited
US3055896A
Cited
US3322763A
Cited
US3206407A
Cited
US3309345A
Cited
US3515603A
Cited
US3200076A
Cited
US3627749A
Cited
US3308101A
Cited
US3301823A
Cited
US3310557A
Cited
US3278428A
Cited
US3323893A
Cited
US3734909A
Cited
US3625936A
Cited
US3575705A
Cited
US3558611A
Cited
US3595639A
Cited
US3642787A
Cited
US3642720A
Cited
US3929765A
Cited
USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1981-09-11 | 1982-03-13 | 1982-09-12 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1985-09-11 | 1986-03-13 | 1986-09-12 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1989-09-11 | 1990-03-13 | 1990-09-12 | $7700.00 | Window Closed / Lapsed |