US4235730A
Expired / Lapsed
US
⏱️ 0.0 years remaining
Polyurethanes and use thereof in lubricants and fuels
Assignee: Afton Chemical Additives Corp
•
Filing: 1978-12-28
•
Granted: 1980-11-25
•
Expires: 1998-12-28
Abstract
Abstract A polyurethane which is a reaction product of a diisocyanate and a diol. The polyurethane product is useful as a dispersant for lubricants and fuels. The product can be further defined as the product of an ester, amide or ester amide derivative of alkenyl-or alkenyl-substituted dibasic acids which reaction product contains hydroxy alkyl groups.
Inventors
- 👤 Raymond C. Schlicht
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-07 18:41
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/22; C10L1/234; C10L1/238; C10L1/2381; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3819; C08G18/3823; C08G18/40; C08G18/60; C08G18/603; C10M; C10M149/00; C10M149/12; C10M149/14; C10M149/18; C10M2217/00; C10M2217/04; C10M2217/044; C10M2217/045
Claims Analysis
Total Claims: 47
Claim 1
Independent Claim
217 words
A polyurethane which is the reaction product of an isocyanate and a diol of the formula ##STR20## wherein each of R, R 1 , R 2 and R 3 is independently a divalent aliphatic or aromatic moiety; u, v, x, y, and z are each independently 0 or 1 and x+y=1 or 2; X is a radical derived from removal of terminal hydrogen atoms from a compound of the formula H--X--H wherein said H--X--H compound is: a. a diamine or polyamine bearing at least two secondary amino groups, optionally containing any number of tertiary amine or other functional groups inert to anhydrides, hydroxyalkylating agents and isocyanates; b. a monohydroxyalkyl secondary amine optionally bearing tertiary amine or other functions inert to anhydrides, hydroxyalkylating agents and isocyanates; or c. a bis-hydroxyalkyl substituted mono di-, or poly-tertiary amine; or X is a -O-R 4 -O moiety where R 4 is a C 2 to C 30 divalent hydrocarbyl group or an oxa-alkylene group of 1 to 15 oxygen atoms, and Y and Z are each O or NR 5 where R 5 is a C 1 to C 30 alkyl group which can be substituted by aryloxy, cyano, C 1 to C 32 carbalkoxy, C 1 to C 32 carboxamido or other substituent inert to anhydrides, hydroxyalkylating agents and isocyanates.
Claim 2
Dependent Claim
217 words
A polyurethane which is the reaction product of an isocyanate and a diol of the formula ##STR20## wherein each of R, R 1 , R 2 and R 3 is independently a divalent aliphatic or aromatic moiety; u, v, x, y, and z are each independently 0 or 1 and x+y=1 or 2; X is a radical derived from removal of terminal hydrogen atoms from a compound of the formula H--X--H wherein said H--X--H compound is: a. a diamine or polyamine bearing at least two secondary amino groups, optionally containing any number of tertiary amine or other functional groups inert to anhydrides, hydroxyalkylating agents and isocyanates; b. a monohydroxyalkyl secondary amine optionally bearing tertiary amine or other functions inert to anhydrides, hydroxyalkylating agents and isocyanates; or c. a bis-hydroxyalkyl substituted mono di-, or poly-tertiary amine; or X is a -O-R 4 -O moiety where R 4 is a C 2 to C 30 divalent hydrocarbyl group or an oxa-alkylene group of 1 to 15 oxygen atoms, and Y and Z are each O or NR 5 where R 5 is a C 1 to C 30 alkyl group which can be substituted by aryloxy, cyano, C 1 to C 32 carbalkoxy, C 1 to C 32 carboxamido or other substituent inert to anhydrides, hydroxyalkylating agents and isocyanates.
Claim 3
Dependent Claim
18 words
A polyurethane according to claim 1 wherein said polyurethane has a molecular weight of between 1,000 and 30,000.
Claim 4
Dependent Claim
27 words
A polyurethane according to claim 2 wherein said polyurethane is soluble at room temperature in a lubricating oil in an amount of at least 0.5 weight percent.
Claim 5
Dependent Claim
28 words
A polyurethane according to claim 3 wherein said polyurethane is soluble at room temperature in a lubricating oil in an amount of between 0.5 and 15 weight percent.
Claim 6
Dependent Claim
18 words
A polyurethane according to claim 2 wherein there are at least two repeating polymeric units in said polyurethane.
Claim 7
Dependent Claim
15 words
A polyurethane according to claim 5 wherein there are 2 to 25 repeating polymeric units.
Claim 8
Dependent Claim
15 words
A polyurethane according to claim 6 wherein there are 5 to 12 repeating polymeric units.
Claim 9
Dependent Claim
44 words
A polyurethane according to claim 1 wherein R and R 3 are each independently a substituted or unsubstituted alkylene group of 2 to 30 carbon atoms and when substituted are substituted by any one of the following groups: cyano, tertiary amino, carbalkoxy or carboxamido.
Claim 10
Dependent Claim
10 words
A polyurethane according to claim 1 wherein x or y=1.
Claim 11
Dependent Claim
85 words
A polyurethane according to claim 1 wherein R 1 and R 2 are each independently an alkylene group of 2 to 30 carbon atoms or an arylene group of 6 to 16 carbocyclic carbon atoms either or both of which groups can be substituted and when substituted can be substituted with any of the following groups: C 12 to C 500 alkyl or alkenyl groups, which may themselves be unsubstituted or substituted with any one of the following groups: cyano, tertiary amino, carbalkoxy or carboxamido.
Claim 12
Dependent Claim
35 words
A polyurethane according to claim 1 wherein said compound H--X--H is an aromatic or heterocyclic secondary amine of 4 to 16 carbocyclic carbon atoms or an aliphatic secondary amine of 3 to 30 carbon atoms.
Claim 13
Dependent Claim
25 words
A polyurethane according to claim 11 wherein X is a divalent hydrocarbyl radical derived from an H--X--H compound bearing at least two secondary amino groups.
Claim 14
Dependent Claim
36 words
A polyurethane according to claim 11 wherein X is a divalent alkylene, alkenylene, alkynylene, cycloalkylene or cycloalkenylene group or a heterocyclic which can have 1 to 3 hetero atoms of the group nitrogen, oxygen and sulfur.
Claim 15
Dependent Claim
46 words
A polyurethane according to claim 11 wherein said compound X--X--H is selected from the group consisting of piperazine, an N,N'-bis-C 1 to C 30 alkyl, C 2 to C 30 alkylenediamines, an N,N'-bis-C 1 to C 30 alkylphenylenediamine and an N,N'-bis-cyanoethyl-C 2 to C 30 alkenylenediamine.
Claim 16
Dependent Claim
25 words
A polyurethane according to claim 1 wherein said compound H--X--H is a monohydroxyalkyl secondary amine of 2 to 30 carbon atoms in the alkyl group.
Claim 17
Dependent Claim
88 words
A polyurethane according to claim 15 wherein said secondary amine is one of the formula ##STR21## wherein R 6 is a C 2 to C 30 alkylene group and R 9 is an alkyl group of 1 to 30 carbon atoms, an alkenyl group of 3 to 30 carbon atoms, an alkynyl group of 3 to 30 carbon atoms or an aryl group of 6 to 16 carbocyclic carbon atoms which amine can be substituted by any one of the following substituents: cyano, tertiary amino, carbalkoxy or carboxamido.
Claim 18
Dependent Claim
32 words
A polyurethane according to claim 16 wherein said secondary amine is selected from the group consisting of N-alkyl-aminoethanols, N-cyanoalkyl-aminoethanols, N-carboalkoxy-alkyl-aminoethanols, N-alkoxyalkyl-aminoethanols, and similar N-substituted-aminopropanols, -aminobutanols, -aminohexanols, N-hydroxyalkylpiperazines, 2-hydroxyalkyl-N-alkylpiperazines, N-hydroxyalkyl-aniline, -toluidine, or -xylidines.
Claim 19
Dependent Claim
85 words
A polyurethane according to claim 1 wherein said compound H-X-H is a bis-hydroxyalkyl substituted mono-, di or poly-tertiary amine having 2 to 30 carbon atoms in the alkyl group, said tertiary amine being the tertiary amine of an aromatic or heterocyclic compound having 4 to 16 carbon atoms where if heterocyclic the hetero atom is oxygen, nitrogen, or sulfur or an alkyl, alkenyl or alkynyl compound containing 1 to 10 tertiary amine groups and 1 to 30 carbon atoms per nitrogen atom in the chain.
Claim 20
Dependent Claim
29 words
A polyurethane according to claim 18 wherein said tertiary amine is a tertiary amine of an aliphatic compound wherein the aliphatic portion of the molecule is a hydrocarbyl group.
Claim 21
Dependent Claim
18 words
A polyurethane according to claim 19 wherein said hydrocarbyl group is a monovalent alkyl, alkenyl or alkynyl group.
Claim 22
Dependent Claim
39 words
A polyurethane according to claim 18 wherein said bis-hydroxyalkyl substituted mono-, di- or poly-tertiary amine is a heterocyclic compound which in addition to any nitrogen atoms in the ring can contain an oxygen or sulfur as additional hetero atoms.
Claim 23
Dependent Claim
38 words
A polyurethane according to claim 18 wherein said bis-hydroxyalkyl substituted mono-, di- or poly-tertiary amine is selected from the group consisting of N-alkyl-imino-bis-alkanols, N-aryl-imino-bis-alkanols, N,N'-bis-hydroxyalkyl-piperazines, N', N""-hydroxyalkyl-N",N"-alkylene-bis-piperazines, N', N.sup.ω -hydroxyalkyl-polyalkylene-poly-piperazines, N,N'-bis-hydroxyalkyl-N,N-bis-cyanoalkyl-alkylenediamines, N',N.sup.ω -N" to N.sup.ω-1 -polycyanoalkyl-poly-alkyleneimines, N,N'-bis-hydroxyalkyl, N,N'-dialkyl-alkylenediamines.
Claim 24
Dependent Claim
55 words
A polyurethane according to claim 1 wherein said compound H-X-H has the formula ##STR22## wherein R 10 and R 11 are independently divalent hydrocarbyl groups of 2 to 30 carbon atoms; and R 12 is an alkyl group of 1 to 30 carbon atoms or an aryl group having 6 to 16 carbocyclic carbon atoms.
Claim 25
Dependent Claim
38 words
A polyurethane according to claim 23 wherein R 10 and R 11 are alkylene groups and R 12 is a C 1 to C 30 alkyl group or an aryl group having 6 to 16 carbocyclic carbon atoms.
Claim 26
Dependent Claim
105 words
A polyurethane according to claim 1 wherein said compound H-X-H is a bis-hydroxyalkyl substituted mono-, di-or poly-tertiary amine of the formula ##STR23## wherein R 10 , R 11 and R 15 are independently divalent hydrocarbyl groups of 2 to 30 carbon atoms; R 12 is an alkyl group of 1 to 30 carbon atoms or an aryl group having 6 to 16 carboxyclic carbon atoms; R 16 is an alkyl or aryl radical which can be substituted by any one of the functions cyano, tertiary amino, or carboxamido; and p=1 to 10 and R 12 may be the same or different in each repeating unit.
Claim 27
Dependent Claim
63 words
A polyurethane according to claim 1 wherein said isocyanate is a diisocyanate of the formula O═C═N--R.sup.17 --N═C═O wherein R 17 is arylene, polyarylene, arylene of at least two arylene nuclei where at least two arylene nuclei are linked together through alkylene, alkylidene, alkenylene groups or oxygen, nitrogen or sulfur atoms, mixed alkylene-arylene, alkylene and polyalkylenes as well as the thioanalogs of such diisocyanates.
Claim 28
Dependent Claim
34 words
A polyurethane according to claim 26 wherein R 17 has 6 to 16 carbocyclic carbon atoms in each arylene nucleus and 0 to 4 chain carbon atoms in each alkylene, alkylidene or alkenylene group.
Claim 29
Dependent Claim
145 words
A polyurethane according to claim 1 wherein said polyurethane has a recurring structural unit of the formula ##STR24## wherein R, R 1 , R 2 , and R 3 have the meanings given in claim 1; x and y are 0 or 1 and x+y=1 or 2; R 17 is an arylene, polyarylene, arylene of at least two arylene nuclei where at least two arylene nuclei are linked together through an alkylene, alkylidene, or alkenylene group, oxygen, nitrogen or sulfur atom, mixed alkylene-arylene, alkylene and polyalkylene radicals as well as the thioanalogs of such diisocyanates; R 18 and R 19 are each independently alkyl or alkenyl of 12 to 500 carbon atoms; R 20 and R 21 are each divalent aryl radicals of 6 to 16 carbocyclic carbon atoms or alkyl or alkenyl groups of 2 to 30 chain carbon atoms; and n=2 to 30.
Claim 30
Dependent Claim
26 words
A polyurethane according to claim 28 wherein each of R 18 and R 19 is an alkyl or alkenyl group of 12 to 30 carbon atoms.
Claim 31
Dependent Claim
91 words
A polyurethane according to claim 1 wherein said polyol has the formula ##STR25## wherein R, R 1 , R 2 and R 3 have the meanings given in claim 1; R 18 and R 19 are C 12 -C 500 alkyl or alkenyl groups; R 22 and R 24 are independently alkyl, alkoxyalkyl, aryloxyalkyl, cyanoalkyl, carboalkoxyalkyl, carboxamidoalkyl, or one of such groups substituted by a group inert to an anhydride, hydroxyalkylating agent or isocyanate; and R 23 is a divalent alkylene, alkenylene or arylene group of 2 to 30 carbon atoms.
Claim 32
Dependent Claim
68 words
A polyurethane according to claim 1 wherein said polyol has the formula ##STR26## wherein R, R 1 and R 3 have the meanings given in claim 1; R 18 is a C 12 to C 500 alkyl or alkenyl group; and R 22 is an alkyl, tertiary aminoalkyl, cyanoalkyl, carboalkoxyalkyl, carboxamidoalkyl, or one of such groups substituted by a group inert to an anhydride, hydroxyalkylating agent or isocyanate.
Claim 33
Dependent Claim
105 words
A polyurethane according to claim 1 wherein said polyol has the formula ##STR27## wherein R, R 1 , R 2 , and R 3 have the meanings given in claim 1; R 18 and R 19 each independently represent a C 12 to C 500 alkyl or alkenyl group; R 22 is an alkyl, tertiary aminoalkyl, cyanoalkyl, carboalkoxyalkyl, carboxamidoalkyl, or one of such groups substituted by a group inert to an anhydride, hydroxyalkylating agent or isocyanate; and R 25 is an alkylene or arylene moiety of 2 to 20 carbon atoms which can be substituted by a moiety inert to anhydrides, hydroxyalkylating agents and isocyanates.
Claim 34
Dependent Claim
71 words
A polyurethane according to claim 1 wherein said polyol has the formula ##STR28## wherein R, R 1 , R 3 , and Z have the meanings given in claim 1; R 18 is a C 12 to C 500 alkyl or alkenyl group; and R 22 is an alkyl, tertiary aminoalkyl, cyanoalkyl, carboalkoxyalkyl, carboxamidoalkyl, or one of such groups substituted by a group inert to an anhydride, hydroxyalkylating agent or isocyanate.
Claim 35
Dependent Claim
68 words
A polyurethane according to claim 1 wherein said polyol has the formula ##STR29## wherein R, R 1 , R 2 , R 3 , Y and Z have the meanings given in claim 1; R 18 and R 19 are each independently C 12 and C 500 alkyl or alkenyl groups; and R 23 is a divalent alkylene, alkenylene or arylene group of 2 to 30 carbon atoms.
Claim 36
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 1.
Claim 37
Dependent Claim
22 words
A lubricating oil composition according to claim 35 wherein said polyurethane is present in an amount of 0.5 to 15 weight percent.
Claim 38
Dependent Claim
22 words
A lubricating oil composition according to claim 35 wherein said polyurethane is present in an amount of 40 to 60 weight percent.
Claim 39
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 30.
Claim 40
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 31.
Claim 41
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 32.
Claim 42
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 33.
Claim 43
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 34.
Claim 44
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 2.
Claim 45
Dependent Claim
14 words
A lubricating oil composition comprising a lubricating oil and the polyurethane of claim 28.
Claim 46
Dependent Claim
12 words
A fuel composition comprising a fuel and the polyurethane of claim 1.
Claim 47
Dependent Claim
21 words
A fuel composition according to claim 45 wherein said polyurethane is present in an amount between 0.0002 and 0.05 weight percent.
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) | 1983-11-25 | 1984-05-26 | 1984-11-25 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1987-11-25 | 1988-05-26 | 1988-11-25 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1991-11-25 | 1992-05-26 | 1992-11-25 | $7700.00 | Window Closed / Lapsed |