US4359325A
Expired / Lapsed
US
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Copolymers from acrylate dicarboxylic compounds and diisobutylene as oil additives
Assignee: IFP Energies nouvelles
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Filing: 1980-12-15
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Granted: 1982-11-16
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Expires: 2000-12-15
Abstract
Abstract Copolymers comprising acrylic ester units, dicarboxylic compounds units and diisobutylene units and whose average molecular weight by number is from 500 to 250,000 are useful for improving the cold-flow properties of lube oils and other hydrocarbon oils such as diesel oil, heavy fuel oil, residual fuel oil and crude petroleum.
Inventors
- 👤 Francois Dawans
- 👤 Jean-Pierre Durand
- 👤 Daniel Binet
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-30 19:14
CPC Classifications
C; C10; C10L; C10L1/00; C10L1/10; C10L1/14; C10L1/18; C10L1/192; C10L1/195; C10L1/196; C10L1/1966; C08; C08F; C08F220/00; C08F220/02; C08F220/10; C08F220/12; C08F222/00; C10L1/22; C10L1/234; C10L1/236; C10L1/2364; C10M; C10M2203/00; C10M2203/10; C10M2209/00; C10M2209/02; C10M2209/08; C10M2209/086; C10M2217/00; C10M2217/02; C10M2217/024; C10M2217/06; F; F02; F02B; F02B3/00; F02B3/06; Y; Y10; Y10S; Y10S526/00; Y10S526/933
Claims Analysis
Total Claims: 31
Claim 1
Independent Claim
141 words
A copolymer consisting essentially of: (A) 10-94% by mole of acrylic ester units having the formula ##STR6## wherein R 1 is H or CH 3 ; and R 2 is C 1-30 alkyl; (B) 3-65% by mole of dicarboxylic units having the formula ##STR7## wherein R 3 and R 4 are each independently H or CH 3 ; X and Y are each independently OR 2 , OR 5 or NHR 5 ; wherein R 2 is C 1-30 alkyl; and R 5 is H or a monovalent organic radical; and (C) 3-40% by mole of diisobutylene units having the formula ##STR8## wherein the molar proportion of the units having the formula (B) is at least as high as the molar proportion of the units having the formula (C); and wherein said copolymer has a number average molecular weight of 500-250,000.
Claim 2
Dependent Claim
141 words
A copolymer consisting essentially of: (A) 10-94% by mole of acrylic ester units having the formula ##STR6## wherein R 1 is H or CH 3 ; and R 2 is C 1-30 alkyl; (B) 3-65% by mole of dicarboxylic units having the formula ##STR7## wherein R 3 and R 4 are each independently H or CH 3 ; X and Y are each independently OR 2 , OR 5 or NHR 5 ; wherein R 2 is C 1-30 alkyl; and R 5 is H or a monovalent organic radical; and (C) 3-40% by mole of diisobutylene units having the formula ##STR8## wherein the molar proportion of the units having the formula (B) is at least as high as the molar proportion of the units having the formula (C); and wherein said copolymer has a number average molecular weight of 500-250,000.
Claim 3
Dependent Claim
31 words
A copolymer according to claim 1, wherein in at least a portion of the units having the formula (A), R 1 is CH 3 and R 2 is C 4-18 alkyl.
Claim 4
Dependent Claim
30 words
A copolymer according to claim 1, wherein in at least a portion of the units having the formula (A), R 1 is H and R 2 is C 4-22 alkyl.
Claim 5
Dependent Claim
27 words
A copolymer according to claim 1, wherein in at least a portion of the units having the formula (B), R 3 and R 4 are each H.
Claim 6
Dependent Claim
34 words
A copolymer according to claim 1, wherein at least a portion of the dicarboxylic units (B) have the formula ##STR9## wherein R 3 and R 4 are each independently H or CH 3 .
Claim 7
Dependent Claim
84 words
A copolymer according to claim 1, wherein at least a portion of the dicarboxylic units (B) have the formula ##STR10## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is OR 2 or OR 5 , R 2 being butyl or C 18 alkyl, and R 5 being the monovalent organic radical corresponding to the alcohol R 5 OH, wherein R 5 OH is pentaerythritol, glycerol, trimethylolpropane, diethylethanolamine or diethanolamine.
Claim 8
Dependent Claim
78 words
A copolymer according to claim 1, wherein at least a portion of the dicarboxylic units (B) have the formula ##STR11## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is NHR 5 , R 5 in all occurrences being the monovalent organic radical corresponding to the amine R 5 NH 2 , wherein R 5 NH 2 is dimethylaminopropylamine, triethylenetetramine, tetraethylenepentamine, 2-aminopyridine or 1-cyanoguanidine.
Claim 9
Dependent Claim
34 words
A hydrocarbon oil composition comprising a major proportion of hydrocarbon oil and a minor proportion of at least one copolymer according to claim 1 sufficient to improve the cold-flow properties of said hydrocarbon oil.
Claim 10
Dependent Claim
52 words
A composition according to claim 8, wherein said hydrocarbon oil is a lubricating oil and said copolymer has 20 to 90% by mole of units having the formula (A), 5 to 65% by mole of units having the formula (B) and 5 to 40% by mole of units having the formula (C).
Claim 11
Dependent Claim
44 words
A composition according to claim 9, wherein in said copolymer, the units having the formula (A) amount to 40-75% by mole, the units having the formula (B) amount to 10-40% by mole and the units having the formula (C) amount to 10-30% by mole.
Claim 12
Dependent Claim
20 words
A composition according to claim 9, wherein the number average molecular weight of said copolymer is from 3,000 to 70,000.
Claim 13
Dependent Claim
19 words
A composition according to claim 9, wherein the proportion of said copolymer is from 0.01 to 4% by weight.
Claim 14
Dependent Claim
19 words
A composition according to claim 12, wherein the proportion of said copolymer is from 0.5 to 2% by weight.
Claim 15
Dependent Claim
34 words
A composition according to claim 9, wherein in said copolymer, in at least a portion of the units having the formula (A), R 1 is CH 3 and R 2 is C 4-18 alkyl.
Claim 16
Dependent Claim
30 words
A composition according to claim 9, wherein in said copolymer, in at least a portion of the units having the formula (B), R 3 and R 4 are each H.
Claim 17
Dependent Claim
37 words
A composition according to claim 9, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR12## wherein R 3 and R 4 are each independently H or CH 3 .
Claim 18
Dependent Claim
87 words
A composition according to claim 9, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR13## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is OR 2 or OR 5 , R 2 being butyl or C 18 alkyl, and R 5 being the monovalent organic radical corresponding to the alcohol R 5 OH, wherein R 5 OH is pentaerythritol, glycerol, trimethylolpropane, diethylethanolamine or diethanolamine.
Claim 19
Dependent Claim
81 words
A composition according to claim 9, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR14## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is NHR 5 , R 5 in all occurrences being the monovalent organic radical corresponding to the amine R 5 NH 2 , wherein R 5 NH 2 is dimethylaminopropylamine, triethylenetetramine, tetraethylenepentamine, 2-aminopyridine or 1-cyanoguanidine.
Claim 20
Dependent Claim
83 words
A composition according to claim 8, wherein the hydrocarbon oil is diesel oil, domestic fuel oil, heavy fuel oil, fuel oil No. 2, residual fuel oil or crude petroleum, and wherein said copolymer has from 10 to 94% by mole of units having the formula (A), from 3 to 50% by mole of units having the formula (B) and from 3 to 40% by mole of units having the formula (C), and has a number average molecular weight of from 500 to 200,000.
Claim 21
Dependent Claim
47 words
A composition according to claim 19, wherein said terpolymer has from 40 to 80% by mole of units having the formula (A), from 10 to 35% by mole of units having the formula (B) and from 10 to 25% by mole of units having the formula (C).
Claim 22
Dependent Claim
21 words
A composition according to claim 19, wherein the number average molecular weight of said terpolymer is from about 1,000 to 70,000.
Claim 23
Dependent Claim
19 words
A composition according to claim 19, wherein the proportion of said copolymer is from 0.005 to 2% by weight.
Claim 24
Dependent Claim
19 words
A composition according to claim 22, wherein the proportion of said copolymer is from 0.01 to 0.5% by weight.
Claim 25
Dependent Claim
33 words
A composition according to claim 19, wherein in said copolymer, in at least a portion of the units having the formula (A), R 1 is H and R 2 is C 4-22 alkyl.
Claim 26
Dependent Claim
17 words
A composition according to claim 24, wherein R 2 is butyl, 2-ethylhexyl, lauryl, stearyl, eicosyl or docosyl.
Claim 27
Dependent Claim
30 words
A composition according to claim 19, wherein in said copolymer, in at least a portion of the units having the formula (B), R 3 and R 4 are each H.
Claim 28
Dependent Claim
37 words
A composition according to claim 19, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR15## wherein R 3 and R 4 are each independently H or CH 3 .
Claim 29
Dependent Claim
87 words
A composition according to claim 19, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR16## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is OR 2 or OR 5 , R 2 being butyl or C 18 alkyl, and R 5 being the monovalent organic radical corresponding to the alcohol R 5 OH, wherein R 5 OH is pentaerythritol, glycerol, trimethylolpropane, diethylethanolamine or diethanolamine.
Claim 30
Dependent Claim
81 words
A composition according to claim 19, wherein in said copolymer, at least a portion of the dicarboxylic units (B) have the formula ##STR17## wherein R 3 and R 4 are each independently H or CH 3 ; and wherein at least one of X and Y is NHR 5 , R 5 in all occurrences being the monovalent organic radical corresponding to the amine R 5 NH 2 , wherein R 5 NH 2 is dimethylaminopropylamine, triethylenetetramine, tetraethylenepentamine, 2-aminopyridine or 1-cyanoguanidine.
Claim 31
Dependent Claim
31 words
A method of improving the cold-flow properties of a hydrocarbon oil, comprising adding to said oil an amount sufficient to improve its cold-flow properties of a copolymer according to claim 1.
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) | 1985-11-15 | 1986-05-17 | 1986-11-16 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1989-11-15 | 1990-05-17 | 1990-11-16 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1993-11-15 | 1994-05-17 | 1994-11-16 | $7700.00 | Window Closed / Lapsed |