GB922878A - Oil-soluble copolymeric materials and compositions containing the same - Google Patents
Oil-soluble copolymeric materials and compositions containing the sameInfo
- Publication number
- GB922878A GB922878A GB21977/59A GB2197759A GB922878A GB 922878 A GB922878 A GB 922878A GB 21977/59 A GB21977/59 A GB 21977/59A GB 2197759 A GB2197759 A GB 2197759A GB 922878 A GB922878 A GB 922878A
- Authority
- GB
- United Kingdom
- Prior art keywords
- oils
- group
- maleic
- fumaric
- mono
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired
Links
- 229920001577 copolymer Polymers 0.000 title abstract 5
- 239000000463 material Substances 0.000 title 1
- 239000000203 mixture Substances 0.000 title 1
- 239000003921 oil Substances 0.000 abstract 5
- 235000019198 oils Nutrition 0.000 abstract 5
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 abstract 4
- 239000002253 acid Substances 0.000 abstract 4
- 125000001931 aliphatic group Chemical group 0.000 abstract 4
- 125000004432 carbon atom Chemical group C* 0.000 abstract 4
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 abstract 4
- -1 polysiloxanes Polymers 0.000 abstract 4
- 239000004215 Carbon black (E152) Substances 0.000 abstract 3
- 125000002947 alkylene group Chemical group 0.000 abstract 3
- UZKWTJUDCOPSNM-UHFFFAOYSA-N 1-ethenoxybutane Chemical compound CCCCOC=C UZKWTJUDCOPSNM-UHFFFAOYSA-N 0.000 abstract 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 abstract 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 abstract 2
- JIGUQPWFLRLWPJ-UHFFFAOYSA-N Ethyl acrylate Chemical class CCOC(=O)C=C JIGUQPWFLRLWPJ-UHFFFAOYSA-N 0.000 abstract 2
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 abstract 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 abstract 2
- VVQNEPGJFQJSBK-UHFFFAOYSA-N Methyl methacrylate Chemical compound COC(=O)C(C)=C VVQNEPGJFQJSBK-UHFFFAOYSA-N 0.000 abstract 2
- SYNHCENRCUAUNM-UHFFFAOYSA-N Nitrogen mustard N-oxide hydrochloride Chemical compound Cl.ClCC[N+]([O-])(C)CCCl SYNHCENRCUAUNM-UHFFFAOYSA-N 0.000 abstract 2
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 abstract 2
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 abstract 2
- 150000007513 acids Chemical class 0.000 abstract 2
- 125000000217 alkyl group Chemical group 0.000 abstract 2
- 125000003710 aryl alkyl group Chemical group 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 abstract 2
- 150000001991 dicarboxylic acids Chemical class 0.000 abstract 2
- 229910052736 halogen Inorganic materials 0.000 abstract 2
- 150000002367 halogens Chemical class 0.000 abstract 2
- 229930195733 hydrocarbon Natural products 0.000 abstract 2
- 150000002430 hydrocarbons Chemical class 0.000 abstract 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract 2
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 abstract 2
- 229920000768 polyamine Polymers 0.000 abstract 2
- 229920000642 polymer Polymers 0.000 abstract 2
- 229920001296 polysiloxane Polymers 0.000 abstract 2
- AHDSRXYHVZECER-UHFFFAOYSA-N 2,4,6-tris[(dimethylamino)methyl]phenol Chemical compound CN(C)CC1=CC(CN(C)C)=C(O)C(CN(C)C)=C1 AHDSRXYHVZECER-UHFFFAOYSA-N 0.000 abstract 1
- YEVQZPWSVWZAOB-UHFFFAOYSA-N 2-(bromomethyl)-1-iodo-4-(trifluoromethyl)benzene Chemical compound FC(F)(F)C1=CC=C(I)C(CBr)=C1 YEVQZPWSVWZAOB-UHFFFAOYSA-N 0.000 abstract 1
- MQIUGAXCHLFZKX-UHFFFAOYSA-N Di-n-octyl phthalate Natural products CCCCCCCCOC(=O)C1=CC=CC=C1C(=O)OCCCCCCCC MQIUGAXCHLFZKX-UHFFFAOYSA-N 0.000 abstract 1
- 229910019142 PO4 Inorganic materials 0.000 abstract 1
- 235000004443 Ricinus communis Nutrition 0.000 abstract 1
- 229920006222 acrylic ester polymer Polymers 0.000 abstract 1
- 239000000654 additive Substances 0.000 abstract 1
- 150000001336 alkenes Chemical class 0.000 abstract 1
- 150000003973 alkyl amines Chemical class 0.000 abstract 1
- 239000002518 antifoaming agent Substances 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 229910052788 barium Inorganic materials 0.000 abstract 1
- BJQHLKABXJIVAM-UHFFFAOYSA-N bis(2-ethylhexyl) phthalate Chemical compound CCCCC(CC)COC(=O)C1=CC=CC=C1C(=O)OCC(CC)CCCC BJQHLKABXJIVAM-UHFFFAOYSA-N 0.000 abstract 1
- 239000004359 castor oil Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 239000003795 chemical substances by application Substances 0.000 abstract 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 abstract 1
- VJHINFRRDQUWOJ-UHFFFAOYSA-N dioctyl sebacate Chemical compound CCCCC(CC)COC(=O)CCCCCCCCC(=O)OCC(CC)CCCC VJHINFRRDQUWOJ-UHFFFAOYSA-N 0.000 abstract 1
- 239000010699 lard oil Substances 0.000 abstract 1
- 239000000314 lubricant Substances 0.000 abstract 1
- 150000002895 organic esters Chemical class 0.000 abstract 1
- 235000021317 phosphate Nutrition 0.000 abstract 1
- 229920001515 polyalkylene glycol Polymers 0.000 abstract 1
- AOHJOMMDDJHIJH-UHFFFAOYSA-N propylenediamine Chemical compound CC(N)CN AOHJOMMDDJHIJH-UHFFFAOYSA-N 0.000 abstract 1
- 150000003839 salts Chemical class 0.000 abstract 1
- 229920005573 silicon-containing polymer Polymers 0.000 abstract 1
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 abstract 1
- IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 abstract 1
- 235000015112 vegetable and seed oil Nutrition 0.000 abstract 1
- 239000008158 vegetable oil Substances 0.000 abstract 1
Classifications
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- C10M149/00—Lubricating compositions characterised by the additive being a macromolecular compound containing nitrogen
- C10M149/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M149/06—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to an amido or imido group
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- C08F8/00—Chemical modification by after-treatment
- C08F8/30—Introducing nitrogen atoms or nitrogen-containing groups
- C08F8/32—Introducing nitrogen atoms or nitrogen-containing groups by reaction with amines
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- C10L1/00—Liquid carbonaceous fuels
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- C10L1/221—Organic compounds containing nitrogen compounds of uncertain formula; reaction products where mixtures of compounds are obtained
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- C08F210/02—Ethene
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- C08F222/00—Copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by a carboxyl radical and containing at least one other carboxyl radical in the molecule; Salts, anhydrides, esters, amides, imides, or nitriles thereof
- C08F222/36—Amides or imides
- C08F222/40—Imides, e.g. cyclic imides
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- C10M2209/00—Organic macromolecular compounds containing oxygen as ingredients in lubricant compositions
- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
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- C10M2209/02—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- C10M2209/08—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type
- C10M2209/086—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds containing monomers having an unsaturated radical bound to a carboxyl radical, e.g. acrylate type polycarboxylic, e.g. maleic acid
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- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
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- C10M2219/087—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Derivatives thereof, e.g. sulfurised phenols
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- C10M2219/082—Thiols; Sulfides; Polysulfides; Mercaptals containing sulfur atoms bound to acyclic or cycloaliphatic carbon atoms
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Abstract
Oil-soluble copolymer derivatives are derived from copolymers having a molecular weight between 500 and 150,000 and obtained from equimolar proportions of a C4 or C5 olefinic dicarboxylic acid or such an acid wherein one or two of the hydrogen atoms attached to the carbon chain have been replaced by halogen, alkyl, aryl or aralkyl, and a comonomer having a terminal methylene group and containing 2 to 8 carbon atoms by (a) reacting not more than 95% of the carboxy groups with a straight or branched chain monohydric alcohol or a straight chain primary or secondary monoamine or oxyamine having 10 to 24 carbon atoms and (b) reacting substantially all the remaining carboxyl groups with a polyamine or aminoalcohol having one of the formulae <FORM:0922878/III/1> where each of R1, R2, R5 and R6 is a C1-4 aliphatic hydrocarbon group or a cyclohexyl group; each of R3 and R4 is a C2-4 alkylene group; and Y is OH or -NHR7 where R7 is H or a C1-4 aliphatic hydrocarbon group. Dicarboxylic acids specified are maleic, fumaric, mono- and di-chloro maleic and fumaric, citraconic, mesaconic, ethyl- and mono- and diphenyl- and benzyl-maleic, itaconic and glutaconic acids. Comonomers specified are C2-8 olefines, styrene, vinyl acetate, methyl and ethyl acrylates, methyl methacrylate and vinyl butyl ether. Oils to which the polymer derivatives may be added are hydrocarbon oils heavier than gasoline, and may be blended with vegetable oils such as castor and lard oils and/or with synthetic lubricants, e.g. polymerized olefins, polyalkylene glycols and alkylene oxides, organic esters such as 2-ethylhexyl sebacate, dioctyl phthalate and trioctyl phosphate, polymeric tetra-hydrofuran and polysiloxanes such as dimethyl silicone polymer. Other oil additives which may be used in conjunction with those of the invention are alkylamines, e.g. tri-n-butylamine and 2,4,6-tri-(dimethylaminomethyl) phenol; N,N-disalicylidene p 1,2-diaminopropane; acrylic ester polymers; silicone anti-foam agents; antioxidants, e.g. alkyl phenols, allophanates, alkyl phosphates and salts thereof; barium sulphonates and barium-P2S5-hydrocarbon reaction products. Specifications 686,381 and 870,398 are referred to.ALSO:Oil-soluble copolymer derivatives are derived from copolymers having a molecular weight between 500 and 150,000 and obtained from equimolar proportions of a C4 or C5 olefinic dicarboxylic acid, or such an acid wherein one or two of the hydrogen atoms attached to the carbon chain have been replaced by halogen, alkyl, aryl or aralkyl, and a comonomer having a terminal methylene group and containing 2 to 8 carbon atoms by (a) reacting not more than 95% of the carboxy groups with a straight or branched chain monohydric alcohol or a straight chain primary or secondary monoamine or oxyamine having 10 to 24 carbon atoms and (b) reacting substantially all the remaining carboxyl groups with a polyamine or aminoalcohol having one of the formulae <FORM:0922878/IV(a)/1> or <FORM:0922878/IV(a)/2> where each of R1, R2, R5 and R6 a C1-4 aliphatic hydrocarbon group or a cyclohexyl group; each of R3 and R4 is a C2-4 alkylene group; and Y is OH or -NHR7 where R7 is H or a C1-4 aliphatic hydrocarbon group. Dicarboxylic acids specified are maleic, fumaric, mono- and di-chloro maleic and fumaric, citraconic, mesaconic, ethyl- and mono- and diphenyl- and benzylmaleic, itaconic and glutaconic acids. Comonomers specified are C2-8 olefines, styrene, vinyl acetate, methyl and ethyl acrylates, methyl methacrylate and vinyl butyl ether. Preferred oils to which the polymer derivatives may be added are hydrocarbon oils. Various other possible uses are catalogued. Specifications 686,381 and 870,398 are referred to.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US74468358A | 1958-06-26 | 1958-06-26 |
Publications (1)
Publication Number | Publication Date |
---|---|
GB922878A true GB922878A (en) | 1963-04-03 |
Family
ID=24993608
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
GB21977/59A Expired GB922878A (en) | 1958-06-26 | 1959-06-26 | Oil-soluble copolymeric materials and compositions containing the same |
Country Status (2)
Country | Link |
---|---|
DE (1) | DE1145289B (en) |
GB (1) | GB922878A (en) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0000650A2 (en) * | 1977-07-25 | 1979-02-07 | Monsanto Company | Non-activating polyelectrolytes and their use in a method for separation of blood coagulation factors |
GB2124633A (en) * | 1982-07-06 | 1984-02-22 | Lubrizol Corp | Nitrogen-containing esters and lubricants containing them |
US4594378A (en) * | 1985-03-25 | 1986-06-10 | The Lubrizol Corporation | Polymeric compositions, oil compositions containing said polymeric compositions, transmission fluids and hydraulic fluids |
US4604221A (en) * | 1982-07-06 | 1986-08-05 | The Lubrizol Corporation | Nitrogen-containing esters and lubricants containing them |
FR2743811A1 (en) * | 1996-01-18 | 1997-07-25 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ALKENYL SUCCINIMIDES OR POLYALKENYL SUCCINIMIDES |
US5703023A (en) * | 1991-12-24 | 1997-12-30 | Ethyl Corporation | Lubricants with enhanced low temperature properties |
WO2007133995A3 (en) * | 2006-05-08 | 2008-03-20 | Lubrizol Corp | Lubricating composition containing a polymer and antiwear agents |
WO2013123102A3 (en) * | 2012-02-17 | 2013-11-21 | The Lubrizol Corporation | Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications |
Family Cites Families (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
BE529084A (en) * | 1953-05-25 | |||
NL105836C (en) * | 1953-06-10 | |||
NL102109C (en) * | 1955-09-26 |
-
1959
- 1959-06-26 GB GB21977/59A patent/GB922878A/en not_active Expired
- 1959-06-26 DE DEM41965A patent/DE1145289B/en active Pending
Cited By (12)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
EP0000650A2 (en) * | 1977-07-25 | 1979-02-07 | Monsanto Company | Non-activating polyelectrolytes and their use in a method for separation of blood coagulation factors |
EP0000650A3 (en) * | 1977-07-25 | 1979-04-04 | Monsanto Company | Non-activating polyelectrolytes for separation of blood coagulation factors |
GB2124633A (en) * | 1982-07-06 | 1984-02-22 | Lubrizol Corp | Nitrogen-containing esters and lubricants containing them |
US4604221A (en) * | 1982-07-06 | 1986-08-05 | The Lubrizol Corporation | Nitrogen-containing esters and lubricants containing them |
US4594378A (en) * | 1985-03-25 | 1986-06-10 | The Lubrizol Corporation | Polymeric compositions, oil compositions containing said polymeric compositions, transmission fluids and hydraulic fluids |
US4654403A (en) * | 1985-03-25 | 1987-03-31 | The Lubrizol Corporation | Polymeric compositions comprising olefin polymer and nitrogen containing ester of a carboxy interpolymer |
US5703023A (en) * | 1991-12-24 | 1997-12-30 | Ethyl Corporation | Lubricants with enhanced low temperature properties |
FR2743811A1 (en) * | 1996-01-18 | 1997-07-25 | Inst Francais Du Petrole | PROCESS FOR PRODUCING ALKENYL SUCCINIMIDES OR POLYALKENYL SUCCINIMIDES |
US5735915A (en) * | 1996-01-18 | 1998-04-07 | Institut Francais Du Petrole | Simplified process for production of alkenylsuccinimides or polyalkenylsuccinimides |
WO2007133995A3 (en) * | 2006-05-08 | 2008-03-20 | Lubrizol Corp | Lubricating composition containing a polymer and antiwear agents |
US8293689B2 (en) | 2006-05-08 | 2012-10-23 | The Lubrizol Corporation | Lubricating composition containing a polymer and antiwear agents |
WO2013123102A3 (en) * | 2012-02-17 | 2013-11-21 | The Lubrizol Corporation | Lubricating composition including esterified copolymer and low dispersant levels suitable for driveline applications |
Also Published As
Publication number | Publication date |
---|---|
DE1145289B (en) | 1963-03-14 |
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