US2731481A - Dimeric fatty acids - Google Patents
Dimeric fatty acids Download PDFInfo
- Publication number
- US2731481A US2731481A US239846A US23984651A US2731481A US 2731481 A US2731481 A US 2731481A US 239846 A US239846 A US 239846A US 23984651 A US23984651 A US 23984651A US 2731481 A US2731481 A US 2731481A
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- Prior art keywords
- fatty acids
- dimeric
- acid
- esters
- acids
- 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 - Lifetime
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- 235000014113 dietary fatty acids Nutrition 0.000 title claims description 20
- 229930195729 fatty acid Natural products 0.000 title claims description 20
- 239000000194 fatty acid Substances 0.000 title claims description 20
- 150000004665 fatty acids Chemical class 0.000 title claims description 20
- 238000000034 method Methods 0.000 claims description 13
- 150000002148 esters Chemical class 0.000 claims description 10
- 150000001875 compounds Chemical class 0.000 claims description 7
- 238000010438 heat treatment Methods 0.000 claims description 7
- 230000000447 dimerizing effect Effects 0.000 claims description 5
- 150000001451 organic peroxides Chemical class 0.000 claims description 3
- 239000002253 acid Substances 0.000 description 16
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 10
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 10
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 10
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 10
- 239000005642 Oleic acid Substances 0.000 description 10
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 10
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 9
- 150000007513 acids Chemical class 0.000 description 7
- LSXWFXONGKSEMY-UHFFFAOYSA-N di-tert-butyl peroxide Chemical compound CC(C)(C)OOC(C)(C)C LSXWFXONGKSEMY-UHFFFAOYSA-N 0.000 description 7
- 150000002978 peroxides Chemical class 0.000 description 7
- 229920000642 polymer Polymers 0.000 description 7
- 125000000217 alkyl group Chemical group 0.000 description 6
- 239000000539 dimer Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 6
- 239000012969 di-tertiary-butyl peroxide Substances 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 3
- 238000000354 decomposition reaction Methods 0.000 description 3
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 229910052740 iodine Inorganic materials 0.000 description 2
- 239000011630 iodine Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 239000000178 monomer Substances 0.000 description 2
- 150000005846 sugar alcohols Polymers 0.000 description 2
- 238000012719 thermal polymerization Methods 0.000 description 2
- HQOVXPHOJANJBR-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)butane Chemical compound CC(C)(C)OOC(C)(CC)OOC(C)(C)C HQOVXPHOJANJBR-UHFFFAOYSA-N 0.000 description 1
- HVECLSHLWXTXCE-UHFFFAOYSA-N 2,2-bis(tert-butylperoxy)pentane Chemical compound CC(C)(C)OOC(C)(CCC)OOC(C)(C)C HVECLSHLWXTXCE-UHFFFAOYSA-N 0.000 description 1
- QSFTWOJPCWPORR-UHFFFAOYSA-N 2-(2-tert-butylperoxypropan-2-ylperoxy)-2-methylpropane Chemical compound CC(C)(C)OOC(C)(C)OOC(C)(C)C QSFTWOJPCWPORR-UHFFFAOYSA-N 0.000 description 1
- JZQAIPKOAZJLET-UHFFFAOYSA-N 3,3-bis(tert-butylperoxy)pentane Chemical compound CC(C)(C)OOC(CC)(CC)OOC(C)(C)C JZQAIPKOAZJLET-UHFFFAOYSA-N 0.000 description 1
- KYXHKHDZJSDWEF-LHLOQNFPSA-N CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 Chemical compound CCCCCCC1=C(CCCCCC)C(\C=C\CCCCCCCC(O)=O)C(CCCCCCCC(O)=O)CC1 KYXHKHDZJSDWEF-LHLOQNFPSA-N 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 238000013019 agitation Methods 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000011248 coating agent Substances 0.000 description 1
- 238000000576 coating method Methods 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000006471 dimerization reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 235000021588 free fatty acids Nutrition 0.000 description 1
- 125000005456 glyceride group Chemical group 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 150000002889 oleic acids Chemical class 0.000 description 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical class OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 239000011347 resin Substances 0.000 description 1
- 229920005989 resin Polymers 0.000 description 1
- 230000000717 retained effect Effects 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 239000013638 trimer Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F20/00—Homopolymers and copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and only one being terminated by only one carboxyl radical or a salt, anhydride, ester, amide, imide or nitrile thereof
- C08F20/62—Monocarboxylic acids having ten or more carbon atoms; Derivatives thereof
Definitions
- the present invention relates to a novel process of producing dimeric fatty acids and esters thereof, and to the resultant products. Polyesters, polyamides, and other derivatives of these dimeric fatty acids possess unusual properties which distinguish them from correspond ing products derived from other dimeric fatty acids.
- the dimeric fatty acids of the present invention are useful in the coating, resin, and fiber fields.
- the present invention involves the dimerization of monoolefinic higher fatty acids to produce dimeric, and, to some extent, higher polmeric acids, which retain the unsaturation of the fatty acids from which they are derived. It is thus possible to produce dimeric acids from such unsaturated acids as oleic acid, which do not readily undergo polymerization in the usual thermal polymerization process.
- any polymers formed in the usual thermal polymerization of oleic acid are essentially saturated or contain one double bond per dimer molecule, whereas the polymeric acids of the present invention retain the unsaturation of the fatty acids employed.
- the process involves the treatment, at temperatures in excess of 50 C., of higher fatty acids or esters thereof having only one double bond in the fatty group, with organic peroxides having the formula ROOR in which R is a tertiary alkyl group and R is selected from the group consisting of tertiary alkyl and tertiary alkyl peroxyalkyl groups.
- organic peroxides having the formula ROOR in which R is a tertiary alkyl group and R is selected from the group consisting of tertiary alkyl and tertiary alkyl peroxyalkyl groups.
- Typical of these peroxides are di-tertiary butyl peroxide; 2,2-bis-t-butylperoxy propane; 2,2-bis-t-butylperoxy butane; 2,2-bis-t-butylperoxy pentane; and 3,3-bist-butylperoxy pentane.
- the process is applicable to the free fatty acids containing from 8 to 22 carbon atoms, to the lower aliphatic esters thereof, as for example, the methyl esters, and to the polyhydric alcohol esters thereof, as for example, the glycerides and the pentaerythritol esters. Any higher fatty acid containing a single point of unsaturation may be employed in the present process.
- Commercially oleic acid is the principal acid readily available for this purpose, and accordingly the invention will be described with particular reference thereto.
- the process involves merely mixing thefatty acid or its ester with the peroxide, and heating the mixture in an inert atmosphere for the required time at the required States atent O "ice temperature.
- temperatures in excess of C. are usually employed.
- the temper: atures are in the neighborhood of -l50 C., requiring time periods of 12 to 48 hours.
- the reaction product may, if desired, be stripped under vacuum to remove all the decomposition products of the peroxide as well as any monomeric fatty acids or esters present therein.
- the resultant prodnot is essentially a dimeric acid or dimeric ester and contains smaller quantities of higher polymers. It will be appreciated that the removal of the decomposition prodnets and the monomeric fatty acids or esters is not essential if the product desired is a mixture of monomer and dimer and higher polymers.
- Example The oleic acid employed in this example had an acid number of 198.4, and an iodine number of 88.7. 20 grams (0.971 mol) of this oleic acid and 0.75 g. (0.0051 moi) di-tertiary-butyl peroxide were heated without agitation in sealed bottles under nitrogen. The temperature was maintained at 130 C. for 24 hours. Then an additional 0.75 g. of di-tert-butyl peroxide was added, and the heating was continued for another 24 hours. The reaction mixture was then stripped under vacuum to remove volatile decomposition products. The rcsidue was distilled under high vacuum to remove monomeric acid and to yield a dimeric fraction and a polymeric residue.
- the dimeric material is largely a dimer acid of oleic acid having retained the unsaturation of the original oleic acid.
- Possible structures for this type of product are the following:
- reaction with the monohydric and polyhydric alcohol esters of mono-olefinic acids proceeds in the same manner and under the same conditions described with reference to the free acid in the example.
- any of the peroxides listed above can be substituted for the ditertiary-butyl peroxide in the example and the process conducted under the same conditions to produce similar results.
- the quantity of peroxide may vary quite widely.
- the amount of polymer formed appears to be directly proportional to the amount of peroxide employed. If very small quantities are used small quantities of polymer are formed and it may be necessary to strip off large quantities of monomer to obtain a relatively pure or high concentration polymer. Where large quantities of peroxide are employed, there is some tendency for the formation of trimers and higher polymers. In general, from about 5 mol percent to 30 mol percent is preferred. Quantities outside this range may be used with the general eifect on results described above.
- Process of dimerizing a compound selected from the group consisting of higher fatty acids containing only one double bond. and lower aliphatic monohydric alcohol esters thereof which comprises heating said compound to a temperature in excess of 100 C. in the presence of organic peroxide having the formula ROOR in which R is a tertiary alkyls group and R is selected from the group consisting of tertiary alkyl and tertiary alkyl peroxyalkyl r p n i 2.
- Process of dimerizing a compound selected from the oup consisting of higher fatty acids containing only one double bond, and lower aliphatic monohydric alcohol esters thereof which comprises heating said compound to a temperature in excess of 100 C. in the presence of di-tertiary-butyl peroxide.
- Process of dimerizing oleic acid which comprises heating oleic acid to a temperature in excess of 100 C. in the presence of di-tertiary-butyl peroxide.
- Process of dimerizing oleic acid which comprises heating cleic acid to a temperature in the range of 130- 150 C. in the presence of di-tertiary-butyl peroxide.
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- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Lubricants (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
Description
DIMERIC FATTY ACIDS Stuart A. Harrison and Kirtland E. McCaleb, Minneapolis, Minn., assignors to General Mills, Inc, a corporation of Delaware No Drawing. Application August 1, 1951, Serial No. 239,846
4 Claims. (Cl. ZEN-46?) The present invention relates to a novel process of producing dimeric fatty acids and esters thereof, and to the resultant products. Polyesters, polyamides, and other derivatives of these dimeric fatty acids possess unusual properties which distinguish them from correspond ing products derived from other dimeric fatty acids. The dimeric fatty acids of the present invention are useful in the coating, resin, and fiber fields.
The present invention involves the dimerization of monoolefinic higher fatty acids to produce dimeric, and, to some extent, higher polmeric acids, which retain the unsaturation of the fatty acids from which they are derived. It is thus possible to produce dimeric acids from such unsaturated acids as oleic acid, which do not readily undergo polymerization in the usual thermal polymerization process. In addition, any polymers formed in the usual thermal polymerization of oleic acid are essentially saturated or contain one double bond per dimer molecule, whereas the polymeric acids of the present invention retain the unsaturation of the fatty acids employed.
It is therefore an object of the present invention to provide a novel process of producing dimeric fatty acids and esters thereof from mono-olefinic fatty acids, the polymeric acids retaining the unsaturation of the fatty acid starting material.
It is also an object of the present invention to provide novel dimeric higher fatty compounds derived from mono-olefinic acids and containing in the dimer the unsaturation of the original fatty acid.
The process involves the treatment, at temperatures in excess of 50 C., of higher fatty acids or esters thereof having only one double bond in the fatty group, with organic peroxides having the formula ROOR in which R is a tertiary alkyl group and R is selected from the group consisting of tertiary alkyl and tertiary alkyl peroxyalkyl groups. Typical of these peroxides are di-tertiary butyl peroxide; 2,2-bis-t-butylperoxy propane; 2,2-bis-t-butylperoxy butane; 2,2-bis-t-butylperoxy pentane; and 3,3-bist-butylperoxy pentane. The process is applicable to the free fatty acids containing from 8 to 22 carbon atoms, to the lower aliphatic esters thereof, as for example, the methyl esters, and to the polyhydric alcohol esters thereof, as for example, the glycerides and the pentaerythritol esters. Any higher fatty acid containing a single point of unsaturation may be employed in the present process. Commercially oleic acid is the principal acid readily available for this purpose, and accordingly the invention will be described with particular reference thereto.
The process involves merely mixing thefatty acid or its ester with the peroxide, and heating the mixture in an inert atmosphere for the required time at the required States atent O "ice temperature. In order to reduce the time period to a commercially practical point, temperatures in excess of C. are usually employed. Preferably the temper: atures are in the neighborhood of -l50 C., requiring time periods of 12 to 48 hours. At the completion of the reaction period, the reaction product may, if desired, be stripped under vacuum to remove all the decomposition products of the peroxide as well as any monomeric fatty acids or esters present therein. The resultant prodnot is essentially a dimeric acid or dimeric ester and contains smaller quantities of higher polymers. It will be appreciated that the removal of the decomposition prodnets and the monomeric fatty acids or esters is not essential if the product desired is a mixture of monomer and dimer and higher polymers.
Example The oleic acid employed in this example had an acid number of 198.4, and an iodine number of 88.7. 20 grams (0.971 mol) of this oleic acid and 0.75 g. (0.0051 moi) di-tertiary-butyl peroxide were heated without agitation in sealed bottles under nitrogen. The temperature was maintained at 130 C. for 24 hours. Then an additional 0.75 g. of di-tert-butyl peroxide was added, and the heating was continued for another 24 hours. The reaction mixture was then stripped under vacuum to remove volatile decomposition products. The rcsidue was distilled under high vacuum to remove monomeric acid and to yield a dimeric fraction and a polymeric residue. The following properties were found for the dimeric fraction (theoretical values for a dimer containing two nonconjugated double bonds per molecule of dimer acid are given in parentheses): molecular weight 548 (565); acid number 186.5 (198); iodine number (Rapid Wijs) 91.7 (89.9); spot at 231m 5.6 (0). This ultraviolet absorption may be due to the presence of a small amount of a conjugated isomer such as (1) below.
Thus it appears that the dimeric material is largely a dimer acid of oleic acid having retained the unsaturation of the original oleic acid. Possible structures for this type of product are the following:
The reaction with the monohydric and polyhydric alcohol esters of mono-olefinic acids proceeds in the same manner and under the same conditions described with reference to the free acid in the example. Similarly, any of the peroxides listed above can be substituted for the ditertiary-butyl peroxide in the example and the process conducted under the same conditions to produce similar results.
The quantity of peroxide may vary quite widely. The amount of polymer formed appears to be directly proportional to the amount of peroxide employed. If very small quantities are used small quantities of polymer are formed and it may be necessary to strip off large quantities of monomer to obtain a relatively pure or high concentration polymer. Where large quantities of peroxide are employed, there is some tendency for the formation of trimers and higher polymers. In general, from about 5 mol percent to 30 mol percent is preferred. Quantities outside this range may be used with the general eifect on results described above.
We claim as our invention:
1. Process of dimerizing a compound selected from the group consisting of higher fatty acids containing only one double bond. and lower aliphatic monohydric alcohol esters thereof, which comprises heating said compound to a temperature in excess of 100 C. in the presence of organic peroxide having the formula ROOR in which R is a tertiary alkyls group and R is selected from the group consisting of tertiary alkyl and tertiary alkyl peroxyalkyl r p n i 2. Process of dimerizing a compound selected from the oup consisting of higher fatty acids containing only one double bond, and lower aliphatic monohydric alcohol esters thereof, which comprises heating said compound to a temperature in excess of 100 C. in the presence of di-tertiary-butyl peroxide.
3. Process of dimerizing oleic acid which comprises heating oleic acid to a temperature in excess of 100 C. in the presence of di-tertiary-butyl peroxide.
4. Process of dimerizing oleic acid which comprises heating cleic acid to a temperature in the range of 130- 150 C. in the presence of di-tertiary-butyl peroxide.
References Cited in the file of this patent UNITED STATES PATENTS Whetstone et a1. Sept. 18, 1951 Wiebe Mar. 11, 1952 OTHER REFERENCES
Claims (1)
1. PROCESS OF DIMERIZING A COMPOUND SELECTED FROM THE GROUP CONSISTING OF HIGHER FATTY ACIDS CONTAINING ONLY ONE DOUBLE BOND, AND LOWER ALIPHATIC MONOHYDRIC ALOCHOL ESTERS THEREOF, WHICH COMPRISES HEATING SAID COMPOUND TO A TEMPERATURE IN EXCESS OF 100*C. IN THE PRESENCE OF ORGANIC PEROXIDE HAVING THE FORMULA ROOR1 IN WHICH R CONSISTING OF TERTIARY ALKYL AND TERITARY ALKYL PEROXYALKYL GROUPS.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US239846A US2731481A (en) | 1951-08-01 | 1951-08-01 | Dimeric fatty acids |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US239846A US2731481A (en) | 1951-08-01 | 1951-08-01 | Dimeric fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2731481A true US2731481A (en) | 1956-01-17 |
Family
ID=22903971
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US239846A Expired - Lifetime US2731481A (en) | 1951-08-01 | 1951-08-01 | Dimeric fatty acids |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2731481A (en) |
Cited By (31)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964545A (en) * | 1953-03-09 | 1960-12-13 | Gen Mills Inc | Dimeric fatty acids and esters thereof |
| US3008868A (en) * | 1957-12-23 | 1961-11-14 | Armstrong Cork Co | Drainage rate of cellulosic papermaking slurries |
| US3093609A (en) * | 1959-02-24 | 1963-06-11 | Armstrong Cork Co | Binder dispersion for beater saturation processes |
| US3244596A (en) * | 1962-10-18 | 1966-04-05 | Univ Iowa College Of Pharmacy | Coated medicinal agents and coating compositions therefor |
| DE1280852B (en) * | 1959-08-24 | 1968-10-24 | Unilever Emery | Process for dimerizing unsaturated fatty acids |
| US3429817A (en) * | 1968-02-29 | 1969-02-25 | Exxon Research Engineering Co | Diester lubricity additives and oleophilic liquids containing the same |
| US3897468A (en) * | 1974-02-15 | 1975-07-29 | Emery Industries Inc | Polybasic acid compositions obtained from polymerized fatty acids |
| US4327030A (en) * | 1981-02-13 | 1982-04-27 | Emery Industries, Inc. | Process for reducing the polyunsaturates content in mixtures of unsaturated fatty acids and/or fatty acid esters |
| US5321098A (en) * | 1991-10-04 | 1994-06-14 | The Lubrizol Corporation | Composition and polymer fabrics treated with the same |
| EP0684298A2 (en) | 1994-05-23 | 1995-11-29 | The Lubrizol Corporation | Compositions for extending seal life, and lubricants and functional fluids containing the same |
| EP0695799A2 (en) | 1994-08-03 | 1996-02-07 | The Lubrizol Corporation | Combination of a sulfer compound and specific phosphorus compounds and their use in lubricating compositions, concentrates and greases |
| EP0695798A2 (en) | 1994-08-03 | 1996-02-07 | The Lubrizol Corporation | Lubricating compositions, concentrates, and greases containing the combination of an organic polysulfide and an overbased composition or a phosphorus or boron compound |
| US6518226B2 (en) | 1997-05-20 | 2003-02-11 | The Procter & Gamble Co. | Flowable composition and a process for making the flowable composition |
| US6562394B1 (en) | 1998-05-20 | 2003-05-13 | The Procter & Gamble Co. | Flowable nondigestible oil and process for making |
| US6573223B1 (en) | 2002-03-04 | 2003-06-03 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
| US6835324B1 (en) * | 1999-02-25 | 2004-12-28 | Arizona Chemical Company | Method for isolating oleic acid and producing lineloic dimer/trimer acids via selective reactivity |
| US20050123665A1 (en) * | 1997-04-21 | 2005-06-09 | Cerreta Michael K. | Process for making a flowable nondigestible oil |
| EP2058381A1 (en) | 2002-11-25 | 2009-05-13 | Elementis Specialties, Inc. | Compositions for drilling fluids useful to provide flat temperature rheology to such fluids over a wide temperature range and drilling fluids containing such compositions |
| US20090163386A1 (en) * | 2002-11-27 | 2009-06-25 | Elementis Specialties, Inc. | Compositions for drilling fluids useful to produce flat temperature rheology to such fluids over a wide temperature range and drilling fluids containing such compositions |
| US20090183649A1 (en) * | 2005-03-23 | 2009-07-23 | Elementis Specialties, Inc. | Compositions Useful to Provide Improved Rheology and Mist Control to Ink Formulations and Ink Formulations Containing Such Compositions |
| US20090227478A1 (en) * | 2008-03-07 | 2009-09-10 | Elementis Specialties, Inc. | Equivalent circulating density control in deep water drilling |
| US20100009873A1 (en) * | 2007-10-22 | 2010-01-14 | Elementis Specialties , Inc. | Thermally Stable Compositions and Use Thereof in Drilling Fluids |
| WO2013101256A2 (en) | 2011-12-30 | 2013-07-04 | Butamax (Tm) Advanced Biofuels Llc | Corrosion inhibitor compositions for oxygenated gasolines |
| WO2013151911A1 (en) | 2012-04-04 | 2013-10-10 | The Lubrizol Corporation | Bearing lubricants for pulverizing equipment |
| EP2746372A1 (en) | 2012-12-21 | 2014-06-25 | Afton Chemical Corporation | Additive compositions with plural friction modifiers |
| CN104870206A (en) * | 2012-12-17 | 2015-08-26 | 米其林企业总公司 | Tyre comprising a rubber composition comprising an epoxide elastomer crosslinked with a polycarboxylic acid |
| CN104884268A (en) * | 2012-12-17 | 2015-09-02 | 米其林企业总公司 | Tyre comprising a rubber composition comprising an epoxide polymer crosslinked with a polycarboxylic acid |
| US10421858B2 (en) | 2014-06-18 | 2019-09-24 | Compagnie Generale Des Etablissements Michelin | Rubber composition comprising an epoxide elastomer cross-linked by a polycarboxylic acid |
| WO2020150123A1 (en) | 2019-01-17 | 2020-07-23 | The Lubrizol Corporation | Traction fluids |
| WO2020229804A1 (en) | 2019-05-15 | 2020-11-19 | Innospec Limited | Compositions and methods and uses relating thereto |
| WO2023034764A1 (en) | 2021-08-30 | 2023-03-09 | Axalta Coating Systems Ip Co., Llc | Method of applying a coating composition to a substrate |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2568426A (en) * | 1949-06-06 | 1951-09-18 | Shell Dev | Condensation products from polyethylenic-unsaturated aldehyde adducts, derivatives thereof, and methods for producing the same |
| US2588902A (en) * | 1952-03-11 | Peroxide treatment of fatty oils |
-
1951
- 1951-08-01 US US239846A patent/US2731481A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2588902A (en) * | 1952-03-11 | Peroxide treatment of fatty oils | ||
| US2568426A (en) * | 1949-06-06 | 1951-09-18 | Shell Dev | Condensation products from polyethylenic-unsaturated aldehyde adducts, derivatives thereof, and methods for producing the same |
Cited By (47)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2964545A (en) * | 1953-03-09 | 1960-12-13 | Gen Mills Inc | Dimeric fatty acids and esters thereof |
| US3008868A (en) * | 1957-12-23 | 1961-11-14 | Armstrong Cork Co | Drainage rate of cellulosic papermaking slurries |
| US3093609A (en) * | 1959-02-24 | 1963-06-11 | Armstrong Cork Co | Binder dispersion for beater saturation processes |
| DE1280852B (en) * | 1959-08-24 | 1968-10-24 | Unilever Emery | Process for dimerizing unsaturated fatty acids |
| DE1280852C2 (en) * | 1959-08-24 | 1974-05-22 | Unilever Emery | Process for dimerizing unsaturated fatty acids |
| US3244596A (en) * | 1962-10-18 | 1966-04-05 | Univ Iowa College Of Pharmacy | Coated medicinal agents and coating compositions therefor |
| US3429817A (en) * | 1968-02-29 | 1969-02-25 | Exxon Research Engineering Co | Diester lubricity additives and oleophilic liquids containing the same |
| US3897468A (en) * | 1974-02-15 | 1975-07-29 | Emery Industries Inc | Polybasic acid compositions obtained from polymerized fatty acids |
| US4327030A (en) * | 1981-02-13 | 1982-04-27 | Emery Industries, Inc. | Process for reducing the polyunsaturates content in mixtures of unsaturated fatty acids and/or fatty acid esters |
| US5362555A (en) * | 1991-10-04 | 1994-11-08 | Kasturi Lal | Compositions and polymer fabrics treated with the same |
| US5321098A (en) * | 1991-10-04 | 1994-06-14 | The Lubrizol Corporation | Composition and polymer fabrics treated with the same |
| EP0684298A2 (en) | 1994-05-23 | 1995-11-29 | The Lubrizol Corporation | Compositions for extending seal life, and lubricants and functional fluids containing the same |
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