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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- fatty acids
- dimeric
- acid
- esters
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- 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)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Polymerization Catalysts (AREA)
- Lubricants (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 |
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Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US239846A Expired - Lifetime US2731481A (en) | 1951-08-01 | 1951-08-01 | Dimeric fatty acids |
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| 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 |
| 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 |
| US20050123665A1 (en) * | 1997-04-21 | 2005-06-09 | Cerreta Michael K. | Process for making a flowable nondigestible oil |
| US7276485B1 (en) | 1997-04-21 | 2007-10-02 | The Procter + Gamble Co. | Flowable nondigestible oil and process for making |
| 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 |
| 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 |
| US6573223B1 (en) | 2002-03-04 | 2003-06-03 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
| WO2003076557A1 (en) | 2002-03-04 | 2003-09-18 | The Lubrizol Corporation | Lubricating compositions with good thermal stability and demulsibility properties |
| EP2292716A1 (en) | 2002-11-25 | 2011-03-09 | 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 |
| 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 |
| US7837776B2 (en) | 2005-03-23 | 2010-11-23 | Elementis Specialties, Inc. | Compositions useful to provide improved rheology and mist control to ink formulations and ink formulations 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 |
| US20100009873A1 (en) * | 2007-10-22 | 2010-01-14 | Elementis Specialties , Inc. | Thermally Stable Compositions and Use Thereof in Drilling Fluids |
| US7906461B2 (en) | 2007-10-22 | 2011-03-15 | Elementis Specialties, Inc. | Thermally stable compositions and use thereof in drilling fluids |
| US8809240B2 (en) | 2008-03-07 | 2014-08-19 | Elementis Specialties, Inc. | Equivalent circulating density control in deep water drilling |
| US7799742B2 (en) | 2008-03-07 | 2010-09-21 | Elementis Specialties Inc. | Equivalent circulating density control in deep water drilling |
| US20100323927A1 (en) * | 2008-03-07 | 2010-12-23 | 329 Elementis Specialties Inc. | Equivalent circulating density control in deep water drilling |
| US7956015B2 (en) | 2008-03-07 | 2011-06-07 | Elementis Specialties, Inc. | Equivalent circulating density control in deep water drilling |
| US20090227478A1 (en) * | 2008-03-07 | 2009-09-10 | Elementis Specialties, Inc. | Equivalent circulating density control in deep water drilling |
| 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 |
| US20150337109A1 (en) * | 2012-12-17 | 2015-11-26 | Compagnie Generale Des Etablissements Michelin | Tire comprising a rubber composition comprising an epoxide elastomer crosslinked with a polycarboxylic acid |
| 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 |
| US20150322234A1 (en) * | 2012-12-17 | 2015-11-12 | Compagnie Generale Des Etablissements Michelin | Tire comprising a rubber composition comprising an epoxide polymer crosslinked with a polycarboxylic acid |
| CN104884268B (en) * | 2012-12-17 | 2018-04-06 | 米其林企业总公司 | Include the tire of the rubber composition containing useful polycarboxylic acid crosslinked epoxy polymer |
| EP2746372A1 (en) | 2012-12-21 | 2014-06-25 | Afton Chemical Corporation | Additive compositions with plural friction modifiers |
| 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 |
| US11261389B2 (en) | 2019-05-15 | 2022-03-01 | 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 |
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