US3899476A - Process for making a methacrylic acid adduct of linoleic acid and product - Google Patents
Process for making a methacrylic acid adduct of linoleic acid and product Download PDFInfo
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- US3899476A US3899476A US465160A US46516074A US3899476A US 3899476 A US3899476 A US 3899476A US 465160 A US465160 A US 465160A US 46516074 A US46516074 A US 46516074A US 3899476 A US3899476 A US 3899476A
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- acid
- conjugated
- linoleic
- dicarboxylic acid
- fatty
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- OYHQOLUKZRVURQ-IXWMQOLASA-N linoleic acid Natural products CCCCC\C=C/C\C=C\CCCCCCCC(O)=O OYHQOLUKZRVURQ-IXWMQOLASA-N 0.000 title claims abstract description 21
- 238000000034 method Methods 0.000 title claims abstract description 19
- CERQOIWHTDAKMF-UHFFFAOYSA-N Methacrylic acid Chemical compound CC(=C)C(O)=O CERQOIWHTDAKMF-UHFFFAOYSA-N 0.000 title claims abstract description 17
- OYHQOLUKZRVURQ-HZJYTTRNSA-N Linoleic acid Chemical compound CCCCC\C=C/C\C=C/CCCCCCCC(O)=O OYHQOLUKZRVURQ-HZJYTTRNSA-N 0.000 title claims abstract description 15
- 235000020778 linoleic acid Nutrition 0.000 title abstract description 13
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims abstract description 17
- 238000005698 Diels-Alder reaction Methods 0.000 claims abstract description 11
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 42
- 229930195729 fatty acid Natural products 0.000 claims description 42
- 239000000194 fatty acid Substances 0.000 claims description 42
- 150000004665 fatty acids Chemical class 0.000 claims description 42
- 239000000203 mixture Substances 0.000 claims description 21
- 229940108924 conjugated linoleic acid Drugs 0.000 claims description 9
- 239000003784 tall oil Substances 0.000 claims description 9
- JBYXPOFIGCOSSB-GOJKSUSPSA-N 9-cis,11-trans-octadecadienoic acid Chemical compound CCCCCC\C=C\C=C/CCCCCCCC(O)=O JBYXPOFIGCOSSB-GOJKSUSPSA-N 0.000 claims description 8
- 239000002253 acid Substances 0.000 claims description 8
- HGCIXCUEYOPUTN-UHFFFAOYSA-N cyclohexene Chemical compound C1CCC=CC1 HGCIXCUEYOPUTN-UHFFFAOYSA-N 0.000 claims description 8
- 239000011630 iodine Substances 0.000 claims description 7
- 229910052740 iodine Inorganic materials 0.000 claims description 7
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 claims description 3
- 239000000061 acid fraction Substances 0.000 claims description 2
- 150000007513 acids Chemical class 0.000 claims description 2
- 229960004232 linoleic acid Drugs 0.000 claims 3
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 4
- 125000000896 monocarboxylic acid group Chemical group 0.000 abstract description 4
- 238000006243 chemical reaction Methods 0.000 description 13
- 229940063559 methacrylic acid Drugs 0.000 description 12
- ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 6
- 239000003054 catalyst Substances 0.000 description 6
- 239000000047 product Substances 0.000 description 5
- 230000015572 biosynthetic process Effects 0.000 description 4
- 150000001991 dicarboxylic acids Chemical class 0.000 description 3
- 238000004519 manufacturing process Methods 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 238000005580 one pot reaction Methods 0.000 description 3
- 238000003786 synthesis reaction Methods 0.000 description 3
- 150000001408 amides Chemical class 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000004820 halides Chemical class 0.000 description 2
- 239000000057 synthetic resin Substances 0.000 description 2
- 229920003002 synthetic resin Polymers 0.000 description 2
- OYHQOLUKZRVURQ-NTGFUMLPSA-N (9Z,12Z)-9,10,12,13-tetratritiooctadeca-9,12-dienoic acid Chemical compound C(CCCCCCC\C(=C(/C\C(=C(/CCCCC)\[3H])\[3H])\[3H])\[3H])(=O)O OYHQOLUKZRVURQ-NTGFUMLPSA-N 0.000 description 1
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 1
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 1
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 1
- 235000003255 Carthamus tinctorius Nutrition 0.000 description 1
- 244000020518 Carthamus tinctorius Species 0.000 description 1
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
- 244000068988 Glycine max Species 0.000 description 1
- 235000010469 Glycine max Nutrition 0.000 description 1
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 1
- 239000005642 Oleic acid Substances 0.000 description 1
- 235000008753 Papaver somniferum Nutrition 0.000 description 1
- 240000001090 Papaver somniferum Species 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- 235000004443 Ricinus communis Nutrition 0.000 description 1
- 238000004458 analytical method Methods 0.000 description 1
- 150000008064 anhydrides Chemical class 0.000 description 1
- 239000010775 animal oil Substances 0.000 description 1
- 230000003197 catalytic effect Effects 0.000 description 1
- 238000012512 characterization method Methods 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 235000012343 cottonseed oil Nutrition 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 238000001030 gas--liquid chromatography Methods 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000004014 plasticizer Substances 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000728 polyester Polymers 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 238000000926 separation method Methods 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 235000015112 vegetable and seed oil Nutrition 0.000 description 1
- 239000008158 vegetable oil Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09F—NATURAL RESINS; FRENCH POLISH; DRYING-OILS; DRIERS (SICCATIVES); TURPENTINE
- C09F1/00—Obtaining purification, or chemical modification of natural resins, e.g. oleo-resins
- C09F1/04—Chemical modification, e.g. esterification
Definitions
- the invention relates to the production of a cycloaliphatic dicarboxylic acid of 22 carbon atoms or C dicarboxylic acid. More specifically, the cy cloaliphatic C -dicarboxylicacid is prepared by a one-step reaction of methacrylic acid as the dienophile and an iodine catalyst in the formation of a Diels-Alder type adduct with both non-conjugated and conjugated linoleic acid. As used herein, the cycloaliphatic C -dicarboxylic acid may, in some instances, include minor amounts of dicarboxylic acids of other molecular weight, for example, a C -dicarboxylic acid. 1
- Diels-Alder adduct synthesis also known as diene synthesis, involves .the reaction of a dienophile with normally conjugated compounds including fatty acids.
- Diels-Alder synthesis is well known in .the prior art in the reaction of dienophiles with fattyacids as exemplified in a paper entitled Reactions of Conjugated Fatty Acids.
- a general 'object of this invention to provide a process for making a Cgi-c yeloaliphatic dicarboxylic acid from all of the available linoleic acid-in a fatty acid mixture.
- Another object of this invention is to provide a process whereby tall oil fatty acids, in particular, may be easily separated into a C -dicarboxylic acid portion and an oleic acid-type portion.
- the linoleic acid used in the process of the present synthesis may be obtained from any naturally occurring fatty acid mixture source containing both nonc'onjugated and conjugated linoleic acids.
- fatty acid mixtures obtained from tall oil or from such other sources than tall oil as animal or vegetable oils, such as soybean fatty acid, safflower fatty acid, dehydrated castor fatty acids, cottonseed, poppy,-as well as pure linoleic acid.
- the reaction is carried out in the presence of a minor amount of iodine, the same acting as a catalyst, and thus ensuring complete conversion of both the nonconjugated and conjugated diene linoleic acid and involving an advantageous one-step reaction to a cycloaliphatic C -dicarboxylic acid having the formula wherein and y are integers from 3 to 9, x and y together equal 12, and one X is CH and the other X is Complete conversion to the C -dicarboxylic acid is further assured by having methacrylic acid present in an amount up to about 30% by weight of the linoleic acid.
- the catalytic amounts of iodine used is from 0.01% to 0.50% based on the weight of linoleic acid, preferably 0.05% to 0.2% by weight.
- tall oilfatty acid mixture includes both conjugated and nonconjugated linoleic acid.
- Methacrylic reacts to convert the totaldiene portion of said fatty acids to dicarboxylic acid.
- the amount of methacrylic acid and iodine catalyst used are based upon the total linoleic acid present in the tall oil fatty acid mixture.
- the cycloaliphatic -dicarboxylic acid of the present invention is useful as a plasticizer, lubricant, soap base, curing agent, or synthetic resin, and chemical intermediate, as in the format on of esters, amides, acid halides, and particularly in the field of synthetic resins involving reaction products of the dicarboxylic acid or functional derivatives thereof, (esters, anhydrides, acid halides, amides), polyesters and polyamides.
- a 1 liter laboratory autoclave was charged with 500 grams of a distilled tall oil fatty acid containing both conjugated and non-conjugated linoleic fatty acids. To the fatty acid mixture was added 0.5 grams of iodine and 77.5 grams of methacrylic acid. The autoclave was sealed and heated at 250C.-260C. for 2 hours. Maximum pressure during the reaction was 40 psi. The yield of C DiAcid as measured by gas/liquid chromatography was 13.9%. The product had a saponification number of 238.5 and an acid number of2 l 5.4. The majority of the remaining portion of the fatty acid mixture following the reaction was an oleic type acid.
- EXAMPLE 2 This example illustrates the separation and characterization of the C -dicarboxylic acid.
- the fatty acid mixture from Example 1 containing the C dicarboxylic acid was pot-distilled under vacuum to remove the mono-carboxylic fatty acids (approximately 55.6% by weight).
- the undistilled portion was then run through a wiped film evaporator to distill the C dicarboxylic acid adduct fraction.
- the yield of the distilled adduct was 75% based on linoleic acid feed and had the following analysis:
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- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
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- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
A process for making a Diels-Alder type adduct of methacrylic acid and linoleic acid forming a cycloaliphatic dicarboxylic acid of 22 carbon atoms having the formula
wherein x and y are integers from 3 to 9, x and y together equal 12, and one X is CH2 and the other X is a -C(CH3)COOH group.
wherein x and y are integers from 3 to 9, x and y together equal 12, and one X is CH2 and the other X is a -C(CH3)COOH group.
Description
United States Patent 1191 Ward [451 Aug. 12, 1975 PROCESS FOR MAKING A METHACRYLIC ACID ADDUCT OF LINOLEIC ACID AND PRODUCT [75] Inventor: Benjamin F. Ward, Isle of Palms,
211 Appl. No.: 465,160
[52] US. Cl 260/975; 260/468 R; 260/514 K [51] Int. Cl. C09F l/OO; C09F 7/02 [58] Field of Search 260/97.5, 97.6, 419, 468 R,
[56] References Cited UNITED STATES PATENTS 3,753,968 8/1973 Ward 260/975 Primary ExaminerMelvyn I. Marquis Assistant ExaminerWilliam E. Parker Attorney, Agent, or Firm-Dennison, Dennison, Townshend & Meserole 57 ABSTRACT A process for making a Diels-Alder type adduct of methacrylic acid and linoleic acid forming a cycloaliphatic dicarboxylic acid of 22 carbon atoms having the formula wherein x and y are integers from 3 to 9, x and y together equal 12, and one X is CH and the other X is a C(CH )COOH group.
7 Claims, N0 Drawings PROCESS FOR MAKINGA .METHACRYLIC-ACID ADDUCT OF LINOLEIC ACID AND PRODUCT.
BACKGROUND oF THE INVENTION 1. Field ofthe Invention. r
The invention relates to the production of a cycloaliphatic dicarboxylic acid of 22 carbon atoms or C dicarboxylic acid. More specifically, the cy cloaliphatic C -dicarboxylicacid is prepared by a one-step reaction of methacrylic acid as the dienophile and an iodine catalyst in the formation of a Diels-Alder type adduct with both non-conjugated and conjugated linoleic acid. As used herein, the cycloaliphatic C -dicarboxylic acid may, in some instances, include minor amounts of dicarboxylic acids of other molecular weight, for example, a C -dicarboxylic acid. 1
2. The Prior Art Diels-Alder adduct synthesis, also known as diene synthesis, involves .the reaction of a dienophile with normally conjugated compounds including fatty acids. The Diels-Alder synthesis is well known in .the prior art in the reaction of dienophiles with fattyacids as exemplified in a paper entitled Reactions of Conjugated Fatty Acids. IV. Diels-Alder Adducts of 9,1 l- Octadecadienoic Acid by Teter et al., Journal of Drganic Chemistry, Vol. 22, page 512, (l957) In that paper there is described adducts of dien ophiles with fatty acids; but there is no disclosure of the reaction of both non-conjugated and conjugated portions of fatty acids in one-step reaction to form the C dicarboxylic acids. Additionally, such other prior art teachings of reactions of fatty acids are described in Ward, U.S. Pat. No. 3,753,'968,which describes the production of a C -cycloalip'hatic dicarboxylic acid;
It is, therefore, a general 'object of this invention to provide a process for making a Cgi-c yeloaliphatic dicarboxylic acid from all of the available linoleic acid-in a fatty acid mixture. Another object of this invention is to provide a process whereby tall oil fatty acids, in particular, may be easily separated into a C -dicarboxylic acid portion and an oleic acid-type portion.
Other objects, features and advantages will be evident from the foregoing disclosure.
SUMMARY OF THE INVENTION A process for making a Diels-Alder type adduct of methacrylic acid and linoleic acid forming a cycloaliphatic dicarboxylic acid of 22 carbon atoms having the formula wherein .i' and y are integers from 3 to 9, and y together equal 12, and one X is CH and the other X is a C(CH;,)COOH group, wherein both the nonconjugated and conjugated linoleic acid-portions of the fatty acid are simultaneously reacted with up to 30% by weight of methacrylic acid and 0.01% to 0.50% by weight of said fatty acid mixture of iodine at a tempera ture between 200C. and 270C.
DETAILED DESCRIPTION OF THE INVENTION The linoleic acid used in the process of the present synthesis may be obtained from any naturally occurring fatty acid mixture source containing both nonc'onjugated and conjugated linoleic acids. Especially satisfactory are fatty acid mixtures obtained from tall oil or from such other sources than tall oil as animal or vegetable oils, such as soybean fatty acid, safflower fatty acid, dehydrated castor fatty acids, cottonseed, poppy,-as well as pure linoleic acid.
The reaction is carried out in the presence of a minor amount of iodine, the same acting as a catalyst, and thus ensuring complete conversion of both the nonconjugated and conjugated diene linoleic acid and involving an advantageous one-step reaction to a cycloaliphatic C -dicarboxylic acid having the formula wherein and y are integers from 3 to 9, x and y together equal 12, and one X is CH and the other X is Complete conversion to the C -dicarboxylic acid is further assured by having methacrylic acid present in an amount up to about 30% by weight of the linoleic acid. The catalytic amounts of iodine used is from 0.01% to 0.50% based on the weight of linoleic acid, preferably 0.05% to 0.2% by weight.
.As described in U.S. Pat. No. 3,753,968, tall oilfatty acid mixture includes both conjugated and nonconjugated linoleic acid. Methacrylic reacts to convert the totaldiene portion of said fatty acids to dicarboxylic acid. The amount of methacrylic acid and iodine catalyst used are based upon the total linoleic acid present in the tall oil fatty acid mixture.
The use of large percentages of iodine, i.e., above 0.5% or if the temperature is increased above 270C. a portion'of the linoleic acid-is converted to oleic acid and the yield of dicarboxylic acid is thereby decreased. There is a lower limit of feasibility too, for at just slightly milder reaction conditions the rate drops to almost zero. In order to maintain the highest possible yield of dicarboxylic acid from a mixed fatty acid, conditions close to the lower catalyst level and lower temperature are maintained. Selection of the ideal amount of catalyst will depend on the equipment, temperature and time of the reaction. The reaction to produce dicarboxylic acids is carried out at a temperature of 200C. and 270C, preferably 230C. to 260C. The reaction time at these temperatures and under the preferred catalyst level is about I to 2 hours.
The cycloaliphatic -dicarboxylic acid of the present invention is useful as a plasticizer, lubricant, soap base, curing agent, or synthetic resin, and chemical intermediate, as in the format on of esters, amides, acid halides, and particularly in the field of synthetic resins involving reaction products of the dicarboxylic acid or functional derivatives thereof, (esters, anhydrides, acid halides, amides), polyesters and polyamides.
The practice of this invention may clearly be seen in the following examples:
EXAMPLE I To illustrate the production of a C -dicarboxylic acid using the process of the subject invention, the following example was performed.
A 1 liter laboratory autoclave was charged with 500 grams of a distilled tall oil fatty acid containing both conjugated and non-conjugated linoleic fatty acids. To the fatty acid mixture was added 0.5 grams of iodine and 77.5 grams of methacrylic acid. The autoclave was sealed and heated at 250C.-260C. for 2 hours. Maximum pressure during the reaction was 40 psi. The yield of C DiAcid as measured by gas/liquid chromatography was 13.9%. The product had a saponification number of 238.5 and an acid number of2 l 5.4. The majority of the remaining portion of the fatty acid mixture following the reaction was an oleic type acid.
EXAMPLE 2 This example illustrates the separation and characterization of the C -dicarboxylic acid. The fatty acid mixture from Example 1 containing the C dicarboxylic acid was pot-distilled under vacuum to remove the mono-carboxylic fatty acids (approximately 55.6% by weight). The undistilled portion was then run through a wiped film evaporator to distill the C dicarboxylic acid adduct fraction. The yield of the distilled adduct was 75% based on linoleic acid feed and had the following analysis:
Saponiflcation Number 304 Acid Number 2l6 Gardner Color Number 5 dicarboxylic acid from a fatty acid mixture containing conjugated linoleic acid and non-conjugated linoleic acid comprising,
simultaneously reacting both the non-conjugated and conjugated linoleic acid portion of the fatty acid mixture with up to 30% by weight of said fatty acids, methacrylic acid and 0.01% to 0.50% by weight of said fatty acid mixture of iodine at a temperature between 250C. and 260C. to convert the conjugated and non-conjugated linoleic acid portion to a dicarboxylic acid having the formula CH=CH 0 wherein x and y are integers from 3 to 9, x and y together equal 12, and one X is CH; and the other X is a C(CH )COOH group.
2. The process of claim 1 wherein said fatty acid mixture is a tall oil fatty acid mixture.
3. The process of claim 1 further comprising,
distilling the fatty acid mixture containing the C dicarboxylic acid and recovering a linoleic-free fatty acid fraction and a C -dicarboxylic acid fraction.
4. The product of the process of claim 1.
5. The product of the process of claim 2.
6. A cyclohexene C -dicarboxylic acid Diels-Alder type adduct of methacrylic acid and linoleic conjugated and non-conjucated acids.
7. A cyclohexene C -dicarboxylic acid Diels-Alder type adduct of methacrylic acid and tall oil fatty acids containing both conjugated and non-conjugated linoleic acid.
Claims (7)
1. A PROCESS FOR FORMING A CYCLOALIPHATIC C22-DICARBOXYLIC ACID FROM A FATTY ACID MIXTURE CONTAINING CONJUGATED LINOLIC ACID AND NON-CONJUGATED LINOLIC ACID COMPRISING, SIMULTANEOUSLY REACTING BOTH THE NON-CONJUGATED AND CONJUGATED LINOLEIC ACID PORTION OF THE FATTY ACID MIXTURE WITH UP TO 30% BY WEIGHT OF SAID FATTY ACIDS, METHACRYLIC ACID AND 0.01% TO 0.50% BY WEIGHT OF SAID FATTY ACID MIXTURE OF IODINE AT A TEMPERATURE BETWEEN 250*C AND 260*C. TO CONVERT THE CONJUGATED AND NON-LINOLEIC ACID PORTION TO A DICARBOXYLIC ACID HAVING THE FORMULA
2. The process of claim 1 wherein said fatty acid mixture is a tall oil fatty acid mixture.
3. The process of claim 1 further comprising, distilling the fatty acid mixture containing the C22-dicarboxylic acid and recovering a linoleic-free fatty acid fraction and a C22-dicarboxylic acid fraction.
4. The product of the process of claim 1.
5. The product of the process of claim 2.
6. A cyclohexene C22-dicarboxylic acid Diels-Alder type adduct of methacrylic acid and linoleic conjugated and non-conjucated acids.
7. A cyclohexene C22-dicarboxylic acid Diels-Alder type adduct of methacrylic acid and tall oil fatty acids containing both conjugated and non-conjugated linoleic acid.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US465160A US3899476A (en) | 1974-04-29 | 1974-04-29 | Process for making a methacrylic acid adduct of linoleic acid and product |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US465160A US3899476A (en) | 1974-04-29 | 1974-04-29 | Process for making a methacrylic acid adduct of linoleic acid and product |
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| Publication Number | Publication Date |
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| US3899476A true US3899476A (en) | 1975-08-12 |
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Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293305A (en) * | 1979-11-01 | 1981-10-06 | Northwestern Laboratories, Inc. | Diester composition and textile processing compositions therefrom |
| US4394126A (en) * | 1979-11-01 | 1983-07-19 | Wilson Robert B | Diester composition and textile processing compositions therefrom |
| DE3316906A1 (en) * | 1982-05-17 | 1983-11-17 | Westvaco Corp., 10171 New York, N.Y. | AMPHOTERIC SUBSTANCES AS EMULSIFIERS FOR BITUMINOESE EMULSIONS |
| US4447269A (en) * | 1982-07-13 | 1984-05-08 | Westvaco Corporation | Cationic aqueous bituminous emulsion-aggregate slurries |
| US4462840A (en) * | 1983-06-20 | 1984-07-31 | Westvaco Corporation | Mixing of asphalt emulsion and aggregate in aqueous bituminous emulsion-aggregate slurries |
| US4464286A (en) * | 1982-04-26 | 1984-08-07 | Westvaco Corporation | Cationic bituminous emulsions |
| US4478642A (en) * | 1983-06-20 | 1984-10-23 | Westvaco Corporation | Amphoterics as emulsifiers for bituminous emulsions |
| US4494992A (en) * | 1983-06-20 | 1985-01-22 | Westvaco Corporation | Amphoterics as emulsifiers for bituminous emulsions |
| US4517110A (en) * | 1982-11-15 | 1985-05-14 | Agency Of Industrial Science And Technology | Rust preventive agent of hydroxypolybasic acid salt type |
| US4968496A (en) * | 1987-08-11 | 1990-11-06 | Grillo-Werke Ag | Deodorants and the preparation and use thereof |
| US5336438A (en) * | 1989-05-22 | 1994-08-09 | Westvaco Corporation | Rapid and medium setting high float bituminous emulsions from difficult asphalts |
| US5596032A (en) * | 1994-05-27 | 1997-01-21 | Westvaco Corporation | Slow-setting bituminous emulsions |
| DE4110762C2 (en) * | 1989-10-26 | 2001-05-03 | Harima Chemicals Inc | Decolorizing agent for the processing of printed waste paper |
| US20030091654A1 (en) * | 2000-09-21 | 2003-05-15 | Katz David P. | Methods for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols |
| US20170107440A1 (en) * | 2015-10-15 | 2017-04-20 | Ingevity South Carolina, Llc | Lubricating compositions and methods for the use thereof |
Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753968A (en) * | 1971-07-01 | 1973-08-21 | Westvaco Corp | Selective reaction of fatty acids and their separation |
-
1974
- 1974-04-29 US US465160A patent/US3899476A/en not_active Expired - Lifetime
Patent Citations (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3753968A (en) * | 1971-07-01 | 1973-08-21 | Westvaco Corp | Selective reaction of fatty acids and their separation |
Cited By (22)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4293305A (en) * | 1979-11-01 | 1981-10-06 | Northwestern Laboratories, Inc. | Diester composition and textile processing compositions therefrom |
| US4394126A (en) * | 1979-11-01 | 1983-07-19 | Wilson Robert B | Diester composition and textile processing compositions therefrom |
| US4464286A (en) * | 1982-04-26 | 1984-08-07 | Westvaco Corporation | Cationic bituminous emulsions |
| DE3316906A1 (en) * | 1982-05-17 | 1983-11-17 | Westvaco Corp., 10171 New York, N.Y. | AMPHOTERIC SUBSTANCES AS EMULSIFIERS FOR BITUMINOESE EMULSIONS |
| US4464285A (en) * | 1982-05-17 | 1984-08-07 | Westvaco Corporation | Amphoterics as emulsifiers for bituminous emulsions |
| US4447269A (en) * | 1982-07-13 | 1984-05-08 | Westvaco Corporation | Cationic aqueous bituminous emulsion-aggregate slurries |
| US4517110A (en) * | 1982-11-15 | 1985-05-14 | Agency Of Industrial Science And Technology | Rust preventive agent of hydroxypolybasic acid salt type |
| US4462840A (en) * | 1983-06-20 | 1984-07-31 | Westvaco Corporation | Mixing of asphalt emulsion and aggregate in aqueous bituminous emulsion-aggregate slurries |
| US4478642A (en) * | 1983-06-20 | 1984-10-23 | Westvaco Corporation | Amphoterics as emulsifiers for bituminous emulsions |
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| US20060204517A1 (en) * | 2000-09-21 | 2006-09-14 | Katz David P | Methods for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols |
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| US20090060941A9 (en) * | 2000-09-21 | 2009-03-05 | Katz David P | Methods for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols |
| US20090136539A9 (en) * | 2000-09-21 | 2009-05-28 | Katz David P | Methods for the treatment of diabetes, the reduction of body fat, improvement of insulin sensitivity, reduction of hyperglycemia, and reduction of hypercholesterolemia with chromium complexes, conjugated fatty acids, and/or conjugated fatty alcohols |
| US20170107440A1 (en) * | 2015-10-15 | 2017-04-20 | Ingevity South Carolina, Llc | Lubricating compositions and methods for the use thereof |
| US9879200B2 (en) * | 2015-10-15 | 2018-01-30 | Ingevity South Carolina, Llc | Lubricating compositions and methods for the use thereof |
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