US3364248A - Novel dicyanoethylfattydiamines of fatty acids - Google Patents
Novel dicyanoethylfattydiamines of fatty acids Download PDFInfo
- Publication number
- US3364248A US3364248A US398438A US39843864A US3364248A US 3364248 A US3364248 A US 3364248A US 398438 A US398438 A US 398438A US 39843864 A US39843864 A US 39843864A US 3364248 A US3364248 A US 3364248A
- Authority
- US
- United States
- Prior art keywords
- dicyanoethylfattydiamines
- novel
- cyanoethyl
- fatty acids
- fatty
- 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
Links
- 235000014113 dietary fatty acids Nutrition 0.000 title description 4
- 229930195729 fatty acid Natural products 0.000 title description 4
- 239000000194 fatty acid Substances 0.000 title description 4
- 150000004665 fatty acids Chemical class 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 description 13
- NLHHRLWOUZZQLW-UHFFFAOYSA-N Acrylonitrile Chemical compound C=CC#N NLHHRLWOUZZQLW-UHFFFAOYSA-N 0.000 description 6
- VCAISILSXYFPGO-UHFFFAOYSA-N nonadecane-1,19-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCN VCAISILSXYFPGO-UHFFFAOYSA-N 0.000 description 5
- 239000000126 substance Substances 0.000 description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 5
- 150000004985 diamines Chemical class 0.000 description 4
- CJYCVQJRVSAFKB-UHFFFAOYSA-N octadecane-1,18-diamine Chemical compound NCCCCCCCCCCCCCCCCCCN CJYCVQJRVSAFKB-UHFFFAOYSA-N 0.000 description 4
- 239000003921 oil Substances 0.000 description 4
- 235000019198 oils Nutrition 0.000 description 4
- 125000001731 2-cyanoethyl group Chemical group [H]C([H])(*)C([H])([H])C#N 0.000 description 3
- -1 amino- Chemical class 0.000 description 3
- 238000005516 engineering process Methods 0.000 description 3
- 230000002209 hydrophobic effect Effects 0.000 description 3
- 238000000034 method Methods 0.000 description 3
- 150000001412 amines Chemical class 0.000 description 2
- 238000004458 analytical method Methods 0.000 description 2
- POIZGMCHYSVWDU-UHFFFAOYSA-N icosane-1,20-diamine Chemical compound NCCCCCCCCCCCCCCCCCCCCN POIZGMCHYSVWDU-UHFFFAOYSA-N 0.000 description 2
- 239000000543 intermediate Substances 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- IOQPZZOEVPZRBK-UHFFFAOYSA-N octan-1-amine Chemical compound CCCCCCCCN IOQPZZOEVPZRBK-UHFFFAOYSA-N 0.000 description 2
- 230000003647 oxidation Effects 0.000 description 2
- 238000007254 oxidation reaction Methods 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 150000003335 secondary amines Chemical class 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 239000004094 surface-active agent Substances 0.000 description 2
- 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
- UGFAIRIUMAVXCW-UHFFFAOYSA-N Carbon monoxide Chemical compound [O+]#[C-] UGFAIRIUMAVXCW-UHFFFAOYSA-N 0.000 description 1
- 239000004593 Epoxy Substances 0.000 description 1
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 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
- PLZVEHJLHYMBBY-UHFFFAOYSA-N Tetradecylamine Chemical compound CCCCCCCCCCCCCCN PLZVEHJLHYMBBY-UHFFFAOYSA-N 0.000 description 1
- 125000004103 aminoalkyl group Chemical group 0.000 description 1
- 230000000844 anti-bacterial effect Effects 0.000 description 1
- 238000013459 approach Methods 0.000 description 1
- 239000010426 asphalt Substances 0.000 description 1
- 239000003899 bactericide agent Substances 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- 229910002091 carbon monoxide Inorganic materials 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 238000003776 cleavage reaction Methods 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- VPNOHCYAOXWMAR-UHFFFAOYSA-N docosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCN VPNOHCYAOXWMAR-UHFFFAOYSA-N 0.000 description 1
- JRBPAEWTRLWTQC-UHFFFAOYSA-N dodecylamine Chemical compound CCCCCCCCCCCCN JRBPAEWTRLWTQC-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 235000019197 fats Nutrition 0.000 description 1
- 239000008396 flotation agent Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- BUHXFUSLEBPCEB-UHFFFAOYSA-N icosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCN BUHXFUSLEBPCEB-UHFFFAOYSA-N 0.000 description 1
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 1
- 150000004668 long chain fatty acids Chemical class 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- TWXDDNPPQUTEOV-FVGYRXGTSA-N methamphetamine hydrochloride Chemical compound Cl.CN[C@@H](C)CC1=CC=CC=C1 TWXDDNPPQUTEOV-FVGYRXGTSA-N 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- CMNNTQPNCIUZHD-UHFFFAOYSA-N n'-undecylmethanediamine Chemical compound CCCCCCCCCCCNCN CMNNTQPNCIUZHD-UHFFFAOYSA-N 0.000 description 1
- 239000005445 natural material Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid Chemical compound CCCCCCCC\C=C/CCCCCCCC(O)=O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920000768 polyamine Polymers 0.000 description 1
- 150000003141 primary amines Chemical class 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 230000015227 regulation of liquid surface tension Effects 0.000 description 1
- 230000007017 scission Effects 0.000 description 1
- 239000003549 soybean oil Substances 0.000 description 1
- 235000012424 soybean oil Nutrition 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- QHKIWQPIFXRUOW-UHFFFAOYSA-N tetracosan-1-amine Chemical compound CCCCCCCCCCCCCCCCCCCCCCCCN QHKIWQPIFXRUOW-UHFFFAOYSA-N 0.000 description 1
- 150000004670 unsaturated fatty acids Chemical class 0.000 description 1
- 235000021122 unsaturated fatty acids Nutrition 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C255/00—Carboxylic acid nitriles
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S516/00—Colloid systems and wetting agents; subcombinations thereof; processes of
- Y10S516/01—Wetting, emulsifying, dispersing, or stabilizing agents
- Y10S516/07—Organic amine, amide, or n-base containing
Definitions
- an object of this invention is to provide novel difunctional fatty compounds which are useful in various chemical technologies.
- Another object is to provide a novel class of fatty diamines, more particularly, dicyanoethylfattydiamines.
- Still another object is to provide novel methods for the manufacture of such dicyanoethylfattydiamines.
- a further object is to provide a novel class of compounds which are excellent intermediates for other tetrafunctional fatty compounds having valuable properties for various chemical technologies.
- the invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
- a novel class of fatty diamines may be prepared by reacting an aminoalkylfattyamine (described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962) with acrylonitrile.
- aminoalkylfattyamine described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962
- acrylonitrile for example, by reacting aminoethylstearylamine with acrylonitrile in the presence of water, N,N-difl-cyanoethyl) aminoethylstearylamine is obtained.
- Such a compound is useful as an intermediate for forming a di- (aminoalkyl) fatty diamine which is useful as a surfactant, particularly as a flotation agent or an asphalt emulsifier, or as an epoxy curing agent. It also is useful as a bactericide.
- Example I.-N,N'-ai-(fi-cyanoethyl) aminostearylamine A two-liter four-neck Morton flask equipped with a mechanical stirrer, thermometer and reflux condenser is charged with 142 gms. (0.5 mole) aminostearylamine and 13 gms. water. The temperature is raised to 70 C. and acryonitrile (59 gms., 1.11 moles) is added with vigorous stirring over a period of one hour. The temperature is maintained at 70 C. during the addition, then raised to C. for an additional two hours. Excess acrylonitrile and water are removed in vacuo to yield 192.4 gms. (98.7% theory) of di-(B-cyanoethyl) aminostearylamine as a light oil.
- Example II.N,N'-di-(fl-cyanoethyl) aminomethylstearylamine A 250 ml. 3-neck flask equipped with a mechanical stirrer, thermometer, dropping funnel and heating mantle is charged with aminomethylstearylamine (50.0 gms., 0.168 mole; NE, 158.5) and water (4.52 ml., 9% by wt. of amine). The temperature of the reactants is raised to 70 C. and acrylonitrile (19.6 gms., 0.37 mole, 10% excess) added slowly with stirring. The addition is complete in about one hour at 70-80" C. The temperature is then maintained at 7685 C. for an additional two hours. Water and excess acrylonitrile are removedin vacuo to yield 66.5 gms. (97.5% yield) of N,N'-di-( 8-cyanoethyl) aminomethylstearylamine as a pale yellow oil.
- the above dicyanoethylfattyamines may be used to prepare polyamines which possess high surfactant activity.
- aminoor aminoalkylfattyamines that may be reacted with acrylonitrile in accordance with the meth 0d of this invention, those falling within the following formula are operable:
- Such compounds would include the amino-, aminomethyl-, and the aminoethyl-derivatives of fatty amines such as caprylylamine, caprylamine, laurylamine, myristylamine, palrnitylamine, stearylamine, arachidylamine, behenylamine and lignocerylamine or mixtures thereof such as derivatives from natural fats and oils such astallow, soybean oil and coconut oil.
- diamine derivatives of the C to C fatty acids are useful as a reactant.
- dicyanoethylfattydiamines that may be formed by the method of this invention are those which fall within the following formula:
- N,N di (18 cyanoethyl) aminomethylcaprylamine N,N-di-(fl-cyanoethyl) aminomethylundecylamine
- N,N'-di- (fl-cyanoethyl) aminomethylstearylamine N,N di 8- cyanoethyl) aminostearylamine, and the like.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Description
United States Patent ()filice 3,364,248 Patented Jan. 16, 1968 This invention relates to novel derivatives of fatty acid and more particularly to a novel class of dicyanoethylfattydiamines.
It has long been the desire of chemists to synthesize or to extract from natural substances compounds which not only possess the desirable physical and chemical properties of the long chain fatty acids, but also contain two or more reactive groups therein. With two or more reactive groups, the fatty compound would not only have good hydrophobic characteristics, but also have high potency, depending upon its reactive group type for surfactant, for polymeric or for other chemical activity.
Among the approaches made toward accomplishing such an objective, that disclosed in US. 2,813,113 is typical. There the oxidation of oleic acid to azelaic acid [HOOC(CH COOH] is discussed. Unfortunately, chain cleavage occurs in such oxidation. This is undesirable because it cuts down the hydrophobic nature of the resultant compound.
Rowe and Swern of the US. Department of Agriculture, in the Journal of the American Oil Chemists Society periodical, volume 37, pages 661 to 668 (1960) report that unsaturated fatty acids may be carboxylated with carbon monoxide. Such a reaction would conserve the hydrophobic nature of the fatty acid, but apparently no further work was done toward discovering new difunctional fatty compounds. This is unfortunate because, as discussed below, it has been found that such difunctional compounds may be synthesized rather easily and they possess many attributes highly desirable for various chemical technologies.
Accordingly, an object of this invention is to provide novel difunctional fatty compounds which are useful in various chemical technologies.
Another object is to provide a novel class of fatty diamines, more particularly, dicyanoethylfattydiamines.
Still another object is to provide novel methods for the manufacture of such dicyanoethylfattydiamines.
A further object is to provide a novel class of compounds which are excellent intermediates for other tetrafunctional fatty compounds having valuable properties for various chemical technologies.
Other objects of the invention will in part be obvious and will in part appear hereinafter.
The invention accordingly comprises the several steps and the relation of one or more of such steps with respect to each of the others, and the compound possessing the features, properties, and the relation of elements, which are exemplified in the following detailed disclosure, and the scope of the invention will be indicated in the claims.
It has now been found that a novel class of fatty diamines may be prepared by reacting an aminoalkylfattyamine (described more fully in British 920,514 filed June 30, 1959, and British 985,106 filed Ian. 4, 1962) with acrylonitrile. For example, by reacting aminoethylstearylamine with acrylonitrile in the presence of water, N,N-difl-cyanoethyl) aminoethylstearylamine is obtained. Such a compound is useful as an intermediate for forming a di- (aminoalkyl) fatty diamine which is useful as a surfactant, particularly as a flotation agent or an asphalt emulsifier, or as an epoxy curing agent. It also is useful as a bactericide.
Reference is now made to the following examples which illustrate synthesis of specific dicyanoethylfattydiamines:
Example I.-N,N'-ai-(fi-cyanoethyl) aminostearylamine A two-liter four-neck Morton flask equipped with a mechanical stirrer, thermometer and reflux condenser is charged with 142 gms. (0.5 mole) aminostearylamine and 13 gms. water. The temperature is raised to 70 C. and acryonitrile (59 gms., 1.11 moles) is added with vigorous stirring over a period of one hour. The temperature is maintained at 70 C. during the addition, then raised to C. for an additional two hours. Excess acrylonitrile and water are removed in vacuo to yield 192.4 gms. (98.7% theory) of di-(B-cyanoethyl) aminostearylamine as a light oil.
Analysis.-Neut. equivalent, 198.6 (calcd. primary amine, 3.3%; secondary amine, 93.6%; tertiary amine, nil.
Example II.N,N'-di-(fl-cyanoethyl) aminomethylstearylamine A 250 ml. 3-neck flask equipped with a mechanical stirrer, thermometer, dropping funnel and heating mantle is charged with aminomethylstearylamine (50.0 gms., 0.168 mole; NE, 158.5) and water (4.52 ml., 9% by wt. of amine). The temperature of the reactants is raised to 70 C. and acrylonitrile (19.6 gms., 0.37 mole, 10% excess) added slowly with stirring. The addition is complete in about one hour at 70-80" C. The temperature is then maintained at 7685 C. for an additional two hours. Water and excess acrylonitrile are removedin vacuo to yield 66.5 gms. (97.5% yield) of N,N'-di-( 8-cyanoethyl) aminomethylstearylamine as a pale yellow oil.
Analysis.-Neut. equiv, 212 (calc d 202.3); secondary amine 92.2%.
The above dicyanoethylfattyamines may be used to prepare polyamines which possess high surfactant activity.
Among the aminoor aminoalkylfattyamines that may be reacted with acrylonitrile in accordance with the meth 0d of this invention, those falling within the following formula are operable:
FORMULA I CHa(CH,)xCH(CHz)yNH,
where 11:0 to 2, x and y are whole numbers and x+y=6 to 22.
Such compounds would include the amino-, aminomethyl-, and the aminoethyl-derivatives of fatty amines such as caprylylamine, caprylamine, laurylamine, myristylamine, palrnitylamine, stearylamine, arachidylamine, behenylamine and lignocerylamine or mixtures thereof such as derivatives from natural fats and oils such astallow, soybean oil and coconut oil. In general, diamine derivatives of the C to C fatty acids are useful as a reactant.
The dicyanoethylfattydiamines that may be formed by the method of this invention are those which fall within the following formula:
FORMULA II CHz-(CHz) -CH-(CHg) FNHGHRCHKCN (CHzhNHCHaCHzCN where a=0 to 2, x and y are whole numbers and x+y=6 to 22.
Among compounds which fall within the above formula are N,N di (18 cyanoethyl) aminomethylcaprylamine, N,N-di-(fl-cyanoethyl) aminomethylundecylamine, N,N'- di- (3 cyanoethyl)aminomethylpalymitylamine, N,N'-di- (fl-cyanoethyl) aminomethylstearylamine, N,N di 8- cyanoethyl) aminostearylamine, and the like.
It will thus be seen that the objects set forth above, among those made apparent from the preceding description, are efficiently attained and, since certain changes may be made in carrying out the above method and in the compounds set forth Without departing from the scope of the invention, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
It is also to be understood that the following claims are intended to cover all of the generic and specific features of the invention herein described, and all statements of the scope of the invention, which, as a matter of language, might be said to fall therebetween.
Now that the invention has been described, what is claimed as new and desired to be secured by Letters Patent is:
What is claimed is:
l. A dicyanoethylfattydiarnine of the formula:
where (1:0 to 2, x and y are whole numbers and x+y=6 to 22. 2. N,N'-di-(5-eyanoethyl) aminomethylpalmitylarnine falling within the formula:
CHE-(CH2)xCH(CHz)yNHCHzCHzCN CHNHCH2CH;CN
where x+y=16, said x and y being whole numbers.
3. N,N'-di B cyanoethyl) aminomethylstearylamine falling Within the formula:
C H3- CII2 x C H(C 11:) NECHzC H2CN where x+y:16, said x and y being whole numbers.
4. N,N' di (ti-cyanoethyl) aminostearylarnine falling within the formula:
NHCHzCHzCN Where x+y 16, said x and y being whole numbers.
References Cited UNITED JOSEPH P. BRUST, Primary Examiner.
Claims (1)
1. A DICYANOETHYLFATTYDIAMINE OF THE FORMULA:
Priority Applications (4)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US398438A US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
| DE19651493436 DE1493436A1 (en) | 1964-09-22 | 1965-09-17 | Process for the production of dicyanoethyl fatty acid diamines |
| FR32107A FR1447614A (en) | 1964-09-22 | 1965-09-21 | New fatty acid derivatives and process for their preparation |
| GB40434/65A GB1045505A (en) | 1964-09-22 | 1965-09-22 | Dicyanoethyl fatty diamines |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US398438A US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US3364248A true US3364248A (en) | 1968-01-16 |
Family
ID=23575375
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US398438A Expired - Lifetime US3364248A (en) | 1964-09-22 | 1964-09-22 | Novel dicyanoethylfattydiamines of fatty acids |
Country Status (3)
| Country | Link |
|---|---|
| US (1) | US3364248A (en) |
| DE (1) | DE1493436A1 (en) |
| GB (1) | GB1045505A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666788A (en) * | 1969-08-22 | 1972-05-30 | Jefferson Chem Co Inc | Cyanoalkylated polyoxyalkylene polyamines |
| US4180487A (en) * | 1978-05-04 | 1979-12-25 | Henkel Corporation | Epoxy curable resin composition |
| US4257984A (en) * | 1977-04-04 | 1981-03-24 | Henkel Corporation | Monotertiarymonosecondarydiprimarytetramine and monotertiarymonosecondarydinitrilodiamines |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US4271088A (en) | 1978-06-16 | 1981-06-02 | Suntech, Inc. | High selectivity cyanoalkylation process |
Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
| US2448013A (en) * | 1944-12-26 | 1948-08-31 | Upjohn Co | Preparation of beta-aminopropionitrile |
| US2965671A (en) * | 1957-04-22 | 1960-12-20 | Monsanto Chemicals | Process for production of amino compounds |
| US2982781A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and- beta-aminoesters |
| US2982782A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and beta-aminoesters |
| US3158643A (en) * | 1961-05-05 | 1964-11-24 | Gen Mills Inc | Cyanoethylated aminohydroxy amines |
| US3177254A (en) * | 1961-05-23 | 1965-04-06 | Gen Mills Inc | Aminohydroxy amines |
| US3264341A (en) * | 1961-07-03 | 1966-08-02 | Armour & Co | Preparation of dicyanoethylated fatty amines |
-
1964
- 1964-09-22 US US398438A patent/US3364248A/en not_active Expired - Lifetime
-
1965
- 1965-09-17 DE DE19651493436 patent/DE1493436A1/en active Pending
- 1965-09-22 GB GB40434/65A patent/GB1045505A/en not_active Expired
Patent Citations (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1992615A (en) * | 1931-09-10 | 1935-02-26 | Ig Farbenindustrie Ag | Amino nitrile and process of producing same |
| US2448013A (en) * | 1944-12-26 | 1948-08-31 | Upjohn Co | Preparation of beta-aminopropionitrile |
| US2965671A (en) * | 1957-04-22 | 1960-12-20 | Monsanto Chemicals | Process for production of amino compounds |
| US2982781A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and- beta-aminoesters |
| US2982782A (en) * | 1957-08-23 | 1961-05-02 | Monsanto Chemicals | Process for producing beta-aminonitriles and beta-aminoesters |
| US3158643A (en) * | 1961-05-05 | 1964-11-24 | Gen Mills Inc | Cyanoethylated aminohydroxy amines |
| US3177254A (en) * | 1961-05-23 | 1965-04-06 | Gen Mills Inc | Aminohydroxy amines |
| US3264341A (en) * | 1961-07-03 | 1966-08-02 | Armour & Co | Preparation of dicyanoethylated fatty amines |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3666788A (en) * | 1969-08-22 | 1972-05-30 | Jefferson Chem Co Inc | Cyanoalkylated polyoxyalkylene polyamines |
| US4257984A (en) * | 1977-04-04 | 1981-03-24 | Henkel Corporation | Monotertiarymonosecondarydiprimarytetramine and monotertiarymonosecondarydinitrilodiamines |
| US4180487A (en) * | 1978-05-04 | 1979-12-25 | Henkel Corporation | Epoxy curable resin composition |
Also Published As
| Publication number | Publication date |
|---|---|
| DE1493436A1 (en) | 1972-02-24 |
| GB1045505A (en) | 1966-10-12 |
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