US2724694A - Mineral oils containing alkoxyalkylolamine epichlorhydrin condensation products - Google Patents
Mineral oils containing alkoxyalkylolamine epichlorhydrin condensation products Download PDFInfo
- Publication number
- US2724694A US2724694A US251837A US25183751A US2724694A US 2724694 A US2724694 A US 2724694A US 251837 A US251837 A US 251837A US 25183751 A US25183751 A US 25183751A US 2724694 A US2724694 A US 2724694A
- Authority
- US
- United States
- Prior art keywords
- epichlorhydrin
- mol
- mols
- alkoxyalkylolamine
- condensation products
- 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
- 239000007859 condensation product Substances 0.000 title claims description 15
- 239000002480 mineral oil Substances 0.000 title claims description 15
- BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 title claims description 13
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 claims description 12
- 239000000203 mixture Substances 0.000 claims description 10
- 235000010446 mineral oil Nutrition 0.000 claims description 9
- 238000010438 heat treatment Methods 0.000 claims description 5
- 239000007795 chemical reaction product Substances 0.000 claims description 3
- 150000003973 alkyl amines Chemical class 0.000 claims description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims 1
- 239000003921 oil Substances 0.000 description 19
- 239000003995 emulsifying agent Substances 0.000 description 9
- 239000000047 product Substances 0.000 description 7
- REYJJPSVUYRZGE-UHFFFAOYSA-N Octadecylamine Chemical compound CCCCCCCCCCCCCCCCCCN REYJJPSVUYRZGE-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 6
- 239000000839 emulsion Substances 0.000 description 6
- 229930195733 hydrocarbon Natural products 0.000 description 5
- 150000002430 hydrocarbons Chemical class 0.000 description 5
- 239000004215 Carbon black (E152) Substances 0.000 description 4
- 230000001804 emulsifying effect Effects 0.000 description 4
- -1 aliphatic amines Chemical class 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 238000009833 condensation Methods 0.000 description 3
- 230000005494 condensation Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- 229920000742 Cotton Polymers 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 description 2
- BTANRVKWQNVYAZ-UHFFFAOYSA-N butan-2-ol Chemical compound CCC(C)O BTANRVKWQNVYAZ-UHFFFAOYSA-N 0.000 description 2
- 125000002091 cationic group Chemical group 0.000 description 2
- 239000000835 fiber Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- VVXPDWRMIXEULT-UHFFFAOYSA-N octadecan-1-amine;oxirane Chemical compound C1CO1.CCCCCCCCCCCCCCCCCCN VVXPDWRMIXEULT-UHFFFAOYSA-N 0.000 description 2
- 238000002360 preparation method Methods 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- XZMCDFZZKTWFGF-UHFFFAOYSA-N Cyanamide Chemical compound NC#N XZMCDFZZKTWFGF-UHFFFAOYSA-N 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 239000007900 aqueous suspension Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 239000008278 cosmetic cream Substances 0.000 description 1
- 238000007865 diluting Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 239000004744 fabric Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 229940097789 heavy mineral oil Drugs 0.000 description 1
- 230000001771 impaired effect Effects 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 239000000314 lubricant Substances 0.000 description 1
- 239000002798 polar solvent Substances 0.000 description 1
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 230000002269 spontaneous effect Effects 0.000 description 1
- 239000007858 starting material Substances 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M1/00—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants
- C10M1/08—Liquid compositions essentially based on mineral lubricating oils or fatty oils; Their use as lubricants with additives
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
-
- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
- C09K23/42—Ethers, e.g. polyglycol ethers of alcohols or phenols
- C09K23/46—Ethers of aminoalcohols
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2201/00—Inorganic compounds or elements as ingredients in lubricant compositions
- C10M2201/02—Water
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10M—LUBRICATING COMPOSITIONS; USE OF CHEMICAL SUBSTANCES EITHER ALONE OR AS LUBRICATING INGREDIENTS IN A LUBRICATING COMPOSITION
- C10M2215/00—Organic non-macromolecular compounds containing nitrogen as ingredients in lubricant compositions
- C10M2215/02—Amines, e.g. polyalkylene polyamines; Quaternary amines
- C10M2215/04—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms
- C10M2215/042—Amines, e.g. polyalkylene polyamines; Quaternary amines having amino groups bound to acyclic or cycloaliphatic carbon atoms containing hydroxy groups; Alkoxylated derivatives thereof
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10N—INDEXING SCHEME ASSOCIATED WITH SUBCLASS C10M RELATING TO LUBRICATING COMPOSITIONS
- C10N2040/00—Specified use or application for which the lubricating composition is intended
- C10N2040/46—Textile oils
-
- 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
- self-emulsifying mineral oils are obtained by incorporating therein emulsifying quantities of a particular class of cationic emulsifying agents.
- These new emulsifying agents are prepared from higher aliphatic amines of 12-18 carbon atoms that have been reacted with ethylene oxide or propylene oxide, such as the ethoxyethylolamines obtained by condensing 1 mol of the higher aliphatic amines with from 2 to about 10 mols of ethylene oxide.
- condensation products have previously been suggested as emulsifying agents for mineral oils.
- Self-emulsifiable mineral oils are in Wide commercial use in the manufacture of products composed of or containing felted cellulose fibers, as Well as for textile softeners, textile lubricants and the like.
- the condensation products of the present invention possess all the advantageous properties of a highly eflicient oil-soluble cationic emulsifying agent including the production of aqueous emulsions of oil droplets which exhaust or absorb on cellulosic fibers in water suspension.
- the emulsified oils can therefore be applied to cellulosic paper fibers, in the beater or elsewhere in the stock system, ,before they are formed into paper; the emulsions can also 2,724,694 Patented Nov. 22, 1955 be applied to cotton threads, cotton cloth and to other cellulosic textiles.
- octadecylamine is the preferred starting material.
- O'ctadecylamines are available commercially in several grades and any of these may be employed; their usefulness is not materially impaired by the presence of a small proportion of unsaturated amine.
- the condensation of ethylene oxide or propylene oxide with the amine is carried out most advantageously by diluting the amine with a polar solvent such as a propyl or butyl alcohol and passing in the alkylene oxide at atmospheric or slightly elevated pressures while maintaining the reaction mixture at the boiling point of the alcohol until the desired quantity has been chemically combined.
- the condensation between the alkoxyalkylolamine and epichlorhydrin is carried out simply by heating the two ingredients together in the desired molar ratio.
- Theoretically one mol of epichlorhydrin can be reacted with one mol of amine; however, reaction products of from 0.05 to 0.5 mols of epichlorhydrin for each mol of amine are employed as those containing a larger proportion of combined epichlorhydrin have only a low solubility in hydrocarbon oils.
- reaction products of from 0.05 to 0.5 mols of epichlorhydrin for each mol of amine are employed as those containing a larger proportion of combined epichlorhydrin have only a low solubility in hydrocarbon oils.
- Usually a satisfactory degree of condensation is obtained by heating the reagents together at about 6080 C. for about 0.5 to 2 hours.
- the condensation product is soluble in xylene, in paraffinic hydrocarbon oils, and in other hydrocarbons, and can be used as a solution in any of
- the quantity of condensation product to be dissolved in mineral oil for the preparation of self-emulsifiable oil compositions will depend on the particular properties desired in the oil. As little as about 2.5%, based on the weight of the oil, is sulficient to produce an oil composition that will form a stable emulsion in water; however, for most purposes quantities of 5-1-0% are preferable. From this range the amount of condensation product may increase to as much as 3040% by weight of the oil-alkoxyalkylolamine-epichlorhydrin condensation product composition, particularly where the oils are used to obtain improved softness and absorbency in paper.
- a self-emulsifying mineral oil composition comprising mineral oil having dissolved therein emulsifying quantities, not less than 2.5% by weight, of the condensation product of 0.05 to 0.5 mols of epichlorhydrin with one mol of an ethoxyethyloloctadecylamine containing from 2 to 10 mols of combined ethylene oxide for each mol of octadecylamine.
- 19 A composition according to claim 2 in which the 10% Emulsion 5% Emulsion 24 Hrs.
- a self-emulsifying mineral oil composition comprising mineral oil having dissolved therein a minor quantity not less than 2.5% by weight of the reaction product obtained by heating 0.05 to 0.5 mols of epichlorhydrin with the condensation product of 1 mol of a primary alkylamine ethoxyethyloloctadecylamine contains from 2 to 6 mols of combined ethylene oxide for each mol of octadecylamine.
- a self-emulsifying mineral oil composition comprising mineral oil having dissolved therein emulsifying quantities, not less than 2.5% by weight, of the condensation product of from 0.1 to 0.2 mols of epichlorhydrin with 1 mol of an ethoxyethyloloctadecylamine containing from 2 to 10 mols of combined ethylene oxide for each mol of octadecylamine.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
- Colloid Chemistry (AREA)
- Macromolecular Compounds Obtained By Forming Nitrogen-Containing Linkages In General (AREA)
Description
NHNERAL OILS CONTAENING ALKOXYALKYLOL- AMINE EPICHLO i3 CUNDENSATIQN PRODUCTS Emilio J. Troianello, Stamford, Conn., assignor to American Cyanamid Company, New York, N. $1., a corporation of Maine No Drawing. Application ()ctober 1'7, 1951, Serial No. 251,837
4 Claims. (Cl. 2523.8)
seconds at 100 F, are ernulsified in water and used for the oiling of acetate or cuprammonium rayon, and also for natural silk. Somewhat heavier oils, having viscosities within the range of 90-150 seconds, are used in the preparation of cosmetic creams. Still heavier refined White oils, with viscosities as high as 350 'seconds'or more, are used in emulsified form for a number of purposes including internal medicinal uses. Any of these mineral oils can be made self-emulsifiable in water by dissolving therein the novel emulsifying agents of the present inventron.
In accordance with my present invention, self-emulsifying mineral oils are obtained by incorporating therein emulsifying quantities of a particular class of cationic emulsifying agents. These new emulsifying agents are prepared from higher aliphatic amines of 12-18 carbon atoms that have been reacted with ethylene oxide or propylene oxide, such as the ethoxyethylolamines obtained by condensing 1 mol of the higher aliphatic amines with from 2 to about 10 mols of ethylene oxide. Such condensation products have previously been suggested as emulsifying agents for mineral oils.
I have found that much better emulsifying properties for hydrocarbon oils are imparted to the amine-alkylene oxide condensation products when these products are condensed with small amounts of epichlorohydrin. Thus, for example, by reacting 1 mol of octadecylamine-ethylene oxide condensation products containing from 2 to about 10 mols of combined ethylene oxide with from 0.05 to 0.5 mols of epichlorhydrin, an excellent class of spontaneous emulsifiers is obtained for parafiinic hydrocarbon oils having viscosities of 80 seconds at 100 F. The ordinary octadecylamine ethylene oxide condensation products are not good emulsifying agents for this particular type of oil.
The commercial importance of my discovery is evident. Self-emulsifiable mineral oils are in Wide commercial use in the manufacture of products composed of or containing felted cellulose fibers, as Well as for textile softeners, textile lubricants and the like. When used for these purposes the condensation products of the present invention possess all the advantageous properties of a highly eflicient oil-soluble cationic emulsifying agent including the production of aqueous emulsions of oil droplets which exhaust or absorb on cellulosic fibers in water suspension. The emulsified oils can therefore be applied to cellulosic paper fibers, in the beater or elsewhere in the stock system, ,before they are formed into paper; the emulsions can also 2,724,694 Patented Nov. 22, 1955 be applied to cotton threads, cotton cloth and to other cellulosic textiles.
Although any aliphatic primary amine of 12 to 18 carbon atoms may be used, octadecylamine is the preferred starting material. O'ctadecylamines are available commercially in several grades and any of these may be employed; their usefulness is not materially impaired by the presence of a small proportion of unsaturated amine. The condensation of ethylene oxide or propylene oxide with the amine is carried out most advantageously by diluting the amine with a polar solvent such as a propyl or butyl alcohol and passing in the alkylene oxide at atmospheric or slightly elevated pressures while maintaining the reaction mixture at the boiling point of the alcohol until the desired quantity has been chemically combined.
The condensation between the alkoxyalkylolamine and epichlorhydrin is carried out simply by heating the two ingredients together in the desired molar ratio. Theoretically one mol of epichlorhydrin can be reacted with one mol of amine; however, reaction products of from 0.05 to 0.5 mols of epichlorhydrin for each mol of amine are employed as those containing a larger proportion of combined epichlorhydrin have only a low solubility in hydrocarbon oils. Usually a satisfactory degree of condensation is obtained by heating the reagents together at about 6080 C. for about 0.5 to 2 hours. The condensation product is soluble in xylene, in paraffinic hydrocarbon oils, and in other hydrocarbons, and can be used as a solution in any of these solvents.
The quantity of condensation product to be dissolved in mineral oil for the preparation of self-emulsifiable oil compositions will depend on the particular properties desired in the oil. As little as about 2.5%, based on the weight of the oil, is sulficient to produce an oil composition that will form a stable emulsion in water; however, for most purposes quantities of 5-1-0% are preferable. From this range the amount of condensation product may increase to as much as 3040% by weight of the oil-alkoxyalkylolamine-epichlorhydrin condensation product composition, particularly where the oils are used to obtain improved softness and absorbency in paper.
The invention will be further illustrated by the following specific example. It should be understood, however, that While this example may describe in detail certain specific features of the invention, it is given also for illustration and the invention in its broader aspects is not limited thereto.
Example A mixture of 61.7 lbs. of a commercial octadecylamine and 7.4 gallons of sec-butyl alcohol was charged to a glass lined kettle equipped with a brine-cooled condenser. These materials were heated to about 90 C. and ethylene oxide gas was passed into the kettle. After the reaction had started the materials were cooled so that the temperature was maintained at from C.-l00 C. After 11.5 hours the temperature of the reaction mixture was maintained at from C.l00 C. for an additional 2 hours to insure complete reaction of the ethylene oxide. Thereafter the product was stripped of solvent and volatile materials by heating to C. under a vacuum of 20-30 mm. Hg. The product contained 3.7 mols of combined ethylene oxide for each mol of octadecylamine and was an orange-brown liquid at room temperature; it contained 96.3% of active material.
To portions of the condensation product weighing 480 grams (1 mol) there were added quantities of epichlorhydrin varying from 4.63 grams (0.05 mol) to 46.25 grams (0.5 mol) and the mixtures were heated on an oil bath for 1 hour. The resulting products were limpid, slightly viscous red-brown liquids that were soluble in mineral oils.
These products were dissolved in a heavy mineral oil of 12-18 carbon atoms with 2 to 10 mols of combined ethylene oxide.
2. A self-emulsifying mineral oil composition comprising mineral oil having dissolved therein emulsifying quantities, not less than 2.5% by weight, of the condensation product of 0.05 to 0.5 mols of epichlorhydrin with one mol of an ethoxyethyloloctadecylamine containing from 2 to 10 mols of combined ethylene oxide for each mol of octadecylamine. 19 3. A composition according to claim 2 in which the 10% Emulsion 5% Emulsion 24 Hrs.
No Ratio Fresh 24 Hrs. Fresh Thick Fair do .d
Excellent, Thin Goog, Thin.
Very Good o Thin, Frothy. Slightly Creaming. do do Slightly Gelatinous.
6-7 cc. creamed;
no tree oil.
These results show that, while self-emulsification is obtained throughout the range of 0.05-0.5 mols of epichlorhydrin per mol of amine, the optimum ratio is about 0.1 to 0.2 mol. Similar tests using 2.5% of the emulsifiers and of the oil solution in the emulsions showed similar results. Larger quantities of the emulsifier up to, for example, -30% on the weight of the oil can of course be used if desired, but for most purposes this is not necessary.
What I claim is:
l. A self-emulsifying mineral oil composition comprising mineral oil having dissolved therein a minor quantity not less than 2.5% by weight of the reaction product obtained by heating 0.05 to 0.5 mols of epichlorhydrin with the condensation product of 1 mol of a primary alkylamine ethoxyethyloloctadecylamine contains from 2 to 6 mols of combined ethylene oxide for each mol of octadecylamine.
4. A self-emulsifying mineral oil composition comprising mineral oil having dissolved therein emulsifying quantities, not less than 2.5% by weight, of the condensation product of from 0.1 to 0.2 mols of epichlorhydrin with 1 mol of an ethoxyethyloloctadecylamine containing from 2 to 10 mols of combined ethylene oxide for each mol of octadecylamine.
Schoeller et a1 Aug. 21, 1934 Schuette Oct. 3, 1939
Claims (1)
1. A SELF-EMULSIFYING MINERAL OIL COMPOSITION COMPRISING MINERAL OIL HAVING DISSOLVED THEREIN A MINOR QUANTITY NOT LESS THAN 2.5% BY WEIGHT OF THE REACTION PRODUCT OBTAINED BY HEATING 0.05 TO 0.5 MOLS OF EPICHLORHYDRIN WITH THE CONDENSATION PRODUCT OF 1 MOL OF A PRIMARY ALKYLAMINE OF 12-18 CARBON ATOMS WITH 2 TO 10 MOLS OF COMBINED ETHYLENE OXIDE.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US251837A US2724694A (en) | 1951-10-17 | 1951-10-17 | Mineral oils containing alkoxyalkylolamine epichlorhydrin condensation products |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US251837A US2724694A (en) | 1951-10-17 | 1951-10-17 | Mineral oils containing alkoxyalkylolamine epichlorhydrin condensation products |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2724694A true US2724694A (en) | 1955-11-22 |
Family
ID=22953620
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US251837A Expired - Lifetime US2724694A (en) | 1951-10-17 | 1951-10-17 | Mineral oils containing alkoxyalkylolamine epichlorhydrin condensation products |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2724694A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956889A (en) * | 1956-02-06 | 1960-10-18 | Dearborn Chemicals Co | Corrosion inhibition |
| US3017258A (en) * | 1957-03-20 | 1962-01-16 | Universal Oil Prod Co | Stabilization of burner oil |
| US3017343A (en) * | 1958-04-28 | 1962-01-16 | Universal Oil Prod Co | Preventing heat exchange deposits |
| US3206410A (en) * | 1957-06-12 | 1965-09-14 | Scholten Chemische Fab | Water-in-oil emulsions |
| US3240721A (en) * | 1960-06-30 | 1966-03-15 | Rohm & Haas | Alkylene oxide adducts of polyalkylene- polyamine-epihalohydrin condensation products |
| DE1292572B (en) * | 1964-05-11 | 1969-04-10 | Armour & Co | Neutral or slightly acidic, aqueous bituminous emulsions for road construction |
| US4374031A (en) * | 1980-06-06 | 1983-02-15 | Unitika Limited | Method for manufacturing polyester fibers with good adhesion to rubber |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2174762A (en) * | 1935-04-13 | 1939-10-03 | Ig Farbenindustrie Ag | Condensation products derived from amines and method of producing them |
-
1951
- 1951-10-17 US US251837A patent/US2724694A/en not_active Expired - Lifetime
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1970578A (en) * | 1930-11-29 | 1934-08-21 | Ig Farbenindustrie Ag | Assistants for the textile and related industries |
| US2174762A (en) * | 1935-04-13 | 1939-10-03 | Ig Farbenindustrie Ag | Condensation products derived from amines and method of producing them |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2956889A (en) * | 1956-02-06 | 1960-10-18 | Dearborn Chemicals Co | Corrosion inhibition |
| US3017258A (en) * | 1957-03-20 | 1962-01-16 | Universal Oil Prod Co | Stabilization of burner oil |
| US3206410A (en) * | 1957-06-12 | 1965-09-14 | Scholten Chemische Fab | Water-in-oil emulsions |
| US3017343A (en) * | 1958-04-28 | 1962-01-16 | Universal Oil Prod Co | Preventing heat exchange deposits |
| US3240721A (en) * | 1960-06-30 | 1966-03-15 | Rohm & Haas | Alkylene oxide adducts of polyalkylene- polyamine-epihalohydrin condensation products |
| DE1292572B (en) * | 1964-05-11 | 1969-04-10 | Armour & Co | Neutral or slightly acidic, aqueous bituminous emulsions for road construction |
| US4374031A (en) * | 1980-06-06 | 1983-02-15 | Unitika Limited | Method for manufacturing polyester fibers with good adhesion to rubber |
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