US2505931A - Sulfonamide wax emulsions - Google Patents
Sulfonamide wax emulsions Download PDFInfo
- Publication number
- US2505931A US2505931A US10553A US1055348A US2505931A US 2505931 A US2505931 A US 2505931A US 10553 A US10553 A US 10553A US 1055348 A US1055348 A US 1055348A US 2505931 A US2505931 A US 2505931A
- Authority
- US
- United States
- Prior art keywords
- sulfonamide
- emulsion
- wax
- dihydroxyethyl
- emulsions
- Prior art date
- Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
- Expired - Lifetime
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- 239000000839 emulsion Substances 0.000 title claims description 36
- 229940124530 sulfonamide Drugs 0.000 title claims description 7
- 150000003456 sulfonamides Chemical class 0.000 title claims description 5
- 239000003995 emulsifying agent Substances 0.000 claims description 14
- 229910052757 nitrogen Inorganic materials 0.000 claims description 7
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 6
- 239000000194 fatty acid Substances 0.000 claims description 6
- 229930195729 fatty acid Natural products 0.000 claims description 6
- 150000004665 fatty acids Chemical class 0.000 claims description 6
- 239000007764 o/w emulsion Substances 0.000 claims description 6
- 239000001993 wax Substances 0.000 description 28
- -1 p-toluene sulfonamide distearate Chemical compound 0.000 description 16
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 10
- 125000002091 cationic group Chemical group 0.000 description 9
- 239000000203 mixture Substances 0.000 description 8
- VBIIFPGSPJYLRR-UHFFFAOYSA-M Stearyltrimethylammonium chloride Chemical compound [Cl-].CCCCCCCCCCCCCCCCCC[N+](C)(C)C VBIIFPGSPJYLRR-UHFFFAOYSA-M 0.000 description 7
- 239000002253 acid Substances 0.000 description 4
- 125000000129 anionic group Chemical group 0.000 description 4
- 239000000499 gel Substances 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- LRHPLDYGYMQRHN-UHFFFAOYSA-N N-Butanol Chemical compound CCCCO LRHPLDYGYMQRHN-UHFFFAOYSA-N 0.000 description 2
- 235000021355 Stearic acid Nutrition 0.000 description 2
- 125000001931 aliphatic group Chemical group 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 239000004203 carnauba wax Substances 0.000 description 2
- 235000013869 carnauba wax Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- IPCSVZSSVZVIGE-UHFFFAOYSA-N hexadecanoic acid Chemical compound CCCCCCCCCCCCCCCC(O)=O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 2
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 2
- KJIFKLIQANRMOU-UHFFFAOYSA-N oxidanium;4-methylbenzenesulfonate Chemical compound O.CC1=CC=C(S(O)(=O)=O)C=C1 KJIFKLIQANRMOU-UHFFFAOYSA-N 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000008117 stearic acid Substances 0.000 description 2
- 230000008719 thickening Effects 0.000 description 2
- HHHDJHHNEURCNV-UHFFFAOYSA-N 4-chlorobenzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=C(Cl)C=C1 HHHDJHHNEURCNV-UHFFFAOYSA-N 0.000 description 1
- KHBQMWCZKVMBLN-UHFFFAOYSA-N Benzenesulfonamide Chemical compound NS(=O)(=O)C1=CC=CC=C1 KHBQMWCZKVMBLN-UHFFFAOYSA-N 0.000 description 1
- 235000010919 Copernicia prunifera Nutrition 0.000 description 1
- 244000180278 Copernicia prunifera Species 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 235000021314 Palmitic acid Nutrition 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical group C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000007605 air drying Methods 0.000 description 1
- 125000004421 aryl sulphonamide group Chemical group 0.000 description 1
- CJZGTCYPCWQAJB-UHFFFAOYSA-L calcium stearate Chemical class [Ca+2].CCCCCCCCCCCCCCCCCC([O-])=O.CCCCCCCCCCCCCCCCCC([O-])=O CJZGTCYPCWQAJB-UHFFFAOYSA-L 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 239000013078 crystal Substances 0.000 description 1
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 239000012456 homogeneous solution Substances 0.000 description 1
- 239000000463 material Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 239000012452 mother liquor Substances 0.000 description 1
- WQEPLUUGTLDZJY-UHFFFAOYSA-N n-Pentadecanoic acid Natural products CCCCCCCCCCCCCCC(O)=O WQEPLUUGTLDZJY-UHFFFAOYSA-N 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 150000003242 quaternary ammonium salts Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000003441 saturated fatty acids Nutrition 0.000 description 1
- 150000004671 saturated fatty acids Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- LMYRWZFENFIFIT-UHFFFAOYSA-N toluene-4-sulfonamide Chemical compound CC1=CC=C(S(N)(=O)=O)C=C1 LMYRWZFENFIFIT-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
- C08L91/06—Waxes
-
- 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
- C09K23/18—Quaternary ammonium compounds
Definitions
- the present invention relates to sulfonamide wax emulsions and to a method of preparing them.
- Wax emulsions commonly in use today generally contain carnauba wax. These compositions are composed of oil-in-water type emulsions containing some anionic emulsifying agent. It is important that the emulsion be of the oil-inwater type inasmuch as in this form it is possible for the emulsion to be thinned by the addition of further quantities of water. When these emulsions are in the reverse form, namely a water-inoil type, they form gels which cannot be thinned with water inasmuch as the gels merely absorb further quantities of water.
- the waxes which may be employed in the present invention are N,N-dihydroxyethyl aryl sulfonamide diesters of higher fatty acids, preferably saturated higher fatty acids.
- Typical of these waxes are the higher saturated fatty acid esters of N,N-dihydroxyethyl benzene sulfonamide, N,N-dihydroxyethyl p-toluene sulfonamide, N,N-dihydroxyethyl p-chlorbenzene sulfonamide, and the like.
- the esters the stearates are preferred inasmuch as these are waxes of high melting point.
- stearic acid For esterification commercial stearic acid may be employed or any mixed steal-1c acid containing not more than about unsaturated acids. It is also possible to produce desirable waxes from other saturated fatty acids such as palmitic acid or from any saturated acid containing 12 or more, carbon atoms. These waxes may be prepared in accordance with the teaching of my copending application, Serial No. 643,748, filed January26, 1946 (now Patent No. 2,496,650), entitled Esters of hydroxyalkyl aromatic sulfonamides.
- the cationic emulsifying agents may be of various types. It is preferred to employ quaternary ammonium salts having the following general formula:
- R is a long chain aliphatic group containing from 12-24 carbon atoms
- R ll. and B may represent alike or diflerent low aliphatic groups, such as methyl, ethyl, etc. Similar com pounds in which the nitrogen has attached to it the residue ofa pyridine ring in place of the groups R R and ll. may be used.
- Typical of the cationic emulsifying agents which are suitable for this purpose is octadecyl trimethyl ammonium chloride. Numerous other compounds of this type which meet the above formula may be used for this purpose.
- Other cationic emulsifying agents which are suitable include 1-hydroxyethyl-2-heptadeceny1 glyoxalldlne.
- Example 1 210 g. diethanolamine were dissolved in 700 cc.
- Example 2 A wax emulsion was prepared in exactly the same manner as Example 1, employing N,N-dihydroxyethyl benzene sulfonamide distearate. The product was found to be a desirable wax emulsion.
- Example 3 A wax emulsion was prepared in exactly the same manner as Example 1, except that N,N-dihydroxyethyl p-chlorbenzene sulfonamide distearate was employed. The product obtained was a desirable Wax emulsion.
- Example 4 A wax emulsion was prepared in exactly the same manner as Example 1, except that l-hydroxyethyl-2-heptadecenyl glyoxalidine was employed. The product obtained was a desirable wax emulsion.
- emulsion compositions of the present invention are stable oil-in-water emulsions of novel wax compositions and render them suitable for use in this form.
- An oil-,in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing a cationic emulsifying agent.
- An oil-inwater emulsion of a synthetic wax comprising NN-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing a cationic emulsifying agent having the following formula in which R is a long chain aliphatic radical containing from 12-24 carbon atoms, and R, R and R represent low aliphatic radicals.
- An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing octadecyl trimethyl ammonium chloride.
- An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl benzene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
- An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl p-toluene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
- An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxymethyl p-chlorbenzene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
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- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Colloid Chemistry (AREA)
Description
Patented May 2, 1950 SULFONAMIDE WAX EMULSIONS David Aelony, Minneapolis, Minn., assignor to General Mills, Inc., a corporation of Delaware No Drawing. Application February 24, 1948, Serial No. 1|,553
7 Claims. (Cl. 106-287) 1 The present invention relates to sulfonamide wax emulsions and to a method of preparing them.
Wax emulsions commonly in use today generally contain carnauba wax. These compositions are composed of oil-in-water type emulsions containing some anionic emulsifying agent. It is important that the emulsion be of the oil-inwater type inasmuch as in this form it is possible for the emulsion to be thinned by the addition of further quantities of water. When these emulsions are in the reverse form, namely a water-inoil type, they form gels which cannot be thinned with water inasmuch as the gels merely absorb further quantities of water. It has been found that emulsions of carnauba wax prepared with cationic emulsifying agents such as octadecyl trimethyl ammonium chloride, formed water-in-oil type emulsionswhich gelled on standing, thereby rendering them unsuitable for use as emulsions.
In preparing emulsions of wax of the type herein described, such as N,N-dihydroxyethyl p-toluene sulfonamide distearate, it was found that the emulsions prepared with anionic emulsifying agents gelled on standing for relatively short periods of time. Such compositions were useless where the employment of an emulsion was desirable. This was found to be true after numerous attempts with a wide variety of anionic emulsifying agents.
It has now been found that excellent emulsions of sulfonamide ester waxes of p the type above mentioned can be prepared by the use of cationic emulsifying agents. Some of these have been in storage for more than eight months and have exhibited no tendency toward thickening.
It is, therefore, an object of the present invention to provide oil-in-water emulsions of aryl sulfonamide ester waxes of the above type employing cationic emulsifying agents, which emulsions do not have a tendency to gel upon standing for extended periods of time.
The waxes which may be employed in the present invention are N,N-dihydroxyethyl aryl sulfonamide diesters of higher fatty acids, preferably saturated higher fatty acids. Typical of these waxes are the higher saturated fatty acid esters of N,N-dihydroxyethyl benzene sulfonamide, N,N-dihydroxyethyl p-toluene sulfonamide, N,N-dihydroxyethyl p-chlorbenzene sulfonamide, and the like. Of the esters, the stearates are preferred inasmuch as these are waxes of high melting point. For esterification commercial stearic acid may be employed or any mixed steal-1c acid containing not more than about unsaturated acids. It is also possible to produce desirable waxes from other saturated fatty acids such as palmitic acid or from any saturated acid containing 12 or more, carbon atoms. These waxes may be prepared in accordance with the teaching of my copending application, Serial No. 643,748, filed January26, 1946 (now Patent No. 2,496,650), entitled Esters of hydroxyalkyl aromatic sulfonamides.
The cationic emulsifying agents may be of various types. It is preferred to employ quaternary ammonium salts having the following general formula:
BALM- in which R is a long chain aliphatic group containing from 12-24 carbon atoms, and R ll. and B may represent alike or diflerent low aliphatic groups, such as methyl, ethyl, etc. Similar com pounds in which the nitrogen has attached to it the residue ofa pyridine ring in place of the groups R R and ll. may be used. Typical of the cationic emulsifying agents which are suitable for this purpose is octadecyl trimethyl ammonium chloride. Numerous other compounds of this type which meet the above formula may be used for this purpose. Other cationic emulsifying agents which are suitable include 1-hydroxyethyl-2-heptadeceny1 glyoxalldlne.
The following examples will serve to illustrate the invention:
1 Example 1 210 g. diethanolamine were dissolved in 700 cc.
water and the mixture was heated to C. 190.5 g. p-toluene sulfonchloride were added at once. A violent reaction accompanied by boiling took place, and a homogeneous solution resulted. On cooling, .2. dark lower layer separated which solidified at 45 C. It was filtered and recrystallized from methanol yielding 156 g. white crystals M. P. 101.5-103.5 C. and 42 g. white powder (from mother liquor) M. P. 97.5- G. The total yield was 76.5 theory.
129.5 g. N,N-di-beta-hydroxyethyl p-toluene sulfonamide, 280.5 g. of a commercial stearic acid (Neo Fat 1-65) l g. p-toluene sulfonic acid monohydrate and 250 cc. xylene were refluxed over a Stark and Dean tube for two hours. A total of 18 cc. of water was collected in the trap. The prodnot was poured into 1.5 liters butanol, was allowed to stand overnight and filtered. After flve days of air drying 353.5 g. of the product (92% yield) M. P. 68.569.5 C. were obtained. Percent N found 1.765 (theory for the stearate, 1.78) acid number 2.4. When melted and allowed to solidify a beautiful hard shiny solid is formed (penetration in 30 sec. with a 200 g. load, ASTM needle, was 3, while it was 1 for carnauba No. 1).
3 g. of octadecyl trimethyl ammonium chloride were dissolved in 183 cc. of boiling water and agitated with 14 g. of N,N-dihydrxyethyl ptoluene sulfonamide distearate. The mixture was put through a hand homogenizer twice and was then allowed to cool. Upon storage for eight months the emulsion showed no sign of thickening.
Example 2 A wax emulsion was prepared in exactly the same manner as Example 1, employing N,N-dihydroxyethyl benzene sulfonamide distearate. The product was found to be a desirable wax emulsion.
Example 3 A wax emulsion was prepared in exactly the same manner as Example 1, except that N,N-dihydroxyethyl p-chlorbenzene sulfonamide distearate was employed. The product obtained was a desirable Wax emulsion.
Example 4 A wax emulsion was prepared in exactly the same manner as Example 1, except that l-hydroxyethyl-2-heptadecenyl glyoxalidine was employed. The product obtained was a desirable wax emulsion.
In contrast to these examples, numerous examples were performed employing anionic emulsifying agents, and it was found that they either did not emulsify the wax at all, or emulsified it very poorly, or formed a gel. All such compositions were unsuitable for the purpose for which a wax emulsion is intended.
It will be apparent, therefore, that the emulsion compositions of the present invention are stable oil-in-water emulsions of novel wax compositions and render them suitable for use in this form.
While various modifications of the invention have been described, it will be apparent that others are possible without departing from the spirit of the invention. Thus it will be apparent that numerous wax compounds coming within applicant's general formula may be employed.
portions. It is likewise apparent that addltimal materials may be included in the composition. It is to be understood, therefore, that the invention is not limited to such specific embodiments. but may be varied within the scope of the following claims.
I claim as my invention:
1. An oil-,in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing a cationic emulsifying agent.
2. An oil-inwater emulsion of a synthetic wax comprising NN-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing a cationic emulsifying agent having the following formula in which R is a long chain aliphatic radical containing from 12-24 carbon atoms, and R, R and R represent low aliphatic radicals.
3. An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl aryl sulfonamide diester of a higher fatty acid, said emulsion containing octadecyl trimethyl ammonium chloride.
4. An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl aryl sulfonamide distearate, said emulsion containing a cationic emulsifying agent.
5. An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl benzene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
6. An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxyethyl p-toluene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
7. An oil-in-water emulsion of a synthetic wax comprising N,N-dihydroxymethyl p-chlorbenzene sulfonamide distearate, said emulsion containing octadecyl trimethyl ammonium chloride.
DAVID AELONY.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS
Claims (1)
1. AN OIL-IN-WATER EMULSION OF A SYNTHETIC WAX COMPRISING N,N-DIHYDROXYETHYL ARYL SULFONAMIDE DIESTER OF A HIGHER FATTY ACID, SAID EMULSION CONTAINING A CATIONIC EMULSIFYING AGENT.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10553A US2505931A (en) | 1948-02-24 | 1948-02-24 | Sulfonamide wax emulsions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US10553A US2505931A (en) | 1948-02-24 | 1948-02-24 | Sulfonamide wax emulsions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2505931A true US2505931A (en) | 1950-05-02 |
Family
ID=21746291
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US10553A Expired - Lifetime US2505931A (en) | 1948-02-24 | 1948-02-24 | Sulfonamide wax emulsions |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2505931A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213173A (en) * | 1958-03-17 | 1965-10-19 | Phillips Petroleum Co | Method of potting and bonding |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2277788A (en) * | 1940-08-03 | 1942-03-31 | Du Pont | Treatment of textiles and composition useful therefor |
| US2292464A (en) * | 1939-05-23 | 1942-08-11 | Celanese Corp | Nu-hydroxyalkyl nu-aryl sulphonamides and their derivatives |
| US2305083A (en) * | 1940-03-22 | 1942-12-15 | American Cyanamid Co | Amino alcohol esters |
| US2353694A (en) * | 1942-05-25 | 1944-07-18 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2398295A (en) * | 1943-03-13 | 1946-04-09 | Emulsol Corp | Emulsions |
-
1948
- 1948-02-24 US US10553A patent/US2505931A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2292464A (en) * | 1939-05-23 | 1942-08-11 | Celanese Corp | Nu-hydroxyalkyl nu-aryl sulphonamides and their derivatives |
| US2305083A (en) * | 1940-03-22 | 1942-12-15 | American Cyanamid Co | Amino alcohol esters |
| US2277788A (en) * | 1940-08-03 | 1942-03-31 | Du Pont | Treatment of textiles and composition useful therefor |
| US2353694A (en) * | 1942-05-25 | 1944-07-18 | Petrolite Corp | Process for breaking petroleum emulsions |
| US2398295A (en) * | 1943-03-13 | 1946-04-09 | Emulsol Corp | Emulsions |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3213173A (en) * | 1958-03-17 | 1965-10-19 | Phillips Petroleum Co | Method of potting and bonding |
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