US2651645A - Surface active agents - Google Patents
Surface active agents Download PDFInfo
- Publication number
- US2651645A US2651645A US32039A US3203948A US2651645A US 2651645 A US2651645 A US 2651645A US 32039 A US32039 A US 32039A US 3203948 A US3203948 A US 3203948A US 2651645 A US2651645 A US 2651645A
- Authority
- US
- United States
- Prior art keywords
- compounds
- taurate
- carbon atoms
- active agents
- surface active
- 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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- 239000004094 surface-active agent Substances 0.000 title description 4
- 150000001875 compounds Chemical class 0.000 claims description 19
- 125000004432 carbon atom Chemical group C* 0.000 description 11
- 229940104261 taurate Drugs 0.000 description 11
- 230000000694 effects Effects 0.000 description 7
- -1 iso-octyl Chemical group 0.000 description 7
- XOAAWQZATWQOTB-UHFFFAOYSA-N taurine Chemical class NCCS(O)(=O)=O XOAAWQZATWQOTB-UHFFFAOYSA-N 0.000 description 7
- 238000009736 wetting Methods 0.000 description 7
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
- 239000000203 mixture Substances 0.000 description 6
- 125000002252 acyl group Chemical group 0.000 description 5
- KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
- 229910052783 alkali metal Chemical group 0.000 description 3
- 229910052739 hydrogen Inorganic materials 0.000 description 3
- 239000001257 hydrogen Substances 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 125000000740 n-pentyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 3
- 159000000000 sodium salts Chemical class 0.000 description 3
- 229960003080 taurine Drugs 0.000 description 3
- 239000000080 wetting agent Substances 0.000 description 3
- QGZKDVFQNNGYKY-UHFFFAOYSA-O Ammonium Chemical group [NH4+] QGZKDVFQNNGYKY-UHFFFAOYSA-O 0.000 description 2
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical group C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 239000011230 binding agent Substances 0.000 description 2
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 2
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 230000002209 hydrophobic effect Effects 0.000 description 2
- 125000001972 isopentyl group Chemical group [H]C([H])([H])C([H])(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- 229910052757 nitrogen Inorganic materials 0.000 description 2
- 125000004433 nitrogen atom Chemical group N* 0.000 description 2
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- BWHMMNNQKKPAPP-UHFFFAOYSA-L potassium carbonate Chemical compound [K+].[K+].[O-]C([O-])=O BWHMMNNQKKPAPP-UHFFFAOYSA-L 0.000 description 2
- 229910052708 sodium Inorganic materials 0.000 description 2
- 239000011734 sodium Chemical group 0.000 description 2
- 235000011121 sodium hydroxide Nutrition 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 241000004297 Draba Species 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical group [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 1
- ZLMJMSJWJFRBEC-UHFFFAOYSA-N Potassium Chemical group [K] ZLMJMSJWJFRBEC-UHFFFAOYSA-N 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 150000001263 acyl chlorides Chemical class 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 150000008044 alkali metal hydroxides Chemical class 0.000 description 1
- 150000001340 alkali metals Chemical group 0.000 description 1
- 239000012670 alkaline solution Substances 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 125000000484 butyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 125000000753 cycloalkyl group Chemical group 0.000 description 1
- 230000007423 decrease Effects 0.000 description 1
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 239000002270 dispersing agent Substances 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 238000010438 heat treatment Methods 0.000 description 1
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- SUMDYPCJJOFFON-UHFFFAOYSA-N isethionic acid Chemical compound OCCS(O)(=O)=O SUMDYPCJJOFFON-UHFFFAOYSA-N 0.000 description 1
- 125000000400 lauroyl group Chemical group O=C([*])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 229910052744 lithium Inorganic materials 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001400 nonyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- IPCSVZSSVZVIGE-UHFFFAOYSA-N palmitic acid group Chemical group C(CCCCCCCCCCCCCCC)(=O)O IPCSVZSSVZVIGE-UHFFFAOYSA-N 0.000 description 1
- 229910052700 potassium Inorganic materials 0.000 description 1
- 239000011591 potassium Chemical group 0.000 description 1
- 229910000027 potassium carbonate Inorganic materials 0.000 description 1
- 235000011181 potassium carbonates Nutrition 0.000 description 1
- 235000011118 potassium hydroxide Nutrition 0.000 description 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000000243 solution Substances 0.000 description 1
- 125000001424 substituent group Chemical group 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000005406 washing Methods 0.000 description 1
- 238000005303 weighing Methods 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C11—ANIMAL OR VEGETABLE OILS, FATS, FATTY SUBSTANCES OR WAXES; FATTY ACIDS THEREFROM; DETERGENTS; CANDLES
- C11D—DETERGENT COMPOSITIONS; USE OF SINGLE SUBSTANCES AS DETERGENTS; SOAP OR SOAP-MAKING; RESIN SOAPS; RECOVERY OF GLYCEROL
- C11D1/00—Detergent compositions based essentially on surface-active compounds; Use of these compounds as a detergent
- C11D1/88—Ampholytes; Electroneutral compounds
-
- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
- C07C309/00—Sulfonic acids; Halides, esters, or anhydrides thereof
- C07C309/01—Sulfonic acids
- C07C309/02—Sulfonic acids having sulfo groups bound to acyclic carbon atoms
- C07C309/03—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton
- C07C309/13—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton
- C07C309/14—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton
- C07C309/15—Sulfonic acids having sulfo groups bound to acyclic carbon atoms of an acyclic saturated carbon skeleton containing nitrogen atoms, not being part of nitro or nitroso groups, bound to the carbon skeleton containing amino groups bound to the carbon skeleton the nitrogen atom of at least one of the amino groups being part of any of the groups, X being a hetero atom, Y being any atom
-
- 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
- Y10S516/03—Organic sulfoxy compound containing
- Y10S516/04—Protein or carboxylic compound containing
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Life Sciences & Earth Sciences (AREA)
- Engineering & Computer Science (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Wood Science & Technology (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Detergent Compositions (AREA)
Description
, oleic and the like.
Patented Sept. 8, 1953 UNETED STATES PATENT SURFACE ACTIVE AGENTS No Drawing. Application June 9, 1948, Serial No. 32,039
4 Claims.
The present invention relates to surface active agents of the N-acyl-N-aliphatic taurate class, and more particularly to such surface active agents having very high wetting power.
It has long been recognized that compounds containing a hydrophobic and a hydrophilic group possess surface activity. They are capable of reducing the surface tension of water and its interfacial tension against oils. They are good wetting agents, i. e., their solutions wet greasy surfaces much better than water does.
U. S. P. 1,932,180 discloses a number of N-acyl- N-aliphatic taurates, and states thatthey are suitable for use as Washing, cleansing, softening and dispersing agents.
A theory has been developed that improved surface activity is imparted to compounds containing a hydrophobic and hydrophilic group where a balance is struck between the two groups. It has been assumed that in compounds of the class of the aforementioned taurates, the ideal balance is realized where the acyl group is a radical derived from a higher molecular weight vegetal carboxylic acid, i. e., stearic, palmitic,
On the basis of this assumption, it has been believed that the substituent group on the nitrogen atom other than the acyl group has little effect on the surface activity of the involved compounds so long as it does not render the compounds insoluble. As a consequence there have been marketed for years compounds of the above class in which the aliphatic group is methyl and the acyl group is one of the aforesaid radicals.
I have now ascertained that this belief is incorrect and that maximum surface activity is portrayed by the taurates if a definite ratio be maintained between the sum of the carbon atoms in the acyl group and in the aliphatic substituent on the nitrogen atom on the one hand, and the carbon atoms in the acyl group, and such aliphatic substituent on the other hand.
Compounds possessing maximum surface activity by such apportionment of the carbon atoms in the involved radicals constitute the purposes and objects of the present invention.
The compounds contemplated herein have the following structural formula:
RC OITTCHZCHZSOZX wherein R is alkyl, R1 is an aliphatic hydrocarbon radical, i. e., alkyl or cycloalkyl, and X is hydrogen or an alkali metal or ammonium. In these compounds the sum of the carbon atoms in RCO and R1 must be at least 16 but not greater than 19. The number of carbon atoms in RCO must be at least 8 but not greater than 14, whereas the number of carbon atoms in R1 must be at least 5 but not greater than 8. This of course means that the carbon atoms in R must be in the range of from '7 to 13. It has been found that if these conditions are observed, the surface activity of the compounds is very high as calculated from wetting power according to the Braves method. If, however, the ratios set forth be disregarded, then automatically the wetting power of the resulting compounds decreases materially.
Based on the values given for RCO above, it will be apparent that R must be heptyl, octyl, nonyl, decyl, undecyl, dodecyl or tridecyl. E1, on the other hand, must be amyl, isoamyl, hexyl, heptyl, octyl, iso-octyl, cyclohexyl or the like, so long as the number of carbon atoms is within the stated range. X is hydrogen, sodium, potassium, lithium, ammonium or the like.
The compounds are prepared according to conventional methods, as by reacting the desired acyl chloride with the desired taurate salt in the presence of an acid binding agent at a temperature ranging from about 5 to 50 C. Suitable acid binding agents are caustic soda or pyridine.
The alkali metal salt of the taurines used are for the most part Well known compounds. In any case they can be prepared by heating to a temperature ranging from 180 to 240 C. an aqueous alkaline solution of hydroxyethyl sulfonic acid and the desired amine. The alkalinity may be supplied by the use of alkali metal hydroxide, such as caustic soda, caustic potash and the like, sodium carbonate, potassium carbonate, etc.
Examples of compounds embraced by the above formula and which we have found. to have very high wetting properties are the sodium or other alkali metal salt of:
. N-lauroyl-N-hexyl taurate;
. N-lauroyl-N-(amyl-isoamyl mixture) taurate; N -decanoyl-N-octyl taurate;
N-myristoyl-N-(amyl-isoamyl mixture) taurate;
N-decanoyl-N-heptyl taurate;
. N-caprylyl-N-octyl taurate;
. N-undecenoyl-N-octyl taurate;
. N-lauroyl-N-heptyl taurate;
. N-lauroyl-N-cyclohexyl taurate;
10. N-decanoyl-N(2-ethylhexy1) taurate.
The term amyl-isoamyl mixture as employed above means that the hydrocarbon substituent on the taurate-N atom is either the amyl or the isoamyl radical, i. e., the product is a mixture of the amyl and isoamyl derivatives. The corresponding taurate is prepared from a commercial mixture of amyl amines.
The invention is illustrated by the following table which discloses the wetting power of the compounds contemplated herein in terms of grams per liter of the wetting agent necessary to give a 25 second sinking time at 25 C. while utilizing a 1.5 gram hook or a 3.0 gram hook (Draves test). As test pieces, unboiled cotton skeins weighing 5 grams and being 18 inches in length are attached to the aforesaid hooks. The skeins are placed in a 500 cc. glass cylinder containing the wetting agent in aqueous solution.
The wetting efficiency of the compounds in this table is in marked contrast to the wetting efficiency of similar compounds, which, however, do not conform to the stated requirements. This is established by the following table:
R R, 1.5 Gm. Hook 8 3 12 lauroyl 1 methyl Too weak to measure 9. 5 l6 palmityL. 4 butyl 1.92 14 myristoyL. do. 1 1 11 undecenoyl... 1 methyl 7.35 6. 75 18 9-oc1tadece- 6 cyclohexyl. poor, inconsistent.-." 2. 50
noy
D 5 amy 4.5.. 2. 25
Various modifications of the invention will occur to persons skilled in this art, and I therefore do not intend to be limited in the patent granted except as necessitated by the appended claims.
I claim:
1. Compounds of the following formula:
RCONGHaGHzSOaX wherein R is an alkyl radical, R1 is a saturated aliphatic hydrocarbon radical, and X is selected from the class consisting of hydrogen and salt forming groups, the sum of the carbon atoms in RC0 and R1 being at least 16 but not greater than 19, the number of carbon atoms in RCO being at least 8 but not greater than 14 and the number of carbon atoms in R1 being at least 5 but not greater than 8.
2. The sodium salt of N-decanoyl-N-(Z-ethylhexyl) -taurine.
3. The sodium salt of N-lauroyl-N-hexyl taurine.
4. The mixture of the sodium salts of N- lauroyl-N-amyl-taurine and N-lauroyl-N-isoamyl taurine.
JAMES M. CROSS.
References Cited in the file of this patent UNITED STATES PATENTS Number Name Date 1,932,180 Guenther et a1. Oct. 24, 1933 2,045,015 Koerding et a1. June 23, 1936
Claims (1)
1. COMPOUNDS OF THE FOLLOWING FORMULA:
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32039A US2651645A (en) | 1948-06-09 | 1948-06-09 | Surface active agents |
| GB9890/49A GB661701A (en) | 1948-06-09 | 1949-04-12 | N-acyl-n-aliphatic taurates having surface active properties |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32039A US2651645A (en) | 1948-06-09 | 1948-06-09 | Surface active agents |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2651645A true US2651645A (en) | 1953-09-08 |
Family
ID=21862772
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US32039A Expired - Lifetime US2651645A (en) | 1948-06-09 | 1948-06-09 | Surface active agents |
Country Status (2)
| Country | Link |
|---|---|
| US (1) | US2651645A (en) |
| GB (1) | GB661701A (en) |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2739891A (en) * | 1953-07-17 | 1956-03-27 | Eastman Kodak Co | Method of preparing photographic products |
| US2821536A (en) * | 1953-02-16 | 1958-01-28 | Ruhrchemie Ag | Production of wetting, emulsifying and washing agent |
| US2964467A (en) * | 1956-05-04 | 1960-12-13 | Gen Aniline & Film Corp | Precipitation inhibiting |
| US3344174A (en) * | 1962-08-21 | 1967-09-26 | Monsanto Co | Vicinal acylamido sulfonate compounds |
| US3850610A (en) * | 1971-10-18 | 1974-11-26 | Gaf Corp | Herbicidal method |
| CN114181119A (en) * | 2021-12-18 | 2022-03-15 | 黄冈永安日用化工有限公司 | Preparation method of methyl lauroyl sodium taurate |
Families Citing this family (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3668179A (en) * | 1969-10-09 | 1972-06-06 | Mobil Oil Corp | Color stabilized polyolefin resins |
Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932180A (en) * | 1929-04-12 | 1933-10-24 | Ig Farbenindustrie Ag | Sulphuric acid derivatives of amides |
| US2045015A (en) * | 1931-06-09 | 1936-06-23 | Ig Farbenindustrie Ag | Production of sulphuric derivatives of fatty acid compounds |
-
1948
- 1948-06-09 US US32039A patent/US2651645A/en not_active Expired - Lifetime
-
1949
- 1949-04-12 GB GB9890/49A patent/GB661701A/en not_active Expired
Patent Citations (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1932180A (en) * | 1929-04-12 | 1933-10-24 | Ig Farbenindustrie Ag | Sulphuric acid derivatives of amides |
| US2045015A (en) * | 1931-06-09 | 1936-06-23 | Ig Farbenindustrie Ag | Production of sulphuric derivatives of fatty acid compounds |
Cited By (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2821536A (en) * | 1953-02-16 | 1958-01-28 | Ruhrchemie Ag | Production of wetting, emulsifying and washing agent |
| US2739891A (en) * | 1953-07-17 | 1956-03-27 | Eastman Kodak Co | Method of preparing photographic products |
| US2964467A (en) * | 1956-05-04 | 1960-12-13 | Gen Aniline & Film Corp | Precipitation inhibiting |
| US3344174A (en) * | 1962-08-21 | 1967-09-26 | Monsanto Co | Vicinal acylamido sulfonate compounds |
| US3850610A (en) * | 1971-10-18 | 1974-11-26 | Gaf Corp | Herbicidal method |
| CN114181119A (en) * | 2021-12-18 | 2022-03-15 | 黄冈永安日用化工有限公司 | Preparation method of methyl lauroyl sodium taurate |
Also Published As
| Publication number | Publication date |
|---|---|
| GB661701A (en) | 1951-11-28 |
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