US2130668A - Wetting, cleansing, and emulsifying agent - Google Patents
Wetting, cleansing, and emulsifying agent Download PDFInfo
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- US2130668A US2130668A US239003A US23900327A US2130668A US 2130668 A US2130668 A US 2130668A US 239003 A US239003 A US 239003A US 23900327 A US23900327 A US 23900327A US 2130668 A US2130668 A US 2130668A
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- Prior art keywords
- wetting
- acid
- cleansing
- organic
- nitrogen
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Classifications
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/325—Amines
- D06M13/335—Amines having an amino group bound to a carbon atom of a six-membered aromatic ring
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/10—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing oxygen
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/244—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus
- D06M13/248—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
- D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
- D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
- D06M13/35—Heterocyclic compounds
- D06M13/355—Heterocyclic compounds having six-membered heterocyclic rings
-
- 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
-
- 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
- Y10S516/05—Organic amine, amide, or n-base containing
Definitions
- Organic sulfonic acids of high wetting power which are 15 to be employed according to the present invention comprise only such acids of which a 0.5 per cent aqueous solution of their sodium salt wets a felt-like textile fabric, for example, of wool or cotton in atthe most one hour, but preferably 20 in a much shorter time, for example in a few minutes.
- Organic sulfonic acids of the said kind which are particularly suitable for the purpose of the present inventlon'are aromatic sulfonic acids containing alkyl-, aralkyl-, cycloalkyl-, or 25 aryl groups, which may, if desired, be further substituted, whether in the nucleus or in the side chain, further sulfonic acids of aliphatic or hydroaromatic compounds, for example the sulfonation products of mineral oils, aliphatic tar o oils, naphthenic acids and the like, as well as the known fat-splitting acids, or the ligno-sulfonic acids contained in sulflte-cellulose waste liquor.
- organic bases suitable for preparing the said agents aliphatic amines, such as methylamine or ethylamine, mono-, di-, or triethanolamine, 40 but particularly the heterocyclic nitrogen-containing bases, such as pyridine and its homologues and derivatives, and the like, may be mentioned.
- the said components for manufacturing the 45 new products imparting to aqueous liquids a high wetting, cleansing and emulsifying action may be prepared before use by mixing them with each other in the absence of water in up to equivalent amounts, the nitrogenous base being 50 always employed in a substantial quantity, i. e.,
- aqueous liquids of high wetting and cleansing properties it is generally sufllcient to add to the liquids about 0.5 per cent of the said preparations.
- Aqueous liquids of a'higher concentration may also be used. If the said preparations are to be used for preparing highly stable aqueous emulsions or suspensions, or even clear aqueous solutions of substances insoluble in water, higher concentrations of the preparations are often needed. Also dry compomtions of solids, for instance dyestufis, with the agents according to the present invention may be prepared, which when diluted with water furnish stable suspensions or even clear.
- Example 1 If an acid sulphuric ester of oleic acid, prepared by treating oleic acid with sulfuric acid, be treated with an equivalent amount of caustic soda solution on the one hand and an equivalent amount of pyridine on the other, the aqueous solution, which contains the mixed pyridine and sodium salt of the acid sulfuric ester of oleic acid, displays a far greater capacity for wettingtextiles than an equally concentrated aqueous solution of the acid sulfuric ester of oleic acid either neutralized with caustic soda solution or in the free state.
- the corresponding salts of isobutylamine, triethanolamine, or other amines behave in an equally favorable manner.
- the dibutylnaphthalane-sulfonic acid may be replaced by other sulfonic acids of the character defined. such as those of methyl-, ethyl-, propylor also cycloalkylsubstituted organic compounds.
- Example 3 An approximately 0.5 per cent solution of a crude gas-oil sulfonic acid, i. e., the sulfonation product of a brown coal tar fraction boiling between 225 and 360 0., in water is treated with the calculated amount of dimethylaniline. The resulting solution containing the salt of the said acid with dimethylaniline possesses excellent wetting properties.
- Example 5 2 parts of naphthenic acid are treated with equivalent quantities of either methylamine, isobutylamine, or triethanolamine, and dissolved in sumcient water to form 500 parts. All these solutions containing the corresponding salts exhibit very good wetting properties, substantially more than the corresponding sodium salt.
- a process of producing wetting, cleansing and emulsifying agents which comprises mixing a wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power with about equivalent amounts of an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic heterocyclic bases, in which nitrogen is the hetero atom.
- Wetting, cleansing and emulsifying products comprising an organic acid wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power and about equivalent amounts of an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic h'eterocyclic bases in which nitrogen is the hetero a cm.
- an organic acid wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power and about equivalent amounts of an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic h'eterocyclic bases in which nitrogen is the hetero a cm.
- wettin cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an allnrl group and about equivalent amounts of a monocyclic pyridine base.
- a sulphonated oleaginous compound fluidified by an ethanolamine 16.
- a suiphonated oleaginous compound fluidifled by tri-ethanoiamine 17.
- a suiphonated oleaginous compound fluidifled by tri-ethanoiamine. 18.
- Wetting, cleansing and emulsifying products essentially comprising an admixture of a monocyclic heterocyclic base in which nitrogen is the hetero atom, and an aromatic sulio 'acid, said acid being an acid of high wetting power.
- cleansing and emulsifying products essentially comprising an admixture of a monocyclic heterocyclic base in which nitrogen is the hetero atom and a sulio acid of the monocyclic heterocyclic base in which nitrogen s0 is the hetero .atom and a sulfo acid of an aromatic naphthalene aliphatically substituted in the nucleus.
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- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Detergent Compositions (AREA)
- Cosmetics (AREA)
Description
I Patented Sept. 20, 1938 UNITED STATES PATENT OFFICE WETTING, CLEANSING, AND EMULSIFYING AGENT Fritz Giinther, Ludwigshafen-on-the-Rhine, Germany, assignor to I. G. Farbenlndustrie Aktiengesellschaft, Frankfort-on-the-Main, Germany, a corporation of Germany No Drawing. Application December 9, 1927, Se-
rial No. 239,003. 1926 of nitrogen-containing organic bases. Organic sulfonic acids of high wetting power which are 15 to be employed according to the present invention comprise only such acids of which a 0.5 per cent aqueous solution of their sodium salt wets a felt-like textile fabric, for example, of wool or cotton in atthe most one hour, but preferably 20 in a much shorter time, for example in a few minutes. Organic sulfonic acids of the said kind which are particularly suitable for the purpose of the present inventlon'are aromatic sulfonic acids containing alkyl-, aralkyl-, cycloalkyl-, or 25 aryl groups, which may, if desired, be further substituted, whether in the nucleus or in the side chain, further sulfonic acids of aliphatic or hydroaromatic compounds, for example the sulfonation products of mineral oils, aliphatic tar o oils, naphthenic acids and the like, as well as the known fat-splitting acids, or the ligno-sulfonic acids contained in sulflte-cellulose waste liquor. These acids yield excellent wetting, cleansing and emulsifying agents when treated with organic 35 nitrogen-containing bases in the above specified amounts. As organic bases suitable for preparing the said agents, according to the present invention, aliphatic amines, such as methylamine or ethylamine, mono-, di-, or triethanolamine, 40 but particularly the heterocyclic nitrogen-containing bases, such as pyridine and its homologues and derivatives, and the like, may be mentioned.
The said components for manufacturing the 45 new products imparting to aqueous liquids a high wetting, cleansing and emulsifying action may be prepared before use by mixing them with each other in the absence of water in up to equivalent amounts, the nitrogenous base being 50 always employed in a substantial quantity, i. e.,
in a quantity of at least 10 per cent of the equivalent amount, or by preparing them in the form of their salts by working in aqueous solution, or they may be produced only in the liquid or prep- 5 aration with which they are to be used, byadd- In Germany December 11,
23 Claims. (01. zeoi-z so ing the required components thereto. It is to be understood that in the production of the new products no heating or other strong condition of working is applied, since otherwise condensation or other reactions would occur which may leaicsl to the formation of water insoluble produc When the substances are mixed no heat is applied and the usual reaction of an acid with a base occurs, namely, the formation of a salt cor- :Iesponding for example to the following equaons:
Mono-sulfuric ester of com- 0 pound R \N R-S 0,-011 if 12-8 0, Suiionic acid oi com poun'd 0 n-co-on i( n-co Oarboxyiic acid of com- 0 pound R The fact that a salt is actually formed is evidenced by the reduction of the acidity of the solutions of the acids when the nitrogenous base desired is added. These salts, moreover, are water-soluble salts since the formation of amides or imides would become obvious by the insolubility of the products.
It is not essential for the purpose of this in vention that the equivalent quantity of the organic nitrogen bases is added to the acids. Even acids which are only partially so saturated exhibit an excellent wetting action. Very useful effects are also obtained with mixed salts prepared by adding to the said acids either several different organic nitrogen bases, or by replacing a portion of the latter by inorganic bases, such as caustic soda, ammonia and the like.
For preparing aqueous liquids of high wetting and cleansing properties it is generally sufllcient to add to the liquids about 0.5 per cent of the said preparations. Aqueous liquids of a'higher concentration, however, may also be used. If the said preparations are to be used for preparing highly stable aqueous emulsions or suspensions, or even clear aqueous solutions of substances insoluble in water, higher concentrations of the preparations are often needed. Also dry compomtions of solids, for instance dyestufis, with the agents according to the present invention may be prepared, which when diluted with water furnish stable suspensions or even clear.
solutions of the said solids.
The following examples further illustrate the nature of this invention, which however is not restricted to these examples. The parts are by weight.
Example 1 If an acid sulphuric ester of oleic acid, prepared by treating oleic acid with sulfuric acid, be treated with an equivalent amount of caustic soda solution on the one hand and an equivalent amount of pyridine on the other, the aqueous solution, which contains the mixed pyridine and sodium salt of the acid sulfuric ester of oleic acid, displays a far greater capacity for wettingtextiles than an equally concentrated aqueous solution of the acid sulfuric ester of oleic acid either neutralized with caustic soda solution or in the free state.
Ezrample 2 To a solution of one part of dibutylnaphtha= lene-sulfonic acid in 200 parts of water, 0.3 part of pyridine is added and the solution is made up to 250 parts with water. The wetting properties of the resulting solution containing the corresponding pyridine salt are considerably better than those of a solution of the free acid or its sodium salt of the same concentration.
The corresponding salts of isobutylamine, triethanolamine, or other amines, behave in an equally favorable manner. The dibutylnaphthalane-sulfonic acid may be replaced by other sulfonic acids of the character defined. such as those of methyl-, ethyl-, propylor also cycloalkylsubstituted organic compounds.
Example 3 An approximately 0.5 per cent solution of a crude gas-oil sulfonic acid, i. e., the sulfonation product of a brown coal tar fraction boiling between 225 and 360 0., in water is treated with the calculated amount of dimethylaniline. The resulting solution containing the salt of the said acid with dimethylaniline possesses excellent wetting properties.
Ezmmple 4 To 5 parts of a tri-isopropylbenzenesulfonic acid the equivalent quantity of isobutylamine is added, and the mixture is dissolved in suflicient water to form 1000 parts. The solution containing the corresponding salts has very good wetting properties.
Example 5 2 parts of naphthenic acid are treated with equivalent quantities of either methylamine, isobutylamine, or triethanolamine, and dissolved in sumcient water to form 500 parts. All these solutions containing the corresponding salts exhibit very good wetting properties, substantially more than the corresponding sodium salt.
What I claim is:
1. As new articles of manufacture wetting, cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an alkyl group, and a substantial proportion up to equivaleint amounts of an organic nitrogen-containing base selected from the group consisting 3. As new articles of manufacture wetting, cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an 9.1%! group, and a substantial proportion up to equivalent amounts ofpyridine,
4. As new articles of manufacture the salts formed by an organic acid wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power with an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic pyridine bases.
5. As new articles of manufacture the salts formed by a naphthalene sulfonic acid substituted by an alkyl group, with an organic nitrogencontaining base selected from the group consisttug of aliphatic amines and monocyclic pyridine ases.
6. As new articles of manufacture the salts formed by a naphthalene sulfonic acid substituted ggisan alkyl group, with a monocyclic pyridine e. 7. As new articles of manufacture the salts formed by a naphthalene sulfonic acid substituted by an alhl group with pyridine.
8. A process of producing wetting, cleansing and emulsifying agents which comprises mixing a wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power with about equivalent amounts of an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic heterocyclic bases, in which nitrogen is the hetero atom.
9. Wetting, cleansing and emulsifying products comprising an organic acid wetting agent selected from the group consisting of organic sulfonic acids and sulfuric esters of high wetting power and about equivalent amounts of an organic nitrogen containing base selected from the group consisting of aliphatic amines and monocyclic h'eterocyclic bases in which nitrogen is the hetero a cm.
10. As new articles of manufacture wetting, cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an alkyl group and about equivalent amounts of an organic nitrogencontaining base selected from the group consisting of aliphatic amines and monocyclic pyridine bases.
11. As a new articles of manufacture wettin cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an allnrl group and about equivalent amounts of a monocyclic pyridine base.
12. As new articles of manufacture wetting, cleansing and emulsifying products comprising a naphthalene sulfonic acid substituted by an alkyl group and about equivalent amounts of pyridine.
13. As new articles of manufacture the salts of alkyl naphthalene sulphonic acids with alkylol amines.
14. As a new articles of manufacture a salt of a dibutyl naphthalene suiphonic acid with triethanol amine.
15. The process of producing a substance which will form a soluble compound with salts of the alkaline earth of hard waters, consisting in adding ethanolamines to sulphonated oils.
16. A sulphonated oleaginous compound fluidified by an ethanolamine.
17. A suiphonated oleaginous compound fluidifled by tri-ethanoiamine. 18. Wetting, cleansing and emulsifying products essentially comprising an admixture of a monocyclic heterocyclic base in which nitrogen is the hetero atom, and an aromatic sulio 'acid, said acid being an acid of high wetting power.
19. Wetting; cleansing and emulsifying products essentially comprising an admixture of a monocyclic heterocyclic base in which nitrogen is the hetero atom and a sulio acid of the monocyclic heterocyclic base in which nitrogen s0 is the hetero .atom and a sulfo acid of an aromatic naphthalene aliphatically substituted in the nucleus.
21. Wetting, cleansing and emulsifying products essentially comprising an admixture of a monocyclic heterocyclic base in which nitrogen is the hetero atom and an alkylated sulfo acid of the naphthalene group.
22. Wetting, cleansing and emulsifying products essentially comprising an admixture of a water-soluble monocyclic heterocyclic base in which nitrogen is the hetero atom and aromatic sulfo acid, said acid being an acid of high wetting power.
23. Wetting, cleansing and emulsifying products essentially comprising an admixture of a sulfo acid of an aromatic poly-nuclear hydrowhich nitrogen is the hetero atom, said acid being an acid of high wetting power.
FRITZ GUNI'I-IER.
carbon and a monocyclic heterocyclic base in
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE2130668X | 1926-12-11 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2130668A true US2130668A (en) | 1938-09-20 |
Family
ID=7986408
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US239003A Expired - Lifetime US2130668A (en) | 1926-12-11 | 1927-12-09 | Wetting, cleansing, and emulsifying agent |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2130668A (en) |
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2435925A (en) * | 1944-11-22 | 1948-02-10 | Visco Products Co | Reverse detergent |
| US2443716A (en) * | 1943-09-24 | 1948-06-22 | Allied Chem & Dye Corp | Surface-active nitrosation-sulfitation products |
| US2451549A (en) * | 1945-08-30 | 1948-10-19 | Atlantic Refining Co | Production of metal sulfonates |
| US2472583A (en) * | 1944-11-07 | 1949-06-07 | Atlantic Refining Co | Production of cyclic nitrogen base sulfonates |
| US2476411A (en) * | 1944-11-07 | 1949-07-19 | Atlantic Refining Co | Adhesivity of bitumens for mineral aggregates |
| US2537428A (en) * | 1951-01-09 | Pikridiniem sulfo cobipounds | ||
| US2569326A (en) * | 1948-07-30 | 1951-09-25 | J B Niederl & Associates Inc | Unsymmetrical quaternary ammonium alkyl sulfates |
| US2769789A (en) * | 1952-01-15 | 1956-11-06 | Dunlop Tire & Rubber Corp | Rubber reinforcing agents and compositions containing such agents |
| US3001996A (en) * | 1957-02-08 | 1961-09-26 | Hans S Mannheimer | Sulfates and sulfonates of n-tertiary amino alkyl-carboxylic acid amides |
| US4018591A (en) * | 1967-12-15 | 1977-04-19 | Prodotti Gianni S.R.L. | Product for activating and potentiating vegetable metabolism and for conditioning agricultural soil and method for the preparation thereof |
-
1927
- 1927-12-09 US US239003A patent/US2130668A/en not_active Expired - Lifetime
Cited By (10)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2537428A (en) * | 1951-01-09 | Pikridiniem sulfo cobipounds | ||
| US2443716A (en) * | 1943-09-24 | 1948-06-22 | Allied Chem & Dye Corp | Surface-active nitrosation-sulfitation products |
| US2472583A (en) * | 1944-11-07 | 1949-06-07 | Atlantic Refining Co | Production of cyclic nitrogen base sulfonates |
| US2476411A (en) * | 1944-11-07 | 1949-07-19 | Atlantic Refining Co | Adhesivity of bitumens for mineral aggregates |
| US2435925A (en) * | 1944-11-22 | 1948-02-10 | Visco Products Co | Reverse detergent |
| US2451549A (en) * | 1945-08-30 | 1948-10-19 | Atlantic Refining Co | Production of metal sulfonates |
| US2569326A (en) * | 1948-07-30 | 1951-09-25 | J B Niederl & Associates Inc | Unsymmetrical quaternary ammonium alkyl sulfates |
| US2769789A (en) * | 1952-01-15 | 1956-11-06 | Dunlop Tire & Rubber Corp | Rubber reinforcing agents and compositions containing such agents |
| US3001996A (en) * | 1957-02-08 | 1961-09-26 | Hans S Mannheimer | Sulfates and sulfonates of n-tertiary amino alkyl-carboxylic acid amides |
| US4018591A (en) * | 1967-12-15 | 1977-04-19 | Prodotti Gianni S.R.L. | Product for activating and potentiating vegetable metabolism and for conditioning agricultural soil and method for the preparation thereof |
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