US2389875A - Surface active agents - Google Patents
Surface active agents Download PDFInfo
- Publication number
- US2389875A US2389875A US540537A US54053744A US2389875A US 2389875 A US2389875 A US 2389875A US 540537 A US540537 A US 540537A US 54053744 A US54053744 A US 54053744A US 2389875 A US2389875 A US 2389875A
- Authority
- US
- United States
- Prior art keywords
- surface active
- wetting
- agents
- aminoisobutyl
- amines
- 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
- 239000004094 surface-active agent Substances 0.000 title description 7
- -1 N-(2-aminoisobutyl) -1-methylheptylamine Chemical compound 0.000 description 12
- 238000009736 wetting Methods 0.000 description 12
- 150000001412 amines Chemical class 0.000 description 11
- 239000000080 wetting agent Substances 0.000 description 10
- 239000000463 material Substances 0.000 description 9
- 238000000034 method Methods 0.000 description 8
- 239000004753 textile Substances 0.000 description 7
- 238000004043 dyeing Methods 0.000 description 6
- 239000002657 fibrous material Substances 0.000 description 5
- 239000003795 chemical substances by application Substances 0.000 description 4
- 239000003599 detergent Substances 0.000 description 4
- 239000000975 dye Substances 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- QFKMMXYLAPZKIB-UHFFFAOYSA-N undecan-1-amine Chemical compound CCCCCCCCCCCN QFKMMXYLAPZKIB-UHFFFAOYSA-N 0.000 description 3
- IMBNEKOMEDCTCL-UHFFFAOYSA-N 2-methyl-1-piperidin-1-ylpropan-2-amine Chemical compound CC(C)(N)CN1CCCCC1 IMBNEKOMEDCTCL-UHFFFAOYSA-N 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 239000011149 active material Substances 0.000 description 2
- 239000013543 active substance Substances 0.000 description 2
- 239000003513 alkali Substances 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 239000006260 foam Substances 0.000 description 2
- 239000010985 leather Substances 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 230000000149 penetrating effect Effects 0.000 description 2
- 150000007519 polyprotic acids Polymers 0.000 description 2
- 239000000344 soap Substances 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 241000004297 Draba Species 0.000 description 1
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 1
- DWAQJAXMDSEUJJ-UHFFFAOYSA-M Sodium bisulfite Chemical compound [Na+].OS([O-])=O DWAQJAXMDSEUJJ-UHFFFAOYSA-M 0.000 description 1
- 229920006221 acetate fiber Polymers 0.000 description 1
- 150000007513 acids Chemical class 0.000 description 1
- 238000005904 alkaline hydrolysis reaction Methods 0.000 description 1
- 125000000217 alkyl group Chemical group 0.000 description 1
- 238000004061 bleaching Methods 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 125000004432 carbon atom Chemical group C* 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000009903 catalytic hydrogenation reaction Methods 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 230000000052 comparative effect Effects 0.000 description 1
- 125000005265 dialkylamine group Chemical group 0.000 description 1
- 230000032050 esterification Effects 0.000 description 1
- 238000005886 esterification reaction Methods 0.000 description 1
- 239000000835 fiber Substances 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000007791 liquid phase Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- MCSAJNNLRCFZED-UHFFFAOYSA-N nitroethane Chemical group CC[N+]([O-])=O MCSAJNNLRCFZED-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000014593 oils and fats Nutrition 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 238000004513 sizing Methods 0.000 description 1
- 235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
- HFQQZARZPUDIFP-UHFFFAOYSA-M sodium;2-dodecylbenzenesulfonate Chemical compound [Na+].CCCCCCCCCCCCC1=CC=CC=C1S([O-])(=O)=O HFQQZARZPUDIFP-UHFFFAOYSA-M 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 125000000020 sulfo group Chemical group O=S(=O)([*])O[H] 0.000 description 1
- 238000006277 sulfonation reaction Methods 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-N sulfuric acid Substances OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 1
- 239000012209 synthetic fiber Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 239000000984 vat dye Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000003643 water by type Substances 0.000 description 1
Classifications
-
- 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
- C09K23/16—Amines or polyamines
-
- 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
-
- 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
- My invention relates to new and useful surface, or capillary active substances and more particularly it pertains to the utilization of certain amines to greatly reduce the surface tension of various aqueous mixtures and thereby increase the wetting properties thereof.
- amines serve as highly satisfactory wetting agents in wetting and assisting in the spreading of various solutions on solid surfaces, particularly, where prior wetting and detergent agents, especially o the type mentioned above, are of little or no value.
- the amines which I have found operative are l-methylheptylamine, N-(2-aminoisobutyl) -1-methylheptylamine, N- (2-aminoisobutyDhendecylamine, N (2 aminoisobutyl) piperidine, and N- (2-aminoisobutyl) -2,4-dimethylaniline.
- the wetting agents of the present invention for example are not decomposed either by hard waters or solutions containing appreciable quantities of alkali.
- My new wetting agents possess the further advantage in that aqueous solutions thereof do not foam.
- these materials which are generally water white liquids, are soluble in most of the common organic solvents.
- amines of the above type exhibit surface active properties. To my knowledge such amines have never before been known to possess such characteristics. A further surprising factor is that while the aforesaid amines have been found to be excellent surface active agents, numerous of their close homologues have been tested and were found to possess substantially no surface active properties whatever.
- the quantity of the new wetting agents which may be employed will be found to vary with the type of wetting operation under consideration as well as with the material to be Wetted. For most purposes, however, I have found that these wetting agents may be utilized in amounts of from about 0.1 to 0.6% by Weight of the treating bath.
- the wetting power of the amines of the present invention is demonstrated by the data appearing in the table below and was measured by the method of Draves and Clarkson (Amer. Assoc. Textile Colorists and Chemists Year Book -vol. 17,- pp.
- amines of the latter type are synthesized by subjecting the corresponding nitro amine to catalytic hydrogenation in the liquid phase at superatmospheric temperatures
- the nitro amines utilized in this process are prepared in accordance with the procedure described in my copending application U. 5. Serial No. 455,931, filed August 24, 1942. According to this procedure, a primary or secondary aliphatic amine is reacted with formaldehyde to form the corresponding N-hydroxymethyl monoor dialkylamine which is in turn reacted with an equimoiecular quantity of a secondary nitroparaffin to produce the desired nitro amine.
- an alkaline catalyst should be used.
- nitro amines are prepared at temperatures of from between about 25 and 30 C. Temperatures above this range may be used but in doing so care should be exercised to avoid temthey are added to baths containing starchy fermnts which are employed for removing sizing from textile materials.
- These products function as useful wetting, cleansing, and penetrating agents in bleaching liquors such as those used in the kier boiling of cotton goodsand may be added to the lye liquors used for mercerizing cotton goods. They can also be used to assist in twist setting of yarn and in processes of stripping colors.
- Such compounds may also be used as assistants in processes of stripping dyes from dyed textile material.
- a second class of uses of these new surface active agents is as assistants in the application of dyestufls. They may be used as dye leveling agents owing to their .wetting and.
- penetrating properties in neutral or alkaline dyeing baths are capable of facilitating dyeing with developed dyes, the dyeing of acetate fibers with insoluble dyes, the dyeing. of animal fibers with vat dyes, the dyeing of various synthetic fibers and the dyeing of leather.
- An aqueous bath for the wet treatment of organic fibrous materials comprising an amine selected from the class consisting of N- (2-aminoisobutyl) -l-methylheptylamine, N- (2-aminoisobutyl) hendecylamine, N (2 aminoisobutyl) piperidine, l-methylheptylamine, and N-(Z-aminoisobutyl) -2,4-dimethylaniline.
- An aqueous bath for the wet treatment of organic fibrous materials comprising from about 0.1 to 0.6% by weight of the treating bath of an amineselected from the group consisting of N- (2- aminoisobutyl) -1-methylheptylamine, N- (2-aminoisobutyl) hendecylamine, N -(2 aminoisobw tyDpiperidine, l-methylheptylamine, and N-(2- aminoisobutyl) -2,4-dimethylaniline.
- an amines selected from the group consisting of N- (2- aminoisobutyl) -1-methylheptylamine, N- (2-aminoisobutyl) hendecylamine, N -(2 aminoisobw tyDpiperidine, l-methylheptylamine, and N-(2- aminoisobutyl) -2,4-dimethylaniline.
- An aqueous bath for the wet treatment of organic fibrous materials comprising N- (Z-aminoisobutyl) -1-methylheptylamine.
- An aqueous bath for the wet treatment of organic fibrous materials comprising N- (2-aminoisobutyl) hendecylamine.
- An aqueous bath for the wet treatment of organic fibrous materials comprising l-methylheptylamine.
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Organic Chemistry (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Nov. 27, 1945 SURFACE ACTIVE AGENTS Murray Senkus, Terre Haute, Ind., assignor to Commercial Solvents Corporation, Terre Haute, Ind., a corporation of Maryland No Drawing. Application June 15, 1944, Serial No. 540,537
Claims.
My invention relates to new and useful surface, or capillary active substances and more particularly it pertains to the utilization of certain amines to greatly reduce the surface tension of various aqueous mixtures and thereby increase the wetting properties thereof.
There exists in numerous industries a growing need for certain types of chemical compounds, usually employed in small quantities, to secure an effect which is principally the result of a wet ting action such as the effect obtained by the presence of a surface active agent at a water-oil interface. For example, in the textile and leather treating industries, there are many operational steps where wetting or detergent action is highly desirable. As a result many different agents have been proposed to reduce surface tension and promote the wetting power of various types of aqueous mixtures. The materials previously used, however, although satisfactory in some respects, were not entirely free from certain material disadvantages.
In an effort to furnish materials to the textile and related industries free from the undesirable properties of ordinary soaps and other similar commonly known surface active agents, there have been developed as detergent and wetting agents products obtained by the sulfonation of certain fatty acids occurring in oils and fats. Such fatty acids are characterized by the presence of unsaturated linkages and/or hydroxyl groups in the molecule. On sulfonating such acids, products, are obtained which contain sulfuric acid ester groups in the molecule and, of course, carboxylic acid groups are attahed to the terminal carbon atoms. in general possess weaker wetting and detergent properties than soaps. Such products are also relatively unstable and are decomposed by alkaline hydrolysis.
Other proposed wetting agents comprise the semi and completely esterified products resulting from the esterification of a higher alcohol with an unsaturated polybasic acid. After the unsaturated esterified acid is produced, it is converted into a more soluble form, ordinarily by treatment with sodium bisulfite to yield the corresponding sulfo derivatives of the esterified polybasic acid. While such materials have met with a considerable degree of success in various in- The products, however,
dustries where the need for surface active materials exists, they also possess certain disadvantages. Obviously, surface active agents of this type are not stable to alkali and in some instances, especially in the textile field, much difliculty has been experienced with the tendency of the textile treating baths containing such materials to foam.
I have now discovered that certain amines serve as highly satisfactory wetting agents in wetting and assisting in the spreading of various solutions on solid surfaces, particularly, where prior wetting and detergent agents, especially o the type mentioned above, are of little or no value. Specifically the amines which I have found operative are l-methylheptylamine, N-(2-aminoisobutyl) -1-methylheptylamine, N- (2-aminoisobutyDhendecylamine, N (2 aminoisobutyl) piperidine, and N- (2-aminoisobutyl) -2,4-dimethylaniline. The wetting agents of the present invention, for example are not decomposed either by hard waters or solutions containing appreciable quantities of alkali. My new wetting agents possess the further advantage in that aqueous solutions thereof do not foam. In addition these materials, which are generally water white liquids, are soluble in most of the common organic solvents.
One of the outstanding and surprising features of my invention is the fact that amines of the above type exhibit surface active properties. To my knowledge such amines have never before been known to possess such characteristics. A further surprising factor is that while the aforesaid amines have been found to be excellent surface active agents, numerous of their close homologues have been tested and were found to possess substantially no surface active properties whatever.
In general, the quantity of the new wetting agents which may be employed will be found to vary with the type of wetting operation under consideration as well as with the material to be Wetted. For most purposes, however, I have found that these wetting agents may be utilized in amounts of from about 0.1 to 0.6% by Weight of the treating bath.
The wetting power of the amines of the present invention is demonstrated by the data appearing in the table below and was measured by the method of Draves and Clarkson (Amer. Assoc. Textile Colorists and Chemists Year Book -vol. 17,- pp.
216-22 (1940)), which determines the sinking time required for a 5 g. skein of unboiled 2-ply cotton yarn in varying concentrations of aqueous solutions of the amines at a temperature of 30 C. The data. below also show the comparative wetting powers of the wetting agents of the present invention and Santomerse No. 1 (a sulfonated alkyl di-phenyl) a commercially available wetting agent.
- and pressures.
While l-methylheptylamine can be synthesized in any of several ways known to the art, the remaining compounds are most convenientl prepared in accordance with the procedures of my vcopending application, U. S. Serial No. 455,932,
filed August 24, 1942. By the procedure there described and claimed, amines of the latter type are synthesized by subjecting the corresponding nitro amine to catalytic hydrogenation in the liquid phase at superatmospheric temperatures The nitro amines utilized in this process are prepared in accordance with the procedure described in my copending application U. 5. Serial No. 455,931, filed August 24, 1942. According to this procedure, a primary or secondary aliphatic amine is reacted with formaldehyde to form the corresponding N-hydroxymethyl monoor dialkylamine which is in turn reacted with an equimoiecular quantity of a secondary nitroparaffin to produce the desired nitro amine. In the event anaromatic amine is employed an alkaline catalyst should be used. The preparation of such nitro amines ispreferably carried out at temperatures of from between about 25 and 30 C. Temperatures above this range may be used but in doing so care should be exercised to avoid temthey are added to baths containing starchy fermnts which are employed for removing sizing from textile materials. These products function as useful wetting, cleansing, and penetrating agents in bleaching liquors such as those used in the kier boiling of cotton goodsand may be added to the lye liquors used for mercerizing cotton goods. They can also be used to assist in twist setting of yarn and in processes of stripping colors. Such compounds may also be used as assistants in processes of stripping dyes from dyed textile material. A second class of uses of these new surface active agents is as assistants in the application of dyestufls. They may be used as dye leveling agents owing to their .wetting and.
penetrating properties in neutral or alkaline dyeing baths and are capable of facilitating dyeing with developed dyes, the dyeing of acetate fibers with insoluble dyes, the dyeing. of animal fibers with vat dyes, the dyeing of various synthetic fibers and the dyeing of leather.
It will readily be seen from the foregoing dis-. cussion that by means of the present invention, a group of new surface active materials has been made available and that such agents are adapted for use in numerous industrial processes which require surface active substances.
\ apparent to those skilled in the art that many widely difierent embodiments of the present invention exist and that such embodiments may be utilized without departing from the scope of said invention.
My invention now having been described what I claim is:
1. An aqueous bath for the wet treatment of organic fibrous materials comprising an amine selected from the class consisting of N- (2-aminoisobutyl) -l-methylheptylamine, N- (2-aminoisobutyl) hendecylamine, N (2 aminoisobutyl) piperidine, l-methylheptylamine, and N-(Z-aminoisobutyl) -2,4-dimethylaniline.
2. An aqueous bath for the wet treatment of organic fibrous materials comprising from about 0.1 to 0.6% by weight of the treating bath of an amineselected from the group consisting of N- (2- aminoisobutyl) -1-methylheptylamine, N- (2-aminoisobutyl) hendecylamine, N -(2 aminoisobw tyDpiperidine, l-methylheptylamine, and N-(2- aminoisobutyl) -2,4-dimethylaniline.
3. An aqueous bath for the wet treatment of organic fibrous materials comprising N- (Z-aminoisobutyl) -1-methylheptylamine.
4. An aqueous bath for the wet treatment of organic fibrous materials comprising N- (2-aminoisobutyl) hendecylamine.
5. An aqueous bath for the wet treatment of organic fibrous materials comprising l-methylheptylamine.
MURRAY SENKUS.
It will also be
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US540537A US2389875A (en) | 1944-06-15 | 1944-06-15 | Surface active agents |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US540537A US2389875A (en) | 1944-06-15 | 1944-06-15 | Surface active agents |
Publications (1)
Publication Number | Publication Date |
---|---|
US2389875A true US2389875A (en) | 1945-11-27 |
Family
ID=24155875
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US540537A Expired - Lifetime US2389875A (en) | 1944-06-15 | 1944-06-15 | Surface active agents |
Country Status (1)
Country | Link |
---|---|
US (1) | US2389875A (en) |
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2925639A (en) * | 1953-11-30 | 1960-02-23 | Deering Milliken Res Corp | Method of fulling and scouring wool |
US3023141A (en) * | 1955-12-30 | 1962-02-27 | Babcock & Wilcox Co | Method of forming a mineral wool pad |
US3404777A (en) * | 1965-05-07 | 1968-10-08 | Armour & Co | Froth flotation with secondary-alkyl primary amines |
-
1944
- 1944-06-15 US US540537A patent/US2389875A/en not_active Expired - Lifetime
Cited By (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2925639A (en) * | 1953-11-30 | 1960-02-23 | Deering Milliken Res Corp | Method of fulling and scouring wool |
US3023141A (en) * | 1955-12-30 | 1962-02-27 | Babcock & Wilcox Co | Method of forming a mineral wool pad |
US3404777A (en) * | 1965-05-07 | 1968-10-08 | Armour & Co | Froth flotation with secondary-alkyl primary amines |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US2085706A (en) | Derivatives of carboxylic acid amides | |
US2267205A (en) | Detergent | |
US2002613A (en) | Reaction product of an organic acid amide and an alkylene oxide | |
US3138610A (en) | Substituted imidazolines | |
US2052192A (en) | Boric acid esters | |
US2923724A (en) | Process of preparing ester type anionic surface active agents | |
US2239974A (en) | Detergent composition | |
GB380851A (en) | Improvements in the manufacture and production of assistants in the textile and related industries and dispersing agents | |
US2164431A (en) | Production of etherg suitable as dis | |
US2185163A (en) | Polyoxyalkylene ammonium compounds and process of preparing them | |
US2389875A (en) | Surface active agents | |
US2402791A (en) | Reaction product of oxazolines | |
US1985747A (en) | Ether-like constituted compound | |
US2256877A (en) | Wetting, penetrating, foaming, and dispersing agent | |
US2860160A (en) | Preparation of aminoalkyl acids and derivatives thereof | |
US2159967A (en) | Oxides of amino acids | |
US2229649A (en) | Sulphated methyl heptadecenyl carbinol | |
US2040997A (en) | Esters of boric acid | |
US2317555A (en) | Surface active agent | |
US2037974A (en) | Sulphonic acids of higher aliphatic ketones | |
US2098551A (en) | Reaction product of an ester-like wax and a base | |
US2088019A (en) | Secondary alkyl sulphates as wetting agents | |
US2320707A (en) | Surface active agent and the process of treating fibrous materials therewith | |
US2009346A (en) | Amido sulfonic acids and process for their preparation | |
US2346454A (en) | Surface active agent |