US3274205A - Quaternary ammonium derivatives of n-alkylcarbamoylethyl compounds - Google Patents
Quaternary ammonium derivatives of n-alkylcarbamoylethyl compounds Download PDFInfo
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- US3274205A US3274205A US399913A US39991364A US3274205A US 3274205 A US3274205 A US 3274205A US 399913 A US399913 A US 399913A US 39991364 A US39991364 A US 39991364A US 3274205 A US3274205 A US 3274205A
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- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
- C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
- C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
- C07D213/06—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom
- C07D213/16—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom containing only hydrogen and carbon atoms in addition to the ring nitrogen atom containing only one pyridine ring
- C07D213/20—Quaternary compounds thereof
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- 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
Definitions
- An object of the present invention is to provide quaternary ammonium derivatives of N-alkylacrylamide.
- a further object of this invention is to provide quaternary ammonium derivatives of N-alkylacrylarnides which are useful cationic surface active agents.
- Other objects include providing methods of inhibiting the growth of bacteria and nematodes.
- R is the residue of an olefin having from about 6 to 40 carbon atoms and A is an anion, for example, a halogen.
- the compounds of the present invention are readily prepared by methods known in the art. For example, one may start with N-alkylacrylamide wherein the alkyl group is R, and react with a pyridinium salt.
- the N-alkylacrylamide starting material may also be prepared by methods known in the art, for example, by means of the well known Ritter reaction of an olefin, acrylonitrile and strong sulfuric acid as et forth in US. Patent 2,573,673 to Ritter or Ritter et al., JACS 70, 4045048 (1948).
- Various improvements have been made on the Ritter reaction for the provision of higher yields of the N-alkylacrylamides. Among these are the disclosures of application Serial No. 282,553, filed May 23, 1963 (continuation-in-part of SN. 111,464, filed May 22, 1961, now abandoned), and application Serial No. 282,- 599, filed May 23, 1963 (continuation-in-part of SN. 111,465, filed May 22, 1961 now abandoned).
- the olefin residue R of the above formula is alkyl and is derived from olefin having about 6 and up to 40 carbon atoms, preferably from about 10 to 20 carbon atoms. These olefins are preferably further characterized as being predominantly straight chain, i.e., having a minimum of about 75% of straight chain materials. Suitable olefins are available from the petroleum industry.
- olefins As examples of such olefins, the following the illustrative: hexene-l, heptene-l, octene-l, decene-l, decene-2, decene- 3, decene-4, decene-S, undecene-l, undecene-2, undecene-3, undecene-4, undecene-S, dodecene-l, dodecene-2, dodecene-3, dodecene-4, dodecene-S, dodecene-6, tridecene-l, tridecene-2, tridecene-3, tridecene-4, tridecene-5, tridecene-6, tetradecene-l, tetradecene-2, tetradecene-3, tetradecene-4, tetradecene-S, tetradecen
- pentadecene-S pentadecene-6, pentadecene-7, hexadecene-l, hexadecene-Z, hexadecene-3, hexadecene-4, hexadecene-S, hexadecene-6, hexadecene-7, hexadecene-8, octadecene-l, octadecene-2, octadecene-3, octadecene-4, oc tadecene-S, octadecene-6, octadecene-7, octadecene-8, oc-
- telomers of propylene and butylene such as propylene tetramer, propylene hexamer, triisobutylene, tetraisobutylene and the like.
- the side chain isomers of any of the foregoing compounds are obviously included.
- these and other olefins may be employed singly or in combination with one or more of each other.
- the anion A may be any of the anions of pyridinium salts, both organic and inorganic. Included are salt forming radicals and materials such as the halogens, e.g., chlorine, bromine and iodine; sulfate, nitrate, phosphate and like radicals; and carboxylate radicals such as formate, acetate and anions of sulfonic acids and the like.
- halogens e.g., chlorine, bromine and iodine
- sulfate, nitrate, phosphate and like radicals e.g., sulfate, nitrate, phosphate and like radicals
- carboxylate radicals such as formate, acetate and anions of sulfonic acids and the like.
- anionic radicals can be introduced directly into the molecules; and, in the case of others, they can be made, for instance, by substitution for halogen in the cation-active surface active agents of the present in
- the quaternary ammonium compound of this invention may be prepared by reacting a pyridinium salt with an N-alkylacrylamide.
- This reaction primarily differs from similar reactions in the prior art by the presence of the alkyl group in N-alkylacrylamide.
- the instant compound may be prepared.
- a suitable reaction for this purpose is disclosed by R. Dowbenko, J. Org. Chem. 25, 1123-1127 (1960).
- the synthesis described therein shows the preparation of the pyridinium chloride salt of acrylamide.
- the essential difierence between this product and that of the instant invention is the absence of the olefin residue on the nitrogen atom of acrylamide.
- the presence of the olefin residue accounts for the surface activity as well as antibacterial and nematocidal activity of the present compound.
- the compounds of this invention may be applied directly and alone to the material to be treated or the compounds may be incorporated in conventional carriers or diluents and contacted with the microorganism.
- carrier or diluent is determined by the use of the composition as is the concentration of the active ingredient.
- an inert material such as talc, bentonite, kieselguhr, diatomaceous earth, and the like there can be prepared compositions suitable for admixture with or application to materials on which nematodes and bacteria feed.
- solutions of the compounds in organic solvents such as kerosene can be applied as sprays or impregnating baths or if desired with the use of pressure to facilitate penetration of the solution for treatment of various surfaces.
- Suitable formulations for application of the compound to articles subject to microbiological attack are also prepared by mixing the compounds with an emulsifying agent in the presence of organic solvents and then diluting with water to form an aqueous emulsion containing the compound.
- the degree of solubility of the compound in water and in organic solvents will be determined primarily by the carbon content and structure of R the olefin residue. Thus it will be apparent that compatibility as well as surface activity of the compound may be controlled by choice of olefins used to prepare the N-alkylacrylamide reactant. For example, products wherein the R group is in excess of about 12 carbon atoms will have lower water solubility and therefore will be useful in extracting metallic anions from aqueous solution into an organic solvent.
- Example 1 N-l-methylundecylacrylamide, 6.0 parts, obtained from the reaction of dodecene-l with acrylonitrile, was dissolved with 2.9 parts of pyridinium chloride in 30 parts by volume of methanol in a suitable reaction vessel. The mixture was refluxed for 4 hours at atmospheric pressure. Thereafiter, the solvent was stripped from the reaction mixture to give 8.1 parts of a brown, thick translucent gum in 91% yield. Upon standing, crystals were formed. Most of the oil was then dis-solved away by the use of chloroform and the mixture evaporated.
- the product was easily and completely water soluble and surface active as indicated by the foam produced in aqueous solution.
- the product was also soluble in organic solvents such as the lower alcohols and chloroform.
- Example 2 The compound of Example 1 was tested for antibacterial aotivity in a standard test substantially as follows.
- test tubes From a 1000 p.p.m. solution of the compound, a 1 ml. aliquot in 9 ml. deionized water was placed in each of three test tubes. The test tubes were then each inoculated with one drop of Staphylococcus aureaus, Aerobacter aerogenes and Xanthomonas resicatoria, respectively. The test tubes were allowed to stand 24 hours at room temperature and then 1 ml. of a solution containing peptone broth and 1% dextrose was added to each of the test tubes. The test tubes were then incubated at 37 C. for 24 hours and thereafter observed for evidence of bacterial growth.
- Example 3 The compound of Example 1 was also tested for nematocidal activity in a standard activity test substantially as follows.
- Example 1 To 4 ml. of 0.1% solution of the compound of Example 1 in a stoppered vial was added sutficient cultured vinegar eel worm nematode to obtain a 100 p.p.m. concentration. The vial was then tumbled to provide intimate contact of chemical and organism. After hours rotation on the tumbler, the eel worms were examined and percent mortality recorded. The compound of Example 1 showed good activity.
- Example 4 By essentially the same procedure as in Example 1 the following compounds are prepared:
- n-dodecylamine n-dodecylamine
- a suitable HCl acceptor e.g., pyridine
- the reaction mixture is maintained cold, about 10 C., and the reaction proceeds spontaneously.
- pyridinium chloride is filtered off and the reaction product distilled to obtain N-n-dodecylacrylamide.
- This intermediate is then reacted with a pyridinium salt, e.g., pyridinium bromide, substantially as in Example 1, to form l- 2- (n-dodecylcarbam'oyl) ethyl] pyridinium bromide.
- Example 6 By essentially the same procedure as in Example 5, the following compounds are made:
- R is the residue of an olefin having from about 6 to 40 carbon atoms and A is an anion.
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- Agricultural Chemicals And Associated Chemicals (AREA)
- Pyridine Compounds (AREA)
Description
United States Patent Ofifice 3,274,205 Patented Sept. 20, 1966 3,274,205 QUATERNARY AMMONIUM DERIVATIVES OF N-ALKYLCARBAMOYLETHY L COMPOUNDS Norbert M. Bikales, Livingston, N.J., assignor to American Cyanamid Company, Stamford, Conn., 21 corporation of Maine N Drawing. Filed Sept. 28, 1964, Ser. No. 399,913 2 Claims. (Cl. 260-295) This invention relates to quaternary ammonium derivatives of N-alkylcarbamoylethyl compounds. This invention also relates to novel cationic surface active compounds useful for bactericidal, nematocidal, antistatic, emulsifying, foam modifying, and various other purposes for which cationic surface active agents have been useful.
An object of the present invention is to provide quaternary ammonium derivatives of N-alkylacrylamide.
A further object of this invention is to provide quaternary ammonium derivatives of N-alkylacrylarnides which are useful cationic surface active agents.
Other objects include providing methods of inhibiting the growth of bacteria and nematodes.
These and other objects and advantages of the present invention will become apparent from the detailed description which follows.
In accordance with the present invention there is provided a quaternary ammonium compound of the formula:
wherein R is the residue of an olefin having from about 6 to 40 carbon atoms and A is an anion, for example, a halogen.
The compounds of the present invention are readily prepared by methods known in the art. For example, one may start with N-alkylacrylamide wherein the alkyl group is R, and react with a pyridinium salt.
The N-alkylacrylamide starting material may also be prepared by methods known in the art, for example, by means of the well known Ritter reaction of an olefin, acrylonitrile and strong sulfuric acid as et forth in US. Patent 2,573,673 to Ritter or Ritter et al., JACS 70, 4045048 (1948). Various improvements have been made on the Ritter reaction for the provision of higher yields of the N-alkylacrylamides. Among these are the disclosures of application Serial No. 282,553, filed May 23, 1963 (continuation-in-part of SN. 111,464, filed May 22, 1961, now abandoned), and application Serial No. 282,- 599, filed May 23, 1963 (continuation-in-part of SN. 111,465, filed May 22, 1961 now abandoned).
The olefin residue R of the above formula is alkyl and is derived from olefin having about 6 and up to 40 carbon atoms, preferably from about 10 to 20 carbon atoms. These olefins are preferably further characterized as being predominantly straight chain, i.e., having a minimum of about 75% of straight chain materials. Suitable olefins are available from the petroleum industry. As examples of such olefins, the following the illustrative: hexene-l, heptene-l, octene-l, decene-l, decene-2, decene- 3, decene-4, decene-S, undecene-l, undecene-2, undecene-3, undecene-4, undecene-S, dodecene-l, dodecene-2, dodecene-3, dodecene-4, dodecene-S, dodecene-6, tridecene-l, tridecene-2, tridecene-3, tridecene-4, tridecene-5, tridecene-6, tetradecene-l, tetradecene-2, tetradecene-3, tetradecene-4, tetradecene-S, tetradecene-6, tetradecene-7, pentadecene-l, pentadecene-Z, pentadecene-3, pentadecene-4,
pentadecene-S, pentadecene-6, pentadecene-7, hexadecene-l, hexadecene-Z, hexadecene-3, hexadecene-4, hexadecene-S, hexadecene-6, hexadecene-7, hexadecene-8, octadecene-l, octadecene-2, octadecene-3, octadecene-4, oc tadecene-S, octadecene-6, octadecene-7, octadecene-8, oc-
tadecene 9, telomers of propylene and butylene such as propylene tetramer, propylene hexamer, triisobutylene, tetraisobutylene and the like. The side chain isomers of any of the foregoing compounds are obviously included. In the preparation of Naalkylacrylamide, these and other olefins may be employed singly or in combination with one or more of each other.
The anion A may be any of the anions of pyridinium salts, both organic and inorganic. Included are salt forming radicals and materials such as the halogens, e.g., chlorine, bromine and iodine; sulfate, nitrate, phosphate and like radicals; and carboxylate radicals such as formate, acetate and anions of sulfonic acids and the like. Various of said anionic radicals can be introduced directly into the molecules; and, in the case of others, they can be made, for instance, by substitution for halogen in the cation-active surface active agents of the present inven tion by known techniques as, for instance, by metathesis procedures.
As mentioned above the quaternary ammonium compound of this invention may be prepared by reacting a pyridinium salt with an N-alkylacrylamide. This reaction primarily differs from similar reactions in the prior art by the presence of the alkyl group in N-alkylacrylamide. Thus, by substituting the requisite N-alkylacrylamide in the prior art processes, the instant compound may be prepared. A suitable reaction for this purpose is disclosed by R. Dowbenko, J. Org. Chem. 25, 1123-1127 (1960). The synthesis described therein shows the preparation of the pyridinium chloride salt of acrylamide. The essential difierence between this product and that of the instant invention is the absence of the olefin residue on the nitrogen atom of acrylamide. As will be shown hereinafter, the presence of the olefin residue accounts for the surface activity as well as antibacterial and nematocidal activity of the present compound.
As antibacterial and nematocidal agents, the compounds of this invention may be applied directly and alone to the material to be treated or the compounds may be incorporated in conventional carriers or diluents and contacted with the microorganism. The choice of carrier or diluent is determined by the use of the composition as is the concentration of the active ingredient. Thus by admixture with an inert material such as talc, bentonite, kieselguhr, diatomaceous earth, and the like there can be prepared compositions suitable for admixture with or application to materials on which nematodes and bacteria feed. Also solutions of the compounds in organic solvents such as kerosene can be applied as sprays or impregnating baths or if desired with the use of pressure to facilitate penetration of the solution for treatment of various surfaces. Suitable formulations for application of the compound to articles subject to microbiological attack are also prepared by mixing the compounds with an emulsifying agent in the presence of organic solvents and then diluting with water to form an aqueous emulsion containing the compound.
The degree of solubility of the compound in water and in organic solvents will be determined primarily by the carbon content and structure of R the olefin residue. Thus it will be apparent that compatibility as well as surface activity of the compound may be controlled by choice of olefins used to prepare the N-alkylacrylamide reactant. For example, products wherein the R group is in excess of about 12 carbon atoms will have lower water solubility and therefore will be useful in extracting metallic anions from aqueous solution into an organic solvent.
In order that the present invention may be more completely understood, the following examples are given in which all parts are parts by weight unless otherwise specified. These examples are set forth primarily for the purpose of illustration and any specific enumeration of 3 detail contained therein should not be interpreted as a limitation on the case except where indicated in the appended claims.
Example 1 N-l-methylundecylacrylamide, 6.0 parts, obtained from the reaction of dodecene-l with acrylonitrile, was dissolved with 2.9 parts of pyridinium chloride in 30 parts by volume of methanol in a suitable reaction vessel. The mixture was refluxed for 4 hours at atmospheric pressure. Thereafiter, the solvent was stripped from the reaction mixture to give 8.1 parts of a brown, thick translucent gum in 91% yield. Upon standing, crystals were formed. Most of the oil was then dis-solved away by the use of chloroform and the mixture evaporated. The infrared spectrum indicated the product to be mainly 1 {2 [(1 methylundecyl)carbamoyl]ethyl}pyridinium chloride. The product was easily and completely water soluble and surface active as indicated by the foam produced in aqueous solution. The product was also soluble in organic solvents such as the lower alcohols and chloroform.
Example 2 The compound of Example 1 was tested for antibacterial aotivity in a standard test substantially as follows.
From a 1000 p.p.m. solution of the compound, a 1 ml. aliquot in 9 ml. deionized water was placed in each of three test tubes. The test tubes were then each inoculated with one drop of Staphylococcus aureaus, Aerobacter aerogenes and Xanthomonas resicatoria, respectively. The test tubes were allowed to stand 24 hours at room temperature and then 1 ml. of a solution containing peptone broth and 1% dextrose was added to each of the test tubes. The test tubes were then incubated at 37 C. for 24 hours and thereafter observed for evidence of bacterial growth. The clarity of the solutions in the test tubes indicated complete inhibition of growth of the Aerobacter aerogenes and Xanthomonas resicatOria species and substantial kill of the Staphylococcus aureus species. As contrasted with this activity, the compound lacking the olefin residue, namely, N-(Z-carbamoylethyl)pyridinium chloride, showed substantially no activity in kill or in inhibiting the growth of these bacteria.
Example 3 The compound of Example 1 was also tested for nematocidal activity in a standard activity test substantially as follows.
To 4 ml. of 0.1% solution of the compound of Example 1 in a stoppered vial was added sutficient cultured vinegar eel worm nematode to obtain a 100 p.p.m. concentration. The vial was then tumbled to provide intimate contact of chemical and organism. After hours rotation on the tumbler, the eel worms were examined and percent mortality recorded. The compound of Example 1 showed good activity.
4 Example 4 By essentially the same procedure as in Example 1 the following compounds are prepared:
1-{ 2- l-methylheptyl) carbamoyl] ethyl}pyridinium chloride 1- 2- l-methylnonyl) carbamoyl] ethyl}pyridinium chloride 1-{2-[ 1 1 -dimethylundecyl) carbamoyl] ethyl} pyridinium chloride 1- {2- l-methyltetradecyl) carbamoyl] ethyl}pyridinium chloride 1-{2- l-methylnonadecyl) carb amoyl] ethyl} pyridinium chloride Example 5 The following procedure is employed to prepare quaternary ammonium salts of this invention wherein R is straight chain alkyl.
In a suitable reaction vessel acrylyl chloride is added to n-dodecylamine and a suitable HCl acceptor, e.g., pyridine, in equimolar proportions in methanol. The reaction mixture is maintained cold, about 10 C., and the reaction proceeds spontaneously. On completion of reaction, pyridinium chloride is filtered off and the reaction product distilled to obtain N-n-dodecylacrylamide. This intermediate is then reacted with a pyridinium salt, e.g., pyridinium bromide, substantially as in Example 1, to form l- 2- (n-dodecylcarbam'oyl) ethyl] pyridinium bromide.
Example 6 By essentially the same procedure as in Example 5, the following compounds are made:
l- 2- n-hexylcarbamoyl ethyl] pyridinium bromide 1- 2- (n-decylcarbamoyl ethyl] pyridinium bromide 1- 2- n-tetra decylcarbamoyl ethyl] pyridinium bromide 1- 2- (n-octade cylcarbamoyl ethyl] pyridinium bromide 1- 2- (n-eicosylcarbamoyl ethyl] pyridinium bromide.
I claim: 1. A quaternary ammonium compound of the formula:
wherein R is the residue of an olefin having from about 6 to 40 carbon atoms and A is an anion.
2. 1 {2 [(1 methylundecyl) carbamoyl]ethyl}pyridinium chloride.
References Cited by the Examiner WALTER A. MODANCE, Primary Examiner.
ALAN L. ROTMAN, Assistant Examiner.
Claims (1)
1. A QUATERNARY AMMONIUM COMPOUND OF THE FORMULA:
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US399913A US3274205A (en) | 1964-09-28 | 1964-09-28 | Quaternary ammonium derivatives of n-alkylcarbamoylethyl compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
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| US399913A US3274205A (en) | 1964-09-28 | 1964-09-28 | Quaternary ammonium derivatives of n-alkylcarbamoylethyl compounds |
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| US3274205A true US3274205A (en) | 1966-09-20 |
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| US399913A Expired - Lifetime US3274205A (en) | 1964-09-28 | 1964-09-28 | Quaternary ammonium derivatives of n-alkylcarbamoylethyl compounds |
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Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150044366A1 (en) * | 2012-04-19 | 2015-02-12 | Saltworks Technologies, Inc. | Resilient ion exchange membranes prepared by polymerizing ionic surfactant monomers |
| US20150232627A1 (en) * | 2012-10-19 | 2015-08-20 | Saltworks Technologies Inc. | Acrylamide-Based Crosslinking Monomers, Their Preparation, And Uses Thereof |
Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2219287A (en) * | 1938-01-22 | 1940-10-29 | Tobacco By Products And Chemic | Insecticide and process of making the same |
| US2219847A (en) * | 1938-08-11 | 1940-10-29 | Preston P Purdum | Pyridine composition for treatment of blue mold in plants and seed beds |
| US2344934A (en) * | 1943-02-12 | 1944-03-21 | American Cyanamid Co | Quaternary nitrogen condensation products of methylol urea ethers |
| US2487382A (en) * | 1945-04-18 | 1949-11-08 | Ciba Ltd | Urea derivatives and process of making same |
-
1964
- 1964-09-28 US US399913A patent/US3274205A/en not_active Expired - Lifetime
Patent Citations (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2219287A (en) * | 1938-01-22 | 1940-10-29 | Tobacco By Products And Chemic | Insecticide and process of making the same |
| US2219847A (en) * | 1938-08-11 | 1940-10-29 | Preston P Purdum | Pyridine composition for treatment of blue mold in plants and seed beds |
| US2344934A (en) * | 1943-02-12 | 1944-03-21 | American Cyanamid Co | Quaternary nitrogen condensation products of methylol urea ethers |
| US2487382A (en) * | 1945-04-18 | 1949-11-08 | Ciba Ltd | Urea derivatives and process of making same |
Cited By (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20150044366A1 (en) * | 2012-04-19 | 2015-02-12 | Saltworks Technologies, Inc. | Resilient ion exchange membranes prepared by polymerizing ionic surfactant monomers |
| US9199203B2 (en) * | 2012-04-19 | 2015-12-01 | Saltworks Technologies, Inc. | Resilient ion exchange membranes prepared by polymerizing ionic surfactant monomers |
| US20160030894A1 (en) * | 2012-04-19 | 2016-02-04 | Saltworks Technologies, Inc. | Resilient Anion Exchange Membranes Prepared By Polymerizing A Composition |
| US9636642B2 (en) * | 2012-04-19 | 2017-05-02 | Saltworks Technologies Inc. | Resilient anion exchange membranes prepared by polymerizing a composition |
| US20150232627A1 (en) * | 2012-10-19 | 2015-08-20 | Saltworks Technologies Inc. | Acrylamide-Based Crosslinking Monomers, Their Preparation, And Uses Thereof |
| US9416239B2 (en) * | 2012-10-19 | 2016-08-16 | Saltworks Technologies Inc. | Acrylamide-based crosslinking monomers, their preparation, and uses thereof |
| US20160318013A1 (en) * | 2012-10-19 | 2016-11-03 | Saltworks Technologies Inc. | Acrylamide-Based Crosslinking Monomers, Their Preparation, And Uses Thereof |
| US9662647B2 (en) * | 2012-10-19 | 2017-05-30 | Saltworks Technologies Inc. | Acrylamide-based crosslinking monomers, their preparation, and uses thereof |
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