US2636036A - Aromatic nitrogen compounds - Google Patents
Aromatic nitrogen compounds Download PDFInfo
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- US2636036A US2636036A US719139A US71913946A US2636036A US 2636036 A US2636036 A US 2636036A US 719139 A US719139 A US 719139A US 71913946 A US71913946 A US 71913946A US 2636036 A US2636036 A US 2636036A
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- United States
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- compounds
- phenethyl
- parts
- weight
- bromide
- Prior art date
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- Expired - Lifetime
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- -1 Aromatic nitrogen compounds Chemical class 0.000 title description 27
- 229910017464 nitrogen compound Inorganic materials 0.000 title description 2
- 150000001875 compounds Chemical class 0.000 claims description 23
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 8
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 6
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 5
- 125000000217 alkyl group Chemical group 0.000 description 4
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Chemical compound BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 4
- 238000000034 method Methods 0.000 description 4
- 229910052757 nitrogen Inorganic materials 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- HCHKCACWOHOZIP-UHFFFAOYSA-N Zinc Chemical compound [Zn] HCHKCACWOHOZIP-UHFFFAOYSA-N 0.000 description 3
- 229910021529 ammonia Inorganic materials 0.000 description 3
- 229910052794 bromium Inorganic materials 0.000 description 3
- 238000006243 chemical reaction Methods 0.000 description 3
- 125000005843 halogen group Chemical group 0.000 description 3
- 239000000203 mixture Substances 0.000 description 3
- 125000004433 nitrogen atom Chemical group N* 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 description 3
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 239000004215 Carbon black (E152) Substances 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- YZCKVEUIGOORGS-UHFFFAOYSA-N Hydrogen atom Chemical compound [H] YZCKVEUIGOORGS-UHFFFAOYSA-N 0.000 description 2
- YNAVUWVOSKDBBP-UHFFFAOYSA-N Morpholine Chemical compound C1COCCN1 YNAVUWVOSKDBBP-UHFFFAOYSA-N 0.000 description 2
- SMWDFEZZVXVKRB-UHFFFAOYSA-N Quinoline Chemical compound N1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-N 0.000 description 2
- WGQKYBSKWIADBV-UHFFFAOYSA-N benzylamine Chemical compound NCC1=CC=CC=C1 WGQKYBSKWIADBV-UHFFFAOYSA-N 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- 238000010790 dilution Methods 0.000 description 2
- 239000012895 dilution Substances 0.000 description 2
- 229930195733 hydrocarbon Natural products 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- AWJUIBRHMBBTKR-UHFFFAOYSA-N isoquinoline Chemical compound C1=NC=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-N 0.000 description 2
- HZVOZRGWRWCICA-UHFFFAOYSA-N methanediyl Chemical compound [CH2] HZVOZRGWRWCICA-UHFFFAOYSA-N 0.000 description 2
- 239000003208 petroleum Substances 0.000 description 2
- 239000011541 reaction mixture Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000004448 titration Methods 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- BSKHPKMHTQYZBB-UHFFFAOYSA-N 2-methylpyridine Chemical compound CC1=CC=CC=N1 BSKHPKMHTQYZBB-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 238000005727 Friedel-Crafts reaction Methods 0.000 description 1
- 230000010933 acylation Effects 0.000 description 1
- 238000005917 acylation reaction Methods 0.000 description 1
- 150000001350 alkyl halides Chemical class 0.000 description 1
- 150000001450 anions Chemical group 0.000 description 1
- 150000001555 benzenes Chemical class 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- 150000001721 carbon Chemical group 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000003638 chemical reducing agent Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 125000001309 chloro group Chemical group Cl* 0.000 description 1
- HPNMFZURTQLUMO-UHFFFAOYSA-N diethylamine Chemical compound CCNCC HPNMFZURTQLUMO-UHFFFAOYSA-N 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 230000002070 germicidal effect Effects 0.000 description 1
- 125000000623 heterocyclic group Chemical group 0.000 description 1
- SMWDFEZZVXVKRB-UHFFFAOYSA-O hydron;quinoline Chemical compound [NH+]1=CC=CC2=CC=CC=C21 SMWDFEZZVXVKRB-UHFFFAOYSA-O 0.000 description 1
- AWJUIBRHMBBTKR-UHFFFAOYSA-O isoquinolin-2-ium Chemical compound C1=[NH+]C=CC2=CC=CC=C21 AWJUIBRHMBBTKR-UHFFFAOYSA-O 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 150000002830 nitrogen compounds Chemical class 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
- 125000003884 phenylalkyl group Chemical group 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-O pyridinium Chemical compound C1=CC=[NH+]C=C1 JUJWROOIHBZHMG-UHFFFAOYSA-O 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
- 239000011701 zinc Substances 0.000 description 1
- 229910052725 zinc Inorganic materials 0.000 description 1
Classifications
-
- 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
-
- 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
- Our invention relates to novel organic compounds particularly valuable for use as surface active agents. and as germicides.
- the compounds are characterized in that they contain at least two side groups in para relation on a. benzene nucleus, one of these side groups being an alkyl group containing six to eighteen carbon atoms, the other being a group comprising an alkyl portion terminating in an ionizing, basic nitrogen atom.
- R is an alkyl radical containing six to eighteen carbon atoms
- n is an integer greater than 1
- X is a halogen atom, most suitably a bromine or chlorine atom
- R1, R2 and R3 are hydrogen or monovalent hydrocarbon radicals and in which the circle (Formula. I) indicates that the nitrogen atom is part of a heterocyclic ring system.
- hexyl phenethyl pyridinium bromide dodecyl phenethyl pyridinium bromide, octyl phenethyl pyridinium bromide, lauryl phenylpropyl quinolinium chloride, undecyl phenylbutyl quinolinium chloride, hexadecyl phenylpropyl picolinium bromide, octadecyl phenethyl isoquinolinium bromide, heptyl phenethyl ammonium chloride, octadecyl phenylpropyl ammonium bromide, undecyl phenylbutyl trimethyl ammonium bromide, hexyl phenethyl dimethyl ammonium chloride, nonyl phenylpropyl benzyl ammonium bromide, the chlorides
- our invention embraces compounds in which the nitrogen atom forming part of one of the two necessary groups attached to the benzene nucleus has a valency of three.
- Example II 78 parts by weight of dodecyl phenethyl bromide were mixed with 20 parts by weight of pyridine and the mixture kept at 140 C. for three hours, whereafterit was extracted with petroleum ether. The product was soluble in water. Its killing dilution was 123,000 against Eberthella typhosa at 20 C. Titration for bromine demonstrated that the chemical formula was that of dodecyl phenethyl pyridinium bromide.
- Example III 20 parts by weight of octyl phenethyl bromide were mixed with 5 parts by weight of pyridine and the mixture kept at 140 C. for one hour. After extraction with petroleum ether, the titration for bromine demonstrated that the product was octyl phenethyl pyridinium bromide. Its killing dilution was 1:1,600 against Eberthella typhosa at 20 C.
- Example IV 6 parts by weight of lauroyl phenethyl diethylamine was treated for six hours with a mixture containing 40 parts by weight of ethyleneglycol diethyl ether, 150 parts concentrated aqueous HCl, and 30 parts by weight of zinc granules. Gaseous HCl was bubbled through the well-agitated reaction mixture for six hours. After this, the reaction mixture was mixed with aqueous caustic soda until it became alkaline and was extracted with ether. Evaporation of the ether yields dodecyl phenethyl diethyl amine;
- Example V 4 parts by weight ofcaproyl phenethyl diethyl amine weremixed with 60 parts by weight of ethyl alcohol, 150 parts by weight of concentrated hydrochloric acid and 30'parts by weight of zinc granules. The reaction is carried out as in Example IV. The reaction product is distilled under 4 mm. Hg pressure at 154-157 C. yielding hexyl phenethyl diethyl amine.
- R represents an alkyl group containing from 6 to 18 carbon atoms
- n is an integer greater than 1
- A is a quaternary ammonium radical of the class consisting of pyridinium, quinolinium, picolinium, isoquinolinium and the morpholinium radicals, the nitrogen of the A radical being linked directly to the terminal carbon of the (CI-I2) group and also to a halogen atom.
- R is an alkyl radical containing at least 7 carbon atoms
- n is an integer greater than one.
- N ERI is a tertiary amine
- X is an anion.
Landscapes
- Chemical & Material Sciences (AREA)
- Organic Chemistry (AREA)
- Pyridine Compounds (AREA)
Description
Patented Apr. 21, 1953 UNITED STATES ARQMATIC NITROGEN COMPOUNDS Adrien S. Du Bois, Jersey City, N. 3., and Emery I. Valko, New York, N. Y., assignors to Onyx Oil & Chemical Company, Jersey City, N. J... a corporation of Delaware No Drawing. Continuation of application Serial,
No. 564,548, November 21, 1944. This application December 28, 1946, Serial No. 719,139
9 Claims. 1
Our invention relates to novel organic compounds particularly valuable for use as surface active agents. and as germicides. The compounds are characterized in that they contain at least two side groups in para relation on a. benzene nucleus, one of these side groups being an alkyl group containing six to eighteen carbon atoms, the other being a group comprising an alkyl portion terminating in an ionizing, basic nitrogen atom.
This application is a continuation of our application, Serial Number 564,548, filed November 21, 1944, dealing with the production of alkoyl phenyl alkyl halides.
The preferred compounds of our present invention conform to the formulae in which R is an alkyl radical containing six to eighteen carbon atoms, n is an integer greater than 1, X is a halogen atom, most suitably a bromine or chlorine atom, R1, R2 and R3 are hydrogen or monovalent hydrocarbon radicals and in which the circle (Formula. I) indicates that the nitrogen atom is part of a heterocyclic ring system. As exemplary of such compounds may be mentioned: hexyl phenethyl pyridinium bromide, dodecyl phenethyl pyridinium bromide, octyl phenethyl pyridinium bromide, lauryl phenylpropyl quinolinium chloride, undecyl phenylbutyl quinolinium chloride, hexadecyl phenylpropyl picolinium bromide, octadecyl phenethyl isoquinolinium bromide, heptyl phenethyl ammonium chloride, octadecyl phenylpropyl ammonium bromide, undecyl phenylbutyl trimethyl ammonium bromide, hexyl phenethyl dimethyl ammonium chloride, nonyl phenylpropyl benzyl ammonium bromide, the chlorides and bromides of N-hexa phenethyl morpholine, etc.
In addition to compounds meeting the type formula, supra, our invention embraces compounds in which the nitrogen atom forming part of one of the two necessary groups attached to the benzene nucleus has a valency of three.
Although other methods of preparation are possible, We usually prepare. our preferred compounds by one 01 twomethods;
(a) Reduction of compounds of the formulae- Ra. X
in which R, n, etc. have thesame significance as in the preceding formulae.
(b) Reaction of compounds of the formula in which R, 12, etc. have the same significance with ammonia or with amines, such as those indicated by the list of representative compounds above, e, g. pyridine, quinoline, isoquinoline, diethylamine, trimethylamine, benzylamine; morpholine, etc.
We have found that the reduction procedure, which results in the conversion of the carbonyl radical to a methylene radical with the result that the compound becomes more surface active, proceeds with particular advantage when nascent hydrogen produced by contacting metallic zinc, preferably in granulated form, with concentrated aqueous hydrochloric acid is employed as the reducing agent.
The carbonyl-containing compounds subjected to reduction are readily prepared, in accordance with our copending application, Serial No. 719,140, filed December 28, 1946, by reacting the corresponding allgoyl pheny alkyl halide,
VIi
no o Qc Hax produced as by the acylation of the corresponding halogenated-alkyl phenyl compounds described therein in the presence of a Friedel- Crafts catalyst. with an amine. In place of the amine, ammonia may be used, the choice as between ammonia and, amines and as between amines being determined, of course, by the product desired upon the reduction;
The compounds of Formula V used-in method (1)), supra, are advantageously produced according to our copending application, Serial No. 719,138, filed. December 28, 1946, by reduction of the corresponding alkoyl compounds, i. e. compounds meetign Formula. VI.
Compounds, within. the. scope of our invention,
but which do not meehthe time iormulaey first,
given herein, are prepared when compounds of the formula VII in which R, R1, R2, and n have the same significance as heretofore are subjected to'treatment, as with nascent hydrogen, preferably used in the presence of a solvent, ethylene glycol diethyl ether, for example, to convert the carbonyl radical to a methylene radical. Dodecyl phenethyl diethyl amine and hexyl phenethyl diethyl amine are exemplary of compounds we produce by this method.
The following examples are submitted by way of illustrating practices of our invention.
Example I Example II 78 parts by weight of dodecyl phenethyl bromide were mixed with 20 parts by weight of pyridine and the mixture kept at 140 C. for three hours, whereafterit was extracted with petroleum ether. The product was soluble in water. Its killing dilution was 123,000 against Eberthella typhosa at 20 C. Titration for bromine demonstrated that the chemical formula was that of dodecyl phenethyl pyridinium bromide.
Example III 20 parts by weight of octyl phenethyl bromide were mixed with 5 parts by weight of pyridine and the mixture kept at 140 C. for one hour. After extraction with petroleum ether, the titration for bromine demonstrated that the product was octyl phenethyl pyridinium bromide. Its killing dilution was 1:1,600 against Eberthella typhosa at 20 C.
Example IV 6 parts by weight of lauroyl phenethyl diethylamine was treated for six hours with a mixture containing 40 parts by weight of ethyleneglycol diethyl ether, 150 parts concentrated aqueous HCl, and 30 parts by weight of zinc granules. Gaseous HCl was bubbled through the well-agitated reaction mixture for six hours. After this, the reaction mixture was mixed with aqueous caustic soda until it became alkaline and was extracted with ether. Evaporation of the ether yields dodecyl phenethyl diethyl amine;
Example V 4 parts by weight ofcaproyl phenethyl diethyl amine weremixed with 60 parts by weight of ethyl alcohol, 150 parts by weight of concentrated hydrochloric acid and 30'parts by weight of zinc granules. The reaction is carried out as in Example IV. The reaction product is distilled under 4 mm. Hg pressure at 154-157 C. yielding hexyl phenethyl diethyl amine.
We claim: 1. p-Hexyl phenethyl pyridinium bromide. 2. p-Dodecyl phenethyl pyridinium bromide. 3. p-Octyl phenethyl pyridinium bromide 4. Organic chemical compounds conforming to the formula in which R represents an alkyl group containing from 6 to 18 carbon atoms, n represents an integer greater than 1, and R1, R2, and R3 are selected from the group consisting of hydrogen and monovalent hydrocarbon radicals, in which N is linked directly to the terminal carbon atom of the (CHzM group, and in which X represents a halogen atom.
6. Organic chemical compounds conforming to the formula in which R represents an alkyl group containing from 6 to 18 carbon atoms, n is an integer greater than 1 and A is a quaternary ammonium radical of the class consisting of pyridinium, quinolinium, picolinium, isoquinolinium and the morpholinium radicals, the nitrogen of the A radical being linked directly to the terminal carbon of the (CI-I2) group and also to a halogen atom.
7.'The organic chemical compounds of claim 4 in which A is the trimethyl ammonium chloride radical.
8. The organic chemical compounds of claim 4 in which A is the triethyl ammonium chloride radical.
9. A compound represented by the following formula:
where R is an alkyl radical containing at least 7 carbon atoms, n is an integer greater than one. N ERI is a tertiary amine, X is an anion.
ADRIEN S. DU BOIS, EMERY I. VALKO.
I References Cited in the file of this patent UNITED STATES PATENTS
Claims (1)
- 9. A COMPOUND REPRESENTED BY THE FOLLOWING FORMULA
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US719139A US2636036A (en) | 1946-12-28 | 1946-12-28 | Aromatic nitrogen compounds |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US719139A US2636036A (en) | 1946-12-28 | 1946-12-28 | Aromatic nitrogen compounds |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2636036A true US2636036A (en) | 1953-04-21 |
Family
ID=24888890
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US719139A Expired - Lifetime US2636036A (en) | 1946-12-28 | 1946-12-28 | Aromatic nitrogen compounds |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2636036A (en) |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689789A (en) * | 1951-08-25 | 1954-09-21 | Monsanto Chemicals | Quaternary nitrogen compound herbicides |
| US2993050A (en) * | 1955-11-22 | 1961-07-18 | Exxon Research Engineering Co | Telomers of hydrocarbon olefins and methyl-containing cyclic organic compounds |
| US3445518A (en) * | 1966-05-06 | 1969-05-20 | Warner Lambert Pharmaceutical | P-acylphenylethylamines |
| US4705553A (en) * | 1984-06-12 | 1987-11-10 | Basf Aktiengesellschaft | Method of reducing plant growth height using phenylalkylmorpholines |
Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB499203A (en) * | 1937-07-14 | 1939-01-16 | Ig Farbenindustrie Ag | The manufacture of wetting agents |
| CH217134A (en) * | 1938-11-25 | 1941-09-30 | Geigy Ag J R | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. |
| US2271707A (en) * | 1937-06-24 | 1942-02-03 | Gen Aniline & Film Corp | Wetting agent |
| US2276587A (en) * | 1938-11-25 | 1942-03-17 | Geigy Ag J R | Water-soluble, high molecular alpha-substituted aralkyl amines and their manufacture |
| US2314111A (en) * | 1940-10-29 | 1943-03-16 | Standard Oil Co | Coating mineral aggregates |
-
1946
- 1946-12-28 US US719139A patent/US2636036A/en not_active Expired - Lifetime
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2271707A (en) * | 1937-06-24 | 1942-02-03 | Gen Aniline & Film Corp | Wetting agent |
| GB499203A (en) * | 1937-07-14 | 1939-01-16 | Ig Farbenindustrie Ag | The manufacture of wetting agents |
| CH217134A (en) * | 1938-11-25 | 1941-09-30 | Geigy Ag J R | Process for the production of a water-soluble, higher molecular weight, α-substituted benzylamine derivative. |
| US2276587A (en) * | 1938-11-25 | 1942-03-17 | Geigy Ag J R | Water-soluble, high molecular alpha-substituted aralkyl amines and their manufacture |
| US2314111A (en) * | 1940-10-29 | 1943-03-16 | Standard Oil Co | Coating mineral aggregates |
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2689789A (en) * | 1951-08-25 | 1954-09-21 | Monsanto Chemicals | Quaternary nitrogen compound herbicides |
| US2993050A (en) * | 1955-11-22 | 1961-07-18 | Exxon Research Engineering Co | Telomers of hydrocarbon olefins and methyl-containing cyclic organic compounds |
| US3445518A (en) * | 1966-05-06 | 1969-05-20 | Warner Lambert Pharmaceutical | P-acylphenylethylamines |
| US4705553A (en) * | 1984-06-12 | 1987-11-10 | Basf Aktiengesellschaft | Method of reducing plant growth height using phenylalkylmorpholines |
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