US2764603A - Alkylaminoalkyl-perfluoroamides - Google Patents
Alkylaminoalkyl-perfluoroamides Download PDFInfo
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- US2764603A US2764603A US424789A US42478954A US2764603A US 2764603 A US2764603 A US 2764603A US 424789 A US424789 A US 424789A US 42478954 A US42478954 A US 42478954A US 2764603 A US2764603 A US 2764603A
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- United States
- Prior art keywords
- compounds
- oils
- waxes
- dynes
- fluorocarbon
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- Expired - Lifetime
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- 150000001875 compounds Chemical class 0.000 description 23
- 239000003921 oil Substances 0.000 description 16
- 235000019198 oils Nutrition 0.000 description 16
- 239000001993 wax Substances 0.000 description 12
- NBVXSUQYWXRMNV-UHFFFAOYSA-N fluoromethane Chemical compound FC NBVXSUQYWXRMNV-UHFFFAOYSA-N 0.000 description 8
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 8
- 229910052757 nitrogen Inorganic materials 0.000 description 7
- -1 polymethylene chain Polymers 0.000 description 7
- 125000004433 nitrogen atom Chemical group N* 0.000 description 6
- 238000009835 boiling Methods 0.000 description 4
- 229910052799 carbon Inorganic materials 0.000 description 4
- 229930195733 hydrocarbon Natural products 0.000 description 4
- 125000005010 perfluoroalkyl group Chemical group 0.000 description 4
- 239000004094 surface-active agent Substances 0.000 description 4
- 239000004215 Carbon black (E152) Substances 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 239000003795 chemical substances by application Substances 0.000 description 3
- 230000000694 effects Effects 0.000 description 3
- 150000002430 hydrocarbons Chemical class 0.000 description 3
- 230000002940 repellent Effects 0.000 description 3
- 239000005871 repellent Substances 0.000 description 3
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 238000006243 chemical reaction Methods 0.000 description 2
- 230000007423 decrease Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 239000011737 fluorine Substances 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 239000001257 hydrogen Substances 0.000 description 2
- 229910052739 hydrogen Inorganic materials 0.000 description 2
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 239000002480 mineral oil Substances 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000007858 starting material Substances 0.000 description 2
- WKVZMKDXJFCMMD-UVWUDEKDSA-L (5ar,8ar,9r)-5-[[(2r,4ar,6r,7r,8r,8as)-7,8-dihydroxy-2-methyl-4,4a,6,7,8,8a-hexahydropyrano[3,2-d][1,3]dioxin-6-yl]oxy]-9-(4-hydroxy-3,5-dimethoxyphenyl)-5a,6,8a,9-tetrahydro-5h-[2]benzofuro[6,5-f][1,3]benzodioxol-8-one;azanide;n,3-bis(2-chloroethyl)-2-ox Chemical compound [NH2-].[NH2-].Cl[Pt+2]Cl.ClCCNP1(=O)OCCCN1CCCl.COC1=C(O)C(OC)=CC([C@@H]2C3=CC=4OCOC=4C=C3C(O[C@H]3[C@@H]([C@@H](O)[C@@H]4O[C@H](C)OC[C@H]4O3)O)[C@@H]3[C@@H]2C(OC3)=O)=C1 WKVZMKDXJFCMMD-UVWUDEKDSA-L 0.000 description 1
- 101000633503 Homo sapiens Nuclear receptor subfamily 2 group E member 1 Proteins 0.000 description 1
- 102100029534 Nuclear receptor subfamily 2 group E member 1 Human genes 0.000 description 1
- QAOWNCQODCNURD-UHFFFAOYSA-L Sulfate Chemical compound [O-]S([O-])(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
- 241001147416 Ursus maritimus Species 0.000 description 1
- 125000003368 amide group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000001450 anions Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000000889 atomisation Methods 0.000 description 1
- 125000001797 benzyl group Chemical group [H]C1=C([H])C([H])=C(C([H])=C1[H])C([H])([H])* 0.000 description 1
- 230000015572 biosynthetic process Effects 0.000 description 1
- HODFCFXCOMKRCG-UHFFFAOYSA-N bitolterol mesylate Chemical compound CS([O-])(=O)=O.C1=CC(C)=CC=C1C(=O)OC1=CC=C(C(O)C[NH2+]C(C)(C)C)C=C1OC(=O)C1=CC=C(C)C=C1 HODFCFXCOMKRCG-UHFFFAOYSA-N 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
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000012141 concentrate Substances 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- 239000003995 emulsifying agent Substances 0.000 description 1
- 150000002148 esters Chemical class 0.000 description 1
- JTOFFHFAQBLPTM-UHFFFAOYSA-N ethyl 2,2,3,3,4,4,5,5,6,6,7,7,8,8,8-pentadecafluorooctanoate Chemical compound CCOC(=O)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)C(F)(F)F JTOFFHFAQBLPTM-UHFFFAOYSA-N 0.000 description 1
- 125000004494 ethyl ester group Chemical group 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 239000012530 fluid Substances 0.000 description 1
- 239000000446 fuel Substances 0.000 description 1
- 239000003502 gasoline Substances 0.000 description 1
- 125000001183 hydrocarbyl group Chemical group 0.000 description 1
- 230000002209 hydrophobic effect Effects 0.000 description 1
- INQOMBQAUSQDDS-UHFFFAOYSA-N iodomethane Chemical compound IC INQOMBQAUSQDDS-UHFFFAOYSA-N 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 235000021388 linseed oil Nutrition 0.000 description 1
- 239000000944 linseed oil Substances 0.000 description 1
- 239000010687 lubricating oil Substances 0.000 description 1
- 238000004519 manufacturing process Methods 0.000 description 1
- 238000005259 measurement Methods 0.000 description 1
- 238000000034 method Methods 0.000 description 1
- 235000010446 mineral oil Nutrition 0.000 description 1
- 239000012184 mineral wax Substances 0.000 description 1
- 238000005065 mining Methods 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
- 238000005956 quaternization reaction Methods 0.000 description 1
- 229920006395 saturated elastomer Polymers 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003892 spreading Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 238000004347 surface barrier Methods 0.000 description 1
- 239000002344 surface layer Substances 0.000 description 1
- 238000004381 surface treatment Methods 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- CZPRKINNVBONSF-UHFFFAOYSA-M zinc;dioxido(oxo)phosphanium Chemical compound [Zn+2].[O-][P+]([O-])=O CZPRKINNVBONSF-UHFFFAOYSA-M 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
- C09K23/22—Amides or hydrazides
-
- 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
-
- 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
- This invention relates to my discovery of a new and useful'class of reactive fluorocarbon'compoun'ds. These compounds have utility as surface active agents, as starting compounds for making derivatives, and for other purposes;
- novel compounds are perfluoroalkyl dialkyl amine compot'inds'uniquely characterized as to structure. by having in the molecule a terminal carbonyl b'onded perfluoroalkyl chain which provides a nonpolar saturated fluorocarbonftail that is both' hydrophobic and 01ccphobic.
- Thesecompounds may be termed perfluoroa lkyl amidopolymethyl-ene-dialkylamine I compounds and are represented by the generic formula:
- This fluorocarbon tail is repellent not only to water but to oils and hydrocarbons and imparts unique surface active and surface treatment properties not possessed by corresponding compounds having a carbonylabonded hydrocarbon tail.
- the polymethylene chain provides a stable linkage between the terminal tertiary nitrogen atom and the nitrogen atom of the amido group, and also serves to enhance solubility in oils and waxes.
- the terminal dialkyl amino group renders the molecule oilsoluble at this end.
- the molecule is sufiiciently oilsoluble, and is oleophobic at one end and oleophilic at the other end. It is repellent to water, oils and waxes at the fluorocarbon end and yet is soluble in oils and Waxes at the tertiary amine end.
- These compounds are relatively insoluble in Water (even the lowest members of the series having a solubility in water of less than about 1% by weight at room temperature).
- waxes decreases with increase in lengthof the fliior'o'car bon tail, andWa-ter-insolubility is enhanced.
- the corresponding compounds of conventional organic chemistry having a carbonyl-bonded hydrocarbon tall decrease as to water solubility but increase as to oil solubility with increase in length of this chain.
- crease in length of the alkyl groups that are bonded to the terminal nitrogen atom, and increase in length of the intermediate polymethylene chain serve to further defluorocarbon tail containing-at least three carbon'at-orns' and the preferred number is 5 to 11. It is also of critical importance that this fluorocarbon chain be free from hydrogenatoms.
- the present compounds also'have particularly noteworthy value in serving asstartingcdmp'ounds for Ina-king the corresponding quaternary ammonium compounds, which can be readily prepared by using a hydrocarbon halide or sulfate quaternizing agent:
- RA is the quaternizing agent (e. g., methyl iodide or dimethyl sulfate)
- R is the hydrocarbon group thereof (e. g., an alkyl or benzyl group) that is covalently bonded to the quaternary nitrogen atom
- A is the anion of the quaternizing agent that is electrostatically bonded to the quaternary nitrogen atom.
- fluoro-' carbon quaternary ammonium compounds are unusually efiective surface active agents both in water and aqueous solutions and in oils and Waxes. Quaternization renders the compounds much more soluble in water and surface active in a queous systems, butdoes not destroy utility as surface active agents in oils and Waxes.
- Thesequaternary derivatives are 'describ'ecli in more detail and are claimed in my Companion application filed of evenpdate I herewith, SJN. 424,788.
- a feature of the present compounds is that l they can be readily prepared, by reaction of thealk yl'esters of The s rezfi a iea ra uatvrma refines? m nera s lat. 25 C.,was reduced from 31 dynes/cm.to v18 dynes/cm.
- Example This example illustrates'the preparation of the present compounds by a procedure of general utility, makin it dynes/cin. to 24 dynes/cm. at a concentration"of 0.1%;.
Description
United States Patent ice 1 2,764,603 AIZKYLAMINOA'IZKYL-PERFLUOROAMDES' Arthur H. .Ahlbrecht; White Bear Township, Ramsey County, Minn., assignor toMinnesota Mining Air ManufacturIng Company, St. Paul, Minn., a corporation of Delaware No nrawii g. Application'Api'il'21,'154,
' SerialNo. 424,789
lplaim. (c1. also-404.5
This invention relates to my discovery of a new and useful'class of reactive fluorocarbon'compoun'ds. These compounds have utility as surface active agents, as starting compounds for making derivatives, and for other purposes;
These novel compounds are perfluoroalkyl dialkyl amine compot'inds'uniquely characterized as to structure. by having in the molecule a terminal carbonyl b'onded perfluoroalkyl chain which provides a nonpolar saturated fluorocarbonftail that is both' hydrophobic and 01ccphobic. Thesecompounds may be termed perfluoroa lkyl amidopolymethyl-ene-dialkylamine I compounds and are represented by the generic formula:
Cn 2n+1C ONE-(CH2) mN R! I and bythe'equivalent formula-for compounds containing a normal p'e'rflu'oroalkyl chainz 0 H R no r)'"-ii-'N-' oni);nn
RI! whereri (the number of carbon atoms inlthe' terminal straight-chain orb ranched-chain perfluoroal kyl tail) has an integer value of 3 to 11 rh (the number of carbon atoms in the intermediatepolymethylene linkage) has an integer valueof 2 to 6, and R and'R ar'e a'lk'yl groups each containing 1 to 6 carbon atoms.
As is evident from the above: structural formulas-the complete molecule has a perfluoroalkyl .tail at one end and a' tertiary. amine group at the other end,"'. the-ftertiai'y nitrogen atom being. joined tothe fluorocarbon tail by an interposed amidopolymethylene linkage.
This fluorocarbon tail is repellent not only to water but to oils and hydrocarbons and imparts unique surface active and surface treatment properties not possessed by corresponding compounds having a carbonylabonded hydrocarbon tail. The polymethylene chain provides a stable linkage between the terminal tertiary nitrogen atom and the nitrogen atom of the amido group, and also serves to enhance solubility in oils and waxes. The terminal dialkyl amino group renders the molecule oilsoluble at this end. Thus the molecule is sufiiciently oilsoluble, and is oleophobic at one end and oleophilic at the other end. It is repellent to water, oils and waxes at the fluorocarbon end and yet is soluble in oils and Waxes at the tertiary amine end. These compounds are relatively insoluble in Water (even the lowest members of the series having a solubility in water of less than about 1% by weight at room temperature).
This makes possible water-insoluble molecules that can be dissolved in oils and Waxes and yet will concentrate at the surface to form an oriented surface layer having the fluorocarbon tails pointing outwardly and the opposite ends of the molecules pointed inwardly and dissolved in the oil or wax mass. A surface film results that is out- Patented Sept. 25, 1956 p 2 Wardly nonpolar and is both water and'oil repellent, and which greatly reduces the surface tension;
The solubility of the present compounds in oils and.
waxes decreases with increase in lengthof the fliior'o'car bon tail, andWa-ter-insolubility is enhanced. In contrast, the corresponding compounds of conventional organic chemistry having a carbonyl-bonded hydrocarbon tall decrease as to water solubility but increase as to oil solubility with increase in length of this chain. In; crease in length of the alkyl groups that are bonded to the terminal nitrogen atom, and increase in length of the intermediate polymethylene chain, serve to further defluorocarbon tail containing-at least three carbon'at-orns' and the preferred number is 5 to 11. It is also of critical importance that this fluorocarbon chain be free from hydrogenatoms. In particular, thepresence of even one hydrogen: atom onthe la'st'or next to last carbon atom of thel' fltail will markedly alter the surface active and solubility properties, reducing surface activity andthe by drophobic andoleophobiccharacteristics ofs'urface coat ings. Hydrogen is electropositive. whereas fluorine is stronglyelectronegative; hence th e presence of hydrogen and fluorine in the terminal portion of the'ltail renders it polar instead of nonpolar; and also renders the tail less s'table to heatingowing to the opportunity of 15:
hydrofluorination, and provides opportunity for chemical attack.
Thesefiuorocarbon-type tertiary amine compounds pro' vide surface active agents that are'highly effective a-s'ad ditivesfor oils and waxes. A remarkable degree ofsur face" tension' reduction can be achieved at coiiciitra tions'of 0. 1%' by Weight and less inanimaL'vegetable and'gnineraloils and waxesj ihc'luding petroleum solvent'sjgasoline, kerosene,'fuel' oils, lubricating oils, and para flin' waxes thereby, for instance} improving such properties as surface protection, flow, spreading, penetration, and atomization or sprayability. V, The corresponding non-fludrinated compounds of conventional org'a'nic chemistry do not have any significant surface tension'redu'c'tion effectin oils andwa'xes. M h I I .These compounds have utility as emulsifying agents for fluorbcarbonsand oils (the age'nt'collec'ting at'the interfaces'with the fluorocarbon tails dissolvedinl the fluorocarbon phase and the opposite ends of the'm'olecules dis solvedin the oil phase). I V
The present compounds also'have particularly noteworthy value in serving asstartingcdmp'ounds for Ina-king the corresponding quaternary ammonium compounds, which can be readily prepared by using a hydrocarbon halide or sulfate quaternizing agent:
where RA is the quaternizing agent (e. g., methyl iodide or dimethyl sulfate), R is the hydrocarbon group thereof (e. g., an alkyl or benzyl group) that is covalently bonded to the quaternary nitrogen atom, and A is the anion of the quaternizing agent that is electrostatically bonded to the quaternary nitrogen atom. These fluoro-' carbon quaternary ammonium compounds are unusually efiective surface active agents both in water and aqueous solutions and in oils and Waxes. Quaternization renders the compounds much more soluble in water and surface active in a queous systems, butdoes not destroy utility as surface active agents in oils and Waxes. Thesequaternary derivatives are 'describ'ecli in more detail and are claimed in my Companion application filed of evenpdate I herewith, SJN. 424,788.
' A feature of the present compounds is that l they can be readily prepared, by reaction of thealk yl'esters of The s fassfi a iea ra uatvrma refines? m nera s lat. 25 C.,was reduced from 31 dynes/cm.to v18 dynes/cm.
at a concentration of 0.1% J by weight. The value for a refined paratfin wax, in a fluid melted stateat 100 0., was reduced from 24 dynes/cm. to 18 dynes/cm. at a concentration of 0.1%; and that of a rnicrocrystalline paraflin wax, also measured; at 100" .C., .was. reduced from275 perfluoroalkyl monocarboxylic acids (conveniently the Q ethyl esters) with dialkylaminopolymethyleneamine compounds, as shown by the following equation:
The perfluoro ester starting compounds are disclosed in the U. S. patent of Diesslin, Kauck and Simons, No. 2,567,011 (Sept.-4, 1951).
Example This example illustrates'the preparation of the present compounds by a procedure of general utility, makin it dynes/cin. to 24 dynes/cm. at a concentration"of 0.1%;.
This. compound in minute. proportion materially inhibits the evaporation of volatile hydrocarbonssuch as gasoline, owing to formation of a surface barrier The following table lists other illustrative compounds that have been similarly prepared and gives the measunnecessary to individually describe similar experiments by which other compounds have been made.
- A 1000 ml. ,1necked flask was charged with 426' grams (0.965 mole) of ethyl perfluorocaprylate, CIF15C'OO'VC2H5, and 2 ml. of absolute diethyle ther as solvent. The flask was cooled in anice bath and 98.2
. grams (0365 mole) of dimethylaminopropylenearnine, H2NCsHeN(CHs)z, was added slowly enough tomain tain a temperature below 35 C. in the cooled reaction flask. p The flask was then removed from the ice bath and allowed to warm-to room temperature. ,It was placed under a 5 plate column forvacuum distillation. As the pressure was reduced, the ether distilled off, leaving the amine reaction product, which was distilled off at about mm. pressure'at the boiling range of 154-158 C. A
total of 440 grams (0.882 mole) was obtained (yield of 91.5%). The product was identified as relatively pure: C7F15CONHC3HN(CH3)2 Analysis showed 5.68% nitrogen (5.61% calc.). The boiling point was 155 C. at 18 mm. pressure. The reinactive index at C. was 1.3559. The product was a colorless viscous liquid having a characteristic amine odor. This compound may be designated as N,N-dimethyl-N'-perfiuoroeaprylamidopropyleneamine.
The surface activity of this compound was demonstrated by measurements showing the reduction in surface tension of mineral oils and waxes caused by the presence of minute proportions of the compound.
' ured vacuum boiling points (at the indicated pressures in millimeters) and refractive indices (at the indicated temperatures in degrees Centigrade). These compounds are allhigh 'boiling liquids at room temperature except for the last one, which is solid.,
- :The surface activity of the third compound in theabove list is illustrated by experiments on surface tension reduction wherein the value for linseed oil at 25 C.,was re- 7 duced from 32 to 19'dynes/cm. at0.1% concentration;
that for mineral oil at 25 C. from 3,1 to 19 dynes/cm.
References Cited in the file of this patent UNITED STATES PATENTS 2,567,011 Diesslin et al Sept. 4, 1951 2,589,674 Cook et a1. Mar. 18, 1952 2,593,737 Dies'slin et a1. Apr. 22, 1952 2,691,043
Husted Oct. 5, 1954
Priority Applications (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US424789A US2764603A (en) | 1954-04-21 | 1954-04-21 | Alkylaminoalkyl-perfluoroamides |
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
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US424789A US2764603A (en) | 1954-04-21 | 1954-04-21 | Alkylaminoalkyl-perfluoroamides |
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US2764603A true US2764603A (en) | 1956-09-25 |
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US424789A Expired - Lifetime US2764603A (en) | 1954-04-21 | 1954-04-21 | Alkylaminoalkyl-perfluoroamides |
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Cited By (59)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2990417A (en) * | 1959-10-19 | 1961-06-27 | Du Pont | 1, 2-bis |
US3006741A (en) * | 1958-03-31 | 1961-10-31 | Standard Oil Co | Motor fuels |
US3066100A (en) * | 1959-12-07 | 1962-11-27 | Gulf Research Development Co | Prevention of foaming of oils |
US3085075A (en) * | 1958-05-14 | 1963-04-09 | Lancaster Chemical Corp | Cured epoxy resins |
US3147065A (en) * | 1960-05-02 | 1964-09-01 | Minnesota Mining & Mfg | Quaternized halomethylamides |
US3188340A (en) * | 1961-12-08 | 1965-06-08 | Du Pont | Polyfluoro alkanamidoalkyl phosphates |
US3207730A (en) * | 1962-09-28 | 1965-09-21 | Minnesota Mining & Mfg | Polymers comprising a fluorinated quaternary salt of an amine-substituted acrylic acid ester |
US3238235A (en) * | 1963-04-29 | 1966-03-01 | Pennsalt Chemicals Corp | Fluorinated amido carboxylic acids and salts thereof |
US3271430A (en) * | 1963-02-07 | 1966-09-06 | Dow Chemical Co | Nu-perfluoroacyl polyalkylenimines |
US3382032A (en) * | 1961-12-12 | 1968-05-07 | Omega Chemicals Corp | Inhibition of volatilization of volatile organic compounds |
US3420697A (en) * | 1965-08-25 | 1969-01-07 | Allied Chem | Perfluoroalkyl-substituted polyamide oil-repellency compound and textile materials treated therewith |
US3428709A (en) * | 1966-08-22 | 1969-02-18 | Geigy Chem Corp | Polymers of n-perfluoboalkanoylamino-and n-perfluoroalkanoylaminoalkyl acrylamides and methacrylamides |
US3458571A (en) * | 1967-04-06 | 1969-07-29 | Minnesota Mining & Mfg | Fluorocarbon polyamines |
DE2008531A1 (en) * | 1969-02-19 | 1970-11-12 | Minnesota Mining and Manufacturing Company, St, Paul, Minn. (V.St.A.) | Perfluorinated amine oxides |
US3547995A (en) * | 1967-03-07 | 1970-12-15 | Du Pont | Perfluoroalkyl ether amidoamine oxides |
US3791066A (en) * | 1971-09-01 | 1974-02-12 | Exxon Research Engineering Co | Enhancing the operation of a gasoline engine |
US3929854A (en) * | 1971-03-29 | 1975-12-30 | Hoechst Ag | Bunte salts containing fluoro-alkyl groups |
US3950494A (en) * | 1974-06-25 | 1976-04-13 | Minnesota Mining And Manufacturing Company | Suppression of volatilization of noxious acidic vapors |
US4000168A (en) * | 1970-04-14 | 1976-12-28 | Produits Chimiques Ugine Kuhlmann | Carboxylated polyfluoroamines |
US4035149A (en) * | 1975-01-15 | 1977-07-12 | Shell Oil Company | Vapor barriers for liquid conservation |
US4089804A (en) * | 1976-12-30 | 1978-05-16 | Ciba-Geigy Corporation | Method of improving fluorinated surfactants |
US4107055A (en) * | 1976-12-15 | 1978-08-15 | Allied Chemical Corporation | Fabric coating compositions, method and coated fabric having dry soil resist finishes |
US4113774A (en) * | 1977-09-09 | 1978-09-12 | Sterling Drug Inc. | N-(Dichloroacetyl) diamine compounds and process of preparing same |
US4139483A (en) * | 1977-02-28 | 1979-02-13 | Xerox Corporation | Electrostatographic toner composition containing surfactant |
US4198477A (en) * | 1977-02-28 | 1980-04-15 | Xerox Corporation | Method of using electrostatographic toner composition with surfactant |
US4484990A (en) * | 1980-06-16 | 1984-11-27 | Minnesota Mining And Manufacturing Company | Mist suppressant for solvent extraction metal electrowinning |
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