IE58051B1 - Water-removing composition based on fluorochloro-hydrocarbon and surfactant - Google Patents
Water-removing composition based on fluorochloro-hydrocarbon and surfactantInfo
- Publication number
- IE58051B1 IE58051B1 IE155385A IE155385A IE58051B1 IE 58051 B1 IE58051 B1 IE 58051B1 IE 155385 A IE155385 A IE 155385A IE 155385 A IE155385 A IE 155385A IE 58051 B1 IE58051 B1 IE 58051B1
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- denotes
- carbon atoms
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- composition according
- formula
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- 239000000203 mixture Substances 0.000 title claims abstract description 56
- 239000004094 surface-active agent Substances 0.000 title claims abstract description 14
- 239000004215 Carbon black (E152) Substances 0.000 title claims description 7
- -1 alkyl phosphoric acid Chemical compound 0.000 claims abstract description 19
- 150000001412 amines Chemical class 0.000 claims abstract description 8
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- NBIIXXVUZAFLBC-UHFFFAOYSA-N phosphoric acid Substances OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 claims abstract description 5
- 229910000147 aluminium phosphate Inorganic materials 0.000 claims abstract description 4
- 125000004432 carbon atom Chemical group C* 0.000 claims description 20
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 12
- 125000000217 alkyl group Chemical group 0.000 claims description 9
- 239000002904 solvent Substances 0.000 claims description 9
- AJDIZQLSFPQPEY-UHFFFAOYSA-N 1,1,2-Trichlorotrifluoroethane Chemical compound FC(F)(Cl)C(F)(Cl)Cl AJDIZQLSFPQPEY-UHFFFAOYSA-N 0.000 claims description 8
- 150000003254 radicals Chemical group 0.000 claims description 7
- 150000001735 carboxylic acids Chemical class 0.000 claims description 6
- 229930195733 hydrocarbon Natural products 0.000 claims description 6
- 150000002430 hydrocarbons Chemical class 0.000 claims description 6
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 6
- 229920006395 saturated elastomer Polymers 0.000 claims description 6
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 5
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 5
- 150000005827 chlorofluoro hydrocarbons Chemical class 0.000 claims description 4
- 125000001931 aliphatic group Chemical group 0.000 claims description 3
- WPYMKLBDIGXBTP-UHFFFAOYSA-N benzoic acid Chemical compound OC(=O)C1=CC=CC=C1 WPYMKLBDIGXBTP-UHFFFAOYSA-N 0.000 claims description 3
- 239000000470 constituent Substances 0.000 claims description 3
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 3
- GAWIXWVDTYZWAW-UHFFFAOYSA-N C[CH]O Chemical group C[CH]O GAWIXWVDTYZWAW-UHFFFAOYSA-N 0.000 claims description 2
- 238000000034 method Methods 0.000 claims description 2
- 125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 claims description 2
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 claims description 2
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical group [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 claims 2
- 235000011007 phosphoric acid Nutrition 0.000 claims 2
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 1
- 150000003016 phosphoric acids Chemical class 0.000 claims 1
- 239000008346 aqueous phase Substances 0.000 abstract description 5
- 239000012074 organic phase Substances 0.000 abstract description 5
- 238000000926 separation method Methods 0.000 abstract description 4
- 150000001732 carboxylic acid derivatives Chemical class 0.000 abstract 1
- 125000001453 quaternary ammonium group Chemical group 0.000 abstract 1
- 238000009472 formulation Methods 0.000 description 18
- 238000001035 drying Methods 0.000 description 7
- 239000012071 phase Substances 0.000 description 7
- 239000002253 acid Substances 0.000 description 6
- 150000007513 acids Chemical class 0.000 description 4
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000000706 filtrate Substances 0.000 description 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 3
- 239000000047 product Substances 0.000 description 3
- QPFMBZIOSGYJDE-UHFFFAOYSA-N 1,1,2,2-tetrachloroethane Chemical compound ClC(Cl)C(Cl)Cl QPFMBZIOSGYJDE-UHFFFAOYSA-N 0.000 description 2
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- KFZMGEQAYNKOFK-UHFFFAOYSA-N Isopropanol Chemical compound CC(C)O KFZMGEQAYNKOFK-UHFFFAOYSA-N 0.000 description 2
- PXHVJJICTQNCMI-UHFFFAOYSA-N Nickel Chemical compound [Ni] PXHVJJICTQNCMI-UHFFFAOYSA-N 0.000 description 2
- 150000001338 aliphatic hydrocarbons Chemical class 0.000 description 2
- 239000012153 distilled water Substances 0.000 description 2
- 238000001914 filtration Methods 0.000 description 2
- UOCLXMDMGBRAIB-UHFFFAOYSA-N 1,1,1-trichloroethane Chemical compound CC(Cl)(Cl)Cl UOCLXMDMGBRAIB-UHFFFAOYSA-N 0.000 description 1
- UGCSPKPEHQEOSR-UHFFFAOYSA-N 1,1,2,2-tetrachloro-1,2-difluoroethane Chemical compound FC(Cl)(Cl)C(F)(Cl)Cl UGCSPKPEHQEOSR-UHFFFAOYSA-N 0.000 description 1
- SCYULBFZEHDVBN-UHFFFAOYSA-N 1,1-Dichloroethane Chemical compound CC(Cl)Cl SCYULBFZEHDVBN-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- 239000011149 active material Substances 0.000 description 1
- 159000000032 aromatic acids Chemical class 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002091 cationic group Chemical group 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 235000013985 cinnamic acid Nutrition 0.000 description 1
- WBYWAXJHAXSJNI-UHFFFAOYSA-N cinnamic acid group Chemical class C(C=CC1=CC=CC=C1)(=O)O WBYWAXJHAXSJNI-UHFFFAOYSA-N 0.000 description 1
- 230000000295 complement effect Effects 0.000 description 1
- NZNMSOFKMUBTKW-UHFFFAOYSA-N cyclohexanecarboxylic acid Chemical compound OC(=O)C1CCCCC1 NZNMSOFKMUBTKW-UHFFFAOYSA-N 0.000 description 1
- 239000003599 detergent Substances 0.000 description 1
- 238000006073 displacement reaction Methods 0.000 description 1
- 238000004090 dissolution Methods 0.000 description 1
- 238000004945 emulsification Methods 0.000 description 1
- 238000000605 extraction Methods 0.000 description 1
- 229910052731 fluorine Inorganic materials 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000010437 gem Substances 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 150000003840 hydrochlorides Chemical class 0.000 description 1
- MTNDZQHUAFNZQY-UHFFFAOYSA-N imidazoline Chemical compound C1CN=CN1 MTNDZQHUAFNZQY-UHFFFAOYSA-N 0.000 description 1
- 238000009434 installation Methods 0.000 description 1
- 239000003350 kerosene Substances 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 238000002156 mixing Methods 0.000 description 1
- 229910052759 nickel Inorganic materials 0.000 description 1
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 1
- WWZKQHOCKIZLMA-UHFFFAOYSA-N octanoic acid Chemical compound CCCCCCCC(O)=O WWZKQHOCKIZLMA-UHFFFAOYSA-N 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 150000003047 pimelic acids Chemical class 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 239000011819 refractory material Substances 0.000 description 1
- 150000003330 sebacic acids Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 150000003442 suberic acids Chemical class 0.000 description 1
- 239000008399 tap water Substances 0.000 description 1
- 235000020679 tap water Nutrition 0.000 description 1
- 238000002604 ultrasonography Methods 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C23—COATING METALLIC MATERIAL; COATING MATERIAL WITH METALLIC MATERIAL; CHEMICAL SURFACE TREATMENT; DIFFUSION TREATMENT OF METALLIC MATERIAL; COATING BY VACUUM EVAPORATION, BY SPUTTERING, BY ION IMPLANTATION OR BY CHEMICAL VAPOUR DEPOSITION, IN GENERAL; INHIBITING CORROSION OF METALLIC MATERIAL OR INCRUSTATION IN GENERAL
- C23G—CLEANING OR DE-GREASING OF METALLIC MATERIAL BY CHEMICAL METHODS OTHER THAN ELECTROLYSIS
- C23G5/00—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents
- C23G5/02—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents
- C23G5/028—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons
- C23G5/02809—Cleaning or de-greasing metallic material by other methods; Apparatus for cleaning or de-greasing metallic material with organic solvents using organic solvents containing halogenated hydrocarbons containing chlorine and fluorine
-
- C—CHEMISTRY; METALLURGY
- C03—GLASS; MINERAL OR SLAG WOOL
- C03C—CHEMICAL COMPOSITION OF GLASSES, GLAZES OR VITREOUS ENAMELS; SURFACE TREATMENT OF GLASS; SURFACE TREATMENT OF FIBRES OR FILAMENTS MADE FROM GLASS, MINERALS OR SLAGS; JOINING GLASS TO GLASS OR OTHER MATERIALS
- C03C23/00—Other surface treatment of glass not in the form of fibres or filaments
- C03C23/0085—Drying; Dehydroxylation
-
- 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
- C09K3/00—Materials not provided for elsewhere
- C09K3/18—Materials not provided for elsewhere for application to surfaces to minimize adherence of ice, mist or water thereto; Thawing or antifreeze materials for application to surfaces
Landscapes
- Chemical & Material Sciences (AREA)
- Engineering & Computer Science (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Chemical Kinetics & Catalysis (AREA)
- General Chemical & Material Sciences (AREA)
- Combustion & Propulsion (AREA)
- Mechanical Engineering (AREA)
- Life Sciences & Earth Sciences (AREA)
- Metallurgy (AREA)
- Geochemistry & Mineralogy (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Extraction Or Liquid Replacement (AREA)
- Detergent Compositions (AREA)
- Lubricants (AREA)
- Drying Of Gases (AREA)
- Solid-Sorbent Or Filter-Aiding Compositions (AREA)
- Water Treatment By Sorption (AREA)
- Materials Applied To Surfaces To Minimize Adherence Of Mist Or Water (AREA)
Abstract
The composition based on fluorochlorohydrocarbon contains a surface active agent resulting from the reaction of a quaternary ammonium chlorhydrate with an alkyl phosphoric acid in the presence of a fluor-containing amine and a carboxylic acid. The separation rate of the aqueous and organic phase is improved.
Description
The present invention relates to a composition which can be used, in particular, for removing water present on a wet surface.
Water-removing compositions of various types have 5 been described. Such compositions generally contain a fluorochlorohydrocarbon, more specifically 1,1,2-trichloro1,2,2-trifluoroethane, and one or more surfactants, for example an alkyl phosphate neutralised by means of an amine, an amine salt, a diamide, where appropriate in the presence of a carboxylic acid or a cationic imidazoline surfactant, or alternatively a surfactant resulting from the reaction of quaternary ammonium chloride with an alkylphosphoric acid in the presence of a fluorinated amine (see European Patent 83/400293.3).
The present invention relates to an improvement in the compositions described in the said European Patent, the improvement being in respect of the rate of separation of the aqueous phase from the organic phase during the removal of the water.
More specifically, the invention relates to a water-removing composition which can be used for displacing Liquid water, the said composition containing a solvent consisting of at least 50% by weight of a chlorofluorohydrocarbon and a surfactant resulting from the reaction of a quaternary ammonium chloride of formula: (R>2^+^N CR’)2 εΐ(-) (I) with an alkyl phosphoric acid of formula : (R0)p CH0)2-p CII) in the presence of a fluorinated amine of formula: Rp XNR-, R2 (III), in which formulae Rp denotes a linear or branched perfluorinated chain CqF2q+1z in wbich q is an integer between 2 and 20, X is a bivalently bonded group, optionally partially halogenated, R is an alkyl group having 6 to 18 carbon atoms, R' is an alkyl group having 1 to 2 carbon atoms, R-j and R2^ which may be identical or different, denote a hydrogen atom, an alkyl radical or a hydroxyalkyl radical having from 1 to 8 carbon atoms, and R is an alkyl group having from 1 to 18 carbon atoms, the said composition being characterised in that it contains at least one carboxylic acid chosen from saturated linear, branched or cyclic aliphatic mono- or diacids having from 5 to 10 carbon atoms, and optionally substituted; unsaturated Linear or branched aliphatic mono- or diacids having from 5 to 30 carbon atoms and optionally substituted; and aromatic acids having from 7 to 9 carbon atoms, optionally mono- or polysubstituted with amino, nitro, hydroxy or methoxy groups.
The compositions according to the invention advantageously contain, by weight: - from 90 to 99.9855 of solvent - from 0.01 to 85ό of surfactant - from 0.01 to 2?ό of carboxylic acid, the total of the amounts of the three constituents being 100%.
In these compositions, the chlorofluorohydrocarbon is advantageously 1,1,2-trichloro-1,2,2-trifluoroethane and the complementary solvent is advantageously an aliphatic hydrocarbon such as hexane, an aliphatic cut such as white spirit or kerosene, a halogenated aliphatic hydrocarbon such as chloroform, methylene chloride, a dichloroethane or trichloroethane, 1,1 , 2,2-tetrachloroethane , 1,1,2,2-tetrachloro-1,2-difluoroethane, perchloroethylene, trichloroethylene, or an aromatic hydrocarbon such as xylene.
The various surfactants described in European Patent 85/400293.3 can be used. The products are preferably those which result from the reaction of a quaternary ammonium chloride of formula (I) in which R' denotes a methyl group and R denotes an alkyl group having from 12 to 18 carbon atoms, with a mixture of mono- and dialkylphosphoric acids of formula (II), in which the symbol R denotes an alkyl radical having from 4 to carbon atoms, this reaction being performed in the presence of a fluorinated amine of formula (III), in which the symbol q is from 4 to 10, R^ and R2 denote a hydrogen atom or a methyl, ethyl or hydroxy ethyl radical, and X denotes a saturated or unsaturated bivalent radical which is wholly hydrocarbon or is hydrocarbon substituted by a fluorine atom or a radical consisting of one or more of the above bivalent radicals and a -CONH- or -NH- group.
The preparation of the surfactant, preferably in the solvent medium of the composition according to the invention, is described in European Patent 83/400293.3.
Examples of acids which can be used include: valeric, caproic, oenanthic, caprylic, pimelic, suberic, azelaic and sebacic acids; oleic, linoleic, undecylenic and ricinoleic acids; cyclohexanemonocarboxylic or trans-1,2- or -1 , 4-cyc1ohexanedicarboxy1ic acids; benzoic, ortho- or para-hydroxybenzoic, 2-ami no-benzoic , 3-nitro15 salicylic, 5-nitrosalicylic, ortho-toluic and cinnamic acids The water-removing composition according to the invention can be prepared by simple mixing of its constituents. It can also be produced by adding the carboxylic acid to a composition containing the solvent and the surfactant, prepared separately or in the presence of all or part of the solvent. When the surfactant is prepared directly in the solvent, the composition can contain all or part of the fluorinated amine hydrochloride formed, and this product can be removed in different ways, for example by dissolution in water during drying, or by filtration, advantageously performed from a concentrated composition. The choice of extraction method of this hydrochloride is linked to its solubility in the medium as will be appreciated by those skilled in the art.
The compositions according to the invention make it possible to accomplish very effective drying, and more specifically to remove water from the surface of articles of various kinds. It is especially suitable for removing water from metal articles, objects made of glass or refractory materials, precious stones or plastic objects.
By means of these compositions, rapid removal or displacement of the water is observed; also there is a substantial increase in the rate of separation of the aqueous and organic phases formed during the removal of the water, which constitutes an advantage when the compositions are used in installations provided for this purpose. Thus, the water, rapidly separated from the drying composition, may be discharged into the drain by means of a suitable device (settler).
The Examples which follow further illustrate the present invention. In these examples, the abbreviations have the following significances: - + ) chloride: dimethyldi 1aurylammonium chloride ( + ) (-) L C Ί 2 h25^2 N C I The product used is commercially available, containing 75% of active material in isopropanol and 0.161 chlorine equivalent per 100 g. It is a mixture of homologues according to the following distribution (by weight):C8 3 % C16 10 %c10 6% C-^g saturated 2%C12 56% C -, g unsaturated 5%C1 4 18% - F 113 : 1,1,2-trichloro-1z2,2-trifIuoroetha P r epa ration and formulation Th e following mixture is prepared at room temperature: . chloride: 8.32 g (0.88 mole) . Buty I phosphoric acid: 2.69 g (1 mole) . Amine C^F-j 3H4S O2NH N (04^)27.82 g (1 mole) . F 113 : 150 g The initial solution becomes turbid quite quickly, and after the mixture has been left to stand for 24 hours, 4.2 g of a white crystallised solid, identified as the fluorinated amine hydrochloride, are collected after filtration.
The filtrate, which is completely clear, is diluted with F 113 (concentration 0.04% by weight).
This formulation, a control, is designated Formulation 1 .
Formulation 2 contains, by weight, 99.86% of F 113, 0.04% of filtrate of the Formulation 1 and 0.1% of ca p ry I i c acid. Formulation 3 contains, by weight, 99.86% of F 113, 0.04% o f the filtrate of the Formulation 1 and 0.1% o f benzoi c acid. • Exa mpI e 1: emulsification test 1.1. In a bottle, there are placed 50 g of the formulation to be tested and 18 g of distilled water. The bottle is shaken vigorously for 30 seconds. The emulsion formed is then allowed to stand, and the time, and the thickness of the interface between the organic lower phase and the aqueous upper phase, are measured.
The following observations are made: Thickness in mm of the interface Duration in Formulation Fo rmulation Formulation mi nut es No . 1 No. 2 No. 3 5 20 3 1 10 5 0 0 60 0 0 0 The bottles containing the above formulations are again shaken for 30 seconds.
Thickness in mm of the interface i Du ra t i on j Formulation formulation Formulation Min Hours No. 1 No. 2 No. 3 10 30 13 10 20 30 1 1 6 60 30 4 1 2 28 2 0 48 25 1 0 1.2. (Control). In a tank of approximate size 200 x 150 x 150 mm, a mixture consisting of 7 I of the Formulation No. 1 and 0.800 I of distilled water is circulated with continuous recycling by means of a pump and at a flow rate of approximately 300 l/h.
After 5 min, it is observed that the mixture has a homogeneous appearance. A sample withdrawn after this time shows, after 3 min, 2 phases: a slightly turbid lower organic phase and a viscous upper phase which is, in fact, an emulsion of the organic phase and the aqueous phase.
The appearance of a c I ea r aqueous phase is not observed after 48 hours .
. (Invention). The procedure described above is carried out using the Formulation No. 3. A sample is withdrawn after the mixture has been circulated at a flow rate of approximately 300 l/h for 5 minutes. The 9 sample shows, after distinctly separate emulsion. minutes, an a qu eous phase o rga ni c w i t h ou t phase and a a t ra c e of Example 2: drying tests 5 Drying of nickel 45 A 45 rpm sta mper is alkaline detergent solution rpm record stampers. previously degreased in an in the presence of ultrasound. and then rinsed in running tap water. It is then immersed in one of the Formulations 1, 2 or 3, brought to boiling 10 for 3 minutes, and then rinsed in pure F 113.
Over 5 tests, it is observed that 100% drying of this stamper is obtained with each of the formulations used: the compositions according to the invention hence combine great drying efficiency with the improved rate of separation of the phases.
Claims (9)
1.CLAIMS Ί. A water-removing composition which comprises a solvent, at least 50% by weight of which is a chlorofluorohydrocarbon, a surfactant resulting from the reaction of a quaternary ammonium chloride of formula: (R) 2 ^ + ^N (R') 2 Cl (_) (I) with an alkyl phosphoric acid of formula: (R0) (H0)„ PO„H (II) in the presence of a p 2-p 2 fluorinated amine of formula: R^ XNR^ (III) > in which formulae R^ denotes a linear or branched perfluorinated chain C F„ . , in which q is an integer from 2 to q 2q+1 73 20, X denotes a bivalent hydrocarbon group, optionally partially halogenated, R denotes an alkyl group having 6 to 18 carbon atoms, R' denotes an alkyl group having 1 or 2 carbon atoms, Rand R^, which may be identical or different, denote a hydrogen atom, an alkyl radical or a hydroxyalkyl radical having from 1 to 8 carbon atoms, and R denotes an alkyl group having from 1 to 18 carbon atoms, and at least one carboxylic acid which is an optionally substituted saturated linear, branched or cyclic aliphatic mono- or diacid having from 5 to 10 carbon atoms; an optionally substituted unsaturated linear or branched aliphatic mono- or diacid having from 5 to 50 carbon atoms or an aromatic acid having from 7 to 9 carbon atoms, optionally substituted by one or more amino, nitro, hydroxy or methoxy groups.
2. A composition according to claim 1, which contains (by weight) from 90 to 99.98% of solvent, from 0.01 to 8% of surfactant and from 0.01 to 2% of carboxylic acid, the total amount of the three constituents being 1005o.
3. A composition according to claim 1 or 2,in which the chlorofluorohydrocarbon is 1 ,1 , 2-trichloro-1,2,2trif luoroeth ane .
4. A composition according to any one of claims 1 to 3 in which R’ denotes a methyl group and R denotes an alkyl group having from 12 to 18 carbon atoms.
5. A composition according to any one of claims 1 to 4 in which R denotes an alkyl radical having from 4 to 14 carbon atoms.
6. A composition according to any one of claims 1 to 5 in which q is from 4 to 10, R^ and R^ denote a hydrogen atom or a methyl, ethyl or hydroxyethyl radical and X denotes a saturated or unsaturated bivalent wholly hydrocarbon or hydrocarbon partially substituted by fluorine radical or a radical containing one or more said bivalent radicals and a -50^-, -CONH- or -NH- group.
7. A composition according to any one of claims 1 to 6, in which the surfactant is one resulting from the reaction of a quaternary ammonium chloride of formula I in which R' denotes a methyl group and R denotes an alkyl group having from 12 to 18 carbon atoms, with a mixture of mono- and dia1ky1 phosphoric acids of formula (II), in which R denotes an alkyl radical having from 4 to 14 carbon atoms, this reaction being performed in the presence of a fluorinated amine of formula (III), in which q is from 4 to 10, R^ and R 2 denote a hydrogen atom or a methyl, ethyl or hydroxy ethyl radical, and X denotes a saturated or unsaturated bivalent wholly hydrocarbon or hydrocarbon partially substituted by fluorine radical, or a radical containing one or more of the above bivalent radicals and a -SC^-» -CONH- or -NH- group. 5
8. A composition according to claim 1 substantially as described in the Examples.
9. A method of removing water from the surface of an article, which comprises applying thereto a composition as claimed in any one of the preceding claims.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR8410345A FR2566788A1 (en) | 1984-06-29 | 1984-06-29 | ANTIFOULING COMPOSITION BASED ON SURFACTANT FLUOROCHLOROHYDROCARBIDE AND CARBOXYLIC ACID |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| IE851553L IE851553L (en) | 1985-12-29 |
| IE58051B1 true IE58051B1 (en) | 1993-06-16 |
Family
ID=9305618
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| IE155385A IE58051B1 (en) | 1984-06-29 | 1985-06-24 | Water-removing composition based on fluorochloro-hydrocarbon and surfactant |
Country Status (14)
| Country | Link |
|---|---|
| EP (1) | EP0189436B1 (en) |
| JP (1) | JPS61502947A (en) |
| KR (1) | KR860700131A (en) |
| CN (1) | CN85105017A (en) |
| AT (1) | ATE37897T1 (en) |
| AU (1) | AU577395B2 (en) |
| DE (1) | DE3565552D1 (en) |
| ES (1) | ES8608029A1 (en) |
| FR (1) | FR2566788A1 (en) |
| GR (1) | GR851606B (en) |
| IE (1) | IE58051B1 (en) |
| PT (1) | PT80740B (en) |
| TR (1) | TR22965A (en) |
| WO (1) | WO1986000329A1 (en) |
Families Citing this family (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE3918472A1 (en) * | 1989-06-06 | 1990-12-13 | Siemens Ag | HYDROPHOBIC AGENTS AND APPLICATION METHOD, ESPECIALLY FOR INK JET PRINT HEADS |
| WO1992011350A1 (en) * | 1990-12-18 | 1992-07-09 | Allied-Signal Inc. | Dewatering compositions comprising 1,1-dichloro-1-fluoroethane; dichlorotrifluoroethane; and alkanol having 1 to 4 carbon atoms |
| FR2691473B1 (en) * | 1992-05-21 | 2002-05-17 | Atochem Elf Sa | Compositions for dewetting or degreasing solid surfaces. |
| US5610128A (en) * | 1994-12-14 | 1997-03-11 | Alliedsignal Inc. | Surfactants and drying and drycleaning compositions which utilize said surfactants |
| FR2757871B1 (en) * | 1996-12-27 | 1999-03-26 | Aerospatiale | WATERPROOFING COMPOSITION COMPRISING A HYDROPHOBIC AGENT AND A SOLVENT, APPLICATION FOR THE REMOVAL OF SURFACE WATER IN PARTICULAR FROM WINDSCREENS OF VEHICLES OR AIRCRAFT |
| FR2766836B1 (en) | 1997-07-31 | 1999-09-24 | Atochem Elf Sa | QUASI AZEOTROPIC MIXTURE BASED ON 1,1,1,3,3- PENTAFLUOROBUTANE, METHYLENE CHLORIDE AND METHANOL FOR THE TREATMENT OF SOLID SURFACES |
| EP3065649A1 (en) | 2013-11-04 | 2016-09-14 | Covidien LP | Surgical fastener applying apparatus |
| CN106367220A (en) * | 2016-08-24 | 2017-02-01 | 诺而曼环保科技（江苏）有限公司 | Water replacement additive used in hydrocarbon cleaning agent, and preparation and use methods of same |
Family Cites Families (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR2353625A1 (en) * | 1976-06-04 | 1977-12-30 | Rhone Poulenc Ind | NEW COMPOSITIONS BASED ON TRICHLOROTRIFLUOROETHANE AND THEIR APPLICATION TO SURFACE TREATMENT |
| FR2522007A1 (en) * | 1982-02-23 | 1983-08-26 | Ugine Kuhlmann | COMPOSITION FOR SURFACE WELDING |
| FR2527625A1 (en) * | 1982-05-27 | 1983-12-02 | Chloe Chemie | COMPOSITION BASED ON FLUOROCHLOROHYDROCARBIDE, PHOSPHORIC ESTER AND CARBOXYLIC ACID |
-
1984
- 1984-06-29 FR FR8410345A patent/FR2566788A1/en active Pending
-
1985
- 1985-06-24 AT AT85903008T patent/ATE37897T1/en not_active IP Right Cessation
- 1985-06-24 IE IE155385A patent/IE58051B1/en not_active IP Right Cessation
- 1985-06-24 AU AU44926/85A patent/AU577395B2/en not_active Expired - Fee Related
- 1985-06-24 WO PCT/FR1985/000165 patent/WO1986000329A1/en not_active Ceased
- 1985-06-24 EP EP85903008A patent/EP0189436B1/en not_active Expired
- 1985-06-24 DE DE8585903008T patent/DE3565552D1/en not_active Expired
- 1985-06-24 JP JP60502726A patent/JPS61502947A/en active Pending
- 1985-06-28 TR TR30549A patent/TR22965A/en unknown
- 1985-06-28 GR GR851606A patent/GR851606B/el unknown
- 1985-06-28 PT PT80740A patent/PT80740B/en unknown
- 1985-06-28 ES ES544677A patent/ES8608029A1/en not_active Expired
- 1985-07-02 CN CN198585105017A patent/CN85105017A/en active Pending
-
1986
- 1986-02-24 KR KR860700107A patent/KR860700131A/en not_active Withdrawn
Also Published As
| Publication number | Publication date |
|---|---|
| JPS61502947A (en) | 1986-12-18 |
| PT80740B (en) | 1987-10-20 |
| EP0189436A1 (en) | 1986-08-06 |
| AU577395B2 (en) | 1988-09-22 |
| DE3565552D1 (en) | 1988-11-17 |
| ES8608029A1 (en) | 1986-06-01 |
| EP0189436B1 (en) | 1988-10-12 |
| IE851553L (en) | 1985-12-29 |
| CN85105017A (en) | 1987-03-04 |
| PT80740A (en) | 1985-10-01 |
| WO1986000329A1 (en) | 1986-01-16 |
| AU4492685A (en) | 1986-01-24 |
| TR22965A (en) | 1988-12-13 |
| ES544677A0 (en) | 1986-06-01 |
| FR2566788A1 (en) | 1986-01-03 |
| KR860700131A (en) | 1986-03-31 |
| ATE37897T1 (en) | 1988-10-15 |
| GR851606B (en) | 1985-11-25 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| MK9A | Patent expired |