EP0374205A1 - Kationenaktive zusammensetzungen; ihre verwendung für bituminöse emulsionen - Google Patents

Kationenaktive zusammensetzungen; ihre verwendung für bituminöse emulsionen

Info

Publication number
EP0374205A1
EP0374205A1 EP89904093A EP89904093A EP0374205A1 EP 0374205 A1 EP0374205 A1 EP 0374205A1 EP 89904093 A EP89904093 A EP 89904093A EP 89904093 A EP89904093 A EP 89904093A EP 0374205 A1 EP0374205 A1 EP 0374205A1
Authority
EP
European Patent Office
Prior art keywords
general formula
weight
oxyalkylated
composition
integer equal
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Pending
Application number
EP89904093A
Other languages
English (en)
French (fr)
Inventor
René Louis Auguste BROUARD
Luc Etienne André NAVASCUES
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Carbonisation et Charbons Actifs CECA SA
Original Assignee
Carbonisation et Charbons Actifs CECA SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Carbonisation et Charbons Actifs CECA SA filed Critical Carbonisation et Charbons Actifs CECA SA
Publication of EP0374205A1 publication Critical patent/EP0374205A1/de
Pending legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J3/00—Processes of treating or compounding macromolecular substances
    • C08J3/02—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques
    • C08J3/03—Making solutions, dispersions, lattices or gels by other methods than by solution, emulsion or suspension polymerisation techniques in aqueous media
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/02—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having etherified hydroxy groups and amino groups bound to acyclic carbon atoms of the same carbon skeleton
    • C07C217/50—Ethers of hydroxy amines of undetermined structure, e.g. obtained by reactions of epoxides with hydroxy amines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
    • C08K5/00—Use of organic ingredients
    • C08K5/16—Nitrogen-containing compounds
    • C08K5/17—Amines; Quaternary ammonium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K23/00—Use of substances as emulsifying, wetting, dispersing, or foam-producing agents
    • C09K23/16—Amines or polyamines
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
    • C08J2395/00—Bituminous materials, e.g. asphalt, tar or pitch
    • 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

  • the present invention relates to liquid compositions of fatty amines and similar products with cationic properties.
  • Amines represented by the general formula R-NH 2 , where R is a hydrocarbon radical containing at least 10 carbon atoms, develop in addition to the ordinary chemical properties which characterize the class of amines, and in particular a basic force comparable to that of l 'ammonia, surfactant properties, especially at the water / hydrocarbon liquid interfaces and very marked adsorption properties on mineral surfaces.
  • Z a inopropyl
  • Z oxypropyl
  • Z a idoethyl
  • Fluid compositions were made at room temperature using solvents. Apart from the banal effect of loss of relative efficiency by dilution, other disadvantages of the use of solvents are well known: heavy solvents are found, unnecessary or undesirable, in the final products; light solvents are, of course, removable, but thereby also sources of flammability and / or pollution. In addition, solvent formulations of long chain cationic compounds generally do not exhibit satisfactory low temperature storage behavior, as will be discussed shortly.
  • the object of the present invention is to remedy these drawbacks. Its object is to provide compositions of cationic non-flammable amino active derivatives, which are absolutely liquid at room temperature, which fully retain their liquidity when they remain indefinitely exposed to the atmosphere, which do not give rise to the formation of gels, of precipitates. or deposits when they have been maintained for a prolonged period at temperatures close to zero degrees centigrade or which do not give rise to the formation of such gels, precipitates or deposits which persist for a long time by return to ambient temperature.
  • compositions by combining fatty amines, diamines or polyamines partially substituted for nitrogen by an alkylene oxide such as ethylene oxide, propylene, butylene oxide, (which for the sake of convenience will hereinafter simply be called amines oxyalkylees), alkyl etheramines of general formula
  • n is an integer equal to 2 or 3
  • m is an integer equal to 2 or 3
  • p is a number which can take any value from 0 to 3
  • R is a branched alkyl chain, of the type
  • the weight ratio between the oxyalkylated amines and the etheramines is between 20/80 and 80/20.
  • Such compositions according to the invention are obtained without major difficulty by simple mixing at room temperature of the compounds of the oxyalkylated amine type and of the compounds of the etheramine type, the operation being all the easier when these substances are liquid at room temperature or at least easily fusible at temperatures not exceeding 50 ° C, and that in the liquid state, they are soluble in each other in all proportions.
  • alkyloxypropyl-N-propylenediamines which are compounds corresponding to the general formula are preferred
  • Q 1 # Q 2 , Q 3 are hydrogen or a hydroxyethyl group -C ⁇ -CH- j -OH. or a hydroxyethyloxyethyl group -CH 2 -CH 2 -0-C__ -C__ -0H 2, identical or different, under the sole condition that they are not all hydrogen.
  • the object of the invention is also to apply these cationactive compositions, in particular to the manufacture of bituminous emulsions based on amino emulsifiers.
  • the use of the compounds according to the invention gives this manufacture a new and original character, in that the emulsifiers can be prepared, stored and used for emp re. particularly troublesome in this industry, in particular those of the automation of installations which require liquid phases, those of the physical or chemical alteration of the emulsifiers, as they are or formulated, during their storage or their handling.
  • the use at room temperature of aqueous phases based on the compositions according to the invention also makes it possible to successfully emulsify hard bitumens in industrial installations working at atmospheric pressure, thanks to the reduction in the supply of calories by the phase aqueous.
  • the physical behavior of the various compounds and products according to the invention is compared here after exposure to low temperatures.
  • a so-called freeze-freeze test is carried out, during which the product contained in a test tube is subjected to intense cooling by immersing it in a cold acetone-dry ice bath. The temperature reduction within the product is followed, and the temperature Tf at which the product freezes is noted. The tube is spontaneously warm up to the atmosphere. the temperature Tdf is then noted at which a start of melting is observed.
  • the appearance of the product stored under normal laboratory temperature conditions is observed, after exposure of 12 hours at 0 ° C, and after prolonged exposure of 7 days at this temperature of 0 ° C.
  • the behavior of some representative cationic compositions is described.
  • crusty compounds are observed here by exposure to air. These compounds are mainly due to the formation of carbamates and incidentally hydrates by reaction with carbon dioxide and humidity of the atmosphere. These are substances of ill-defined composition, and which are both solid and insoluble in the amine from which they come.
  • arss ance a ra on the atmosphere is the property of oxyalkylated amines and branched chain etheramines, and that the compositions containing significant proportions of unstable cationic products remain unstable in the atmosphere.
  • solutions have been made, as is often done in the cationic bitumen emulsion industry, titrating 5 kg of the amino derivative per m of solution, starting by dispersing the cationactive composition in the water previously carried at about 60 ° C, then adding commercial hydrochloric acid in sufficient quantity for the pH to be fixed at 2, then abandoning the solution on ambient cooling.
  • the solutions are observed after standing for 24 hours.
  • alkyldiamines of the SPDA or OPDA type always give, after cooling, moire solutions, which allow their active material to deposit in the form of insoluble chlohydrates; that SPDA-2.0P gives cloudy solutions with slight deposit.
  • composition according to the invention such as consisting of 60% of OPDA-1, 5.0E and 40% of iC 13 0PPDA, gives a stable emulsion which does not change significantly when the operation is continued .
  • Preparation cold hydrochlorides solutions alkylaminées substances as dispersing phase for the preparation of bitumen emulsions 1 routiers.Dans This example presents the results obtained in achieving solutions of cation-active compositions at a concentration of 5 kg of active compound per ton or m 3 of solution; Such solutions are commonly used as dispersing phase 1 for the preparation of road bitumen emulsions. But here instead of proceeding to 60 "C as is usual in this industry, one proceeds in the absence of any heating: one cationactive in water taken at room temperature, then slowly add the appropriate amount of commercial hydrochloric acid so that the pH is fixed at 2.
  • N-ALKIZ With N-ALKIZ, dispersion in cold water is difficult and incomplete. The appearance of the mass improves slowly after addition of 11.25 liters of hydrochloric acid per m 3 . An acceptably homogeneous and clear aqueous phase is obtained only after about twenty minutes of stirring.
  • composition according to the invention comprising 50% of OPDA-2.0E and 50% of iC 13 -0PPDA, the dispersion in cold water is immediate, and after addition of 7.5 liters of commercial hydrochloric acid by m 3 , an absolutely clear aqueous phase is obtained almost instantaneously.
  • Concentrated aqueous solutions There are various indisputable advantages in preparing the most concentrated possible aqueous solutions of cationic active amino derivatives, which are and remain homogeneous, all the more so, which show no sign of gelation, and are therefore instantly pumpable, and instantly dilutable. Cold.
  • the solutions thus obtained are stored indefinitely. They can be diluted, for example, with 24 volumes of acidified water at the same pH of 2: a solution titrating 0.5% of cationic compounds, which is identical in appearance, is very easily obtained. to the solution of composition close to example 5 obtained by direct route.
  • solutions with the same concentration of 12.5% are made with SPDAM, the solution produced when hot is clear when it returns to ambient temperature; it remains so for 24 hours after its preparation, but a deposit forms after 48 hours.
  • the cold solution encounters some difficulties due to the start of gelation, which vanish as soon as the acid is added; however, only a cloudy solution is obtained, which deposits in less than 24 hours xemp e
  • the products according to the invention can be used for the manufacture of road bitumen emulsions.
  • the example relates to conventional emulsions for surface coatings, titrating 60% of bitumen, and which is obtained according to a process well known to those skilled in the art which consists in forcing together in a turbomixer the bitumen at a temperature of 1 'order of 140 ° C and a dispersing phase consisting of a hydrochloric solution of an emulsifier suitably chosen.
  • Example 7 The procedure is as in Example 7 for the comparison of emulsions produced with SPDA and with the composition C_- according to the invention, but unlike the previous example, aqueous phases are used which have been left standing for 48 hours and only the supernatant was removed. This simulates an industrial manufacture made from aqueous phases prepared in advance and which could have aged by separation of insoluble salts from the emulsifier.
  • the manufacture of the emulsion using equipment working at atmospheric pressure requires that the aqueous phase is at the maximum at a temperature of 30 ° C.
  • the attempt made in this direction with an aqueous phase made with SPDA fails totally.
  • the emulsion produced with composition C ⁇ according to the invention provides an emulsion with good characteristics, comparable to those obtained from SPDA under pressure. The results are presented below.
  • An emulsion is produced with an aqueous phase obtained by diluting a concentrated preparation.
  • the targeted emulsion is an emulsion with 60% of bitumen turbinated under the usual conditions, bitumen 180-220 at 135 ° C for 60%, and aqueous phase at 55 ° C with 0.5% of composition Cl made, ie normally by dissolution of the necessary quantity of the cationactive composition in water and acidification, either by dilution of a concentrated composition prepared as in Example 6, and resumed seven days later.
  • a 0.2% emulsion of the composition C 2 as cold produced in Example 5 and similarly used cold is compared for this purpose, the bitumen remaining as previously used at its normal temperature of 135 °, and a emulsion of the same composition produced under standard conditions.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Dispersion Chemistry (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Materials Engineering (AREA)
  • Colloid Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Medicines Containing Antibodies Or Antigens For Use As Internal Diagnostic Agents (AREA)
  • Medicines Containing Material From Animals Or Micro-Organisms (AREA)
EP89904093A 1988-03-30 1989-03-28 Kationenaktive zusammensetzungen; ihre verwendung für bituminöse emulsionen Pending EP0374205A1 (de)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
FR8804166 1988-03-30
FR8804166A FR2629364B1 (fr) 1988-03-30 1988-03-30 Nouvelles compositions amines cationactives a proprietes physiques ameliorees : leur application, par exemple a la realisation d'emulsions bitumineuses

Publications (1)

Publication Number Publication Date
EP0374205A1 true EP0374205A1 (de) 1990-06-27

Family

ID=9364781

Family Applications (2)

Application Number Title Priority Date Filing Date
EP89904093A Pending EP0374205A1 (de) 1988-03-30 1989-03-28 Kationenaktive zusammensetzungen; ihre verwendung für bituminöse emulsionen
EP89400857A Expired - Lifetime EP0340054B1 (de) 1988-03-30 1989-03-28 Kationaktive Zusammensetzungen; Verwendung für bituminöse Emulsionen

Family Applications After (1)

Application Number Title Priority Date Filing Date
EP89400857A Expired - Lifetime EP0340054B1 (de) 1988-03-30 1989-03-28 Kationaktive Zusammensetzungen; Verwendung für bituminöse Emulsionen

Country Status (13)

Country Link
US (1) US5098604A (de)
EP (2) EP0374205A1 (de)
JP (1) JPH02504486A (de)
AT (1) ATE84989T1 (de)
AU (1) AU615056B2 (de)
DE (1) DE68904589D1 (de)
ES (1) ES2054044T3 (de)
FI (1) FI895731A0 (de)
FR (1) FR2629364B1 (de)
HU (1) HUT53823A (de)
OA (1) OA09146A (de)
RU (1) RU1817703C (de)
WO (1) WO1989009089A1 (de)

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5242492A (en) * 1991-05-13 1993-09-07 Asphalt Technology & Consulting, Inc. Microsurfacing system
DE69614128D1 (de) * 1995-10-09 2001-08-30 Kao Corp Flüssige aminverbindung und damit hergestellte bitumen-emulgator
FR2760198B1 (fr) * 1997-02-28 1999-04-16 Ceca Sa Emulsifiant pour composer des emulsions bitumeuses acides enrobant tous les materiaux, y compris calcaires
JP3330309B2 (ja) * 1997-09-01 2002-09-30 花王株式会社 瀝青質乳化剤用液状アミン組成物
US6494944B1 (en) * 2000-03-02 2002-12-17 Akzo Nobel N.V. Amine oxides as asphalt emulsifiers
US7547805B2 (en) * 2004-02-17 2009-06-16 Exxonmobil Research And Engineering Company Catalytic preparation of severely sterically hindered amino-ether alcohols using a metal loaded catalyst
US7524990B2 (en) * 2004-02-17 2009-04-28 Exxonmobil Research And Engineering Company Synthesis of sterically hindered secondary aminoether alcohols
US7538251B2 (en) * 2004-02-17 2009-05-26 Exxonmobil Research And Engineering Company Synthesis of severely sterically hindered secondary aminoether alcohols from a ketene and/or carboxylic acid halide and/or carboxylic acid anhydride
JP4682157B2 (ja) * 2004-02-17 2011-05-11 エクソンモービル リサーチ アンド エンジニアリング カンパニー 高活性粉末触媒を用いる高度立体障害アミノ−エーテルアルコールおよびジアミノポリアルケニルエーテルの改良合成
EP1718598B1 (de) * 2004-02-17 2013-10-02 ExxonMobil Research and Engineering Company Synthese von sterisch gehinderten sekundären aminoetheralkoholen aus säureanhydrid und/oder säurehalogenid und schwefeltrioxid
CA2556766C (en) * 2004-02-17 2012-10-23 Exxonmobil Research And Engineering Company Synthesis of sterically hindered secondary aminoether alcohols
US7193318B2 (en) * 2004-08-18 2007-03-20 International Business Machines Corporation Multiple power density chip structure
US7238230B1 (en) * 2006-01-20 2007-07-03 Tomah Products, Inc. Asphalt-based coating compositions and salt surfactants
US11371151B2 (en) * 2018-09-06 2022-06-28 Ecolab Usa Inc. Oleyl propylenediamine-based corrosion inhibitors
CN117343713B (zh) * 2023-12-06 2024-03-22 成都理工大学 一种广谱高活性的改性剂、纳米片驱油剂及其制备方法

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DE1072915B (de) * 1956-05-25 1960-01-07 Societe Chimique Et Routiere De La Gironde, Paris Herstellung einer kalt einbaufähigen, kationischen, wäßrigen Emulsion auf Basis von Verschnittbitumen
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Also Published As

Publication number Publication date
DE68904589D1 (de) 1993-03-11
FR2629364B1 (fr) 1990-11-30
FR2629364A1 (fr) 1989-10-06
ES2054044T3 (es) 1994-08-01
AU615056B2 (en) 1991-09-19
RU1817703C (ru) 1993-05-23
EP0340054A1 (de) 1989-11-02
ATE84989T1 (de) 1993-02-15
HU892217D0 (en) 1990-11-28
FI895731A7 (fi) 1989-11-29
FI895731A0 (fi) 1989-11-29
US5098604A (en) 1992-03-24
OA09146A (fr) 1991-10-31
HUT53823A (en) 1990-12-28
WO1989009089A1 (fr) 1989-10-05
JPH02504486A (ja) 1990-12-20
EP0340054B1 (de) 1993-01-27
AU3412689A (en) 1989-10-16

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