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WO2001000734A1 - Utilisation d'emulsifiants - Google Patents

Utilisation d'emulsifiants Download PDF

Info

Publication number
WO2001000734A1
WO2001000734A1 PCT/EP2000/005668 EP0005668W WO0100734A1 WO 2001000734 A1 WO2001000734 A1 WO 2001000734A1 EP 0005668 W EP0005668 W EP 0005668W WO 0100734 A1 WO0100734 A1 WO 0100734A1
Authority
WO
WIPO (PCT)
Prior art keywords
aminophenyl
fatty acid
polymers
use according
quaternized
Prior art date
Application number
PCT/EP2000/005668
Other languages
German (de)
English (en)
Inventor
Joaquin Bigorra Llosas
Maria Escoda
Rafael Pi Subirana
Original Assignee
Cognis Deutschland Gmbh
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 Cognis Deutschland Gmbh filed Critical Cognis Deutschland Gmbh
Priority to AU52221/00A priority Critical patent/AU5222100A/en
Priority to DE50001337T priority patent/DE50001337D1/de
Priority to AT00936898T priority patent/ATE233298T1/de
Priority to EP00936898A priority patent/EP1189990B1/fr
Publication of WO2001000734A1 publication Critical patent/WO2001000734A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
    • C10L—FUELS NOT OTHERWISE PROVIDED FOR; NATURAL GAS; SYNTHETIC NATURAL GAS OBTAINED BY PROCESSES NOT COVERED BY SUBCLASSES C10G, C10K; LIQUEFIED PETROLEUM GAS; ADDING MATERIALS TO FUELS OR FIRES TO REDUCE SMOKE OR UNDESIRABLE DEPOSITS OR TO FACILITATE SOOT REMOVAL; FIRELIGHTERS
    • C10L1/00—Liquid carbonaceous fuels
    • C10L1/32—Liquid carbonaceous fuels consisting of coal-oil suspensions or aqueous emulsions or oil emulsions
    • C10L1/328—Oil emulsions containing water or any other hydrophilic phase

Definitions

  • the invention is in the field of bitumen emulsions and relates to new emulsifiers for the production of bitumen emulsions and the use of cation polymers as additives for the production of such preparations.
  • Bitumen is a dark-colored, semi-solid to hard, meltable, high-molecular hydrocarbon mixture obtained during the gentle processing of petroleum. Usually it is a colloidal system, especially brine, in an oily matrix (Maltene) dark, resin or carbon-like particles with molar Contain masses in the range of about 300 to 3000, which are referred to as asphaltenes.
  • Aqueous bitumen emulsions are mainly used in road construction. Diamines, for example N-stearylpropylene diamine, or fatty acid amidoamines, such as, for example, tallow fatty acid amidopropylamine, have proven to be suitable as emulsifiers for this purpose.
  • bitumen emulsions When producing bitumen emulsions, there are basically two different types of processes: If the bitumen is to be processed directly on site, it is important that the open time, ie the time until setting, is as short as possible. In practice, this means that the bitumen emulsion should break as quickly as possible when it comes into contact with the fillers; in this context one also speaks of a high breaking speed. In the second case, the bitumen emulsion is produced in the factory, so that, conversely, one is interested in a large open time so that the bitumen does not set during transport. The lowest possible breaking speed is desired here.
  • a simple test procedure has been established to characterize the breaking speed of a bitumen emulsion: 100 g of a bitumen emulsion are added under strong shear until fillers are added until the emulsion breaks, ie the water separates out. The fracture index is then calculated from the weight ratio of added filler to emulsion multiplied by a factor of 100. The higher the proportion of filler, the "slower" the emulsion, ie the lower the breakage speed. So far, the only possibility is the breakage speed to control a bitumen emulsion roughly by the nature of the emulsifier and its amount, therefore the object of the present invention was to provide emulsifiers which can be used to adjust the breaking rate as required. Description of the invention
  • the invention relates to the use of emulsifiers containing
  • Fatty acid amidoamines are known fatty substances which can be obtained by the relevant processes in organic chemistry. Fatty acids are preferably condensed together with polyvalent amines and the water of reaction is continuously removed from equilibrium. As a rule, the fatty acid amidoamines follow the formula (I)
  • R 1 CO represents a linear or branched, saturated or unsaturated acyl radical
  • R 2 and R 3 independently of one another represent hydrogen or an alkyl radical having 1 to 3 carbon atoms and n represents numbers from 1 to 10.
  • Typical examples are fatty acid, the fatty acid component is nol Listere of caproic acid, caprylic acid, 2-ethylhexanoic acid, capric acid, lauric acid, isotridecanoic acid, myristic acid, palmitic acid, palmitoleic acid, stearic acid, isostearic acid, oleic acid, elaidic acid, petroselinic acid, Li, linolenic acid, eleostearic acid, arachidonic acid, gadoleic , Behenic acid and erucic acid and their technical mixtures.
  • ethylenediamine N-methylethylenediamine, N, N-dimethylethylenediamine, propylenediamine, N-methylpropylenediamine, NN-dimethylpropylenediamine, butylenediamine, N-methyl-butylenediamine, N, N, dimethylbutylenediamine, pentylenediamine, pentylenediamine N, N, dimethylpen-tylenediamine, He- xylenediamine, N-methylhexylenediamine, N, N, dimethylhexylenediamine, heptylenediamine, N-methylheptylenediamine, N, N, dimethylheptylenediamine, octylenediamine, N-methyloctylenediamine, NNDimethyloctylenediamine, nonylenediamine, dimethylnonylenediamine, N-methyl
  • Fatty acid amidoamines of the formula (I) are preferably used, in which R 1 CO represents the acyl radical of coconut fatty acid, tallow fatty acid and partially hydrogenated tallow fatty acid and / or R 2 and R 3 is methyl and n is 3.
  • Suitable cationic polymers are, for example, cationic cellulose derivatives, e.g. a quaternized hydroxyethyl cellulose available under the name Polymer JR 400® from Amerchol, cationic starch, copolymers of diallyl ammonium salts and acrylamides, quaternized vinyl pyrrolidone / vinyl imidazole polymers such as e.g. Luviquat® (BASF), condensation products of polyglycols and
  • Amines such as, for example, lauryldimonium hydroxy propyl hydrolyzed collagen (Lamequat®L / Grünau), quaternized wheat polypeptides, polyethyleneimine, cationic silicone polymers, such as, for example, amidomethicones, copolymers of adipic acid and dimethylaminohydroxypropyldiethylenetriamine (sand) diethylenetriamine (sand) Acrylic acid with dimethyldiallylammonium chloride (Merquat® 550 / Chemviron), cholinates, polyaminopolyamides, as described, for example, in FR 2252840 A and their crosslinked water-soluble polymers, cationic chitin derivatives such as, for example, quaternized chitosan, optionally microcrystalline, condensation products from dihaloalkylene len, such as, for example, dibromobutane with bisdialkylamines, such as, for example,
  • the emulsifiers are used in amounts of 0.15 to 1% by weight, based on the bitumen emulsions.
  • the aqueous emulsifier solution and the bitumen from separate tanks are preferably placed in a mixing apparatus in which the homogenization takes place under strong shear.
  • a mixing apparatus for example, an Ultra-Turrax or a colloid mill are suitable for this purpose.
  • the emulsifiers are usually heated to 50 to 70 ° C., while the bitumen has temperatures above 120 and preferably from 140 to 150 ° C. for reasons of processability and pumpability.
  • the resulting emulsion generally has a mixing temperature in the range of 60 to 90 ° C.
  • bitumen emulsions allow the breaking rate to be controlled, ie the setting of a defined breaking index, and leads to an improvement in the stability of the emulsions.
  • Another object of the invention therefore relates to the use of cation polymers as auxiliaries for the preparation of bitumen emulsions in which they - preferably together with fatty acid amidoamines - in amounts of 0.05 to 0.5 and in particular 0.1 to 0.2 wt. -% - based on the emulsions - may be included.
  • Example H 540 g (2 mol) of tallow fatty acid and 1 g of hypophosphoric acid were placed in a 1 liter three-necked flask equipped with a stirrer, reflux condenser and distillation head at 70 ° C. The temperature was raised to 140 ° C. and 218 g (2.1 mol) of dimethylaminopropylamine (DAPA) were then added in portions over the course of 2 hours. The mixture was then kept at 200 ° C. for 3 hours and the water of condensation was continuously separated until the reaction product had an acid number below 5 mg KOH / g. The temperature was then reduced to 160 ° C. and unreacted DAPA was distilled off in vacuo.
  • DAPA dimethylaminopropylamine
  • A acrylamide-diallylammonium chloride copolymer
  • B acrylamide-acrylcholinate copolymer

Landscapes

  • Chemical & Material Sciences (AREA)
  • Oil, Petroleum & Natural Gas (AREA)
  • Engineering & Computer Science (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • General Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
  • Emulsifying, Dispersing, Foam-Producing Or Wetting Agents (AREA)
  • Agricultural Chemicals And Associated Chemicals (AREA)
  • Cosmetics (AREA)
  • Polyamides (AREA)

Abstract

L'invention concerne l'utilisation d'émulsifiants contenant (a) des amidoamines d'acides gras et (b) des polymères cationiques pour la production d'émulsions aqueuses de bitume.
PCT/EP2000/005668 1999-06-29 2000-06-20 Utilisation d'emulsifiants WO2001000734A1 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
AU52221/00A AU5222100A (en) 1999-06-29 2000-06-20 Utilization of emulsifiers
DE50001337T DE50001337D1 (de) 1999-06-29 2000-06-20 Verwendung von emulgatoren
AT00936898T ATE233298T1 (de) 1999-06-29 2000-06-20 Verwendung von emulgatoren
EP00936898A EP1189990B1 (fr) 1999-06-29 2000-06-20 Utilisation d'emulsifiants

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE19929962.5 1999-06-29
DE19929962A DE19929962C2 (de) 1999-06-29 1999-06-29 Verwendung von Emulgatoren

Publications (1)

Publication Number Publication Date
WO2001000734A1 true WO2001000734A1 (fr) 2001-01-04

Family

ID=7913055

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2000/005668 WO2001000734A1 (fr) 1999-06-29 2000-06-20 Utilisation d'emulsifiants

Country Status (6)

Country Link
EP (1) EP1189990B1 (fr)
AT (1) ATE233298T1 (fr)
AU (1) AU5222100A (fr)
DE (2) DE19929962C2 (fr)
ES (1) ES2193084T3 (fr)
WO (1) WO2001000734A1 (fr)

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7922802B2 (en) 2005-11-03 2011-04-12 Cognis Ip Management Gmbh PIT emulsions
US9868856B2 (en) 2014-12-05 2018-01-16 Akzo Nobel Chemicals International B.V. Polymer stabilizers for bituminous emulsions
FR3148031A1 (fr) 2023-04-24 2024-10-25 Arkema France Agents stabilisants pour compositions bitumineuses

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10224847B4 (de) * 2002-06-05 2006-04-13 Clariant Gmbh Umsetzungsprodukte aus Mischungen langkettiger Fettsäuren und aliphatischen Diaminen und deren Verwendung
EP2083050A1 (fr) 2008-01-22 2009-07-29 Cognis IP Management GmbH Compositions pour construction de route
GB201707556D0 (en) * 2017-05-11 2017-06-28 Quadrise Int Ltd Oil-in water emulsions

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2525618A1 (fr) * 1982-04-26 1983-10-28 Westvaco Corp Emulsion bitumineuse cationique
US5019610A (en) * 1990-10-18 1991-05-28 Sherex Chemical Company, Inc. Process for the production of polymer-modified asphalts and asphalts emulsions
US5242492A (en) * 1991-05-13 1993-09-07 Asphalt Technology & Consulting, Inc. Microsurfacing system
US5328505A (en) * 1992-10-16 1994-07-12 Westvaco Corporation Cationic aqueous bituminous aggregate slurries for hot climates

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE1769804C3 (de) * 1967-07-19 1975-09-11 Kao Soap Co., Ltd., Tokio Asphalt-in-Wasser-Emulsion
DD291330A5 (de) * 1990-01-03 1991-06-27 "Otto Grotewohl" Boehlen,De Verfahren zur brechzeitregulierung nichtionogener und kationaktiver bitumenemulsionen
US5362314A (en) * 1992-06-15 1994-11-08 Exxon Chemical Patents, Inc. Additive modified bituminous emulsions

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2525618A1 (fr) * 1982-04-26 1983-10-28 Westvaco Corp Emulsion bitumineuse cationique
US5019610A (en) * 1990-10-18 1991-05-28 Sherex Chemical Company, Inc. Process for the production of polymer-modified asphalts and asphalts emulsions
US5242492A (en) * 1991-05-13 1993-09-07 Asphalt Technology & Consulting, Inc. Microsurfacing system
US5328505A (en) * 1992-10-16 1994-07-12 Westvaco Corporation Cationic aqueous bituminous aggregate slurries for hot climates

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US7922802B2 (en) 2005-11-03 2011-04-12 Cognis Ip Management Gmbh PIT emulsions
US9868856B2 (en) 2014-12-05 2018-01-16 Akzo Nobel Chemicals International B.V. Polymer stabilizers for bituminous emulsions
FR3148031A1 (fr) 2023-04-24 2024-10-25 Arkema France Agents stabilisants pour compositions bitumineuses
WO2024224014A1 (fr) 2023-04-24 2024-10-31 Arkema France Agents stabilisants pour compositions bitumineuses

Also Published As

Publication number Publication date
DE19929962C2 (de) 2002-11-14
EP1189990A1 (fr) 2002-03-27
ATE233298T1 (de) 2003-03-15
AU5222100A (en) 2001-01-31
ES2193084T3 (es) 2003-11-01
DE50001337D1 (de) 2003-04-03
EP1189990B1 (fr) 2003-02-26
DE19929962A1 (de) 2001-01-11

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