EP1485433A1 - Zusammensetzungen auf basis von wässrigen dispersionen von bitumen und polyurethanen, verfahren zur herstellung und verwendung - Google Patents

Zusammensetzungen auf basis von wässrigen dispersionen von bitumen und polyurethanen, verfahren zur herstellung und verwendung

Info

Publication number
EP1485433A1
EP1485433A1 EP02801168A EP02801168A EP1485433A1 EP 1485433 A1 EP1485433 A1 EP 1485433A1 EP 02801168 A EP02801168 A EP 02801168A EP 02801168 A EP02801168 A EP 02801168A EP 1485433 A1 EP1485433 A1 EP 1485433A1
Authority
EP
European Patent Office
Prior art keywords
polyurethane
bitumen
dispersion
aqueous
composition according
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.)
Withdrawn
Application number
EP02801168A
Other languages
English (en)
French (fr)
Inventor
Evelyne Bonnet
Laurent Martin
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.)
Arkema SA
Original Assignee
Atofina 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 Atofina SA filed Critical Atofina SA
Publication of EP1485433A1 publication Critical patent/EP1485433A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C7/00—Coherent pavings made in situ
    • E01C7/08—Coherent pavings made in situ made of road-metal and binders
    • E01C7/18—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders
    • E01C7/26—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders mixed with other materials, e.g. cement, rubber, leather, fibre
    • E01C7/265—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders mixed with other materials, e.g. cement, rubber, leather, fibre with rubber or synthetic resin, e.g. with rubber aggregate, with synthetic resin binder
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L95/00—Compositions of bituminous materials, e.g. asphalt, tar, pitch
    • E—FIXED CONSTRUCTIONS
    • E01—CONSTRUCTION OF ROADS, RAILWAYS, OR BRIDGES
    • E01C—CONSTRUCTION OF, OR SURFACES FOR, ROADS, SPORTS GROUNDS, OR THE LIKE; MACHINES OR AUXILIARY TOOLS FOR CONSTRUCTION OR REPAIR
    • E01C7/00—Coherent pavings made in situ
    • E01C7/08—Coherent pavings made in situ made of road-metal and binders
    • E01C7/18—Coherent pavings made in situ made of road-metal and binders of road-metal and bituminous binders
    • E01C7/185—Isolating, separating or connecting intermediate layers, e.g. adhesive layers; Transmission of shearing force in horizontal intermediate planes, e.g. by protrusions
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
    • C08L75/04—Polyurethanes
    • C08L75/14—Polyurethanes having carbon-to-carbon unsaturated bonds

Definitions

  • the present invention relates to the field of emulsion bitumens, in particular to the field of emulsion bitumens (aqueous dispersion) modified by an aqueous polymer dispersion and more particularly to the field of emulsion bitumens modified by an aqueous dispersion of specific polyurethane.
  • bitumen-polymer mixtures are widely known, particularly in the road sector and in the field of waterproofing, in particular in the form of membranes and coatings.
  • the incorporation of polymers in bitumens changes their properties in the
  • bitumen emulsions Among the various industrial applications of bitumen emulsions, mention may, for example, be made of surface coatings, waterproofing layers under asphalt mixes, asphalt mixes, poured mixes
  • bituminous product in an aqueous phase obtained with the aid of a surfactant and thanks to an energy supply provided either by a colloid mill or by any other device capable of ensuring dispersion.
  • a surfactant provided either by a colloid mill or by any other device capable of ensuring dispersion.
  • anionic aqueous emulsions there are two types of emulsions: anionic aqueous emulsions and cationic aqueous emulsions.
  • the first (ie anionic) generally find their applications in building and public works (BTP) or construction and civil engineering works, for waterproofing, bonding and exterior protective coatings. They are particularly widely used in the field of roof waterproofing (flat roofs and built-up roofs).
  • the essential properties for these applications are the elasticity of bitumen, good resistance to high temperature (low creep) and to low temperatures (resistance to cracking), as well as good adhesion on steel and concrete substrate and low absorption of 'water (ie good impermeability).
  • bitumens used in waterproofing roofs must withstand large temperature differences in the seasonal cycle over lifetimes of several years.
  • Bitumens in emulsion not modified by a polymer additive in general do not allow sufficient performance to be obtained.
  • the mechanical properties of bitumens are very sensitive to temperature. They often become too rigid and fragile at winter temperatures, while they tend to creep at high temperatures, for example in summer.
  • bitumens generally have poor adhesion to conventional substrates such as concrete and steel. Often the application of a primer coat is therefore necessary, which involves additional production costs. Finally, their impermeability and their resistance to chemical attacks are often insufficient.
  • the second (ie cationic) are generally used as a binder in the production or repair of road surfaces.
  • the properties that we seek to improve are then the resistance to rutting (that is to say the ability of the bitumen to resist abrasion, creep and aging induced by the passage of vehicles), resistance to cracking at low temperatures as well as adhesion to aggregates.
  • US 4,724,245 describes a process which consists in preparing a mixture of bitumen, of polybutadiene hydroxytelechelic, designated hereafter by PBHT and in emulsifying it in aqueous phase, the crosslinking occurring by addition of polyisocyanate dispersed in aqueous phase.
  • US Pat. No. 3,909,474 describes a similar process starting from a previously oxidized bitumen, the crosslinking occurring by oxidation of the PBHT.
  • US Patent 3,932,331 describes a method for rapidly breaking and hardening a bitumen emulsion by incorporating an isocyanate-terminated urethane prepolymer (NCO). When the prepolymer is added to the bitumen emulsion, this makes it impossible to store the bitumen-polymer emulsion mixture, the isocyanate reacting with the water of the emulsion.
  • NCO isocyanate-terminated urethane prepolymer
  • DE 40939151 describes a composition obtained by reacting a prepolymer with a dispersion of unsaturated olefinic compound, polyurethane or bitumen.
  • DE 4408154 describes a coating based on a bitumen emulsion containing a polyurethane prepolymer with terminal NCOs.
  • the first object of the present invention is therefore an aqueous polymer composition
  • aqueous polymer composition comprising: a) at least one aqueous dispersion of bitumen b) at least one aqueous dispersion of at least one polyurethane, this polyurethane being obtained from a polyol component comprising at least one hydroxylated polydiene.
  • Another subject of the invention is a process for preparing the composition defined according to the invention, by simple physical mixing of an aqueous dispersion of bitumen and an aqueous dispersion of polyurethane, the two emulsions being compatible.
  • This process makes it possible to modify the bitumen and improve all of its properties and therefore to offer new technical solutions in the field of waterproofing for construction, construction and civil engineering.
  • This process has the advantage of proposing a system without free isocyanate
  • bitumen-polymer film forms and hardens by simple evaporation of the water, under the ambient conditions of application.
  • a coating composition comprising at least one aqueous polymer composition as defined according to the invention.
  • Another object of the invention relates to the use of an aqueous polymer composition of the invention in the production of surface coatings, waterproofing layers under road mixes, coatings waterproofing for roofs, road mixes, cold poured or slurry mixes, agglomeration binders, pipe protection coatings, bonding layers and impregnation of carpet underlayments, sound absorbing and damping or insulating coverings.
  • the invention also relates to a method of using the aqueous polymer composition as defined according to the invention, which comprises the following steps: a) mixing at least one aqueous dispersion of bitumen and at least one aqueous dispersion at least one polyurethane as defined according to the invention, b) direct application of the mixture obtained in step a) to the object or substrate for application, c) drying / film-forming by simple evaporation of the water the three stages a) b) and c) can be carried out at the place of application and under the ambient conditions of the place of application.
  • a final object of the invention relates to finished products such as coatings, surface coatings, waterproofing layers under asphalt mixes, waterproofing coatings for roofs, asphalt mixes, cold-poured or slurry mixes, agglomeration binders, coatings for protecting pipes, bonding and impregnating layers of carpet underlayers, soundproofing and damping or insulating coatings, obtained according to the method of use of the invention or from an aqueous dispersion composition of polymer as defined according to the invention.
  • the aqueous polyurethane dispersion can be prepared according to a process described in WO 99/4894 and comprising the following steps:
  • the polyurethane component of the aqueous polymer dispersion composition according to the invention represents from 2 to 50% and preferably from 5 to 25% by weight relative to the total weight of bitumen + polyurethane, the weight being expressed as dry matter.
  • the hydroxylated polydiene is chosen from oligomers of hydroxy-telechelic conjugated dienes which can be obtained by different processes such as the radical polymerization of conjugated dienes having 4 to 20 carbon atoms in the presence of a polymerization initiator such as hydrogen peroxide or an azo compound such as azobis 2, 2 '[methyl-2 , N- (2-hydroxyethyl) propionamide] or the anionic polymerization of conjugated dienes having 4 to 20 carbon atoms in the presence of a catalyst such as naphthalene dilithium.
  • a polymerization initiator such as hydrogen peroxide or an azo compound such as azobis 2, 2 '[methyl-2 , N- (2-hydroxyethyl) propionamide]
  • a catalyst such as naphthalene dilithium
  • the polyol component of the polyurethane consists of at least 50% and preferably at least 80% by weight of at least one hydroxytelechelic conjugated diene oligomer.
  • This is preferably selected from hydroxytelechelic oligomers derived from: butadiene, isoprene, chloroprene, pentadiene-1, 3, cyclopentadiene and their mixtures.
  • the number-average molecular mass of the oligomers which can be used can vary from 500 to 15,000 and preferably from 1,000 to 3,000, the hydroxyl number expressed in milliequivalents per gram (meq / g) is from 0.5 to 5 and preferably from 0.7 to 1.8 and their viscosity is between 1,000 and 10,000 mPa.s.
  • a polydiene polyol based on - butadiene and more particularly hydroxytelechelic will be used.
  • the polydiene polyol comprises 70 to 85% by mole, preferably 80% of units 1-4 and 15 to 30%, preferably 20% of units 1-2.
  • polydienepolyols of illustration there may be mentioned polybutadiene with hydroxyl end groups, sold by Atofina under the names Polybd ® HT R45 and R20 Polybd ® LM. May also be suitable as hydroxylated polydienes hydroxylated copolymers of dienes conjugated with vinyl and / or acrylic monomers such as styrene or acrylonitrile.
  • hydroxytelechelic oligomers of butadiene epoxidized on the chain or alternatively conjugated diene oligomers may be suitable for this use. hydroxytelechelic, partially or fully hydrogenated.
  • the diol carrying at least one neutralized acid function can be diethylolpropionic acid neutralized by triethylamine.
  • a short diol can also be part of the polyol component • used for the preparation • of the polyurethane.
  • diols mention may be made of 2-ethyl 1, 3-hexanediol, N, N '(bis 2-hydroxypropyl) - aniline.
  • the amount of such a diol is advantageously between 1 and 30 parts by weight per 100 parts of polydiene with hydroxyl endings.
  • the polyisocyanate used for the preparation of the aqueous polyurethane dispersion can be an aromatic, aliphatic or cycloaliphatic polyisocyanate having at least two isocyanate functions in its molecule.
  • aromatic polyisocyanates By way of illustration of aromatic polyisocyanates, mention may be made of 4, 4 '-diphenylmethane diisocyanate (MDI), liquid modified MDIs, polymeric MDIs, 2,4- and 2,6-tolylene diisocyanate (TDI) as well as their mixtures, xylylene diisocyanate (XDI), triphenylmethane triisocyanate, tetramethylxylylene diisocyanate (TMXDI), paraphenylene diisocyanate (PPDI), naphthalene diisocyanate (NDI).
  • MDI 4, 4 '-diphenylmethane diisocyanate
  • TDI polymeric MDIs, 2,4- and 2,6-tolylene diisocyanate
  • XDI xylylene diisocyanate
  • TMXDI triphenylmethane triisocyanate
  • TMXDI tetramethylx
  • the invention preferably relates to 4, '-diphenylmethane diisocyanate and very particularly liquid modified MDIs.
  • aliphatic polyisocyanates mention will be made of hexamethylene diisocyanate (HDI) and its derivatives, trimethylhexamethylene diisocyanate.
  • IPDI isophorone diisocyanate
  • CHDI cyclohexyl diisocyanate
  • a catalyst can be added which can be chosen from the group comprising tertiary amines, imidazoles and organometallic compounds.
  • DABCO 1,4-diaza-bicyclo [2.2.2] octane
  • the amounts of catalyst can be between 0.01 and 5 parts by weight per 100 parts by weight of polyol (polydiene with hydroxyl endings and diol with acid function).
  • the amount of isocyanate is advantageously such that the NCO / OH molar ratio is greater than 1.4 and preferably between 1.5 and 2.5.
  • the OH functions are those of the hydroxylated polydiene and of the acid-functional diol and short diol.
  • the amount of diol containing neutralized acid functions is advantageously such that there are 0.2 to 2.5 carboxylate functions per polydiene chain with hydroxylated endings.
  • a solvent is necessary to allow the synthesis of the prepolymer to be carried out, this solvent having to be easy to remove in step (d).
  • methyl ethyl ketone (MEK) is used. This step (a) is carried out in conventional stirred reactors.
  • step (b) The amount of water in step (b) is such that a dispersion is obtained in step (d) containing from 20 to 60 and preferably from 30 to 50% by weight of solid matter (Dry Extract: ES ).
  • step (b) is advantageously carried out in a stirred reactor.
  • This step (b) can be carried out under pressure or not, but it is simpler to be located at atmospheric pressure.
  • the temperature of this stage can vary from ambient (20 ° C) to 80 ° C and preferably it is ambient temperature (20 ° C).
  • a chain extender in step (c) mention may be made of a diamine type extender and more particularly hydrazine in aqueous solution or ethylene diamine or isophorone diamine or hydroxylamine.
  • the elongation reaction can be carried out at a temperature ranging from ambient to 80 ° C. and preferably at ambient temperature under atmospheric pressure.
  • the lengthening of the chains in the dispersion can be monitored by volumetric assay of the isocyanate functions over time. The reaction time is of the order of 10 minutes.
  • Step (d) can be carried out for example by a distillation which is carried out in a usual device.
  • the aqueous dispersions obtained do not contain a substantial amount of solvent (preferably
  • the proportions of respective dispersions of bitumen and polyurethane are in a weight ratio ranging from 2 to 75% of dispersion, for dispersions of bitumen and polyurethane having independently variable dry extract levels in a range from 20 to 60% by weight and, preferably, from 30 to 50% by weight, of each dispersion.
  • coating compositions according to the invention can be used for the production of protective, sealing or soundproofing or damping coating or coating for road, roofing, building or in industry.
  • the following examples illustrate the invention without limiting its scope.
  • An aqueous polyurethane dispersion is typically obtained from a urethane prepolymer terminated isocyanate containing anionic functional groups (that is to say carboxylic groups) or cationic in order to allow the emulsification.
  • This prepolymer is first neutralized and dispersed in water.
  • the next step consists in increasing the molecular weight or carrying out a chain extension by the addition of a diamine to obtain a dispersion of polyurea polyurea (PUD).
  • PUD polyurea polyurea
  • aqueous emulsion bitumen with a honeycomb structure free of charge emulsion that can be used as a multipurpose coating based on bitumen for waterproofing, bonding, insulation, protection and paving
  • this aqueous dispersion of polyurethane was carried out at room temperature with a paddle stirrer with low rotation for ten minutes in the following weight proportions [ml, m2]: [0.100], [5.95], [10.90], [20.80], [50.50], [75.25], [100.0] where ml represents the mass of aqueous dispersion of polyurethane PUD and m2 the mass of bitumen emulsion. 1
  • Table 1 Evaluation of the stability of the mixture as a function of the PUD / bitumen dispersion composition, after one month of storage
  • the various PUD modified bitumen emulsions were then applied in 1 mm thick film on steel.
  • the steel substrate selected is conventional steel (low carbon mild steel) previously surface treated by shot blasting.
  • An adhesion test on steel was carried out according to the RENAULT D51 1755 standard, which consists of gluing a circular stud with a diameter of 0 20 mm to the coating using a two-component epoxy adhesive.
  • bitumen alone has only very weak adhesion on shot steel. When the rate of modifier increases, the adhesion is improved very significantly.
  • the bitumen / PUD emulsion mixture [5:95] has an adhesion at 1.38 MPa, then 3.37 MPa for [20:80] and greater than 4 MPa for [50:50] and [75:25]. The results are collated in Table 3.

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  • Engineering & Computer Science (AREA)
  • Civil Engineering (AREA)
  • Structural Engineering (AREA)
  • Chemical & Material Sciences (AREA)
  • Architecture (AREA)
  • Health & Medical Sciences (AREA)
  • Materials Engineering (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • Polyurethanes Or Polyureas (AREA)
  • Compositions Of Macromolecular Compounds (AREA)
EP02801168A 2002-02-18 2002-12-23 Zusammensetzungen auf basis von wässrigen dispersionen von bitumen und polyurethanen, verfahren zur herstellung und verwendung Withdrawn EP1485433A1 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
FR0202093 2002-02-18
FR0202093A FR2836148B1 (fr) 2002-02-18 2002-02-18 Composition aqueuse de polymere a base d'une dispersion aqueuse de bitume et d'une dispersion aqueuse de polyurethanne, procede de preparation et utilisations
PCT/FR2002/004531 WO2003070829A1 (fr) 2002-02-18 2002-12-23 Compositions a base de dispersions aqueuses de bitume et de polyurethanne, procede de preparation et utilisations

Publications (1)

Publication Number Publication Date
EP1485433A1 true EP1485433A1 (de) 2004-12-15

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EP02801168A Withdrawn EP1485433A1 (de) 2002-02-18 2002-12-23 Zusammensetzungen auf basis von wässrigen dispersionen von bitumen und polyurethanen, verfahren zur herstellung und verwendung

Country Status (7)

Country Link
US (1) US20050124736A1 (de)
EP (1) EP1485433A1 (de)
AU (1) AU2002364869A1 (de)
FR (1) FR2836148B1 (de)
NO (1) NO20043867L (de)
PL (1) PL369978A1 (de)
WO (1) WO2003070829A1 (de)

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CN106433439A (zh) * 2016-09-22 2017-02-22 佛山市科顺建筑材料有限公司 一种冷施工非固化聚氨酯防水涂料及其制备方法

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FR2844283B1 (fr) 2002-09-11 2006-10-27 Soprema Membrane a base de liant bitumineux modifie polyrethanne et procede de fabrication
AT413990B (de) * 2003-09-05 2006-08-15 Toro Bausanierungs Und Handels Verfahren zur herstellung einer abdichtung von fahrbahnen z.b. auf brücken sowie zur aufbringung eines erneuerbaren verschleissbelages
WO2008036109A2 (en) * 2006-01-23 2008-03-27 Black Tuf-Stuf, Inc. Water-based asphalt emulsion-based coatings, compositions, manufacture and applications for use
US7705068B2 (en) * 2007-09-06 2010-04-27 The Garland Company, Inc. Polyurethane dispersions in an aqueous asphalt emulsion
PL209440B1 (pl) * 2008-03-03 2011-09-30 Gorniak Piotr Dodatek modyfikujący do asfaltów i sposób wytwarzania asfaltów do produkcji mieszanek mineralno-asfaltowych o wysokim module sztywności
EP2277961A1 (de) 2009-07-02 2011-01-26 Sika, S.A.U. Beschichtungsdispersionen aus Polyacryl-Polyurethan für Dächer
CN101831854A (zh) * 2010-05-26 2010-09-15 重庆市智翔铺道技术工程有限公司 复合加筋浇筑式沥青混凝土
CN102321372B (zh) * 2011-07-07 2016-05-04 重庆特铺路面工程技术有限公司 一种水性聚氨酯环氧树脂改性乳化沥青
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PL238323B1 (pl) * 2017-07-11 2021-08-09 Politechnika Gdanska Asfalt modyfikowany elastycznymi kompozycjami poliuretanowo- gumowymi i sposób otrzymywania asfaltu modyfikowanego elastycznymi kompozycjami poliuretanowo-gumowymi
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CN113773662A (zh) * 2021-10-13 2021-12-10 山东京博石油化工有限公司 一种阴离子沥青及其制备方法
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WO2025076110A1 (en) 2023-10-02 2025-04-10 Henry Company, Llc Stable hybrid formulations of acrylic emulsion and polyurethane dispersions and applications thereof

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Also Published As

Publication number Publication date
NO20043867L (no) 2004-09-15
WO2003070829A1 (fr) 2003-08-28
PL369978A1 (en) 2005-05-02
FR2836148B1 (fr) 2004-10-08
FR2836148A1 (fr) 2003-08-22
US20050124736A1 (en) 2005-06-09
AU2002364869A1 (en) 2003-09-09

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