WO2021160957A1 - Composition bitumineuse contenant une huile époxydée - Google Patents
Composition bitumineuse contenant une huile époxydée Download PDFInfo
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- WO2021160957A1 WO2021160957A1 PCT/FR2021/050219 FR2021050219W WO2021160957A1 WO 2021160957 A1 WO2021160957 A1 WO 2021160957A1 FR 2021050219 W FR2021050219 W FR 2021050219W WO 2021160957 A1 WO2021160957 A1 WO 2021160957A1
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- bitumen
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- 0 *C(NCCN(CCN1)C1O)=O Chemical compound *C(NCCN(CCN1)C1O)=O 0.000 description 2
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- 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
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L71/00—Compositions of polyethers obtained by reactions forming an ether link in the main chain; Compositions of derivatives of such polymers
- C08L71/02—Polyalkylene oxides
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L91/00—Compositions of oils, fats or waxes; Compositions of derivatives thereof
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/30—Environmental or health characteristics, e.g. energy consumption, recycling or safety issues
- C08L2555/34—Recycled or waste materials, e.g. reclaimed bitumen, asphalt, roads or pathways, recycled roof coverings or shingles, recycled aggregate, recycled tires, crumb rubber, glass or cullet, fly or fuel ash, or slag
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2555/00—Characteristics of bituminous mixtures
- C08L2555/40—Mixtures based upon bitumen or asphalt containing functional additives
- C08L2555/80—Macromolecular constituents
Definitions
- the present invention relates to a bituminous composition comprising at least one recycled bituminous product, at least one epoxidized oil, and at least one additive for bitumen.
- the invention also relates to its method of preparation and to its use for the preparation of asphalt.
- the subject of the invention is also a mix comprising the composition according to the invention, as well as a drivable surface produced from said mix.
- the invention also relates to a composition comprising at least one recycled bituminous product and at least one epoxidized oil.
- Bitumen (or asphalt) is the heaviest portion recovered during the petroleum distillation process. Due to the diverse origins and distillation processes of such oils, the resulting bitumen can exhibit a diverse range of properties and characteristics.
- bitumen does not denote only the product obtained from petroleum by direct distillation or by distillation at reduced pressure of petroleum, but also the products obtained by extraction of pitch and tar sands, the products of oil.
- bituminous materials with carbonaceous solvents, including paraffins and waxes, as well as with solvents derived from vegetable oils, as well as foamed and semi-foamed bitumens, synthetic bitumens using renewable materials such as those described for example in applications FR2853647 A and FR2915204 A, pitches, petroleum resins or indene-coumarone resins mixed with aromatic and / or paraffinic hydrocarbons, their mixtures and mixtures of such bituminous materials with acids.
- carbonaceous solvents including paraffins and waxes
- solvents derived from vegetable oils as well as foamed and semi-foamed bitumens
- synthetic bitumens using renewable materials such as those described for example in applications FR2853647 A and FR2915204 A, pitches, petroleum resins or indene-coumarone resins mixed with aromatic and / or paraffinic hydrocarbons, their mixtures and mixtures of such bituminous materials with acids.
- bitumen is the inclusion in mixes where the bitumen is mixed with mineral aggregates which can be of various sizes, shapes and chemical natures, said bitumen fulfilling the function of binder in said mineral aggregates .
- These mixes are particularly used in the construction, repair and maintenance of sidewalks, roads, highways, parking lots or airport runways and service roads, and any other vehicle surface.
- the mineral aggregates used in mixes are generally quarry products, and are more and more often used in combination with aggregates recycled from previously manufactured mixes.
- Such recycled aggregates are known under the generic name of asphalt mix or asphalt aggregates or RAP (Reclaimed Asphalt Pavement), for example defined in the French standard AFNOR XP P98-135 of December 2001 or in the Asphalt Handbook. MS-4, 7th edition, published by the Asphalt Institute, USA.
- bituminous coatings are due to an increase in the asphaltene content. These asphaltenes are partly responsible for the hardening of the bitumen and its degraded properties. Thus, bitumens containing recycled bitumen are all the more subject to aging because they contain already aged bitumen.
- Bitumen is not a renewable product. Its extraction and production of bitumen from its initial source (crude oil) has a significant impact on the environment, impact reduced by the use of RAP. In addition, constraints on quarries make it problematic to extend existing quarries or create new quarries to expand farms.
- the aim of the present invention is to improve the aging of bitumens comprising recycled bitumen. It is known from document WO2017027096 to use compounds derived from sterols to slow down the aging of bitumens comprising a portion of recycled bitumens.
- the present invention relates to a bituminous composition
- a bituminous composition comprising:
- the invention also relates to its method of preparation and to its use for the preparation of asphalt.
- the subject of the invention is also a mix comprising the composition according to the invention, as well as a drivable surface produced from said mix.
- bituminous composition comprises a recycled bituminous product.
- bituminous product is understood to mean bitumens, as well as their mixture with fillers. organic or mineral, preferably mineral, such as sand, gravel, pebbles, aggregates.
- recycled bituminous product is understood to mean any manufactured product comprising bitumen as one of its components, said manufactured product comprising bitumen having previously been used or discarded after production.
- Non-limiting examples of such recycled bituminous products include asphalt mouldings or RAP (Reclaimed Asphalt Pavement), obtained by milling roads or other drivable surfaces, waterproofing membranes, bitumen shingles used for roofing (shingle mouldings) or RAS for reclaimed asphalt shingle), soundproofing panels, production waste, mixtures of two or more of the above.
- RAP Reclaimed Asphalt Pavement
- RAPs also include recycled mixes where the mineral aggregates are replaced in part or in whole by other common components, such as, by way of limiting examples, organic and inorganic fibers (for example glass fibers , metal or carbon, cellulose, cotton, etc.), polymers, for example polypropylenes, polyesters, poly (vinyl alcohols, polyamides, polyurethanes, polyureas, copolymers of ethylene and d vinyl acetate (EVA) and styrene-butadiene-styrene (SBS).
- organic and inorganic fibers for example glass fibers , metal or carbon, cellulose, cotton, etc.
- polymers for example polypropylenes, polyesters, poly (vinyl alcohols, polyamides, polyurethanes, polyureas, copolymers of ethylene and d vinyl acetate (EVA) and styrene-butadiene-styrene (SBS).
- EVA ethylene and d vinyl
- the bituminous composition according to the invention comprises at least one epoxidized oil, at least one additive for bitumen and only recycled bitumen. In other words, it does not contain any other bituminous products except recycled bitumen.
- bituminous composition according to the invention can also comprise non-recycled mineral aggregates.
- the composition according to the invention comprises a bitumen which is a mixture of recycled bitumen and non-recycled bitumen, that is to say fresh.
- bitumen comprises from 10 to 90% by weight of recycled bitumen, and more preferably from 20 to 80% by weight, particularly from 30 to 70% by weight, and even more preferably from 40% to 60% by weight. weight relative to the total weight of the mixture.
- Non-recycled bitumens are bitumens from different origins. First of all, we can cite bitumens of natural origin, those contained in deposits of natural bitumen, natural asphalt or tar sands.
- Non-recycled bitumens are also bitumens from the refining of crude oil. Bitumens come from atmospheric and / or vacuum distillation of petroleum. These bitumens can optionally be blown, oxidized, vis-reduced and / or deasphalted. The bitumens can be hard grade or soft grade bitumens. The different bitumens obtained by the refining processes can be combined with each other to obtain the best technical compromise. The non-recycled bitumens can also be bitumens fluxed by the addition of volatile solvents, fluxes of petroleum origin, carbochemical fluxes and / or fluxes of plant origin.
- Polymer-modified bitumens can also be used.
- polymer one can quote for example, and in an indicative and nonlimiting manner, thermoplastic elastomers such as random or block copolymers of styrene and butadiene, linear or star (SBR, SBS) or of styrene and isoprene (SIS ), optionally crosslinked, copolymers of ethylene and vinyl acetate, olefinic homopolymers and copolymers of ethylene (or propylene, or butylene), polyisobutylenes, polybutadienes, polyisoprenes, poly (vinyl chloride), rubber powder or even any polymer used for modifying bitumens, as well as their mixtures.
- an amount of polymer of 2% to 10% by weight relative to the weight of bitumen is used.
- bitumens also called clear bitumens, pigmentable or colorable. These bitumens contain little or no asphaltenes and can therefore be colored. These synthetic bitumens are based on petroleum resin and / or indene-coumarone resin and lubricating oil as described for example in patent EP179510.
- the non-recycled bitumen is a bitumen of penetrability measured according to standard NF EN 1426 of June 2007 ranging from 10 to 300, preferably from 20 to 220, more preferably from 70 to 220.
- the non-recycled bitumen present in the bituminous composition according to the invention is chosen from unmodified crude oil refining bitumens.
- bituminous composition according to the invention comprising non-recycled bitumen can also comprise non-recycled mineral aggregates.
- the bitumen whether or not it is recycled, can be in anhydrous form, in the form of an emulsion or in the form of a foam.
- bituminous composition according to the invention comprises at least one epoxidized oil.
- epoxidized oil means an oil comprising at least one epoxy function.
- the epoxidized oil is chosen from epoxidized fatty acid monoesters, epoxidized fatty acid diesters, epoxidized fatty acid triesters and a mixture thereof, preferably epoxidized fatty acid diesters, epoxidized fatty acid triesters and their mixture, more particularly, epoxidized fatty acid triesters.
- fatty acid preferably means acids comprising from 8 to 26 carbon atoms.
- the epoxidized oils according to the invention are generally obtained by partial or total epoxidation of mono or polyunsaturated oils.
- the epoxidized oils according to the invention can be mono or polyepoxidized, saturated or unsaturated.
- the epoxidized oils according to the invention are a mixture of epoxidized fatty acid monoesters, of epoxidized fatty acid diesters and of epoxidized, mono and polyepoxidized, saturated and unsaturated fatty acid triesters. More particularly, the epoxidized oils according to the invention are triesters of mono and polyepoxidized, saturated and unsaturated fatty acids.
- the epoxidized oils according to the invention are chosen from epoxidized oils derived from myristoleic acid, sapineic acid, elaic acid, vaccenic acid, linoleic acid, erucic acid, acid linolenic acid, linolelaidic acid, oleic acid, elaidic acid, arachidonic acid, palmitoleic acid.
- the epoxidized oils are derived from linoleic acid, linolenic acid, oleic acid, elaidic acid, erucic acid, palmitoleic acid.
- These oils can contain diglycerides or triglycerides.
- the alcohol functions of glycerol reacted with the acid function of minus a mono or polyunsaturated fatty acid.
- Glycerol may have reacted with one unsaturated fatty acid and two saturated fatty acids, such as stearic acid, palmitic acid or lauric acid, with two unsaturated fatty acids and one saturated fatty acid, or with three fatty acids unsaturated.
- Epoxidized oils can be obtained from natural vegetable or animal oils.
- the epoxidized oils according to the invention can be obtained according to from avocado oil, coconut oil, castor oil, corn oil, cottonseed oil, coconut oil.
- the epoxidized oil present in the bituminous composition according to the invention is epoxidized soybean oil, epoxidized linseed oil and a mixture thereof.
- the bituminous composition according to the invention can comprise from 0.01% to 10%, preferably from 0.05% to 10% by weight of epoxidized oil relative to the total weight of the composition, preferably from 0 , 05 to 8% by weight, and more particularly from 0.05 to 5% by weight.
- bitumen additive included in the bituminous composition according to the invention is chosen from of formula (1) and the following compounds of formula (2):
- A is chosen from the hydrogen atom, a group G, a group
- G representing a linear or branched, saturated C1-C30 hydrocarbon chain or unsaturated, optionally comprising at least one aromatic ring, and optionally substituted by at least one phosphate group, preferably a single phosphate group,
- B represents a divalent group containing at least one repeating unit of alkylene oxide type
- Z is chosen from a hydrogen atom, a radical of formula Z1, a radical of formula Z2: where R represents the hydrogen atom or a linear or branched C1-C6 alkyl group, f is equal to 0, 1 or 2, e is equal to 0 or to 1, and d + e + f is equal to 3 , a group G, and a group G— C -, where G is as defined
- Z is chosen from a hydrogen atom, a radical of formula Z1, a radical of formula Z2, a group G, and a group G— C -, where G is as defined above,
- Z represents Z1
- e is equal to zero (0)
- P is linked to two identical or different [A-0-B-] groups, preferably identical, as defined above,
- E is chosen from the groups G, G— C -, G— P G - S -, and
- R ' is chosen from the group consisting of HO-, QO- and Q, where Q represents a linear or branched C1-C6 alkyl radical, • Y represents a group chosen from -OT, -ST, -N (H) (2-j) -T and -NT1T2, and preferably, Y represents -N (H) (2-j) -T or -NT1T2, with the proviso that Y is not -ST, when E is bonded to Y via a sulfur atom,
- T represents a hydrogen atom or a linear, branched, cyclic or group containing a cyclic group and comprising carbon and hydrogen atoms, and optionally one or more heteroatoms chosen from nitrogen, oxygen, sulfur and phosphorus, and
- the Ti and T2 radicals are identical or different and have the same value as T defined above, or together and with the nitrogen atom to which they are attached, form a saturated, partially saturated or unsaturated heterocycle, optionally further comprising one or several heteroatoms chosen from nitrogen, oxygen, sulfur and phosphorus.
- alkylene oxide preferably means butylene oxide (BO), propylene oxide (PO) or ethylene oxide (EO), it being understood that a "divalent group containing at least one repeating unit of alkylene oxide type ”is a divalent group which may include one or more repeating units BO and / or PO and / or EO.
- B represents a divalent group comprising repeating units of propylene oxide (PO) and / or ethylene oxide (EO) type, generally distributed statistically or in blocks, preferably in blocks. Even more preferably, B represents a block or random copolymer of ethylene oxide and of propylene oxide comprising between 4 and 500 repeating units, with a mass ratio (ethylene oxide / copolymer) of between 1% and 70% .
- A denotes a hydrogen atom
- B denotes a divalent group comprising repeating units of the butylene oxide (BO), propylene oxide (PO) and / or ethylene oxide (EO) type, generally distributed statistically or in blocks, preferably in blocks, d is equal to 1 and Z denotes a hydrogen atom.
- BO butylene oxide
- PO propylene oxide
- EO ethylene oxide
- A denotes a hydrogen atom
- B represents a block, alternating or random copolymer comprising one or more ethylene oxide units and / or one or more propylene oxide units, and / or a or more butylene oxide units, and comprising in total between 4 and 500 repeating units
- d is equal to 1
- Z denotes a hydrogen atom.
- A denotes a hydrogen atom
- B represents a block, alternating or random copolymer comprising one or more ethylene oxide units and one or more propylene oxide units, and comprising in total between 4 and 500 repeating units
- d is equal to 1
- Z denotes a hydrogen atom.
- Z represents Z1
- B includes and preferably represents - (CH2CH (CH3) 0) g - (CH2CH20) h- distributed statistically or in blocks, where g is between 0 and 10 and h is between 0 and 80, the sum g + h not being equal to 0, preferably between 1 and 60, and more preferably between 2 and 40.
- the additive of formula (1) can be represented by the formula A1 0 :
- g represents 0, when A contains at least 10 carbon atoms. Still in a preferred embodiment, in the additive of general formula (1), g is preferably between 1 and 80, preferably between 2 and 60, when A contains less than 10 carbon atoms.
- the groups A and Z represent the hydrogen atom and B represents a block or random copolymer of ethylene oxide and of propylene oxide comprising between 4 and 500 repeating units, with a mass ratio (ethylene oxide / copolymer) of between 1% and 70%.
- B represents a triblock copolymer, propylene oxide constituting the block of the medium.
- the additive of formula (1) can be represented by the following formula (A1 H):
- the group A represents the hydrogen atom
- d is equal to 1
- Z represents a group G or a group G— C -, where G represents a hydrocarbon chain in C1-C30
- the additive corresponds to formula (1) defined above, in which d is equal to 1, Z represents Z1, B is such
- A represents a group - P - OH.
- the additive corresponds to formula (1), in which d is equal to 2, in which case said formula (1) can be represented by formula (A12): in which the two groups (A-0-B-) are identical or different, preferably identical, the groups A and B being as defined above.
- the additive of formula (1) contains no more than 3 phosphorus atoms.
- additives of formula (1) for use in the context of the present invention may be phosphoric acid esters, such as, for example, those marketed by Lakeland Chemical under the generic name Lakeland.
- the T or T1 and T2 groups represent a group containing a polyalkylamine or a group containing an imidazolidone, imidazolidinone or imidazoline group.
- the group containing a polyalkylamine is a group derived from one of the following groups: dimethylaminopropylamine, N-amino-ethylpiperazine, diethylenetriamine, triethylenetetramine, tetraethylenepentamine, pentaethylenehexamine (PEHA), and higher homologs, such as for example the homologues higher known under the generic name of "Higher Ethylene PolyAmine" in English, better known by the acronym HEPA, and others.
- the T or Ti and T2 groups represent a group containing a group containing an imidazolidone group derived from one of the following groups: 1- (2-aminoethyl) - imidazolidin-2-one (UDETA), 1 - (2 - [(2-aminoethyl) amino] ethyl) imidazolidone (UTETA), 1 - (2- ⁇ 2 - [(2-aminoethylamino] ethyl ⁇ amino) ethyl] imidazolidone (UTEPA), 11 -mercapto-N- (2- (2-oxoimidazolidin-1 -yl) ethyl) undecanamide, 1 - (2-hydroxyethyl) - imidazolidin-2-one (HEIO), N- (6-aminohexyl) -N '- ( 6-methyl-4-oxo-1, 4-dihydro-pyrimidin-2-yl) urea (UPy
- the additive is of formula (2), in which the group E represents a group G or a group G— C -, and preferably E represents a group G , where G
- O represents a linear or branched C14-C22 hydrocarbon chain, preferably linear, saturated or partially unsaturated, preferably partially unsaturated, j is equal to 1 and Y is a polyethyleneamine.
- the additive of formula (2) can be represented by the formula E1 A: G-NH - ((CH 2 -) m-NH) kH (E1A), in which m ranges from 2 to 6 and k is from 1 to 20, preferably 1 to 15, more preferably 1 to 10, more preferably 1 to 5, preferably, m is 2, 3 or 4, more particularly, m is 2 or 3.
- the additive is represented by formula (2), in which E represents a group G— C -, where G represents
- the additive of formula (2) can be represented by the formula E1 B: G-CO-NH - ((CH 2 -) m-NH) kH (E1 B), in which G, m and k are as defined above.
- additives of formula E1 B for use in the context of the present invention can be easily obtained from Arkema France under the generic brand Cecabase ® .
- Examples of additives of formula (E1A) and formula (E1B) for use according to the present invention are available for example from Arkema France in the range Polyram ®.
- the additive is represented by formula (2), in which E represents a group G— C -,
- G represents a linear, saturated or partially unsaturated, preferably partially unsaturated, C14-C22 hydrocarbon chain
- j is equal to 1
- Y represents a radical derived from the following: 1- (2-aminoethyl) imidazolidin-2-one (UDETA ), 1- (2-hydroxyethyl) imidazolidin-2-one (HEIO) or 1- (2-mercaptoethyl) - imidazolidin-2-one.
- the additives of formula (2) can be respectively represented by the formulas E1 c, E1 D and E1 E:
- the additives defined above of formula (2) can be modified by following general methods known to those skilled in the art, such as, for example and in a nonlimiting manner, by reaction with alkylene oxides, for example EO (ethylene oxides) and / or PO (propylene oxides) and / or BO (butylene oxides); or by ionization with an inorganic or organic acid, such as hydrochloric acid, phosphoric acid, acetic acid.
- alkylene oxides for example EO (ethylene oxides) and / or PO (propylene oxides) and / or BO (butylene oxides)
- an inorganic or organic acid such as hydrochloric acid, phosphoric acid, acetic acid.
- additives modified by reaction with alkylene oxides for use in the context of the present invention are commercially available and can for example be easily obtained from Arkema France under the generic brands Noramox ® and Dinoramox ® .
- the bituminous composition according to the invention comprises a content of between 0.01% and 10% by weight, preferably between 0.05% and 10% by weight more particularly between 0.05% and 8% by weight, and even more preferably between 0.05% and 5% by weight relative to the total weight of the composition.
- the bituminous composition according to the invention can comprise a weight ratio between the epoxidized oil and the bitumen additive of between 10 / 0.5 to 1/5, preferably between 8/1 and 1/2, and more particularly between 5/1 and 1/1.
- the oil and the bitumen additive can be added to the bitumen in pure form or in diluted form, that is to say dissolved, dispersed or emulsified in a liquid.
- Liquids suitable for dissolving, dispersing or emulsifying the mixture of oil and bitumen additive can be water, organic or inorganic solvents, such as alcohols or vegetable oils or mineral. Preferably, organic solvents are preferred.
- the bituminous composition is in the form of an emulsion, comprising water and one or more emulsifiers, optionally one or more organic or mineral acids or organic or mineral bases.
- the emulsifiers can be cationic or anionic or nonionic or amphoteric or zwitterionic surfactants.
- the aging of the bituminous composition according to the invention is evaluated by measuring an aging index, denoted I, according to the following formula:
- G7sin (5) is measured using an AntonPaar MCR 301 imposed stress rheometer, referred to in English as DSR, and a plane / plane surveyor with a diameter of 25 mm and an air gap of 1 mm; the measurements are carried out by scanning the temperature from 80 to 40 ° C. at a frequency of Q1 Hz and under a strain of 1%.
- the reference temperature is 45 ° C.
- This aging index is a ratio between the values of the G7sin (5) of the thermally aged system and of the unaged system. The higher this ratio, the more the system has undergone aging, which has resulted in an increase in its modulus.
- the bituminous composition can also comprise at least one antioxidant.
- the antioxidant is defined in the work Asphalt Handbook (MS-4, 7th edition, (2017)).
- the antioxidant can be a primary antioxidant, also called a radical scavenger; a secondary antioxidant, also called preventive antioxidant or in English “hydroperoxide decomposers”; a UV absorber or else a metal deactivator, and mixtures thereof.
- the antioxidant is selected from compounds of phenolic structure, phosphite derivatives, hindered amine derivatives and anti-UV compounds.
- a primary phenolic antioxidant the compounds of the trade name Irganox ® 245 or Irganox ® 1098 and Irganox 1010 ® from Ciba can be used.
- a secondary antioxidant derivatives of hindered amine Tinuvin ® 770 from Ciba can be used.
- Naugard 445 ® from Crompton is an antioxidant derived from amines.
- Tinuvin 312 ® from Ciba can be used as an antioxidant against UV rays.
- the bituminous composition may comprise a content of between 0.01% and 10% by weight of antioxidant relative to the total weight of the composition, preferably between 0.05% and 5% by weight and more particularly between 0.05% and 2.5% by weight relative to the total weight of the composition.
- composition can also comprise one or more other additives commonly used in the field of bitumens and mixes, such additives can be chosen from the following:
- polyphosphoric acid including all the different qualities and designations existing for polyphosphoric acids, which includes pyrophosphoric acid, triphosphoric and metaphosphoric acids and phosphonic acid,
- waxes such as Fischer-Tropsch waxes, for example described in patent US6588974,
- resin-type components such as rosin acids, or modified rosin acids, tall oil pitch, pine tar pitch, pine rosins, tall oil rosins,
- organic fibers for example: cellulose, cotton, polypropylene, polyester, polyvinyl alcohol and polyamide fibers
- inorganic fibers for example: glass, metal or carbon fibers
- Non-limiting examples of polymers generally used to improve the mechanical performance of bitumens and mixtures, that is to say commonly used in the modification of bitumens, include the following: styrene-butadiene rubbers, block copolymers styrene / butadiene, ethylene / vinyl acetate copolymers, polyethylene and other alpha-polyolefins, such as for example those described in YAsphalt binder testing manual, Asphalt Institute (2007).
- the invention also relates to the process for preparing the bituminous composition according to the invention.
- This process includes a step of mixing the epoxidized oil and bitumen additive with the hot recycled bitumen.
- the composition is prepared by mixing the epoxidized oil, the additive for bitumen, and optionally the other additives present in the composition.
- the mixture is then added to the recycled bituminous product at high temperature, that is to say between 100 and 250 ° C.
- the additive and the epoxidized oil are added simultaneously to the recycled bitumen.
- the epoxidized oil, the additive for bitumen, and optionally the other additives present in the composition are added sequentially in any order, to the hot recycled bituminous product, c 'that is, between 100 ° C and 250 ° C.
- the composition is prepared by mixing the epoxidized oil, the bitumen additive, fresh bitumen and optionally other additives present in the composition. The mixture is then added to the recycled bituminous product hot, that is to say between 100 ° C and 250 ° C. In other words, the epoxidized oil, additive and fresh bitumen are added simultaneously to the recycled bitumen.
- the epoxidized oil, the additive for bitumen, the fresh bitumen and optionally the other additives present in the composition are added sequentially in any order, to the bituminous product recycled to hot, i.e. between 100 ° C and 250 ° C.
- the invention also relates to the use of the composition as defined above to prepare a mix exhibiting improved properties in terms of aging.
- a subject of the invention is also a mix comprising the composition as defined above and mineral aggregates.
- the invention also relates to a drivable surface produced from the mix defined above.
- the drivable surface can be road mats, sidewalks, airplane tracks, cycle paths, parking areas.
- the examples of applications of the present invention include the production of mixes containing mineral aggregates, said mixes being used for earthworks and waterproofing, and more specifically in the construction, repair and maintenance of sidewalks. , roads, highways, parking lots or airport runways and service roads, and any other drivable surface.
- the invention relates to a composition comprising:
- composition according to the invention can comprise:
- epoxidized oil chosen from fatty acid monoesters epoxidized, epoxidized fatty acid diesters, epoxidized fatty acid triesters and their mixture, preferably epoxidized fatty acid diesters, epoxidized fatty acid triesters and their mixture, more particularly, acid triesters epoxidized fats and
- A is chosen from the hydrogen atom
- B denotes a divalent group comprising repeating units of the butylene oxide (BO), propylene oxide (PO) and / or ethylene oxide (EO) type, generally distributed from statistically or in blocks, preferably in blocks, d is equal to 1 and Z denotes a hydrogen atom
- the group E represents a group G or a group G— C -, and preferably E represents a group G, where G represents an O linear or branched C14-C22 hydrocarbon chain, preferably linear, saturated or partially unsaturated, preferentially partially unsaturated, j is equal to 1 and Y is a polyethyleneamine.
- composition according to the invention can comprise from 10% to 95% by weight of epoxidized oil relative to the total weight of the composition, preferably from 10% to 92% by weight, more particularly from 50% to 90 % by weight, more particularly 60% to 90% by weight.
- composition according to the invention can comprise from 5% to 90% by weight of additive for bitumen relative to the total weight of the composition, preferably from 8% to 80% by weight, more particularly from 10% to 50% by weight, more particularly 10% to 40% by weight.
- composition according to the invention preferably comprises the epoxidized oil and the bitumen additive in a weight ratio of between 10: 1 and 1: 1, preferably between 8: 1 and 2: 1.
- the composition does not include a solvent.
- the composition according to the invention can be in diluted form in a solvent.
- the composition can include water, organic solvents, inorganic solvents and their mixture.
- the organic solvents can be chosen from alcohols, vegetable oils, mineral oils.
- organic solvents are preferred.
- the composition may be in the form of an emulsion.
- the composition is in emulsion form, comprising water and one or more emulsifiers, optionally one or more organic or inorganic acids or organic or inorganic bases.
- the emulsifiers can be cationic or anionic or nonionic or amphoteric or zwitterionic surfactants.
- the invention relates to the use of the composition as defined above as an additive for bitumen, and in particular as an anti-aging additive. In other words, the invention relates to the use of said composition to slow down the aging of bitumen, preferably bitumen comprising all or part of recycled bitumen.
- the composition can be added to the bitumen in a content of between 0.01% and 10% by weight, preferably between 0.05% and 10% by weight, more particularly between 0.05% and 8% by weight, and even more preferably between 0.05% and 5% by weight relative to the total weight of the bituminous product.
- the fresh bitumen is 160/200 bitumen marketed by Total and coming from the Feyzin plant.
- Recycled bitumen is a 10-20 penetrability bitumen.
- the epoxidized oil is Vikoflex ® 7170 oil marketed by the company Arkema France.
- the bitumen additives are a copolymer Ensoline ® PEG 3600 sold by the company Arkema France and one type of additive amidoamine Polyram l920 ® sold by the company Arkema France.
- the fresh bitumen, the epoxidized oil and the bitumen additive are mixed at room temperature and then heated for 30 min at 150 ° C. Then the mixture is added to the recycled bitumen. The mixture is stirred for 3 min at 400 rpm with a Raneyri type mixer. This mixture is allowed to cool to room temperature.
- a thin film film of 200 ⁇ m is produced on a metal plate. Two samples are made for each bituminous composition. The first series of samples will be used to measure unaged G7sin (5). The second set of samples will be aged, then the aged G7sin (5) will be measured.
- the first series of measurements is carried out on the samples prepared.
- the thin film film is placed on the lower plane of the plane / plane equipment of the rheometer. After adjusting the air gap, the rheology measurements are performed. This first measurement carried out on the film, before aging, is noted “not aged”.
- a second series of samples is placed for thermal aging in a ventilated oven at a temperature of 150 ° C for 2 hours.
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- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Civil Engineering (AREA)
- Materials Engineering (AREA)
- Structural Engineering (AREA)
- Engineering & Computer Science (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Lubricants (AREA)
Abstract
Description
Claims
Priority Applications (5)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US17/798,764 US20230092802A1 (en) | 2020-02-14 | 2021-02-05 | Bituminous composition containing an epoxidized oil |
EP21708721.2A EP4103651A1 (fr) | 2020-02-14 | 2021-02-05 | Composition bitumineuse contenant une huile époxydée |
CA3165163A CA3165163A1 (fr) | 2020-02-14 | 2021-02-05 | Composition bitumineuse contenant une huile epoxydee |
BR112022014226A BR112022014226A2 (pt) | 2020-02-14 | 2021-02-05 | Composição betuminosa que contém um óleo epoxidado |
AU2021219039A AU2021219039A1 (en) | 2020-02-14 | 2021-02-05 | Bituminous composition containing an epoxidized oil |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
FR2001495A FR3107278A1 (fr) | 2020-02-14 | 2020-02-14 | Composition bitumineuse contenant une huile époxydée |
FR2001495 | 2020-02-14 |
Publications (1)
Publication Number | Publication Date |
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WO2021160957A1 true WO2021160957A1 (fr) | 2021-08-19 |
Family
ID=71661947
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/FR2021/050219 WO2021160957A1 (fr) | 2020-02-14 | 2021-02-05 | Composition bitumineuse contenant une huile époxydée |
Country Status (8)
Country | Link |
---|---|
US (1) | US20230092802A1 (fr) |
EP (1) | EP4103651A1 (fr) |
AU (1) | AU2021219039A1 (fr) |
BR (1) | BR112022014226A2 (fr) |
CA (1) | CA3165163A1 (fr) |
CL (1) | CL2022002146A1 (fr) |
FR (1) | FR3107278A1 (fr) |
WO (1) | WO2021160957A1 (fr) |
Families Citing this family (1)
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CN115160467B (zh) * | 2022-06-22 | 2023-10-03 | 东南大学 | 一种新型生物基液体改性剂的制备方法及其应用 |
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EP0179510A1 (fr) | 1984-10-15 | 1986-04-30 | Shell Internationale Researchmaatschappij B.V. | Composition de liant pigmentable |
US6588974B2 (en) | 1997-08-29 | 2003-07-08 | SCHÜMANN SASOL GmbH | Bitumen or asphalt for producing a road topping, road topping and method for the production of bitumen or asphalt |
FR2853647A1 (fr) | 2003-04-08 | 2004-10-15 | Colas Sa | Liant de nature vegetale pour la realisation de materiaux pour le batiment et/ou les travaux publics |
WO2006016041A1 (fr) | 2004-07-08 | 2006-02-16 | Arkema France | Materiau polymere contenant des chaines portant des fonctions imidazolidone |
FR2915204A1 (fr) | 2007-04-23 | 2008-10-24 | Eiffage Travaux Publics Soc Pa | Composition comprenant une fraction organique pour la realisation d'une couche et/ou d'un revetement de voie ou de batiment |
WO2008148974A2 (fr) | 2007-04-26 | 2008-12-11 | Ceca S.A. | Procede de preparation d'enrobes a base de produits bitumineux et leurs utilisations |
FR2947826A1 (fr) * | 2009-07-08 | 2011-01-14 | Ceca Sa | Melange d'additifs pour la preparation d'enrobes |
US20120315088A1 (en) * | 2011-06-10 | 2012-12-13 | Colas | Vegetable-based products of the siccative type for recycling and rejuvenating reclaimed asphalt pavements in situ or in a dedicated plant |
FR2981347A1 (fr) * | 2011-10-12 | 2013-04-19 | Ceca Sa | Additive for asphalt mixtures containing reclaimed bituminous products |
WO2017027096A2 (fr) | 2015-06-10 | 2017-02-16 | A.L.M Holding Company | Utilisation de stérols comme additif dans un liant bitumineux |
CN108046663A (zh) * | 2017-12-15 | 2018-05-18 | 武汉工程大学 | 一种掺钢渣再生沥青混凝土及其制备方法 |
Family Cites Families (1)
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US6348517B1 (en) * | 2000-09-01 | 2002-02-19 | Oxy Services, Inc. | Preparing sterile articles from polymers containing a stabilizer based on a poly(oxyalkylene) |
-
2020
- 2020-02-14 FR FR2001495A patent/FR3107278A1/fr active Pending
-
2021
- 2021-02-05 EP EP21708721.2A patent/EP4103651A1/fr active Pending
- 2021-02-05 US US17/798,764 patent/US20230092802A1/en active Pending
- 2021-02-05 AU AU2021219039A patent/AU2021219039A1/en active Pending
- 2021-02-05 WO PCT/FR2021/050219 patent/WO2021160957A1/fr unknown
- 2021-02-05 BR BR112022014226A patent/BR112022014226A2/pt unknown
- 2021-02-05 CA CA3165163A patent/CA3165163A1/fr active Pending
-
2022
- 2022-08-09 CL CL2022002146A patent/CL2022002146A1/es unknown
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EP0179510A1 (fr) | 1984-10-15 | 1986-04-30 | Shell Internationale Researchmaatschappij B.V. | Composition de liant pigmentable |
US6588974B2 (en) | 1997-08-29 | 2003-07-08 | SCHÜMANN SASOL GmbH | Bitumen or asphalt for producing a road topping, road topping and method for the production of bitumen or asphalt |
FR2853647A1 (fr) | 2003-04-08 | 2004-10-15 | Colas Sa | Liant de nature vegetale pour la realisation de materiaux pour le batiment et/ou les travaux publics |
WO2006016041A1 (fr) | 2004-07-08 | 2006-02-16 | Arkema France | Materiau polymere contenant des chaines portant des fonctions imidazolidone |
FR2915204A1 (fr) | 2007-04-23 | 2008-10-24 | Eiffage Travaux Publics Soc Pa | Composition comprenant une fraction organique pour la realisation d'une couche et/ou d'un revetement de voie ou de batiment |
WO2008148974A2 (fr) | 2007-04-26 | 2008-12-11 | Ceca S.A. | Procede de preparation d'enrobes a base de produits bitumineux et leurs utilisations |
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US20120315088A1 (en) * | 2011-06-10 | 2012-12-13 | Colas | Vegetable-based products of the siccative type for recycling and rejuvenating reclaimed asphalt pavements in situ or in a dedicated plant |
FR2981347A1 (fr) * | 2011-10-12 | 2013-04-19 | Ceca Sa | Additive for asphalt mixtures containing reclaimed bituminous products |
WO2017027096A2 (fr) | 2015-06-10 | 2017-02-16 | A.L.M Holding Company | Utilisation de stérols comme additif dans un liant bitumineux |
CN108046663A (zh) * | 2017-12-15 | 2018-05-18 | 武汉工程大学 | 一种掺钢渣再生沥青混凝土及其制备方法 |
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ALEX K. APEAGYEI: "Laboratory évaluation of anti-oxydants for asphalt binders", CONSTRUCTION AND BUILDING MATERIALS, vol. 25, 2011, pages 47 - 53 |
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Also Published As
Publication number | Publication date |
---|---|
BR112022014226A2 (pt) | 2022-09-13 |
AU2021219039A1 (en) | 2022-09-01 |
CL2022002146A1 (es) | 2023-03-03 |
FR3107278A1 (fr) | 2021-08-20 |
CA3165163A1 (fr) | 2021-08-19 |
US20230092802A1 (en) | 2023-03-23 |
EP4103651A1 (fr) | 2022-12-21 |
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