EP4448632A1 - Verwendung von bisamidverbindungen zur verbesserung der alterungsbeständigkeit von bitumen - Google Patents
Verwendung von bisamidverbindungen zur verbesserung der alterungsbeständigkeit von bitumenInfo
- Publication number
- EP4448632A1 EP4448632A1 EP22835702.6A EP22835702A EP4448632A1 EP 4448632 A1 EP4448632 A1 EP 4448632A1 EP 22835702 A EP22835702 A EP 22835702A EP 4448632 A1 EP4448632 A1 EP 4448632A1
- Authority
- EP
- European Patent Office
- Prior art keywords
- aging
- bituminous composition
- bituminous
- use according
- bitumen
- 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
Links
- 230000032683 aging Effects 0.000 title claims abstract description 151
- FTQWRYSLUYAIRQ-UHFFFAOYSA-N n-[(octadecanoylamino)methyl]octadecanamide Chemical class CCCCCCCCCCCCCCCCCC(=O)NCNC(=O)CCCCCCCCCCCCCCCCC FTQWRYSLUYAIRQ-UHFFFAOYSA-N 0.000 title abstract description 35
- 239000010426 asphalt Substances 0.000 title description 77
- 239000000203 mixture Substances 0.000 claims abstract description 155
- 238000000034 method Methods 0.000 claims abstract description 35
- -1 bisamide compound Chemical class 0.000 claims description 36
- 238000011084 recovery Methods 0.000 claims description 24
- 125000004432 carbon atom Chemical group C* 0.000 claims description 18
- 229910052760 oxygen Inorganic materials 0.000 claims description 14
- 230000008569 process Effects 0.000 claims description 12
- 229930195734 saturated hydrocarbon Natural products 0.000 claims description 11
- 238000004519 manufacturing process Methods 0.000 claims description 10
- 238000005259 measurement Methods 0.000 claims description 10
- 238000009418 renovation Methods 0.000 claims description 9
- 229920006395 saturated elastomer Polymers 0.000 claims description 9
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 8
- 239000001301 oxygen Substances 0.000 claims description 8
- 230000005855 radiation Effects 0.000 claims description 8
- 238000010276 construction Methods 0.000 claims description 7
- 238000002360 preparation method Methods 0.000 claims description 7
- 125000004122 cyclic group Chemical group 0.000 claims description 6
- 125000005842 heteroatom Chemical group 0.000 claims description 6
- 230000001590 oxidative effect Effects 0.000 claims description 6
- 229910052717 sulfur Inorganic materials 0.000 claims description 6
- 229930195735 unsaturated hydrocarbon Natural products 0.000 claims description 6
- 230000015556 catabolic process Effects 0.000 claims description 4
- 238000006731 degradation reaction Methods 0.000 claims description 4
- 150000001408 amides Chemical group 0.000 claims description 3
- 125000001183 hydrocarbyl group Chemical group 0.000 claims 5
- 239000000654 additive Substances 0.000 description 32
- 150000001875 compounds Chemical class 0.000 description 17
- 150000002430 hydrocarbons Chemical class 0.000 description 17
- 230000000996 additive effect Effects 0.000 description 14
- 238000012360 testing method Methods 0.000 description 14
- 230000035882 stress Effects 0.000 description 13
- 239000000126 substance Substances 0.000 description 11
- 239000011230 binding agent Substances 0.000 description 8
- 239000000463 material Substances 0.000 description 8
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical group O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 7
- 238000005292 vacuum distillation Methods 0.000 description 7
- 230000007774 longterm Effects 0.000 description 6
- 239000000178 monomer Substances 0.000 description 6
- 238000007254 oxidation reaction Methods 0.000 description 6
- 239000010779 crude oil Substances 0.000 description 5
- 238000004821 distillation Methods 0.000 description 5
- 238000002156 mixing Methods 0.000 description 5
- 238000007670 refining Methods 0.000 description 5
- 230000008859 change Effects 0.000 description 4
- 238000006243 chemical reaction Methods 0.000 description 4
- 238000000576 coating method Methods 0.000 description 4
- 230000000052 comparative effect Effects 0.000 description 4
- 229920001971 elastomer Polymers 0.000 description 4
- 239000000806 elastomer Substances 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- 230000003647 oxidation Effects 0.000 description 4
- 229920000642 polymer Polymers 0.000 description 4
- 239000000843 powder Substances 0.000 description 4
- 239000007787 solid Substances 0.000 description 4
- 238000003756 stirring Methods 0.000 description 4
- 239000002671 adjuvant Substances 0.000 description 3
- 239000011248 coating agent Substances 0.000 description 3
- 230000006872 improvement Effects 0.000 description 3
- RKISUIUJZGSLEV-UHFFFAOYSA-N n-[2-(octadecanoylamino)ethyl]octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCCNC(=O)CCCCCCCCCCCCCCCCC RKISUIUJZGSLEV-UHFFFAOYSA-N 0.000 description 3
- 239000004576 sand Substances 0.000 description 3
- 238000003860 storage Methods 0.000 description 3
- 238000004078 waterproofing Methods 0.000 description 3
- HCILJBJJZALOAL-UHFFFAOYSA-N 3-(3,5-ditert-butyl-4-hydroxyphenyl)-n'-[3-(3,5-ditert-butyl-4-hydroxyphenyl)propanoyl]propanehydrazide Chemical compound CC(C)(C)C1=C(O)C(C(C)(C)C)=CC(CCC(=O)NNC(=O)CCC=2C=C(C(O)=C(C=2)C(C)(C)C)C(C)(C)C)=C1 HCILJBJJZALOAL-UHFFFAOYSA-N 0.000 description 2
- KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
- 241000218631 Coniferophyta Species 0.000 description 2
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 2
- 239000005977 Ethylene Substances 0.000 description 2
- PPBRXRYQALVLMV-UHFFFAOYSA-N Styrene Chemical compound C=CC1=CC=CC=C1 PPBRXRYQALVLMV-UHFFFAOYSA-N 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 239000003431 cross linking reagent Substances 0.000 description 2
- 125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 description 2
- 125000002960 margaryl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 230000004044 response Effects 0.000 description 2
- 238000007789 sealing Methods 0.000 description 2
- 230000035945 sensitivity Effects 0.000 description 2
- 239000000758 substrate Substances 0.000 description 2
- 239000010409 thin film Substances 0.000 description 2
- 238000012546 transfer Methods 0.000 description 2
- 125000002948 undecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- OXDXXMDEEFOVHR-CLFAGFIQSA-N (z)-n-[2-[[(z)-octadec-9-enoyl]amino]ethyl]octadec-9-enamide Chemical compound CCCCCCCC\C=C/CCCCCCCC(=O)NCCNC(=O)CCCCCCC\C=C/CCCCCCCC OXDXXMDEEFOVHR-CLFAGFIQSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Natural products CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 1
- 229920002943 EPDM rubber Polymers 0.000 description 1
- 239000001692 EU approved anti-caking agent Substances 0.000 description 1
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 1
- 229910000831 Steel Inorganic materials 0.000 description 1
- 229930182558 Sterol Natural products 0.000 description 1
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 1
- 239000005864 Sulphur Substances 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- 125000005250 alkyl acrylate group Chemical group 0.000 description 1
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 1
- 125000001204 arachidyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 238000009435 building construction Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 239000004568 cement Chemical group 0.000 description 1
- 238000007385 chemical modification Methods 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 238000007796 conventional method Methods 0.000 description 1
- 238000004132 cross linking Methods 0.000 description 1
- 238000007872 degassing Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 230000018109 developmental process Effects 0.000 description 1
- 150000004985 diamines Chemical class 0.000 description 1
- 125000003438 dodecyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000011156 evaluation Methods 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 229910021485 fumed silica Inorganic materials 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- VOZRXNHHFUQHIL-UHFFFAOYSA-N glycidyl methacrylate Chemical compound CC(=C)C(=O)OCC1CO1 VOZRXNHHFUQHIL-UHFFFAOYSA-N 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 230000008595 infiltration Effects 0.000 description 1
- 238000001764 infiltration Methods 0.000 description 1
- 229910052500 inorganic mineral Inorganic materials 0.000 description 1
- 238000009413 insulation Methods 0.000 description 1
- 230000002427 irreversible effect Effects 0.000 description 1
- 229920005610 lignin Polymers 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 238000012423 maintenance Methods 0.000 description 1
- 238000000691 measurement method Methods 0.000 description 1
- 230000007246 mechanism Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 239000011707 mineral Substances 0.000 description 1
- 238000012986 modification Methods 0.000 description 1
- 230000004048 modification Effects 0.000 description 1
- 125000001421 myristyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002086 nanomaterial Substances 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 125000001117 oleyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])/C([H])=C([H])\C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 125000000913 palmityl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 230000035515 penetration Effects 0.000 description 1
- 239000003208 petroleum Substances 0.000 description 1
- 238000004525 petroleum distillation Methods 0.000 description 1
- 239000011295 pitch Substances 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 238000004064 recycling Methods 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 238000005096 rolling process Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 150000004760 silicates Chemical class 0.000 description 1
- RMAQACBXLXPBSY-UHFFFAOYSA-N silicic acid Chemical class O[Si](O)(O)O RMAQACBXLXPBSY-UHFFFAOYSA-N 0.000 description 1
- 239000000377 silicon dioxide Substances 0.000 description 1
- LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
- 229910052814 silicon oxide Inorganic materials 0.000 description 1
- 238000004088 simulation Methods 0.000 description 1
- 239000008247 solid mixture Substances 0.000 description 1
- 229910001220 stainless steel Inorganic materials 0.000 description 1
- 239000010935 stainless steel Substances 0.000 description 1
- 125000004079 stearyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000010959 steel Substances 0.000 description 1
- 150000003432 sterols Chemical class 0.000 description 1
- 235000003702 sterols Nutrition 0.000 description 1
- 150000003462 sulfoxides Chemical group 0.000 description 1
- 230000002195 synergetic effect Effects 0.000 description 1
- 238000010189 synthetic method Methods 0.000 description 1
- 239000000454 talc Substances 0.000 description 1
- 229910052623 talc Inorganic materials 0.000 description 1
- 229920001897 terpolymer Polymers 0.000 description 1
- 125000002889 tridecyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000002023 wood Chemical group 0.000 description 1
Classifications
-
- 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
-
- 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
- C08K5/0008—Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
- C08K5/005—Stabilisers against oxidation, heat, light, ozone
-
- 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
- C08K5/20—Carboxylic acid amides
-
- C—CHEMISTRY; METALLURGY
- C10—PETROLEUM, GAS OR COKE INDUSTRIES; TECHNICAL GASES CONTAINING CARBON MONOXIDE; FUELS; LUBRICANTS; PEAT
- C10C—WORKING-UP PITCH, ASPHALT, BITUMEN, TAR; PYROLIGNEOUS ACID
- C10C3/00—Working-up pitch, asphalt, bitumen
- C10C3/02—Working-up pitch, asphalt, bitumen by chemical means reaction
- C10C3/026—Working-up pitch, asphalt, bitumen by chemical means reaction with organic compounds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L2201/00—Properties
- C08L2201/08—Stabilised against heat, light or radiation or oxydation
-
- 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
- C08L2555/60—Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye
- C08L2555/70—Organic non-macromolecular ingredients, e.g. oil, fat, wax or natural dye from natural non-renewable resources
Definitions
- the present invention belongs to the field of bitumens and relates to increasing the longevity of bitumen and products derived therefrom.
- the invention relates to the use of bisamide compounds to improve the aging resistance of bitumen.
- the invention also relates to a process for improving the resistance to aging of a bituminous composition.
- Bitumen or bituminous binder is the main hydrocarbon binder used in the fields of road construction and civil engineering. Bitumen is also used to seal various substrates. The quality of a bitumen, in particular for road applications, is based on its resistance to ageing, understood as resistance to change in its basic parameters.
- bitumen is a material that evolves over time and undergoes an aging process which depends on the traffic load and/or climatic influences.
- bitumen In general, the aging of bitumen takes place in two stages: first in the short term during the production of the binder or bituminous mix, storage and laying at high temperature cause degradation due to oxidation and volatilization volatile fractions contained in the bitumen, then in the long term during the service life of the pavement and/or the building and/or the support to which the bitumen is applied.
- bitumen The main factors affecting the aging of bitumen are oxidation induced by oxygen in the air, temperature variations, exposure to humidity and exposure to ultraviolet rays.
- Oxidation is the primary cause of bitumen aging, often referred to as oxidative aging. This type of aging involves irreversible chemical reactions between the components of bitumen and atmospheric oxygen. Research has shown that the oxidative aging of bitumen occurs through a chain reaction mechanism that results in an increase in the number of polar and reactive functional groups, such as carbonyl or sulfoxide functions, an increase in the products of condensation as well as the aromaticity of the bitumen and the decrease in the content of saturated compounds. A rise in temperature is also an important factor which catalyzes oxidation reactions and promotes the aging of bitumen.
- Ultraviolet rays mainly attack the upper layer of the pavement, leading to its embrittlement. This can result in heat transfer from the top layer to the base layer, which accelerates oxidation reactions within the bituminous layer.
- bitumen for example, viscoelastic properties, water impermeability, or adhesion strength, which generally makes bituminous materials harder and more brittle. , thereby increasing the risk of pavement failure. Aging manifests itself in the form of cracks, brittleness, loss of elasticity and loss of strength. Potholes and unwanted roughness appear, the edges of the road surface crumble. The road surface can deteriorate over time to the point of impeding driving and possibly reducing driving safety. Also in the field of building construction, the aging of bitumen leads to a loss of mechanical performance which results in leaks, water infiltration, surface discontinuities, such as cracks, cracks, broken tiles.
- bitumen is important to improve the performance of bitumen and extend the service life of pavements, buildings and substrates to which bitumen is applied as a waterproofing material such as roofs, terraces, balconies, facades, foundations, etc.
- Bisamide compounds have been described in applications EP2106423, WO2018/115730 and WO2020/120408 to improve the rheological properties of bitumen, in particular the characteristics of viscosity and hardness, during the production and implementation of bitumen. None of these documents mention or does not suggest a use of bisamide compounds to improve the aging resistance of bitumen.
- CA1260653 describes bituminous compositions for coating shingles comprising ethylene bis stearamide as an additive improving resistance to aging caused by weathering.
- CN106349723 describes the use of bisamide compounds in bituminous compositions to improve the softening temperature of bitumen while allowing the viscosity to be reduced when hot.
- the addition of the bisamide compound makes it possible to thin the bitumen more quickly at high temperature. This document does not describe the use of the bisamide compound to improve the aging resistance of bitumen.
- CN107286684 describes that the combination of a bisamide compound with inorganic nanomaterials improves the aging resistance of bituminous compositions.
- bitumen thus obtained having an improved resistance to aging, can be used, for example, in the manufacture of pavements and road maintenance products, in the construction of buildings as well as in the manufacture of waterproof roofing membranes, allowing to reduce the frequency of renewal and/or renovation of bituminous compositions in these different applications.
- the invention relates to the use of at least one bisamide compound of formula (I) RA-X-RC-X'-RB (I)
- - RA and RB being a linear, cyclic or branched, saturated or unsaturated hydrocarbon chain comprising 1 to 36 carbon atoms, and optionally comprising heteroatoms such as N, O, S,
- Rc being a linear, cyclic or branched, saturated or unsaturated hydrocarbon chain, comprising 3 to 18 carbon atoms, optionally substituted, and optionally comprising heteroatoms, such as N, O, S,
- - X and X' representing an amide function -NH-CO- or -CO-NH, to improve resistance to aging and/or increase the duration of use and/or delay the appearance of signs of aging of a composition bituminous.
- the bisamide compound corresponds to the formula (IA):
- Rc represents a hydrocarbon chain comprising from 3 to 18 carbon atoms.
- Rc represents a linear and saturated hydrocarbon chain.
- Rc is chosen from the groups —C4H8—, —CeHn—, —CsHie—, and —CIOH2O— .
- RA and RB which are identical or different, represent a linear hydrocarbon chain.
- the bisamide compound of general formula (I) is used at a content of 0.1 to 30% by mass relative to the total mass of the bituminous composition.
- the signs of aging are chosen from: cracks, detachments, ruts, subsidence, potholes, flaking, crumbling, blistering and/or cracking.
- the bisamide compounds of formula (I) are used to improve the resistance of the bituminous composition to oxidative and/or thermal ageing.
- the bisamide compounds of formula (I) are used to improve the resistance of the bituminous composition to aging caused by the presence of oxygen and/or by exposure to ultraviolet radiation and/or by a thermal variation and/or by a exposure to humidity and/or exposure to the weather.
- the bisamide compounds of formula (I) are used in the manufacture of pavements, to reduce the frequency of renewal and/or renovation of pavements.
- the bisamide compounds of formula (I) are used in the construction of buildings, to reduce the frequency of renewal and/or renovation of buildings.
- bituminous composition is a bituminous mix.
- the bisamide compounds of formula (I) are used to reduce and/or minimize and/or delay and/or attenuate the degradation of at least one mechanical property, preferably the ball and ring temperature and/or the elastic recovery, of the bituminous composition.
- the invention also relates to a method for improving the resistance to aging and/or increasing the service life and/or delaying the appearance of signs of aging of a bituminous composition, said method comprising at least the following steps: i. preparation of a bituminous composition comprising at least one bisamide compound of formula (I) as defined above and in more detail below, ii. aging of the bituminous composition, iii. measurement of aging resistance.
- the method comprises at least the following steps: i. preparation of a bituminous composition comprising at least one bisamide compound of formula (I), and optionally other additives, ii. subjecting the bituminous composition to an aging process caused by the presence of oxygen and/or by exposure to ultraviolet radiation and/or by thermal variations and/or by exposure to humidity and/or by exposure to severe weather, iii. measurement of one or more parameters selected from the ball and ring softening temperature, non-recoverable creep compliance, and/or the percentage of elastic recovery to evaluate the resistance to aging.
- the method of the invention further comprises a step of applying the bituminous composition to a roadway and/or to a surface of a building after step (i) of preparing the bituminous composition and before step (iii) of measuring the resistance to aging.
- the expression "between X and Y" includes the terminals, unless explicitly stated otherwise. This expression therefore means that the target interval includes the values X, Y and all values from X to Y.
- the object of the present invention is to provide an additive for bitumen making it possible to extend the service life of the bitumen.
- the present invention relates to the use of at least one bisamide compound of formula (I) as defined above and in detail below for improving the resistance to aging and/or increasing the duration of use and/or delay the appearance of signs of aging of a bituminous composition.
- the invention relates to a process for improving the resistance to aging and/or increasing the service life and/or delaying the appearance of signs of aging of a bituminous composition, the process comprising the preparation of a bituminous composition comprising at least one bisamide compound of formula (I) as defined above and in detail below, the aging of the bituminous composition then the measurement of the resistance to aging.
- bitumen bituminous composition
- bituminous binder are used, in an equivalent manner and independently of one another.
- bitumen means any bitumen-based compositions consisting of one or more bitumen bases and optionally comprising one or more chemical additives, said compositions being capable of being used in a road application, in particular in a mixture with aggregates, or in an application in the field of construction, in particular for the sealing of constructions.
- resistance to aging is meant the property of a bitumen of resisting the modification of its physico-chemical characteristics, in particular its rheological and mechanical characteristics, when it is subjected to an aging process, whatever the nature. 'origin.
- the invention makes it possible to improve the resistance of bitumen to aging resulting from chemical modifications caused by the presence of oxygen and/or by exposure to ultraviolet radiation and/or by thermal variations and/or by exposure to humidity and/or exposure to the weather.
- bituminous composition By “improving the resistance to aging of a bituminous composition”, is meant reducing and/or delaying and/or slowing down and/or avoiding and/or preventing and/or stopping and/or suppressing the aging of the bituminous composition.
- the ability of a bituminous composition to resist aging can be assessed by measuring one or more physico-chemical characteristics of the bituminous composition before aging, then repeating the same measurements after aging.
- the comparison of the physico-chemical properties of a bituminous composition before and after aging provides indicators of the resistance of the bituminous composition to ageing.
- bituminous composition By “increasing the duration of use of a bituminous composition” is meant first of all increasing the duration during which the bituminous composition can be kept in use after its application. This last property makes it possible to reduce the frequency of renewal and/or renovation of pavements, and/or to reduce the frequency of renovation of buildings.
- increasing the duration of use of a bituminous composition is also meant increasing the duration during which the composition can be stored and/or transported, while retaining good application properties. This latter property makes it possible to store and/or transport a bituminous composition over longer periods.
- bituminous compositions In the applications of the bituminous compositions, a better resistance to aging is observed by a later or less significant appearance of the signs of ageing.
- the signs of aging of a bituminous composition are in particular: the appearance of cracks and/or detachments and/or ruts and/or subsidence and/or potholes and/or flaking and/or crumbling and/or blistering and/or cracking. These signs can appear both on the pavements in the case where the bituminous composition is used in road applications and on the surface of buildings in the case where the bituminous composition is used to provide waterproofing, insulation, protection and waterproofing of surfaces such as roofs, terraces, balconies, facades, foundations, etc.
- the accelerated aging process using PAV equipment is used to simulate the long-term aging of bitumens in the laboratory.
- This protocol was developed in order to simulate the hardening of bitumen as it ages after several years of service in the field, for example 5 to 10 years.
- the test consists of treating the bituminous binders with pressurized air and high temperature to cause accelerated oxidation, simulating natural ageing.
- There procedure consists of placing 50 grams of a bituminous composition in a stainless steel cup. Several cups are then placed in an enclosure heated to 100° C. under a dry air pressure of 2.1 MPa, for a determined period.
- a detailed protocol of the accelerated aging process applied in the context of the present invention is described in the experimental part.
- the invention relates to an improvement in at least one physico-chemical characteristic of the bitumen which is observed after accelerated aging of the bituminous composition using PAV equipment over a period of at least 20 hours, preferably at least least 48 hours, more preferably at least 72 hours.
- the invention relates to an improvement in at least one physico-chemical characteristic of the bitumen which is observed after application and after aging of the bituminous composition under service conditions.
- the invention makes it possible to avoid and/or to delay the appearance and/or to reduce the importance of the signs of aging of the bitumen after application and after aging of the bituminous composition under service conditions.
- the physico-chemical characteristics measured to assess aging can be penetrability, ring and ball temperature (TBA), ductility, elastic response and sensitivity to permanent deformation, viscosity, chemical structure of bitumen, etc. This list of characteristics is not exhaustive, it is understood that other physico-chemical characteristics of the bitumen, known to those skilled in the art, can also be measured to assess the resistance to ageing.
- the variation in the physico-chemical characteristics of the bitumen before the aging test and after the aging test expresses the capacity of the bitumen to resist ageing, in particular oxidative ageing. More particularly, depending on each characteristic, the evaluation of the resistance to aging can be based on the rate of variation before the aging test and after the aging test as will appear clearly in the following.
- Vi represents the initial value of the characteristic measured before aging and Vf represents the final value of the characteristic measured after aging.
- Penetrability is a measurement called “needle penetrability" which is carried out using a standardized test NF EN 1426 at 25°C (P25). It represents the measurement of the penetration into a sample of bitumen or another type of binder, after a time of 5 seconds, of a needle whose weight with its support is 100g. The penetrability is expressed in tenths of a millimeter (dmm or 1/10 mm). In an aging process, penetrability tends to decrease over time.
- the ball and ring temperature is a measurement carried out by means of a standardized test NF EN 1427.
- the ball and ring softening temperature corresponds to the temperature at which a steel ball of standard diameter, after having passed through the material to be tested (stuck in a ring), reaches the bottom of a standardized vase filled with a liquid which is gradually heated, and in which the device has been immersed. In an aging process, the ball and ring temperature tends to increase over time.
- a bituminous composition is resistant to aging if the rate of variation of the ball and ring temperature is lower compared to that of the same bituminous composition not comprising compounds bisamide, it being understood that the rate of change of the ball and ring temperature is measured after an accelerated aging treatment of at least 20 hours using PAV equipment.
- the elastic response and sensitivity to permanent deformation of bitumen are parameters that can be evaluated by a creep-recovery test under repeated stresses (in English: Multiple Stress Creep Recovery MSCR).
- the MSCR test consists of a succession of creep-recovery tests at increasing stress levels carried out on a single sample at 60°C. 10 creep/recovery cycles are repeated at each stress threshold. During each cycle, the stress is applied for 1s and then the material recovers for 9s.
- the stress levels c0 applied in this order and without rest time are: 25, 50, 100, 200, 400, 800, 1600, 3200, 6400, 12800 and 25600 Pa.
- the objective of the MSCR test is to assess the resistance capacity of bitumen with respect to permanent deformation.
- This permanent deformation is defined by the non-recoverable compliance criteria Jnr and elastic recovery percentage sr. Both criteria are calculated from experimental data.
- - T corresponds to the stress applied during the creep-recovery cycle.
- the percentage of elastic recovery sr in % characterizes the percentage of deformation recovered with respect to the total deformation.
- a bituminous composition comprising a bisamide compound is resistant to aging if, for the same stress applied, the rate of variation of elastic recovery sr is lower compared to that of the same bituminous composition not comprising bisamide 1 compounds, it being understood that the rate of variation of the elastic recovery is measured after an accelerated aging treatment of at least 20 hours using P AV equipment.
- a bituminous composition comprising a bisamide compound is resistant to aging if, for the same stress applied, the rate of variation of non-recoverable creep compliance Jnr is lower. relative to the variation in non-recoverable compliance of the same bituminous composition not comprising bisamide compounds, it being understood that the rate of variation in non-recoverable compliance is measured after an accelerated aging treatment of at least 25 hours using PAV equipment.
- the use of the bisamide compounds of formula (I) as described above and in detail below makes it possible to reduce and/or minimize and/or delay and/or attenuate the degradation of at least one mechanical property, in particular the ball and ring temperature and/or the elastic recovery, of a bituminous composition.
- the term "mechanical property” preferably means the ball and ring temperature, the elastic recovery and/or the non-recoverable compliance.
- the bisamide compound(s) used in the context of the invention are chosen from the compounds of formula (I):
- the RA and RB groups which are identical or different, represent a linear, cyclic or branched, saturated or unsaturated hydrocarbon chain, comprising from 1 to 36 carbon atoms, and optionally comprising heteroatoms such as N, O, S,
- the Rc group represents a linear, cyclic or branched, saturated or unsaturated hydrocarbon chain, comprising from 1 to 22 carbon atoms, optionally substituted, and optionally comprising heteroatoms, such as N, O, S,
- - X and X' independently represent an amide function -NH-CO- or -CO-NH-.
- the compounds of formula (I) are chosen from the compounds of formula (IA) or the compounds of formula (IB) defined below:
- Rc represents a hydrocarbon chain comprising from 3 to 18 carbon atoms, preferably from 3 to 14 carbon atoms, preferably from 4 to 12 carbon atoms, preferably from 4 to 10 carbon atoms.
- Rc represents a linear and saturated hydrocarbon chain.
- Rc is chosen from the groups -C4H8-, -CeHn-, -CsHie-, and -C10H20-.
- RA and RB which are identical or different, represent a hydrocarbon chain comprising from 4 to 22 carbon atoms, preferably from 8 to 20 carbon atoms, more preferably from 10 to 20 carbon atoms.
- RA and RB groups include undecyl, dodecyl, tridecyl, tetradecyl, hexadecyl, heptadecyl, octadecyl, oleyl, eicosyl, etc.
- RA and RB identical or different, represent a linear hydrocarbon chain.
- RA and RB which are identical or different, represent a saturated hydrocarbon chain or a hydrocarbon chain comprising one or two alkenyl bonds. According to a further preferred embodiment, RA and RB, which are identical or different, represent a saturated hydrocarbon chain or a hydrocarbon chain comprising an alkenyl bond.
- RA and RB are identical.
- the sum of the carbon atoms making up RA, RB and Rc is between 12 and 60, even more preferably between 20 and 50.
- the bisamide compounds used in the context of the invention are chosen from the compounds of formula (IA).
- Particularly preferred bisamide compounds are, for example, compounds of formula (I), preferably compounds of formula (IA), in which:
- - Rc is a group -C4H8- and RA and RB each represent a heptadecyl group, preferably n-heptadecyl;
- - Rc is a -CeHn- group and RA and RB each represent an undecyl group, preferably n-undecyl, or alternatively,
- - Rc is a -CeHn- group and RA and RB each represent an n-heptadec-8-enyl group.
- the bisamide compound of general formula (I) can be prepared by conventional synthetic methods known to those skilled in the art, such as for example by reaction between a diamine and two carboxylic acids or by reaction between a dicarboxylic acid and two monoamines. Certain bisamide compounds corresponding to the general formula (I) are commercially available.
- the bisamide compound(s) of general formula (I), preferably of formula (IA) are used in the bituminous composition at a content ranging from 0.1 to 30% by mass, preferably from 0.5 to 20 %, preferably from 0.5 to 10%, more preferably from 1 to 5% by mass relative to the total mass of the bituminous composition.
- the bisamide compound as described above is responsible for the effect of improving the resistance to aging of the bitumen.
- the improvement in resistance to aging is observed when the bisamide compound is used alone and does not result from a synergistic effect between the bisamide compound according to the invention and another compound which can be included in the bituminous composition.
- bituminous compositions that can be used according to the invention can contain one or more bitumens from different origins.
- the bitumens which can be used according to the invention are advantageously chosen from bitumens originating from the refining of crude oil or originating from bituminous sands.
- the bitumens may be chosen from bitumens or mixtures of bitumens originating from the refining of crude oil, in particular bitumens containing asphaltenes or pitches.
- bitumens can be obtained by conventional processes for the manufacture of bitumens in refineries, in particular by direct distillation and/or vacuum distillation of petroleum. These bitumens can optionally be visbroken and/or deasphalted and/or air-rectified. It is common practice to carry out the vacuum distillation of the atmospheric residues resulting from the atmospheric distillation of crude oil. This manufacturing process therefore corresponds to the succession of an atmospheric distillation and a vacuum distillation, the charge supplying the vacuum distillation corresponding to the residues of the atmospheric distillation. These vacuum residues from the vacuum distillation tower can also be used as bitumen. It is also common to inject air into a charge usually composed of distillates and heavy products from the vacuum distillation of residues atmospheric emissions from petroleum distillation.
- This process makes it possible to obtain a blown, or semi-blown or oxidized or air-rectified or partially air-rectified base.
- the different bitumens or bitumen bases obtained by the refining processes can be combined with each other to obtain the best technical compromise.
- the bitumens can also be recycling bitumens.
- the bitumens can be hard grade or soft grade bitumens.
- bitumen is chosen from bitumens of natural origin; bitumen from oil sands; bitumens from the refining of crude oil such as atmospheric distillation residues, vacuum distillation residues, visbroken residues, blown residues and mixtures thereof; and their combinations or among synthetic bitumens otherwise called clear binders.
- the bitumen used in the invention has a needle penetrability measured at 25° C. according to standard EN 1426 of 5 to 330 1/10 mm, preferably of 20 to 220 1/10 mm.
- the bitumen used in the invention has a ring and ball softening temperature (TBA) according to standard EN 1427 of 50 to 175°C.
- TSA ring and ball softening temperature
- bituminous compositions can also comprise other additives different from the bisamide compounds according to the invention.
- additives may be chosen, in a non-limiting manner, from polymers, in particular elastomers, olefinic polymer adjuvants, vulcanizing agents and/or crosslinking agents, anti-caking agents and/or viscosifying agents.
- elastomer additives By way of example, among the elastomer additives, mention may be made of the SB, SB S, SIS, SB S*, SBR and EPDM copolymers. These elastomers can also be crosslinked according to any known method, for example with sulphur. Mention may also be made of elastomers made from styrene monomers and butadiene monomers allowing crosslinking without crosslinking agent as described in documents WO2007/058994, WO2008/137394 and by the applicant in patent application WO1 1/013073.
- olefinic polymer adjuvants mention may be made of ethylene/glycidyl (meth)acrylate copolymers, ethylene/monomer A/monomer B terpolymers, monomer A being chosen from vinyl acetate and alkyl acrylates or methacrylates in Cl to C6, the monomer B being chosen from acrylate glycidyl and glycidyl methacrylate, and mixtures of these copolymers.
- Olefinic polymer adjuvants are described in detail in applications WO2020/187580 and WO2021/019141.
- anti-caking compounds include: talc; fines generally with a diameter of less than 125 ⁇ m; sand ; cement ; carbon; wood residues such as lignin, conifer needle powders and conifer cone powders; glass powder; alumina; silica; silica derivatives such as silicates, fumed silica; silicon hydroxides and silicon oxides; plastic powder; and their mixtures.
- Anti-caking compounds are described in detail in application WO2018/046840.
- the bituminous composition according to the invention comprises from 0.05% to 15% by weight of one or more of the additives such as those mentioned in detail above, more preferably from 0.1% to 10% by weight , even more preferably from 0.5% to 6% by weight, relative to the total weight of the bituminous composition.
- bituminous composition used according to the invention can be in any form.
- bituminous composition according to the invention is solid when cold and in a divided form.
- cold solid composition a bitumen having a solid appearance at room temperature regardless of the transport and/or storage conditions, in particular a bitumen which retains its solid appearance and which does not flow at room temperature under its own weight or when subjected to pressure forces resulting from transport and/or storage conditions.
- a divided form is meant a composition in the form of units distinct from each other, such as granules or bars.
- the divided form can be obtained by shaping the bituminous composition according to any known method, for example according to the manufacturing method described in documents US 3,026,568, WO 2009/153324 or WO 2012/168380. In particular, the methods described in WO2018/104660 can be used.
- bituminous composition used according to the invention essentially consists of one or more bitumens and one or more compounds of formula (I) as defined above.
- bituminous compositions comprise, preferably essentially consist of: - 70% to 99.9% by mass of bitumen and
- bituminous compositions comprise, preferably consist essentially of:
- bitumen - 80% to 99.5% by mass of bitumen
- bituminous compositions preferably comprise, preferably essentially consist of:
- the invention relates to the supply of a bituminous coating having improved resistance to aging, comprising aggregates and at least one bituminous composition as described above and comprising at least one bisamide compound of formula (I) , preferably a bisamide compound of formula (IA).
- aggregates is meant a set of mineral grains having a size of less than 125 mm such as fines, sand, sand, gravel, gravel, ballast, rockfill and a mixture of these materials.
- the subject of the present invention is a method for improving the resistance to aging and/or increasing the duration of use and/or delaying the appearance of signs of aging of a bituminous composition, said method comprising at least the following steps: i. preparation of a bituminous composition comprising at least one bisamide compound of formula (I), and optionally other additives, ii. aging of the bituminous composition, iii. measurement of aging resistance.
- the method comprises at least the following steps: i. preparation of a bituminous composition comprising at least one bisamide compound of formula (I), and optionally other additives, ii. subjecting the bituminous composition to an aging process caused by the presence of oxygen and/or by exposure to ultraviolet radiation and/or by thermal variations and/or by exposure to humidity and/or by exposure to bad weather, iii. measurement of one or more parameters selected from the ball and ring softening temperature, non-recoverable creep compliance, and/or the percentage of elastic recovery to evaluate the resistance to aging.
- the first step (i) of the process is a step for preparing a bituminous composition comprising one or more bisamide compounds as defined above.
- This step can be carried out according to conventional techniques known to those skilled in the art.
- this step may comprise (a) the implementation of at least one bitumen by heating it to a temperature between 110 and 180° C., (b) the addition of at least one bisamide compound of formula (I ) with bitumen and optionally other additives, and (c) stirring the bituminous composition until the mixture is homogenized.
- the method for preparing the bituminous compositions according to the invention comprises the following steps: a) bitumen is introduced into a container equipped with mixing means, and the bitumen is brought to a temperature between 70 and 220°C, preferably between 90 and 180°C, preferably between 110 and 180°C, b) introducing at least one bisamide compound of formula (I) and optionally additives, c) heating the bituminous composition resulting of step b) at a temperature of between 70 and 220°C, preferably between 90 and 180°C, preferably between 110 and 180°C, with stirring, until a homogeneous bituminous composition is obtained , d) optionally, the bituminous composition resulting from step c), and in particular in divided form, is shaped.
- the person skilled in the art is able to adapt the mixing parameters such as the heating temperature, the mixing time, the stirring speed, etc.
- the method for improving the resistance to aging and/or increasing the service life and/or delaying the appearance of signs of aging of a bituminous composition comprises a step (i' ) application of the bituminous composition after the step of preparing the bituminous composition according to the invention (i) and before the aging step (ii).
- bituminous composition By “application of the bituminous composition”, is meant the implementation by the so-called “hot”, “warm” techniques or the so-called “cold” techniques, well known by those skilled in the art of the bituminous composition , to manufacture coatings such as in the field of road construction, the building industry or to ensure the sealing of supports such as roofs.
- the aging step (ii) of the bituminous composition may comprise short-term aging and/or long-term aging.
- the aging step (ii) of the bituminous composition is a short-term aging step.
- the aging step (ii) of the bituminous composition comprises a short-term aging sub-step followed by a long-term aging sub-step.
- This stage (ii) can be aging carried out on a laboratory scale, in particular by the accelerated aging protocols described in detail above, or aging during service, that is to say after the application of the bitumen. , in particular on a roadway or on a building.
- the step of measuring the resistance to aging (iii) is preferably carried out by measuring the rate of variation of the value of one or more characteristic parameters of the bitumens after aging process, accelerated or not, with respect to the value of said parameter before ageing.
- the parameter(s) measured are preferably chosen from the ball and ring softening temperature, non-recoverable creep compliance, and/or the percentage of elastic recovery.
- the methods for measuring each parameter are those known to those skilled in the art and in particular the methods as defined above in the present invention.
- the invention relates to a method for improving the resistance to aging and/or increasing the service life and/or delaying the appearance of signs of aging of a bituminous mix comprising at least the following steps:
- - heating aggregates to a temperature ranging from 100° C. to 180° C., preferably from 120° C. to 160° C.,
- Figure 1 shows the variation curves of the elastic recovery sr (in %, ordinate axis) as a function of the applied stress (in kPa, abscissa axis) of different bituminous compositions before aging (solid curves) and after aging following an accelerated aging protocol using a PAV for 25 h (curves in broken line) and for 48 h (curves in dotted line).
- Bitumen grade 35/50 bitumen base having a P25 penetrability of 46 1/10 mm and a TBA of 53.2°C and commercially available from the company TotalEnergies under the brand AZALT®.
- Additive 5 (comparative): N,N'-ethylenedi(stearamide) commercially available under the trademark Crodawax®.
- bituminous compositions with additives are prepared by introducing into a reactor with stirring and at 170° C. the bitumen base and the additive in the proportions reported in Table 2 below. The mixtures are stirred and heated to 160°C for about 1 hour.
- Compositions C1 to C3 are according to the invention and compositions C4 and C5 are comparative.
- Composition CO is a control composition which does not include any additive. The proportions of the additives in the different compositions are chosen so as to obtain bituminous compositions having the same TB A value around 100°C.
- FIG. 1 represents the variation curves of the elastic recovery (in %) of the compositions C0 to C5 before and after aging as a function of different stresses. These curves show that the bituminous compositions added with the bisamide compounds according to the invention better recover their resistance compared to the non-additive bitumen (C0), after accelerated aging protocol using a PAV equipment at 25h and 48h. The bituminous compositions with additives with the bisamide compounds of formula (I) show very few signs of aging.
- Table 4 Properties of bituminous compositions following an accelerated aging protocol using PAV equipment at 25h:
- Table 5 Properties of bituminous compositions following an accelerated aging protocol using PAV equipment at 48 hours:
- compositions C1 to C3 are markedly lower than the corresponding variation rates in the case of a composition comprising the Irganox additive (composition C4) or a bitumen composition without additives.
- compositions C1 to C3 comprising the bisamide additives of formula (I) according to the invention exhibit lower rates of variation in the recovery under stress conditions at 0.1 kPa and at 3.2 kPa after 25 and 48 h compared to composition C5 comprising a bisamide additive as described in the prior art US2019/184678.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Organic Chemistry (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Engineering & Computer Science (AREA)
- Civil Engineering (AREA)
- Structural Engineering (AREA)
- Materials Engineering (AREA)
- General Chemical & Material Sciences (AREA)
- Oil, Petroleum & Natural Gas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
Applications Claiming Priority (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| FR2113817A FR3130806A1 (fr) | 2021-12-17 | 2021-12-17 | Utilisation de composés bisamide pour améliorer la résistance au vieillissement du bitume |
| PCT/EP2022/085422 WO2023110761A1 (fr) | 2021-12-17 | 2022-12-12 | Utilisation de composes bisamide pour ameliorer la resistance au vieillissement du bitume |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| EP4448632A1 true EP4448632A1 (de) | 2024-10-23 |
Family
ID=82019584
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| EP22835702.6A Pending EP4448632A1 (de) | 2021-12-17 | 2022-12-12 | Verwendung von bisamidverbindungen zur verbesserung der alterungsbeständigkeit von bitumen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US20250059374A1 (de) |
| EP (1) | EP4448632A1 (de) |
| CA (1) | CA3241174A1 (de) |
| FR (1) | FR3130806A1 (de) |
| WO (1) | WO2023110761A1 (de) |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| FR3157872A1 (fr) * | 2023-12-29 | 2025-07-04 | Totalenergies Onetech | Additifs pour enrobés bitumineux |
| FR3164215A1 (fr) * | 2024-12-02 | 2026-01-09 | Totalenergies Onetech | Liants bitumineux à empreinte carbone réduite pour produire des enrobés tièdes |
Family Cites Families (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3026568A (en) | 1958-11-14 | 1962-03-27 | Schuller Services Ltd | Method for producing coated bitumen pellets |
| CA1260653A (en) * | 1985-04-11 | 1989-09-26 | Richard T. Janicki | Modified asphalt |
| US6542832B1 (en) | 1999-08-18 | 2003-04-01 | Fisher Controls International, Inc. | Error detection and correction system for use with dual-pulse output metering devices |
| EP2589624B1 (de) | 2005-11-14 | 2015-04-01 | Kraton Polymers US LLC | Polymerzusammensetzung zur Herstellung einer bituminösen Binderzusammensetzung |
| FR2911611B1 (fr) | 2007-01-23 | 2011-01-07 | Total France | Composition bitumineuse aux proprietes thermoreversibles. |
| US7622519B2 (en) | 2007-05-01 | 2009-11-24 | Kraton Polymers U.S. Llc | Bituminous binder composition and process for preparing the same |
| CN102066068B (zh) | 2008-06-20 | 2017-06-20 | 国际壳牌研究有限公司 | 涂覆粘合剂单元的制备方法 |
| FR2948677B1 (fr) | 2009-07-29 | 2011-09-16 | Total Raffinage Marketing | Procede de preparation de compositions bitume/polymere reticulees sans agent reticulant |
| CN103597035B (zh) | 2011-06-07 | 2016-03-16 | 国际壳牌研究有限公司 | 制备包覆粘合剂单元的方法 |
| WO2017027096A2 (en) | 2015-06-10 | 2017-02-16 | A.L.M Holding Company | Use of sterols as an additive in asphalt binder |
| CN106349723B (zh) * | 2016-08-30 | 2020-04-14 | 北京东方雨虹防水技术股份有限公司 | 一种改性沥青胶料及其制备方法、沥青防水卷材 |
| FR3055633B1 (fr) | 2016-09-08 | 2020-06-12 | Total Marketing Services | Granules de brai solides a temperature ambiante |
| FR3059674B1 (fr) | 2016-12-07 | 2018-11-23 | Total Marketing Services | Bitume solide a temperature ambiante |
| FR3061191B1 (fr) | 2016-12-22 | 2019-05-24 | Total Marketing Services | Composition d’asphalte coule pour la realisation de revetements |
| CN107286684A (zh) * | 2017-06-30 | 2017-10-24 | 中油佳汇防水科技（深圳）股份有限公司 | 一种聚合物改性沥青胶料及其制备方法、防水卷材 |
| MX2020006278A (es) * | 2017-12-15 | 2020-09-14 | Owens Corning Intellectual Capital Llc | Material para techo de asfalto modificado con polimero. |
| FR3090000B1 (fr) | 2018-12-12 | 2020-12-18 | Total Marketing Services | Granules de bitume solides à température ambiante |
| WO2020187580A1 (en) | 2019-03-18 | 2020-09-24 | Total Marketing Services | Bituminous composition solid at ambient temperature |
| FR3099486B1 (fr) | 2019-07-31 | 2023-04-28 | Total Marketing Services | Composition bitume/polymère fluxée et son procédé de préparation |
-
2021
- 2021-12-17 FR FR2113817A patent/FR3130806A1/fr active Pending
-
2022
- 2022-12-12 CA CA3241174A patent/CA3241174A1/fr active Pending
- 2022-12-12 EP EP22835702.6A patent/EP4448632A1/de active Pending
- 2022-12-12 US US18/720,548 patent/US20250059374A1/en active Pending
- 2022-12-12 WO PCT/EP2022/085422 patent/WO2023110761A1/fr not_active Ceased
Also Published As
| Publication number | Publication date |
|---|---|
| WO2023110761A1 (fr) | 2023-06-22 |
| FR3130806A1 (fr) | 2023-06-23 |
| CA3241174A1 (fr) | 2023-06-22 |
| US20250059374A1 (en) | 2025-02-20 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| EP2576911B1 (de) | Verfahren zur herstellung von kalten bituminösen gemischen, kalte bituminöse gemische mit kontrollierter bearbeitbarkeit und ihre verwendung zur herstellung von strassenpflasterungen | |
| EP0603028B1 (de) | Bitumen-Polymer Zusammensetzungen, Verfahren zu deren Herstellung und Verwendung | |
| EP4448632A1 (de) | Verwendung von bisamidverbindungen zur verbesserung der alterungsbeständigkeit von bitumen | |
| FR2997945A1 (fr) | Liant modifie au glycerol pour la production d'enrobes hydrocarbones a taux eleve en materiaux bitumineux recycles | |
| WO2010055491A1 (fr) | Liant synthetique clair | |
| FR3107277A1 (fr) | Utilisation d’un additif pour retarder le vieillissement du bitume | |
| WO2011051912A1 (fr) | Utilisation de cires dans une composition bitume/polymere reticulee pour ameliorer sa resistance aux agressions chimiques et composition bitume/polymere reticulee comprenant lesdites cires | |
| FR2949232A1 (fr) | Composition bitumineuse contenant un polymer supramoleculaire | |
| EP2178925A2 (de) | Pfropfpolymer und wärmeumkehrbare vernetzte bitumenzusammensetzung mit besagtem pfropfpolymer | |
| WO2014199063A1 (fr) | Additifs pour bitume industriel | |
| EP2121847A1 (de) | Alterungsresistente bitumenzusammensetzung | |
| WO2004060991A2 (fr) | Procede de preparation de compositions bitume/polymere a resistance aux solvants petroliers amelioree, compositions ainsi obtenues et leur utilisation comme liant bitumineux | |
| EP3283571B1 (de) | Durchsichtige bindemittel und deren anwendungen | |
| EP2935442A1 (de) | Bitumenbindezusammensetzung zur herstellung von beschichtungsmaterialien bei tiefen temperaturen | |
| EP3891223B1 (de) | Bituminöser mastix, verfahren zur herstellung davon und verwendungen davon | |
| FR3054568A1 (fr) | Agents fluxants pour liants hydrocarbones | |
| EP3491069B1 (de) | Flussmittel für bituminöse bindemittel | |
| WO2021019141A1 (fr) | Composition bitume/polymere fluxee et son procede de preparation | |
| EP4077494B1 (de) | Pechzusammensetzungen , zugehörige verfahren und verwendungen | |
| FR3097551A1 (fr) | Compositions bitumineuses thermoréticulées comprenant des particules d’argile, procédés et utilisations associés | |
| EP3440130A1 (de) | Verfahren zur herstellung einer bitumen-/polymerzusammensetzung mit verbesserten eigenschaften | |
| WO2026017950A1 (fr) | Additif pour matériaux routiers | |
| FR3155233A1 (fr) | Composition bitumineuse comprenant un residu de conversion thermique de plastique | |
| EP3556827A1 (de) | Herstellungsverfahren einer zusammensetzung aus netzförmigem bitumenpolymer mit geringer h2s-abscheidung, und einsatz dieser zusammensetzung zur herstellung von verkleidungen | |
| FR3065730A1 (fr) | Agents fluxants pour liants hydrocarbones |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: UNKNOWN |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: THE INTERNATIONAL PUBLICATION HAS BEEN MADE |
|
| PUAI | Public reference made under article 153(3) epc to a published international application that has entered the european phase |
Free format text: ORIGINAL CODE: 0009012 |
|
| STAA | Information on the status of an ep patent application or granted ep patent |
Free format text: STATUS: REQUEST FOR EXAMINATION WAS MADE |
|
| 17P | Request for examination filed |
Effective date: 20240717 |
|
| AK | Designated contracting states |
Kind code of ref document: A1 Designated state(s): AL AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HR HU IE IS IT LI LT LU LV MC ME MK MT NL NO PL PT RO RS SE SI SK SM TR |
|
| DAV | Request for validation of the european patent (deleted) | ||
| DAX | Request for extension of the european patent (deleted) |