BITUMINOUS COMPOSITION WITH THERMOREVERSIBLE PROPERTIES

• US 20100192804A1
• Filed: 01/18/2008
• Published: 08/05/2010
• Est. Priority Date: 01/23/2007
• Status: Abandoned Application

• Current Assignee: Total Raffinage Marketing (Cook Composites and Polymers), University Pierre et Marie Curie
• Original Assignee: Total Raffinage Marketing (Cook Composites and Polymers)
• Inventors: Isare, Benjamin, Vincent, Régis, Bouteille, Laurent, Lapalu, Laurence
• Application Number:
  US12/523,838
• Publication Number:
  US 20100192804A1
• Time in Patent Office: Days
• US Class Current: 106/277
• CPC Class Codes: C08K 5/0008 Organic ingredients according to more than one of the "one dot" groups of C08K5/01 - C08K5/59
• CPC Class Codes: C08K 5/092 Polycarboxylic acids
• CPC Class Codes: C08L 2666/66 Substances characterised by their function in the composition
• CPC Class Codes: C08L 95/00 Compositions of bituminous materials, e.g. asphalt, tar, pitch
• CPC Class Codes: C09D 195/00 Coating compositions based on bituminous materials, e.g. asphalt, tar, pitch

Abstract

The invention relates to a bituminous composition that comprises a major portion of at least one bitumen and a minor portion of at least one chemical additive, said additive being an organogelling agent that generates a network of hydrogen bonds between the organogelling molecules constituting the same, and trapping the bitumen phase up to a maximum temperature T_R of between 40 and 120° C. The invention also relates to the use of these bitumen compositions in the field of road applications, particularly in the production of road binders, as well as in industrial applications. The invention also relates to a method for preparing these bituminous compositions.

Claims

1. A bituminous composition comprising a major proportion of at least one bitumen and a minor proportion of at least one chemical additive, the additive being an organogelator creating a network of hydrogen bonds between organogelling molecules which have a molar mass of less than or equal to 2000 gmol⁻

1, said organogelator comprising at least one hydrogen bond donor D, at least one hydrogen bond acceptor A and at least one compatibilizer C in the bitumen, said compatibilizer C comprising a group chosen from;

at least one linear hydrocarbon chain comprising at least 4 carbon atoms, or

at least one aliphatic ring of 3 to 8 atoms, or

at least one condensed polycyclic system which is aliphatic, or partly aromatic or also wholly aromatic, each ring comprising 5 or 6 atoms, alone or in a mixture.

2. The composition according to claim 1, wherein the donor D comprises a heteroatom bearing a hydrogen chosen from nitrogen N, oxygen O and/or sulphur S.

3. The composition according to claim 1, wherein the donor D is chosen from the alcohol, thiol, phenol, primary amine, secondary amine, quaternary ammonium, amide, urea, hydrazine, carboxylic acid, oxime, hydrazone, imine groups and combinations thereof.

4. The composition according to claim 1, wherein the acceptor A comprises a heteroatom bearing electronic doublets chosen from oxygen O, sulphur S, nitrogen N and/or phosphorus P.

5. The composition according to claim 1, wherein the acceptor A is chosen from the C═

O, S═

O, N═

O or P═

O groups and the linear or cyclic hydrocarbon groups containing in their hydrocarbon chain a heteroatom of oxygen O, sulphur S, nitrogen N or phosphorus P.

6. The composition according to claim 1, wherein the acceptor A is chosen from the alcohol, phenol, amide, ester, urea, hydrazine, acid, ketone, aldehyde, lactone, lactame, anhydride, imide, sulphoxide, sulphone, sulphonate, sulphate, sulphite, sulphonic acid, sulphide, ether, phosphine, phosphite, phosphonate, phosphate, nitrite or nitrate groups and combinations thereof.

7. The composition according to claim 1, wherein the organogelator comprises organogelling molecules of identical chemical structure.

8. The composition according to claim 1, wherein the organogelator comprises at least one unit of general formula (I):

R—

(NH)_nCONH—

(X)_m—

NHCO(NH)_n—

R′

,

the R and R′

groups, identical or different, contain a linear, branched or cyclic, saturated or unsaturated hydrocarbon chain, comprising 1 to 22 carbon atoms, optionally substituted, and optionally comprising heteroatoms, rings and/or heterocycles;

the X group contains a linear, cyclic or branched, saturated or unsaturated hydrocarbon chain, comprising 1 to 22 carbon atoms, optionally substituted, and optionally comprising heteroatoms, rings and/or heterocycles;

n and m are integers having a value of 0 or 1 independently of each other.

9. The composition according to claim 8, wherein the organogelator comprises a hydrazide unit when n and m have a value of 0.

10. The composition according to claim 8, wherein the organogelator comprises two amide units when n has a value of 0 and m has a value of 1.

11. The composition according to claim 8, wherein the organogelator comprises two urea units when n and m have a value of 1.

12. The composition according to claim 8, wherein the R and/or R′

group comprises an aliphatic hydrocarbon chain of 4 to 22 carbon atoms, in particular chosen from the C₄H₉, C₅H₁₁, C₉H₁₉, C₁₁H₂₃, C₁₂H₂₅, C₁₇H₃₅, C₁₈H₃₇, C₂₁H₄₃, C₂₂H₄₅ groups.

13. The composition according to claim 8, wherein the X group comprises an aliphatic hydrocarbon chain of 1 to 2 carbon atoms.

14. The composition according to claim 8, wherein the X group comprises two rings of 6 carbon atoms linked by a CH₂ group, these rings being aliphatic or aromatic.

15. The composition according to claim 1, wherein the organogelator comprises at least one unit of general formula (II):

(R—

NHCO)_x—

Z—

(NHCO—

R′

)_y

R and R′

, identical or different, contain a linear, branched or cyclic, saturated or unsaturated hydrocarbon chain comprising 1 to 22 carbon atoms, optionally substituted, and optionally comprising heteroatoms, rings and/or heterocycles,

Z represents a tri-functionalized group chosen from the following groups;

x and y are different integers with a value varying from 0 to 3 and such that x+y=3.

16. The composition according to claim 1, wherein the organogelator comprises at least one sorbitol derivative (III).

17. The composition according to claim 16, wherein the sorbitol derivative is a product of the reaction between an aldehyde and D-sorbitol.

18. The composition according to claim 17, wherein the organogelator is 1,3:

2,4-Di-O-benzylidene-D-sorbitol.

19. The composition according to claim 1, wherein the organogelator comprises at least one unit of general formula (IV):

R″

—

(COOH)_z

with R″

a linear or branched, saturated or unsaturated chain comprising 4 to 68 carbon atoms, preferably 4 to 54 carbon atoms, more preferentially 4 to 36 carbon atoms and z an integer varying from 2 to 4.

20. The composition according to claim 19, wherein the organogelator is a diacid of general formula HOOC—

C_wH_2w—

COOH with w an integer varying from 4 to 22, preferably 4 to 12 where z=2 and R″

=C_wH_2w.

21. The composition according to claim 20, wherein the organogelator is a diacid chosen from the following diacids:

adipic acid, pimelic acid, suberic acid, azelaic acid, sebacic acid, undecanedioic acid, 1,2-dodecanedioic acid or tetradecanedioic acid.

22. The composition according to claim 1, wherein the organogelator comprises at least one unit of general formula (V):

the Y and Y′

groups represent independently of each other, an atom or group chosen from;

H, —

(CH₂)q-CH₃, —

(CH₂)q-NH₂, —

(CH₂)q-OH, —

(CH₂)q-COOH or

with q an integer varying from 2 to 18, preferably 2 to 10, preferably 2 to 4 and p an integer greater than or equal to 2, preferably having a value of 2 or 3.

23. The composition according to claim 22, wherein the organogelator has the formula:

24. The composition according to claim 1, wherein the organogelator comprises at least one unit of general formula (VI):

R—

NH—

CO—

CO—

NH—

R′

with R and R′

, identical or different, which represent a linear, branched or cyclic, saturated or unsaturated hydrocarbon chain, comprising 1 to 22 carbon atoms, optionally substituted, and optionally comprising heteroatoms, rings and/or heterocycles.

25. The composition according to claim 1, wherein the organogelator (VII) comprises at least 2 organogelling molecules of different chemical structure, all of the three units A, D and C being found in the organogelator.

26. The composition according to claim 25, wherein the organogelator comprises an amine derivative and a carboxylic acid derivative.

27. The composition according to claim 25, wherein the organogelator comprises an aminopyrimidine derivative and a barbituric acid derivative.

28. The composition according to claim 25, wherein the organogelator comprises a sulphosuccinate derivative and a phenol derivative.

29. The composition according to claim 1, wherein the organogelling molecules have a molar mass of less than or equal to 1000 gmol⁻

1.

30. The composition according to claim 1, wherein the organogelator is present at 0.1 to 5% by mass with respect to the bitumen.

31. The composition according to claim 1, wherein the bitumen also comprises at least one polymer and/or one flux.

32. The composition according to claim 1, wherein the bitumen is chosen from the atmospheric distillation residues, the vacuum distillation residues, visbroken residues, blown residues, their mixtures and combinations thereof.

33. A use of a bituminous composition according to claim 1, further comprising manufacturing a bituminous binder, in particular an anhydrous binder, a bituminous emulsion, a polymer bitumen or a fluxed bitumen.

34. The use of a bituminous composition according to claim 33 in a mixture with aggregates for manufacturing a surface dressing, a hot mix, a cold mix, a cold-cast mix, a gravel emulsion or a wearing course.

35. The use of a bituminous composition according to claim 33 for manufacturing a sealing membrane, a membrane or an impregnation layer.

36. A method for obtaining a bituminous composition according to claim 1, wherein the organogelator is introduced when hot at temperatures varying from 140 to 180°

C., either into the bitumen alone, into the bitumen modified or not modified by polymers, into the bitumen in the form of bituminous binder or into the bitumen when the latter is in the form of anhydrous binder, bituminous mix, or surface dressing, or during the manufacture of said bitumens, binders or dressings.

37. The method according to claim 36 for obtaining a bituminous composition which is hard at the temperatures of use without increasing its viscosity when hot.