IP Library Granted Patent US 11,879,062
Granted Patent B2
US 11,879,062 · App. 17/296,412 · Granted Jan 23, 2024

Bituminous composition solid at ambient temperature

Inventor: Régis Vincent (Grigny, FR)
Assignee: TOTAL MARKETING SERVICES
C08L95/00C04B26/26C08K5/20C08K5/25C04B2111/0075C08L2555/22C08L2555/34C08L2555/60
View Patent ↗
Loading inventors, assignments & file history…
Monitor This Case
Get email alerts when status or documents change.
Order Certified Copies
Most orders are placed with the USPTO same day — all within 24 business hours.
Order via The Patent Place →
Pre-filled with this patent's details
Quick Facts
Patent No.
US 11,879,062
App. No.
17/296,412
Granted
Jan 23, 2024
Kind
B2
Abstract

A bituminous composition and a process for the preparation of bituminous mixes including at least one bitumen base, at least one compound of general formula Ar1-R 1 —Ar 2 (I), and at least one compound of general formula R 2 —(NH) n CONH—X—(NHCO) p (NH) n —R′ 2 (II). The composition is used as road binder, notably for the preparation of bituminous mixes.

Claims (57)

1. A bituminous composition which is solid at ambient temperature and in a divided form, said bituminous composition comprising at least:

a) a bitumen base,

b) a compound of general formula (I):

Ar1-R 1 —Ar 2   (I)

wherein:

Ar1 and Ar2 represent, independently of each other, an aromatic group comprising from 6 to 20 carbon atoms chosen among a benzene nucleus or a system of condensed aromatic nuclei, said aromatic group being substituted by at least one hydroxyl group and optionally by one or more C 1 -C 20 alkyl groups, and

R 1 represents an optionally substituted hydrocarbon divalent radical, the main chain of which comprises from 6 to 20 carbon atoms and at least one group chosen from the amide, ester, hydrazide, urea, carbamate and anhydride functional groups, and

c) a compound of general formula (II):

R 2 —(NH) n CONH—X—(NHCO) p (NH) n —R′ 2   (II)

wherein:

the R 2 and R′ 2 groups, which are identical or different, represent a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms, and R 2 can be H,

the X group represents a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms and

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

2. The bituminous composition according to claim 1 , which is in the form of blocks or pellets.

3. The bituminous composition as claimed in claim 1 , wherein the compound of general formula (I) is 2′,3-bis[(3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propionyl)]propionohydrazide.

4. The bituminous composition as claimed in claim 1 , wherein the compound of general formula (II) is chosen from compounds of general formula (IIA):

R 2 —CONH—X—NHCO—R′ 2   (IIA)

wherein R 2 and R′ 2 , which are identical or different, represent a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms, such as N, O or S, and R 2 can be H, and

X represents a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms, such as N, O or S.

5. The bituminous composition as claimed in claim 4 , wherein the compound of general formula (IIA) is chosen from the compounds C 5 H 11 —CONH—NHCO—C 5 H 11 , C 9 H 19 —CONH—NHCO—C 9 H 19 , C 11 H 23 —CONH—NHCO—C 11 H 23 , C 17 H 35 —CONH—NHCO—C 17 H 35 or C 21 H 43 —CONH—NHCO—C 21 H 43 ; N,N′-ethylenedi(laurylamide) of formula C 11 H 23 —CONH—CH 2 —CH 2 —NHCO—C 11 H 23 , N,N′-ethylenedi(myristylamide) of formula C 13 H 27 —CONH—CH 2 —CH 2 —NHCO—C 13 H 27 , N,N′-ethylenedi(palmitamide) of formula C 15 H 31 —CONH—CH 2 —CH 2 —NHCO—C 15 H 31 or N,N′-ethylenedi(stearamide) of formula C 17 H 35 —CONH—CH 2 —CH 2 —NHCO—C 17 H 35 ; laurylamide of formula C 11 H 23 —CONH 2 , myristylamide of formula C 13 H 27 —CONH 2 , palmitamide of formula C 15 H 31 —CONH 2 or stearamide of formula C 17 H 35 —CONH 2 .

6. The bituminous composition as claimed in claim 5 , wherein the compound of general formula (IIA) is N,N′-ethylenedi(stearamide) of formula C 17 H 35 —CONH—CH 2 —CH 2 —NHCO—C 17 H 35 .

7. The bituminous composition as claimed in claim 1 , wherein the bituminous composition comprises from 0.1 to 10% by weight of one or more compounds of general formula (I), with respect to the total weight of the bituminous composition.

8. The bituminous composition as claimed in claim 1 , wherein the bituminous composition comprises from 0.1% to 10% by weight of one or more compounds of general formula (II), with respect to the total weight of the bituminous composition.

9. The bituminous composition as claimed in claim 1 , wherein it comprises from 80 to 99.8% by weight of one or more bitumen bases.

10. The bituminous composition as claimed in claim 1 , wherein it comprises from 0.05 to 15% of one or more olefinic polymer adjuvants.

11. The bituminous composition as claimed in claim 1 , wherein it comprises:

a) from 80 to 99.8% by weight of one or more bitumen bases,

b) from 0.1 to 10% by weight of one or more additives of general formula (I),

c) from 0.1 to 10% by weight of one or more additives of general formula (II), and

d) optionally, from 0.05 to 15% by weight of one or more olefinic polymer adjuvants,

with respect to the total weight of the bituminous composition.

12. The bituminous composition as claimed in claim 1 , wherein the bitumen base has a penetrability at 25° C., measured according to standard EN 1427, less than or equal to 200 1/10 mm.

13. The bituminous composition as claimed in claim 1 , wherein the bituminous composition has a ring-and-ball softening temperature, measured according to standard EN 1427, of from 80 to 120° C.

14. The bituminous composition as claimed in claim 1 , wherein the bituminous composition has a deformability at 65° C., less than or equal to 50%.

15. The bituminous composition as claimed in claim 1 , comprising 0.65 to 1 weight % of 2′,3-bis[(3-[3,5-di(tert-butyl)-4-hydroxyphenyl]propionyl)]propionohydrazide as the compound of general formula (I) and 1 to 3 weight % of N,N′-ethylenedi(stearamide) as the compound of general formula (II).

16. A bituminous mix comprising:

(i) a bituminous composition, and

(ii) aggregates, and/or inorganic fillers and/or synthetic fillers, wherein the bituminous composition comprises at least:

a) a bitumen base,

b) a compound of general formula (I):

Ar1-R 1 —Ar 2   (I)

wherein:

Ar1 and Ar2 represent, independently of each other, an aromatic group comprising from 6 to 20 carbon atoms chosen among a benzene nucleus or a system of condensed aromatic nuclei, said aromatic group being substituted by at least one hydroxyl group and optionally by one or more C 1 -C 20 alkyl groups, and

R 1 represents an optionally substituted hydrocarbon divalent radical, the main chain of which comprises from 6 to 20 carbon atoms and at least one group chosen from the amide, ester, hydrazide, urea, carbamate and anhydride functional groups,

c) a compound of general formula (II):

R 2 —(NH) n CONH—X—(NHCO) p (NH) n —R′ 2   (II)

wherein:

the R 2 and R′ 2 groups, which are identical or different, represent a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms, and R 2 can be H,

the X group represents a hydrocarbon chain comprising from 1 to 22 carbon atoms which is optionally substituted and which optionally comprises one or more heteroatoms, and

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

17. The bituminous mix as claimed in claim 16 , which is a road bituminous mix, a bituminous concrete or a bituminous mastic.

18. A process for the manufacture of bituminous mixes as claimed in claim 16 , said process comprising at least the following steps:

1) heating the aggregates at a temperature ranging from 100° C. to 180° C.,

2) mixing the aggregates with the road binder in a vessel,

3) obtaining bituminous mixes.

19. The process as claimed in claim 18 , wherein at least part of the aggregates originates from recycled bituminous mixes.

20. The process as claimed in claim 18 , which does not comprise a stage of heating the road binder before it is mixed with aggregates.

Assignments (3)
CORRECTIVE ASSIGNMENT TO CORRECT THE THE NAME OF THE ASSIGNEE PREVIOUSLY RECORDED AT REEL: 67096 FRAME: 320. ASSIGNOR(S) HEREBY CONFIRMS THE ASSIGNMENT. Recorded Jun 26, 2024
From: TOTALENERGIES MARKETING SERVICES (PREVIOUSLY TOTAL MARKETING SERVICES)
To: TOTALENERGIES ONETECH
Reel/Frame 067845/0906 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Apr 12, 2024
From: TOTALENERGIES MARKETING SERVICES (PREVIOUSLY TOTAL MARKETING SERVICES)
To: TOTALENERGIES ONETECH (PREVIOUSLY TOTALENERGIES ONE TECH)
Reel/Frame 067096/0320 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Aug 12, 2021
From: VINCENT, RÉGIS
To: TOTAL MARKETING SERVICES
Reel/Frame 057159/0775 →