IP Library Granted Patent US 12,503,395
Granted Patent B2
US 12,503,395 · App. 17/786,407 · Granted Dec 23, 2025

Fluidizing compounds for hydraulic compositions

Inventors: Antoine Colas (Bourg-la-Reine, FR); Vincent Etienne Claude Froidevaux (Pairs, FR); Frédéric Leising (Avilly Saint Leonard, FR)
Assignees: CHRYSO; SAINT-GOBAIN PLACO
C04B24/32C04B28/02C04B2103/32C04B2103/34
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Quick Facts
Patent No.
US 12,503,395
App. No.
17/786,407
Granted
Dec 23, 2025
Kind
B2
Abstract

Disclosed is a compound with the following formula (I): as well as the use thereof, in particular as a chelating agent of positively charged ions, or as a fluidizing agent for hydraulic compositions. Also disclosed is a hydraulic composition comprising a compound with formula (I), at least one hydraulic binder, at least one aggregate, and water.

Claims (95)

1 . A compound with the following formula (I):

wherein:

M is chosen from the group consisting of H, alkaline and alkaline earth metals and + HNRR′ groups, R and R′ being chosen independently from each other from H, (C 1 -C 3 ) alkyl, either linear or branched, and alcohols in C 1 -C 3 , either linear or branched;

R 1 is chosen from the group consisting of H, A 1 and (C 1 -C 4 ) alkyl groups, either linear or branched, when A is described by formula (1) below, or, where A is described by formula (2) or (3) below, R 1 is chosen from the group consisting of H and (C 1 -C 4 ) alkyl groups, either linear or branched;

R 2 is chosen from the group consisting of H, OM, M being as defined above and from (C 1 -C 4 ) alkyl groups, either linear or branched;

A stands for:

a group A 1 with the following formula (1):

wherein:

n is an integer from 1 to 40;

m is an integer from 1 to 40; and

Z is chosen from the group consisting of:

 —CHR 3 —NH— groups, R 3 being chosen from the group consisting of H, COOH and (C 1 -C 6 ) alkyl groups, either linear or branched;

—C(═O)—NH— groups; and

—C(R 5 ) ═N— groups, where R 5 is H or Me;

* a group A 2 with the following formula (2):

wherein:

n is an integer from 1 to 40, preferentially from 1 to 31;

m is an integer from 1 to 40, preferentially from 1 to 31;

r is 0 or an integer from 1 to 6; and

M, R 1 and R 2 are as defined above in formula (I);

* a group A 3 with the following formula (3):

wherein:

n′ is an integer from 1 to 50;

the sum of m′+p′ varies from 1 to 6;

m′ is an integer from 1 to 5;

p′ is an integer from 1 to 5; and

M, R 1 and R 2 are as defined above in formula (I);

Z is as defined above in formula (1).

2 . The compound according to claim 1 , having the following formula (II):

wherein:

R 1 is chosen from the group consisting of H and (C 1 -C 4 ) alkyl groups, or stands for a group A 1 with formula (1) as defined in claim 1 ; and

M, R 2 , n, m are as defined in claim 1 .

3 . A hydraulic composition comprising:

the compound of claim 2 ,

at least one hydraulic binder,

at least one aggregate, and

water.

4 . The compound with formula (II) according to claim 2 , wherein:

R 2 is an OM group;

n varies from 19 to 31;

m varies from 3 to 10; and

Z is chosen from the group consisting of:

—CHR 3 —NH— groups, where R 3 is chosen from the group consisting of H, COOH and (C 1 -C 6 ) alkyl groups, either linear or branched; and

—C(═O)—NH— groups.

5 . A hydraulic composition comprising:

the compound of claim 4 ,

at least one hydraulic binder,

at least one aggregate, and

water.

6 . The compound with formula (II) according to claim 4 , wherein R 1 is H or stands for a group A 1 with formula (1).

7 . A hydraulic composition comprising:

the compound of claim 6 ,

at least one hydraulic binder,

at least one aggregate, and

water.

8 . The compound according to claim 1 , having the following formula (III):

wherein:

R 1 is chosen from the group consisting of H and (C 1 -C 4 ) alkyl groups; and

M, R 2 , n, m and r are as defined in claim 1 .

9 . A hydraulic composition comprising:

the compound of claim 8 ,

at least one hydraulic binder,

at least one aggregate, and

water.

10 . The compound with formula (III) according to claim 8 , wherein R 1 is H and R 2 is an OM group and r is 0 or varies from 1 to 3.

11 . A hydraulic composition comprising:

the compound of claim 10 ,

at least one hydraulic binder,

at least one aggregate, and

water.

12 . The compound according to claim 1 , described by the following formula (IV):

wherein:

R 1 is chosen from the group consisting of H and (C 1 -C 4 ) alkyl groups; and

M, R 2 , n′, m′ and p′ are as defined in claim 1 .

13 . The compound with formula (IV) according to claim 12 , wherein:

R 1 is H;

R 2 is an OM group; and

Z is chosen from the group consisting of:

—CHR 3 —NH— groups, where R 3 is chosen from the group consisting of H, COOH and (C 1 -C 6 ) alkyl groups, either linear or branched; and

—C(═O)—NH— groups.

14 . A hydraulic composition comprising:

the compound of claim 12 ,

at least one hydraulic binder,

at least one aggregate, and

water.

15 . A chelating agent of positively charged ions comprising a compound according to claim 1 .

16 . A hydraulic composition comprising:

a compound according to claim 1 ,

at least one hydraulic binder,

at least one aggregate, and

water.

17 . A fluidizing agent for hydraulic compositions comprising a compound according to claim 1 .

18 . A admixture to hydraulic binders comprising a compound according to claim 1 , alone or in combination with at least one plasticizer and/or superplasticizer.

19 . A method to decrease the sensitivity to phyllosilicate clays of a hydraulic composition, comprising adding a compound according to claim 1 into said hydraulic composition.

20 . A method to decrease the sensitivity to alkaline sulfates in solution of a hydraulic composition, comprising adding a compound according to claim 1 into said hydraulic composition.

Assignments (3)
MERGER Recorded Feb 4, 2026
From: CHRYSO
To: STARCIN HOLDING FRANCE
Reel/Frame 073687/0298 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 22, 2022
From: COLAS, ANTOINE; FROIDEVAUX, VINCENT ETIENNE CLAUDE
To: CHRYSO; SAINT-GOBAIN PLACO
Reel/Frame 061852/0512 →
EMPLOYMENT AGREEMENT Recorded Nov 22, 2022
From: LEISING, FRÉDÉRIC
To: CHRYSO
Reel/Frame 061984/0771 →