Plasticizers for aqueous suspensions of mineral particles and hydraulic binder pastes
View Patent ↗The invention relates to a compound of following formula (I): the preparation method thereof and the use of same.
1. A compound of following formula (I):
where:
n is an integer of between 1 and 100;
i is an integer varying from 1 to n, such that for each value of i, each R i independently represents a hydrogen atom, an alkyl, an aryl, a 1-(1-alkylalkoxy), a —[CH 2 —CH 2 —O] q -Alk radical in which q is an integer of between 1 and 20, and Alk represents an alkyl,
R′ is a hydrogen or an alkyl,
Q is a straight chain or branched alkylene group comprising 2 to 10 carbon atoms,
A 1 is an alkylene or alkylidene group comprising 1 to 6 carbon atoms, or an arylene group,
X 1 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a mono- or divalent cation, such that m 1 is 1 when X 1 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a monovalent cation, and m 1 is 2 when X 1 represents a divalent cation,
R represents a hydrogen, an alkyl with 1 to 6 carbon atoms, an aryl or an -A 2 -PO 3 X 2 2/m2 group where:
A 2 is an alkylene or alkylidene group comprising 1 to 6 carbon atoms, or an arylene group,
X 2 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a mono- or divalent, cation, such that m 2 is 1 when X 2 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a monovalent cation, and m 2 is 2 when X 2 represents a divalent cation,
co represents that the sequence of the consecutive units of the polymer is unspecified, and
* represents that the different units are grouped together head-to-tail.
2. The compound according to claim 1 , of following formula
where:
n, i, R i , R′, Q, X 1 , X 2 , m 1 and m 2 are such as defined in claim 1 , and
A 1 and A 2 are each independently an alkylene or alkylidene group comprising 1 to 6 carbon atoms, or an arylene group.
3. The compound according to claim 1 , wherein each R i independently represents a hydrogen, a methyl, an ethyl, an aryl, —CH(CH 3 )—OCH 2 CH 3 , —[CH 2 —CH 2 —O] q —CH 3 where q is an integer from 1 to 20.
4. The compound according to claim 1 , of following formula (III):
where:
R′, A 1 , R, Q, X 1 and m 1 are such as defined in claim 1 ,
R 1 and R 2 meet the definition given for R i in claim 1 ,
q 1 and q 2 are each independently an integer from 0 to 100, provided that the sum of q 1 and q 2 equals n, n being such as defined in claim 1 .
5. The compound according to claim 1 , of following formula (IV):
where:
R′, A 1 , A 2 , Q, X 1 , X 2 , m 1 and m 2 are such as defined in claim 1 ,
R 1 and R 2 meet the definition for R i given in claim 1 ,
q 1 and q 2 are each independently an integer of 0 to 100, provided that the sum of q 1 and q 2 equals n, n being such as defined in claim 1 .
6. The compound according to claim 1 , of following formula (VI):
where n 1 , R 1 , R 3 , Q, A 1 , A 2 , X 1 , X 2 , m 1 and m 2 are such as defined in claim 1 .
7. The compound according to claim 1 , of following formula (VIII):
where:
R′, Q, X 1 , X 2 , m 1 and m 2 are such as defined in claim 1 ,
R 1 and R 2 meet the definition for given in claim 1 ,
q 1 and q 2 are each independently an integer of 0 to 100, provided that the sum of q 1 and q 2 equals n, n being such as defined in claim 1 .
8. The compound according to claim 1 of following formula (X):
where:
R′, X 1 , X 2 , m 1 and m 2 are such as defined in claim 1 ,
R 1 and R 2 meet the definition for R 1 given in claim 1 ,
q 1 and q 2 are each independently an integer of 0 to 100, provided that the sum of q 1 and q 2 equals n, n being such as defined in claim 1 .
9. The compound according to claim 1 having one of the following formulas (XI), (XII), (XIII) and (XIV):
in which q 1 and q 2 are each independently an integer from 0 to 100, provided that the sum of q 1 and q 2 equals n, n being such as defined in claim 1 .
10. A method for preparing a compound of following formula (I):
where:
n is an integer of between 1 and 100;
i is an integer varying from 1 to n, such that for each value of i, each R i represents a hydrogen atom, an alkyl, an aryl, a 1-(1-alkylalkoxy), a —[CH 2 —CH 2 —O] q -Alk radical where q is an integer of 1 to 20 and Alk represents an alkyl;
R′ represents a hydrogen or an alkyl;
Q represents a straight chain or branched alkylene group comprising 2 to 10 carbon atoms;
A 1 independently represents an alkylene or alkylidene group comprising 1 to 6 carbon atoms, or an arylene group;
X 1 is a hydrogen, an alkyl with 1 to 5 carbon atoms or a mono- or divalent cation, such that m 1 is 1 when X 1 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a monovalent cation, and m 1 is 2 when X 1 represents a divalent cation;
R represents a hydrogen, an alkyl with 1 to 6 carbon atoms, an aryl or a-A 2 -PO 3 X 2 2/m2 group where:
A 2 represents an alkylene or alkylidene group with 1 to 6 carbon atoms, or an arylene group,
X 2 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a mono- or divalent cation, such that m 2 is 1 when X 2 represents a hydrogen, an alkyl with 1 to 5 carbon atoms or a monovalent cation, and m 2 is 2 when X 2 represents a divalent cation,
co represents that the sequence of the consecutive units of the polymer is unspecified, and
* represents that the different units are grouped together head-to-tail;
comprising the steps of:
(co)polymerizing in a basic medium at least one ether of glycidol in the presence of an anionic initiator carrying a primary amine function having the formula of —O-Q-NH 2 to obtain a polyglycerol with primary amine termination,
converting the primary amine function of the polyglycerol obtained at the preceding step to an amino-alkylene phosphonic group.
11. The method for preparing a formula (I) compound according to claim 10 further comprising a prior step to prepare the said glycidol ether from a compound of following formula (XX):
where Y is —OH, an alkylsulfonate or a halogen.
12. The method for preparing a formula (I) compound according to claim 10 , wherein X is a hydrogen or a cation and the conversion of the primary amine function of the polyglycerol with primary amine termination to an amino-alkylene phosphonic group is conducted by Moedritzer-Irani reaction, optionally followed by a basification step.
13. The method for preparing a formula (I) compound according to claim 10 , wherein X is an alkyl with 1 to 5 carbon atoms and the conversion of the primary amine function of the polyglycerol with primary amine termination to an amino-alkylene phosphonic group is conducted by Kabashnick-Fields reaction, optionally followed by a neutralization step.
14. An adjuvant comprising 1 to 50 weight % of at least one compound according to claim 1 and an aqueous, alcoholic or hydro-alcoholic solvent.
15. A method for maintaining the slump flow of hydraulic binders and suspensions of mineral particles comprising a step of adding the compound according to claim 1 to a hydraulic binder or to a suspension of mineral particles.
16. The compound according to claim 1 , wherein X 1 represents an alkaline, alkaline-earth or ammonium cation, and/or X 2 represents an alkaline, alkaline-earth or ammonium cation.
17. The compound according to claim 3 , wherein q is an integer from 1 to 5.
18. The compound according to claim 10 , wherein X 1 represents an alkaline, alkaline-earth or ammonium cation, and/or X 2 represents an alkaline, alkaline-earth or ammonium cation.
19. The method for preparing a formula (I) compound according to claim 11 , wherein Y is chlorine.