Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2002-04-26
2003-12-30
Pezzuto, Helen L. (Department: 1713)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C524S555000, C524S815000, C526S312000, C526S328500, C560S221000, C560S222000
Reexamination Certificate
active
06670508
ABSTRACT:
The present invention relates to the monomer of formula (I) having two quaternary amino groups:
this being the chloride of 1,3-bis(dimethylbenzylammonium)isopropyl acrylate (also known by the abbreviated term S-ADAMQUAT 2 BZ).
Patent Application No. 00-00834 filed on Jan. 24, 2000 entitled “Procédé de fabrication de monomères à deux groupes amino quaternaires et les (co)polymères obtenus à partir de ces monomères” [Process for manufacturing monomers having two quaternary amino groups and the (co)polymers obtained from these monomers] discloses the preparation of the monomer of formula (I) in aqueous solution by the process consisting in introducing the quaternizing agent benzyl chloride into a solution, in chloroform, dichloromethane or dichloroethane, of (2-dimethylamino-1-dimethylaminomethyl)ethyl acrylate (also known by the abbreviated term S-ADAME), at a temperature of from 35 to 80° C., the reaction then being permitted to proceed at the said temperature to complete or substantially complete consumption of the S-ADAME, and an aqueous solution of this compound then being isolated, with the option to remove the water where appropriate.
The French Patent Application No. 00-00833, filed Jan. 24, 2000 and entitled “Dispersions aqueuses sans sel de copolymères hydrosolubles à base de monomères cationiques, leur procédé de fabrication et leurs applications” [Salt-free aqueous dispersions of water-soluble copolymers based on cationic monomers, process for their manufacture, and their applications] discloses a salt-free aqueous dispersion of a water-soluble copolymer obtained from a composition of monomers comprising, for 100 molar parts:
(a) from 0.5 to 99.5 molar parts of at least one monomer which may be S-ADAMQUAT 2BZ; and
(b) from 99.5 to 0.5 molar parts of at least one monomer which may be selected, inter alia, from acryloxyethyltrimethylammonium chloride (ADAMQUAT MC) and acryloxyethyldimethylbenzyl-ammonium chloride (Adamquat BZ);
where the said composition of monomers may include, for 100 molar parts of (a)+(b):
(c) up to 30 molar parts of at least one hydrophobic monomer; and/or
(d) up to 10 molar parts of at least one crosslinking monomer; and/or
(e) up to 30 molar parts of at least one amphiphilic monomer.
These salt-free aqueous dispersions in particular comprise, for 100 parts by weight:
(A) from 5 to 50 parts by weight of dispersed copolymer based on the composition of monomers (a) to (e) defined above; and
(B) from 0.5 to 25 parts by weight of at least one dispersant (co)polymer,
the remainder being water.
They are manufactured by aqueous free-radical polymerization of the monomer(s) (a) to (e) as defined above in the presence of the polymer dispersant(s) (B), and they are used as flocculators for treating aqueous effluent; fibre-retention agents and fillers in papermaking processes; agents facilitating the cleaning of media, such as textile; agents for filler dispersion; agents for inhibiting the transfer of pigments and colorants on various media, such as textile, thickeners, and dehydrators.
French Patent Application No. 00-00832, filed Jan. 24, 2000 and entitled “Dispersions aqueuses salines de (co)polymères hydrosolubles à base de monomères cationiques, leur procédé de fabrication et leurs applications” [Saline aqueous dispersions of water-soluble (co)polymers based on cationic monomers, process for their manufacture, and their applications] discloses a saline aqueous dispersion of a water-soluble (co)polymer obtained from a composition of water-soluble monomers comprising, for 100 molar parts:
(1) from 2 to 100 molar parts of at least one monomer which may be S-ADAMQUAT 2BZ; and
(2) from 0 to 95 molar parts of at least one monomer which may be selected, inter alia, from acryloxyethyltrimethylammonium chloride (ADAMQUAT MC) and acryloxyethyldimethylbenzyl-ammonium chloride (Adamquat BZ);
where it is possible for other monomers (2) to (5) described in that French patent application also to be present, including monomer (3):
(3) from 0 to 95 molar parts of at least one monomer which may be selected, inter alia, from acryloxyethyltrimethylammonium chloride (ADAMQUAT MC) and acryloxyethyldimethylbenzyl-ammonium chloride (Adamquat BZ).
These saline aqueous dispersions in particular comprise, for 100 parts by weight:
(A) from 10 50 parts by weight of dispersed (co)polymer based on the composition of the said monomers (1) to (5);
(B) from 0.5 to 25 parts by weight of at least one dispersant (co)polymer; and
(C) from 10 to 45 parts by weight of at least one inorganic salt such that the aqueous solution dissolves the dispersant (co)polymer without dissolving the dispersed (co)polymer formed in the course of polymerization,
the remainder being water.
They are manufactured by aqueous saline free-radical polymerization of the monomer(s) (1) to (5) in the presence of the polymer dispersant(s) (B) and the said inorganic salt(s) (C), and they are used as flocculators for treating aqueous effluent; dehydrators; fibre-retention agents and fillers in papermaking processes; agents facilitating the cleaning of media, such as textile; agents for filler dispersion; agents for inhibiting the transfer of pigments and colorants on various media, such as textile, and thickeners.
French Patent Application No. 00-00835, filed Jan. 24, 2000 and entitled “Dispersions aqueuses salines de copolymères hydrosolubles à base de monomères cationiques, leur procédé de fabrication et leurs applications” [Saline aqueous dispersions of water-soluble copolymers based on cationic monomers, process for their manufacture, and their applications] describes compositions likewise based on S-ADAMQUAT-2BZ, on ADAMQUAT MC and on ADAMQUAT BZ.
Now, it appears that the current process for synthesizing S-ADAMQUAT 2BZ is not capable of cost-effective industrial use. Furthermore, since it involves the presence of a solvent, the environmental situation is not ideal (VOCs problem).
Therefore, a solution to this double problem has been discovered that, surprisingly, the use of at least one of ADAMQUAT BZ, ADAMQUAT MC and S-ADAMQUAT 2BZ instead of chloroform or methylene chloride which are used currently permits the reaction time to be reduced and thus increases productivity by at least a factor of two, while removing the environmental constraint related to the solvent.
An object of the present invention, therefore, is a process for the manufacture of the compound of formula (I):
alone or in combination with at least one monomer of formula (II):
in which R represents —CH
3
or —CH
2
C
6
H
5
,
characterized in that the benzyl chloride quaternizing agent is introduced into a solution, in a solvent selected from the compounds of the formulae (I) and (II) and mixtures of these, of the compound of the formula (III):
at a temperature of from 35 to 60° C., in particular from 40 to 50° C., and then water is added and the reaction is allowed to proceed to complete or substantially complete conversion of the compound (III), and that an aqueous solution of desired N-hydroxyethylethylenediaminetriacetate. The sequestering agents are generally added in the form of an aqueous solution, because they are generally available in that form. Thus, pentasodium diethylenetriaminepentaacetate marketed as VERSENEX 80 takes the form of an aqueous solution of about 40% by weight strength.
Depending on the circumstances, the process according to the invention leads to an aqueous solution of compound (I) solely, a concentration of compound (I) being from 50 to 75% by weight, or leads to an aqueous solution of compounds (I) and (II), the composition of the aqueous solution being the following, for 100 parts by weight:
compound (I):
from 10 to 70% by weight
compound(s) (II):
from 10 to 70% by weight
water:
from 20 to 80% by weight
These solutions may be used for polymerization directly or mixed with other comonomers.
Another object of the present invention is homopolymers or copolymers containing units of monomer (I) and where appropriate at least one unit monomer (II), where this or these monomer(s)
Atofina
Millen White Zelano & Branigan P.C.
Pezzuto Helen L.
LandOfFree
Process for manufacturing the chloride of 1,3-bis-... does not yet have a rating. At this time, there are no reviews or comments for this patent.
If you have personal experience with Process for manufacturing the chloride of 1,3-bis-..., we encourage you to share that experience with our LandOfFree.com community. Your opinion is very important and Process for manufacturing the chloride of 1,3-bis-... will most certainly appreciate the feedback.
Profile ID: LFUS-PAI-O-3146907