US 8,263,811 B2Granted

Iodinated organic substances of low molecular mass and process for preparing them

AssigneeSolvay (Societe Anonyme)

InventorsPatrick Lacroix-Desmazes, Romain Severac, Bernard Boutevin, Vincent Bodart, Vincent Kurowski

Life of this patent

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Abstract

Process for preparing one or more iodinated organic substances having a molecular mass of less than 2000 (substances (S)) using (A) at least one free-radical-generating substance chosen from peroxides, diazo compounds, dialkyldiphenylalkanes, substances derived from tetraphenylethane, boranes and iniferter substances comprising at least one thiuram disulphide group, (B) an ethylenically unsaturated substance capable of adding a free radical to its ethylenic double bond, (C) molecular iodine, which comprises the steps according to which at least a fraction of (A), at least a fraction of (B) and at least a fraction of (C) are introduced into a reactor, and then the contents of the reactor are caused to react, while introducing therein the possible remainder of (A), the possible remainder of (B) and the possible remainder of (C), until a moment is reached when the content of the reactor is a mixture comprising one or more substances (S). Iodinated organic substances for whose preparation the abovementioned process is particularly well suited.

Claims9

Dependent claims

A mixture comprising at least two different iodinated organic substances each having a molecular mass of less than 2000, corresponding respectively to the general formulae:

R-GxCX2—CXY—)n—I and R-GxCX2—CXYn+1—I,
where;
R represents (i) a hydrogen atom, (ii) an atom of an alkali metal, (iii) a linear or branched C1-C20 alkyl group optionally substituted with one or more groups chosen from phenyl, carboxyl, hydroxyl, nitrile, amine or amidine groups, (iv) a C3-C8 cycloalkyl group optionally substituted with one or more groups chosen from C1-C8 alkyl groups and the nitrile group, or (v) a phenyl group, optionally substituted with one or more groups chosen from the C1-C8 alkyl groups and halogen atoms other than the iodine atom;
x represents an integer equal to 0 or 1;
G represents —O—, —O—C(═O)—O—, —C(═O)—O— or —O—S(═O)p—O—;
if G is a group —C(═O)—O—, then its fragment C(═O) is linked to R and its fragment O linked to a group CX2;
p represents an integer equal to 1 or 2;
n represents an integer equal to 1 to 8;
the groups X represent, independently of each other and of Y, (i) a hydrogen atom, (ii) a halogen atom other than an iodine atom, or (iii) a linear or branched C1-C20 alkyl group;
Y represents (i) a halogen atom other than an iodine atom, (ii) a phenyl group optionally substituted with one or more atoms chosen from halogen atoms other than the iodine atom and C1-C8 alkyl groups, (iii) a group —O—C(═O)—Z, (iv) a nitrile group, (v) a group —C(═O)—O—Z, or (vi) a group —C(═O)—NZ2;
Z represents (i) a hydrogen atom, or (ii) a saturated or ethylenically unsaturated or aromatic C1-C20 hydrocarbon group;
R, G, x, CX2—CXY and n are identical for the two substances;
and
I is an iodine atom.

11 more elements

A process for preparing a polymer by free-radical polymerization of at least one ethylenically unsaturated monomer, comprising using in the polymerization:

(A′) the ethylenically unsaturated monomer,
(B′) at least one free-radical-generating agent chosen from peroxides, diazo compounds, dialkyldiphenylalkanes, substances derived from tetraphenylethane, boranes, iniferter substances comprising at least one thiuram disulphide group, styrene and styrene substances, and ultraviolet radiation,
(C′) at least one iodinated organic substance having a molecular mass of less than 2000 chosen from
(a) a mixture comprising at least two different iodinated organic substances corresponding respectively to the general formulae:
R-GxCX2—CXY—)n—I and R-GxCX2—CXYn+1—I,
where;
R represents (i) a hydrogen atom, (ii) an atom of an alkali metal, (iii) a linear or branched C1-C20 alkyl group optionally substituted with one or more groups chosen from phenyl, carboxyl, hydroxyl, nitrile, amine or amidine groups, (iv) a C3-C8 cycloalkyl group optionally substituted with one or more groups chosen from C1-C8 alkyl groups and the nitrile group, or (v) a phenyl group, optionally substituted with one or more groups chosen from the C1-C8 alkyl groups and halogen atoms other than the iodine atom;
x represents an integer equal to 0 or 1;
G represents —O—, —O—C(═O)—O—, —C(═O)—O— or —O—S(═O)p—O—;
if G is a group —C(═O)—O—, then its fragment C(═O) is linked to R and its fragment O linked to a group CX2;
p represents an integer equal to 1 or 2;
n represents an integer equal to 1 to 8;
the groups X represent, independently of each other and of Y, (i) a hydrogen atom, (ii) a halogen atom other than an iodine atom, or (iii) a linear or branched C1-C20 alkyl group;
Y represents (i) a halogen atom other than an iodine atom, (ii) a phenyl group optionally substituted with one or more atoms chosen from halogen atoms other than the iodine atom and C1-C8 alkyl groups, (iii) a group —O—C(═O)—Z, (iv) a nitrile group, (v) a group —C(═O)—O—Z, or (vi) a group —C(═O)—NZ2;
Z represents (i) a hydrogen atom, or (ii) a saturated or ethylenically unsaturated or aromatic C1-C20 hydrocarbon group;
R, G, x, CX2—CXY and n are identical for the two substances;
and
I is an iodine atom.
(b) an iodinated organic substance corresponding to the general formula R-GCX2—CXYq—I with R, G, p, X, Y, Z and I as defined above and where q represents an integer greater than 1 and less than 10,
(c) an iodinated organic substance corresponding to the general formula R—O—C(═O)—OCX2—CXYI with R, X, Y, Z and I as defined above, and
(d) an iodinated organic substance corresponding to the general formula R—O—S(═O)p—OCX2—CXYI with R, p, X, Y, Z and I as defined above,
and optionally in addition,
(D′) at least one complex of a metal chosen from transition metals, lanthanides, actinides and group IIIa metals, and of a ligand of this metal.

20 more elements

Dependencies are inferred from the claim text.

Facts

Application: 12/774,844Filed 6 May 2010 · division
Priority: BE 2003/025522 Apr 2003
Published: US 2010/0240850 A123 Sep 2010
Granted: 11 Sep 2012
Term ends: Not estimatedThe source records don’t support an estimate.

Classification8 codes

C07C 41/06
By addition of compounds to unsaturated compounds: by addition of organic compounds only
C07C 68/06
Preparation of esters of carbonic or haloformic acids: from organic carbonates
C08F 2/38
Processes of polymerisation: polymerisation using regulators, e.g. chain terminating agents , e.g. telomerisation
C08F 4/00
Polymerisation catalysts

Family

Application60/487,258Us provisional application · filed 16 Jul 2003
PCT/EP2004/050591Parent of this division · filed 22 Apr 2004
US 2010/0240850 A1Pre-grant publication · published 23 Sep 2010
Application10/553,993Parent of this division
US 7,741,524 B2Parent of this division
US 2007/0066781 A1Published application
US 8,263,811 B2This patent

From the US filing history. Foreign family members aren’t listed.