EP1622853A1 - Substances organiques iodees a faible poids moleculaire et procede pour les preparer - Google Patents

Substances organiques iodees a faible poids moleculaire et procede pour les preparer

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Publication number
EP1622853A1
EP1622853A1 EP04728814A EP04728814A EP1622853A1 EP 1622853 A1 EP1622853 A1 EP 1622853A1 EP 04728814 A EP04728814 A EP 04728814A EP 04728814 A EP04728814 A EP 04728814A EP 1622853 A1 EP1622853 A1 EP 1622853A1
Authority
EP
European Patent Office
Prior art keywords
substances
group
less
molecular mass
groups
Prior art date
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Withdrawn
Application number
EP04728814A
Other languages
German (de)
English (en)
Inventor
Patrick Lacroix-Desmazes
Romain Severac
Bernard Boutevin
Vincent Bodart
Vincent Kurowski
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
Solvay SA
Original Assignee
Solvay SA
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Priority claimed from BE2003/0255A external-priority patent/BE1015478A6/fr
Priority claimed from FR0309561A external-priority patent/FR2858319B1/fr
Application filed by Solvay SA filed Critical Solvay SA
Publication of EP1622853A1 publication Critical patent/EP1622853A1/fr
Withdrawn legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C69/00—Esters of carboxylic acids; Esters of carbonic or haloformic acids
    • C07C69/96—Esters of carbonic or haloformic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C41/00—Preparation of ethers; Preparation of compounds having groups, groups or groups
    • C07C41/01—Preparation of ethers
    • C07C41/05—Preparation of ethers by addition of compounds to unsaturated compounds
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C68/00—Preparation of esters of carbonic or haloformic acids

Definitions

  • the present invention relates to a process for preparing iodinated organic substances of low molecular mass, iodinated organic substances of low 5 molecular mass, and a process for preparing a polymer involving these iodinated organic substances of low molecular mass.
  • Patent US- ⁇ -5 144067 describes a process for the coproduction of an al yl iodide on the one hand, and of a mono- ⁇ -iodocarboxylic acid and/or anhydride on the other hand, according to which a mixture of an iodinated 10 compound, for example molecular iodine, a carboxylic anhydride, such as acetic anhydride, and a peroxide, such as hydrogen peroxide, is caused to react at a high temperature.
  • an iodinated 10 compound for example molecular iodine
  • a carboxylic anhydride such as acetic anhydride
  • a peroxide such as hydrogen peroxide
  • Patent US- ⁇ -5 430 208 describes a process for synthesizing 1-chloro-l- iodoethane according to which a hydriodic acid is reacted with vinyl chloride in 15 the presence of an iodine-containing catalyst which is organic (such as 1 ,2- diiodoethane) or inorganic (such as potassium iodide or molecular iodine).
  • an iodine-containing catalyst which is organic (such as 1 ,2- diiodoethane) or inorganic (such as potassium iodide or molecular iodine).
  • Heasley et al., J. Am. Chem. Soc, 1988, pp. 198-201 have synthesized various iodinated organic substances by reacting tert-buryl hypoiodide with various ethylenically unsaturated substances, in the presence of BF 3 or under the 20 action of ultraviolet radiation. In particular, they thus synthe
  • iodinated organic substances of low molecular mass thus produced are themselves very expensive. 30 It is also known that several iodinated organic substances of low molecular mass can be used as initiators for controlled free-radical polymerization
  • the subject of the present invention is a process of preparation which makes it possible to both have all the advantages of the prior art processes and to avoid all the disadvantages thereof.
  • the invention relates to a process for preparing one or more iodinated organic substances having a molecular mass of less than 2000 (substances (S)) using:
  • (C) molecular iodine which comprises the steps according to which: (1) 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 (2) the contents of the reactor are caused to react, while introducing therein the possible remainder of ( ⁇ ), 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) [mixture
  • one or more iodinated organic substances other than the substance(s) (S) may be optionally prepared by the process according to the invention [substances (S')].
  • the weight of the iodinated organic substance(s) (S') expressed relative to the weight of the substance(s) (S) is preferably less than 1, in a particularly preferred manner less than 0.2 and in a most particularly preferred manner less than 0.05.
  • the substance(s) (S) have a molecular mass preferably of less than 1000, in a particularly preferred manner of less than 500 and in a most particularly preferred manner of less than 250.
  • the substance(s) (S) have a number-average molecular mass advantageously of less than 500, preferably of less than 250.
  • peroxides is understood to mean both organic peroxides and inorganic peroxides.
  • ⁇ first family of substances among which the free -radical-generating substance is preferably chosen is that of organic peroxides.
  • dialkyl peroxides such as dicumyl peroxide, tert-butyl and cumyl peroxide and di-tert-butyl peroxide
  • - diacyl peroxides such as diisononanoyl peroxide, dioctanoyl peroxide, didecanoyl peroxide, dilauroyl peroxide, di(2-methylbenzoyl) peroxide, dibenzoyl peroxide and di(4-chlorobenzoyl) peroxide
  • dialkyl peroxydicarbonates such as diethyl peroxydicarbonate, diisopropyl peroxydicarbonate, di(sec-butyl) peroxydicarbonate, dimyristyl peroxydicarbonate, dicetyl peroxydicarbonate, di(2- ethyl peroxide
  • the organic peroxides are preferably chosen from dialkyl peroxides, diacyl peroxides, dialkyl peroxydicarbonates and peresters. They are chosen in a particularly preferred manner from dialkyl peroxides and dialkyl peroxydicarbonates, and in a most particularly preferred manner from dialkyl peroxides in which each of the alkyl chains comprises at most 4 carbon atoms and dialkyl peroxydicarbonates in which each of the alkyl chains comprises at most 4 carbon atoms. Di-tert-butyl peroxide and diethyl peroxydicarbonate gave excellent results.
  • the free-radical-generating substance is preferably chosen is that of the inorganic peroxides.
  • inorganic peroxides there may be mentioned: hydrogen peroxide; persulphates such as ammonium persulphate, sodium persulphate and potassium persulphate; perborates.
  • the inorganic peroxides are preferably persulphates. Ammonium persulphate gave excellent results.
  • a third family of substances among which the free-radical-generating substance is preferably chosen is that of diazo compounds.
  • diazo compounds there may be mentioned azobis(isobutyronitrile), azobis(2,4-dimethylvaleronitrile), azoamidines and azomidinium salts.
  • the diazo compounds preferably carry one or more nitrile groups. Azobis(isobutyronitrile) gave excellent results.
  • dialkyldiphenylalkanes there may be mentioned 3,4-dimethyl-3,4-diphenylhexane and 2,3-dimethyl-2,3-diphenylbutane.
  • trialkylboranes such as trimethylborane and triphenylborane (B(OO ⁇ ) 3 ), ⁇ & and ⁇ as defined above.
  • iniferter substances comprising at least one thiuram disulphide group
  • ⁇ symbols which are equal or different, being as defined above.
  • the substances of the family preferably have at most 3 carbon atoms.
  • they are chosen from vinyl chloride, vinylidene chloride, trichloroethylene, chlorotrifluoroethylene, vinyl fluoride, vinylidene fluoride, trifluoroethylene, tetrafluoroethylene and hexafluoropropylene.
  • they are chosen from vinyl chloride, vinylidene chloride and hexafluoropropylene.
  • the substances of the family (F3) preferably correspond to the formula
  • they are chosen from acrylic acid, methyl acrylate, ethyl acrylate, n- butyl acrylate, 2-ethylhexyl acrylate, methacrylic acid, methyl methacrylate and n-butyl methacrylate.
  • methyl acrylate gave excellent results.
  • organic substances containing at least one ethylenic double bond and capable of adding a free radical to their ethylenic double bond other than the abovementioned substances there may be mentioned ethylene, propylene and butadiene.
  • At least one of them is chosen from the substances of the family (FI) and at least another is chosen from the substances of the families (F3) and (F4).
  • at least one of them is chosen from vinyl chloride, vinylidene chloride and vinylidene fluoride and at least another is chosen from vinyl acetate, methyl acrylate and n- butyl acrylate.
  • one of them is vinylidene chloride and another is methyl acrylate.
  • the temperature at which the contents of the reactor are caused to react is advantageously from -50°C to 300°C, preferably from 0 to 150°C.
  • the whole of ( ⁇ ), (B) and (C) is introduced into the reactor in step (1).
  • the contents of the reactor are caused to react until the quantity of (B) consumed by the reaction no longer changes.
  • the number of moles of (C) expressed relative to the number of moles of ( ⁇ ) is advantageously greater than or equal to 90%, preferably greater than or equal to 100% and in a particularly preferred manner greater than or equal to 105%.
  • the number of moles of (C) expressed relative to the number of moles of (A) is advantageously less than 200% and preferably less than 150%.
  • the number of moles of (C) expressed relative to the number of moles of (B) is usually more than 0.5%.
  • the number of moles of (C) expressed relative to the number of moles of (B) is advantageously less than 200% and preferably less than 150%.
  • the process additionally comprises a step (3), following step (2), according to which the reaction in progress is stopped, for example by suddenly cooling the contents of the reactor.
  • the moment when the reaction in progress is stopped is advantageously that when the colour of the contents of the reactor changes from a dark colour to a light colour.
  • the number of moles of (C) expressed relative to the number of moles of ( ⁇ ) is advantageously less than 100% and preferably less than 90%.
  • the number of moles of (C) expressed relative to the number of moles of (A) is advantageously greater than or equal to 20%.
  • the number of moles of (C) expressed relative to the number of moles (B) is usually less than 100%. It may be less than 50%, or even less than 5%, and may even sometimes be less than 1%, without the good operation of the process according to the invention being affected.
  • the number of moles of (C) expressed relative to the number of moles of (B) is advantageously greater than or equal to 0.01% and preferably greater than 0.1%.
  • the process according to the invention advantageously comprises in addition one step, following step (2) and, furthermore, following step (3), when the process comprises the said step (3), according to which at least one substance (S) of the mixture (M) and possible other substances (S) contained in the mixture (M) are isolated.
  • the subject of the present invention is also iodinated organic substances for the preparation of which the process which is the subject of the invention is particularly well suited, and which all have the advantages of the iodinated organic substances of the prior art without exhibiting the disadvantages thereof.
  • the invention relates to a mixture comprising at least 2 iodinated organic substances having a molecular mass of less than 2000, corresponding respectively to the general formulae R-G x ⁇ CX 2 -CXY-) n -I and R- G x ⁇ CX 2 -CXY-) protest + ,-I, where:
  • R represents (i) a hydrogen atom, (ii) an atom of an alkali metal, (iii) a linear or branched C1-C2 0 alkyl group optionally substituted with one or more groups chosen from phenyl, carboxyl, hydroxyl, nitrile, amine or amidine groups, (iv) a Cs-C-s cycloalkyl group optionally substituted with one or more groups chosen from Ci-Cg alkyl groups and the nitrile group, or (v) a phenyl group, optionally substituted with one or more groups chosen from the C ⁇ -Cj alkyl groups and halogen atoms other than the iodine atom; x represents an integer equal to 0 or 1 ;
  • - Z represents (i) a hydrogen atom, or (ii) a saturated or ethylenically unsaturated or aromatic C ⁇ -C 2 o hydrocarbon group;
  • R, G, x, CX 2 -CXY and n are identical for the 2 substances which are the subject of the invention.
  • I is an iodine atom [substances (S2)].
  • the substances (S2) have a number-average molecular mass advantageously of less than 500 and preferably of less than 250.
  • Each of the substances (S2) has a molecular mass preferably of less than 1000, in a particularly preferred manner of less than 500 and in a most particularly preferred manner of less than 250.
  • alkali metal atoms capable of constituting the group R sodium and potassium may be mentioned.
  • unsubstituted alkyl groups capable of constituting the group R
  • substituted alkyl groups capable of constituting the group R there may be mentioned cumyl, -C(C ⁇ N)-(CH 3 ) 2 , (2-phenyl)propyl and (2-phenyl)butyl groups.
  • substituted or unsubstituted cycloalkyl groups capable of constituting the group R there maybe mentioned cyclohexyl and pinyl groups.
  • substituted phenyl groups capable of constituting the group R, there may be mentioned (2-methyl)phenyl and (4-chloro)phenyl groups.
  • n is usually less than 7, and often less than 5.
  • the mixture according to the invention is advantageously free of iodinated organic substances having a molecular mass of greater than or equal to 2000; it is preferably free of iodinated organic substances having a molecular mass of greater than or equal to 1000.
  • a first family of preferred substances (S2) is that of the substances (S2) where Y represents a halogen atom other than an iodine atom [family (F' 1)].
  • the groups (CX 2 -CXY) of the substances (S2) of the family (F'l) advantageously have at most 3 carbon atoms. They are preferably chosen from the groups (CH 2 -CHC1), ⁇ CH 2 -CC1 2 ), (CCl.-CHCT), (CF 2 -CFC1), (CH 2 -CHF), (CH 2 -CF 2 ), (CF 2 -CHF), ⁇ CF 2 -CF 2 ) and ⁇ CF 2 -CF(CF 3 )).
  • a second family of preferred substances (S2) is that of the substances (S2) where Y represents a phenyl group, optionally substituted with one or more atoms chosen from halogen atoms other than the iodine atom and Ci-Cs alkyl groups [family (F'2)].
  • the groups (CX 2 -CXY) of the substances (S2) of the family (F'2) advantageously correspond to the formula ⁇ CH 2 -CHY), Y as defined in the preceding paragraph.
  • the group (CH 2 -CH ⁇ ) where ⁇ denotes a phenyl group, is preferred.
  • the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'3) advantageously correspond to the formula ⁇ CH 2 -CHY), Y as defined in the preceding paragraph.
  • the acetyl group is preferred.
  • the groups (CX 2 -CXY) of the substances (S2) of the family (F'4) advantageously correspond either to the formula (CH 2 -CHY), or to the formula (CH 2 -C(CH 3 )Y), or else to the formula (CH 2 -CFY), Y as defined in the preceding paragraph. They preferably correspond to the formula ⁇ CH 2 -
  • they are chosen from the groups formed by the opening of the ethylenic double bond of one of the following substances: acrylic acid, methyl acrylate, ethyl acrylate, n-butyl acrylate, 2-ethylhexyl acrylate, methacrylic acid, methyl methacrylate and n-butyl methacrylate.
  • the invention also relates to an iodinated organic substance having a molecular mass of less than 2000, corresponding to the general formula R-G(CX 2 -CXY) q -I (I) with R, G, X, Y and I as defined above for the substances (S2) and where q represents an integer greater than 1 and less than 10.
  • the substance corresponding to the formula (I) has a molecular mass preferably of less than 1000, in aparticularly preferred manner of less than 500 and in a most particularly preferred manner of less than 250. q is usually less than 7, and often less than 5.
  • a first family of preferred substances corresponding to the formula (I) is that where Y represents a halogen atom other than an iodine atom [family (F"l).
  • the groups CX 2 -CXY) of the substances of the family (F"l) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'l).
  • ⁇ second family of preferred substances corresponding to the formula (I) is that where Y represents a phenyl group, optionally substituted with one or more atoms chosen from the halogen atoms other than the iodine atom and Ci-Cs alkyl groups [family (F"2)].
  • the groups (CX 2 -CXY) of the substances of the family (F"2) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'2).
  • the groups ⁇ CX 2 -CXY) of the substances of the family (F"3) satisfy the same characteristics and conditions preferably as the groups (CX 2 -CXY) of the substances (S2) of the family (F'3).
  • the groups (CX 2 -CXY) of the substances of the family (F"4) satisfy the same characteristics and conditions preferably as the groups (CX2-CXY) of the substances (S2) of the family (F'4).
  • the substance corresponding to the formula (II) has a molecular mass preferably of less than 1000, in a particularly preferred manner of less than 500 and in a most particularly preferred manner of less than 250.
  • a first family of preferred substances corresponding to the formula (II) is that where Y represents a halogen atom other than an iodine atom [family (F'"l)].
  • the groups (CX 2 -CXY) of the substances of the family (F'"l) satisfy the same characteristics and conditions preferably as the groups (CX 2 -CXY) of the substances (S2) of the family (F'l).
  • ⁇ second family of preferred substances corresponding to the formula (II) is that where Y represents a phenyl group, optionally substituted with one or more atoms chosen from halogen atoms other than the iodine atom and Ci-Cg alkyl groups [family (F'"2)].
  • the groups (CX 2 -CXY) of the substances of the family (F'"2) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'2).
  • the groups (CX 2 -CXY) of the substances of the family (F'"3) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'3).
  • the groups (CX 2 -CXY) of the substances of the family (F'"4) satisfy the same characteristics and conditions preferably as the groups (CX 2 -CXY) of the substances (S2) of the family (F'4).
  • the substance corresponding to the formula (HI) has a molecular mass preferably of less than 1000, in a particularly preferred manner of less than 500 and in a most particularly preferred manner of less than 250.
  • a first family of preferred substances corresponding to the formula (III) is that where Y represents a halogen atom other than an iodine atom (family [F IV 1)1.
  • the groups ⁇ CX 2 -CXY) of the substances of the family (F lv l) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'l).
  • a second family of preferred substances corresponding to the formula (III) is that where Y represents a phenyl group, preferably substituted with one or more atoms chosen from halogen atoms other than the iodine atom and Ci-Cs alkyl groups [family (F IV 2)].
  • the groups ⁇ CX 2 -CXY) of the substances of the family ⁇ w 2) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'2).
  • the groups ⁇ CX2-CXY) of the substances of the family (F ⁇ v 3) satisfy the same characteristics and conditions preferably as the groups CX 2 -CXY) of the substances (S2) of the family (F'3).
  • the groups (CX2-CXY) of the substances of the family (F ⁇ v 4) satisfy the same characteristics and conditions preferably as the groups ⁇ CX 2 -CXY) of the substances (S2) of the family (F'4).
  • the subject of the present invention is finally a process of controlled free- radical polymerization using the iodinated organic substances according to the invention or prepared by the process of synthesis according to the invention and which has all the advantages of the controlled free-radical polymerization processes of the prior art without exhibiting the disadvantages thereof.
  • the invention relates to a process for preparing a polymer by free-radical polymerization of at least one ethylenically unsaturated monomer, using in the polymerization: ( ⁇ ') the ethylenically unsaturated monomer,
  • ethylenically unsaturated monomers there may be mentioned vinyl esters as vinyl acetate, acrylic acid, acrylic esters such as methyl acrylate, methacrylic acid, methacrylic esters such as methyl methacrylate, nitriles and acrylic or methacrylic amides, styrene monomers such as styrene, olefin monomers such as butadiene and halogenated vinyl monomers.
  • halogenated vinyl monomers is understood to mean an ethylenically unsaturated monomer comprising one or more halogen atoms, and not comprising a heteroatom other than this or these halogen atoms.
  • halogenated vinyl monomers there may be mentioned vinyl chloride, vinylidene chloride, trichloroethylene, chloroprene and chlorotrifluoroethylene, vinyl fluoride, vinylidene fluoride, trifluoroethylene, tetrafluoroethylene, hexafluoropropylene and chlorotrifluoroethylene.
  • (A') preferably comprises at least one halogenated vinyl monomer.
  • ( ⁇ ') is composed of a halogenated vinyl monomer and, optionally in addition, of an acrylic ester.
  • the process of polymerization according to the invention advantageously comprises the steps according to which:
  • the process of polymerization according to the invention comprises the steps according to which: (1") at least a fraction of (A'), at least a fraction of (B'), and, where appropriate, at least a fraction of (D') are introduced into a reactor, the said reactor containing one or more substances (C) prepared beforehand by the process for preparing iodinated organic substances as described above,
  • the contents of the reactor are caused to react, while introducing therein the possible remainder of (A'), the possible remainder of (B'), the possible remainder of (C) and, where appropriate, the possible remainder of (D'), until a moment is reached when the contents of the reactor comprise the polymer.
  • the latter does not use in the polymerization a complex of a metal chosen from transition metals, lanthanides, actinides and group Ilia metals, and of a ligand of this metal.
  • the latter uses in the polymerization at least one complex of a metal chosen from transition metals, lanthanides, actinides and group ITIa metals, and of a ligand of this metal.
  • the process for preparing iodinated organic substances according to the invention has multiple advantages. It is very easy to carry out. It uses raw materials which are inexpensive and not very dangerous to handle. The iodinated organic substances thus produced are themselves inexpensive.
  • the tube was placed in an oven heated to 120°C, and its contents, initially dark brown in colour, were allowed to react therein until their complete decolorization was obtained, which decolorization occurred 15 hours after the tube was placed in the oven.
  • the products of the reaction were separated and their chemical nature determined by size exclusion chromatography applied to the crude contents of the reactor.
  • a plant composed of a Waters Associates pump equipped with a refractometric detector Shodex PJse-61 and two mixed-C PL-gel 5 ⁇ m columns from the company Polymer Laboratories.
  • the plant was standardized by means of a polystyrene standard. Tetrahydrofuran was used as eluent, at a flow rate of 1.0 ml/min.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
  • Polymerization Catalysts (AREA)
  • Polymerisation Methods In General (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

La présente invention concerne un procédé pour préparer une ou plusieurs substances organiques iodées qui présentent un poids moléculaire inférieur à 2000 (substances (S)) en utilisant (A) au moins une substance génératrice de radicaux libres, choisie parmi les peroxydes, les composés diazo, les dialkyldiphénylalcanes, les substances dérivées de tétraphényléthane, les boranes et les substances </= INIFERTER >/= comprenant au moins un groupe disulfure de thiurame, (B) une substance éthyléniquement insaturée qui peut ajouter un radical libre à sa double liaison éthylénique, et (C) de l'iode moléculaire. Ce procédé consiste à introduire au moins une fraction de (A), au moins une fraction de (B) et au moins une fraction de (C) dans un réacteur, à faire réagir les contenus du réacteur, tout en introduisant le résidu éventuel de (A), le résidu éventuel de (B) et le résidu éventuel de (C), jusqu'à ce que le contenu du réacteur soit un mélange comprenant une ou plusieurs substances (S). La présente invention concerne des substances organiques iodées pour la préparation desquelles le procédé susmentionné est particulièrement adapté.
EP04728814A 2003-04-22 2004-04-22 Substances organiques iodees a faible poids moleculaire et procede pour les preparer Withdrawn EP1622853A1 (fr)

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
BE2003/0255A BE1015478A6 (fr) 2003-04-22 2003-04-22 Procede de preparation de substances organiques iodees et substances organiques iodees.
US48725803P 2003-07-16 2003-07-16
FR0309561A FR2858319B1 (fr) 2003-08-01 2003-08-01 Procede de preparation de substances organiques iodees de faible masse moleculaire et substances organiques iodees de faible masse moleculaire
PCT/EP2004/050591 WO2004094356A1 (fr) 2003-04-22 2004-04-22 Substances organiques iodees a faible poids moleculaire et procede pour les preparer

Publications (1)

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EP1622853A1 true EP1622853A1 (fr) 2006-02-08

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EP (1) EP1622853A1 (fr)
JP (3) JP2006524215A (fr)
WO (1) WO2004094356A1 (fr)

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FR2903409A1 (fr) * 2006-07-04 2008-01-11 Solvay Procede de polymerisation radicalaire en dispersion aqueuse pour la preparation de polymeres

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EP1622853A1 (fr) * 2003-04-22 2006-02-08 SOLVAY (Société Anonyme) Substances organiques iodees a faible poids moleculaire et procede pour les preparer
WO2010013651A1 (fr) 2008-07-28 2010-02-04 大日精化工業株式会社 Dispersion aqueuse de pigment et ses applications
BR112021013425A2 (pt) 2019-02-11 2021-09-21 Dow Global Technologies Llc Método de produção de um polímero de ácido (met)acrílico, e, solução de polímero de ácido (met)acrílico
CA3129103A1 (fr) 2019-02-11 2020-08-20 Dow Global Technologies Llc Procede de polymerisation par transfert d'iode inverse et compositions en resultant
IT201900013836A1 (it) 2019-08-02 2021-02-02 Eni Spa Copolimeri lipofili comprendenti multi-blocchi polari, procedimento per la loro preparazione e loro utilizzo in composizioni lubrificanti.

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Publication number Priority date Publication date Assignee Title
FR2903409A1 (fr) * 2006-07-04 2008-01-11 Solvay Procede de polymerisation radicalaire en dispersion aqueuse pour la preparation de polymeres
US8541524B2 (en) 2006-07-04 2013-09-24 Solvay (Societe Anonyme) Free-radical polymerization process in aqueous dispersion for the preparation of a block copolymer at least one block of which is a block of a halogenated polymer

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JP2006524215A (ja) 2006-10-26
JP2011121953A (ja) 2011-06-23
JP2012072185A (ja) 2012-04-12
WO2004094356A1 (fr) 2004-11-04

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