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WO2000064975A1 - Procédé de production d'une composition acrylique - Google Patents

Procédé de production d'une composition acrylique Download PDF

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Publication number
WO2000064975A1
WO2000064975A1 PCT/SE2000/000696 SE0000696W WO0064975A1 WO 2000064975 A1 WO2000064975 A1 WO 2000064975A1 SE 0000696 W SE0000696 W SE 0000696W WO 0064975 A1 WO0064975 A1 WO 0064975A1
Authority
WO
WIPO (PCT)
Prior art keywords
propanediol
process according
acid
alcohol
hydroxyalkyl
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.)
Ceased
Application number
PCT/SE2000/000696
Other languages
English (en)
Inventor
Bo Pettersson
Håkan BJÖRNBERG
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.)
Perstorp AB
Original Assignee
Perstorp AB
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
Application filed by Perstorp AB filed Critical Perstorp AB
Priority to AU46318/00A priority Critical patent/AU4631800A/en
Publication of WO2000064975A1 publication Critical patent/WO2000064975A1/fr
Anticipated expiration legal-status Critical
Ceased legal-status Critical Current

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Classifications

    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G83/00—Macromolecular compounds not provided for in groups C08G2/00 - C08G81/00
    • C08G83/002—Dendritic macromolecules
    • C08G83/003—Dendrimers
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/02—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds
    • C08G63/60—Polyesters derived from hydroxycarboxylic acids or from polycarboxylic acids and polyhydroxy compounds derived from the reaction of a mixture of hydroxy carboxylic acids, polycarboxylic acids and polyhydroxy compounds
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G63/00—Macromolecular compounds obtained by reactions forming a carboxylic ester link in the main chain of the macromolecule
    • C08G63/91—Polymers modified by chemical after-treatment

Definitions

  • the present invention relates to a process for production of an acrylic composition comprising at least one dendritic polyester acrylate oligomer and at least one acrylate monomer.
  • Acrylic compositions for said and other applications often comprise a number of various components, such as one or more polyester acrylates, for example polyester acrylate oligomers and polymers, and one or more functional monomers, for example esters of an alcohol and an acrylic acid.
  • Functional monomers work, besides being monomers, also as viscosity reducing diluents for said oligomers and polymers.
  • an acrylate such as film forming, curing, drying and the like
  • properties of an acrylate are determined by for instance the molecular weight and molecular structure as well as the chemical and physical structure of said acrylate.
  • Dendritic macromolecules such as dendritic polyesters, have gained a major interest as said molecules in various applications normally exhibit many unique properties not possible to obtain using conventionally branched and linear products, as disclosed in the Swedish patent nos.
  • Dendritic polymers comprise hyperbranched species having a certain degree of polydispersity and monodiperse dendrimers. Dendritic molecules are further discussed in for instance "Dendritic Molecules - Concepts, Syntheses, Perspectives" by G.R. Newkome, C.N. Moorefield and F.
  • Acrylic products having a well defined, tailor-made and/or unique structures can thus be produced by acrylation of dendritic polyesters having for instance one or more terminal hydroxyl groups.
  • the unique structure of dendritic polyesters makes production of for instance acrylic oligomers having a high molecular weight and a high acrylic functionality combined with a low viscosity in relation to the molecular weight, which is a desired relation in the production and use of for instance acrylic oligomers and monomers.
  • Dendritic structures, including hyperbranched molecules and dendrimers give furthermore a unique balance between for example film hardness, surface hardness, adhesion and flexibility. Problems have, however, occurred during acrylation and recovery of dendritic polyesters.
  • a commonly used process during said recovery and refining often include water leaching of unreacted acrylic acid.
  • the high molecular weight and the high polarity of dendritic polyesters tend in this context to yield stable or comparatively stable emulsions, which substantially obstruct said recovery and refining.
  • a dendritic polyester optionally partially chain terminated or functionalised, having at least one terminal hydroxyl group, prior to acrylation is diluted or mixed with at least one alcohol having at least one hydroxyl group and a molecular weight of at most 2000, such as 60-1500 or 100-1000, which alcohol preferably is liquid at a temperature of 20-50°C or yields liquid mixtures with said dendritic polyester at said temperature.
  • Obtained mixture is subsequently acrylated using common and well known methods, such as reaction with at least one compound comprising at least one acrylic unsaturation.
  • a reaction mixture comprising an acrylic composition comprising at least one dendritic polyester oligomer and at least one acrylic monomer is yielded in said acrylation.
  • the acrylic composition can subsequently be recovered and refined by means of known methods, such as said water leaching, without formation of disturbing stable emulsions. Acrylation as well as recovery and refining are, furthermore, facilitated as the polyester/alcohol mixture normally has a viscosity being lower than included polyester.
  • Various embodiments of the process of the present invention comprise mixtures wherein the alcohol is a diol, such as an ethylene glycol, a 1,2- or 1,3-propylene glycol, a butanediol or a di, tri or polyglycol, for example a diethylene glycol, a triethylene glycol, a polyethylene glycol, a dipropylene glycol, a tripropylene glycol, a polypropylene glycol or a glycol polymer such as a polymer comprising one or more ethylene glycols and one or more propylene glycols.
  • the alcohol is a diol, such as an ethylene glycol, a 1,2- or 1,3-propylene glycol, a butanediol or a di, tri or polyglycol, for example a diethylene glycol, a triethylene glycol, a polyethylene glycol, a dipropylene glycol, a tripropylene glycol, a polypropylene glycol
  • Alcohols being reaction products between at least one 2-hydroxyalkyl-l,3-propanediol, 2-alkyl-2-hydroxyalkyl-l,3-propanediol or 2,2-di(hydroxyalkyl)-l,3-propanediol and at least one alkylene oxide at a molar ratio said 1,3-propanediol to said alkylene oxide of between 1 :0.2 and 1:50, such as between 1:1 and 1:20 or being a reaction product between a dimer, trimer or polymer of said 1,3-propanediol and at least one alkylene oxide at a molar ratio said dimer, trimer or polymer to said alkylene oxide of between 1:0.2 and 1 :50, such as between 1 :1 and 1:20.
  • reaction products can suitably be exemplified by alkoxylated, such as ethoxylated and/or propoxylated, trimethylolethane, trimethylolpropane, pentaerythritol, ditrimethylolethane, ditrimethylolpropane and dipentaerythritol.
  • alkoxylated such as ethoxylated and/or propoxylated
  • trimethylolethane trimethylolpropane
  • pentaerythritol ditrimethylolethane
  • ditrimethylolpropane ditrimethylolpropane and dipentaerythritol.
  • the alcohol can furthermore and advantageously be a linear or branched alkanol, such as a C ⁇ -C 4 alkanol or preferably a C 4 - 2 alkanol, such as a butanol, a heptanol, a hexanol, an octanol, a nonanol, a decanol and/or a dodecanol, and/or be a 1,3-dioxane alcohol or a 1,3-dioxolane alcohol, such as a 5-hydroxy-l,3-dioxolane, a 5-hydroxy- 1,3-dioxane, a 5-hydroxyalkyl- 1,3-dioxane, a 5-alkyl-5-hydroxyalkyl- 1,3-dioxane and/or a 5,5-di(hydroxyalkyl)-l,3-dioxane.
  • a linear or branched alkanol such
  • Alkoxylated 1,3-dioxane alcohols can be exemplified by for instance ethoxylated and/or propoxylated 5-hydroxymethyl-l,3-dioxane and 5,5-di(hydroxymethyl)-l,3-dioxane.
  • Alkyl is in above disclosed embodiments preferably and independently C 1 -C 12 alkanyl or C 2 -C ⁇ 2 alkenyl.
  • the alkylene oxide is likewise preferably ethylene oxide, propylene oxide, butylene oxide, phenylethylene oxide (styrene oxide) or a mixture of two or more alkylene oxides.
  • the dendritic polyester which is included in the mixture of the present process, is in preferred embodiments built up from a core molecule, having one or more hydroxyl or epoxide groups, and one or more dendrons bonded to said groups.
  • a dendron comprises preferably two or more branching generations built up from at least one hydroxy and/or epoxy functional carboxylic acid, having at least one carboxyl group and at least two hydroxyl and/or epoxide groups, and optionally one or more spacing generations built up from at least one monohydroxy or monoepoxy functional monocarboxylic acid and/or at least one lactone.
  • the dendritic polyester can alternatively be equal to said dendron.
  • the dendritic polyester can furthermore be partially chain terminated or functionalised, whereby it has at least one terminal hydroxyl group, optionally in combination with one or more epoxide, alkenyl, amino, amide, aminoamide, thiol, anhydride, carboxyl, cyano, phosphate, phosphite, phosphin, suphate and/or sulphite groups or the like.
  • Embodiments of the process according to the present invention comprise at least dendritic polyester having a core molecule.
  • Said core molecule is in said embodiments preferably a 1,3-propanediol, such as a 2-alkyl- 1,3-propanediol, a 2,2-dialkyl- 1,3-propanediol, a 2-hydroxy-2-alkyl- 1,3-propanediol, a 2-hydroxyalkyl-2-alkyl- 1,3-propanediol, a 2,2-di(hydroxyalkyl)-l,3-propanediol, a 2-hydroxyalkoxy-2-alkyl-l,3-propanediol or a 2,2-di(hydroxyalkoxy)- 1,3-propanediol or a dimer, trimer or polymer of a said
  • 1,3-propanediol such as a 2-alkyl- 1,3-propaned
  • Alkyl is preferably and independently C 1 -C 12 alkanyl or C 2 -C 1 alkenyl and alkoxy is, likewise preferably and independently, ethoxy, propoxy or butoxy comprising 1 to
  • Said core molecules can suitably be exemplified by 2-butyl-2-ethyl- 1,3-propanediol, neopentyl glycol, trimethylolethane, trimethylolpropane, pentaerythritol, ditrimethylolethane, ditrimethylolpropane, anhydroennea-heptitol and dipentaerythritol and reaction products between a said di, tri or polyalcohol and at least one alkylene oxide, such as ethylene oxide, propylene oxide or butylene oxide, at a molar ratio alcohol to alkylene oxide of between 1:0.2 and 1 :50, such as between 1:1 and 1 :20.
  • alkylene oxide such as ethylene oxide, propylene oxide or butylene oxide
  • Preferred embodiments of the process according to the present invention furthermore comprise a dendritic polyester wherein one or more dendrons comprise at least one generation built up from at least one di, tri or polyhydroxy functional monocarboxylic acid.
  • Said carboxylic acid can suitably be exemplified by dimethylolpropionic acid, ⁇ , ⁇ -bis(hydroxymethyl)butyric acid, ⁇ , ⁇ -bis(hydroxymethyl)valeric acid, ⁇ , ⁇ -bis(hydroxy)propionic acid, 3,5-dihydroxybenzoic acid, ⁇ , ⁇ , ⁇ -tris(hydroxymethyl)acetic acid, citric acid and heptonic acid.
  • a dendron can, furthermore, optionally comprise at least one generation built up from at least one monohydroxy functional monocarboxylic acid or lactone, which acid or lactone suitably can be exemplified by hydroxyvaleric acid, hydroxypropionic acid, hydroxypivalic acid, glycolide, ⁇ -valerolactone, ⁇ -propiolactone and ⁇ -caprolactone.
  • the dendritic polyester included in the process of the present invention can furthermore in various embodiments be partially chain terminated through for instance reaction with at least one alkanyl, cycloalkanyl, alkenyl, cycloalkenyl, alkynyl or aryl compound, such as a mono, di, tri or polyfunctional carboxylic acid, which carboxylic acid suitably can be exemplified by saturated or unsaturated monocarboxylic acids and dicarboxylic acids having up to 24, such as 6-18, carbon atoms.
  • the dendritic polyester and the alcohol is, in the most preferred embodiments of the process of the present invention, prior to acrylation mixed in a weight ratio polyester to alcohol of between 90:10 and 10:90, such as between 25:75 and 75:25 or between 40:60 and 60:40.
  • the acrylation is preferably a direct reaction, such as esterification, with acrylic acid, methacrylic acid, crotonic acid ( ⁇ -methacrylic acid) and/or a direct reaction with an anhydride and or a halide corresponding to a said acrylic acid, preferably at a molar ratio hydroxyl groups to said acid, anhydride and/or halide of between 1:0.1 and 1:5, such as between 1:0.5 and 1:1.5.
  • Further acrylic compounds suitable for acrylation of the polyester/alcohol mixture according to the present process include for example epoxide or anhydride functional acrylates and methacrylates such as glycidylmethacrylate.
  • Example 1 shows preparation of an acrylic composition according to the invention and measurements of phase separation.
  • Example 2 and 3 show a comparative acrylation outside the scope of the invention and evaluation results in comparison with Example 1.
  • Example 4-6 show evaluations of products obtained in Examples 1 and 3.
  • the reaction mixture was at room temperature pored into a 2 1 beaker provided with a magnetic stirrer and a pH electrode.
  • the solution was under stirring neutralised by addition of 425 ml of 1% NaOH (aq) until a pH of 7.0 was obtained.
  • the mixture was now pored into a 2 1 separation funnel and the time till phase separation was measured. Complete separation of organic phase and water phase was obtained within 30 min.
  • the water phase was removed and the organic phase was washed with 2 x 500 ml of water, including removal of water phase between washings. Phase separation was checked and complete separation was in both washings obtained within 30 min.
  • the washed organic phase was subsequently evaporated in a roll evaporator applying vacuum and allowing air to bubble through.
  • An acrylated final product was recovered as a low viscous, clear and colourless liquid.
  • the reaction mixture was at room temperature pored into a 2 1 beaker provided with a magnetic stirrer and a pH electrode.
  • the solution was under stirring neutralised by addition of 425 ml of 1% NaOH (aq) until a pH of 7.0 was obtained.
  • the mixture was now pored into a 2 1 separation funnel and the time till phase separation was measured. Complete separation of organic phase and water phase was obtained over night (> 12 h).
  • the water phase was removed and the organic phase was washed with 2 x 500 ml of water, including removal of water phase between washings as above.
  • the organic phase was refined as in Example 1, whereby a final product was obtained as a viscous, transparent, yellowish product.
  • Product according to the present invention exhibited a substantially lower viscosity.
  • the product according to Example 1 exhibited, furthermore, a substantially lower colour value compared to product according to Example 3.
  • lacquer formulations were prepared by addition of a commercially available photoinitiator (DarocureTM 1173, Ciba Geigy, Switzerland) to the product obtained in Example 1 and Example 3 and to a commercially available acrylate based on ethoxylated trimethylolpropane (Sartomer SR454TM). Following lacquer formulations were obtained:
  • the three lacquers according to Example 4 were coated at a film thickness of 30 ⁇ m on glass panels and UN cured in a UN oven (Wallace Knight, 20 m/min, 240 mJ/m 2 ) using 1, 2 and 4 passages through the oven. Obtained cured lacquer films were of a very good quality without failure and having a high surface gloss. The cured lacquer films were conditioned at 23°C and 50% relative humidity for 24 hours. The filmhardness was subsequently measured as K ⁇ nig seconds (Ks) using a K ⁇ nig pendulum.
  • Example 1 Product according to the present invention (Example 1) exhibited very good reactivity and was equal in quality to Example 3. Furthermore, lacquer according to Examples 1 and 3 exhibited higher initial reactivity than SR454.
  • a hydroxyfunctional dendritic polyester (Boltorn ® H20, Perstorp Specialty Chemicals, Sweden) was mixed at 20 %-w/w with tripropylene glycol yielding below viscosity
  • Tripropylene glycol %-w/w: 80
  • glycerol for instance glycerol, ethoxylated glycerol and propoxylated glycerol, and other types of ethoxylated as well as propoxylated alcohols.

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  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Organic Chemistry (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyesters Or Polycarbonates (AREA)
  • Macromonomer-Based Addition Polymer (AREA)
  • Polyethers (AREA)

Abstract

L'invention concerne un procédé de production d'une composition acrylique renfermant au moins un oligomère acrylique de polyester dendritique et au moins un monomère acrylique. Ledit procédé consiste à mélanger le polyester dendritique au moins, lequel polymère comporte un ou plusieurs groupes hydroxyle, et un alcool au moins, ledit alcool comportant un ou plusieurs groupes hydroxyle et ayant un poids moléculaire inférieur ou égal à 2000. Le mélange ainsi obtenu est ensuite acrylé par réaction avec un composé au moins comprenant une au moins une insaturation acrylique, ce qui permet d'obtenir un mélange de réaction renfermant un oligomère acrylique de polyester dendritique au moins et un monomère acrylique au moins, et de récupérer la composition acrylique à partir dudit mélange de réaction.
PCT/SE2000/000696 1999-04-27 2000-04-12 Procédé de production d'une composition acrylique Ceased WO2000064975A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
AU46318/00A AU4631800A (en) 1999-04-27 2000-04-12 Process for production of an acrylate composition

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
SE9901517A SE514075C2 (sv) 1999-04-27 1999-04-27 Förfarande för tillverkning av en akrylatkomposition innefattande minst en dendritisk polyesterakrylatoligomer och minst en akrylatmonomer
SE9901517-4 1999-04-27

Publications (1)

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WO2000064975A1 true WO2000064975A1 (fr) 2000-11-02

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AU (1) AU4631800A (fr)
SE (1) SE514075C2 (fr)
WO (1) WO2000064975A1 (fr)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004016701A1 (fr) * 2002-08-16 2004-02-26 Perstorp Specialty Chemicals Ab Dispersion d'homopolymere ou de copolymere hydrophile
WO2004016700A1 (fr) * 2002-08-16 2004-02-26 Celanese Emulsion Norden Ab Dispersion de copolymeres en phase aqueuse
FR2862651A1 (fr) * 2003-11-24 2005-05-27 Rhodia Cons Spec Ltd Nouveaux dendrimeres a terminaisons bisphosphoniques et derives, leur procede de preparation et leur utilisation
FR2862650A1 (fr) * 2003-11-24 2005-05-27 Rhodia Cons Spec Ltd Nouveaux dendrimeres a terminaisons monophosphoniques, leur procede de preparation et leur utilisation
US7189456B2 (en) 2004-03-04 2007-03-13 Transitions Optical, Inc. Photochromic optical article
WO2007030352A2 (fr) 2005-09-07 2007-03-15 Transitions Optical, Inc. Article optique multifocal photochrome
JP2009506193A (ja) * 2005-08-31 2009-02-12 トランジションズ オプティカル， インコーポレイテッド 樹枝状高分子アクリレートを含むフォトクロミック物品
WO2009156400A1 (fr) 2008-06-23 2009-12-30 Sicpa Holding Sa Encre pour l'impression intaglio comprenant des dendrimères
WO2010145993A2 (fr) 2009-06-15 2010-12-23 Basf Se Microcapsules contenant des polymères fortement ramifiés en tant que réticulants
US7906214B2 (en) 2007-01-26 2011-03-15 Transitions Optical, Inc. Optical elements comprising compatiblizing coatings and methods of making the same
US8236905B2 (en) 2003-10-14 2012-08-07 Basf Aktiengesellschaft Hyperbranched polymers having ethylenically unsaturated groups
US20130237627A1 (en) * 2010-11-15 2013-09-12 Shanghai Weikai Chemicals Co., Ltd. Crosslinkable curing super-branched polyester and cured product and preparation method thereof
EP2735903A1 (fr) 2012-11-22 2014-05-28 Eastman Kodak Company Précurseurs de plaque d'impression lithographique négative comprenant un matériau liant hyper-ramifié
US20150158003A1 (en) * 2013-12-06 2015-06-11 Microtek Laboratories, Inc. Microcapsules having acrylic polymeric shells and methods of making same

Families Citing this family (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN116396474B (zh) * 2023-04-10 2024-06-18 宜兴市江山生物科技有限公司 一种具有多种用途的超支化聚醚酯及其制备方法

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WO1993017060A1 (fr) * 1992-02-26 1993-09-02 Perstorp Ab Macromolecule dendritique, procede d'elaboration et utilisation
WO1996013558A1 (fr) * 1994-10-27 1996-05-09 Perstorp Ab Composition de liant insature
WO1996019537A1 (fr) * 1994-12-21 1996-06-27 Perstorp Ab Produit thermodurcissable

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO1993017060A1 (fr) * 1992-02-26 1993-09-02 Perstorp Ab Macromolecule dendritique, procede d'elaboration et utilisation
WO1996013558A1 (fr) * 1994-10-27 1996-05-09 Perstorp Ab Composition de liant insature
WO1996019537A1 (fr) * 1994-12-21 1996-06-27 Perstorp Ab Produit thermodurcissable

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* Cited by examiner, † Cited by third party
Title
MATS JOHANSSON ET AL.: "Hyperbranched aliphatic polyesters as base for thermoset resins", POLYM. MATER. SCI. ENG.,, vol. 77, 1997, pages 124 - 125, XP002931219 *

Cited By (25)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2004016700A1 (fr) * 2002-08-16 2004-02-26 Celanese Emulsion Norden Ab Dispersion de copolymeres en phase aqueuse
WO2004016701A1 (fr) * 2002-08-16 2004-02-26 Perstorp Specialty Chemicals Ab Dispersion d'homopolymere ou de copolymere hydrophile
US7235600B2 (en) 2002-08-16 2007-06-26 Celanese Emulsion Norden Ab Waterborne copolymer dispersion
US8236905B2 (en) 2003-10-14 2012-08-07 Basf Aktiengesellschaft Hyperbranched polymers having ethylenically unsaturated groups
US7838625B2 (en) 2003-11-24 2010-11-23 Rhodia Uk Ltd. Dendritic polymers having biphosphonic terminations, derivatives thereof, method for preparing them, and their use
FR2862651A1 (fr) * 2003-11-24 2005-05-27 Rhodia Cons Spec Ltd Nouveaux dendrimeres a terminaisons bisphosphoniques et derives, leur procede de preparation et leur utilisation
FR2862650A1 (fr) * 2003-11-24 2005-05-27 Rhodia Cons Spec Ltd Nouveaux dendrimeres a terminaisons monophosphoniques, leur procede de preparation et leur utilisation
WO2005052032A1 (fr) * 2003-11-24 2005-06-09 Rhodia Uk Limited Nouveaux dendrimeres a terminaisons monophosphoniques, leur procede de preparation et leur utilisation.
WO2005052031A1 (fr) * 2003-11-24 2005-06-09 Rhodia Uk Ltd Nouveaux dendrimeres a terminaisons bisphosphoniques et derives, leur procede de preparation et leur utilisation
US8039580B2 (en) 2003-11-24 2011-10-18 Rhodia Uk Ltd. Dendritic polymers having monophosphonic terminations, method for preparing them, and their use
CN1902263B (zh) * 2003-11-24 2011-07-27 罗狄亚英国有限公司 具有单膦酸端基的新型树枝状聚合物,其制备方法和用途
US7189456B2 (en) 2004-03-04 2007-03-13 Transitions Optical, Inc. Photochromic optical article
US7666331B2 (en) 2005-08-31 2010-02-23 Transitions Optical, Inc. Photochromic article
JP2010270340A (ja) * 2005-08-31 2010-12-02 Transitions Optical Inc 樹枝状高分子アクリレートを含むフォトクロミック物品
JP2009506193A (ja) * 2005-08-31 2009-02-12 トランジションズ オプティカル， インコーポレイテッド 樹枝状高分子アクリレートを含むフォトクロミック物品
US7258437B2 (en) 2005-09-07 2007-08-21 Transitions Optical, Inc. Photochromic multifocal optical article
WO2007030352A2 (fr) 2005-09-07 2007-03-15 Transitions Optical, Inc. Article optique multifocal photochrome
US7906214B2 (en) 2007-01-26 2011-03-15 Transitions Optical, Inc. Optical elements comprising compatiblizing coatings and methods of making the same
US8540813B2 (en) 2008-06-23 2013-09-24 Sicpa Holding Sa Intaglio printing ink comprising dendrimers
WO2009156400A1 (fr) 2008-06-23 2009-12-30 Sicpa Holding Sa Encre pour l'impression intaglio comprenant des dendrimères
WO2010145993A2 (fr) 2009-06-15 2010-12-23 Basf Se Microcapsules contenant des polymères fortement ramifiés en tant que réticulants
US20130237627A1 (en) * 2010-11-15 2013-09-12 Shanghai Weikai Chemicals Co., Ltd. Crosslinkable curing super-branched polyester and cured product and preparation method thereof
US8912246B2 (en) * 2010-11-15 2014-12-16 Shanghai Weikai Optoelectronics New Materials Co., Ltd. Crosslinkable curing super-branched polyester and cured product and preparation method thereof
EP2735903A1 (fr) 2012-11-22 2014-05-28 Eastman Kodak Company Précurseurs de plaque d'impression lithographique négative comprenant un matériau liant hyper-ramifié
US20150158003A1 (en) * 2013-12-06 2015-06-11 Microtek Laboratories, Inc. Microcapsules having acrylic polymeric shells and methods of making same

Also Published As

Publication number Publication date
AU4631800A (en) 2000-11-10
SE9901517D0 (sv) 1999-04-27
SE514075C2 (sv) 2000-12-18
SE9901517L (sv) 2000-10-28

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