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Acrylic Dispersants with Fused Aromatic Imide

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(19) TZZ¥Z__T (11) EP 3 066 166 B1 (12) EUROPEAN PATENT SPECIFICATION (45) Date of publication and mention (51) Int Cl.: of the grant of the patent: C09D 11/326 (2014.01) 28.03.2018 Bulletin 2018/13 (86) International application number: (21) Application number: 14802971.3 PCT/US2014/062875 (22) Date of filing: 29.10.2014 (87) International publication number: WO 2015/066163 (07.05.2015 Gazette 2015/18) (54) ACRYLIC DISPERSANTS WITH FUSED AROMATIC IMIDE ANCHOR GROUPS ACRYLDISPERGIERMITTEL MIT KONDENSIERTEN AROMATISCHEN IMIDANKERGRUPPEN DISPERSANTS ACRYLIQUES COMPORTANT DES GROUPES D’ANCRAGE À BASE D’IMIDES AROMATIQUES FUSIONNÉS (84) Designated Contracting States: (74) Representative: dompatent von Kreisler Selting AL AT BE BG CH CY CZ DE DK EE ES FI FR GB Werner - GR HR HU IE IS IT LI LT LU LV MC MK MT NL NO Partnerschaft von Patent- und Rechtsanwälten PL PT RO RS SE SI SK SM TR mbB Deichmannhaus am Dom (30) Priority: 04.11.2013 US 201361899455 P Bahnhofsvorplatz 1 50667 Köln (DE) (43) Date of publication of application: 14.09.2016 Bulletin 2016/37 (56) References cited: JP-A- 2013 053 200 US-A- 5 852 123 (73) Proprietor: Lubrizol Advanced Materials, Inc. US-A- 6 037 414 US-A1- 2010 240 825 Cleveland, OH 44141-3247 (US) • SIMMS J A: "New graft polymer pigment (72) Inventors: dispersant synthesis", PROGRESS IN ORGANIC • SHOOTER, Andrew J. COATINGS, ELSEVIER BV, NL; ENGINEERING Blackley, INFORMATION, INC., NEW YORK, NY, US, vol. 35, Greater Manchester M9 8ZS (GB) no. 1-4, 1 August 1999 (1999-08-01), pages • THETFORD, Dean 205-214, XP002733131, ISSN: 0300-9440, DOI: Blackley, 10.1016/S0300-9440(98)00067-8 [retrieved on Greater Manchester M9 8ZS (GB) 1999-10-11] • JENNINGS, Robert • WANG C-S: "PROPERTIES OF CONJUGATED Blakley, LADDER POLYMERS", TRENDS IN POLYMER Greater Manchester M9 8ZS (GB) SCIENCE, ELSEVIER SCIENCE PUBLISHERS • RICHARDS, Stuart N. B.V. AMSTERDAM, NL, vol. 1, no. 7, 1 July 1993 Blackley, (1993-07-01), pages199-205, XP000418351, ISSN: Greater Manchester M9 8ZS (GB) 0966-4793 Note: Within nine months of the publication of the mention of the grant of the European patent in the European Patent Bulletin, any person may give notice to the European Patent Office of opposition to that patent, in accordance with the Implementing Regulations. Notice of opposition shall not be deemed to have been filed until the opposition fee has been paid. (Art. 99(1) European Patent Convention). EP 3 066 166 B1 Printed by Jouve, 75001 PARIS (FR) EP 3 066 166 B1 Description FIELD OF INVENTION 5 [0001] The present invention relates to acrylic polymer dispersants having a least one imide anchoring group wherein the carbonyl groups of the imide are chemically bonded to a fused aromatic ring such as naphthalene. BACKGROUND OF THE INVENTION 10 [0002] The disclosed technology relates to polymeric acrylic dispersants. [0003] The disclosed technology, therefore, solves the problem of improving dispersant performance with a pendant aromatic imide anchoring segment. SUMMARY OF THE INVENTION 15 [0004] The disclosed technology provides a polymeric dispersant that resembles acrylic type polymers because the backbone of the polymer is derived from polymerizing acrylic type monomers comprising monomers selected from acrylic acid, esters of acrylic acid, amides of acrylic acid, styrene, acrylic acid esters carrying other functional groups containing oxygen or nitrogen, styrene carrying other functional groups containing oxygen or nitrogen, acrylic acid or styrene based 20 monomers having a chemically attached imide group where the carbonyls of the imide are directly chemically bonded to the carbon atoms of a fused aromatic ring, and optionally acrylic acid or styrene based macromonomers functionalized with solvent solubilizing chains of polyethers, polyesters, polyolefins, and/or polyacrylates. [0005] The polymeric dispersants will be characterized as having a) aromatic imide anchoring groups that interact favorably with particulate matter such as pigments or fillers and b) solvent-solubilizing groups that interact favorably with 25 the medium in which the particulate is dispersed. The dispersant will colloidally stabilize the particulate as a dispersed phase in the medium. The medium can be water, polar organic medium, or non-polar organic medium. The medium will dictate the solvent-solubilizing chains used in the dispersant as some solvent-solubilizing chains (e.g. polyethers) interact favorably with very polar medium such as water, other solvent-solubilizing chains (polyacrylates and polyolefins) interact favorably with non-polar medium. The medium can also be polymeric or a thermoplastic. Preferred final compositions 30 are inks, millbases, coatings, pigmented and/or filled plastics. [0006] The dispersants can be block copolymers having at least two blocks. The dispersants can have a block structure where the solvent-solubilizing chains are terminal and can have block structure where some of the solvent-solubilizing chains are essentially linear chains between two anchoring polymer backbone segments. A preferred version of the dispersant uses solvent solubilizing chains derived from ethylenically unsaturated macromonomers having attached 35 solvent-solubilizing chains. When said macromers are co-polymerized with the various acrylic and styrene type monomers the solvent-solubilizing chains are attached at one point to the dispersant backbone but the other end of the solvent- solubilizing chain has freedom to extend into the continuous medium. Dispersants with laterally attached pendant sol- ubilizing chains are often referred to as comb polymers. Dispersants having such structures are known from US 6037414, US 5852123 and US 2010/0240825. 40 [0007] According to the present invention there is provided a composition comprising a particulate solid, an organic or aqueous medium and a compound of Formula (1) where G is a CH3 or H group, or mixtures thereof and A,B,C and D are defined later. A is a moiety comprising a fused aromatic imide group. B and C are the ester portion of acrylate or styrene type monomers; D is a polyether, polyester, polyacrylate, and/or polyolefin chain that is linked to the backbone of formula 1 by various connecting groups. The E portion of formula 1 is known as the anchoring segment of the dispersant 45 and the F portion of formula 1 is known as the solubilizing portion. 50 55 [0008] In another embodiment these dispersants are made by living polymerizations of the ethylenically unsaturated 2 EP 3 066 166 B1 monomers and optional macromonomers. Living free radical polymerizations provide the opportunity to add specific monomers and macromonomers in specific orders during dispersant polymerization (making well controlled block and comb type polymeric dispersants). 5 DETAILED DESCRIPTION OF THE INVENTION [0009] Various preferred features and embodiments will be described below by way of non-limiting illustration. [0010] The amount of each chemical component described is presented exclusive of any solvent or diluent oil, which may be customarily present in the commercial material, that is, on an active chemical basis, unless otherwise indicated. 10 However, unless otherwise indicated, each chemical or composition referred to herein should be interpreted as being a commercial grade material which may contain the isomers, byproducts, derivatives, and other such materials which are normally understood to be present in the commercial grade. The use of (meth) in a monomer or repeat unit indicates an optional methyl group. [0011] It is known that some of the materials described above may interact in the final formulation, so that the com- 15 ponents of the final formulation may be different from those that are initially added. For instance, metal ions (of, e.g., a detergent) can migrate to other acidic or anionic sites of other molecules. The products formed thereby, including the products formed upon employing the composition of the present invention in its intended use, may not be susceptible of easy description. Nevertheless, all such modifications and reaction products are included within the scope of the present invention; the present invention encompasses the composition prepared by admixing the components described 20 above. [0012] One objective of the present invention is to provide compounds that are capable of improving the colour strength or other tinctorial properties, increasing a particulate solid load, and/or forming improved dispersions, having improved brightness of the final composition while also producing a composition with reduced viscosity good dispersion stability, reduced particle size and reduced particle size distribution (typically reduced to an average of 150 nm or less, for example 25 in the range of 70 -135 nm), reduced haze, improved gloss, and increased jetness (especially when the composition is black). The composition of the present invention may also be stable under ambient storage, and high temperature storage conditions, providing reduced discolouration or yellowing of the final coating. [0013] The dispersants of this disclosure use acrylic and/or styrene based monomers with pendant (laterally attached) imides where the carbonyl groups of the imide are chemically bonded to fused aromatic rings (such as naphthenic rings) 30 as anchor groups for particulate materials such as pigments and fillers in a continuous media such a polar or non-polar solvent. The resulting pendant groups from the backbone are shown in the formulas 2-9. These polar and non-polar solvents may be plastic materials or elastomeric
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  • Photoluminescence and Electron Migration Characteristics of Aromatic Poly(Amide-Imide) Containing 1-Naphth- Aldehyde and 4,4′-Diamino Diphenyl Ether

    Photoluminescence and Electron Migration Characteristics of Aromatic Poly(Amide-Imide) Containing 1-Naphth- Aldehyde and 4,4′-Diamino Diphenyl Ether

    http://www.e-polymers.org e-Polymers 2009, no. 016 ISSN 1618-7229 Photoluminescence and electron migration characteristics of aromatic poly(amide-imide) containing 1-naphth- aldehyde and 4,4′-diamino diphenyl ether Sepideh Khoee,* Somayeh Zamani *Polymer Laboratory, Chemistry Department, School of Science, University of Tehran, P. O. Box 14155-6455, Tehran, Iran; fax: +98 21 6649 5291; e-mail: [email protected] (Received: 23 June, 2008; published: 16 February, 2009) Abstract: A new photoactive polymer poly(amide-imide), was fabricated by reacting two synthesized monomers, N,N'-(4,4'-oxy-bis(4,1-phenylene))-bis-(1,3- dioxo-1,3-dihydroisobenzofuran-5-carbox amide) and N-(4,6-diamino-1,3,5- triazine-2-yl)-1-naphthamide. Polycondensation reaction of the two monomers was performed under 10 min microwave irradiation in o-cresol as solvent for producing a photoactive poly(amide-imide) in a quantitative yield. The resulting polymer was characterized by FT-IR, 1H-NMR, TGA techniques and its solvatochromic and fluorescence properties were investigated in different solvents. The poly(amide- imide) exhibit broad fluorescent band, and the fluorescence intensity is related to the intermolecular chain-chain or chain-solvent interaction. Also the self-quenching mechanism was studied according to the specific behavior of the polymer in different solvents and the self-quenching rate constant for the association reaction in the excited state (Kq) could be measured from the Stern-Volmer equation. This kind of fused system and diamines show various electron migration mechanisms and photoluminescent properties in the singlet excited states. Introduction The application of microwave energy to organic synthesis is known for a long time [1] and in the last decade was successfully applied to radical and condensation polymerization reactions [2, 3].