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WO2006138685A2 - Dispersions de colorant en phase gel pour compositions de revetement - Google Patents

Dispersions de colorant en phase gel pour compositions de revetement Download PDF

Info

Publication number
WO2006138685A2
WO2006138685A2 PCT/US2006/023687 US2006023687W WO2006138685A2 WO 2006138685 A2 WO2006138685 A2 WO 2006138685A2 US 2006023687 W US2006023687 W US 2006023687W WO 2006138685 A2 WO2006138685 A2 WO 2006138685A2
Authority
WO
WIPO (PCT)
Prior art keywords
colorant
reactive
gel
phase
dispersion
Prior art date
Application number
PCT/US2006/023687
Other languages
English (en)
Other versions
WO2006138685A3 (fr
Inventor
Paul M. Kayima
James M. Cameron
Original Assignee
The Sherwin-Williams Company
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 The Sherwin-Williams Company filed Critical The Sherwin-Williams Company
Priority to EP06773459A priority Critical patent/EP1891173A2/fr
Priority to MX2007016135A priority patent/MX2007016135A/es
Priority to BRPI0614046-7A priority patent/BRPI0614046A2/pt
Priority to CA2611494A priority patent/CA2611494C/fr
Publication of WO2006138685A2 publication Critical patent/WO2006138685A2/fr
Publication of WO2006138685A3 publication Critical patent/WO2006138685A3/fr

Links

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
    • C08G18/00—Polymeric products of isocyanates or isothiocyanates
    • C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
    • C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
    • C08G18/72—Polyisocyanates or polyisothiocyanates
    • C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
    • C08G18/78—Nitrogen
    • C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
    • C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups
    • C08G18/792—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate groups formed by oligomerisation of aliphatic and/or cycloaliphatic isocyanates or isothiocyanates
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/06—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain multicolour or other optical effects
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D5/00—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures
    • B05D5/06—Processes for applying liquids or other fluent materials to surfaces to obtain special surface effects, finishes or structures to obtain multicolour or other optical effects
    • B05D5/061—Special surface effect
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B44—DECORATIVE ARTS
    • B44F—SPECIAL DESIGNS OR PICTURES
    • B44F1/00—Designs or pictures characterised by special or unusual light effects
    • B44F1/08—Designs or pictures characterised by special or unusual light effects characterised by colour effects
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D17/00—Pigment pastes, e.g. for mixing in paints
    • C09D17/001—Pigment pastes, e.g. for mixing in paints in aqueous medium
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D175/00—Coating compositions based on polyureas or polyurethanes; Coating compositions based on derivatives of such polymers
    • C09D175/04—Polyurethanes
    • C09D175/06—Polyurethanes from polyesters
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D1/00—Processes for applying liquids or other fluent materials
    • B05D1/40—Distributing applied liquids or other fluent materials by members moving relatively to surface
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B05—SPRAYING OR ATOMISING IN GENERAL; APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D—PROCESSES FOR APPLYING FLUENT MATERIALS TO SURFACES, IN GENERAL
    • B05D7/00—Processes, other than flocking, specially adapted for applying liquids or other fluent materials to particular surfaces or for applying particular liquids or other fluent materials
    • B05D7/50—Multilayers
    • B05D7/52—Two layers
    • B05D7/54—No clear coat specified
    • B05D7/544—No clear coat specified the first layer is let to dry at least partially before applying the second layer

Definitions

  • the present invention is a gel-phase colorant comprising (a) a reaction product of: (1) a reactive material component, (2) a reactive colorant, and (3) a crosslinker having reactive groups capable of forming a bond with the reactive material component and the reactive colorant.
  • the present invention is also a novel gel-phase colorant dispersion comprising (a) a gel-phase colorant comprising the reaction product of (1) a reactive material component, (2) a reactive colorant, and (3) a crosslinker having reactive groups capable of forming a bond with the reactive material component and the reactive colorant; and (b) a dispersion medium, wherein the dispersion medium can be an aqueous or non- aqueous-based dispersion.
  • the gel-phase colorant dispersion of this invention can then be mixed or blended with typical coating materials.
  • This invention is also directed to a method of preparing coating compositions comprising a binder phase of an aqueous or non-aqueous-based dispersion and a gel-phase colorant dispersion, and in particular, a method comprising the steps of (1) preparing at least one gel-phase colorant dispersion comprising a gel-phase colorant comprising a reaction product of (a) a reactive material component; (b) a reactive colorant and (c) a crosslinker; dispersed in a dispersion medium; and (2) mixing or blending the gel-phase colorant dispersion with typical coating materials.
  • the coating composition can also comprise one or more independent gel-phase colorant dispersions.
  • This invention is also directed to a process for achieving a multicolor faux finish pattern on a surface utilizing a gel-phase colorant dispersion- based one-pack multiphase coating composition.
  • This invention is also directed to a two-layer coating system comprising a topcoat and an undercoat, wherein the topcoat is a coating composition comprising a gel- phase colorant dispersion comprising (a) a gel-phase colorant comprising (1) a reactive material component, (2) a reactive colorant, and (3) a crosslinker having reactive groups capable of forming a bond with the reactive material component and the reactive colorant; and (b) a dispersion medium; and wherein the undercoat is a waterborne coating composition comprising one or more highly water-absorbent pigments.
  • a gel- phase colorant dispersion comprising (a) a gel-phase colorant comprising (1) a reactive material component, (2) a reactive colorant, and (3) a crosslinker having reactive groups capable of forming a bond with the reactive material component and the reactive colorant; and (b) a dispersion medium
  • the undercoat is a waterborne coating composition comprising one or more highly water-absorbent pigments.
  • Figure 1 is a graphical representation showing the stages of the gel-phase colorant dispersion through the coating composition in accordance with the invention.
  • Figure 2 is a graphical representation showing the gel-phase colorant dispersion coating in the liquid state.
  • Figure 3 is a graphical representation of the gel-phase colorant dispersion coating of this invention before and after applicator imprint.
  • Figure 4 is a graphical representation of a cross-section of the coating on a substrate before and after an applicator imprint.
  • the gel-phase colorant dispersions comprises a gel-phase colorant comprising a reaction product of (1) a reactive material component, particularly those having active hydrogens such as hydroxy- or amine-functionality; (2) a reactive colorant, dispersed into a dispersion medium; and (3) a crosslinker, having reactive groups capable of forming a bond with the reactive material component and a reactive colorant.
  • the dispersion medium can comprise aqueous or non-aqueous-based solutions or emulsions.
  • the gel-phase colorant particles resulting from these reactions have a high affinity for the liquid medium (which can be aqueous or non-aqueous) in which they are dispersed and at all times are stable therein.
  • the gel-phase colorant dispersion comprises discrete gel-phase colorant color particles of sufficient size to be readily visible and produce a desirable color contrast to the naked eye.
  • the gel-phase colorant particles can be dispersed in an aqueous or non-aqueous medium of a color the same as or different from that of the gel-phase colorant.
  • Such gel-phase colorant particles provide the desirable color contrast and are readily visible to produce a faux finish product, which is an objective of the invention.
  • the gel-phase colorant particles are of such strength that they do not deform or change shape by the shear force imposed when the coating composition is mixed, shaken, agitated or applied to a desired substrate by a brush, roller, sprayer or other typical applicator means.
  • the reactive material component of this invention can include compounds having active hydrogens, epoxy compounds, carboxy compounds, and the like.
  • a desired crosslinking agent is any compound having reactive groups which will react with (1) the reactive groups of the reactive material component and (2) the reactive colorant. Since one function of the crosslinking agent is to attach the reactive colorant to the reactive material component, the crosslinking agent should have at least two distinct reactive groups - one that can react with the colorant, while the other reacts with the reactive material component.
  • the distinct reactive groups can be either the same or different functional groups. For example, one type of functional group may react preferentially with the colorant while a different functional group may react preferentially with the reactive material component.
  • crosslinking agent can also include a multiplicity of reactive groups for reaction with the colorant and the reactive material component.
  • Many useful crosslinking agents include isocyanates and polyisocyanates, which have a multiplicity of sites for reaction with the colorants or the reactive material component.
  • a gel-phase colorant is made by combining the reactive material component, crosslinking agent and reactive colorant together and then reacting (or allowing to react) under suitable conditions to form a gel- phase colorant.
  • suitable conditions are those conditions required to cause reaction of the crosslinking agent with the reactive material component and the reactive colorant.
  • a aqueous gel-phase colorant suitable for this invention include the use polyester polyols (such as Piothane 70-1000 HAI or Piothane 70-500, both commercially available from Panolam Industries International, Inc., Auburn, Maine) as the reactive material component; isocyanates (such as Desmodur N3600 commercially available from Bayer Corporation, Pittsburgh, Pennsylvania) as the crosslinker.
  • Reactive colorants contemplated by this invention include Blend-A-Color (commercially available from Degussa Corporation of Parsippany, New Jersey), which can be used alone or in combination with other colorants.
  • a reactive colorant component is present in a gel- phase colorant in a quantity that can vary from trace amount to about 50 weight percent or more, based on the weight of the gel-phase colorant.
  • the above components can be heated, or merely allowed sufficient time at ambient temperature to produce the desired reaction. Suitable conditions (for reaction) and relative amounts of each chosen reactive material component, reactive colorant and crosslinking agent are dictated by the chemical character of such components and the presence or absence of catalysts, and will be apparent to those skilled in the art.
  • the gel-phase colorant is then dispersed in an aqueous or non-aqueous medium to produce a desired gel-phase colorant dispersion.
  • the mode of dispersion that can include, but is not limited to, stirring, shaking, agitation with a blade, milling, and sonication, determines the size and shape of the gel-phase colorant particles.
  • the weight of the gel-phase colorant(s) can total up to about 50 weight percent, based on the total weight of the gel-phase colorant dispersion.
  • the coating composition of this invention can comprise one or more independent gel colorant dispersions, wherein each of the said gel colorant dispersions, either aqueous or non-aqueous, contains a different colorant so as to provide more random distribution of colorant entities.
  • the coating composition of the invention can also comprise an aqueous or non-aqueous dispersion or emulsion.
  • aqueous-based dispersions include, but are not limited to, water, latex emulsions, polyurethane dispersions, water-based alkyd (or alkyds modified with acrylic, urethane or styrene) emulsions, dispersions and solutions; water-based acrylic dispersions and solutions.
  • some latexes useful for this invention include, but are not limited to, Joncryl SCX2577 (commercially available from S.C.
  • the coating composition can be easily formulated by blending one or more gel-phase colorant dispersions with typical raw materials as needed to obtain desired application, stability, appearance, and performance properties. These include materials such as water, coalescing agents, humectants, co-binder, pigment slurries, colorants, rheology modifiers, amines, mildewcides and biocides. Desirable appearance results are obtained when the gel-phase colorant solids content in the coating formulation is above a critical value, typically of about 15% by weight. The appearance effect may become diminished as the gel-phase colorant content drops. Preferably, best patterns develop when there is a discernable difference between the gel-phase colorant and tinting colors.
  • the gel-phase colorant dispersion is present in the coating composition in a quantity up to 95 weight percent, and preferably in a quantity between about 65-90 weight percent, based on total coating composition weight.
  • the shape, size and color of the gel-phase colorant particles, and hence the dispersion and aesthetic appearance and integrity of the final coating film may depend on the following variables:
  • composition of the gel-phase colorant (type and ratios of reactants);
  • Another embodiment of this invention is a two-layer coating system comprising a topcoat, wherein the topcoat is a waterborne dispersion comprising the gel- phase colorant dispersion, and an undercoat, wherein the undercoat comprises a highly water absorbing pigment.
  • the undercoat of this invention should have a pigment volume concentration of at least 55, and can be between 55 and 80 or between 65 to 75.
  • the pigment utilized in the undercoat can be any highly water absorbent pigment that is water insoluble, including by way of nonlimiting example, aluminum silicate and calcium carbonate.
  • the undercoat can be formulated by adding the following ingredients under mild agitation.
  • the two-layer coating system is applied to obtain a multi-tone coating on a surface of a substrate by:
  • the undercoat and/or topcoat can be applied to the surface using brush, drawdown, roller, spray application, or any other method of the art, and allowed to dry .
  • the present invention has the special advantage of achieving different multicolor desirable effects and patterns.
  • the coating compositions of this invention can be applied to essentially any surface that is amenable to conventional coating techniques, by spray, roller, brush, or other applicators. Striking patterns can be made utilizing a variety of applicators. When the tinted coating composition is applied multi-directionally using an applicator providing a textured result, the coating develops a random pattern in which areas of varying film thickness display shades of varying color and sheen.
  • the gel-phase colorant is preferentially stamp-deposited onto the substrate surface, resulting in layering or stratification of the gel-phase color and the tinting color of the emulsion phase.
  • the thinner regions of the coating display more of the gel phase color, while the thicker areas exhibit more of the tinting color.
  • faux patterns comprising randomly distributed domains of two or more colors and any color combinations of these colors can be made.
  • the above gel-phase colorant can be dispersed in 630 parts of SC Johnson Joncryl SCX-2577 styrene- acrylic latex emulsion.
  • the following examples illustrate a topcoat formulation utilizing two different colored gel-phase colorant dispersions.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Paints Or Removers (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)

Abstract

La présente invention concerne une nouvelle dispersion de colorant en phase gel comprenant (a) un colorant en phase gel renfermant le produit de réaction (1) d'un constituant de matière réactive, (2) d'un colorant réactif, et (3) d'un agent de réticulation comprenant des groupes réactifs capables de former une liaison avec le constituant de matière réactive et le colorant réactif, et (b) un milieu de dispersion, ce milieu de dispersion pouvant être une dispersion à base aqueuse ou non aqueuse. La dispersion de colorant en phase gel de l'invention peut ensuite être mélangée avec des matières de revêtement classiques. L'invention concerne également un procédé de préparation de compositions de revêtement comprenant une phase de liaison d'une dispersion à base aqueuse ou non aqueuse et une dispersion de colorant en phase gel, et notamment un procédé consistant (1) à préparer au moins une dispersion de colorant en phase gel comprenant un colorant en phase gel renfermant un produit de réaction (a) d'un constituant de matière réactive, (b) d'un colorant réactif, et (c) d'un agent de réticulation comprenant des groupes réactifs capables de former une liaison avec le constituant de matière réactive et le colorant réactif, en dispersion dans un milieu de dispersion, et (2) à mélanger la dispersion de colorant en phase gel avec des matières de revêtement classiques. Cette composition de revêtement peut également comprendre une ou plusieurs dispersions de colorant en phase gel indépendantes. L'invention se rapporte en outre à un procédé permettant d'obtenir un motif de faux-fini multicolore sur une surface au moyen d'une composition de revêtement polyphasique en une seule solution à base d'une dispersion de colorant en phase gel. L'invention concerne également un système de revêtement bicouche comprenant une couche de finition et une sous-couche, la couche de finition étant une dispersion en phase aqueuse comprenant une dispersion de colorant en phase gel contenant un colorant en phase gel renfermant (a) un produit de réaction (1) d'un constituant de matière réactive, (2) d'un colorant réactif, et (3) d'un agent de réticulation comprenant des groupes réactifs capables de former une liaison avec le constituant de matière réactive et le colorant réactif, et (b) un milieu de dispersion, la sous-couche étant une dispersion en phase aqueuse comprenant un ou plusieurs pigments hautement hydroabsorbants.
PCT/US2006/023687 2005-06-17 2006-06-16 Dispersions de colorant en phase gel pour compositions de revetement WO2006138685A2 (fr)

Priority Applications (4)

Application Number Priority Date Filing Date Title
EP06773459A EP1891173A2 (fr) 2005-06-17 2006-06-16 Dispersions de colorant en phase gel pour compositions de revetement
MX2007016135A MX2007016135A (es) 2005-06-17 2006-06-16 Dispersiones de colorantes en fase de gel destinadas a composiciones para recubrimientos.
BRPI0614046-7A BRPI0614046A2 (pt) 2005-06-17 2006-06-16 dispersões corantes de fase gel para composições de revestimento
CA2611494A CA2611494C (fr) 2005-06-17 2006-06-16 Dispersions de colorant en phase gel pour compositions de revetement

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US69203205P 2005-06-17 2005-06-17
US60/692,032 2005-06-17

Publications (2)

Publication Number Publication Date
WO2006138685A2 true WO2006138685A2 (fr) 2006-12-28
WO2006138685A3 WO2006138685A3 (fr) 2007-06-07

Family

ID=37056475

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/US2006/023687 WO2006138685A2 (fr) 2005-06-17 2006-06-16 Dispersions de colorant en phase gel pour compositions de revetement

Country Status (6)

Country Link
US (1) US20060282959A1 (fr)
EP (1) EP1891173A2 (fr)
BR (1) BRPI0614046A2 (fr)
CA (1) CA2611494C (fr)
MX (1) MX2007016135A (fr)
WO (1) WO2006138685A2 (fr)

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102007023913A1 (de) * 2007-05-23 2008-11-27 Lanxess Deutschland Gmbh Pigmentzubereitungen von pastöser oder gelförmiger Konsistenz
US8647427B2 (en) * 2008-03-27 2014-02-11 Styron Europe Gmbh Polyvinyl ester-based latex coating compositions
AU2012253441B2 (en) 2011-05-10 2017-03-30 Archer Daniels Midland Company Dispersants having biobased compounds

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
AU3965389A (en) * 1988-07-11 1990-02-05 Nellcor Incorporated Hydrogel dye film sensing elements and their preparation
US5498685A (en) * 1993-04-27 1996-03-12 Minnesota Mining And Manufacturing Company Carboxylic-acid functional polyurethane polymers and their use in magnetic recording media
TW473525B (en) * 1994-12-16 2002-01-21 Bic Corp Erasable ink composition and marking instrument containing same
US5700851A (en) * 1995-10-17 1997-12-23 Tektronix, Inc. Ink-jet ink composition containing a colored polyurethane dispersion
US5786410A (en) * 1997-03-31 1998-07-28 Xerox Corporation Polyurethane dye based inks
GB9806791D0 (en) * 1998-03-31 1998-05-27 Zeneca Ltd Composition
GB0116678D0 (en) * 2001-07-09 2001-08-29 Clariant Int Ltd Inherently coloured polyurea and polyurethane
DE10154030A1 (de) * 2001-11-02 2003-05-22 Basf Coatings Ag Effektgeber, wässriger Beschichtungsstoff, Verfahren zu seiner Herstellung und seine Verwendung
JP4162545B2 (ja) * 2003-06-26 2008-10-08 エスケー化研株式会社 模様面の形成方法

Also Published As

Publication number Publication date
US20060282959A1 (en) 2006-12-21
CA2611494A1 (fr) 2006-12-28
WO2006138685A3 (fr) 2007-06-07
MX2007016135A (es) 2008-03-06
BRPI0614046A2 (pt) 2011-03-09
CA2611494C (fr) 2014-08-05
EP1891173A2 (fr) 2008-02-27

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