EP1208169A1 - Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung - Google Patents

Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung

Info

Publication number
EP1208169A1
EP1208169A1 EP00964073A EP00964073A EP1208169A1 EP 1208169 A1 EP1208169 A1 EP 1208169A1 EP 00964073 A EP00964073 A EP 00964073A EP 00964073 A EP00964073 A EP 00964073A EP 1208169 A1 EP1208169 A1 EP 1208169A1
Authority
EP
European Patent Office
Prior art keywords
radiation curable
dispersion
cellulose ester
curable resin
cellulose
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Withdrawn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
EP00964073A
Other languages
English (en)
French (fr)
Inventor
Klaas Jan Hendrik Kruithof
Ann Kerstin Birgitta Kjellqvist Lindell
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.)
Akzo Nobel NV
Original Assignee
Akzo Nobel NV
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 Akzo Nobel NV filed Critical Akzo Nobel NV
Priority to EP00964073A priority Critical patent/EP1208169A1/de
Publication of EP1208169A1 publication Critical patent/EP1208169A1/de
Withdrawn legal-status Critical Current

Links

Classifications

    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D101/00Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
    • C09D101/08Cellulose derivatives
    • C09D101/10Esters of organic acids
    • CCHEMISTRY; METALLURGY
    • C09DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09DCOATING 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
    • C09D101/00Coating compositions based on cellulose, modified cellulose, or cellulose derivatives
    • C09D101/08Cellulose derivatives
    • C09D101/16Esters of inorganic acids
    • C09D101/18Cellulose nitrate

Definitions

  • the present invention relates to a process for the preparation of a waterborne radiation curable lacquer composition comprising a radiation curable resin and a cellulose ester, and the lacquer composition thus obtained.
  • a UV curable coating composition is disclosed based on cellulose nitrate and at least one UV curable unsaturated resin. Optionally other components are present in the composition.
  • the composition is prepared by dissolving the cellulose nitrate, the unsaturated resin, and the optional components in a suitable organic solvent or a mixture of solvents. The thus obtained high-viscous cellulose nitrate-containing paste is then emulsified at elevated temperature under high shear forces by the addition of water and optionally a dispersant.
  • a drawback of this method is the need to use a substantial amount of organic solvent in the preparation of the paste containing the cellulose nitrate and the unsaturated resin. After the dispersion of these components in water, the organic solvent is still present and will evaporate during cure of the coating composition. The emission of most organic solvents contributes to the VOC level of the coating composition. The VOC level is restricted by present day legislation. Such restriction is expected to increase in the near future. In normal use, the water is evaporated from the coating composition and the components in the composition are cured.
  • a drawback of this known method is tackiness of the coated surface after evaporation of the water. To prevent sticking of particles to the tacky surface of a freshly coated object, special care is needed to place the object in a dust-free area. In particular in industrial coating processes this presents a major problem, e.g., when the object is a
  • the unsaturated resin(s) present in the compositions prepared according to these known processes show(s) a relatively low cure response upon radiation. This leads to a prolonged application process. Further, the lacquer compositions of EP 0 154 241 show insufficient water, coffee, and ethanol resistance.
  • UV curable cellulose based lacquers are disclosed. These compositions contain a relatively large amount of reactive diluents. A problem with these coatings on porous substrates is the penetration of the coating composition into the pores. Since the radiation does not reach these areas, uncured coating material is the result. This can give health, safety, and environmental problems, e.g., when the substrate is cut or sanded. These problems occur even years after the lacquer has been applied. The same problems can be found in other substrates comprising shadow areas, e.g. in 3- D substrates, or when a pigmented lacquer is used.
  • a solvent borne radiation curable coating composition comprising a cellulose ester. These compositions all contain a relatively large amount of solvent that has to be evaporated before curing of the composition.
  • water containing radiation curable coating compositions comprising a cellulose ester.
  • a mixture comprising a radiation curable resin and the cellulose ester is dispersed in water in a way comparable to the process disclosed in EP 0 154 241.
  • This process comprises the following steps: preparation of a dispersion which is substantially free of radiation curable components comprising cellulose ester and water, by dissolving the cellulose ester in an appropriate solvent and emulsifying the thus obtained solution by the addition of water and optionally a dispersant, mixing said cellulose-containing dispersion with a radiation curable resin until a homogeneous dispersion is obtained.
  • the process according to the present invention offers a high degree of freedom with regard to the formulation of coating compositions.
  • the cellulose ester- comprising dispersion can be mixed with virtually any radiation curable resin. This mixing can be done at any stage of the preparation of the lacquer composition.
  • the type of radiation curable resin can be adjusted to the requirements of the substrate and/or the desired coating.
  • the present invention further relates to a radiation curable lacquer composition which shows improved behaviour over known radiation curable lacquer compositions based on cellulose esters, in particular with respect to cure speed, water, coffee, and ethanol resistance.
  • the lacquer composition according to the present invention also shows improved chemical resistance, scratch resistance, and pendulum hardness. Further, this new lacquer composition shows no yellowing after curing.
  • a dispersion is a distribution of finely divided particles (solid or liquid) in a
  • a dispersion which is not curable by radiation, other than infrared radiation is considered to be a dispersion which is substantially free of radiation curable components, - a radiation curable resin or dispersion comprising a radiation curable resin is a compound which can be cured by radiation having a wavelength ⁇ ⁇
  • a radiation curable lacquer composition is a lacquer which is cured by using electromagnetic radiation having a wavelength ⁇ ⁇ 500 nm.
  • electromagnetic radiation having a wavelength ⁇ ⁇ 500 nm are, e.g., UV radiation or electron beam radiation.
  • cellulose esters eligible for use according to the invention are the known nitrate esters, as well as esters based on acetobutyrate and acetopropionate. Preference is given to the use of cellulose nitrate, cellulose acetobutyrate, cellulose acetopropionate, or cellulose acetate, as well as mixtures thereof.
  • a process for the preparation of a dispersion comprising a cellulose ester is disclosed.
  • a cellulose ester-comprising dispersion is prepared by dissolving a cellulose ester in an appropriate organic solvent and dispersing the thus obtained solution by the addition of water and optionally a dispersant.
  • the organic solvent can be (partially) removed after the dispersion has been obtained, e.g., by distillation.
  • the dispersion comprising the cellulose ester can further comprise other resins which are compatible with the cellulose ester employed to improve the properties of the coating composition.
  • examples of these other resins are: alkyd/polyester resins, epoxy resins, polyethers, polyurethanes, amino resins, and acrylic or vinyl polymers, or mixtures thereof.
  • portions of these other resins can be functionalised with reactive groups.
  • These other resins can be incorporated into the cellulose ester-comprising dispersion at any moment in time. They can be mixed in prior to dispersion or when the dispersion is prepared. However, it is also possible to add these other resins after the preparation of the cellulose ester-comprising dispersion. Further, it is possible to add the other resins to the cellulose ester-comprising dispersion at or after the mixing with the radiation curable resin.
  • the waterborne radiation curable lacquer composition is obtainable by mixing a dispersion comprising a cellulose ester and a radiation curable resin.
  • a dispersion comprising a cellulose ester and a radiation curable resin.
  • any water dispersible or water dilutable radiation curable resin known to the man skilled in the art can be used.
  • the addition of such resins to the cellulose ester-comprising dispersion can result in a change in the viscosity of the lacquer composition.
  • the viscosity then has to be adjusted for the proper application of the lacquer composition.
  • the dispersion comprising the radiation curable resin can be prepared by using any dispersible radiation curable resin known to the man skilled in the art.
  • dispersions are all acrylate dispersions, polyester acrylate dispersions, aliphatic polyurethane dispersions, epoxy acrylate dispersions, urethane acrylate dispersions, urethane epoxy acrylate dispersions, aromatic urethane acrylate dispersions, and aliphatic urethane acrylate dispersions.
  • Suitable dispersions are commercially available under the following tradenames: Alberdingk LUX 11 , Alberdingk LUX 22, Alberdingk LUX 33 (all ex Alberdingk Boley), UV-Link SA 01 , UV-Link AP 03 (both ex ADD APT), Halwedrol UV 14, Halwedrol UV 20, Halwedrol UV 74, Halwedrol UV 94, Halwedrol TN 6306/40W (all ex H ⁇ ttenes- Albertus), Primal E 3120 (ex Rohm & Haas), Laromer LR 8895, Laromer LR 8983, Laromer LR 8949 (all ex BASF), Daotan VTW 1236, Viaktin VTE 6155W, Viaktin VTE 6166W, Viaktin VTE 6165W, Viaktin VTE 5972W, Viaktin VTE 6169/45W (all ex Vianova), NeoRad R 440, NeoRad R
  • the dispersion comprising the radiation curable resin has a solids content (based on the total weight of the dispersion) of 20 - 80%, preferably 30 - 60%. Normally 3 - 40 pbw, preferably 5 - 30 pbw, of the dispersion comprising the radiation curable resin are mixed with 100 pbw of the dispersion comprising the cellulose ester.
  • a photoinitiator is added to the lacquer composition.
  • Suitable photoinitiators for use in the lacquer composition according to the present invention are Irgacure 500, Irgacure 1000, Irgacure 2959, and Darocure 1173 (all ex Ciba) or Esacure KTO 46 and KIP EM (both ex Lamberti).
  • the photoinitiator can be added to the radiation curable resin, i.e. before the mixing of the dispersion comprising the cellulose ester and the radiation curable resin. It is also possible to add the photoinitiator after the mixing of the dispersion comprising the cellulose ester and the radiation curable resin.
  • Additives and fillers that are known to those skilled in the art can be added to the lacquer compositions according to the present invention, e.g., co-solvents, defoamers, levelling agents, antisettling agents, rheology modifiers, and pigments.
  • the lacquer compositions according to the present invention can be cured in a comparatively short time and at ambient temperature. Therefore, these coating compositions are in particular suited for industrial coating processes.
  • the compositions can be used to coat heat sensitive substrates, e.g., wooden or plastic substrates.
  • lacquer compositions of the present invention are very suited to be used as a clear coat on wooden substrates, e.g., as a clear coat on wooden furniture.
  • pbw stands for "parts by weight”.
  • EN 12720 European Standard
  • Several of the tests from EN 12720 are also used in the "M ⁇ belfakta” test.
  • “Mobelfakta” is a well-known and accepted test used for testing furniture coatings. The results of these tests are given on a 5-point scale, wherein 1 indicates “poor” and 5 indicates “excellent” performance.
  • An oil-in-water dispersion was prepared by mixing the following components:
  • Samples were prepared by mixing 100 pbw of the dispersion comprising nitrocellulose and the alkyd resin (NC/AR) with a dispersion comprising a radiation curable resin and optionally 2 pbw of a photoinitiator (Irgacure 500, ex Ciba).
  • a radiation curable resin e.g., nitrocellulose and the alkyd resin (NC/AR)
  • a dispersion comprising a radiation curable resin and optionally 2 pbw of a photoinitiator (Irgacure 500, ex Ciba).
  • a photoinitiator Irgacure 500, ex Ciba
  • lacquers from the thus obtained dispersions 100 parts of each dispersion were mixed at room temperature with 5 parts of a non-ionic wax dispersion, 0.7 parts of silica, 6.5 part of 3-Metoxi-n-butylacetat (or Butoxyl), 0.5 parts of additives , and 5 parts of water.
  • the lacquer samples were applied on wooden panels using an airmix spraygun. Two layers were applied at 70 g/m 2 . Water was evaporated at 50°C for 10 minutes. Then the panels were mounted on a drive belt and passed under a 80 W/cm 2 Hg Lamp at a speed of 5 m/min.
  • Example 1 was cured by using IR radiation only. It was noted that after evaporation of the water, the coated surfaces were not tacky.
  • 154 241 was prepared.
  • a solution was prepared comprising a polyesteracrylate resin (Roskydal 850 W ® ), cellulose nitrate Norm 27E, and n-butylacetate.
  • a dispersion was prepared by the slow addition of water under constant mixing.
  • a photoinitiator was added to the dispersion.
  • a lacquer was prepared from this dispersion in the same way as was done for the other samples. The lacquer was applied on a wooden panel and cured as described before. It was noted that after evaporation of the water, the coated surface was still tacky.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Wood Science & Technology (AREA)
  • Organic Chemistry (AREA)
  • Paints Or Removers (AREA)
EP00964073A 1999-08-30 2000-08-29 Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung Withdrawn EP1208169A1 (de)

Priority Applications (1)

Application Number Priority Date Filing Date Title
EP00964073A EP1208169A1 (de) 1999-08-30 2000-08-29 Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP99202786 1999-08-30
EP99202786 1999-08-30
PCT/EP2000/008492 WO2001016239A1 (en) 1999-08-30 2000-08-29 Waterborne radiation curable lacquers based on cellulose and their preparation
EP00964073A EP1208169A1 (de) 1999-08-30 2000-08-29 Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung

Publications (1)

Publication Number Publication Date
EP1208169A1 true EP1208169A1 (de) 2002-05-29

Family

ID=8240581

Family Applications (1)

Application Number Title Priority Date Filing Date
EP00964073A Withdrawn EP1208169A1 (de) 1999-08-30 2000-08-29 Wässrige, strahlungshärtbare lacke auf basis von zellulose, und deren herstellung

Country Status (3)

Country Link
EP (1) EP1208169A1 (de)
AU (1) AU7512500A (de)
WO (1) WO2001016239A1 (de)

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE102006000867A1 (de) 2006-01-05 2007-07-12 Marabuwerke Gmbh & Co. Kg UV-härtende Glasdruckfarbe und UV-härtender Glasdrucklack sowie Verfahren zum Bedrucken von Glassubstraten
CN102127362A (zh) * 2011-02-28 2011-07-20 上虞市佑谦特种材料有限公司 水性光固化弹性漆

Family Cites Families (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2436614A1 (de) * 1974-07-30 1976-02-19 Basf Farben & Fasern Verfahren zum herstellen von undurchsichtigen, deckenden ueberzuegen
US4134809A (en) * 1977-08-22 1979-01-16 Eastman Kodak Company Radiation curable cellulose ester-acrylate compositions
AU528378B2 (en) * 1978-09-13 1983-04-28 Rock, J.D. And Garnett, J.L. Radiation cured coating for leather
CA2024940A1 (en) * 1989-10-30 1991-05-01 Richard G. Brown Radiation-curable blend of a cellulose ester and a multifunctional (meth)acrylate
US5254603A (en) * 1990-12-24 1993-10-19 Hercules Incorporated Low toxicity radiation curable resins and coatings made therefrom
AU730163B2 (en) * 1996-11-06 2001-03-01 Rohm And Haas Company Method of curing coating compositions

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
See references of WO0116239A1 *

Also Published As

Publication number Publication date
AU7512500A (en) 2001-03-26
WO2001016239A1 (en) 2001-03-08

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