EP0202803A2 - Aushärten mit Laser von Beschichtungen und Tinten - Google Patents

Aushärten mit Laser von Beschichtungen und Tinten Download PDF

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Publication number
EP0202803A2
EP0202803A2 EP86303326A EP86303326A EP0202803A2 EP 0202803 A2 EP0202803 A2 EP 0202803A2 EP 86303326 A EP86303326 A EP 86303326A EP 86303326 A EP86303326 A EP 86303326A EP 0202803 A2 EP0202803 A2 EP 0202803A2
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EP
European Patent Office
Prior art keywords
coating
cure
photoinitiator
curing
single pulse
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Withdrawn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
EP86303326A
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English (en)
French (fr)
Other versions
EP0202803A3 (de
Inventor
Alfred M. Akerman
David I. Klick
Robert George Mayrick
George Lange Paul
Gavin Pierce Reid
Darko Supurovic
Haruki Tsuda
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.)
Commonwealth of Australia
Commonwealth of Australia Department of Industry and Commerce
Original Assignee
Commonwealth of Australia
Commonwealth of Australia Department of Industry and Commerce
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 Commonwealth of Australia, Commonwealth of Australia Department of Industry and Commerce filed Critical Commonwealth of Australia
Publication of EP0202803A2 publication Critical patent/EP0202803A2/de
Publication of EP0202803A3 publication Critical patent/EP0202803A3/de
Withdrawn legal-status Critical Current

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    • 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
    • B05D3/00—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials
    • B05D3/06—Pretreatment of surfaces to which liquids or other fluent materials are to be applied; After-treatment of applied coatings, e.g. intermediate treating of an applied coating preparatory to subsequent applications of liquids or other fluent materials by exposure to radiation
    • B—PERFORMING OPERATIONS; TRANSPORTING
    • B41—PRINTING; LINING MACHINES; TYPEWRITERS; STAMPS
    • B41M—PRINTING, DUPLICATING, MARKING, OR COPYING PROCESSES; COLOUR PRINTING
    • B41M7/00—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock
    • B41M7/0045—After-treatment of prints, e.g. heating, irradiating, setting of the ink, protection of the printed stock using protective coatings or film forming compositions cured by mechanical wave energy, e.g. ultrasonics, cured by electromagnetic radiation or waves, e.g. ultraviolet radiation, electron beams, or cured by magnetic or electric fields, e.g. electric discharge, plasma

Definitions

  • Ultraviolet coatings are typically composed of a liquid or solid polymer and/or oligomer and/or a monomer, and a photoinitiator.
  • a hydrogen donor such as amines or thiols and their analogues including polymeric analogues are optionally included with the photoinitiator to increase production of radicals used to start the polymer chains.
  • a photoinitiator molecule When a photoinitiator molecule absorbs a photon of light it can form a radical that combines with a monomer or polymer to start the growth of Long chain polymers thereby effecting a cure of the coating or ink.
  • Typical ultraviolet lamp based systems require a fluence of one Joule per square centimetre or greater to ensure cured coatings or films of practical thickness. While the expenditure of such energies leads to practical curing speeds, major advantages are to be gained if the fluence can be reduced so as to allow curing of more film with the same light energy resulting in increased output. Freedom to select the one best wavelength and wavelength bandwidth is also advantageous. Further, when making a thick coating, the surface often cures before the body of the coating, leading to a wrinkling of that coating and poor surface adhesion.
  • ovens are used to remove solvents and thus dry and/or polymerise conventional solvent or aqueous based coatings. Such ovens occupy considerable space and require relatively large amounts of energy to maintain their temperature as well as the provision of ventilation for the removal of solvent fumes. The desirability of a more even cure rate through the depth of the coating is readily apparent as are the benefits to be gained by reduced fluence to effect photo-polymerization.
  • UV lamps are used for clear coatings and inks, but ozone, heat removal and non-useful wavelengths of light can reduce their effectiveness. So little light from these lamps can penetrate a typical thick pigmented coating that they are not used commercially to any significant extent for this purpose.
  • the present invention consists in a method of curing a coating comprising applying said coating to a surface, said coating comprising a liquid or solid polymer and/or oligomer, and/or a monomer and at least one photoinitiator, and irradiating said coating with ultraviolet laser light of at least one predetermined wavelength, wherein the at least one predetermined wavelength is selected so as to be preferentially absorbed by the at least one photoinitiator rather than the other components of the coating.
  • the coating is in the form of a pigmented coating or ink
  • the coating further comprises a pigment and the at least one predetermined wavelength of said laser light is selected so as to be minimally absorbed by the pigment.
  • a particularly preferred method in accordance with the invention provides that the laser light is applied to the coating by being pulsed.
  • at least 25 pulses of the laser light are required to effect a cure.
  • at least 50 pulses are required to effect a cure.
  • the single pulse fluence of the applied laser light is kept low and preferably4 3mJ/cm 2 .
  • the total energy to effect a cure is very significantly reduced where the single pulse fluence is reduced and the total number of pulses applied to the coating or ink is increased while operating, at a predetermined pulse repetition rate.
  • pigmented coatings are of a thickness ⁇ 0.5 microns; clear coatings have a thickness ⁇ 2 microns; and printing inks have a thickness ⁇ 20 microns.
  • the laser source may be placed remote from the coating location since its light output is easily transmitted long distances. Techniques for expanding the beam and making it sufficiently uniform are readily apparent.
  • the present invention has been employed in the curing of commercial quality coatings of 20 microns and larger thicknesses with 50% of rutile Ti0 2 by weight.
  • laser light is used to achieve a through cure of the coating by penetrating the coating at a wavelength of minimum absorption due to the pigment.
  • a photoinitiator is used that absorbs light at this wavelength and whose concentration may be adjusted for maximum energy efficiency.
  • a nitrogen atmosphere is used to counteract oxygen inhibition during the curing process and very short pulses of light, typically of the order of 20-40 nonoseconds, are employed to initiate polymer growth in a particular area of the coating.
  • very short pulses of light typically of the order of 20-40 nonoseconds
  • the use of consecutive pulses of short duration promotes the cure to completion in combination with low fluence of light.
  • Typical UV laser curable coatings suitable for use in the present invention may be composed of but not limited to the following materials:-1.
  • Reactive Oligomer (s) A low molecular weight polymer (typically greater than 500 in weight average molecular weight) with one or more reactive functionalities to include unsaturated reaction sites, such as but not limited to acrylates or acrylamides or polyester, polyether, alkyd, cellulosics, acrylic, epoxy, silicone polyester, urethanes or any combination thereof.
  • a polyene/polythiol type system, or a system such as a cationic initiated type may also be employed.
  • Anionic initiated types may also be employed.
  • a typical photoinitiator system could preferably include two of the following family groups, as follows:
  • Typical UV curable coatings for use in the present invention may typically be composed of the materials recited above for clear coating but together with coloured pigments such as Ti0 2 .
  • the photoinitiator for titanium dioxide pigment systems typically being CTX/MDEOA, DETX/MDEOA, ITX/MDEOA, and RTX/MDEOA.
  • MDEOA may be replaced by Ethyl-p-dimethylaminobenzoate, EPB, and also p-dimethylaminoethylbenzoate.
  • DETX analogues and Acyl Phosphine oxide and analogues, related polymers and amines and aminobenzoates.
  • the photoinitiator concentration may be adjusted to minimise the laser energy per sq. cm at a given concentration of pigment which is required to completely cure the coating.
  • Lasers employed in the practice of the invention may typically have a band width of around 5 nanometers or less centred at the processing wavelength. There is a narrow optimum in wavelength for each combination of pigment and photoinitiator. Doubling the wavelength spread or shifting the wavelength 5 nanometres either side of optimum will increase the energy requirement.
  • acylphosphine oxide as the photoinitiator is particularly advantageous and its use results in a hard, well cured coating with good and pure white colour.
  • Wavelengths of UV laser between 400 and 450 nm have been successfully employed as rutile Ti0 2 does not absorb as strongly in that range.
  • other pigments with absorption at shorter wavelengths in the UV region of the spectrum or thinner coatings, such as inks, will require less energy/cm 2 to cure.
  • photoinitiators are preferred where they absorb at those wavelengths where the pigments used have least absorption.
  • Lasers which are typically suited in the operation of the present invention are rare gas halide (excimer) lasers which have achieved marked improvements in reliability and average power since their development in 1976.
  • Lasers of interest include such as are referenced in "Solvent Dependent Characteristics of XeCl Pumped UV Dye Lasers" by Cassard, Corkum and Alcock, Appl. Phys. 25,17-22 (1981).
  • the basic principle of laser curing of coatings and inks in accordance with the invention relies on the fact that laser light is substantially monochromatic, so that all the light can be employed to perform useful work.
  • the photoinitiator is chosen to have its maximum activity at the laser wavelength.
  • Fig. 1 the absorption curve of the photoinitiator trigonal 12 is plotted, with the line showing 100% of the laser light at 308 nm.
  • the mercury lamps that are currently used for curing clear coatings have many lines, only a few of which do useful work. For instance, in Fig. 1, emissions of wavelengths above 350 nm are poorly absorbed by the photoinitiator, and emissions below 270 nm do not penetrate the bulk of the coating. The remaining emissions around 300 nm comprise only 10% of the lamp's output light in the UV region.
  • Fig. 2 demonstrates that very thick (50 - 150 microns) clear coatings may be cured by the laser method. Total laser energy required to cure reaches an optimum for a given concentration of the photoinitiator, DETX.
  • coatings were illuminated by an expanded laser beam in a nitrogen atmosphere until an excellent (commercially acceptable) cure was obtained.
  • the graph of Fig. 3 shows that a lower fluence (a more expanded laser beam) leads to a lower energy requirement for cure.
  • the lowest fluence allowable is given by the largest practical area of illumination. This in turn determines the lowest possible total fluence and hence the fastest "belt speed" at which material may be cured.
  • the slope of these data is well explained by the theory of radical recombination.
  • Fig. 5 demonstrates that ultraviolet curing of coatings containing Ti0 2 (i.e. opaque paints) must be done at longer wavelength than the absorption edge of Ti0 2 (shown here at 400 to 410 nm). At shorter wavelength, the light is all absorbed before reaching the bottom of the coating.
  • the theoretical curing speed can be considered to be proportional to the intensity of light reaching the bottom of the coating.
  • the experimental curve of Fig. 6 for the energy to cure vs. wavelength shows a very sharp optimum for the photoinitiator DETX.
  • the illuminating wavelength should preferably be 422 + 5 nm.
  • the dye Popop can be made to lase at many wavelengths (see Fig. 8), including the optimum ones for D ETX and acylphosphine oxide (APO) pigmented coatings with Ti0 2 .
  • Fig. 9 demonstrates that the dye laser method is able to cure thick (up to 60 microns) pigmented coatings, with different loadings of Ti0 2 .
  • the optimum photoinitiator e.g., acylphosphine oxide, concentration changes with illumination intensity as shown in the plot of Fig. 12. Fortunately, low fluence is associated with both faster cure speeds and lower photoinitiator concentration, which means lower costs.
  • Inks employed in these examples carry the trade name "Viodri” as marketed by Coates Brothers Australia Pty. Ltd., their exact composition is unknown.
  • Coates literature says they contain polyfunctional acrylate esters and photoinitiators such as benzophenone.
  • Clear varnishes in these examples consisted of epoxy acrylate and HDDA (hexanedioldiacrylate) in a 60/40 ratio.
  • a photoinitiator at a .5-3% level, along with an amine (N-methyldiethanol amine) in the same concentration as the photoinitiator.
  • Coatings were spread onto paperboard with a wire-wound bar for less than 50 micron thickness, or between layers of tape for the 150 micron thickness. Coatings were cured under a nitrogen atmosphere with low fluence illumination directly from an excimer laser operating at 308 nm (Lambda Physik EMG 203) or 351 nm (Lambda Physik 150 ETS).
  • a scratch test was used to determine a successful cure, and the minimum total energy to cure was noted.
  • Photoinitiator - acylphosphine oxide at concentration 3% Thickness - 60 microns. Pigment loading - 32% Ti0 2 by weight.
  • a typical mix of ingredients for a clear coating in accordance with the invention comprises the following by weight: 56.4% epoxy acrylate oligomer (51-650 of A.C. Hatrick Chemicals Pty. Limited (A.C.H.)); 37.6% H.D.O.D.A. hexane diol diacrylate (A.C.H.); 3% Trigonal 12 phenyl benzophenone (AKZO Chemicals); and 3% MDEOA methyl diethanol amine (Union Carbide) .
  • This mixture was applied wet to a thickness of 7 m by draw down bars and was cured under a nitrogen blanket with a single pulse fluence of 0.0065 millijoules/cm 2 .
  • the total energy required to cure was 0.9 mJ/cm 2 and the state of cure was assessed by measuring hardness of the coating via a scratch test.
  • the substrate to which the coating was applied was high quality low porosity white paper.
  • the wet sample coating having dimensions of 10cm x 5cm was irradiated by a laser beam of dimensions l5cm x 15cm.
  • the results of this static test when extrapolated to a dynamic environment equate to a belt travelling at 667 metres/min, the belt being 1 metre wide and the illuminated area being 1 x 3m 2 .
  • This example also concerns a clear coating formed from the following ingredients in percentages of the total mixture by weight: 56.4% Celrad 3700 epoxy acrylate oligomer (Celanese Corporation); 37.6% HDODA (A.C.H.); 3% Trigonal 12 (AKZO Chemicals); and 3% MDEOA (Union Carbide).
  • the wet coating was applied to a thickness of 5 ⁇ m with a draw down bar and the same substrate was employed as for Example I but the single pulse fluence applied was 0.00015 millijoules/cm 2 and the total energy to cure was 0.29 mJ/cm 2 .
  • the equivalent belt speed in this case is 2069 m/min for the same area of illumination as in Example I.
  • a pigmented coating was produced by curing a mixture of the following ingredients combined in weight percentages as follows: 61% of a 60/40 mixture of epoxy acrylate oligomer (ACH 51-650) and H.D.O.D.A. (A.C.H.); 32% TiO 2 RHD 2 (I.C.I); 3% Trigcnal 12; and 4% acyl phosphene oxide (BASF).
  • the equivalent belt speed in this case using an illuminated area of 1 x 3m 2 is 50 m/min.

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  • Physics & Mathematics (AREA)
  • Engineering & Computer Science (AREA)
  • Plasma & Fusion (AREA)
  • Electromagnetism (AREA)
  • Mechanical Engineering (AREA)
  • Application Of Or Painting With Fluid Materials (AREA)
  • Paints Or Removers (AREA)
EP86303326A 1985-05-14 1986-05-01 Aushärten mit Laser von Beschichtungen und Tinten Withdrawn EP0202803A3 (de)

Applications Claiming Priority (3)

Application Number Priority Date Filing Date Title
AU541/85 1985-05-14
AUPH054185 1985-05-14
AU56822/86A AU581981B2 (en) 1985-05-14 1986-05-14 Laser curing of coatings and inks

Publications (2)

Publication Number Publication Date
EP0202803A2 true EP0202803A2 (de) 1986-11-26
EP0202803A3 EP0202803A3 (de) 1987-06-03

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EP86303326A Withdrawn EP0202803A3 (de) 1985-05-14 1986-05-01 Aushärten mit Laser von Beschichtungen und Tinten

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AU (1) AU581981B2 (de)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353583A2 (de) * 1988-08-05 1990-02-07 Siemens Aktiengesellschaft Verfahren zur Erzeugung dünner Schichten auf Siliconbasis
EP0402546A2 (de) * 1989-06-14 1990-12-19 Poly-Flex Circuits, Inc. Gedruckte Schaltungsplatte
EP0426904A1 (de) * 1989-11-06 1991-05-15 Dunfries Investments Limited Verfahren zum Aufbringen einer Beschichtung auf eine Unterlage
EP0440178A1 (de) * 1990-01-31 1991-08-07 Herberts Gesellschaft mit beschränkter Haftung Verfahren zum Beschichten von Substraten mit durch UV-Strahlung härtbaren Überzugsmitteln
EP0447169A1 (de) * 1990-03-13 1991-09-18 BAUSCH & LOMB INCORPORATED Laser-Aushärten von Kontaktlinsen
DE4230149A1 (de) * 1992-09-09 1994-03-17 Heraeus Noblelight Gmbh Verfahren zur Herstellung von oxydischen Schutzschichten
DE19649301A1 (de) * 1996-11-28 1998-06-04 Orga Kartensysteme Gmbh Verfahren zum Aufbringen von Markierungen, Beschriftungen und/oder Strukturierungen auf die Oberfläche einer Ausweiskarte o. dgl.
WO1999026732A1 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
WO1999026733A1 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
WO1999026728A2 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
US6078713A (en) * 1998-06-08 2000-06-20 Uv Technology, Inc. Beam delivery system for curing of photo initiated inks
WO2000050245A1 (en) * 1999-02-25 2000-08-31 Kimberly-Clark Worldwide, Inc. Printing apparatus
WO2000061301A1 (en) * 1999-04-09 2000-10-19 Tec-Masters, Inc. Encoding symbologies and graphics on nonporous materials
WO2001098223A1 (en) * 2000-06-16 2001-12-27 Alcatel Uv-cure of coatings for an optical fiber with a laser
US7022382B1 (en) * 2000-06-16 2006-04-04 Alcatel UV-cure of coatings for an optical fiber with a laser
US7522281B2 (en) * 2004-12-20 2009-04-21 Heidelberger Druckmaschinen Ag Apparatus and method for detecting moisture in a printing plate exposer
WO2020234576A1 (en) * 2019-05-17 2020-11-26 The University Of Birmingham Tunable materials

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US6524379B2 (en) 1997-08-15 2003-02-25 Kimberly-Clark Worldwide, Inc. Colorants, colorant stabilizers, ink compositions, and improved methods of making the same
EP1144512B1 (de) 1999-01-19 2003-04-23 Kimberly-Clark Worldwide, Inc. Farbstoffe, farbstoffstabilisatoren, tintenzusammensetzungen und verfahren zu deren herstellung
US6368395B1 (en) 1999-05-24 2002-04-09 Kimberly-Clark Worldwide, Inc. Subphthalocyanine colorants, ink compositions, and method of making the same

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2447790A1 (de) * 1974-10-07 1976-04-08 Scm Corp Ultraviolett- und laserhaertung polymerisierbarer bindemittel

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3847771A (en) * 1973-03-30 1974-11-12 Scm Corp Uv and laser curing of pigmented polymerizable binders

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE2447790A1 (de) * 1974-10-07 1976-04-08 Scm Corp Ultraviolett- und laserhaertung polymerisierbarer bindemittel

Cited By (24)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0353583A3 (en) * 1988-08-05 1990-03-07 Siemens Aktiengesellschaft Method for making thin silicone coatings
US4983419A (en) * 1988-08-05 1991-01-08 Siemens Aktiengesellschaft Method for generating thin layers on a silicone base
EP0353583A2 (de) * 1988-08-05 1990-02-07 Siemens Aktiengesellschaft Verfahren zur Erzeugung dünner Schichten auf Siliconbasis
EP0402546A3 (de) * 1989-06-14 1991-12-18 Poly-Flex Circuits, Inc. Gedruckte Schaltungsplatte
EP0402546A2 (de) * 1989-06-14 1990-12-19 Poly-Flex Circuits, Inc. Gedruckte Schaltungsplatte
EP0426904A1 (de) * 1989-11-06 1991-05-15 Dunfries Investments Limited Verfahren zum Aufbringen einer Beschichtung auf eine Unterlage
EP0440178A1 (de) * 1990-01-31 1991-08-07 Herberts Gesellschaft mit beschränkter Haftung Verfahren zum Beschichten von Substraten mit durch UV-Strahlung härtbaren Überzugsmitteln
EP0447169A1 (de) * 1990-03-13 1991-09-18 BAUSCH & LOMB INCORPORATED Laser-Aushärten von Kontaktlinsen
US5154861A (en) * 1990-03-13 1992-10-13 Bausch & Lomb Incorporated Laser curing of contact lens
DE4230149A1 (de) * 1992-09-09 1994-03-17 Heraeus Noblelight Gmbh Verfahren zur Herstellung von oxydischen Schutzschichten
DE19649301A1 (de) * 1996-11-28 1998-06-04 Orga Kartensysteme Gmbh Verfahren zum Aufbringen von Markierungen, Beschriftungen und/oder Strukturierungen auf die Oberfläche einer Ausweiskarte o. dgl.
DE19649301C2 (de) * 1996-11-28 1998-12-10 Orga Kartensysteme Gmbh Verfahren zum Aufbringen von Markierungen, Beschriftungen und Strukturierungen auf die Oberfläche einer Ausweiskarte oder einer anderen Karte
US6165696A (en) * 1996-11-28 2000-12-26 Orga Kartensysteme Gmbh Process for applying marks letterings and structures on the surface of an identity card or a different card
WO1999026732A1 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
WO1999026728A2 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
WO1999026728A3 (de) * 1997-11-20 1999-07-15 Herberts & Co Gmbh Verfahren zur mehrschichtigen lackierung von substraten
WO1999026733A1 (de) * 1997-11-20 1999-06-03 E.I. Du Pont De Nemours And Company, Inc. Verfahren zur mehrschichtigen lackierung von substraten
US6078713A (en) * 1998-06-08 2000-06-20 Uv Technology, Inc. Beam delivery system for curing of photo initiated inks
WO2000050245A1 (en) * 1999-02-25 2000-08-31 Kimberly-Clark Worldwide, Inc. Printing apparatus
WO2000061301A1 (en) * 1999-04-09 2000-10-19 Tec-Masters, Inc. Encoding symbologies and graphics on nonporous materials
WO2001098223A1 (en) * 2000-06-16 2001-12-27 Alcatel Uv-cure of coatings for an optical fiber with a laser
US7022382B1 (en) * 2000-06-16 2006-04-04 Alcatel UV-cure of coatings for an optical fiber with a laser
US7522281B2 (en) * 2004-12-20 2009-04-21 Heidelberger Druckmaschinen Ag Apparatus and method for detecting moisture in a printing plate exposer
WO2020234576A1 (en) * 2019-05-17 2020-11-26 The University Of Birmingham Tunable materials

Also Published As

Publication number Publication date
AU5682286A (en) 1986-11-20
AU581981B2 (en) 1989-03-09
EP0202803A3 (de) 1987-06-03

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