GB2166755A - Polymeric liquid crystalline materials - Google Patents

Polymeric liquid crystalline materials Download PDF

Info

Publication number
GB2166755A
GB2166755A GB08527316A GB8527316A GB2166755A GB 2166755 A GB2166755 A GB 2166755A GB 08527316 A GB08527316 A GB 08527316A GB 8527316 A GB8527316 A GB 8527316A GB 2166755 A GB2166755 A GB 2166755A
Authority
GB
United Kingdom
Prior art keywords
coating
regions
selectively
polymerized
optical response
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Withdrawn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
GB08527316A
Other versions
GB8527316D0 (en
Inventor
Lynn Marie Reslewic
James Arthur Tshudy
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.)
Armstrong World Industries Inc
Original Assignee
Armstrong World Industries Inc
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 Armstrong World Industries Inc filed Critical Armstrong World Industries Inc
Publication of GB8527316D0 publication Critical patent/GB8527316D0/en
Publication of GB2166755A publication Critical patent/GB2166755A/en
Withdrawn legal-status Critical Current

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/36—Steroidal liquid crystal compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/38—Polymers
    • C09K19/3833—Polymers with mesogenic groups in the side chain
    • C09K19/3842—Polyvinyl derivatives
    • C09K19/3852—Poly(meth)acrylate derivatives
    • C09K19/3866—Poly(meth)acrylate derivatives containing steroid groups
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters
    • G02F1/133516—Methods for their manufacture, e.g. printing, electro-deposition or photolithography
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133528—Polarisers
    • G02F1/133543—Cholesteric polarisers

Landscapes

  • Chemical & Material Sciences (AREA)
  • Crystallography & Structural Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Organic Chemistry (AREA)
  • Heating, Cooling, Or Curing Plastics Or The Like In General (AREA)
  • Paints Or Removers (AREA)
  • Polymerisation Methods In General (AREA)
  • Photosensitive Polymer And Photoresist Processing (AREA)
  • Liquid Crystal Substances (AREA)
  • Silver Salt Photography Or Processing Solution Therefor (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

Abstract

Polymeric liquid crystalline coatings which display differential fixed optical responses are obtained by selectively permitting certain regions of a cholesteric liquid crystalline monomer coating to photopolymerize at different rates than other regions of the coating.

Description

SPECIFICATION Polymeric liquid crystalline materials The present invention relates to polymeric liquid crystalline coatings and, more particularly, to polymeric liquid crystalline coatings which exhibit different optical responses in different regions of the coating.
Investigations of liquid crystalline materials have been increasingly reported in the literature in recent years. Many uses have been found for these materials, particularly as optical displays. Recently, articles have appeared in the scientific literature concerning cholesteric liquid crystalline materials which comprise polymerizable moieties. A number of articles have appeared in the Russian literature which describe solution-polymerized cholesterol derivatives possessing liquid crystalline properties. Of particular interest is the recent discovery that cholesteric liquid crystalline materials possessing defined optical properties may have those properties essentially fixed through a photopolymerization process to yield coatings whose optical responses are essentially temperature insensitive.
British Patent Application No. 8 333 323, Serial No. 2 133 406, describes certain cholesterol derivatives which possess acrylate moieties in the side chain at the 3-position. Compositions comprising these materials have been found to display optical properties varying from the infra-red to the ultraviolet portions of the spectrum wherein the optical properties are fixed through photopolymerization. In addition, coatings comprising more than one optical response have been described in British Patent Application No. 8 333 324, Serial No. 2 132 623. This application describes a process wherein the temperature is adjusted such that a desirable optical response is obtained and the coating is then selectively masked such that various regions of the coating are shielded from a first photopolymerizing radiation exposure.The first photopolymerization step essentially fixes the optical response in the areas receiving the radiation, but leaves the masked areas uncured whereby, upon adjusting the temperature, the non-polymerized regions display a different optical response. Upon reirradiating the structure, a coating is provided wherein a multiple optical response is obtained in different regions of the coating. The term "optical response" and related terms used herein have the meanings set forth in the above-mentioned application.
Although such coatings display unique properties, it is not always desirable to acquire multiple optical displays through the adjustment of temperature. Accordingly, one object of the present invention is to provide a photopolymerized liquid crystalline coating having multiple optical responses without the need to adjust the temperature, although the invention does not exclude the possibility of temperature changes in addition to the procedures described herein.
Another objective of the present invention is to provide a coating which provides multiple optical responses wherein the coating also exhibits a three-dimensional optical response.
The present invention provides a polymeric cholesteric liquid crystalline coating which displays multiple optical responses obtained without varying the temperature during the photopolymerization process.
By selectively permitting a certain region or regions of the coating to photopolymerize at different rates than another region or other regions of the coating, a coating may be obtained which demonstrates a differential fixed optical response.
In one embodiment, the present invention provides a method of preparing a polymeric coating having a fixed optical response, said method comprising the steps of providing a coating comprising a photopolymerizable cholesteric liquid crystalline monomeric material; selectively aligning at least a portion of said coating such that said aligned portion demonstrates an optical response; and sequentially exposing said coating to photopolymerizing radiation under conditions such that selected regions of said coating are polymerized at different rates than are other regions of said coating, whereby the cured coating demonstrates differential fixed optical responses.
In a second embodiment, the present invention relates to a photopolymerized cholesteric liquid crystalline coating having a'differential fixed optical response, said coating being obtained from the sequential exposure of said coating to photopolymerizing radiation under conditions such that selected regions of said coating are polymerized at different rates than are other regions of said coating.
The monomers which may be used to practice the present invention are those cholesteric liquid crystalline materials which possess a photopolymerizable side chain and which exhibit a desired optical response, preferably within the visible spectrum. The preferred monomers are those which are disclosed in the aforementioned pending Application Serial No. 2 133 406; however, it must be kept in mind that these materials may be used as single monomers, mixtures of monomers, or mixtures comprising monomers and other polymerizable or non-polymerizable non-mesogenic materials.
In order to carry out the present invention, a composition is prepared comprising a photopolymerizable cholesteric liquid crystalline monomer and a photo-initiator, and, optionally, other monomeric mesogenic or non-mesogenic materials and/or non-mesogenic, non-polymerizable diluents. The material is then prepared as a coating or film and subjected to a temperature such that the coating or film exhibits a desired optical response. The material will then be photopolymerized such that selected regions of the film cure at different rates than other regions of the film. This may be accomplished in a variety of ways.
As one example, the polymerization of the surface may be performed in the presence of oxygen which will tend to inhibit the photopolymerization reaction. If a negative or other mask which selectively masks the coating from the polymerizing radiation is placed over the coating or film, no curing will occur under the masked area, but it will occur in the areas where the mask does not shield the coating from the radiation. Nevertheless, in the exposed areas, the surface region will be incompletely cured because of oxygen inhibition whereas the internal regions in those areas will be fully cured. If the mask is then removed and the surface is thoroughly flushed with nitrogen or other inert gas, an optical response difference will be noted over the surface of the coating.Those previously masked areas will exhibit one optical response whereas the unmasked and oxygen-inhibited areas will show a different color.
As another alternative, the surface may be partially masked and then subjected to photopolymerizing radiation under an inert atmosphere, thereby resulting in a complete cure in the unmasked areas. If the mask is then removed and a mixture of nitrogen and oxygen is permitted adjacent the surface which remains uncured, exposure of this surface to the photopolymerizing radiation results in a different cure rate. After final curing in an inert atmosphere, a noticeable color differential is observed between the initially and subsequently cured regions.
Three dimensional effects may also be created by using two different masks in combination with the above procedures. For example, a first mask may be placed over a film which is then irradiated in air.
The mask is then removed and the entire film surface is irradiated in air. A second mask is placed over the film and irradiated under an inert atmosphere, and this mask is then removed and the entire film is irradiated under an inert atmosphere. The result is a film which exhibits three-dimensional images.
Different cure rates may also be effected by using a totally inert atmosphere but by subjecting one portion of the surface to high strength radiant energy and other regions of the surface to lower-strength radiant energy. Because different photopolymerization rates are achieved in these different areas, different optical responses are shown in different regions in the resulting product.
The following examples illustrate the invention.
Examples In the following examples, compounds corresponding to acrylate derivatives Va and Ve as described in British Specification No. 2 133 406 were used to prepare the monomeric films. These compounds have the structure
For compound Va, n = 10 and for compound Ve, n = 3.
Example 1 A composition was prepared comprising 47 weight percent each of compounds Va and Ve, 3% of pentaerythritol triacrylate cross-linking agent, 2% benzophenone photoinitiator and 1% IrgacureG' 651 photoinitiator. Irgacure 651 is 2,2-dimethoxy-2-phenyl acetophenone.
The composition was completely melted at 200"F (93"C), allowed to cool to room temperature, and a 0.002-inch (0.051 mum) draw down was made at room temperature on a Molars polyester film. The nonpolymerized material appeared blue-green at a 90-degree (specular) viewing angle.
The draw down was placed in a chamber, covered with a negative which selectively shielded portions of the surface, and the chamber was partially flushed with nitrogen, leaving some residual oxygen. The masked coating was then subjected to 150 joules (per square centimeter of coating) of UV energy (i.e., 5 wafts/cm2 for 30 seconds) to produce an image which in the exposed areas was yellow-green at a specular viewing angle. The chamber was then opened, the mask was removed, and the chamber was reclosed and completely flushed with nitrogen to eliminate all oxygen. The entire film was subsequently exposed to 300 joules of energy (i.e., 5 watts/cm2 for 60 seconds) to polymerize the film completely. The polymerized film contained a yellow/green image with a blue-green background when viewed at a specular angle.
Example 2 A composition was prepared comprising 48.25 weight percent of each of compounds Va and Ve, 3% pentaerythritol triacrylate, and 0.5% Irgacure 651, and a film was prepared as described in Example 1; it also gave a blue-green appearance. The film was covered with a negative which selectively protected certain areas of the film and the masked film was then exposed to 150 joules of radiant energy (i.e., 5 watts/cm2 for 30 seconds) to produce a partially cured film which had a yellow-green appearance in the exposed regions.
The negative was removed from the film and the entire film was exposed in air to 50 joules of radiant energy (5 wattslcm2 for 10 seconds). Following the second exposure, the film was provided with a second negative selectively shielding different regions of the film and the film was placed in a chamber which was then completely flushed with nitrogen. The film was exposed to 150 joules of radiant energy (i.e., 5 watts/cm2 for 30 seconds) to produce an image which, in the most recently exposed areas, was blue-green at a specular viewing angle.
The second negative was removed and the entire film was exposed to 300 joules of radiant energy (i.e., 5 watts/cm2 for 60 seconds) in a completely flushed nitrogen chamber to polymerize the film completely. The resulting film contained two images. At a 90-degree viewing angle, the first image appeared to be on top of the second image; i.e., it had a three-dimensional effect. At a 45-degree viewing angle, the second image appeared to be on the top of the first image. In both instances, the first image appeared as light yellow-green, the second image appeared as blue-green, and the background appeared as dark yellow-green.

Claims (14)

1. A method of preparing a polymeric coating having a fixed optical response, said method comprising the steps of providing a coating comprising a photopolymerizable cholesteric liquid crystalline monomeric material, selectively aligning at least a portion of said coating such that said aligned portion demonstrates an optical response, and sequentially exposing said coating to photopolymerizing radiation under conditions such that selected regions of said coating are polymerized at different rates are other regions of said coating, whereby different regions of the cured coating demonstrate different fixed optical responses.
2. A method as claimed in Claim 1 hereof wherein said process comprises the steps of sequentially exposing said coating to photopolymerizing radiation while selectively masking portions of said coating from said radiation, said exposures being performed at substantially constant temperatures while selectively varying the oxygen content of the atmosphere adjacent the surface of said coating.
3. A method as claimed in Claim 2 hereof wherein said sequence comprises, (a) providing said coating with a first mask and irradiating said masked coating in an atmosphere which comprises oxygen, (b) removing said first mask and irradiating said coating in an atmosphere which comprises oxygen, (c) providing said coating with a second mask and irradiating said masked coating in an inert atmosphere, and (d) removing said second mask and irradiating said coating in an inert atmosphere.
4. A method as claimed in Claim 1 hereof wherein said coating is selectively exposed to photopolymerizing radiation of varying intensity.
5. A photopolymerized cholesteric liquid crystalline coating having a differential fixed optical response, said coating being obtained from the sequential exposure of said coating to photopolymerizing radiation under conditions such that selected regions of said coating were polymerized at different rates than were other regions of said coating.
6. A coating as claimed in Claim 5 hereof wherein said coating was sequentially exposed to photopolymerizing radiation while selectively masking portions of said film from said radiation, said exposures having been performed at substantially constant temperature while selectively varying the oxygen content of the atmosphere adjacent the surface of said material.
7. A coating as claimed in Claim 6 hereof wherein said coating comprises a three-dimensional image.
8. A coating as claimed in Claim 5 hereof wherein said coating was obtained by selectively exposing said material to photopolymerizing radiation of varying intensity.
9. A method of preparing a polymeric layer having a fixed optical response which comprises providing a layer exhibiting an optical response and comprising a photopolymerizable cholesteric liquid crystalline monomer, and exposing the layer to photopolymerizing radiation under conditions such that a selected region or regions of the coating is or are polymerized at a rate different from that at which another region is or other regions are polymerized, whereby the different regions of the polymerized coating exhibit different fixed optical responses.
10. A method as claimed in Claim 9, wherein the selected region(s) is or are polymerized before or after the other region(s).
11. A method as claimed in Claim 8 or Claim 9, wherein all steps of the polymerization are carried out at the same ambient temperature.
12. A method of preparing a polymeric layer having a fixed optical response carried out substantially as described in either of the Examples herein.
13. A photopolymerized layer whenever made by a method as claimed in any one of Claims 9 to 12.
14. Any new features hereinbefore described or any new combination of hereinbefore described features.
GB08527316A 1984-11-07 1985-11-06 Polymeric liquid crystalline materials Withdrawn GB2166755A (en)

Applications Claiming Priority (1)

Application Number Priority Date Filing Date Title
US66898284A 1984-11-07 1984-11-07

Publications (2)

Publication Number Publication Date
GB8527316D0 GB8527316D0 (en) 1985-12-11
GB2166755A true GB2166755A (en) 1986-05-14

Family

ID=24684544

Family Applications (1)

Application Number Title Priority Date Filing Date
GB08527316A Withdrawn GB2166755A (en) 1984-11-07 1985-11-06 Polymeric liquid crystalline materials

Country Status (7)

Country Link
JP (1) JPS61115989A (en)
BE (1) BE903585A (en)
DE (1) DE3535547A1 (en)
FR (1) FR2572813A1 (en)
GB (1) GB2166755A (en)
LU (1) LU86151A1 (en)
NL (1) NL8502932A (en)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0331233A3 (en) * 1988-02-29 1991-10-30 Koninklijke Philips Electronics N.V. Method of manufacturing a laminated element and the element thus obtained
US5629055A (en) * 1994-02-14 1997-05-13 Pulp And Paper Research Institute Of Canada Solidified liquid crystals of cellulose with optically variable properties
US5766679A (en) * 1995-02-15 1998-06-16 Basf Aktiengesellschaft Chiral nematic polyesters
GB2321717A (en) * 1997-01-31 1998-08-05 Sharp Kk Cholesteric optical filters
US6291629B1 (en) 1997-02-06 2001-09-18 Basf Aktiengesellschaft Chirally nematic polyesters
US6335462B1 (en) 1996-11-27 2002-01-01 Basf Aktiengesellschaft Polymerizable oligomesogenes
US6597426B1 (en) 1996-10-01 2003-07-22 Basf Aktiengesellschaft Flat element with a cholesteric liquid crystal structure
EP1245970A3 (en) * 2001-03-28 2004-01-28 Dai Nippon Printing Co., Ltd. Circular polarization controlling optical element and method of producing the same
FR2928265A1 (en) * 2008-03-04 2009-09-11 Oreal Treating human keratin materials e.g. hair, comprises applying composition having polymerizable liquid crystal of which color varies with temperature before its polymerization, on material and enhancing in situ liquid crystal polymerization
US8985463B2 (en) 2007-10-09 2015-03-24 Sicpa Holding Sa Security marking authentication device

Families Citing this family (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JP2635613B2 (en) * 1987-09-16 1997-07-30 株式会社東芝 Method of forming resist pattern
JPH0362337A (en) * 1989-07-29 1991-03-18 Canon Inc Information storage medium and its production
DE4408171A1 (en) * 1994-03-11 1995-09-14 Basf Ag New polymerizable liquid crystalline compounds
DE4441651A1 (en) * 1994-11-23 1996-04-25 Basf Ag Polymerisable material for coating and printing substrates
DE4442614A1 (en) * 1994-11-30 1996-06-05 Basf Ag Chiral connections
US5658270A (en) * 1995-04-24 1997-08-19 Mcneil-Ppc, Inc. Body adhering sanitary protection products
DE19745647A1 (en) 1997-10-15 1999-04-22 Basf Ag Heat insulation covering for e.g. insulation and in automobile sector
JP2003149439A (en) * 2001-11-12 2003-05-21 Dainippon Printing Co Ltd Method for manufacturing optical element which controls circularly polarized light

Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2132623A (en) * 1982-12-15 1984-07-11 Armstrong World Ind Inc Polymeric liquid crystal films

Family Cites Families (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPS52131961A (en) * 1976-04-28 1977-11-05 Hitachi Ltd Method of fabricating curved surface bending molds
DE3205892A1 (en) * 1982-02-18 1983-08-25 Bayer Ag, 5090 Leverkusen METHOD FOR ADJUSTING THE TEMPERATURE SENSITIVITY OF CHOLESTERINIC LIQUID CRYSTALS
CA1255653A (en) * 1982-12-15 1989-06-13 Paul J. Shannon Liquid crystalline materials useful to prepare polymeric films

Patent Citations (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
GB2132623A (en) * 1982-12-15 1984-07-11 Armstrong World Ind Inc Polymeric liquid crystal films

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0331233A3 (en) * 1988-02-29 1991-10-30 Koninklijke Philips Electronics N.V. Method of manufacturing a laminated element and the element thus obtained
US5629055A (en) * 1994-02-14 1997-05-13 Pulp And Paper Research Institute Of Canada Solidified liquid crystals of cellulose with optically variable properties
US5766679A (en) * 1995-02-15 1998-06-16 Basf Aktiengesellschaft Chiral nematic polyesters
US6597426B1 (en) 1996-10-01 2003-07-22 Basf Aktiengesellschaft Flat element with a cholesteric liquid crystal structure
US6335462B1 (en) 1996-11-27 2002-01-01 Basf Aktiengesellschaft Polymerizable oligomesogenes
US6339464B1 (en) 1997-01-31 2002-01-15 Sharp Kabushiki Kaisha Filter and method of making an optical device
GB2321717A (en) * 1997-01-31 1998-08-05 Sharp Kk Cholesteric optical filters
US6624872B2 (en) 1997-01-31 2003-09-23 Sharp Kabushiki Kaisha Optical radiation filter
US6291629B1 (en) 1997-02-06 2001-09-18 Basf Aktiengesellschaft Chirally nematic polyesters
EP1245970A3 (en) * 2001-03-28 2004-01-28 Dai Nippon Printing Co., Ltd. Circular polarization controlling optical element and method of producing the same
US6816215B2 (en) 2001-03-28 2004-11-09 Dai Nippon Printing Co., Ltd. Circular polarization controlling optical element and method of producing the same
EP1734386A2 (en) * 2001-03-28 2006-12-20 Dainippon Printing Co., Ltd. Circular polarization controlling optical element and method of producing the same
EP1734386A3 (en) * 2001-03-28 2007-01-03 Dainippon Printing Co., Ltd. Circular polarization controlling optical element and method of producing the same
US8985463B2 (en) 2007-10-09 2015-03-24 Sicpa Holding Sa Security marking authentication device
FR2928265A1 (en) * 2008-03-04 2009-09-11 Oreal Treating human keratin materials e.g. hair, comprises applying composition having polymerizable liquid crystal of which color varies with temperature before its polymerization, on material and enhancing in situ liquid crystal polymerization

Also Published As

Publication number Publication date
NL8502932A (en) 1986-06-02
JPS61115989A (en) 1986-06-03
LU86151A1 (en) 1986-03-24
GB8527316D0 (en) 1985-12-11
BE903585A (en) 1986-05-05
DE3535547A1 (en) 1986-05-07
FR2572813A1 (en) 1986-05-09

Similar Documents

Publication Publication Date Title
GB2166755A (en) Polymeric liquid crystalline materials
DE69412888T2 (en) Polymerization process
CA1216817A (en) Multiple step uv curing process for providing accurately controlled surface texture
JPH03160001A (en) Preparation of photopolymerizable composition
AU607318B2 (en) Process for preparing photocured coatings
TW262537B (en)
JPH0341234B2 (en)
KR0163588B1 (en) Photoresist mixture and use thereof
DE2512642C3 (en) Composition curable by actinic radiation
EP1307524B1 (en) Method of manufacturing a photochromic molded article
US3827957A (en) Photopolymerizable pigmented vehicles containing chlorosulfonated or alpha-haloalkylated polynuclear ketone initiators
DE69501986T2 (en) Flexographic printing plates made of photo-curable elastomer compositions
US5730911A (en) Process for the manufacture of a substrate made of transparent organic glass and substrate thus obtained
JPH04345608A (en) Material for color filter and its cured product
CH542888A (en) Radiation-curable compositions
KR20060105642A (en) Manufacturing method for transparent film
AU642211B2 (en) UV curable coating compositions, abrasion resistant UV stabilized thermoplastic composites and method
JPH03114711A (en) Casting method for synthetic resin
JPH10500782A (en) New ethylenically unsaturated monomers
JPH10292005A (en) Production of liquid crystal cured product
JP4600631B2 (en) Method for producing laminate including active energy ray-curable resin layer
US3827956A (en) Photopolymerizable pigmented vehicles containing chlorosulfonated or alpha-haloalkylated benzanthrone initiators
JPS5930171B2 (en) Manufacturing method of painted acrylic resin products
JPS60221755A (en) Method for dyeing surface film of base
JP3073816B2 (en) UV curable paint

Legal Events

Date Code Title Description
WAP Application withdrawn, taken to be withdrawn or refused ** after publication under section 16(1)