WO2008020829A2 - Extruded photochromic film on glass - Google Patents

Extruded photochromic film on glass Download PDF

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Publication number
WO2008020829A2
WO2008020829A2 PCT/US2006/031087 US2006031087W WO2008020829A2 WO 2008020829 A2 WO2008020829 A2 WO 2008020829A2 US 2006031087 W US2006031087 W US 2006031087W WO 2008020829 A2 WO2008020829 A2 WO 2008020829A2
Authority
WO
WIPO (PCT)
Prior art keywords
layer
laminate
adhesive
clear resin
resin layer
Prior art date
Application number
PCT/US2006/031087
Other languages
French (fr)
Other versions
WO2008020829A3 (en
Inventor
Ronald C. Wiand
Original Assignee
Softlight, 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 Softlight, Inc. filed Critical Softlight, Inc.
Priority to PCT/US2006/031087 priority Critical patent/WO2008020829A2/en
Publication of WO2008020829A2 publication Critical patent/WO2008020829A2/en
Publication of WO2008020829A3 publication Critical patent/WO2008020829A3/en

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10009Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets
    • B32B17/10018Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the number, the constitution or treatment of glass sheets comprising only one glass sheet
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/10165Functional features of the laminated safety glass or glazing
    • B32B17/10431Specific parts for the modulation of light incorporated into the laminated safety glass or glazing
    • B32B17/10467Variable transmission
    • B32B17/10486Variable transmission photochromic
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B17/00Layered products essentially comprising sheet glass, or glass, slag, or like fibres
    • B32B17/06Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material
    • B32B17/10Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin
    • B32B17/10005Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing
    • B32B17/1055Layered products essentially comprising sheet glass, or glass, slag, or like fibres comprising glass as the main or only constituent of a layer, next to another layer of a specific material of synthetic resin laminated safety glass or glazing characterized by the resin layer, i.e. interlayer
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2323/00Polyalkenes
    • B32B2323/04Polyethylene
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2367/00Polyesters, e.g. PET, i.e. polyethylene terephthalate
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2375/00Polyureas; Polyurethanes
    • BPERFORMING OPERATIONS; TRANSPORTING
    • B32LAYERED PRODUCTS
    • B32BLAYERED PRODUCTS, i.e. PRODUCTS BUILT-UP OF STRATA OF FLAT OR NON-FLAT, e.g. CELLULAR OR HONEYCOMB, FORM
    • B32B2605/00Vehicles
    • B32B2605/08Cars

Definitions

  • the present invention relates to transparent or semi-transparent laminates having a photochromic feature. More specifically, the present invention relates to transparent or semi-transparent laminates of glass and a resin film comprising a photochromic moiety.
  • Tinted glass is often useful in the automotive, building and other industries. Tinting of optical lenses is also useful and, in some cases, it is known to tint optical lenses with a photochromic moiety to provide a lens which changes tint in response to sunlight or uv light. While it is common to tint glass to provide some protection against bright sunlight and/or uv light, it is not well known to provide large scale photochromic glass. This may be due to the relatively high cost of photochromic moieties or other processing problems or perhaps to the longevity expected of photochromic moieties in use. However, whatever the reason, it would be useful and beneficial if a photochromic glass could be provided which was both effective and economical.
  • the present invention relates to a method and product by which glass is coated with a resin film having a photochromic feature.
  • glass may be coated with a resin film which is bonded thereto by an adhesive having a photochromic moiety therein to impart a photochromic nature to the laminate.
  • tinted glass has become popular and is well known throughout the world, it would be highly desirable for some uses to have tinted glass which changes tint in response to the amount of sunlight or uv light exposure. Glass windows or panes often suffer from the disadvantage that the windows are consistently tinted during both day and night. Tinted windows may interfere with visibility during hours of darkness. Thus, it would be advantageous to have glass panes which are desirably tinted during hours of bright sunshine and yet not tinted during hours of darkness, at least not to an extent that would interfere with good visibility. r , r frett -, -
  • Photochrornic tinting offers one method for providing tinting in bright sunshine but not in the dark.
  • photochromic tinting encounters some of its own problems.
  • One problem is that the life of photochromic moeities is relatively short and may not be suited for uses which require relatively long life cycles.
  • Another problem is that the photochromic moieties must be provided in a matrix which is suitable for the intended end use. For example, in some cases a tint may be required to have a fast change of state and in other cases a slow change of state maybe acceptable. In most cases, however, it would be desirable to have a photochromic moiety which is carried in a matrix which facilitates relatively long life for the moiety.
  • a preferred embodiment of the invention is a laminate having a glass layer with an optically clear film, preferably a removable optically clear film, adhesively laminated thereon with at least one of the film and the adhesive comprising a photochromic moiety.
  • the glass may comprise a uv absorber or antioxidant.
  • the optically clear film is selected from the group consisting of polyethylene terephthalate (PET), polyurethane, and polyethylene.
  • Figure 1 is a cross-sectional view, broken away, of a preferred laminate of the present invention.
  • Figure 2 is a somewhat schematic illustrating a preferred method of making a laminate of the present invention.
  • Laminate 10 has glass layer 12 and an adhesive layer 14 securing optically clear resin layer 16 thereon. It is contemplated that at least one of adhesive layer 14 and resin layer 16 will comprise an effective amount of a photochromic moiety and that the resin of resin layer 16 will be selected from the group consisting of optically clear PET, optically clear polyurethane and optically clear polyethylene resins.
  • Suitable glass for use in the present invention include all varieties of glass so long as the glass is suitable for its intended end use. Automotive glasses are especially contemplated for use herein.
  • Suitable adhesives for use herein are those which are effective to bond the selected optically clear resin layer to the glass layer. It is preferred for many uses that the optically clear resin layer be removable and, a preferred class of adhesives for use herein are pressure sensitive adhesives such as acResin A 258 UV which is a pressure sensitive adhesive commercially available from Bayer plastics.
  • Suitable optically clear resins for use herein are optically clear resins wherein the primary polymer in the resin is PET, polyurethane or polyethylene.
  • An example of a suitable optically clear polyurethane is Bayer Texin 285 thermoplastic elastomer.
  • An example of a suitable optically clear PET is Lumirror PET from Toray Plastic.
  • Suitable photochromic moieties are well-known in the art and include those selected from the group consisting of anthraquinones, naphtopyrans, phhalocyanines, spiro-oxazines, chromenes, pyrans including spiro-pyrans and fulgides.
  • Suitable photochromic molecules include but are not limited to those disclosed in United States Patents Nos. 5,882,556 March 16, 1999 to Perrott et al. which is specifically incorporated by reference herein.
  • Reversacl photochromic dyes commercially available from James ,,,, excessive ,. , p WO 2008/020 ⁇ p, y
  • the photochromic composition may include a non-photochromic dye if it is desired to provide a tint to the lens even when the photochromic molecules are not activated.
  • uv absorbers ultraviolet absorbers
  • light stabilizers antioxidants
  • free radical inhibitors have a beneficial effect on the life of the photochromic moiety.
  • hindered amine light stabilizers or HALS examples include Sanduvor 3051, 3052, 3055, 3056 from Sand ⁇ z/Clariant, Tinuvin 770, 765, 144, 622 from Ciba Geigy, Cyasorb 3346 from American Cyanamid.
  • antioxidants include Irganox 3114 from Ciba Geigy.
  • Suitable uv absorbers work by absorbing ultraviolet radiation and converting the radiation into thermal energy through tautomerism.
  • the selected uv absorber must not substantially absorb the range of uv light required to activate the photochromic moiety.
  • suitable uv absorbers include Cyasorb W-9 and UV 531, Cyaguard UV 1164 and 1084 from American Cyanamid, Sanduvor VSU from Sandoz/Clariant, Uvinul 3035 from BASF, Tinuvin 328 and P and Irgastab 2002 from Ciba Geigy, Rylex NBC from Dupont, UV Chek AM 101, 105, 126, and 205 from Ferro Corp and Carstab 700 from Morton International.
  • a converyor belt 22 travels in the direction indicated by numeral 24, conveying glass sheet 26 first underneath extruder 28.
  • Extruder 28 extrudes pressure sensitive adhesive 30 onto the upper surface of glass sheet 26 to form a layer 32 of pressure sensitive adhesive thereon.
  • rolls 34 P ⁇ T / I ⁇ ⁇ R and 36 feed and press resin film 38 onto adhesive layer 32 and effect a bonding of film 38 to glass sheet 26.
  • glass sheet 26, adhesive 30 and film 38 are as described herein.
  • Bayer Texin 285 TPU pellets are coated with mineral oil at 15 drops mineral oil per 1000 grams TPU by tumbling. Then 0.30Og (per lOOOg TPU) of Rush Yellow photochromic moiety from Keystone Aniline and 0.20Og (per lOOOg TPU) of Irganox 1035 are tumbled into the TPU. The mixture is then dried at 100 Q C for 2 hours.
  • the mixture is then extruded by a conventional extruder into 0.005 inch thick sheet stock.
  • the sheet is then coated with an acrylic pressure sensitive adhesive and applied to a sheet of glass to form a laminate.
  • the sheet When the laminate is exposed to uv light the sheet turns a bright yellow color and returns to clear when it is removed from the uv light.
  • a 0.002 inch thick sheet of optically clear PET (Lumirror PET from Toray Plastic is coated with a mixture of lOOg of QS 1162 polyurethane adhesive from Mace Company mixed with 0.01 Og of Keystone Anilane Oxford Blue photochromic dye and 0.01 Og of Tinuvin 770 HALS. Then the PET sheet is bonded to a piece of tempered glass and run through a pinch roller to remove all air bubbles to form a laminate.
  • the laminate is then exposed to uv light which causes it to turn a blue color while under the uv light.
  • the photochromic dye fade rate is noted as being exceptionally rapid.

Abstract

A glass laminate comprising a glass layer (12) and removable adhesive layer (M) securing optically clear resin layer (16) to the glass layer, wherein at least one of the adhesive layer (14) or the optically clear resin layer (16) comprises an effective amount of photochromic moiety. The optically clear resin layer is polyethylene trephthalate layer, polyurethane layer or polyethylene layer.

Description

EXTRUDED PHOTOCHROMIC FILM ON GLASS
BACKGROUND OF THE INVENTION
The present invention relates to transparent or semi-transparent laminates having a photochromic feature. More specifically, the present invention relates to transparent or semi-transparent laminates of glass and a resin film comprising a photochromic moiety.
Tinted glass is often useful in the automotive, building and other industries. Tinting of optical lenses is also useful and, in some cases, it is known to tint optical lenses with a photochromic moiety to provide a lens which changes tint in response to sunlight or uv light. While it is common to tint glass to provide some protection against bright sunlight and/or uv light, it is not well known to provide large scale photochromic glass. This may be due to the relatively high cost of photochromic moieties or other processing problems or perhaps to the longevity expected of photochromic moieties in use. However, whatever the reason, it would be useful and beneficial if a photochromic glass could be provided which was both effective and economical.
The present invention relates to a method and product by which glass is coated with a resin film having a photochromic feature. Alternatively, glass may be coated with a resin film which is bonded thereto by an adhesive having a photochromic moiety therein to impart a photochromic nature to the laminate. Athough tinted glass has become popular and is well known throughout the world, it would be highly desirable for some uses to have tinted glass which changes tint in response to the amount of sunlight or uv light exposure. Glass windows or panes often suffer from the disadvantage that the windows are consistently tinted during both day and night. Tinted windows may interfere with visibility during hours of darkness. Thus, it would be advantageous to have glass panes which are desirably tinted during hours of bright sunshine and yet not tinted during hours of darkness, at least not to an extent that would interfere with good visibility. r , r „ „ -, -
Photochrornic tinting offers one method for providing tinting in bright sunshine but not in the dark. However, photochromic tinting encounters some of its own problems. One problem is that the life of photochromic moeities is relatively short and may not be suited for uses which require relatively long life cycles. Another problem is that the photochromic moieties must be provided in a matrix which is suitable for the intended end use. For example, in some cases a tint may be required to have a fast change of state and in other cases a slow change of state maybe acceptable. In most cases, however, it would be desirable to have a photochromic moiety which is carried in a matrix which facilitates relatively long life for the moiety.
Further understanding of the present invention will be had from the following specification taken in conjunction with the accompanying drawings.
SUMMARY OF THE INVENTION
A preferred embodiment of the invention is a laminate having a glass layer with an optically clear film, preferably a removable optically clear film, adhesively laminated thereon with at least one of the film and the adhesive comprising a photochromic moiety.. Optionally, the glass may comprise a uv absorber or antioxidant. Preferably, the optically clear film is selected from the group consisting of polyethylene terephthalate (PET), polyurethane, and polyethylene.
BRIEF DESCRIPTION OF THE DRAWINGS
Figure 1 is a cross-sectional view, broken away, of a preferred laminate of the present invention; and
Figure 2 is a somewhat schematic illustrating a preferred method of making a laminate of the present invention.
DESCRIPTION OF THE PREFERRED EMBODIMENTS „
P c 'T,/ us «1 fa / 3 ,i. /
Now referring to Figure 1, a preferred laminate of the present invention is illustrated and indicated generally by the numeral 10. Laminate 10 has glass layer 12 and an adhesive layer 14 securing optically clear resin layer 16 thereon. It is contemplated that at least one of adhesive layer 14 and resin layer 16 will comprise an effective amount of a photochromic moiety and that the resin of resin layer 16 will be selected from the group consisting of optically clear PET, optically clear polyurethane and optically clear polyethylene resins.
Suitable glass for use in the present invention include all varieties of glass so long as the glass is suitable for its intended end use. Automotive glasses are especially contemplated for use herein.
Suitable adhesives for use herein are those which are effective to bond the selected optically clear resin layer to the glass layer. It is preferred for many uses that the optically clear resin layer be removable and, a preferred class of adhesives for use herein are pressure sensitive adhesives such as acResin A 258 UV which is a pressure sensitive adhesive commercially available from Bayer plastics.
Suitable optically clear resins for use herein are optically clear resins wherein the primary polymer in the resin is PET, polyurethane or polyethylene. An example of a suitable optically clear polyurethane is Bayer Texin 285 thermoplastic elastomer. An example of a suitable optically clear PET is Lumirror PET from Toray Plastic.
Suitable photochromic moieties are well-known in the art and include those selected from the group consisting of anthraquinones, naphtopyrans, phhalocyanines, spiro-oxazines, chromenes, pyrans including spiro-pyrans and fulgides. Suitable photochromic molecules include but are not limited to those disclosed in United States Patents Nos. 5,882,556 March 16, 1999 to Perrott et al. which is specifically incorporated by reference herein. Reversacl photochromic dyes commercially available from James ,,,, „ ,. , p WO 2008/020 π p, y
Robinson are particularly suitable for use herein. In addition to photochromic molecules, the photochromic composition may include a non-photochromic dye if it is desired to provide a tint to the lens even when the photochromic molecules are not activated.
It has been found that a limited amount of ultraviolet (uv) absorbers, light stabilizers, antioxidants, and or free radical inhibitors may also be included in either the optically clear resin layer or adhesive layer. The use of uv absorbers should be limited to some extent because they tend to have a detrimental effect on the life of the photochromic moiety. On the other hand, free radical inhibitors have a beneficial effect on the life of the photochromic moiety.
Examples of hindered amine light stabilizers or HALS include Sanduvor 3051, 3052, 3055, 3056 from Sandσz/Clariant, Tinuvin 770, 765, 144, 622 from Ciba Geigy, Cyasorb 3346 from American Cyanamid. Examples of antioxidants include Irganox 3114 from Ciba Geigy.
Suitable uv absorbers work by absorbing ultraviolet radiation and converting the radiation into thermal energy through tautomerism. Of course, the selected uv absorber must not substantially absorb the range of uv light required to activate the photochromic moiety. Examples of suitable uv absorbers include Cyasorb W-9 and UV 531, Cyaguard UV 1164 and 1084 from American Cyanamid, Sanduvor VSU from Sandoz/Clariant, Uvinul 3035 from BASF, Tinuvin 328 and P and Irgastab 2002 from Ciba Geigy, Rylex NBC from Dupont, UV Chek AM 101, 105, 126, and 205 from Ferro Corp and Carstab 700 from Morton International.
. Now referring to Figure 2, a preferred method of the present invention is shown and indicated generally by the numeral 20. As illustrated in Figure 2, a converyor belt 22 travels in the direction indicated by numeral 24, conveying glass sheet 26 first underneath extruder 28. Extruder 28 extrudes pressure sensitive adhesive 30 onto the upper surface of glass sheet 26 to form a layer 32 of pressure sensitive adhesive thereon. Then, rolls 34 P π T / IΛ π R and 36 feed and press resin film 38 onto adhesive layer 32 and effect a bonding of film 38 to glass sheet 26. Of course it is contemplated that glass sheet 26, adhesive 30 and film 38 are as described herein.
Further understanding of the present invention will be had from the following examples.
Example 1
Bayer Texin 285 TPU pellets are coated with mineral oil at 15 drops mineral oil per 1000 grams TPU by tumbling. Then 0.30Og (per lOOOg TPU) of Rush Yellow photochromic moiety from Keystone Aniline and 0.20Og (per lOOOg TPU) of Irganox 1035 are tumbled into the TPU. The mixture is then dried at 100 QC for 2 hours.
The mixture is then extruded by a conventional extruder into 0.005 inch thick sheet stock. The sheet is then coated with an acrylic pressure sensitive adhesive and applied to a sheet of glass to form a laminate.
When the laminate is exposed to uv light the sheet turns a bright yellow color and returns to clear when it is removed from the uv light.
Example 2
A 0.002 inch thick sheet of optically clear PET (Lumirror PET from Toray Plastic is coated with a mixture of lOOg of QS 1162 polyurethane adhesive from Mace Company mixed with 0.01 Og of Keystone Anilane Oxford Blue photochromic dye and 0.01 Og of Tinuvin 770 HALS. Then the PET sheet is bonded to a piece of tempered glass and run through a pinch roller to remove all air bubbles to form a laminate.
The laminate is then exposed to uv light which causes it to turn a blue color while under the uv light. When removed from the uv light the photochromic dye fade rate is noted as being exceptionally rapid.

Claims

! '' What is claimed is:
1. A laminate comprising a glass sheet layer having a surface with an optically clear resin layer bonded thereon with an adhesive layer, at least one of said clear resin layer or said adhesive comprising a photochromic moiety, said clear resin being selected from the group consisting of PET, polyurethane and polyethylene resin.
2. A laminate as in claim 1 wherein said clear resin is PET.
3. A laminate as in claim 1 wherein said clear resin is polyurethane resin.
4. A laminate as in claim 1 wherein said clear resin is polyethylene resin.
5. A laminate as in claim 1 wherein said glass sheet layer is an automotive glass sheet layer.
6. A laminate as in claim 5 wherein said glass layer is in association with an automotive vehicle.
7. A laminate as in claim 1 wherein said resin layer comprises an effective amount of said photochromic moiety.
8. A laminate as in claim 1 wherein said adhesive comprises an effective amount of said photochromic moiety.
9 A laminate as in claim 1 wherein at least one of said clear resin layer or said adhesive comprises one or more additives selected from the group consisting of an ultraviolet (uv) absorber, a light stabilizer, an antioxidant, and a free radical inhibitor.
10. A laminate as in claim 1 wherein said adhesive is a pressure sensitive adhesive.
11. The method of making a laminate of a resin layer bonded onto a glass sheet by an optically clear resin layer, comprising the steps of
Coating an adhesive layer onto a sheet of an optically clear resin layer selected from the group consisting of PET, polyurethane and polyethylene resin;
at least one of said clear resin layer and said adhesive layer comprising a photochromic moiety; and
bonding said clear resin layer to a glass sheet.
12. A method as in claim 11 wherein said clear resin is PET.
13. A method as in claim 11 wherein said clear resin layer comprises a polyurethane resin.
14. A method as in claim 11 wherein said clear resin layer comprises a polyethylene resin.
15. A method as in claim 11 wherein said glass sheet is an automotive glass sheet in association with an automotive vehicle.
16. A method as in claim 11 wherein said resin layer comprises an effective amount of said photochromic moiety. ,„ ,....,. ...,, , , (| r, lR
17. A method as m claim 11 wherein said adhesive comprises an effective amount of said photochromic moiety.
18 A method as in claim 11 wherein at least one of said clear resin layer or said adhesive comprises one or more additives selected from the group consisting of an ultraviolet (uv) absorber, a light stabilizer, an antioxidant, and a free radical inhibitor.
19. A method as in claim 11 wherein said adhesive is a pressure sensitive adhesive.
PCT/US2006/031087 2006-08-09 2006-08-09 Extruded photochromic film on glass WO2008020829A2 (en)

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WO2008020829A3 WO2008020829A3 (en) 2008-07-17

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010004021A2 (en) * 2008-07-11 2010-01-14 Thales Multilayer structure having a photochromic host matrix and manufacturing method
CN103243902A (en) * 2013-04-27 2013-08-14 张家港市贝尔机械有限公司 Method for preparing press-embedded glass fiber reinforced building templates

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0294056A2 (en) * 1987-05-22 1988-12-07 Pilkington Plc Manufacture of photochromic articles
EP1072959A1 (en) * 1999-07-30 2001-01-31 Nippon Shokubai Kabushiki Kaisha Phthalocyanine compound, method for production thereof, and near infrared absorption dye using the compound

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0294056A2 (en) * 1987-05-22 1988-12-07 Pilkington Plc Manufacture of photochromic articles
EP1072959A1 (en) * 1999-07-30 2001-01-31 Nippon Shokubai Kabushiki Kaisha Phthalocyanine compound, method for production thereof, and near infrared absorption dye using the compound

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2010004021A2 (en) * 2008-07-11 2010-01-14 Thales Multilayer structure having a photochromic host matrix and manufacturing method
WO2010004021A3 (en) * 2008-07-11 2010-06-24 Thales Multilayer structure having a photochromic host matrix and manufacturing method
US8345342B2 (en) 2008-07-11 2013-01-01 Thales Multilayer structure having a photochromic host matrix and manufacturing method
CN103243902A (en) * 2013-04-27 2013-08-14 张家港市贝尔机械有限公司 Method for preparing press-embedded glass fiber reinforced building templates

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