WO2005019281A1 - Photochromic pressure sensitive adhesive compositions - Google Patents
Photochromic pressure sensitive adhesive compositions Download PDFInfo
- Publication number
- WO2005019281A1 WO2005019281A1 PCT/US2003/025690 US0325690W WO2005019281A1 WO 2005019281 A1 WO2005019281 A1 WO 2005019281A1 US 0325690 W US0325690 W US 0325690W WO 2005019281 A1 WO2005019281 A1 WO 2005019281A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- adhesive
- composition
- pressure sensitive
- photochromic
- sensitive adhesive
- Prior art date
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Classifications
-
- G—PHYSICS
- G02—OPTICS
- G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
- G02B5/00—Optical elements other than lenses
- G02B5/20—Filters
- G02B5/22—Absorbing filters
- G02B5/23—Photochromic filters
Landscapes
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Optics & Photonics (AREA)
- Adhesives Or Adhesive Processes (AREA)
Abstract
A photochromic pressure sensitive adhesive composition is provided comprised of a pressure sensitive adhesive in combination with a photochromic compound, said photochromic compound being present in said adhesive in an amount sufficient to effect a color change in said adhesive in the presence of a suitable radiation source, and said adhesive not being a styrene-based rubber adhesive.
Description
Photochromic Pressure Sensitive Adhesive Compositions
Background of the Invention
The present invention is directed to photochromic pressure sensitive
adhesive compositions which undergo rapid color development or change upon
exposure to sunlight or UV-radiation. The compositions may display a wide
range of colors ranging from blue, yellow, burgundy, orange to red, or any
combination of such, where the color change is reversible. The compositions
have particular applicability in connection with laminates or optical displays in
which the photochromic effect may be used with advantage.
Photochromic compounds are well-known and have wide application in
areas such as tinted optical materials such as windows, eyewear, optical display
screens, etc. A durable and layered photochromic film having a gas barrier
film layer is disclosed in published U.S. Patent application 2001/0009721.
Also, JP 09227845; K. Tadashi, et al is directed to rubber-based photochromic
adhesive compositions where the photochromic compound renders the
normally translucent adhesive visible for ease of application.
The following U.S. patents disclose various photochromic dyes and
their applications (mainly in the ophthalmic applications), each herein
incorporated by reference: 6,316,570; 6,296,785; 6,268,055; 6,187,444;
6,153,126; 6,149,841; 6,106,744; 6,068,797; 6,060,001 6,022,497 5,981,634;
5,955,520; 5,879,592; 5,869,658; 5,808,063; 5,770,115 5,723,072 5,708,064;
5,698,141; 5,552,090; 5,395,567; 5,340,857; 5,330,686 5,244,602 5,200,116;
5,185,390; 5,130,353; 5,066,818; 4,994,208; 4,986,934; 4,980,089; 4,936,995;
4,931,221; 4,931,220; 4,931,219; 4,909,963; 4,880,667; 4,816,584; 4,792,224;
4,720,547; 4,637,698; 4,634,767; 4,831,142; 4,785,097; 4,634,767; each
assigned to PPG Industries, Inc.; 6,080,338; 6,022,495; 5,753,146; 5,744,070;
5,674,432; 5,645,767; 5,637,262; 5,624,757; 5,585,042; 5,578,252; 5,565,147;
5,466,398; 5,464,567; 5,458,815; 5,451,344; 5,405,958; 5,391,327; 5,384,077;
5,369,158; 5,274,132; 5,238,981; each assigned to Transitions Optical, Inc.;
and 5,730,908; 5,242,624; 5,225,563; 5,225,113; 5,186,867; 5,180,524;
5,171,636; 5,110,922; and 5,055,576 each assigned to Enichem Synthesis
S.P.A.
The present invention provides the following advantages, among others:
(1) The rapid response kinetics of photochromic dyes in the present
invention provides ultra-fast color development or change compared with other
existing photochromic designs, which is a distinctive advantage for the
applications where rapid switch of color is desired or favored, such as
ophthalmic lenses, optical memories and switches;
(2) The composition of the present invention can be tailor-made to
achieve different colors and color intensity. The colors cover a wide range from
blue, yellow, burgundy, orange to red, or any of these combinations;
(3) The benefits of pressure sensitive adhesives afford the present
invention convenience in use and handling, repositioning, replacement, etc.;
(4) The photochromic pressure sensitive adhesive compositions may
comprise optically clear adhesives that feature high tack, good strippability,
low VOC outgassing and low extractable ions; and
(5) The adhesive composition may be formulated and a barrier of
backing film provided to effectively protect the photochromic dyes from
damaging UVB, residual acid, oxygen and/or moisture, and consequently
improve the performance and life time of the photochromic dyes.
The viscoelastic nature of pressure sensitive adhesives provides "free
volume" in the adhesive matrix, which enables enhanced photochromic
performance of the photochromic dyes. Compared with other existing
photochromic materials including photochromic plastics or glass, coatmg and
ink, the presence of higher amounts of free volume in the design of the present
invention effectively improves the kinetics of the photochromism through
facilitating the geometric rearrangement of the photochromic dyes. As a result,
upon exposure to sunlight or UV-radiation and removal of the exposure, the
pressure sensitive adhesive system allows color change between the ground
state and excited states of photochromic dyes in a fast and reversible manner.
Detailed Description of the Drawings
Figure 1 is a cross-sectional view of an adhesive tape comprised of the
photochromic pressure sensitive adhesive of the present invention.
Figure 2 is a cross-sectional view of another embodiment of an adhesive
tape comprised of the photochromic pressure sensitive adhesive of the present
invention.
Detailed Description of the Invention
The present invention is directed to a pressure sensitive adhesive
composition that remains pressure sensitive and tacky at and above room
temperature. The adhesive composition comprises a low concentration of
photochromic compounds such as naphthopyran or oxazine organic compounds,
which produce rapid color development or change when exposed to sunlight or
UV-radiation. More specifically, such photochromic compounds may include
azobenzene compounds, thioindigo compounds, spiropyran compounds,
fulgide compounds, triphenylmethane compounds, spirooxazine compounds,
viologen compounds, and salicyldineanil compounds, etc.
The color intensity increases continuously with increased exposure
time and reaches maximum color intensity or saturation typically within ten
seconds. Different color and color intensity can be pre-designed by adjusting
the formulation of the composition. The color change may, for example, range
from blue, yellow, burgundy, orange to red, or any of these combinations,
depending upon the identity of the photochromic compound(s) employed.
The color change process of the photochromic pressure sensitive
adhesive composition is reversible; i.e., the color intensity immediately starts to
decrease if the radiation exposure is removed or blocked. As is the nature of
photochromic dyes, the fading process occurs much slower than the darkening
process.
A variety of photochromic dyes may be employed in the practice of the
present invention. Upon exposure to suitable radiation such as ultraviolet
radiation, the photochromic compound absorbs at wavelengths in the visible
range. For instance, the absorption of red photons from white light leaves a
blue color. Upon removal of the radiation source, the net observation is a
return to a colorless state. The life of the photochromic reaction depends upon
many factors, including the amount of the photochromic compound employed
in the composition, the intensity and length of the UV exposure, whether any
stabilizers are present in the composition, and the type of adhesive which is
used as the matrix material. Ultraviolet absorbers can also be employed to
extend the life of the photochromic material, but their presence will also
diminish the intensity of the color.
The presence of free radicals such as oxygen, oxidizers such as peroxide,
acids and high energy ultraviolet may diminish the stability of the
photochromic compounds. Protective agents such as antioxidants, UV
stabilizers, free radical scavengers, color neutralizing agents, etc. may be used
to protect against such free radicals. It is also preferred to employ a backing
film which has a low oxygen permeability to minimize the effect of oxygen on
the long term stability of the composition.
The photochromic compounds may be admixed with the pressure
sensitive adhesive by any conventional method, such as by physical admixing,
extruding, casting, etc. Such compounds are generally stable at temperatures in
the range of 180 to 240°C for short periods of time without degradation, and
may thus be admixed or combined with the pressure sensitive adhesive under
conditions of elevated temperature as may be required.
The identity of the pressure sensitive adhesive used in the present
invention is not critical and may comprise a variety of adhesives, including but
not limited to adhesives such as polyvinyl ethers, acrylic adhesives, poly-alpha-
olefins, and silicone adhesives, as well as blends thereof, with the proviso that
the adhesive is not a styrene-based rubber adhesive.
Polyvinyl ether pressure sensitive adhesives generally comprise blends
of vinyl methyl ether , vinyl ethyl ether or vinyl iso-butyl ether, or
homopolymers of vinyl ethers and acrylates. Acrylic pressure sensitive
adhesives may comprise, for example, a C3-12 alkyl ester component and a polar
component such as (meth)acrylic acid, N-vinyl pyrrolidone, etc. Such
adhesives may be tackified. Poly-alpha-olefins adhesives comprise an
optionally crosslinked C3-18 poly(alkene) polymer, which is either self-tacky or
may include a tackifier. Silicone pressure sensitive adhesives comprise a
polymer or gum constituent and a tackifying resin.
More specifically, the acrylic pressure sensitive adhesive is preferably
comprised of a polymer formed from the reaction product of at least one
acrylate A monomer and a B monomer different from the A monomer.
The at least one A monomer preferably comprises a monomeric
(meth)acrylic acid ester of a non-tertiary alcohol where the alcohol portion has
from 1 to 30 carbon atoms. Exemplary A monomers include but are not
limited to esters of acrylic acid or methacrylic acid with non-tertiary alcohols
such as 1-butanol, 1-pentanol, 2-pentanol, 3-pentanol, 2-methyl-l-butanol, 1-
methyl-1-pentanol, 2-methyl- 1-pentanol, 3 -methyl- 1-pentanol, 2-ethyl-l-
butanol, 3,5,5-trimethyl-l-hexanol, 3-heptanol, 2-octanol, 1-decanol, 1-
dodecanol, etc. Such monomers are well-known to those skilled in the art. The
least one A monomer component (if more than one A monomer is present) will
preferably exhibit an average number of carbon atoms in the alcohol portion of
the total acrylic or (meth)acrylic acid esters of from 3 to 16.
One or more polymerizable B monomers different from the A monomer
may be incorporated in the polymer which B monomer(s) is copolymerizable
with the A monomer. Such additional B monomer(s) may be either hydrophilic
or hydrophobic.
Exemplary optional B monomers include vinyl monomers having at
least one nitrogen atom. Such monomers (each of which exhibit a Tg of >20
°C.) include but are not limited to N-mono-substituted acrylamides such as
acrylamide, methacrylamide, N-methylacrylamide, N-ethylacrylamide, N-
methylolacrylamide, N-hydroxyethylacrylamide, and diacetone acrylamide;
N,N-disubstituted acrylamides such as N,N-dimethylacrylamide, N,N-
diethylacrylamide, N-ethyl-N-aminoethyl acrylamide, N-ethyl-N-
hydroxyethylacrylamide, N,N-dimethylolacrylamide, and N,N-
dihydroxyethylacrylamide, etc.
Other optional B monomers may include, for example, various vinyl
monomers such as (meth)acrylic acid, itaconic acid, crotonic acid,
methoxyethyl (meth)acrylate, ethyoxyethyl (meth)acrylate, glycerol
(meth)acrylate, hydroxyethyl methacrylate, hydroxypropyl methacrylate, beta-
carboxyethyl acrylate, vinyl pyrrolidone, vinyl caprolactam and caprolactam
acrylate. One or more B monomers may be employed.
Such pressure sensitive adhesives are well known to one of ordinary
skill in the art and may be easily selected by such persons for use in the present
invention.
The pressure sensitive adhesive composition of the present invention
may, for example, be comprised of the following: a) From about 90 to about 99.95% by weight of a prbssure sensitive adhesive or adhesive blend as the base material. Such adhesives include but are not limited to acrylic polymers or copolymers. Exemplary polymer or copolymer compositions may be comprised of, for example, tert-butylmethacrylate, butyl acrylate, glycidyl methacrylate, 2-ethylhexylacylate, hydroxylethylacrylate, isobornyl methacrylate, N-vinylpyrrolidone and vinyl acetate. b) From about 0.05 to about 10% by weight of a photochromic dye or a blend of two or more photochromic dyes. Such photochromic dyes include but are not limited to organic naphthopyrans and oxazines. Examples of these dyes are Photosol™ photochromic dyes (PPG Industries, Inc.).
c) From about 0 to about 5.0% by weight of an antioxidant. Examples of antioxidants include but are not limited to pentaerythritol tetrakis(3-(3,5-di-tert-butyl-4- hydroxyphenyι)propionate or 2,6-di-tert. butyl -4-methyl phenol.
The photochromic pressure sensitive adhesive composition of the
present invention may be used in a variety of end uses with advantage,
including but not being limited to the following: removable and replaceable
films for ophthalmic applications such as transition lenses and ski goggles;
contrast-enhancing and energy-saving film for LCD display to replace the
current tint films; UV dosimeter and UV-index indicator; sunlight readable
displays; security badges and displays; new types of light detectors, optical
switches; low-cost memory device for optical computers and memory-device
applications; eyewear; labels; energy efficient window films such as building
and automotive windows; etc. In such embodiments, the photochromic
pressure sensitive adhesive composition of the present invention may be
employed as a thin film bonded to a light transmissive layer together with a
backing material or another light transmissive layer.
The invention is described in connection with the following examples,
which are provided solely for purposes of illustration and are not intended to
limit the invention.
Example
Six photochromic pressure sensitive adhesive compositions are provided
and coated on 3-mil Melinex® 453 polyester film and dried at 150°F to produce
pressure sensitive adhesive compositions. The photochromic compound is
admixed with the pressure sensitive adhesive composition by dissolving the
photochromic dye and Irganox 1010 in toluene and blending with an acrylic
adhesive (Gelva 788) to yield the compositions set forth in Table 1 below:
Table 1
Sample No. 1 2 3 4 5 6
Photochromic dye A B C D E F
Dye amount (g) 0.42 0.44 0.42 0.44 0.39 0.42
Adhesive (g) 43.4 46.6 40.7 47.1 39.9 65.0
Irganox 1010 (g) 0.19 0.15 0.14 0.15 0.13 0.14
Toluene (g) 7.4 8.8 7.7 8.1 8.0 7.5
Note: The ph otochrom tic dyes A-F employ f d in Sar nples 1-6 are (A) Photosol 5-3, (B) Photosol 02-65, (C) Photosol 7-106, (D) Photosol 336- 72, (E) Photosol 5-83, (F) Photosol 7-49 (each from PPG).
The pressure sensitive films prepared above were tested for
photochromic response under sunlight exposure outdoors. The compositions
were found to undergo acceptable darkening and fading under different periods
of exposure.
The photochromic pressure sensitive adhesive is easily produced
through solution coating. The adhesive composition is prepared by mixing the
photochromic dye, adhesive and additives such as antioxidant in a solvent or a
mixture of solvents, which include but are not limited to ethyl acetate, toluene,
vinyl acetate and methyl ethyl ketone. The adhesive solution is subsequently
coated on an optically clear backing film 1 followed by drying the solvent and
laminating with a release liner 3 with the photochromic pressure sensitive
adhesive layer 5 sandwiched therebetween. The construction of the pressure
sensitive adhesive tape is illustrated in Figure 1.
The pressure sensitive adhesives used in the present invention include
but are not limited to solvent-based, hot-melt, emulsion and liquid adhesive
systems (which can be cured at a second stage).
The backing film used in the construction shown in Figure 1 is
preferably a plastic film with the following optical properties: Light
Transmission not smaller than 75% at and above 330 nm and Haze not greater
than 0.5%) (ASTM D1003). A variety of films may be employed including but
not limited to polyethylene terephthalate, polyvinyl chloride, polyethylene,
polypropylene, and cellulose acetate. For applications where the substrate
itself is optically clear and can be exposed to UV radiation (such as glass plates,
etc.), alternative backing materials may be used such as metal, foam, paper and
pigmented plastics. The adhesive provides high tack, high adhesion and good
strippability on a wide range of substrate materials such as glass, plastics and
metal.
Another alternative construction design is to use two release liners to
produce transfer photochromic adhesive film. Such transfer films can be used
to bond two substrate materials, at least one of which is optically clear to
permit U.V. radiation to pass through the film.
Multiple layer constructions (Figure 2) may be used to produce
photochromic pressure sensitive adhesive tapes disclosed in the present
invention. This construction design is particularly suitable to applications
where a photochromic effect is desired for thick adhesive tapes. Despite that
UV radiation does not afford deep penetration, the first thin layer of pressure
sensitive adhesive 5 produces the maximum photochromic performance, while
the second layer of pressure sensitive adhesive 7 can be tailor-made to produce
good bonding and conformability to various substrate materials. A carrier layer
9 is placed therebetween. When a release liner 3 is used in the replacement of
the backing film 1, this multiple layer construction is also particularly useful
for bonding two substrate materials, which are very different in nature and
chemistry and at least one is optically clear.
Claims
1. A photochromic pressure sensitive adhesive composition comprised
of a pressure sensitive adhesive in combination with a photochromic compound,
said photochromic compound being present in said adhesive in an amount
sufficient to effect a color change in said adhesive in the presence of a suitable
radiation source, and said adhesive not being a styrene-based rubber adhesive.
2. The composition of claim 1 wherein said photochromic compound is
present in said composition in an amount in the range of from about 0.05 to
about 10 % by weight, based on the total weight of the composition.
3. The composition of claim 1 wherein said pressure sensitive adhesive
is present in said composition in an amount within the range of about 90 to
about 99.5% by weight, based on the total weight of the composition.
4. The composition of claim 1 further comprising a component selected
from the group consisting of an antioxidant, UV stabilizer, free radical
scavenger, color neutralizing agent, or mixtures thereof.
5. The composition of claim 1 in the form of a film.
6. The composition of claim 5 further comprising a backing film.
7. The composition of claim 1 wherein the pressure sensitive adhesive is
selected from the group consisting of polyvinyl ethers, acrylic adhesives, poly-
alpha-olefins, silicone adhesives, and mixtures thereof.
8. A laminate having photochromic properties comprised of a layer of a
pressure sensitive adhesive in combination with a photochromic compound,
said photochromic compound being present in said adhesive in an amount
sufficient to effect a color change in said adhesive in the presence of a suitable
radiation source, and an optically clear backing layer, and said adhesive not
being a styrene-based rubber adhesive.
9. The laminate of claim 8 wherein said backing layer exhibits light
transmission not smaller than 75% at and above 330 nm and haze not greater
than 0.5% according to ASTM D1003.
10. The laminate of claim 8 wherein said backing layer is comprised of
glass or plastic.
11. The laminate of claim 8 wherein said pressure sensitive adhesive
layer is placed between two optically clear backing layers.
12. The laminate of claim 8 wherein a second non-optically clear
backing layer is employed.
13. The laminate of claim 8 in combination with an LCD display as a
display screen.
14. The laminate of claim 11 in the form of a window.
15. The laminate of claim 8 in combination with eye goggles or glasses.
Priority Applications (2)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| AU2003259873A AU2003259873A1 (en) | 2003-08-18 | 2003-08-18 | Photochromic pressure sensitive adhesive compositions |
| PCT/US2003/025690 WO2005019281A1 (en) | 2003-08-18 | 2003-08-18 | Photochromic pressure sensitive adhesive compositions |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| PCT/US2003/025690 WO2005019281A1 (en) | 2003-08-18 | 2003-08-18 | Photochromic pressure sensitive adhesive compositions |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| WO2005019281A1 true WO2005019281A1 (en) | 2005-03-03 |
Family
ID=34215331
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| PCT/US2003/025690 WO2005019281A1 (en) | 2003-08-18 | 2003-08-18 | Photochromic pressure sensitive adhesive compositions |
Country Status (2)
| Country | Link |
|---|---|
| AU (1) | AU2003259873A1 (en) |
| WO (1) | WO2005019281A1 (en) |
Cited By (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| WO2008014529A1 (en) * | 2006-08-01 | 2008-02-07 | Teich Aktiengesellschaft | Falsification-proof foil and blister pack comprising this foil |
| DE102006048338A1 (en) * | 2006-10-12 | 2008-04-17 | Agfaphoto Gmbh | Photochromic material for coating objects such as window panes, comprises a flexible support coated with a photochromic composition and then with an oxygen barrier layer |
| WO2010004021A2 (en) * | 2008-07-11 | 2010-01-14 | Thales | Multilayer structure having a photochromic host matrix and manufacturing method |
| US20110272082A1 (en) * | 2005-06-30 | 2011-11-10 | Michael Dunleavy | Fibre Materials |
| WO2012115116A1 (en) * | 2011-02-22 | 2012-08-30 | リンテック株式会社 | Pressure-sensitive adhesive composition, and adhesive sheet |
| WO2013006153A1 (en) * | 2011-07-01 | 2013-01-10 | Essilor International (Compagnie Generale D'optique) | Temporary photochromic patch for an ophthalmic lens |
| GB2495505A (en) * | 2011-10-11 | 2013-04-17 | Hd Inspiration Holding B V | Visor with photochromatic insert |
| CN103529617A (en) * | 2013-09-16 | 2014-01-22 | 无锡创彩光学材料有限公司 | Photochromic laminating film and manufacturing method thereof |
| EP2727657A4 (en) * | 2011-06-28 | 2015-03-04 | Kokuyo Kk | Coating product and coating system |
| US9382428B2 (en) | 2011-06-28 | 2016-07-05 | 3M Innovative Properties Company | Liquid tint materials and films made therefrom |
| CN106019422A (en) * | 2016-07-08 | 2016-10-12 | 安徽省光学膜材料工程研究院有限公司 | Optical release film |
| CN110568616A (en) * | 2013-05-02 | 2019-12-13 | 依视路国际公司 | Method for providing a head-mounted optical system |
| US11235349B2 (en) | 2012-06-25 | 2022-02-01 | 3M Innovative Properties Company | Devices for coating contoured surfaces |
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|---|---|---|---|---|
| JPH09227845A (en) * | 1996-02-21 | 1997-09-02 | Sony Chem Corp | Photochromic adhesive composition and adhesive sheet |
| JPH10330708A (en) * | 1997-06-05 | 1998-12-15 | Kiroku Sozai Sogo Kenkyusho:Kk | Photochromic adhesive composition |
| US5914174A (en) * | 1996-12-05 | 1999-06-22 | Innotech, Inc. | Lens or semi-finished blank comprising photochromic resin compositions |
| US6319433B1 (en) * | 1999-09-14 | 2001-11-20 | Invicta Corporation | Composite ophthalmic lens remolding system for forming a lens therein |
| US6461722B1 (en) * | 1998-10-06 | 2002-10-08 | Avery Dennnison Corporation | Thermal transfer laminate |
-
2003
- 2003-08-18 AU AU2003259873A patent/AU2003259873A1/en not_active Abandoned
- 2003-08-18 WO PCT/US2003/025690 patent/WO2005019281A1/en active Application Filing
Patent Citations (5)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| JPH09227845A (en) * | 1996-02-21 | 1997-09-02 | Sony Chem Corp | Photochromic adhesive composition and adhesive sheet |
| US5914174A (en) * | 1996-12-05 | 1999-06-22 | Innotech, Inc. | Lens or semi-finished blank comprising photochromic resin compositions |
| JPH10330708A (en) * | 1997-06-05 | 1998-12-15 | Kiroku Sozai Sogo Kenkyusho:Kk | Photochromic adhesive composition |
| US6461722B1 (en) * | 1998-10-06 | 2002-10-08 | Avery Dennnison Corporation | Thermal transfer laminate |
| US6319433B1 (en) * | 1999-09-14 | 2001-11-20 | Invicta Corporation | Composite ophthalmic lens remolding system for forming a lens therein |
Cited By (19)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US20110272082A1 (en) * | 2005-06-30 | 2011-11-10 | Michael Dunleavy | Fibre Materials |
| WO2008014529A1 (en) * | 2006-08-01 | 2008-02-07 | Teich Aktiengesellschaft | Falsification-proof foil and blister pack comprising this foil |
| DE102006048338A1 (en) * | 2006-10-12 | 2008-04-17 | Agfaphoto Gmbh | Photochromic material for coating objects such as window panes, comprises a flexible support coated with a photochromic composition and then with an oxygen barrier layer |
| WO2010004021A2 (en) * | 2008-07-11 | 2010-01-14 | Thales | Multilayer structure having a photochromic host matrix and manufacturing method |
| FR2933785A1 (en) * | 2008-07-11 | 2010-01-15 | Thales Sa | PHOTOCHROMATIC MATERIAL |
| 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 |
| WO2012115116A1 (en) * | 2011-02-22 | 2012-08-30 | リンテック株式会社 | Pressure-sensitive adhesive composition, and adhesive sheet |
| EP2727657A4 (en) * | 2011-06-28 | 2015-03-04 | Kokuyo Kk | Coating product and coating system |
| US10071394B2 (en) | 2011-06-28 | 2018-09-11 | Kokuyo Co., Ltd. | Application product and application system |
| US9382428B2 (en) | 2011-06-28 | 2016-07-05 | 3M Innovative Properties Company | Liquid tint materials and films made therefrom |
| WO2013006153A1 (en) * | 2011-07-01 | 2013-01-10 | Essilor International (Compagnie Generale D'optique) | Temporary photochromic patch for an ophthalmic lens |
| US20140118681A1 (en) * | 2011-07-01 | 2014-05-01 | Essilor International (Compagnie Generale D'optique) | Temporary photochromic patch for an ophtalmic lens |
| CN103649784A (en) * | 2011-07-01 | 2014-03-19 | 埃西勒国际通用光学公司 | Temporary photochromic patch for an ophthalmic lens |
| GB2495505A (en) * | 2011-10-11 | 2013-04-17 | Hd Inspiration Holding B V | Visor with photochromatic insert |
| US11235349B2 (en) | 2012-06-25 | 2022-02-01 | 3M Innovative Properties Company | Devices for coating contoured surfaces |
| CN110568616A (en) * | 2013-05-02 | 2019-12-13 | 依视路国际公司 | Method for providing a head-mounted optical system |
| CN103529617A (en) * | 2013-09-16 | 2014-01-22 | 无锡创彩光学材料有限公司 | Photochromic laminating film and manufacturing method thereof |
| CN106019422A (en) * | 2016-07-08 | 2016-10-12 | 安徽省光学膜材料工程研究院有限公司 | Optical release film |
Also Published As
| Publication number | Publication date |
|---|---|
| AU2003259873A1 (en) | 2005-03-10 |
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