WO2006039130A1 - Holographic storage medium - Google Patents
Holographic storage medium Download PDFInfo
- Publication number
- WO2006039130A1 WO2006039130A1 PCT/US2005/033438 US2005033438W WO2006039130A1 WO 2006039130 A1 WO2006039130 A1 WO 2006039130A1 US 2005033438 W US2005033438 W US 2005033438W WO 2006039130 A1 WO2006039130 A1 WO 2006039130A1
- Authority
- WO
- WIPO (PCT)
- Prior art keywords
- carbon atoms
- article
- alkyl
- nitrone
- radical containing
- Prior art date
Links
- 238000003860 storage Methods 0.000 title claims description 37
- 239000000203 mixture Substances 0.000 claims abstract description 60
- 238000000034 method Methods 0.000 claims abstract description 55
- 238000013500 data storage Methods 0.000 claims abstract description 35
- 239000011368 organic material Substances 0.000 claims abstract description 17
- 230000001678 irradiating effect Effects 0.000 claims abstract description 11
- 238000004519 manufacturing process Methods 0.000 claims abstract description 8
- 238000002156 mixing Methods 0.000 claims abstract description 8
- 238000000465 moulding Methods 0.000 claims abstract description 8
- 229910010272 inorganic material Inorganic materials 0.000 claims abstract description 7
- 239000011147 inorganic material Substances 0.000 claims abstract description 7
- -1 aryl nitrone Chemical compound 0.000 claims description 80
- 125000004432 carbon atom Chemical group C* 0.000 claims description 45
- 239000000975 dye Substances 0.000 claims description 40
- 150000001988 diarylethenes Chemical class 0.000 claims description 37
- 125000000217 alkyl group Chemical group 0.000 claims description 32
- 229920000515 polycarbonate Polymers 0.000 claims description 30
- 239000004417 polycarbonate Substances 0.000 claims description 30
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 29
- 239000000463 material Substances 0.000 claims description 28
- 229920000728 polyester Polymers 0.000 claims description 24
- 238000006243 chemical reaction Methods 0.000 claims description 22
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000001424 substituent group Chemical group 0.000 claims description 19
- 125000005010 perfluoroalkyl group Chemical group 0.000 claims description 18
- 229920000620 organic polymer Polymers 0.000 claims description 17
- 229920001187 thermosetting polymer Polymers 0.000 claims description 17
- 239000004634 thermosetting polymer Substances 0.000 claims description 17
- 125000004435 hydrogen atom Chemical class [H]* 0.000 claims description 16
- 229910052757 nitrogen Inorganic materials 0.000 claims description 16
- SQDFHQJTAWCFIB-UHFFFAOYSA-N n-methylidenehydroxylamine Chemical compound ON=C SQDFHQJTAWCFIB-UHFFFAOYSA-N 0.000 claims description 14
- 229920001169 thermoplastic Polymers 0.000 claims description 14
- 239000002253 acid Substances 0.000 claims description 13
- 125000003118 aryl group Chemical group 0.000 claims description 13
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical compound [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 13
- 239000001301 oxygen Substances 0.000 claims description 13
- 229910052760 oxygen Inorganic materials 0.000 claims description 13
- 125000005842 heteroatom Chemical group 0.000 claims description 12
- 229920000642 polymer Polymers 0.000 claims description 12
- PXGOKWXKJXAPGV-UHFFFAOYSA-N Fluorine Chemical compound FF PXGOKWXKJXAPGV-UHFFFAOYSA-N 0.000 claims description 10
- NINIDFKCEFEMDL-UHFFFAOYSA-N Sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 claims description 10
- 229910052731 fluorine Inorganic materials 0.000 claims description 10
- 239000011737 fluorine Substances 0.000 claims description 10
- 238000007363 ring formation reaction Methods 0.000 claims description 10
- 239000011593 sulfur Substances 0.000 claims description 10
- 229910052717 sulfur Inorganic materials 0.000 claims description 10
- 229920001577 copolymer Polymers 0.000 claims description 9
- 150000002148 esters Chemical class 0.000 claims description 8
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 8
- 239000000243 solution Substances 0.000 claims description 8
- 125000005843 halogen group Chemical group 0.000 claims description 7
- 239000002243 precursor Substances 0.000 claims description 7
- XHYQTIDZYNZAKZ-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]-n-phenylmethanimine oxide Chemical compound C1=CC(N(CC)CC)=CC=C1C=[N+]([O-])C1=CC=CC=C1 XHYQTIDZYNZAKZ-UHFFFAOYSA-N 0.000 claims description 6
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 claims description 6
- MWPLVEDNUUSJAV-UHFFFAOYSA-N anthracene Chemical compound C1=CC=CC2=CC3=CC=CC=C3C=C21 MWPLVEDNUUSJAV-UHFFFAOYSA-N 0.000 claims description 6
- 230000005670 electromagnetic radiation Effects 0.000 claims description 6
- YNPNZTXNASCQKK-UHFFFAOYSA-N phenanthrene Chemical compound C1=CC=C2C3=CC=CC=C3C=CC2=C1 YNPNZTXNASCQKK-UHFFFAOYSA-N 0.000 claims description 6
- 229920000058 polyacrylate Polymers 0.000 claims description 6
- 229920000570 polyether Polymers 0.000 claims description 6
- 229920000193 polymethacrylate Polymers 0.000 claims description 6
- 229920001296 polysiloxane Polymers 0.000 claims description 6
- 229920002635 polyurethane Polymers 0.000 claims description 6
- 239000004814 polyurethane Substances 0.000 claims description 6
- 239000004721 Polyphenylene oxide Substances 0.000 claims description 5
- 229920001400 block copolymer Polymers 0.000 claims description 5
- 125000004093 cyano group Chemical group *C#N 0.000 claims description 5
- 125000006575 electron-withdrawing group Chemical group 0.000 claims description 5
- 238000001746 injection moulding Methods 0.000 claims description 5
- 125000005647 linker group Chemical group 0.000 claims description 5
- 125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims description 5
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N phenol group Chemical group C1(=CC=CC=C1)O ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 claims description 5
- 229920001230 polyarylate Polymers 0.000 claims description 5
- 229920000098 polyolefin Polymers 0.000 claims description 5
- 125000000547 substituted alkyl group Chemical group 0.000 claims description 5
- 150000008064 anhydrides Chemical class 0.000 claims description 4
- 238000000071 blow moulding Methods 0.000 claims description 4
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 claims description 4
- 125000001624 naphthyl group Chemical group 0.000 claims description 4
- SJGALSBBFTYSBA-UHFFFAOYSA-N oxaziridine Chemical compound C1NO1 SJGALSBBFTYSBA-UHFFFAOYSA-N 0.000 claims description 4
- 238000007666 vacuum forming Methods 0.000 claims description 4
- 239000004593 Epoxy Substances 0.000 claims description 3
- 239000004696 Poly ether ether ketone Substances 0.000 claims description 3
- 239000004952 Polyamide Substances 0.000 claims description 3
- 239000004962 Polyamide-imide Substances 0.000 claims description 3
- 229920002614 Polyether block amide Polymers 0.000 claims description 3
- 239000004642 Polyimide Substances 0.000 claims description 3
- 239000004734 Polyphenylene sulfide Substances 0.000 claims description 3
- 239000004793 Polystyrene Substances 0.000 claims description 3
- 150000001299 aldehydes Chemical class 0.000 claims description 3
- 125000002947 alkylene group Chemical group 0.000 claims description 3
- 150000001732 carboxylic acid derivatives Chemical class 0.000 claims description 3
- 238000000748 compression moulding Methods 0.000 claims description 3
- 239000000412 dendrimer Substances 0.000 claims description 3
- 229920000736 dendritic polymer Polymers 0.000 claims description 3
- 230000005684 electric field Effects 0.000 claims description 3
- 229920000578 graft copolymer Polymers 0.000 claims description 3
- 229920000554 ionomer Polymers 0.000 claims description 3
- CTAPFRYPJLPFDF-UHFFFAOYSA-N isoxazole Chemical compound C=1C=NOC=1 CTAPFRYPJLPFDF-UHFFFAOYSA-N 0.000 claims description 3
- FFMJDYDBOMSRID-UHFFFAOYSA-N n-(3,4-dichlorophenyl)-1-[4-(diethylamino)phenyl]methanimine oxide Chemical compound C1=CC(N(CC)CC)=CC=C1C=[N+]([O-])C1=CC=C(Cl)C(Cl)=C1 FFMJDYDBOMSRID-UHFFFAOYSA-N 0.000 claims description 3
- KHIBJEZVFWHHNR-UHFFFAOYSA-N n-(4-acetylphenyl)-1-[4-(diethylamino)phenyl]methanimine oxide Chemical compound C1=CC(N(CC)CC)=CC=C1C=[N+]([O-])C1=CC=C(C(C)=O)C=C1 KHIBJEZVFWHHNR-UHFFFAOYSA-N 0.000 claims description 3
- ACYFFRIZRSNCKY-UHFFFAOYSA-N n-(4-chlorophenyl)-1-[4-(diethylamino)phenyl]methanimine oxide Chemical compound C1=CC(N(CC)CC)=CC=C1C=[N+]([O-])C1=CC=C(Cl)C=C1 ACYFFRIZRSNCKY-UHFFFAOYSA-N 0.000 claims description 3
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 3
- JMANVNJQNLATNU-UHFFFAOYSA-N oxalonitrile Chemical compound N#CC#N JMANVNJQNLATNU-UHFFFAOYSA-N 0.000 claims description 3
- 229920001643 poly(ether ketone) Polymers 0.000 claims description 3
- 229920001652 poly(etherketoneketone) Polymers 0.000 claims description 3
- 229920002492 poly(sulfone) Polymers 0.000 claims description 3
- 229920002647 polyamide Polymers 0.000 claims description 3
- 229920002312 polyamide-imide Polymers 0.000 claims description 3
- 229920006393 polyether sulfone Polymers 0.000 claims description 3
- 229920002530 polyetherether ketone Polymers 0.000 claims description 3
- 229920001601 polyetherimide Polymers 0.000 claims description 3
- 229920001721 polyimide Polymers 0.000 claims description 3
- 229920000069 polyphenylene sulfide Polymers 0.000 claims description 3
- 229920002223 polystyrene Polymers 0.000 claims description 3
- PBMFSQRYOILNGV-UHFFFAOYSA-N pyridazine Chemical compound C1=CC=NN=C1 PBMFSQRYOILNGV-UHFFFAOYSA-N 0.000 claims description 3
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 claims description 3
- 125000004076 pyridyl group Chemical group 0.000 claims description 3
- 229920005604 random copolymer Polymers 0.000 claims description 3
- 230000015572 biosynthetic process Effects 0.000 claims description 2
- 238000003618 dip coating Methods 0.000 claims description 2
- JWGFCIMTBBXAGP-UHFFFAOYSA-N n-(4-cyanophenyl)-1-(4-methoxyphenyl)methanimine oxide Chemical compound C1=CC(OC)=CC=C1C=[N+]([O-])C1=CC=C(C#N)C=C1 JWGFCIMTBBXAGP-UHFFFAOYSA-N 0.000 claims description 2
- ZFGIFWFSJMWQOA-UHFFFAOYSA-N n-(4-cyanophenyl)-1-[4-(dimethylamino)phenyl]methanimine oxide Chemical compound C1=CC(N(C)C)=CC=C1C=[N+]([O-])C1=CC=C(C#N)C=C1 ZFGIFWFSJMWQOA-UHFFFAOYSA-N 0.000 claims description 2
- 238000010422 painting Methods 0.000 claims description 2
- 238000004528 spin coating Methods 0.000 claims description 2
- 238000007592 spray painting technique Methods 0.000 claims description 2
- 125000006273 (C1-C3) alkyl group Chemical group 0.000 claims 2
- GRWDSSVTDTVMEV-UHFFFAOYSA-N 1-[4-(diethylamino)phenyl]-n-(4-ethoxycarbonylphenyl)methanimine oxide Chemical compound C1=CC(C(=O)OCC)=CC=C1[N+]([O-])=CC1=CC=C(N(CC)CC)C=C1 GRWDSSVTDTVMEV-UHFFFAOYSA-N 0.000 claims 2
- 239000004695 Polyether sulfone Substances 0.000 claims 2
- 239000004697 Polyetherimide Substances 0.000 claims 2
- 125000000896 monocarboxylic acid group Chemical group 0.000 claims 2
- IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical class C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 description 20
- 239000011230 binding agent Substances 0.000 description 13
- 229960001755 resorcinol Drugs 0.000 description 12
- GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 10
- 239000000126 substance Substances 0.000 description 10
- 125000001931 aliphatic group Chemical group 0.000 description 9
- 229930185605 Bisphenol Natural products 0.000 description 8
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 8
- 150000002009 diols Chemical class 0.000 description 8
- 150000001875 compounds Chemical class 0.000 description 7
- 230000008569 process Effects 0.000 description 7
- 150000003254 radicals Chemical class 0.000 description 7
- BVKZGUZCCUSVTD-UHFFFAOYSA-L Carbonate Chemical compound [O-]C([O-])=O BVKZGUZCCUSVTD-UHFFFAOYSA-L 0.000 description 6
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 6
- QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 6
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 description 6
- 239000006085 branching agent Substances 0.000 description 6
- QQVIHTHCMHWDBS-UHFFFAOYSA-N isophthalic acid Chemical compound OC(=O)C1=CC=CC(C(O)=O)=C1 QQVIHTHCMHWDBS-UHFFFAOYSA-N 0.000 description 6
- 238000006116 polymerization reaction Methods 0.000 description 6
- VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical compound C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 5
- 238000010521 absorption reaction Methods 0.000 description 5
- 229910052799 carbon Inorganic materials 0.000 description 5
- 239000003054 catalyst Substances 0.000 description 5
- 150000002430 hydrocarbons Chemical group 0.000 description 5
- 125000001183 hydrocarbyl group Chemical group 0.000 description 5
- 238000005259 measurement Methods 0.000 description 5
- 239000000178 monomer Substances 0.000 description 5
- 229920001225 polyester resin Polymers 0.000 description 5
- 239000004645 polyester resin Substances 0.000 description 5
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 4
- VYPSYNLAJGMNEJ-UHFFFAOYSA-N Silicium dioxide Chemical compound O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 4
- 125000004429 atom Chemical group 0.000 description 4
- 150000004650 carbonic acid diesters Chemical class 0.000 description 4
- 125000000113 cyclohexyl group Chemical group [H]C1([H])C([H])([H])C([H])([H])C([H])(*)C([H])([H])C1([H])[H] 0.000 description 4
- 230000003287 optical effect Effects 0.000 description 4
- 229920003229 poly(methyl methacrylate) Polymers 0.000 description 4
- 229920005644 polyethylene terephthalate glycol copolymer Polymers 0.000 description 4
- 239000002952 polymeric resin Substances 0.000 description 4
- 239000004926 polymethyl methacrylate Substances 0.000 description 4
- 229920003002 synthetic resin Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 229910003327 LiNbO3 Inorganic materials 0.000 description 3
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 238000003848 UV Light-Curing Methods 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000956 alloy Substances 0.000 description 3
- 229910045601 alloy Inorganic materials 0.000 description 3
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 3
- 238000012512 characterization method Methods 0.000 description 3
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 3
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 3
- ROORDVPLFPIABK-UHFFFAOYSA-N diphenyl carbonate Chemical compound C=1C=CC=CC=1OC(=O)OC1=CC=CC=C1 ROORDVPLFPIABK-UHFFFAOYSA-N 0.000 description 3
- 125000000623 heterocyclic group Chemical group 0.000 description 3
- 238000005984 hydrogenation reaction Methods 0.000 description 3
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
- 229920005668 polycarbonate resin Polymers 0.000 description 3
- 239000004431 polycarbonate resin Substances 0.000 description 3
- 238000002360 preparation method Methods 0.000 description 3
- YPFDHNVEDLHUCE-UHFFFAOYSA-N propane-1,3-diol Chemical compound OCCCO YPFDHNVEDLHUCE-UHFFFAOYSA-N 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- DYLIWHYUXAJDOJ-OWOJBTEDSA-N (e)-4-(6-aminopurin-9-yl)but-2-en-1-ol Chemical compound NC1=NC=NC2=C1N=CN2C\C=C\CO DYLIWHYUXAJDOJ-OWOJBTEDSA-N 0.000 description 2
- PXKLMJQFEQBVLD-UHFFFAOYSA-N Bisphenol F Natural products C1=CC(O)=CC=C1CC1=CC=C(O)C=C1 PXKLMJQFEQBVLD-UHFFFAOYSA-N 0.000 description 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 description 2
- 229920001634 Copolyester Polymers 0.000 description 2
- 239000004971 Cross linker Substances 0.000 description 2
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 2
- KDLHZDBZIXYQEI-UHFFFAOYSA-N Palladium Chemical compound [Pd] KDLHZDBZIXYQEI-UHFFFAOYSA-N 0.000 description 2
- ATUOYWHBWRKTHZ-UHFFFAOYSA-N Propane Chemical compound CCC ATUOYWHBWRKTHZ-UHFFFAOYSA-N 0.000 description 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N Succinic acid Natural products OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 2
- PNEYBMLMFCGWSK-UHFFFAOYSA-N aluminium oxide Inorganic materials [O-2].[O-2].[O-2].[Al+3].[Al+3] PNEYBMLMFCGWSK-UHFFFAOYSA-N 0.000 description 2
- 150000007860 aryl ester derivatives Chemical class 0.000 description 2
- QMKYBPDZANOJGF-UHFFFAOYSA-N benzene-1,3,5-tricarboxylic acid Chemical compound OC(=O)C1=CC(C(O)=O)=CC(C(O)=O)=C1 QMKYBPDZANOJGF-UHFFFAOYSA-N 0.000 description 2
- 239000004305 biphenyl Substances 0.000 description 2
- 235000010290 biphenyl Nutrition 0.000 description 2
- 229940106691 bisphenol a Drugs 0.000 description 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 description 2
- 229910052794 bromium Inorganic materials 0.000 description 2
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 2
- YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 238000001723 curing Methods 0.000 description 2
- 125000000753 cycloalkyl group Chemical group 0.000 description 2
- QYQADNCHXSEGJT-UHFFFAOYSA-N cyclohexane-1,1-dicarboxylate;hydron Chemical class OC(=O)C1(C(O)=O)CCCCC1 QYQADNCHXSEGJT-UHFFFAOYSA-N 0.000 description 2
- NNBZCPXTIHJBJL-UHFFFAOYSA-N decalin Chemical compound C1CCCC2CCCCC21 NNBZCPXTIHJBJL-UHFFFAOYSA-N 0.000 description 2
- 238000011161 development Methods 0.000 description 2
- 150000001991 dicarboxylic acids Chemical class 0.000 description 2
- LNGAGQAGYITKCW-UHFFFAOYSA-N dimethyl cyclohexane-1,4-dicarboxylate Chemical compound COC(=O)C1CCC(C(=O)OC)CC1 LNGAGQAGYITKCW-UHFFFAOYSA-N 0.000 description 2
- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
- TVIDDXQYHWJXFK-UHFFFAOYSA-N dodecanedioic acid Chemical compound OC(=O)CCCCCCCCCCC(O)=O TVIDDXQYHWJXFK-UHFFFAOYSA-N 0.000 description 2
- 239000011521 glass Substances 0.000 description 2
- 229910052736 halogen Chemical group 0.000 description 2
- 150000002367 halogens Chemical group 0.000 description 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 2
- 125000005027 hydroxyaryl group Chemical group 0.000 description 2
- 238000002347 injection Methods 0.000 description 2
- 239000007924 injection Substances 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- SLCVBVWXLSEKPL-UHFFFAOYSA-N neopentyl glycol Chemical compound OCC(C)(C)CO SLCVBVWXLSEKPL-UHFFFAOYSA-N 0.000 description 2
- YCWSUKQGVSGXJO-NTUHNPAUSA-N nifuroxazide Chemical group C1=CC(O)=CC=C1C(=O)N\N=C\C1=CC=C([N+]([O-])=O)O1 YCWSUKQGVSGXJO-NTUHNPAUSA-N 0.000 description 2
- BDJRBEYXGGNYIS-UHFFFAOYSA-N nonanedioic acid Chemical compound OC(=O)CCCCCCCC(O)=O BDJRBEYXGGNYIS-UHFFFAOYSA-N 0.000 description 2
- OIPPWFOQEKKFEE-UHFFFAOYSA-N orcinol Chemical compound CC1=CC(O)=CC(O)=C1 OIPPWFOQEKKFEE-UHFFFAOYSA-N 0.000 description 2
- PYXKIBGUDPZSBQ-UHFFFAOYSA-N phenol;3,5,5-trimethylcyclohex-2-en-1-one Chemical compound OC1=CC=CC=C1.OC1=CC=CC=C1.CC1=CC(=O)CC(C)(C)C1 PYXKIBGUDPZSBQ-UHFFFAOYSA-N 0.000 description 2
- 150000002989 phenols Chemical class 0.000 description 2
- 238000006349 photocyclization reaction Methods 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 229920001921 poly-methyl-phenyl-siloxane Polymers 0.000 description 2
- 229920001707 polybutylene terephthalate Polymers 0.000 description 2
- 238000006068 polycondensation reaction Methods 0.000 description 2
- 229920000139 polyethylene terephthalate Polymers 0.000 description 2
- 239000005020 polyethylene terephthalate Substances 0.000 description 2
- 229920005862 polyol Polymers 0.000 description 2
- 230000005855 radiation Effects 0.000 description 2
- 229920005989 resin Polymers 0.000 description 2
- 239000011347 resin Substances 0.000 description 2
- 229920006395 saturated elastomer Polymers 0.000 description 2
- 239000000377 silicon dioxide Substances 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 150000003462 sulfoxides Chemical class 0.000 description 2
- ARCGXLSVLAOJQL-UHFFFAOYSA-N trimellitic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 ARCGXLSVLAOJQL-UHFFFAOYSA-N 0.000 description 2
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- DNIAPMSPPWPWGF-VKHMYHEASA-N (+)-propylene glycol Chemical compound C[C@H](O)CO DNIAPMSPPWPWGF-VKHMYHEASA-N 0.000 description 1
- UXUFTKZYJYGMGO-CMCWBKRRSA-N (2s,3s,4r,5r)-5-[6-amino-2-[2-[4-[3-(2-aminoethylamino)-3-oxopropyl]phenyl]ethylamino]purin-9-yl]-n-ethyl-3,4-dihydroxyoxolane-2-carboxamide Chemical compound O[C@@H]1[C@H](O)[C@@H](C(=O)NCC)O[C@H]1N1C2=NC(NCCC=3C=CC(CCC(=O)NCCN)=CC=3)=NC(N)=C2N=C1 UXUFTKZYJYGMGO-CMCWBKRRSA-N 0.000 description 1
- GPFJHNSSBHPYJK-UHFFFAOYSA-N (3-methylphenyl) hydrogen carbonate Chemical compound CC1=CC=CC(OC(O)=O)=C1 GPFJHNSSBHPYJK-UHFFFAOYSA-N 0.000 description 1
- HCNHNBLSNVSJTJ-UHFFFAOYSA-N 1,1-Bis(4-hydroxyphenyl)ethane Chemical compound C=1C=C(O)C=CC=1C(C)C1=CC=C(O)C=C1 HCNHNBLSNVSJTJ-UHFFFAOYSA-N 0.000 description 1
- YBMDPYAEZDJWNY-UHFFFAOYSA-N 1,2,3,3,4,4,5,5-octafluorocyclopentene Chemical class FC1=C(F)C(F)(F)C(F)(F)C1(F)F YBMDPYAEZDJWNY-UHFFFAOYSA-N 0.000 description 1
- 150000005207 1,3-dihydroxybenzenes Chemical class 0.000 description 1
- 229940035437 1,3-propanediol Drugs 0.000 description 1
- PXGZQGDTEZPERC-UHFFFAOYSA-N 1,4-cyclohexanedicarboxylic acid Chemical compound OC(=O)C1CCC(C(O)=O)CC1 PXGZQGDTEZPERC-UHFFFAOYSA-N 0.000 description 1
- 150000005208 1,4-dihydroxybenzenes Chemical class 0.000 description 1
- 229940043375 1,5-pentanediol Drugs 0.000 description 1
- LNETULKMXZVUST-UHFFFAOYSA-N 1-naphthoic acid Chemical compound C1=CC=C2C(C(=O)O)=CC=CC2=C1 LNETULKMXZVUST-UHFFFAOYSA-N 0.000 description 1
- KLZYRCVPDWTZLH-UHFFFAOYSA-N 2,3-dimethylsuccinic acid Chemical compound OC(=O)C(C)C(C)C(O)=O KLZYRCVPDWTZLH-UHFFFAOYSA-N 0.000 description 1
- LUELYTMQTXRXOI-UHFFFAOYSA-N 2-(2-phenylpropan-2-yl)benzene-1,4-diol Chemical compound C=1C(O)=CC=C(O)C=1C(C)(C)C1=CC=CC=C1 LUELYTMQTXRXOI-UHFFFAOYSA-N 0.000 description 1
- XRCRJFOGPCJKPF-UHFFFAOYSA-N 2-butylbenzene-1,4-diol Chemical compound CCCCC1=CC(O)=CC=C1O XRCRJFOGPCJKPF-UHFFFAOYSA-N 0.000 description 1
- KTXWGMUMDPYXNN-UHFFFAOYSA-N 2-ethylhexan-1-olate;titanium(4+) Chemical compound [Ti+4].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-].CCCCC(CC)C[O-] KTXWGMUMDPYXNN-UHFFFAOYSA-N 0.000 description 1
- AAAWJUMVTPNRDT-UHFFFAOYSA-N 2-methylpentane-1,5-diol Chemical compound OCC(C)CCCO AAAWJUMVTPNRDT-UHFFFAOYSA-N 0.000 description 1
- XCZKKZXWDBOGPA-UHFFFAOYSA-N 2-phenylbenzene-1,4-diol Chemical compound OC1=CC=C(O)C(C=2C=CC=CC=2)=C1 XCZKKZXWDBOGPA-UHFFFAOYSA-N 0.000 description 1
- NJRNUAVVFBHIPT-UHFFFAOYSA-N 2-propylbenzene-1,4-diol Chemical compound CCCC1=CC(O)=CC=C1O NJRNUAVVFBHIPT-UHFFFAOYSA-N 0.000 description 1
- CKNCVRMXCLUOJI-UHFFFAOYSA-N 3,3'-dibromobisphenol A Chemical compound C=1C=C(O)C(Br)=CC=1C(C)(C)C1=CC=C(O)C(Br)=C1 CKNCVRMXCLUOJI-UHFFFAOYSA-N 0.000 description 1
- GXDIDDARPBFKNG-UHFFFAOYSA-N 4,4'-(Butane-1,1-diyl)diphenol Chemical compound C=1C=C(O)C=CC=1C(CCC)C1=CC=C(O)C=C1 GXDIDDARPBFKNG-UHFFFAOYSA-N 0.000 description 1
- VWGKEVWFBOUAND-UHFFFAOYSA-N 4,4'-thiodiphenol Chemical compound C1=CC(O)=CC=C1SC1=CC=C(O)C=C1 VWGKEVWFBOUAND-UHFFFAOYSA-N 0.000 description 1
- UITKHKNFVCYWNG-UHFFFAOYSA-N 4-(3,4-dicarboxybenzoyl)phthalic acid Chemical compound C1=C(C(O)=O)C(C(=O)O)=CC=C1C(=O)C1=CC=C(C(O)=O)C(C(O)=O)=C1 UITKHKNFVCYWNG-UHFFFAOYSA-N 0.000 description 1
- WVDRSXGPQWNUBN-UHFFFAOYSA-N 4-(4-carboxyphenoxy)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1OC1=CC=C(C(O)=O)C=C1 WVDRSXGPQWNUBN-UHFFFAOYSA-N 0.000 description 1
- NEQFBGHQPUXOFH-UHFFFAOYSA-N 4-(4-carboxyphenyl)benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1C1=CC=C(C(O)=O)C=C1 NEQFBGHQPUXOFH-UHFFFAOYSA-N 0.000 description 1
- NZGQHKSLKRFZFL-UHFFFAOYSA-N 4-(4-hydroxyphenoxy)phenol Chemical compound C1=CC(O)=CC=C1OC1=CC=C(O)C=C1 NZGQHKSLKRFZFL-UHFFFAOYSA-N 0.000 description 1
- RSSGMIIGVQRGDS-UHFFFAOYSA-N 4-[(4-hydroxyphenyl)-phenylmethyl]phenol Chemical compound C1=CC(O)=CC=C1C(C=1C=CC(O)=CC=1)C1=CC=CC=C1 RSSGMIIGVQRGDS-UHFFFAOYSA-N 0.000 description 1
- OVVCSFQRAXVPGT-UHFFFAOYSA-N 4-[1-(4-hydroxyphenyl)cyclopentyl]phenol Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)CCCC1 OVVCSFQRAXVPGT-UHFFFAOYSA-N 0.000 description 1
- HCUNREWMFYCWAQ-UHFFFAOYSA-N 4-[2-(4-carboxyphenyl)ethyl]benzoic acid Chemical compound C1=CC(C(=O)O)=CC=C1CCC1=CC=C(C(O)=O)C=C1 HCUNREWMFYCWAQ-UHFFFAOYSA-N 0.000 description 1
- YTRKBSVUOQIJOR-UHFFFAOYSA-N 4-[2-(4-hydroxy-1-methylcyclohexa-2,4-dien-1-yl)propan-2-yl]-4-methylcyclohexa-1,5-dien-1-ol Chemical compound C1C=C(O)C=CC1(C)C(C)(C)C1(C)CC=C(O)C=C1 YTRKBSVUOQIJOR-UHFFFAOYSA-N 0.000 description 1
- QHJPJZROUNGTRJ-UHFFFAOYSA-N 4-[2-(4-hydroxyphenyl)octan-2-yl]phenol Chemical compound C=1C=C(O)C=CC=1C(C)(CCCCCC)C1=CC=C(O)C=C1 QHJPJZROUNGTRJ-UHFFFAOYSA-N 0.000 description 1
- XOIZPYZCDNKYBW-UHFFFAOYSA-N 5-tert-butylbenzene-1,3-diol Chemical compound CC(C)(C)C1=CC(O)=CC(O)=C1 XOIZPYZCDNKYBW-UHFFFAOYSA-N 0.000 description 1
- HTVITOHKHWFJKO-UHFFFAOYSA-N Bisphenol B Chemical compound C=1C=C(O)C=CC=1C(C)(CC)C1=CC=C(O)C=C1 HTVITOHKHWFJKO-UHFFFAOYSA-N 0.000 description 1
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 1
- XDTMQSROBMDMFD-UHFFFAOYSA-N Cyclohexane Chemical compound C1CCCCC1 XDTMQSROBMDMFD-UHFFFAOYSA-N 0.000 description 1
- OIFBSDVPJOWBCH-UHFFFAOYSA-N Diethyl carbonate Chemical compound CCOC(=O)OCC OIFBSDVPJOWBCH-UHFFFAOYSA-N 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- CTQNGGLPUBDAKN-UHFFFAOYSA-N O-Xylene Chemical compound CC1=CC=CC=C1C CTQNGGLPUBDAKN-UHFFFAOYSA-N 0.000 description 1
- PXGZQGDTEZPERC-IZLXSQMJSA-N OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 Chemical class OC(=O)[C@H]1CC[C@H](C(O)=O)CC1 PXGZQGDTEZPERC-IZLXSQMJSA-N 0.000 description 1
- ALQSHHUCVQOPAS-UHFFFAOYSA-N Pentane-1,5-diol Chemical compound OCCCCCO ALQSHHUCVQOPAS-UHFFFAOYSA-N 0.000 description 1
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical compound [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 description 1
- KZTYYGOKRVBIMI-UHFFFAOYSA-N S-phenyl benzenesulfonothioate Natural products C=1C=CC=CC=1S(=O)(=O)C1=CC=CC=C1 KZTYYGOKRVBIMI-UHFFFAOYSA-N 0.000 description 1
- BGNXCDMCOKJUMV-UHFFFAOYSA-N Tert-Butylhydroquinone Chemical compound CC(C)(C)C1=CC(O)=CC=C1O BGNXCDMCOKJUMV-UHFFFAOYSA-N 0.000 description 1
- YTPLMLYBLZKORZ-UHFFFAOYSA-N Thiophene Chemical group C=1C=CSC=1 YTPLMLYBLZKORZ-UHFFFAOYSA-N 0.000 description 1
- RTAQQCXQSZGOHL-UHFFFAOYSA-N Titanium Chemical compound [Ti] RTAQQCXQSZGOHL-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- YIMQCDZDWXUDCA-UHFFFAOYSA-N [4-(hydroxymethyl)cyclohexyl]methanol Chemical compound OCC1CCC(CO)CC1 YIMQCDZDWXUDCA-UHFFFAOYSA-N 0.000 description 1
- 238000000862 absorption spectrum Methods 0.000 description 1
- 239000001361 adipic acid Substances 0.000 description 1
- 235000011037 adipic acid Nutrition 0.000 description 1
- 125000002723 alicyclic group Chemical group 0.000 description 1
- 125000005907 alkyl ester group Chemical group 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 150000005840 aryl radicals Chemical class 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000002619 bicyclic group Chemical group 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- JOJNCSKBTSMKKW-UHFFFAOYSA-N bis(2,4,6-trichlorophenyl) carbonate Chemical compound ClC1=CC(Cl)=CC(Cl)=C1OC(=O)OC1=C(Cl)C=C(Cl)C=C1Cl JOJNCSKBTSMKKW-UHFFFAOYSA-N 0.000 description 1
- HBLSZXRYFSCREB-UHFFFAOYSA-N bis(2,4-dichlorophenyl) carbonate Chemical compound ClC1=CC(Cl)=CC=C1OC(=O)OC1=CC=C(Cl)C=C1Cl HBLSZXRYFSCREB-UHFFFAOYSA-N 0.000 description 1
- DEVXPGMBRTYKHS-UHFFFAOYSA-N bis(2-cyanophenyl) carbonate Chemical compound C=1C=CC=C(C#N)C=1OC(=O)OC1=CC=CC=C1C#N DEVXPGMBRTYKHS-UHFFFAOYSA-N 0.000 description 1
- POZGCGJFBOZPCM-UHFFFAOYSA-N bis(2-methylphenyl) carbonate Chemical compound CC1=CC=CC=C1OC(=O)OC1=CC=CC=C1C POZGCGJFBOZPCM-UHFFFAOYSA-N 0.000 description 1
- DQPSUGZZTADITQ-UHFFFAOYSA-N bis(2-nitrophenyl) carbonate Chemical compound [O-][N+](=O)C1=CC=CC=C1OC(=O)OC1=CC=CC=C1[N+]([O-])=O DQPSUGZZTADITQ-UHFFFAOYSA-N 0.000 description 1
- 230000000903 blocking effect Effects 0.000 description 1
- 150000001649 bromium compounds Chemical class 0.000 description 1
- CDQSJQSWAWPGKG-UHFFFAOYSA-N butane-1,1-diol Chemical compound CCCC(O)O CDQSJQSWAWPGKG-UHFFFAOYSA-N 0.000 description 1
- KDYFGRWQOYBRFD-NUQCWPJISA-N butanedioic acid Chemical compound O[14C](=O)CC[14C](O)=O KDYFGRWQOYBRFD-NUQCWPJISA-N 0.000 description 1
- 150000001721 carbon Chemical class 0.000 description 1
- MOIPGXQKZSZOQX-UHFFFAOYSA-N carbonyl bromide Chemical compound BrC(Br)=O MOIPGXQKZSZOQX-UHFFFAOYSA-N 0.000 description 1
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 1
- 150000001244 carboxylic acid anhydrides Chemical class 0.000 description 1
- 125000002843 carboxylic acid group Chemical group 0.000 description 1
- 150000001735 carboxylic acids Chemical class 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 230000008859 change Effects 0.000 description 1
- 239000007795 chemical reaction product Substances 0.000 description 1
- 239000000460 chlorine Substances 0.000 description 1
- 229910052801 chlorine Inorganic materials 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 238000009833 condensation Methods 0.000 description 1
- 230000005494 condensation Effects 0.000 description 1
- 230000021615 conjugation Effects 0.000 description 1
- 238000002425 crystallisation Methods 0.000 description 1
- 230000008025 crystallization Effects 0.000 description 1
- 125000004122 cyclic group Chemical group 0.000 description 1
- 150000001925 cycloalkenes Chemical group 0.000 description 1
- NLUNLVTVUDIHFE-UHFFFAOYSA-N cyclooctylcyclooctane Chemical compound C1CCCCCCC1C1CCCCCCC1 NLUNLVTVUDIHFE-UHFFFAOYSA-N 0.000 description 1
- FOTKYAAJKYLFFN-UHFFFAOYSA-N decane-1,10-diol Chemical compound OCCCCCCCCCCO FOTKYAAJKYLFFN-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 125000004663 dialkyl amino group Chemical group 0.000 description 1
- QLVWOKQMDLQXNN-UHFFFAOYSA-N dibutyl carbonate Chemical compound CCCCOC(=O)OCCCC QLVWOKQMDLQXNN-UHFFFAOYSA-N 0.000 description 1
- FYIBPWZEZWVDQB-UHFFFAOYSA-N dicyclohexyl carbonate Chemical compound C1CCCCC1OC(=O)OC1CCCCC1 FYIBPWZEZWVDQB-UHFFFAOYSA-N 0.000 description 1
- IEJIGPNLZYLLBP-UHFFFAOYSA-N dimethyl carbonate Chemical compound COC(=O)OC IEJIGPNLZYLLBP-UHFFFAOYSA-N 0.000 description 1
- ZQUZPFYNEARCQO-UHFFFAOYSA-N dinaphthalen-1-yl carbonate Chemical compound C1=CC=C2C(OC(OC=3C4=CC=CC=C4C=CC=3)=O)=CC=CC2=C1 ZQUZPFYNEARCQO-UHFFFAOYSA-N 0.000 description 1
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 1
- 238000004821 distillation Methods 0.000 description 1
- FRNQLQRBNSSJBK-UHFFFAOYSA-N divarinol Natural products CCCC1=CC(O)=CC(O)=C1 FRNQLQRBNSSJBK-UHFFFAOYSA-N 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- BITPLIXHRASDQB-UHFFFAOYSA-N ethenyl-[ethenyl(dimethyl)silyl]oxy-dimethylsilane Chemical compound C=C[Si](C)(C)O[Si](C)(C)C=C BITPLIXHRASDQB-UHFFFAOYSA-N 0.000 description 1
- 150000002170 ethers Chemical class 0.000 description 1
- 239000000945 filler Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 125000000524 functional group Chemical group 0.000 description 1
- ZZUFCTLCJUWOSV-UHFFFAOYSA-N furosemide Chemical compound C1=C(Cl)C(S(=O)(=O)N)=CC(C(O)=O)=C1NCC1=CC=CO1 ZZUFCTLCJUWOSV-UHFFFAOYSA-N 0.000 description 1
- 230000009477 glass transition Effects 0.000 description 1
- 150000002334 glycols Chemical class 0.000 description 1
- 125000005067 haloformyl group Chemical group 0.000 description 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 1
- 239000008240 homogeneous mixture Substances 0.000 description 1
- 229920001519 homopolymer Polymers 0.000 description 1
- 150000001261 hydroxy acids Chemical class 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 238000011065 in-situ storage Methods 0.000 description 1
- 239000003999 initiator Substances 0.000 description 1
- 238000010406 interfacial reaction Methods 0.000 description 1
- PNDPGZBMCMUPRI-UHFFFAOYSA-N iodine Chemical compound II PNDPGZBMCMUPRI-UHFFFAOYSA-N 0.000 description 1
- HJOVHMDZYOCNQW-UHFFFAOYSA-N isophorone Chemical class CC1=CC(=O)CC(C)(C)C1 HJOVHMDZYOCNQW-UHFFFAOYSA-N 0.000 description 1
- 125000000654 isopropylidene group Chemical group C(C)(C)=* 0.000 description 1
- GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical class O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 1
- 125000005439 maleimidyl group Chemical class C1(C=CC(N1*)=O)=O 0.000 description 1
- 238000011177 media preparation Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- OJURWUUOVGOHJZ-UHFFFAOYSA-N methyl 2-[(2-acetyloxyphenyl)methyl-[2-[(2-acetyloxyphenyl)methyl-(2-methoxy-2-oxoethyl)amino]ethyl]amino]acetate Chemical compound C=1C=CC=C(OC(C)=O)C=1CN(CC(=O)OC)CCN(CC(=O)OC)CC1=CC=CC=C1OC(C)=O OJURWUUOVGOHJZ-UHFFFAOYSA-N 0.000 description 1
- 125000002950 monocyclic group Chemical group 0.000 description 1
- SYSQUGFVNFXIIT-UHFFFAOYSA-N n-[4-(1,3-benzoxazol-2-yl)phenyl]-4-nitrobenzenesulfonamide Chemical class C1=CC([N+](=O)[O-])=CC=C1S(=O)(=O)NC1=CC=C(C=2OC3=CC=CC=C3N=2)C=C1 SYSQUGFVNFXIIT-UHFFFAOYSA-N 0.000 description 1
- KYTZHLUVELPASH-UHFFFAOYSA-N naphthalene-1,2-dicarboxylic acid Chemical compound C1=CC=CC2=C(C(O)=O)C(C(=O)O)=CC=C21 KYTZHLUVELPASH-UHFFFAOYSA-N 0.000 description 1
- RXOHFPCZGPKIRD-UHFFFAOYSA-N naphthalene-2,6-dicarboxylic acid Chemical class C1=C(C(O)=O)C=CC2=CC(C(=O)O)=CC=C21 RXOHFPCZGPKIRD-UHFFFAOYSA-N 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- SJDACOMXKWHBOW-UHFFFAOYSA-N oxyphenisatine Chemical compound C1=CC(O)=CC=C1C1(C=2C=CC(O)=CC=2)C2=CC=CC=C2NC1=O SJDACOMXKWHBOW-UHFFFAOYSA-N 0.000 description 1
- 229910052763 palladium Inorganic materials 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 229910052697 platinum Inorganic materials 0.000 description 1
- 230000010287 polarization Effects 0.000 description 1
- 229920000647 polyepoxide Polymers 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 235000013824 polyphenols Nutrition 0.000 description 1
- 229920000166 polytrimethylene carbonate Polymers 0.000 description 1
- 239000001294 propane Substances 0.000 description 1
- 238000006862 quantum yield reaction Methods 0.000 description 1
- 230000010076 replication Effects 0.000 description 1
- 230000002441 reversible effect Effects 0.000 description 1
- 229910052703 rhodium Inorganic materials 0.000 description 1
- 239000010948 rhodium Substances 0.000 description 1
- MHOVAHRLVXNVSD-UHFFFAOYSA-N rhodium atom Chemical compound [Rh] MHOVAHRLVXNVSD-UHFFFAOYSA-N 0.000 description 1
- 229910052707 ruthenium Inorganic materials 0.000 description 1
- 229930195734 saturated hydrocarbon Natural products 0.000 description 1
- 230000035945 sensitivity Effects 0.000 description 1
- 125000006850 spacer group Chemical group 0.000 description 1
- 230000003595 spectral effect Effects 0.000 description 1
- 239000000758 substrate Substances 0.000 description 1
- 150000003457 sulfones Chemical class 0.000 description 1
- 239000004416 thermosoftening plastic Substances 0.000 description 1
- 150000003568 thioethers Chemical class 0.000 description 1
- 229910052719 titanium Inorganic materials 0.000 description 1
- 239000010936 titanium Substances 0.000 description 1
- CNHDIAIOKMXOLK-UHFFFAOYSA-N toluquinol Chemical compound CC1=CC(O)=CC=C1O CNHDIAIOKMXOLK-UHFFFAOYSA-N 0.000 description 1
- 230000017105 transposition Effects 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical compound OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- SRPWOOOHEPICQU-UHFFFAOYSA-N trimellitic anhydride Chemical compound OC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 SRPWOOOHEPICQU-UHFFFAOYSA-N 0.000 description 1
- NJMOHBDCGXJLNJ-UHFFFAOYSA-N trimellitic anhydride chloride Chemical compound ClC(=O)C1=CC=C2C(=O)OC(=O)C2=C1 NJMOHBDCGXJLNJ-UHFFFAOYSA-N 0.000 description 1
- 229910052724 xenon Inorganic materials 0.000 description 1
- FHNFHKCVQCLJFQ-UHFFFAOYSA-N xenon atom Chemical compound [Xe] FHNFHKCVQCLJFQ-UHFFFAOYSA-N 0.000 description 1
- 239000008096 xylene Substances 0.000 description 1
Classifications
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/245—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing a polymeric component
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
-
- G—PHYSICS
- G11—INFORMATION STORAGE
- G11B—INFORMATION STORAGE BASED ON RELATIVE MOVEMENT BETWEEN RECORD CARRIER AND TRANSDUCER
- G11B7/00—Recording or reproducing by optical means, e.g. recording using a thermal beam of optical radiation by modifying optical properties or the physical structure, reproducing using an optical beam at lower power by sensing optical properties; Record carriers therefor
- G11B7/24—Record carriers characterised by shape, structure or physical properties, or by the selection of the material
- G11B7/241—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material
- G11B7/242—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers
- G11B7/244—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only
- G11B7/246—Record carriers characterised by shape, structure or physical properties, or by the selection of the material characterised by the selection of the material of recording layers comprising organic materials only containing dyes
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H1/00—Holographic processes or apparatus using light, infrared or ultraviolet waves for obtaining holograms or for obtaining an image from them; Details peculiar thereto
- G03H1/02—Details of features involved during the holographic process; Replication of holograms without interference recording
- G03H2001/026—Recording materials or recording processes
- G03H2001/0264—Organic recording material
Definitions
- the present disclosure relates to optical data storage media, and more particularly, to holographic storage mediums as well as methods of making and using the same.
- Holographic storage is the data storage of holograms, which are images of three dimensional interference patterns created by the intersection of two beams of light, in a photosensitive medium.
- the superposition of a reference beam and a signal beam, containing digitally encoded data, forms an interference pattern within the volume of the medium resulting in a chemical reaction that changes or modulates the refractive index of the medium. This modulation serves to record as the hologram both the intensity and phase information from the signal.
- the hologram can later be retrieved by exposing the storage medium to the reference beam alone, which interacts with the stored holographic data to generate a reconstructed signal beam proportional to the initial signal beam used to store the holographic image.
- Each hologram may contain anywhere from one to IxIO ⁇ or more bits of data.
- One distinct advantage of holographic storage over surface-based storage formats, including CDs or DVDs, is that a large number of holograms may be stored in an overlapping manner in the same volume of the photosensitive medium using a multiplexing technique, such as by varying the signal and/or reference beam angle, wavelength, or medium position.
- a major impediment towards the realization of holographic storage as a viable technique has been the development of a reliable and economically feasible storage medium.
- LiNbO 3 doped or undoped lithium niobate
- incident light creates refractive index changes.
- These index changes are due to the photo-induced creation and subsequent trapping of electrons leading to an induced internal electric field that ultimately modifies the index through a linear electro-optic effect.
- LiNbO 3 is expensive, exhibits relatively poor efficiency, fades over time, and requires thick crystals to observe any significant index changes. More recent work has led to the development of polymers that can sustain larger refractive index changes owing to optically induced polymerization processes.
- photopolymers have significantly improved optical sensitivity and efficiency relative to LiNbO 3 and its variants.
- single-chemistry systems have been employed, wherein the media comprise a homogeneous mixture of at least one photoactive polymerizable liquid monomer or oligomer, an initiator, an inert polymeric filler, and optionally a sensitizer. Since it initially has a large fraction of the mixture in monomeric or oligomeric form, the medium may have a gel-like consistency that necessitates an ultraviolet (UV) curing step to provide form and stability.
- UV ultraviolet
- the UV curing step may consume a large portion of the photoactive monomer or oligomer, leaving significantly less photoactive monomer or oligomer available for data storage. Furthermore, even under highly controlled curing conditions, the UV curing step may often result in variable degrees of polymerization and, consequently, poor uniformity among media samples.
- Disclosed herein is a method of manufacturing a data storage media comprising mixing a photochromic dye with an organic material or an inorganic material to form a holographic composition; and molding the holographic composition into holographic data storage media.
- an article comprising a photochromic dye and an organic material, wherein the article is used as a data storage media.
- a method for recording information comprising irradiating an article that comprises a photochromic dye; wherein the irradiation is conducted with electromagnetic energy having a wavelength of about 350 to about 1 ,100 nanometers; and reacting the photochromic dye.
- a method for using a holographic data storage media comprising irradiating an article that comprises a photochromic dye; wherein the irradiation is conducted with electromagnetic energy having a first wavelength and wherein the irradiating that is conducted at the first wavelength facilitates the storage of data; reacting the photochromic dye; and irradiating the article at a second wavelength to read the data.
- a method of manufacturing a holographic data storage media comprising disposing a layer of a photoactive material upon a surface of a first film; wherein the photoactive material comprises a photochromic dye; and disposing a second film upon a surface of the photoactive material opposed to the surface in contact with the first film.
- Figure 1 is a schematic representation of a holographic storage setup for (a) writing data and (b) reading stored data;
- Figure 2 is a schematic representation of a diffraction efficiency characterization setup for (a) writing plane wave holograms and (b) measuring diffracted light;
- Figure 3 is a schematic representation of a holographic plane-wave characterization system.
- optical data storage media for use in holographic data storage and retrieval. Also disclosed are methods directed to holographic storage media preparation, data storage, and data retrieval.
- the holographic storage media is manufactured from a holographic composition that comprises a binder composition and a photoactive material, wherein the photoactive material comprises a photochromic dye.
- the photochromic dye comprises a diarylethene, a nitrone, or a combination of a diarylethene and a nitrone.
- the holographic storage media can be advantageously used for data storage.
- the holographic storage media can also be written and read (i.e., data can be stored and retrieved respectively) using electromagnetic radiation having the same wavelength.
- the binder composition can comprise an inorganic material, an organic material or a combination of an inorganic material with an organic material.
- suitable inorganic materials are silica (glass), alumina, or the like, or a combination comprising at least one of the foregoing inorganic materials.
- Exemplary organic materials employed in the binder composition are optically transparent organic polymers.
- the organic polymer can be a thermoplastic polymer, a thermosetting polymer, or a combination of a thermoplastic polymer with a thermosetting polymer.
- the organic polymers can be oligomers, polymers, dendrimers, ionomers, copolymers such as for example, block copolymers, random copolymers, graft copolymers, star block copolymers; or the like, or a combination comprising at least one of the foregoing polymers.
- Organic polymers that are not transparent to electromagnetic radiation can also be used in the binder composition if they can be modified to become transparent.
- polyolefins are not normally optically transparent because of the presence of large crystallites and/or spherulites. However, by copolymerizing polyolefins, they can be segregated into nanometer-sized domains that cause the copolymer to be optically transparent.
- the organic polymer can be chemically attached to the photochromic dye.
- the photochroniic dye can be attached to the backbone of the polymer.
- the photochromic dye can be attached to the polymer backbone as a substituent.
- the chemical attachment can include covalent bonding, ionic bonding, or the like.
- Suitable organic polymers for use in the binder composition of the data storage devices are polycarbonates, cycloaliphatic polyesters, resorcinol arylate polyesters, as well as blends and copolymers of polycarbonates with polyesters.
- polycarbonate includes compositions having structural units of the formula (1):
- R 1 is an aromatic organic radical and, more preferably, a radical of the formula (II):
- each of A 1 and A 2 is a monocyclic divalent aryl radical and Y 1 is a bridging radical having zero, one, or two atoms which separate A 1 from A 2 .
- one atom separates A 1 from A 2 .
- radicals of this type are -O-, -S-, -S(O)-, -S(0) 2 -, -C(O)-, methylene, cyclohexyl-methylene, 2-[2,2,l]-bicycloheptylidene, ethylidene, isopropylidene, neopentylidene, cyclohexylidene, cyclopentadecylidene, cyclododecylidene, adamantylidene, or the like.
- zero atoms separate A 1 from A 2 , with an illustrative example being biphenyl.
- the bridging radical Y 1 can be a saturated hydrocarbon group such as methylene, cyclohexylidene or isopropylidene.
- Polycarbonates can be produced by the interfacial or melt reactions of dihydroxy compounds in which only one atom separates A and A 2 .
- dihydroxy compound includes, for example, bisphenol compounds having general formula (III) as follows:
- R a and R b each independently represent hydrogen, a halogen atom, preferably bromine, or a monovalent hydrocarbon group; p and q are each independently integers from 0 to 4; and X a represents one of the groups of formula (IV):
- R c and R d each independently represent a hydrogen atom or a monovalent linear or cyclic hydrocarbon group, and R e is a divalent hydrocarbon group, oxygen, or sulfur.
- Examples of the types of bisphenol compounds that may be represented by formula (III) include the bis(hydroxyaryl)alkane series such as, 1 , 1 -bis(4- hydroxyphenyl)methane, 1 ,1 -bis(4-hydroxyphenyl)ethane, 2,2-bis(4- hydroxyphenyl)propane (or bisphenol-A), 2,2-bis(4-hydroxyphenyl)butane, 2,2-bis(4- hydroxyphenyl)octane, 1 , 1 -bis(4-hydroxyplienyl)propane, 1 , 1 -bis(4- hydroxyphenyl)n-butane, bis(4-hydroxyphenyl)phenylmethane, 2,2-bis(4-hydroxy-l - methylphenyl)propane, 1 ,1 -bis(4-hydroxy-t-butylprienyl)piOpane, 2,2-bis(4-hydroxy- 3-bromophenyl)propane, or
- bisphenol compounds that may be represented by formula (III) include those where X is -O-, -S-, -SO- or -S(O) 2 -.
- Some examples of such bisphenol compounds are bis(hydroxyaryl)ethers such as 4,4'-dihydroxy diphenylether, 4,4'-dihydroxy-3,3'- dimethylphenyl ether, or the like; bis(hydroxy diaryl)sulfides, such as 4,4'-dihydroxy diphenyl sulfide, 4,4'-dihydroxy-3,3'-dimethyl diphenyl sulfide, or the like; bis(hydroxy diaryl) sulfoxides, such as, 4,4'-dihydroxy diphenyd sulfoxides, 4,4'- dihydroxy-3,3'-dimethyl diphenyl sulfoxides, or the like; bis(hydro:xy diaryl)sulfones, such as 4,4'-dihydroxy diphenyl sulfone,
- R f is a halogen atom or a hydrocarbon group having 1 to 10 carbon atoms or a halogen substituted hydrocarbon group; n is a value from 0 to 4. When n is at least 2, R f may be the same or different.
- bisphenol compounds that may be represented by the formula (V), are resorcinol, substituted resorcinol compounds such as 5-methyl resorcin, 5-ethyl resorcin, 5-propyl resorcin, 5-butyl resorcin, 5-t-butyl resorcin, 5-phenyl resorcin, 5-cumyl resorcin, or the like; catechol, hydroquinone, substituted hydroquinones, such as 3-methyl hydroquinone, 3-ethy ⁇ l hydroquinone, 3- propyl hydroquinone, 3-butyl hydroquinone, 3-t-butyl hydroquinone, 3-phenyl hydroquinone, 3-cumyl hydroquinone, or the like; or combinations comprising at least one of the foregoing bisphenol compounds.
- substituted resorcinol compounds such as 5-methyl resorcin, 5-ethyl resorcin, 5-propyl
- Bisphenol compounds such as 2,2, 2', T- tetrahydro-3, 3, 3', 3'- tetramethyl-1, 1 '- spirobiindane-6, 6'- diol represented by the following formula (VI) may also be used.
- Suitable polycarbonates further include those derived from bisphenols containing alkyl cyclohexane units. Such polycarbonates have structural units corresponding to the formula (VII)
- R a -R d are each independently hydrogen, C J -C I 2 hydrocarbyl, or halogen; and R e -R' are each independently hydrogen, C]-Ci 2 hydrocarbyl.
- hydrocarbyl refers to a residue that contains only carbon and hydrogen. The residue may be aliphatic or aromatic, straight-chain, cyclic, bicyclic, branched, saturated, or unsaturated. The hydrocarbyl residue may contain heteroatoms over and above the carbon and hydrogen members of the substituent residue.
- the hydrocarbyl residue may also contain carbonyl groups, amino groups, hydroxyl groups, or the like, or it may contain heteroatoms within the backbone of the hydrocarbyl residue.
- Alkyl cyclohexane containing bisphenols for example the reaction product of two moles of a phenol with one mole of a hydrogenated isophorone, are useful for making polycarbonate resins with high glass transition temperatures and high heat distortion temperatures.
- isophorone bisphenol-containing polycarbonates have structural units corresponding to the formula (VIII)
- R a -R d are as defined above.
- isophorone bisphenol based resins including polycarbonate copolymers made containing non-alkyl cyclohexane bisphenols and blends of alkyl cyclohexyl bisphenol containing polycarbonates with non-alkyl cyclohexyl bisphenol polycarbonates, are supplied by Bayer Co. under the APEC trade name.
- the preferred bisphenol compound is bisphenol A.
- Typical carbonate precursors include the carbonyl halides, for example carbonyl chloride (phosgene), and carbonyl bromide; the bis-haloformates, for example the bis- haloformates of dihydric phenols such as bisphenol A, hydroquinone, or the like, and the bis-haloformates of glycols such as ethylene glycol and neopentyl glycol; and the diaryl carbonates, such as diphenyl carbonate, di(tolyl) carbonate, and di(naphthyl) carbonate.
- the preferred carbonate precursor for the interfacial reaction is carbonyl chloride.
- polycarbonates resulting from the polymerization of two or more different dihydric phenols or a copolymer of a dihydric phenol with a glycol or with a hydroxy- or acid-terminated polyester or with a dibasic acid or with a hydroxy acid or with an aliphatic diacid in the event a carbonate copolymer rather than a homopolymer is desired for use.
- useful aliphatic diacids have about 2 to about 40 carbons.
- a preferred aliphatic diacid is dodecanedioic acid.
- Branched polycarbonates as well as blends of linear polycarbonate and a branched polycarbonate may also be used in the data storage device.
- the branched polycarbonates may be prepared by adding a branching agent during polymerization.
- branching agents may comprise polyfunctional organic compounds containing at least three functional groups, which may be hydroxyl, carboxyl, carboxylic anhydride, haloformyl, or combinations comprising at least one of the foregoing branching agents.
- branching agents examples include trimellitic acid, trimellitic anhydride, trimellitic trichloride, tris-p-hydroxy phenyl ethane, isatin-bis- phenol, tris-phenol TC (l ,3,5-tris((p-hydroxyphenyl)isopropyl)benzene), tris-phenol PA (4(4(1, l-bis(p-hydroxyphenyl)-ethyl) ⁇ , ⁇ -dimethyl benzyl)phenol), 4- chloroformyl phthalic anhydride, trimesic acid, benzophenone tetracarboxylic acid, or the like, or combinations comprising at least one of the foregoing branching agents.
- the branching agents may be added at a level of about 0.05 to about 2.0 weight percent (wt%), based upon the total weight of the polycarbonate in the binder composition.
- the polycarbonate may be produced by a melt polycondensation reaction between a dihydroxy compound and a carbonic acid diester.
- suitable carbonic acid diesters that may be utilized to produce the polycarbonates are diphenyl carbonate, bis(2,4-dichlorophenyl)carbonate, bis(2,4,6-trichlorophenyl) carbonate, bis(2-cyanophenyl) carbonate, bis(o-nitrophenyl) carbonate, ditolyl carbonate, m-cresyl carbonate, dinaphthyl carbonate, bis(diphenyl) carbonate, diethyl carbonate, dimethyl carbonate, dibutyl carbonate, dicyclohexyl carbonate, or the like, or combinations comprising at least one of the foregoing carbonic acid diesters.
- the preferred carbonic acid diester is diphenyl carbonate.
- a suitable number average molecular weight for the polycarbonate is about 3,000 to about 1,000,000 grams/mole (g/mole). In one embodiment, it is desirable for the number average molecular weight of the polycarbonate to be about 10,000 to about 100,000 g/mole. In another embodiment, it is desirable for the number average molecular weight of the polycarbonate to be about 20,000 to about 75,000 g/mole. In yet another embodiment, it is desirable for the number average molecular weight of the polycarbonate to be about 25,000 to about 35,000 g/mole.
- Cycloaliphatic polyesters suitable for use in the binder composition are those that are characterized by optical transparency, improved weatherability and low water absorption. It is also generally desirable that the cycloaliphatic polyesters have good melt compatibility with the polycarbonate resins since the polyesters can be mixed with the polycarbonate resins for use in the binder composition. Cycloaliphatic polyesters are generally prepared by reaction of a diol with a dibasic acid or an acid derivative.
- the diols used in the preparation of the cycloaliphatic polyester resins for use in the binder composition are straight chain, branched, or cycloaliphatic, preferably straight chain or branched alkane diols, and may contain from 2 to 12 carbon atoms.
- diols include ethylene glycol, propylene glycol, e.g., 1,2- and 1,3- propylene glycol; butane diol, i.e., 1,3- and 1 ,4-butane diol; diethylene glycol, 2,2- dimethyl- 1 ,3 -propane diol, 2-ethyl, 2-methyl, 1 ,3-propane diol, 1 ,3- and 1,5-pentane diol, dipropylene glycol, 2-methyl- 1 ,5-pentane diol, 1 ,6-hexane diol, 1 ,4- cyclohexane dimethanol and particularly its cis- and trans-isomers, triethylene glycol, 1 ,10-decane diol, ore the like, or a combination comprising at least one of the foregoing diols.
- diols include ethylene glycol, propylene glycol, e.g., 1,2-
- 1,4-cyclohexane dimeO.LOLthanol is to be used as the diol component, it is generally preferred to use a mixture of cis- to trans-isomers in ratios of about 1 :4 to about 4:1. Within this range, it is generally desired to use a ratio of cis- to trans- isomers of about 1 :3.
- the diacids useful in the preparation of the cycloaliphatic polyester resins are aliphatic diacids that include carboxylic acids having two carboxyl groups each of which are attached to a saturated carbon in a saturated ring.
- suitable cycloaliphatic acids include decahydro naphthalene dicarboxylic acid, norbornene dicarboxylic acids, bicyclo octane dicarboxylic acids.
- Exemplary cycloaliphatic diacids are 1 ,4-cyclohexanedicarboxylic acid and trans- 1 , 4-cyclohexanedicarboxylic acids.
- Linear aliphatic diacids are also useful provided the polyester has at least one monomer containing a cycloaliphatic ring.
- Illustrative examples of linear aliphatic diacids are succinic acid, adipic acid, dimethyl succinic acid, and azelaic acid. Mixtures of diacid and diols may also be used to make the cycloaliphatic polyesters.
- Cyclohexanedicarboxylic acids and their chemical equivalents can be prepared, for example, by the hydrogenation of cycloaromatic diacids and corresponding derivatives such as isophthalic acid, terephthalic acid of naphthalenic acid in a suitable solvent, water or acetic acid at room temperature and at atmospheric pressure using suitable catalysts such as rhodium supported on a suitable earner of carbon or alumina. They may also be prepared by the use of an inert liquid medium wherein an acid is at least partially soluble under reaction conditions and a catalyst of palladium or ruthenium in carbon or silica is used.
- two or more isomers are obtained in which the carboxylic acid groups are in cis- or trans-positions.
- the cis- and trans-isomers can be separated by crystallization with or without a solvent or by distillation. Mixtures of the cis- and trans-isomers may also be used, and preferably when such a mixture is used, the trans-isomer can comprise at least about 75 wt% and the cis-isomer can comprise the remainder based on the total weight of cis- and trans-isomers combined.
- a copolyester or a mixture of two polyesters may be used as the cycloaliphatic polyester resin.
- Chemical equivalents of these diacids including esters may also be used in the preparation of the cycloaliphatic polyesters.
- suitable chemical equivalents for the diacids are alkyl esters, e.g., dialkyl esters, diaryl esters, anhydrides, acid chlorides, acid bromides, or the like, or combinations comprising at least one of the foregoing chemical equivalents.
- Exemplary chemical equivalents comprise the dialkyl esters of the cycloaliphatic diacids, with the most desirable being the dimethyl ester of the acid, particularly dimethyl-trans- 1 ,4- cyclohexanedicarboxylate. Dimethyl- 1,4-cyclohexanedicarboxylate can be obtained by ring hydrogenation of dimethylterephthalate..
- polyester resins can be obtained through the condensation or ester interchange polymerization of the diol or diol chemical equivalent component with the diacid or diacid chemical equivalent component and has recurring units of the formula (IX):
- R 3 represents an alkyl or cycloalkyl radical containing 2 to 12 carbon atoms and which is the residue of a straight chain, branched, or cycloaliphatic alkane diol having 2 to 12 carbon atoms or chemical equivalents thereof; and R 4 is an alkyl or a cycloaliphatic radical which is the decarboxylated residue derived from a diacid, with the proviso that at least one of R 3 or R is a cycloalkyl group.
- a preferred cycloaliphatic polyester is poly(l ,4-cyclohexane- dimethanol-1,4- cyclohexanedicarboxylate) having recurring units of formula (X)
- R is a cyclohexane ring
- R 4 is a cyclohexane ring derived from cyclohexanedicarboxylate or a chemical equivalent thereof and is selected from the cis- or trans-isomer or a mixture of cis- and trans- isomers thereof.
- Cycloaliphatic polyester resins can be generally made in the presence of a suitable catalyst such as a tetra(2-ethyl hexyl)titanate, in a suitable amount, typically about 50 to 400 ppm of titanium based upon the total weight of the final product.
- copolyesters comprising about 0.5 to about 30 percent by weight (wt%), of units derived from aliphatic acids and/or aliphatic polyols with the remainder of the polyester being a resorcinol aryl polyesters derived from aromatic diols and aromatic polyols.
- Polyarylates that can be used in the binder composition refers to polyesters of aromatic dicarboxylic acids and bisphenols.
- Polyarylate copolymers including carbonate linkages in addition to the aryl ester linkages, known as polyester- carbonates, are also suitable. These aryl esters may be used alone or in combination with each other or more preferably in combination with bisphenol polycarbonates.
- These organic polymers can be prepared in solution or by melt polymerization from aromatic dicarboxylic acids or their ester forming derivatives and bisphenols and their derivatives.
- aromatic dicarboxylic acids represented by the decarboxylated residue R are isophthalic or terephthalic acid, 1 ,2-di(p-carboxyphenyl)ethane, 4,4'- dicarboxydiphenyl ether, 4,4' bisbenzoic acid, and mixtures thereof. All of these acids contain at least one aromatic nucleus. Acids containing fused rings can also be present, such as in 1 ,4- 1 ,5- or 2,6-naphthalene dicarboxylic acids.
- the preferred dicarboxylic acids are terephthalic acid, isophthalic acid, naphthalene dicarboxylic acid, or the like, or a combination comprising at least one of the foregoing dicarboxylic acids.
- Blends of organic polymers may also be used as the binder composition for the data storage devices.
- Preferred organic polymer blends are polycarbonate (PC)-poly(l,4- cyclohexane-dimethanol-1 ,4-cyclohexanedicarboxylate) (PCCD), PC- poly(cyclohexanedimethanol-co-ethylene terephthalate) (PETG), PC-polyethylene terephthalate (PET), PC-polybutylene terephthalate (PBT), PC- polymethylmethacrylate (PMMA), PC-PCCD-PETG, resorcinol aryl polyester-PCCD, resorcinol aryl polyester-PETG, PC-resorcinol aryl polyester, resorcinol aryl polyester-polymethylmethacrylate (PMMA), resorcinol aryl polyester-PCCD-PETG, or the like, or a combination comprising at least one of the foregoing.
- Binary blends, ternary blends and blends having more than three resins may also be used in the polymeric alloys.
- one of the polymeric resins in the alloy may comprise about 1 to about 99 weight percent (wt%) based on the total weight of the composition. Within this range, it is generally desirable to have the one of the polymeric resins in an amount greater than or equal to about 20, preferably greater than or equal to about 30 and more preferably greater than or equal to about 40 wt%, based on the total weight of the composition.
- the various polymeric resins may be present in any desirable weight ratio.
- thermosetting polymers examples include polysiloxanes, phenolics, polyurethanes, epoxies, polyesters, polyamides, polyacrylates, polymethacrylates, or the like, or a combination comprising at least one of the foregoing thermosetting polymers.
- the organic material can be a precursor to a thermosetting polymer.
- the photoactive material is a photochromic dye.
- the photochromic dye is one that is capable of being written and read by electromagnetic radiation. It is desirable to use photochromic dyes that can be written and read using actinic radiation i.e., from about 350 to about 1 ,100 nanometers.
- the wavelengths at which writing and reading are accomplished are about 400 nanometers to about 800 nanometers. In one embodiment, the writing and reading are accomplished at a wavelength of about 400 to about 600 nanometers. In another embodiment, the writing and reading are accomplished at a wavelength of about 400 to about 550 nanometers. Exemplary wavelengths at which writing and reading are accomplished are about 405 nanometers and about 532 nanometers.
- Suitable examples of photochromic dyes are a diarylethene or a nitrone.
- An exemplary diarylethylene compound can be represented by formula
- R 2 and R 5 are each independently Ci-C 3 alkyl or C]-C 3 perfluoroalkyl;
- R 3 is Ci-C 3 alkyl, C 1 -C 3 perfluoroalkyl, hydrogen, or fluorine;
- R 4 and R 6 are each independently C] -C 3 alkyl, Ci-C 3 perfluoroalkyl, CN, hydrogen, fluorine, phenyl, pyridyl, isoxazole, -CHC(CN) 2 , aldehyde, carboxylic acid, -(Ci-C 5 alkyl)COOH or 2- methylenebenzo[d][ l ,3]dithiole;
- X and Y are each independently oxygen, nitrogen, or sulfur, wherein the nitrogen is optionally substituted with Ci-C 3 alkyl or Ci-C 3 perfluoroalkyl; and wherein Q is nitrogen.
- diarylethenes that can be used as photoactive materials include diarylperfluorocyclopentenes, diarylmaleic anhydrides, diarylmaleimides, or a combination comprising at least one of the foregoing diarylethenes.
- the diarylethenes are present as open-ring or closed-ring isomers.
- the open ring isomers of diarylethenes have absorption bands at shorter wavelengths. Upon irradiation with ultraviolet light, new absoiption bands appear at longer wavelengths, which are ascribed to the closed-ring isomers.
- the absorption spectra of the closed-ring isomers depend on the substituents of the thiophene rings, naphthalene rings or the phenyl rings.
- the absorption structures of the open-ring isomers depend upon the upper cycloalkene structures.
- the open-ring isomers of maleic anhydride or maleimide derivatives show spectral shifts to longer wavelengths in comparison with the perfluorocyclopentene derivatives.
- diarylethene closed ring isomers examples include:
- Diarylethenes with five-membered heterocyclic rings have two conformations with the two rings in mirror symmetry (parallel conformation) and in C 2 (antiparallel conformation).
- the population ratio of the two conformations is 1 :1.
- Increasing the population ratio of the antiparallel conformation to the parallel conformation can be accomplished by covalently bonding bulky substituents such as the -(C 1 -C 5 alkyl)COOH substituent to diarylethenes having five-membered heterocyclic rings.
- the diarylethenes can be in the form of a polymer having the general formula (XXXXIV) below.
- the formula (XXXXIV) represents the open isomer form of the polymer.
- diarylethenes can be reacted in the presence of light.
- an exemplary diarylethene can undergo a reversible cyclization reaction in the presence of light according to the following equation (I):
- the cyclization reaction can be used to produce a hologram.
- the hologram can be produced by using radiation to react the open isomer form to the closed isomer form or vice- versa.
- a diarylethene can undergo a gated reaction in the presence of light.
- diarylethenes with five-membered heterocyclic rings have two conformations with the two rings in mirror symmetry (parallel conformation) and in C 2 (antiparallel conformation).
- Photocyclization can proceed only from the antiparallel conformation. The photocyclization is prohibited when the compound is fixed in the mirror symmetry conformation.
- equation (III) the formation of intramolecular hydrogen bonding fastens the compound in the parallel conformation thereby making the compound photochemically inactive. Heat can be used to break this intramolecular hydrogen bonding.
- Diarylethene compounds having special substituents that reversibly fix the conformation undergo gated photochromic reactions, according to the following equation (III):
- Equation (III) is termed a gated reaction and can preserve stored data even when readout operations are repeatedly conducted at the same wavelength as the writing operation. Thus by using diarylethenes in ⁇ vhich gating is made to occur, the writing and reading can be conducted at the same wavelength.
- Nitrones can also be used as photochromic dyes in the holographic storage media. Nitrones have the general structure shown in the formula (XXXXV):
- An exemplary nitrone generally comprises an aryl nitrone structure represented by the formula (XXXXVI):
- Z is (R 3 ) a — Q— R 4 — or R 5 — ;
- Q is a monovalent, divalent or trivalent substituent or linking group; wherein each of R, R 1 , R 2 and R 3 is independently hydrogen, an alkyl or substituted alkyl radical containing 1 to about 8 carbon atoms or an aromatic radical containing 6 to about 13 carbon atoms;
- R 4 is an aromatic radical containing 6 to about 13 carbon atoms;
- R " is an aromatic radical containing 6 to about 20 carbon atoms which have substituents that contain hetero atoms, wherein the hetero atoms are at least one of oxygen, nitrogen or sulfur;
- R 6 is an aromatic hydrocarbon radical containing 6 to about 20 carbon atoms;
- X is a halo, cyano, nitro, aliphatic acyl, alkyl, substituted alkyl having 1 to about 8 carbon atoms, aryl having 6 to about 20 carbon atoms, carbalkoxy, or an electron withdraw
- R 7 is a an alkyl radical having 1 to about 8 carbon atoms; a is an amount of up to about 2; b is an amount of up to about 3; and n is up to about 4.
- the nitrones may be ⁇ -aryl-N-arylnitrones or conjugated analogs thereof in which the conjugation is between the aryl group and an ⁇ -carbon atom.
- the ⁇ -aryl group is frequently substituted, most often by a dialkylamino group in which the alkyl groups contain 1 to about 4 carbon atoms.
- the R is hydrogen and R is phenyl.
- Q can be monovalent, divalent or trivalent according as the value of "a" is 0, 1 or 2. Illustrative Q values are shown in the Table 1 below. Table 1
- Q is desirable for Q to be fluorine, chlorine, bromine, iodine, oxygen, sulfur or nitrogen.
- nitrones are ⁇ -(4-diethylaminophenyl)-N-phenylnitrone; ⁇ -(4- diethylaminophenyl)-N-(4-chlorophenyl)-nitrone, ⁇ -(4-diethylaminophenyl)-N-(3,4- dichlorophenyl)-nitrone, ⁇ -(4-diethylaminophenyl)-N-(4-carbethoxyphienyl)-nitrone, ⁇ -(4-diethylaminophenyl)-N-(4-acetylphenyl)-nitrone, ⁇ -(4-dimethylaminophenyl)-N- (4-cyanophenyl)-nitrone, ⁇ -(4-methoxyphenyl)-N-(4-cyanophenyl)nitrone, ⁇ -(9- julolidinyl)-N-phenyl
- the photoactive material is disposed upon a first film that comprises an organic polymer.
- the first film behaves as a substrate upon which is disposed the photoactive material.
- the photoactive material can be disposed upon the first film in the form of a complete or partial layer.
- a second film is disposed upon a surface of the photoactive material opposed to the surface in contact with the first film.
- the first and the second films can be molded or cast from solution.
- the second film can be disposed upon the surface of the photoactive material by molding.
- the photoactive material is then coated onto the surface of the first film or the surface of the second film or upon the opposing surfaces of both the first film and the second film.
- molding can include injection molding, blow molding, compression molding, vacuum forming, or the like.
- processes by which the photoactive material can be coated onto the surface of the film are by brush painting, dip coating, spray painting, spin coating, or the like.
- a photochromic material When a photochromic material is disposed upon a film to form the holographic data storage as described above, it is generally desirable to have the film having a thickness of about 1 to about 100,000 micrometers ( ⁇ m). In one embodiment, it is desirable to have a thickness of about 2 to about 10,000 ⁇ m. In another embodiment, it is desirable to have a thickness of about 3 to about 1,000 ⁇ m. In yet another embodiment, it is desirable to have a thickness of about 7 to about 500 ⁇ m.
- the photoactive material in another method of manufacturing the holographic data storage media, can be incorporated into the organic polymer in a mixing process to form a data storage composition.
- the data storage composition is injection molded into an article that can be used as holographic data storage media.
- the injection molded article can have any geometry. Examples of suitable geometries are circular discs, square shaped plates, polygonal shapes, or the like.
- the mixing processes by which the photoactive material can be incorporated into the organic polymer involves the use of shear force, extensional force, compressive force, ultrasonic energy, electromagnetic energy, thermal energy or combinations comprising at least one of the foregoing forces or forms of energy and is conducted in equipment wherein the aforementioned forces are exerted by a single screw, multiple screws, intermeshing co-rotating or counter rotating screws, non-inte ⁇ neshing co- rotating or counter rotating screws, reciprocating screws, screws with pins, screws with screens, barrels with pins, rolls, rams, helical rotors, baffles, or combinations comprising at least one of the foregoing.
- the mixing can be conducted in machines such as a single or multiple screw extruder, a Buss kneader, a Henschel, a helicone, an Eirich mixer, a Ross mixer, a Banbury, a roll mill, molding machines such as injection molding machines, vacuum forming machines, blow molding machine, or then like, or a combination comprising at least one of the foregoing machines.
- machines such as a single or multiple screw extruder, a Buss kneader, a Henschel, a helicone, an Eirich mixer, a Ross mixer, a Banbury, a roll mill, molding machines such as injection molding machines, vacuum forming machines, blow molding machine, or then like, or a combination comprising at least one of the foregoing machines.
- a holographic composition generally comprises about 0.1 to about 50 weight percent (wt%), based on the total weight of the holographic composition. In one embodiment, the holographic composition comprises about 1 to about 40 wt%, based upon the total weight of the holographic composition. In another embodiment, the holographic composition comprises about 2 to about 20 wt%, based upon the total weight of the holographic composition. In yet another embodiment, the holographic composition comprises about 3 to about 10 wt%, based upon the total weight of the holographic composition.
- the data can be stored onto the media by irradiating the media with electromagnetic energy having a first wavelength.
- the irradiation facilitates the conversion of the open form of the isomer to the closed form of the isomer (cyclization) of the photochromic dye thereby creating a hologram into which the data is encoded.
- the irradiation facilitates the conversion of the closed form of the isomer to the open form of the isomer of the photochromic dye thereby creating a hologram into which the data is encoded.
- the media is irradiated with electromagnetic energy having a second wavelength.
- the first and second wavelengths can be between 350 and 1,100 nm.
- the first wavelength is not equal to the second wavelength.
- the wavelength used to store the data is the same as the wavelength used to read the data. In such an embodiment, the first wavelength is equal to the second wavelength.
- the photochromic dye after being reacted can be converted to a non-photochromic state so that any written data cannot be destroyed.
- the conversion of the photochromic dye to the non-photochromic state can be induced by an electric field, by a third wavelength, by a photoacid generator or by a combination comprising at least one of the foregoing.
- FIG. Ia An example of a suitable holographic data storage process to create holographic storage media of the present disclosure is set forth in Figure Ia.
- the output from a laser 10 is divided into two equal beams by beam splitter 20.
- One beam, the signal beam 40 is incident on a form of spatial light modulator (SLM) or deformable mirror device (DMD) 30, which imposes the data to be stored in signal beam 40.
- SLM spatial light modulator
- DMD deformable mirror device
- This device is composed of a number of pixels that can block or transmit the light based upon input electrical signals. Each pixel can represent a bit or a part of a bit (a single bit may consume more than one pixel of the SLM or DMD 30) of data to be stored.
- the output of SLM or DMD 30 is then incident on the storage medium 60.
- the second beam, the reference beam 50, is transmitted all the way to storage medium 60 by reflection off first mirror 70 with minimal distortion.
- the two beams are coincident on the same area of storage medium 60 at different angles.
- the net result is that the two beams create an interference pattern at their intersection in the storage medium 60.
- the interference pattern is a unique function of the data imparted to signal beam 40 by SLM or DMD 30.
- At least a portion of the photoactive monomer undergoes cyclization, which leads to a modification of the refractive index in the region exposed to the laser light and fixes the interference pattern, effectively creating a grating in the storage medium 60.
- the grating or pattern created in storage medium 60 is simply exposed to reference beam 50 in the absence of signal beam 40 by blocking signal beam 40 with a shutter 80 and the data is reconstructed in a recreated signal beam 90.
- a diffraction efficiency measurement can be used.
- a suitable system for these measurements is shown in Figure 2a.
- This setup is very similar to the holographic storage setup; however, there is no SLM or DMD, but instead, a second mirror 100.
- the laser 10 is split into two beams 110 and 120 that are then interfered in storage medium 60 creating a plane wave grating.
- one of the beams is then turned off or blocked with shutter 80 and the amount of light diffracted by the grating in storage medium 60 is measured.
- the diffraction efficiency is measured as the power in diffracted beam 130 versus the amount of total power incident on storage medium 60. More accurate measurements may also take into account losses in storage medium 60 resulting from reflections at its surfaces and/or absorption within its volume.
- a holographic plane-wave characterization system may be used to test the characteristics of the medium, especially multiplexed holograms.
- Such a system can provide the M/# for a given sample, which is the metric used to characterize the ultimate dynamic range or information storage capacity of the sample as measured by the maximum number and efficiency of multiplexed holograms stored in the medium.
- a suitable system for these measurements is shown in Figure 3. In this setup the output from first laser 10 is passed through a first shutter 140 for read/write control, a combination of a first half-wave plate 150, and a first polarizing beam splitter 160 for power control.
- the light is then passed through a first two-lens telescope 170 to adjust the beam size and reflected off first mirror 180 followed by second mirror 190 to transport the beam into the measurement area.
- the light is then passed through a second half-wave plate 200 and a second polarizing beam splitter 210 to split the beam in two and to control the power in each of the two beams.
- the beam reflected off of beam splitter 210 is then passed through a second shutter 220, which enables independent on/off control of the power in the first beam.
- the first beam is then reflected off of a third mirror 230 and is incident on medium 60, which is mounted on a rotation stage 240.
- the light from the first beam transmitted through medium 60 is collected into a first detector 250.
- the second beam is passed through a third half- wave plate 260 to rotate its polarization into the same direction as the first beam and then through a third shutter 225 to provide on/off control of the second beam.
- the second beam is then reflected off of fourth mirror 235 and is incident on medium 60.
- a second laser 270 is passed through a second two-lens telescope 175, reflected off of fifth mirror 185 and then sixth mirror 195, and is then coincident on medium 60 at the same location as the first and second beams.
- the diffracted beam is then collected into second detector 255.
- the holographic storage medium may be utilized in conjunction with a process whereby light of one wavelength from a laser is utilized to write the data into the holographic storage medium, while light of the same or a different wavelength is utilized to read the data.
- the wavelength employed for writing the data is a function of the specific photoactive material used.
- the holographic storage medium can be used for single bit type data storage. It can also be used for data storage when multiple layers are stored in a given volume.
- the wavelengths utilized for writing and reading the holographic storage media of the present disclosure will depend upon the light source, and the specific photoactive material.
- the catalyst solution was prepared by dissolving one drop of platinum(O) 1 ,3- divinyltetramethyldisiloxane (in xylene) in 1 mL of vinyl terminated poly- methylphenylsiloxane. Hydromethylsiloxane-methylphenylsiloxane copolymer was used as the crosslinker. After mixing for 10 minutes, samples were prepared by sandwiching 0.25 mL of the solution between glass slides, using 0.26 millimeter (mm) plastic spacers to maintain thickness. The samples were heated at 7O 0 C for 2 minutes (min) per side, exposed to UV (a Xenon UV curing bulb type B at 3 inch bulb height from sample) for 10 seconds and wrapped in foil until tested. The diffraction efficiency of this material was measured on the holographic test bed by recording a plane wave hologram.
- the holographic composition is advantageous in that it permits manufacturing a holographic storage medium in an efficient and cost effective manner. It also allows for fast replication and can be handled by the end-user.
Landscapes
- Compositions Of Macromolecular Compounds (AREA)
- Holo Graphy (AREA)
Abstract
Description
Claims
Priority Applications (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
EP05798422A EP1797557A1 (en) | 2004-09-30 | 2005-09-16 | Holographic storage medium |
JP2007534640A JP2008515023A (en) | 2004-09-30 | 2005-09-16 | Holographic storage medium |
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US10/954,779 | 2004-09-30 | ||
US10/954,779 US7897296B2 (en) | 2004-09-30 | 2004-09-30 | Method for holographic storage |
Publications (1)
Publication Number | Publication Date |
---|---|
WO2006039130A1 true WO2006039130A1 (en) | 2006-04-13 |
Family
ID=35520277
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
PCT/US2005/033438 WO2006039130A1 (en) | 2004-09-30 | 2005-09-16 | Holographic storage medium |
Country Status (4)
Country | Link |
---|---|
US (1) | US7897296B2 (en) |
EP (1) | EP1797557A1 (en) |
JP (1) | JP2008515023A (en) |
WO (1) | WO2006039130A1 (en) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007050354A2 (en) * | 2005-10-27 | 2007-05-03 | General Electric Company | Methods for making holographic data storage articles |
WO2007067670A2 (en) * | 2005-12-07 | 2007-06-14 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
JP2008224834A (en) * | 2007-03-09 | 2008-09-25 | Adeka Corp | Composition for optical recording medium, and recording/display medium |
EP2003492A1 (en) | 2007-06-13 | 2008-12-17 | Xerox Corporation | Inkless Reimageable Printing Paper and Method |
WO2009072988A1 (en) * | 2007-12-07 | 2009-06-11 | Polycore Optical Pte Ltd | Encapsulated photochromic dyes |
US7553603B2 (en) | 2007-06-13 | 2009-06-30 | Xerox Corporation | Inkless printing paper and method |
US7569316B2 (en) | 2007-06-13 | 2009-08-04 | Xerox Corporation | Inkless reimageable printing paper and method |
US7572560B2 (en) | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless reimageable printing paper and method |
US7572569B2 (en) | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless printing paper and method |
US7582398B2 (en) | 2007-06-13 | 2009-09-01 | Xerox Corporation | Inkless reimageable printing paper and method |
US7588878B2 (en) | 2007-06-13 | 2009-09-15 | Xerox Corporation | Inkless printing paper and method |
US7645560B1 (en) | 2008-09-08 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US7645558B2 (en) | 2007-06-13 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US7655366B2 (en) | 2007-06-13 | 2010-02-02 | Xerox Corporation | Inkless reimageable printing paper and method |
US7666558B2 (en) | 2007-06-13 | 2010-02-23 | Xerox Corporation | Inkless reimageable printing paper and method |
US7718325B2 (en) | 2007-06-13 | 2010-05-18 | Xerox Corporation | Photochromic material, inkless reimageable printing paper, and methods |
US7852366B2 (en) | 2007-06-13 | 2010-12-14 | Xerox Corporation | System and method for printing reimageable transient documents |
US7867672B2 (en) | 2007-06-13 | 2011-01-11 | Xerox Corporation | Reimageable paper protected against UV light |
US8715887B2 (en) | 2010-07-30 | 2014-05-06 | Sabic Innovative Plastics Ip B.V. | Complex holograms, method of making and using complex holograms |
Families Citing this family (30)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US8536205B2 (en) * | 2005-05-25 | 2013-09-17 | Switch Materials Inc. | Photochromic and electrochromic compounds and synthesis and use thereof |
US20070147214A1 (en) * | 2005-12-22 | 2007-06-28 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
US8808944B2 (en) | 2006-03-15 | 2014-08-19 | General Electric Company | Method for storing holographic data |
US20080055686A1 (en) * | 2006-09-05 | 2008-03-06 | Christoph Georg Erben | Holographic data recording method and system |
US20080084592A1 (en) * | 2006-10-09 | 2008-04-10 | General Electric Company | Molded Article Incorporating Volume Hologram |
US9164480B2 (en) * | 2006-12-14 | 2015-10-20 | General Electric Company | Holographic data storage device and method of making |
US8501371B2 (en) * | 2006-12-14 | 2013-08-06 | General Electric Company | Holographic data storage method and system |
US7901839B2 (en) * | 2007-09-25 | 2011-03-08 | General Electric Company | Compositions and methods for storing holographic data |
US7989488B2 (en) * | 2007-09-25 | 2011-08-02 | General Electric Company | Compositions and methods for storing holographic data |
US20100180937A1 (en) * | 2008-06-30 | 2010-07-22 | General Electric Company | Holographic energy-collecting medium and associated device |
US20090325078A1 (en) * | 2008-06-30 | 2009-12-31 | General Electric Company | Holographic recording medium |
US8089846B2 (en) * | 2008-12-16 | 2012-01-03 | General Electric Company | Method and system for modulation coding and synchronization |
US8238217B2 (en) * | 2008-12-16 | 2012-08-07 | General Electric Company | Method and system for detection enhancement for optical data storage |
US8891343B2 (en) * | 2008-12-17 | 2014-11-18 | General Electric Corporation | Method for formatting and reading data disks |
US8125862B2 (en) * | 2008-12-18 | 2012-02-28 | General Electric Company | System and method for controlling tracking in an optical drive |
US8233368B2 (en) * | 2008-12-18 | 2012-07-31 | General Electric Copany | Method and system for bit prediction using a multi-pixel detector |
US8331210B2 (en) * | 2008-12-23 | 2012-12-11 | General Electric Company | System and method for storage of data in circular data tracks on optical discs |
US7990818B2 (en) * | 2008-12-23 | 2011-08-02 | General Electric Company | Cascaded control of a pick-up head for multi-layer optical data storage |
US8194520B2 (en) * | 2008-12-30 | 2012-06-05 | General Electric Company | Disc structure for bit-wise holographic storage |
US8427912B2 (en) | 2008-12-30 | 2013-04-23 | General Electric Company | System and method for tracking in single-bit holographic data storage |
US9373351B2 (en) | 2008-12-31 | 2016-06-21 | General Electric Comany | System and method for dual-beam recording and readout of multilayered optical data storage media |
US8345334B2 (en) | 2008-12-31 | 2013-01-01 | General Electric Company | Mastering and replication of micro-holographic data storage media |
US7961572B2 (en) | 2009-03-30 | 2011-06-14 | General Electric Company | System and method for reading micro-holograms with reduced error rates |
US8609300B2 (en) * | 2009-06-25 | 2013-12-17 | Sabic Innovative Plastics Ip B.V. | Method of making holographic recording materials and articles formed thereby |
US8728685B2 (en) | 2009-06-25 | 2014-05-20 | Sabic Innovative Plastics Ip B.V. | Method of making holographic storage medium |
US8304747B2 (en) * | 2009-09-10 | 2012-11-06 | Xerox Corporation | Sensors and methods for determining whether an item has been exposed to an environmental condition |
US8289830B2 (en) * | 2009-12-16 | 2012-10-16 | International Business Machines Corporation | Storing data on fiber data storage media |
US20130004887A1 (en) | 2011-06-29 | 2013-01-03 | Sabic Innovative Plastics Ip B.V. | Holographic recording medium |
US20130071773A1 (en) | 2011-09-16 | 2013-03-21 | Sabic Innovative Plastics Ip B.V. | Holographic storage medium |
US8663873B2 (en) | 2012-01-13 | 2014-03-04 | Sabic Innovative Plastics Ip B.V. | Holographic recording medium and method of recording a hologram |
Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5023859A (en) * | 1988-03-30 | 1991-06-11 | Rohm Gmbh Chemische Fabrik | Optical data storage apparatus and method utilizing an amorphous polymer which exhibits photochromic properties |
EP0566233A1 (en) * | 1992-02-27 | 1993-10-20 | SHARP Corporation | Optical memory medium and a method of recording information on the same |
US5443940A (en) * | 1992-04-16 | 1995-08-22 | Sanyo Electric Co., Ltd. | Optical recording material and optical recording medium employing the same |
US6046925A (en) * | 1997-04-14 | 2000-04-04 | The Regents Of The University Of California | Photochromic fluorescent proteins and optical memory storage devices based on fluorescent proteins |
WO2001037266A1 (en) * | 1999-11-17 | 2001-05-25 | The Research Foundation Of State University Of New York | Three dimensional data storage device and method for reading |
US20040072100A1 (en) * | 2002-09-04 | 2004-04-15 | Toshiko Mizokuro | Optical recording medium, production method thereof and method of using same |
Family Cites Families (118)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
NL140629B (en) * | 1963-07-04 | 1973-12-17 | Kalle Ag | LIGHT-SENSITIVE MATERIAL FOR THE MANUFACTURE OF PRINTING FORMS AND THE PRINTING FORMS PRODUCED THEREOF. |
US3635544A (en) * | 1963-12-23 | 1972-01-18 | American Cyanamid Co | Photochromic polymer matrix |
US3635895A (en) | 1965-09-01 | 1972-01-18 | Gen Electric | Process for preparing thermoplastic polycarbonates |
US3988159A (en) * | 1967-07-28 | 1976-10-26 | American Can Company | Light-sensitive material containing nitrone for forming heat-fixed images |
US3968051A (en) * | 1968-10-21 | 1976-07-06 | American Cyanamid Company | Freeze drying photochromic filters |
US3658543A (en) | 1970-12-18 | 1972-04-25 | Du Pont | Dual response photosensitive composition containing acyl ester of triethanolamine |
DE2125110C3 (en) * | 1971-05-21 | 1979-11-22 | Hoechst Ag, 6000 Frankfurt | Process for the production of holograms |
US3989530A (en) * | 1974-03-19 | 1976-11-02 | Robillard Jean J A | Process for recording phase holograms using energy-activated sensitizer |
US4367170A (en) * | 1975-01-24 | 1983-01-04 | American Optical Corporation | Stabilized photochromic materials |
US4001184A (en) | 1975-03-31 | 1977-01-04 | General Electric Company | Process for preparing a branched polycarbonate |
US4220708A (en) | 1977-07-22 | 1980-09-02 | Heller Harold G | Photochromic compounds |
US4217438A (en) | 1978-12-15 | 1980-08-12 | General Electric Company | Polycarbonate transesterification process |
US4286957A (en) * | 1979-01-10 | 1981-09-01 | Essilor International "Cie Generale D'optique" | Process of integrating a photochromic substance into an ophthalmic lens and a photochromic lens of organic material |
US4859789A (en) * | 1982-11-01 | 1989-08-22 | General Electric Company | Diarylnitrones |
US4990665A (en) * | 1982-11-01 | 1991-02-05 | Microsi, Inc. | Diarylnitrones |
US5108874A (en) * | 1982-11-01 | 1992-04-28 | Microsi, Inc. | Composite useful in photolithography |
US4702996A (en) | 1983-09-28 | 1987-10-27 | General Electric Company | Method of enhancing the contrast of images and materials therefor |
CA1246565A (en) * | 1984-07-06 | 1988-12-13 | Shinichi Yamamoto | Spiro-oxazine compounds and preparation thereof and photochronic shaped article |
US4663275A (en) | 1984-09-04 | 1987-05-05 | General Electric Company | Photolithographic method and combination including barrier layer |
US4667049A (en) | 1984-11-02 | 1987-05-19 | Etd Technology Inc. | Method of making dialkylamino-thioxomethyl-thioalkanesulfonic acid compounds |
US4578344A (en) | 1984-12-20 | 1986-03-25 | General Electric Company | Photolithographic method using a two-layer photoresist and photobleachable film |
US4661433A (en) | 1984-12-31 | 1987-04-28 | General Electric Company | Storage stable aryl nitrone compositions |
US4623611A (en) | 1985-01-16 | 1986-11-18 | General Electric Company | Photolithographic stripping method for removing contrast enhancement layer |
GB8501779D0 (en) * | 1985-01-24 | 1985-02-27 | Plessey Co Plc | Photochromic 3-pyrryl fulgides |
US4709107A (en) * | 1985-10-11 | 1987-11-24 | General Electric Company | Process for producing nitrones |
US5002993A (en) * | 1986-07-25 | 1991-03-26 | Microsi, Inc. | Contrast enhancement layer compositions, alkylnitrones, and use |
US4897829A (en) * | 1986-11-20 | 1990-01-30 | Canon Kabushiki Kaisha | Cardlike optical recording medium |
GB8703400D0 (en) * | 1987-02-13 | 1987-03-18 | Courtaulds Plc | Security marking |
US4920220A (en) * | 1987-11-12 | 1990-04-24 | Ciba-Geigy Corporation | Chromogenic 1-heterocyclic substituted 2,4-benzoxazines |
US5106723A (en) * | 1988-03-10 | 1992-04-21 | Microsi, Inc. | Contrast enhancement layer compositions, alkylnitrones, and use |
US5268862A (en) | 1989-04-25 | 1993-12-07 | The Regents Of The Unversity Of California | Three-dimensional optical memory |
US6483735B1 (en) * | 1989-04-25 | 2002-11-19 | The Regents Of The University Of California | Two-photon, three-or four-dimensional, color radiation memory |
US5325324A (en) * | 1989-04-25 | 1994-06-28 | Regents Of The University Of California | Three-dimensional optical memory |
DE69015886T2 (en) * | 1989-06-05 | 1995-08-03 | Tokuyama Corp | Photochromic compound, its composition and use. |
US5037861A (en) * | 1989-08-09 | 1991-08-06 | General Electric Company | Novel highly reactive silicon-containing epoxides |
US5206395A (en) * | 1990-01-18 | 1993-04-27 | Ciba-Geigy Corporation | Photochromic naphthacenequinones, process for their preparation and the use thereof |
DE59100921D1 (en) * | 1990-01-18 | 1994-03-10 | Ciba Geigy | Photochromic naphthacene quinones, process for their preparation and their use. |
JPH03213394A (en) * | 1990-01-19 | 1991-09-18 | Hitachi Ltd | Photosensitive recording material and recording and reproducing method using the same |
US5260399A (en) * | 1992-06-08 | 1993-11-09 | General Electric Company | Regiospecific catalyst for the synthesis of epoxysiloxane monomers and polymers |
US5169962A (en) | 1990-09-17 | 1992-12-08 | General Electric Company | Preparation of epoxysilicon compounds using rhodium catalysts |
US5387698A (en) * | 1992-06-11 | 1995-02-07 | General Electric Company | Rhodium containing selective catalysts for the synthesis of epoxysiloxane/epoxysilicone monomers and polymers |
AU638815B2 (en) * | 1990-03-29 | 1993-07-08 | Tokuyama Soda Kabushiki Kaisha | Photochromic compound, composition and use thereof |
US5178978A (en) * | 1990-09-06 | 1993-01-12 | The United States Of America As Represented By The Secretary Of The Air Force | Fabricating integrated optics |
US5064264A (en) * | 1990-10-26 | 1991-11-12 | International Business Machines Corporation | Photorefractive materials |
US5102771A (en) * | 1990-11-26 | 1992-04-07 | Minnesota Mining And Manufacturing Company | Photosensitive materials |
EP0489689B1 (en) * | 1990-12-05 | 1995-03-01 | Ciba-Geigy Ag | Photochromic naphthacenequinones, process for their production and their use |
US5384221A (en) * | 1990-12-12 | 1995-01-24 | Physical Optics Corporation | Birefringent azo dye polymer erasable optical storage medium |
EP0494048A1 (en) * | 1991-01-03 | 1992-07-08 | Ciba-Geigy Ag | Photochromic benzothioxanthoneoxides, process for their preparation and their use |
US5176983A (en) * | 1991-03-04 | 1993-01-05 | Allied-Signal Inc. | Polymeric nitrones having an acrylic backbone chain |
US5260999A (en) * | 1991-06-28 | 1993-11-09 | Digital Equipment Corporation | Filters in license management system |
US5440669A (en) * | 1991-07-26 | 1995-08-08 | Accuwave Corporation | Photorefractive systems and methods |
US5173381A (en) | 1991-08-05 | 1992-12-22 | Queen's University | Azo polymers for reversible optical storage |
US5219710A (en) * | 1991-11-25 | 1993-06-15 | Allied-Signal Inc. | Polymeric nitrones having a styrene-derived backbone chain |
US5253198A (en) * | 1991-12-20 | 1993-10-12 | Syracuse University | Three-dimensional optical memory |
DE4205632A1 (en) * | 1992-02-25 | 1993-08-26 | Bayer Ag | AZINE NEUTROMETHINE |
KR940005716A (en) | 1992-06-11 | 1994-03-22 | 아더 엠. 킹 | Selective catalyst for the synthesis of epoxysilicone monomers and polymers |
DE59304881D1 (en) * | 1992-10-15 | 1997-02-06 | Ciba Geigy Ag | Polymerizable photochromic napthacenediones, polymers of these monomers, processes for their preparation and their use |
JP2663815B2 (en) * | 1992-11-02 | 1997-10-15 | 信越化学工業株式会社 | Method of forming resist pattern |
US5523374A (en) * | 1992-12-03 | 1996-06-04 | Hercules Incorporated | Curable and cured organosilicon compositions |
US5438439A (en) * | 1993-08-13 | 1995-08-01 | Mok; Fai | Non-destructive readout mechanism for volume holograms using two wavelengths |
KR0165729B1 (en) * | 1994-02-18 | 1999-03-20 | 로베르트 뢰머 | Stilbene-based materials, their preparation and use |
JPH07311979A (en) * | 1994-03-24 | 1995-11-28 | Sanyo Electric Co Ltd | Optical recording medium and reproducing method therefor |
US5450218A (en) * | 1994-08-04 | 1995-09-12 | Board Of Trustees Of The Leland Stanford Junior University | Method for encoding and decoding digital data in holographic storage media |
DE4431823A1 (en) * | 1994-09-07 | 1996-03-14 | Bayer Ag | Process for enhancing information in photoaddressable side chain polymers |
DE4434966A1 (en) * | 1994-09-30 | 1996-04-04 | Bayer Ag | New side group polymers and their use for optical components |
US5978112A (en) * | 1995-02-15 | 1999-11-02 | California Institute Of Technology | Non-volatile readout of shift multiplexed holograms |
US5912257A (en) * | 1995-09-06 | 1999-06-15 | The Research Foundation Of State University Of New York | Two-photon upconverting dyes and applications |
US20030022105A1 (en) * | 1995-09-06 | 2003-01-30 | Paras N. Prasad | Two -photon upconverting dyes and applications |
JP3604700B2 (en) * | 1995-10-06 | 2004-12-22 | ポラロイド コーポレイション | Holographic media and processes |
US5759447A (en) * | 1995-12-22 | 1998-06-02 | Hughes Electronics Corporation | Erasable optical memory and method |
DE59706772D1 (en) * | 1996-05-22 | 2002-05-02 | Bayer Ag | FAST PHOTO ADDRESSABLE SUBSTRATES AND PHOTO ADDRESSABLE SIDE GROUP POLYMERS WITH HIGH INDUCIBLE DOUBLE BREAKAGE |
US5719690A (en) * | 1996-05-31 | 1998-02-17 | International Business Machines Corporation | Photorefractive glass article |
JPH1011756A (en) * | 1996-06-24 | 1998-01-16 | Sanyo Electric Co Ltd | Optical operation method for optical device, and optical control device |
US5789015A (en) * | 1996-06-26 | 1998-08-04 | Innotech, Inc. | Impregnation of plastic substrates with photochromic additives |
DE19631864A1 (en) * | 1996-08-07 | 1998-02-12 | Bayer Ag | High sensitivity photoaddressable side group polymers |
US5744280A (en) * | 1996-09-05 | 1998-04-28 | E. I. Du Pont De Nemours And Company | Storage-stable photoimageable deutero leuco dye/photooxidation compositions with improved leuco dye |
US6267913B1 (en) | 1996-11-12 | 2001-07-31 | California Institute Of Technology | Two-photon or higher-order absorbing optical materials and methods of use |
WO1998036298A1 (en) * | 1997-02-12 | 1998-08-20 | University Of Massachusetts | Azobenzene-containing polymer films |
DE19720288A1 (en) * | 1997-05-15 | 1998-11-19 | Bayer Ag | Homopolymers with high photo-inducible birefringence |
US6090332A (en) * | 1997-05-16 | 2000-07-18 | California Institute Of Technology | Process of changing the refractive index of a composite containing a polymer and a compound having large dipole moment and polarizability and applications thereof |
US20030157414A1 (en) | 1997-11-13 | 2003-08-21 | Pradeep K. Dhal | Holographic medium and process for use thereof |
US6482551B1 (en) * | 1998-03-24 | 2002-11-19 | Inphase Technologies | Optical article and process for forming article |
US6124076A (en) * | 1998-07-01 | 2000-09-26 | Lucent Technologies Inc. | Material exhibiting compensation for polymerization-induced shrinkage and recording medium formed therefrom |
US6432610B1 (en) * | 1998-09-08 | 2002-08-13 | Regents Of The University Of California | Dye precursor molecules chemically reactive with the light-altered form of light-sensitive molecules to form stable fluorescent dye, particularly for optical memories including two-photon three-dimensional optical memories |
US6091879A (en) * | 1998-09-15 | 2000-07-18 | Molecular Optoelectronics Corporation | Organic photochromic compositions and method for fabrication of polymer waveguides |
DE19855062A1 (en) | 1998-11-28 | 2000-05-31 | Bayer Ag | Block copolymers based on vinylcyclohexane |
US6627354B1 (en) * | 1999-03-01 | 2003-09-30 | Lucent Technologies Inc. | Photorecording medium, process for fabricating medium, and process for holography using medium |
DE19910247A1 (en) | 1999-03-08 | 2000-09-28 | Bayer Ag | New holographic recording material |
DE19910248A1 (en) | 1999-03-08 | 2000-10-05 | Bayer Ag | Holographic recording material |
DE19914325C1 (en) * | 1999-03-30 | 2000-07-06 | Bayer Ag | Rewritable optical recording material, for use with blue laser, contains polymeric azo dye giving optically induced birefringence |
US6501571B1 (en) | 1999-04-12 | 2002-12-31 | The Regents Of The University Of California | Three-dimensional holographic stamping of multi-layer bit-oriented non-linear optical media |
ES2241606T3 (en) * | 1999-06-03 | 2005-11-01 | Tokuyama Corporation | CHROME COMPOUNDS. |
US6322931B1 (en) * | 1999-07-29 | 2001-11-27 | Siros Technologies, Inc. | Method and apparatus for optical data storage using non-linear heating by excited state absorption for the alteration of pre-formatted holographic gratings |
US6512606B1 (en) * | 1999-07-29 | 2003-01-28 | Siros Technologies, Inc. | Optical storage media and method for optical data storage via local changes in reflectivity of a format grating |
DE10027152A1 (en) | 2000-05-31 | 2001-12-13 | Bayer Ag | Moschpolymers for optical data storage |
DE10027153A1 (en) * | 2000-05-31 | 2001-12-06 | Bayer Ag | Block polymer, useful for optical elements and data storage contains a block comprising at least 3 repeating units not containing photoisomerizable groups and a block containing STQP groups |
US6348983B1 (en) | 2000-06-08 | 2002-02-19 | Lucent Technologies Inc. | Holographic storage medium having enhanced temperature operating range and method of manufacturing the same |
US7005229B2 (en) * | 2002-10-02 | 2006-02-28 | 3M Innovative Properties Company | Multiphoton photosensitization method |
DE60120432T2 (en) | 2000-08-28 | 2007-01-04 | Aprilis, Inc., Maynard | HOLOGRAPHIC STORAGE MEDIUM CONTAINING POLYFUNCTIONAL EPOXY MONOMERS CAPABLE OF CATIONIC POLYMERIZATION |
US6733950B2 (en) * | 2001-03-14 | 2004-05-11 | General Electric Company | Limited play data storage media and method for limiting access to data thereon |
US6909684B2 (en) * | 2001-03-22 | 2005-06-21 | Fuji Xerox Co., Ltd. | Optical recording medium, holographic recording and/or retrieval method and holographic recording and/or retrieval apparatus |
CN1332377C (en) * | 2001-06-05 | 2007-08-15 | 自由播放技术公司 | Limited play optical devices with interstitial reactive layer and methods of making same |
US7026029B2 (en) * | 2001-06-05 | 2006-04-11 | Lindholm Edward P | Reactive materials for limited play optical devices and methods of making same |
WO2002102923A1 (en) * | 2001-06-15 | 2002-12-27 | Mitsubishi Chem Corp | Photochromic material and color dose meter using the same |
US6743552B2 (en) * | 2001-08-07 | 2004-06-01 | Inphase Technologies, Inc. | Process and composition for rapid mass production of holographic recording article |
KR100482654B1 (en) * | 2001-09-18 | 2005-04-13 | 한국화학연구원 | Photochromic nanocapsule and preparation method thereof |
US20030199603A1 (en) * | 2002-04-04 | 2003-10-23 | 3M Innovative Properties Company | Cured compositions transparent to ultraviolet radiation |
US20030206320A1 (en) * | 2002-04-11 | 2003-11-06 | Inphase Technologies, Inc. | Holographic media with a photo-active material for media protection and inhibitor removal |
AU2003232437A1 (en) | 2002-05-29 | 2003-12-19 | Inphase Technologies, Inc. | High reflective index photoactive compound for optical applications |
JP4237559B2 (en) * | 2003-06-30 | 2009-03-11 | 株式会社東芝 | Electronics |
US20060078802A1 (en) * | 2004-10-13 | 2006-04-13 | Chan Kwok P | Holographic storage medium |
US20070146835A1 (en) * | 2005-10-27 | 2007-06-28 | General Electric Company | Methods for making holographic data storage articles |
US7524590B2 (en) * | 2005-12-07 | 2009-04-28 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
US20070147214A1 (en) * | 2005-12-22 | 2007-06-28 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
US20070178404A1 (en) * | 2006-01-30 | 2007-08-02 | International Business Machines Corporation | Methods of preventing defects in antireflective coatings |
US20080055686A1 (en) * | 2006-09-05 | 2008-03-06 | Christoph Georg Erben | Holographic data recording method and system |
US20080084592A1 (en) * | 2006-10-09 | 2008-04-10 | General Electric Company | Molded Article Incorporating Volume Hologram |
US20080085455A1 (en) * | 2006-10-10 | 2008-04-10 | General Electric Company | Methods for storing holographic data and storage media derived therefrom |
-
2004
- 2004-09-30 US US10/954,779 patent/US7897296B2/en not_active Expired - Fee Related
-
2005
- 2005-09-16 EP EP05798422A patent/EP1797557A1/en not_active Withdrawn
- 2005-09-16 JP JP2007534640A patent/JP2008515023A/en active Pending
- 2005-09-16 WO PCT/US2005/033438 patent/WO2006039130A1/en active Application Filing
Patent Citations (6)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US5023859A (en) * | 1988-03-30 | 1991-06-11 | Rohm Gmbh Chemische Fabrik | Optical data storage apparatus and method utilizing an amorphous polymer which exhibits photochromic properties |
EP0566233A1 (en) * | 1992-02-27 | 1993-10-20 | SHARP Corporation | Optical memory medium and a method of recording information on the same |
US5443940A (en) * | 1992-04-16 | 1995-08-22 | Sanyo Electric Co., Ltd. | Optical recording material and optical recording medium employing the same |
US6046925A (en) * | 1997-04-14 | 2000-04-04 | The Regents Of The University Of California | Photochromic fluorescent proteins and optical memory storage devices based on fluorescent proteins |
WO2001037266A1 (en) * | 1999-11-17 | 2001-05-25 | The Research Foundation Of State University Of New York | Three dimensional data storage device and method for reading |
US20040072100A1 (en) * | 2002-09-04 | 2004-04-15 | Toshiko Mizokuro | Optical recording medium, production method thereof and method of using same |
Non-Patent Citations (1)
Title |
---|
See also references of EP1797557A1 * |
Cited By (25)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
WO2007050354A2 (en) * | 2005-10-27 | 2007-05-03 | General Electric Company | Methods for making holographic data storage articles |
WO2007050354A3 (en) * | 2005-10-27 | 2007-10-18 | Gen Electric | Methods for making holographic data storage articles |
US7794896B2 (en) | 2005-10-27 | 2010-09-14 | General Electric Company | Methods for making holographic data storage articles |
JP2009514019A (en) * | 2005-10-27 | 2009-04-02 | ゼネラル・エレクトリック・カンパニイ | Method for manufacturing holographic data storage article |
WO2007067670A2 (en) * | 2005-12-07 | 2007-06-14 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
WO2007067670A3 (en) * | 2005-12-07 | 2008-12-04 | Gen Electric | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
US7524590B2 (en) | 2005-12-07 | 2009-04-28 | General Electric Company | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom |
JP2008224834A (en) * | 2007-03-09 | 2008-09-25 | Adeka Corp | Composition for optical recording medium, and recording/display medium |
US7572560B2 (en) | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless reimageable printing paper and method |
US7645558B2 (en) | 2007-06-13 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US7553603B2 (en) | 2007-06-13 | 2009-06-30 | Xerox Corporation | Inkless printing paper and method |
US7569316B2 (en) | 2007-06-13 | 2009-08-04 | Xerox Corporation | Inkless reimageable printing paper and method |
US7541119B2 (en) | 2007-06-13 | 2009-06-02 | Xerox Corporation | Inkless reimageable printing paper and method |
US7572569B2 (en) | 2007-06-13 | 2009-08-11 | Xerox Corporation | Inkless printing paper and method |
US7582398B2 (en) | 2007-06-13 | 2009-09-01 | Xerox Corporation | Inkless reimageable printing paper and method |
US7588878B2 (en) | 2007-06-13 | 2009-09-15 | Xerox Corporation | Inkless printing paper and method |
US7867672B2 (en) | 2007-06-13 | 2011-01-11 | Xerox Corporation | Reimageable paper protected against UV light |
US7852366B2 (en) | 2007-06-13 | 2010-12-14 | Xerox Corporation | System and method for printing reimageable transient documents |
US7655366B2 (en) | 2007-06-13 | 2010-02-02 | Xerox Corporation | Inkless reimageable printing paper and method |
US7666558B2 (en) | 2007-06-13 | 2010-02-23 | Xerox Corporation | Inkless reimageable printing paper and method |
US7718325B2 (en) | 2007-06-13 | 2010-05-18 | Xerox Corporation | Photochromic material, inkless reimageable printing paper, and methods |
EP2003492A1 (en) | 2007-06-13 | 2008-12-17 | Xerox Corporation | Inkless Reimageable Printing Paper and Method |
WO2009072988A1 (en) * | 2007-12-07 | 2009-06-11 | Polycore Optical Pte Ltd | Encapsulated photochromic dyes |
US7645560B1 (en) | 2008-09-08 | 2010-01-12 | Xerox Corporation | Inkless reimageable printing paper and method |
US8715887B2 (en) | 2010-07-30 | 2014-05-06 | Sabic Innovative Plastics Ip B.V. | Complex holograms, method of making and using complex holograms |
Also Published As
Publication number | Publication date |
---|---|
JP2008515023A (en) | 2008-05-08 |
US20060073392A1 (en) | 2006-04-06 |
US7897296B2 (en) | 2011-03-01 |
EP1797557A1 (en) | 2007-06-20 |
Similar Documents
Publication | Publication Date | Title |
---|---|---|
US7897296B2 (en) | Method for holographic storage | |
JP4674673B2 (en) | Novel optical storage materials based on narrow-band optical properties | |
Bruder et al. | From the surface to volume: concepts for the next generation of optical–holographic data‐storage materials | |
US6322931B1 (en) | Method and apparatus for optical data storage using non-linear heating by excited state absorption for the alteration of pre-formatted holographic gratings | |
US8323854B2 (en) | Photopolymer media with enhanced dynamic range | |
US6512606B1 (en) | Optical storage media and method for optical data storage via local changes in reflectivity of a format grating | |
EP0969323B1 (en) | Material exhibiting compensation for polymerization-induced shrinkage and recording medium formed therefrom | |
TW200805359A (en) | Methods for storing holographic data and articles having enhanced data storage lifetime derived therefrom | |
US8232028B2 (en) | Holographic storage medium and method for gated diffusion of photoactive monomer | |
Ramanujam et al. | Physics and technology of optical storage in polymer thin films | |
JP2009514019A (en) | Method for manufacturing holographic data storage article | |
TW200837488A (en) | Method for storing holographic data | |
KR20120022066A (en) | Use of appended dyes in optical data storage media | |
KR20100074079A (en) | Data storage devices and methods | |
JP2014510308A (en) | Holographic storage medium and method for making holographic storage medium | |
WO2007124459A2 (en) | Index-contrasting-photoactive polymerizable materials, and articles and methods using same | |
TW201237860A (en) | Optical data storage media and methods for using the same | |
JP2009186515A (en) | Holographic recording medium, method for manufacturing holographic recording medium, and optical information recording and reproducing device | |
EP2661747B1 (en) | Method of making holographic recording materials and articles formed thereby | |
Samui | Holographic recording medium | |
Khan et al. | High-performance, nondiffusive crosslinked polymers for holographic data storage | |
US7852537B2 (en) | Optical recording medium and method of manufacturing the same | |
JP2010026450A (en) | Hologram recording medium and optical information recording and reproducing device | |
KR101124841B1 (en) | Novel optical storage materials based on narrowband optical properties | |
WO2024005139A1 (en) | Method for producing optical element |
Legal Events
Date | Code | Title | Description |
---|---|---|---|
AK | Designated states |
Kind code of ref document: A1 Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV LY MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW |
|
AL | Designated countries for regional patents |
Kind code of ref document: A1 Designated state(s): BW GH GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU LV MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG |
|
121 | Ep: the epo has been informed by wipo that ep was designated in this application | ||
WWE | Wipo information: entry into national phase |
Ref document number: 2007534640 Country of ref document: JP |
|
NENP | Non-entry into the national phase |
Ref country code: DE |
|
WWE | Wipo information: entry into national phase |
Ref document number: 2005798422 Country of ref document: EP |
|
WWP | Wipo information: published in national office |
Ref document number: 2005798422 Country of ref document: EP |