TWI251000B - Holographic storage medium comprising polyfunctional epoxy monomers capable of undergoing cationic polymerization - Google Patents
Holographic storage medium comprising polyfunctional epoxy monomers capable of undergoing cationic polymerization Download PDFInfo
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- TWI251000B TWI251000B TW090121147A TW90121147A TWI251000B TW I251000 B TWI251000 B TW I251000B TW 090121147 A TW090121147 A TW 090121147A TW 90121147 A TW90121147 A TW 90121147A TW I251000 B TWI251000 B TW I251000B
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- Prior art keywords
- group
- substituted
- aryl
- unsubstituted
- alkyl
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- 239000000178 monomer Substances 0.000 title claims abstract description 123
- 239000004593 Epoxy Substances 0.000 title claims abstract description 40
- 238000010538 cationic polymerization reaction Methods 0.000 title claims abstract description 28
- 238000003860 storage Methods 0.000 title description 4
- 150000002118 epoxides Chemical class 0.000 claims abstract description 67
- 239000002253 acid Substances 0.000 claims abstract description 47
- 239000011230 binding agent Substances 0.000 claims abstract description 30
- 230000005855 radiation Effects 0.000 claims abstract description 23
- 229910052710 silicon Inorganic materials 0.000 claims abstract description 3
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims abstract 2
- 125000003118 aryl group Chemical group 0.000 claims description 105
- 125000000217 alkyl group Chemical group 0.000 claims description 56
- -1 alkyl decane Chemical compound 0.000 claims description 49
- 125000001931 aliphatic group Chemical group 0.000 claims description 40
- 150000001875 compounds Chemical class 0.000 claims description 31
- 125000002947 alkylene group Chemical group 0.000 claims description 29
- DIOQZVSQGTUSAI-UHFFFAOYSA-N n-butylhexane Natural products CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 claims description 28
- 125000000753 cycloalkyl group Chemical group 0.000 claims description 25
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 claims description 25
- 239000001257 hydrogen Substances 0.000 claims description 19
- 229910052739 hydrogen Inorganic materials 0.000 claims description 19
- 125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 18
- 125000005647 linker group Chemical group 0.000 claims description 17
- 125000003342 alkenyl group Chemical group 0.000 claims description 13
- 125000004432 carbon atom Chemical group C* 0.000 claims description 12
- 125000002993 cycloalkylene group Chemical group 0.000 claims description 12
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 claims description 11
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 9
- KJTLSVCANCCWHF-UHFFFAOYSA-N Ruthenium Chemical group [Ru] KJTLSVCANCCWHF-UHFFFAOYSA-N 0.000 claims description 8
- 229910052707 ruthenium Inorganic materials 0.000 claims description 8
- 239000000853 adhesive Substances 0.000 claims description 7
- 230000001070 adhesive effect Effects 0.000 claims description 7
- 150000001335 aliphatic alkanes Chemical class 0.000 claims description 7
- KWKAKUADMBZCLK-UHFFFAOYSA-N 1-octene Chemical group CCCCCCC=C KWKAKUADMBZCLK-UHFFFAOYSA-N 0.000 claims description 6
- 125000003107 substituted aryl group Chemical group 0.000 claims description 6
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 claims description 6
- 150000005215 alkyl ethers Chemical class 0.000 claims description 5
- QVGXLLKOCUKJST-UHFFFAOYSA-N atomic oxygen Chemical group [O] QVGXLLKOCUKJST-UHFFFAOYSA-N 0.000 claims description 5
- 125000001316 cycloalkyl alkyl group Chemical group 0.000 claims description 5
- 125000006612 decyloxy group Chemical group 0.000 claims description 5
- 125000000816 ethylene group Chemical group [H]C([H])([*:1])C([H])([H])[*:2] 0.000 claims description 5
- NIHNNTQXNPWCJQ-UHFFFAOYSA-N fluorene Chemical compound C1=CC=C2CC3=CC=CC=C3C2=C1 NIHNNTQXNPWCJQ-UHFFFAOYSA-N 0.000 claims description 5
- 239000007789 gas Substances 0.000 claims description 5
- 125000004051 hexyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 5
- 239000001301 oxygen Substances 0.000 claims description 5
- 229910052760 oxygen Inorganic materials 0.000 claims description 5
- 150000003839 salts Chemical class 0.000 claims description 5
- 239000004576 sand Substances 0.000 claims description 5
- 229920002554 vinyl polymer Polymers 0.000 claims description 5
- 125000000732 arylene group Chemical group 0.000 claims description 4
- 150000001983 dialkylethers Chemical class 0.000 claims description 4
- 125000004836 hexamethylene group Chemical group [H]C([H])([*:2])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[*:1] 0.000 claims description 4
- 125000000466 oxiranyl group Chemical group 0.000 claims description 4
- 125000005188 oxoalkyl group Chemical group 0.000 claims description 4
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 claims description 3
- 125000003710 aryl alkyl group Chemical group 0.000 claims description 3
- 239000003795 chemical substances by application Substances 0.000 claims description 3
- 125000002704 decyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 claims description 3
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 2
- 150000002923 oximes Chemical class 0.000 claims description 2
- 238000006467 substitution reaction Methods 0.000 claims description 2
- PCTMTFRHKVHKIS-BMFZQQSSSA-N (1s,3r,4e,6e,8e,10e,12e,14e,16e,18s,19r,20r,21s,25r,27r,30r,31r,33s,35r,37s,38r)-3-[(2r,3s,4s,5s,6r)-4-amino-3,5-dihydroxy-6-methyloxan-2-yl]oxy-19,25,27,30,31,33,35,37-octahydroxy-18,20,21-trimethyl-23-oxo-22,39-dioxabicyclo[33.3.1]nonatriaconta-4,6,8,10 Chemical compound C1C=C2C[C@@H](OS(O)(=O)=O)CC[C@]2(C)[C@@H]2[C@@H]1[C@@H]1CC[C@H]([C@H](C)CCCC(C)C)[C@@]1(C)CC2.O[C@H]1[C@@H](N)[C@H](O)[C@@H](C)O[C@H]1O[C@H]1/C=C/C=C/C=C/C=C/C=C/C=C/C=C/[C@H](C)[C@@H](O)[C@@H](C)[C@H](C)OC(=O)C[C@H](O)C[C@H](O)CC[C@@H](O)[C@H](O)C[C@H](O)C[C@](O)(C[C@H](O)[C@H]2C(O)=O)O[C@H]2C1 PCTMTFRHKVHKIS-BMFZQQSSSA-N 0.000 claims 6
- OUHYGBCAEPBUNA-UHFFFAOYSA-N 5,12-bis(phenylethynyl)naphthacene Chemical group C1=CC=CC=C1C#CC(C1=CC2=CC=CC=C2C=C11)=C(C=CC=C2)C2=C1C#CC1=CC=CC=C1 OUHYGBCAEPBUNA-UHFFFAOYSA-N 0.000 claims 3
- 229910052799 carbon Inorganic materials 0.000 claims 2
- 150000003254 radicals Chemical class 0.000 claims 2
- 239000005977 Ethylene Substances 0.000 claims 1
- DHXVGJBLRPWPCS-UHFFFAOYSA-N Tetrahydropyran Chemical compound C1CCOCC1 DHXVGJBLRPWPCS-UHFFFAOYSA-N 0.000 claims 1
- 125000005011 alkyl ether group Chemical group 0.000 claims 1
- 210000000078 claw Anatomy 0.000 claims 1
- 150000001924 cycloalkanes Chemical class 0.000 claims 1
- 150000001925 cycloalkenes Chemical class 0.000 claims 1
- 239000004744 fabric Substances 0.000 claims 1
- 125000000472 sulfonyl group Chemical group *S(*)(=O)=O 0.000 claims 1
- 229910021653 sulphate ion Inorganic materials 0.000 claims 1
- XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical group [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 abstract 1
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 39
- 239000000463 material Substances 0.000 description 23
- 238000006243 chemical reaction Methods 0.000 description 20
- 238000000034 method Methods 0.000 description 20
- 239000000203 mixture Substances 0.000 description 19
- 238000006116 polymerization reaction Methods 0.000 description 17
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920000642 polymer Polymers 0.000 description 10
- XKRFYHLGVUSROY-UHFFFAOYSA-N argon Substances [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 description 9
- 230000015572 biosynthetic process Effects 0.000 description 9
- 239000003610 charcoal Substances 0.000 description 9
- 239000000126 substance Substances 0.000 description 9
- 238000004458 analytical method Methods 0.000 description 8
- 239000003054 catalyst Substances 0.000 description 8
- 125000003187 heptyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 8
- 239000008240 homogeneous mixture Substances 0.000 description 8
- 230000035945 sensitivity Effects 0.000 description 8
- 239000000243 solution Substances 0.000 description 8
- 238000001914 filtration Methods 0.000 description 7
- 239000011541 reaction mixture Substances 0.000 description 7
- 238000003786 synthesis reaction Methods 0.000 description 7
- 239000003039 volatile agent Substances 0.000 description 7
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 6
- 238000005033 Fourier transform infrared spectroscopy Methods 0.000 description 6
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 description 6
- 229910052786 argon Inorganic materials 0.000 description 6
- 230000001186 cumulative effect Effects 0.000 description 6
- 238000013500 data storage Methods 0.000 description 6
- 238000011161 development Methods 0.000 description 6
- 230000008859 change Effects 0.000 description 5
- 238000000113 differential scanning calorimetry Methods 0.000 description 5
- 239000003822 epoxy resin Substances 0.000 description 5
- 238000005984 hydrogenation reaction Methods 0.000 description 5
- 230000003287 optical effect Effects 0.000 description 5
- 229920000647 polyepoxide Polymers 0.000 description 5
- 230000008569 process Effects 0.000 description 5
- 238000000926 separation method Methods 0.000 description 5
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- 230000005540 biological transmission Effects 0.000 description 4
- 230000000694 effects Effects 0.000 description 4
- 239000011261 inert gas Substances 0.000 description 4
- 238000002360 preparation method Methods 0.000 description 4
- 230000009467 reduction Effects 0.000 description 4
- 239000000523 sample Substances 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- KZQARKMUPDKYPY-UHFFFAOYSA-N C(=C)C(C(OCCCCCCCCCC)(C)C)CCCCCCCC.NN Chemical compound C(=C)C(C(OCCCCCCCCCC)(C)C)CCCCCCCC.NN KZQARKMUPDKYPY-UHFFFAOYSA-N 0.000 description 3
- 238000004566 IR spectroscopy Methods 0.000 description 3
- 239000012298 atmosphere Substances 0.000 description 3
- 230000008602 contraction Effects 0.000 description 3
- 239000012467 final product Substances 0.000 description 3
- 238000004817 gas chromatography Methods 0.000 description 3
- 238000003384 imaging method Methods 0.000 description 3
- 229910052757 nitrogen Inorganic materials 0.000 description 3
- 238000010526 radical polymerization reaction Methods 0.000 description 3
- 238000004809 thin layer chromatography Methods 0.000 description 3
- RIOQSEWOXXDEQQ-UHFFFAOYSA-N triphenylphosphine Chemical compound C1=CC=CC=C1P(C=1C=CC=CC=1)C1=CC=CC=C1 RIOQSEWOXXDEQQ-UHFFFAOYSA-N 0.000 description 3
- LWNGJAHMBMVCJR-UHFFFAOYSA-N (2,3,4,5,6-pentafluorophenoxy)boronic acid Chemical compound OB(O)OC1=C(F)C(F)=C(F)C(F)=C1F LWNGJAHMBMVCJR-UHFFFAOYSA-N 0.000 description 2
- BDAGIAXQQBRORQ-UHFFFAOYSA-N 1,2,3,3a,4,5-hexahydroacenaphthylene Chemical compound C1CCC2CCC3=CC=CC1=C32 BDAGIAXQQBRORQ-UHFFFAOYSA-N 0.000 description 2
- AZQWKYJCGOJGHM-UHFFFAOYSA-N 1,4-benzoquinone Chemical compound O=C1C=CC(=O)C=C1 AZQWKYJCGOJGHM-UHFFFAOYSA-N 0.000 description 2
- RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 2
- KHNDTMXLUDWGOU-UHFFFAOYSA-N [Pt].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Ru] Chemical compound [Pt].C1(=CC=CC=C1)P(C1=CC=CC=C1)C1=CC=CC=C1.[Ru] KHNDTMXLUDWGOU-UHFFFAOYSA-N 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000004364 calculation method Methods 0.000 description 2
- 238000005336 cracking Methods 0.000 description 2
- 125000004122 cyclic group Chemical group 0.000 description 2
- 230000007547 defect Effects 0.000 description 2
- 150000001993 dienes Chemical class 0.000 description 2
- 230000001747 exhibiting effect Effects 0.000 description 2
- 238000002474 experimental method Methods 0.000 description 2
- 230000006870 function Effects 0.000 description 2
- 238000005286 illumination Methods 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
- BASFCYQUMIYNBI-UHFFFAOYSA-N platinum Chemical compound [Pt] BASFCYQUMIYNBI-UHFFFAOYSA-N 0.000 description 2
- 239000002243 precursor Substances 0.000 description 2
- 238000011160 research Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 125000001424 substituent group Chemical group 0.000 description 2
- PSGCQDPCAWOCSH-UHFFFAOYSA-N (4,7,7-trimethyl-3-bicyclo[2.2.1]heptanyl) prop-2-enoate Chemical compound C1CC2(C)C(OC(=O)C=C)CC1C2(C)C PSGCQDPCAWOCSH-UHFFFAOYSA-N 0.000 description 1
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 1
- WQUNVSNKFICLRQ-UHFFFAOYSA-N 2-methylundecan-2-ol Chemical compound CCCCCCCCCC(C)(C)O WQUNVSNKFICLRQ-UHFFFAOYSA-N 0.000 description 1
- NIXOWILDQLNWCW-UHFFFAOYSA-M Acrylate Chemical compound [O-]C(=O)C=C NIXOWILDQLNWCW-UHFFFAOYSA-M 0.000 description 1
- 239000002028 Biomass Substances 0.000 description 1
- 125000006539 C12 alkyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- FKUZOZILINIPON-UHFFFAOYSA-N CC(CCCCCCCCC)(OCCCCCCCCCC)C Chemical compound CC(CCCCCCCCC)(OCCCCCCCCCC)C FKUZOZILINIPON-UHFFFAOYSA-N 0.000 description 1
- 244000025254 Cannabis sativa Species 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 239000002841 Lewis acid Substances 0.000 description 1
- ANBQUTAIMGLFJM-UHFFFAOYSA-N OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F.C(C=C1)=CC=C1PC1=CC=CC=C1.C(C=C1)=CC=C1PC1=CC=CC=C1 Chemical compound OB(O)OC(C(F)=C(C(F)=C1F)F)=C1F.C(C=C1)=CC=C1PC1=CC=CC=C1.C(C=C1)=CC=C1PC1=CC=CC=C1 ANBQUTAIMGLFJM-UHFFFAOYSA-N 0.000 description 1
- 150000001252 acrylic acid derivatives Chemical class 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 238000005804 alkylation reaction Methods 0.000 description 1
- 125000000304 alkynyl group Chemical group 0.000 description 1
- 238000004873 anchoring Methods 0.000 description 1
- 238000000149 argon plasma sintering Methods 0.000 description 1
- 150000004945 aromatic hydrocarbons Chemical group 0.000 description 1
- 125000004429 atom Chemical group 0.000 description 1
- ICCBZGUDUOMNOF-UHFFFAOYSA-N azidoamine Chemical compound NN=[N+]=[N-] ICCBZGUDUOMNOF-UHFFFAOYSA-N 0.000 description 1
- 230000008901 benefit Effects 0.000 description 1
- 125000006267 biphenyl group Chemical group 0.000 description 1
- 230000015556 catabolic process Effects 0.000 description 1
- 238000012656 cationic ring opening polymerization Methods 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 230000003750 conditioning effect Effects 0.000 description 1
- ZWAJLVLEBYIOTI-UHFFFAOYSA-N cyclohexene oxide Chemical compound C1CCCC2OC21 ZWAJLVLEBYIOTI-UHFFFAOYSA-N 0.000 description 1
- FWFSEYBSWVRWGL-UHFFFAOYSA-N cyclohexene oxide Natural products O=C1CCCC=C1 FWFSEYBSWVRWGL-UHFFFAOYSA-N 0.000 description 1
- 238000006731 degradation reaction Methods 0.000 description 1
- 230000001419 dependent effect Effects 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000009792 diffusion process Methods 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 238000005516 engineering process Methods 0.000 description 1
- 125000003700 epoxy group Chemical group 0.000 description 1
- 238000011049 filling Methods 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000002367 halogens Chemical class 0.000 description 1
- AETGYOWKOXPRCB-UHFFFAOYSA-N heptylhydrazine Chemical compound CCCCCCCNN AETGYOWKOXPRCB-UHFFFAOYSA-N 0.000 description 1
- 125000001072 heteroaryl group Chemical group 0.000 description 1
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- JEIPFZHSYJVQDO-UHFFFAOYSA-N iron(III) oxide Inorganic materials O=[Fe]O[Fe]=O JEIPFZHSYJVQDO-UHFFFAOYSA-N 0.000 description 1
- 125000001449 isopropyl group Chemical group [H]C([H])([H])C([H])(*)C([H])([H])[H] 0.000 description 1
- 150000002576 ketones Chemical class 0.000 description 1
- 150000007517 lewis acids Chemical class 0.000 description 1
- 230000031700 light absorption Effects 0.000 description 1
- 239000007788 liquid Substances 0.000 description 1
- 230000007774 longterm Effects 0.000 description 1
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- 238000005259 measurement Methods 0.000 description 1
- 229910052751 metal Inorganic materials 0.000 description 1
- 239000002184 metal Substances 0.000 description 1
- 125000001570 methylene group Chemical group [H]C([H])([*:1])[*:2] 0.000 description 1
- 238000012544 monitoring process Methods 0.000 description 1
- 125000004108 n-butyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- 125000004123 n-propyl group Chemical group [H]C([H])([H])C([H])([H])C([H])([H])* 0.000 description 1
- KKFHAJHLJHVUDM-UHFFFAOYSA-N n-vinylcarbazole Chemical compound C1=CC=C2N(C=C)C3=CC=CC=C3C2=C1 KKFHAJHLJHVUDM-UHFFFAOYSA-N 0.000 description 1
- 125000001624 naphthyl group Chemical group 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
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- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
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- YYMBJDOZVAITBP-UHFFFAOYSA-N rubrene Chemical compound C1=CC=CC=C1C(C1=C(C=2C=CC=CC=2)C2=CC=CC=C2C(C=2C=CC=CC=2)=C11)=C(C=CC=C2)C2=C1C1=CC=CC=C1 YYMBJDOZVAITBP-UHFFFAOYSA-N 0.000 description 1
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- 230000001568 sexual effect Effects 0.000 description 1
- 241000894007 species Species 0.000 description 1
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- QAOWNCQODCNURD-UHFFFAOYSA-L sulfate group Chemical group S(=O)(=O)([O-])[O-] QAOWNCQODCNURD-UHFFFAOYSA-L 0.000 description 1
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- 229920001897 terpolymer Polymers 0.000 description 1
- 125000000999 tert-butyl group Chemical group [H]C([H])([H])C(*)(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
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- ANEFWEBMQHRDLH-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl) borate Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1OB(OC=1C(=C(F)C(F)=C(F)C=1F)F)OC1=C(F)C(F)=C(F)C(F)=C1F ANEFWEBMQHRDLH-UHFFFAOYSA-N 0.000 description 1
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- 239000010803 wood ash Substances 0.000 description 1
Classifications
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/32—Epoxy compounds containing three or more epoxy groups
- C08G59/3254—Epoxy compounds containing three or more epoxy groups containing atoms other than carbon, hydrogen, oxygen or nitrogen
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/04—Polysiloxanes
- C08G77/14—Polysiloxanes containing silicon bound to oxygen-containing groups
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G77/00—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule
- C08G77/48—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms
- C08G77/50—Macromolecular compounds obtained by reactions forming a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon in the main chain of the macromolecule in which at least two but not all the silicon atoms are connected by linkages other than oxygen atoms by carbon linkages
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/0005—Production of optical devices or components in so far as characterised by the lithographic processes or materials used therefor
- G03F7/001—Phase modulating patterns, e.g. refractive index patterns
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0755—Non-macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03F—PHOTOMECHANICAL PRODUCTION OF TEXTURED OR PATTERNED SURFACES, e.g. FOR PRINTING, FOR PROCESSING OF SEMICONDUCTOR DEVICES; MATERIALS THEREFOR; ORIGINALS THEREFOR; APPARATUS SPECIALLY ADAPTED THEREFOR
- G03F7/00—Photomechanical, e.g. photolithographic, production of textured or patterned surfaces, e.g. printing surfaces; Materials therefor, e.g. comprising photoresists; Apparatus specially adapted therefor
- G03F7/004—Photosensitive materials
- G03F7/075—Silicon-containing compounds
- G03F7/0757—Macromolecular compounds containing Si-O, Si-C or Si-N bonds
-
- 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
-
- 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
- G11B7/2403—Layers; Shape, structure or physical properties thereof
- G11B7/24035—Recording layers
- G11B7/24044—Recording layers for storing optical interference patterns, e.g. holograms; for storing data in three dimensions, e.g. volume storage
-
- 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
- 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
-
- G—PHYSICS
- G03—PHOTOGRAPHY; CINEMATOGRAPHY; ANALOGOUS TECHNIQUES USING WAVES OTHER THAN OPTICAL WAVES; ELECTROGRAPHY; HOLOGRAPHY
- G03H—HOLOGRAPHIC PROCESSES OR APPARATUS
- G03H2260/00—Recording materials or recording processes
- G03H2260/12—Photopolymer
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- Chemical & Material Sciences (AREA)
- Physics & Mathematics (AREA)
- General Physics & Mathematics (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Spectroscopy & Molecular Physics (AREA)
- Holo Graphy (AREA)
- Epoxy Resins (AREA)
Applications Claiming Priority (1)
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| US22812100P | 2000-08-28 | 2000-08-28 |
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| TW090121147A TWI251000B (en) | 2000-08-28 | 2001-08-28 | Holographic storage medium comprising polyfunctional epoxy monomers capable of undergoing cationic polymerization |
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| DE (1) | DE60120432T2 (enExample) |
| TW (1) | TWI251000B (enExample) |
| WO (1) | WO2002019040A2 (enExample) |
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| JP2003534569A (ja) * | 2000-05-23 | 2003-11-18 | アプリリス，インコーポレイテッド | コロイド状金属を含むデータ保存媒体とその製造方法 |
| AU2001286860A1 (en) * | 2000-08-28 | 2002-03-13 | Aprilis, Inc. | Holographic storage medium comprising polyfunctional epoxy monomers capable of undergoing cationic polymerization |
| US20060128822A1 (en) * | 2002-07-30 | 2006-06-15 | Toagosei Co., Ltd. | Composition for holography, method of curing the same, and cured article |
| EP1554614A4 (en) | 2002-10-22 | 2008-08-27 | Zebra Imaging Inc | ACTIVE DISPLAY OF DIGITAL HOLOGRAMS |
| WO2004059389A2 (en) | 2002-12-23 | 2004-07-15 | Aprilis, Inc. | Sensitizer dyes for photoacid generating systems |
| US20050187308A1 (en) * | 2004-02-20 | 2005-08-25 | Korea Advanced Institute Of Science And Technology | Method of preparing photopolymer with enhanced optical quality using nanoporous membrane and photopolymer prepared by the same |
| US20070260089A1 (en) * | 2004-03-26 | 2007-11-08 | Albemarle Corporation | Method for the Synthesis of Quaternary Ammonium Compounds and Compositions Thereof |
| JP4629367B2 (ja) * | 2004-05-31 | 2011-02-09 | 東レ・ダウコーニング株式会社 | 活性エネルギー線硬化型オルガノポリシロキサン樹脂組成物、光伝送部材およびその製造方法 |
| US7122290B2 (en) * | 2004-06-15 | 2006-10-17 | General Electric Company | Holographic storage medium |
| US7111806B2 (en) | 2004-08-05 | 2006-09-26 | Esselte | Spool for supply of image receiving medium |
| US7897296B2 (en) * | 2004-09-30 | 2011-03-01 | General Electric Company | Method for holographic storage |
| US20060078802A1 (en) * | 2004-10-13 | 2006-04-13 | Chan Kwok P | Holographic storage medium |
| US20060199081A1 (en) * | 2005-03-04 | 2006-09-07 | General Electric Company | Holographic storage medium, article and method |
| US8034514B2 (en) * | 2005-03-08 | 2011-10-11 | Nippon Steel Chemical Co., Ltd. | Photosensitive resin composition for volume phase hologram recording and optical information recording medium using the same |
| WO2007047840A2 (en) * | 2005-10-18 | 2007-04-26 | Dce Aprilis, Inc. | Photopolymerizable medium comprising siloxane compounds that support cationic polymerization for holographic storage |
| US20070167407A1 (en) * | 2005-12-20 | 2007-07-19 | Albemarle Corporation | Quaternary ammonium borate compositions and substrate preservative solutions containing them |
| US7964693B2 (en) * | 2005-12-29 | 2011-06-21 | The University Of Akron | Photocurable polymers for ophthalmic applications |
| US8163443B2 (en) * | 2006-03-09 | 2012-04-24 | Nippon Steel Chemical Co., Ltd. | Photosensitive resin composition for volume phase hologram recording and optical information recording medium using the same |
| WO2007120628A2 (en) * | 2006-04-11 | 2007-10-25 | Dow Corning Corporation | A composition including a siloxane and a method of forming the same |
| US20070248890A1 (en) * | 2006-04-20 | 2007-10-25 | Inphase Technologies, Inc. | Index Contrasting-Photoactive Polymerizable Materials, and Articles and Methods Using Same |
| JP2008195616A (ja) | 2007-02-08 | 2008-08-28 | Fujifilm Corp | 重合性化合物、光記録用組成物、ホログラフィック記録媒体および情報記録方法 |
| BRPI0810155A2 (pt) | 2007-04-11 | 2014-12-30 | Bayer Materialscience Ag | Meios de gravação para aplicações holográficas. |
| JP2010202801A (ja) * | 2009-03-04 | 2010-09-16 | Nitto Denko Corp | 熱硬化性シリコーン樹脂用組成物 |
| WO2010107784A1 (en) | 2009-03-16 | 2010-09-23 | Stx Aprilis, Inc. | Methods for activation control of photopolymerization for holographic data storage using at least two wavelengths |
| US8323854B2 (en) * | 2009-04-23 | 2012-12-04 | Akonia Holographics, Llc | Photopolymer media with enhanced dynamic range |
| KR101426629B1 (ko) | 2009-11-25 | 2014-08-05 | 다이니치 세이카 고교 가부시키가이샤 | 폴리실록산 변성 폴리히드록시 폴리우레탄 수지 및 그 제조방법, 상기 수지를 이용한 감열 기록 재료, 인조 피혁, 열가소성 폴리올레핀 수지 표피재, 웨더스트립용 재료 및 웨더스트립 |
| JP2011132208A (ja) * | 2009-11-25 | 2011-07-07 | Dainichiseika Color & Chem Mfg Co Ltd | ５員環環状カーボネートポリシロキサン化合物およびその製造方法 |
| WO2011065433A1 (ja) | 2009-11-26 | 2011-06-03 | 大日精化工業株式会社 | ポリシロキサン変性ポリヒドロキシポリウレタン樹脂及びその製造方法、該樹脂を用いた感熱記録材料、擬革、熱可塑性ポリオレフィン樹脂表皮材、ウェザーストリップ用材料及びウェザーストリップ |
| GB2476275A (en) | 2009-12-17 | 2011-06-22 | Dublin Inst Of Technology | Photosensitive holographic recording medium comprising glycerol |
| EP2586814B1 (en) | 2010-06-24 | 2016-01-20 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Self-crosslinkable polyhydroxy polyurethane resin, resinaceous material that contains the resin, process for production of the resin, and imitation leather, surfacing material and weatherstrip material, using the resin |
| WO2012026338A1 (ja) | 2010-08-26 | 2012-03-01 | 大日精化工業株式会社 | 自己架橋型ポリシロキサン変性ポリヒドロキシポリウレタン樹脂、該樹脂を含む樹脂材料、該樹脂の製造方法、該樹脂を用いてなる擬革及び熱可塑性ポリオレフィン表皮材 |
| WO2012137726A1 (ja) | 2011-04-04 | 2012-10-11 | 大日精化工業株式会社 | 自己架橋型ポリシロキサン変性ポリヒドロキシポリウレタン樹脂、該樹脂の製造方法、該樹脂を含む樹脂材料および該樹脂を利用した擬革 |
| KR20170016392A (ko) * | 2014-05-30 | 2017-02-13 | 다우 코닝 도레이 캄파니 리미티드 | 유기 규소 화합물, 경화성 실리콘 조성물, 및 반도체 장치 |
| US10150842B2 (en) * | 2014-12-19 | 2018-12-11 | Dow Silicones Corporation | Method of preparing condensation cross-linked particles |
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| BE655303A (enExample) * | 1963-11-12 | 1965-03-01 | ||
| JPS6017377B2 (ja) * | 1979-07-31 | 1985-05-02 | 信越化学工業株式会社 | 重合性オルガノポリシロキサンの製造方法 |
| US5037861A (en) | 1989-08-09 | 1991-08-06 | General Electric Company | Novel highly reactive silicon-containing epoxides |
| US5075154A (en) * | 1990-03-23 | 1991-12-24 | General Electric Company | UV-curable silphenylene-containing epoxy functional silicones |
| DE4023556A1 (de) * | 1990-07-25 | 1992-01-30 | Goldschmidt Ag Th | Haertbare epoxygruppen aufweisende organopolysiloxane, verfahren zu ihrer herstellung und ihre verwendung als haertbare beschichtungsmittel mit abhaesiven eigenschaften |
| JP3015139B2 (ja) * | 1991-04-23 | 2000-03-06 | 東レ・ダウコーニング・シリコーン株式会社 | オルガノポリシロキサンおよびその製造方法 |
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| US5484950A (en) | 1992-12-21 | 1996-01-16 | Polyset Company, Inc. | Process for selective monoaddition to silanes containing two silicon-hydrogen bonds and products thereof |
| US5292827A (en) * | 1993-02-25 | 1994-03-08 | General Electric Company | Epoxy-capped branched silicones and copolymers thereof |
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| WO1997013183A1 (en) | 1995-10-06 | 1997-04-10 | Polaroid Corporation | Holographic medium and process |
| US5863970A (en) * | 1995-12-06 | 1999-01-26 | Polyset Company, Inc. | Epoxy resin composition with cycloaliphatic epoxy-functional siloxane |
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| DE19648283A1 (de) * | 1996-11-21 | 1998-05-28 | Thera Ges Fuer Patente | Polymerisierbare Massen auf der Basis von Epoxiden |
| US20030157414A1 (en) * | 1997-11-13 | 2003-08-21 | Pradeep K. Dhal | Holographic medium and process for use thereof |
| US6391999B1 (en) * | 1998-02-06 | 2002-05-21 | Rensselaer Polytechnic Institute | Epoxy alkoxy siloxane oligomers |
| JP2003534569A (ja) * | 2000-05-23 | 2003-11-18 | アプリリス，インコーポレイテッド | コロイド状金属を含むデータ保存媒体とその製造方法 |
| US6852766B1 (en) * | 2000-06-15 | 2005-02-08 | 3M Innovative Properties Company | Multiphoton photosensitization system |
| AU2001286860A1 (en) | 2000-08-28 | 2002-03-13 | Aprilis, Inc. | Holographic storage medium comprising polyfunctional epoxy monomers capable of undergoing cationic polymerization |
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2001
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- 2001-08-28 WO PCT/US2001/026828 patent/WO2002019040A2/en not_active Ceased
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| AU2001286860A1 (en) | 2002-03-13 |
| DE60120432T2 (de) | 2007-01-04 |
| WO2002019040A9 (en) | 2002-07-25 |
| US7070886B2 (en) | 2006-07-04 |
| KR20030045790A (ko) | 2003-06-11 |
| CA2424366A1 (en) | 2002-03-07 |
| US20100280260A1 (en) | 2010-11-04 |
| EP1317498B1 (en) | 2006-06-07 |
| DE60120432D1 (de) | 2006-07-20 |
| JP2004507513A (ja) | 2004-03-11 |
| US20020068223A1 (en) | 2002-06-06 |
| EP1317498A2 (en) | 2003-06-11 |
| US20070293637A1 (en) | 2007-12-20 |
| US7332249B2 (en) | 2008-02-19 |
| KR100749304B1 (ko) | 2007-08-14 |
| WO2002019040A2 (en) | 2002-03-07 |
| US20040249181A1 (en) | 2004-12-09 |
| US6784300B2 (en) | 2004-08-31 |
| WO2002019040A3 (en) | 2002-05-30 |
| ATE328939T1 (de) | 2006-06-15 |
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