CA1216111A - Dispositif optique au polymere birefringent - Google Patents

Dispositif optique au polymere birefringent

Info

Publication number: CA1216111A
Authority: CA; Canada
Prior art keywords: hydrogen; radical; substituent; integer; formula
Prior art date: 1981-03-02
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired

Application number

CA000397302A

Other languages

English (en)

Inventor

Howard G. Rogers

Russell A. Gaudiana

Ruth C. Bilofsky

Palaiyur S. Kalyanaraman

Ronald A. Sahatjian

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Polaroid Corp

Original Assignee

Polaroid Corp

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1981-03-02

Filing date

1982-03-01

Publication date

1987-01-06

1981-03-02 Priority claimed from US06/238,054 external-priority patent/US4446305A/en

1981-03-02 Priority claimed from US06/239,180 external-priority patent/US4393194A/en

1982-03-01 Application filed by Polaroid Corp filed Critical Polaroid Corp

1987-01-06 Application granted granted Critical

1987-01-06 Publication of CA1216111A publication Critical patent/CA1216111A/fr

Status Expired legal-status Critical Current

Links

229920000642 polymer Polymers 0.000 title claims abstract description 228
230000003287 optical effect Effects 0.000 title claims abstract description 50
238000009826 distribution Methods 0.000 claims abstract description 18
239000000463 material Substances 0.000 claims description 184
229910052739 hydrogen Inorganic materials 0.000 claims description 158
239000001257 hydrogen Substances 0.000 claims description 158
125000001424 substituent group Chemical group 0.000 claims description 145
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 claims description 65
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 55
229910052736 halogen Inorganic materials 0.000 claims description 30
238000006467 substitution reaction Methods 0.000 claims description 28
125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 claims description 21
230000001747 exhibiting effect Effects 0.000 claims description 19
125000003545 alkoxy group Chemical group 0.000 claims description 18
125000005843 halogen group Chemical group 0.000 claims description 18
150000002367 halogens Chemical class 0.000 claims description 15
125000003118 aryl group Chemical group 0.000 claims description 12
125000000547 substituted alkyl group Chemical group 0.000 claims description 10
239000002861 polymer material Substances 0.000 claims description 8
125000002877 alkyl aryl group Chemical group 0.000 claims description 5
125000003710 aryl alkyl group Chemical group 0.000 claims description 5
150000002431 hydrogen Chemical class 0.000 claims 44
125000000449 nitro group Chemical group [O-][N+](*)=O 0.000 claims 14
125000001246 bromo group Chemical group Br* 0.000 claims 10
125000001153 fluoro group Chemical group F* 0.000 claims 3
125000000217 alkyl group Chemical group 0.000 claims 2
239000013078 crystal Substances 0.000 abstract description 6
KWGKDLIKAYFUFQ-UHFFFAOYSA-M lithium chloride Chemical compound [Li+].[Cl-] KWGKDLIKAYFUFQ-UHFFFAOYSA-M 0.000 description 236
239000010410 layer Substances 0.000 description 161
239000000243 solution Substances 0.000 description 146
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 90
238000006243 chemical reaction Methods 0.000 description 84
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 63
239000011541 reaction mixture Substances 0.000 description 60
239000002904 solvent Substances 0.000 description 55
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 54
229920002647 polyamide Polymers 0.000 description 54
239000004952 Polyamide Substances 0.000 description 53
FXHOOIRPVKKKFG-UHFFFAOYSA-N N,N-Dimethylacetamide Chemical compound CN(C)C(C)=O FXHOOIRPVKKKFG-UHFFFAOYSA-N 0.000 description 47
229940113088 dimethylacetamide Drugs 0.000 description 47
229910052757 nitrogen Inorganic materials 0.000 description 46
239000011521 glass Substances 0.000 description 45
238000003756 stirring Methods 0.000 description 44
238000002360 preparation method Methods 0.000 description 38
239000007787 solid Substances 0.000 description 36
239000000047 product Substances 0.000 description 35
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 30
239000000203 mixture Substances 0.000 description 26
241000282320 Panthera leo Species 0.000 description 24
230000000694 effects Effects 0.000 description 24
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238000000034 method Methods 0.000 description 23
-1 vinylene, ethynylene Chemical group 0.000 description 23
238000005266 casting Methods 0.000 description 19
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 19
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 18
238000004458 analytical method Methods 0.000 description 18
SECXISVLQFMRJM-UHFFFAOYSA-N N-Methylpyrrolidone Chemical compound CN1CCCC1=O SECXISVLQFMRJM-UHFFFAOYSA-N 0.000 description 16
239000010453 quartz Substances 0.000 description 16
XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
UXVMQQNJUSDDNG-UHFFFAOYSA-L Calcium chloride Chemical compound [Cl-].[Cl-].[Ca+2] UXVMQQNJUSDDNG-UHFFFAOYSA-L 0.000 description 13
239000001110 calcium chloride Substances 0.000 description 13
229910001628 calcium chloride Inorganic materials 0.000 description 13
239000000499 gel Substances 0.000 description 13
150000003839 salts Chemical class 0.000 description 13
230000008859 change Effects 0.000 description 11
238000001035 drying Methods 0.000 description 11
238000000605 extraction Methods 0.000 description 11
238000007689 inspection Methods 0.000 description 11
238000005259 measurement Methods 0.000 description 11
239000000178 monomer Substances 0.000 description 11
238000006116 polymerization reaction Methods 0.000 description 11
238000004566 IR spectroscopy Methods 0.000 description 10
WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 10
239000007795 chemical reaction product Substances 0.000 description 10
239000007810 chemical reaction solvent Substances 0.000 description 10
238000001125 extrusion Methods 0.000 description 10
238000005305 interferometry Methods 0.000 description 10
238000001556 precipitation Methods 0.000 description 10
208000037062 Polyps Diseases 0.000 description 9
230000015556 catabolic process Effects 0.000 description 9
238000006731 degradation reaction Methods 0.000 description 9
238000001704 evaporation Methods 0.000 description 9
238000011010 flushing procedure Methods 0.000 description 9
VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 9
230000010494 opalescence Effects 0.000 description 9
230000007704 transition Effects 0.000 description 9
AVQQQNCBBIEMEU-UHFFFAOYSA-N 1,1,3,3-tetramethylurea Chemical compound CN(C)C(=O)N(C)C AVQQQNCBBIEMEU-UHFFFAOYSA-N 0.000 description 8
VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 8
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 8
PJANXHGTPQOBST-VAWYXSNFSA-N Stilbene Natural products C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 8
150000001875 compounds Chemical class 0.000 description 8
238000000921 elemental analysis Methods 0.000 description 8
230000008020 evaporation Effects 0.000 description 8
239000005457 ice water Substances 0.000 description 8
150000002500 ions Chemical class 0.000 description 8
239000011159 matrix material Substances 0.000 description 8
235000021286 stilbenes Nutrition 0.000 description 8
238000004364 calculation method Methods 0.000 description 7
238000002197 infrared dichroism spectroscopy Methods 0.000 description 7
ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 description 7
CPBGOWIFSRZWIZ-UHFFFAOYSA-N 4-(4-amino-2-bromophenyl)-3-bromoaniline Chemical compound BrC1=CC(N)=CC=C1C1=CC=C(N)C=C1Br CPBGOWIFSRZWIZ-UHFFFAOYSA-N 0.000 description 6
UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 6
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 6
OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 6
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 6
229920000180 alkyd Polymers 0.000 description 6
230000015572 biosynthetic process Effects 0.000 description 6
239000004305 biphenyl Substances 0.000 description 6
125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 description 6
238000005755 formation reaction Methods 0.000 description 6
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 6
238000002791 soaking Methods 0.000 description 6
238000012360 testing method Methods 0.000 description 6
239000013598 vector Substances 0.000 description 6
MFYSUUPKMDJYPF-UHFFFAOYSA-N 2-[(4-methyl-2-nitrophenyl)diazenyl]-3-oxo-n-phenylbutanamide Chemical compound C=1C=CC=CC=1NC(=O)C(C(=O)C)N=NC1=CC=C(C)C=C1[N+]([O-])=O MFYSUUPKMDJYPF-UHFFFAOYSA-N 0.000 description 5
241001315286 Damon Species 0.000 description 5
235000018936 Vitellaria paradoxa Nutrition 0.000 description 5
238000010521 absorption reaction Methods 0.000 description 5
239000002253 acid Substances 0.000 description 5
238000005345 coagulation Methods 0.000 description 5
230000015271 coagulation Effects 0.000 description 5
235000004879 dioscorea Nutrition 0.000 description 5
229910052740 iodine Inorganic materials 0.000 description 5
238000002844 melting Methods 0.000 description 5
239000003960 organic solvent Substances 0.000 description 5
230000010287 polarization Effects 0.000 description 5
239000002244 precipitate Substances 0.000 description 5
HEMHJVSKTPXQMS-UHFFFAOYSA-M sodium hydroxide Inorganic materials [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 5
VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 4
GLUUGHFHXGJENI-UHFFFAOYSA-N Piperazine Chemical compound C1CNCCN1 GLUUGHFHXGJENI-UHFFFAOYSA-N 0.000 description 4
XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 4
230000005540 biological transmission Effects 0.000 description 4
235000010290 biphenyl Nutrition 0.000 description 4
239000004202 carbamide Substances 0.000 description 4
238000004049 embossing Methods 0.000 description 4
230000008018 melting Effects 0.000 description 4
MHSKRLJMQQNJNC-UHFFFAOYSA-N terephthalamide Chemical compound NC(=O)C1=CC=C(C(N)=O)C=C1 MHSKRLJMQQNJNC-UHFFFAOYSA-N 0.000 description 4
YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 4
125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 description 3
LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 3
WHXSMMKQMYFTQS-UHFFFAOYSA-N Lithium Chemical compound [Li] WHXSMMKQMYFTQS-UHFFFAOYSA-N 0.000 description 3
WMFOQBRAJBCJND-UHFFFAOYSA-M Lithium hydroxide Chemical compound [Li+].[OH-] WMFOQBRAJBCJND-UHFFFAOYSA-M 0.000 description 3
XGEGHDBEHXKFPX-UHFFFAOYSA-N N-methylthiourea Natural products CNC(N)=O XGEGHDBEHXKFPX-UHFFFAOYSA-N 0.000 description 3
206010042928 Syringomyelia Diseases 0.000 description 3
238000000862 absorption spectrum Methods 0.000 description 3
238000000149 argon plasma sintering Methods 0.000 description 3
238000009835 boiling Methods 0.000 description 3
125000004432 carbon atom Chemical group C* 0.000 description 3
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 3
238000000113 differential scanning calorimetry Methods 0.000 description 3
150000004820 halides Chemical class 0.000 description 3
238000010438 heat treatment Methods 0.000 description 3
229910052744 lithium Inorganic materials 0.000 description 3
XGZVUEUWXADBQD-UHFFFAOYSA-L lithium carbonate Chemical compound [Li+].[Li+].[O-]C([O-])=O XGZVUEUWXADBQD-UHFFFAOYSA-L 0.000 description 3
229910052808 lithium carbonate Inorganic materials 0.000 description 3
238000004519 manufacturing process Methods 0.000 description 3
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 3
XGEGHDBEHXKFPX-NJFSPNSNSA-N methylurea Chemical compound [14CH3]NC(N)=O XGEGHDBEHXKFPX-NJFSPNSNSA-N 0.000 description 3
125000000843 phenylene group Chemical group C1(=C(C=CC=C1)*)* 0.000 description 3
239000004014 plasticizer Substances 0.000 description 3
NLKNQRATVPKPDG-UHFFFAOYSA-M potassium iodide Chemical compound [K+].[I-] NLKNQRATVPKPDG-UHFFFAOYSA-M 0.000 description 3
125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
229910002027 silica gel Inorganic materials 0.000 description 3
239000000741 silica gel Substances 0.000 description 3
238000002411 thermogravimetry Methods 0.000 description 3
NRLUQVLHGAVXQB-UHFFFAOYSA-N 4-(4-amino-2-chloro-5-methoxyphenyl)-5-chloro-2-methoxyaniline Chemical compound C1=C(N)C(OC)=CC(C=2C(=CC(N)=C(OC)C=2)Cl)=C1Cl NRLUQVLHGAVXQB-UHFFFAOYSA-N 0.000 description 2
ZCYVEMRRCGMTRW-UHFFFAOYSA-N 7553-56-2 Chemical compound [I] ZCYVEMRRCGMTRW-UHFFFAOYSA-N 0.000 description 2
DLFVBJFMPXGRIB-UHFFFAOYSA-N Acetamide Chemical compound CC(N)=O DLFVBJFMPXGRIB-UHFFFAOYSA-N 0.000 description 2
229910014033 C-OH Inorganic materials 0.000 description 2
229910021532 Calcite Inorganic materials 0.000 description 2
HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
241000985630 Lota lota Species 0.000 description 2
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SKZKKFZAGNVIMN-UHFFFAOYSA-N Salicilamide Chemical compound NC(=O)C1=CC=CC=C1O SKZKKFZAGNVIMN-UHFFFAOYSA-N 0.000 description 2
244000007853 Sarothamnus scoparius Species 0.000 description 2
241000201776 Steno Species 0.000 description 2
QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 description 2
FZWLAAWBMGSTSO-UHFFFAOYSA-N Thiazole Chemical compound C1=CSC=N1 FZWLAAWBMGSTSO-UHFFFAOYSA-N 0.000 description 2
241000283907 Tragelaphus oryx Species 0.000 description 2
238000002441 X-ray diffraction Methods 0.000 description 2
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150000003797 alkaloid derivatives Chemical class 0.000 description 2
150000001408 amides Chemical class 0.000 description 2
125000003277 amino group Chemical group 0.000 description 2
210000003423 ankle Anatomy 0.000 description 2
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239000003795 chemical substances by application Substances 0.000 description 2
238000004587 chromatography analysis Methods 0.000 description 2
238000001816 cooling Methods 0.000 description 2
150000001879 copper Chemical class 0.000 description 2
150000002148 esters Chemical class 0.000 description 2
125000005677 ethinylene group Chemical group [*:2]C#C[*:1] 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
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LPXPTNMVRIOKMN-UHFFFAOYSA-M sodium nitrite Chemical compound [Na+].[O-]N=O LPXPTNMVRIOKMN-UHFFFAOYSA-M 0.000 description 2
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238000001429 visible spectrum Methods 0.000 description 2
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BTAGRXWGMYTPBY-UHFFFAOYSA-N 1,2,3-trichloro-4-(2,3,4-trichlorophenyl)benzene Chemical compound ClC1=C(Cl)C(Cl)=CC=C1C1=CC=C(Cl)C(Cl)=C1Cl BTAGRXWGMYTPBY-UHFFFAOYSA-N 0.000 description 1
CYSGHNMQYZDMIA-UHFFFAOYSA-N 1,3-Dimethyl-2-imidazolidinon Chemical compound CN1CCN(C)C1=O CYSGHNMQYZDMIA-UHFFFAOYSA-N 0.000 description 1
DKBPNVPNTIUXTF-UHFFFAOYSA-N 1-[4-iodo-2-(trifluoromethyl)phenyl]-4-nitro-2-(trifluoromethyl)benzene Chemical group FC(F)(F)C1=CC([N+](=O)[O-])=CC=C1C1=CC=C(I)C=C1C(F)(F)F DKBPNVPNTIUXTF-UHFFFAOYSA-N 0.000 description 1
SXEQQBBOAMHOID-UHFFFAOYSA-N 1-bromo-4-nitro-2-(trifluoromethyl)benzene Chemical compound [O-][N+](=O)C1=CC=C(Br)C(C(F)(F)F)=C1 SXEQQBBOAMHOID-UHFFFAOYSA-N 0.000 description 1
GGYVTHJIUNGKFZ-UHFFFAOYSA-N 1-methylpiperidin-2-one Chemical compound CN1CCCCC1=O GGYVTHJIUNGKFZ-UHFFFAOYSA-N 0.000 description 1
NSMWYRLQHIXVAP-UHFFFAOYSA-N 2,5-dimethylpiperazine Chemical compound CC1CNC(C)CN1 NSMWYRLQHIXVAP-UHFFFAOYSA-N 0.000 description 1
NGNBDVOYPDDBFK-UHFFFAOYSA-N 2-[2,4-di(pentan-2-yl)phenoxy]acetyl chloride Chemical compound CCCC(C)C1=CC=C(OCC(Cl)=O)C(C(C)CCC)=C1 NGNBDVOYPDDBFK-UHFFFAOYSA-N 0.000 description 1
ZBMRKNMTMPPMMK-UHFFFAOYSA-N 2-amino-4-[hydroxy(methyl)phosphoryl]butanoic acid;azane Chemical compound [NH4+].CP(O)(=O)CCC(N)C([O-])=O ZBMRKNMTMPPMMK-UHFFFAOYSA-N 0.000 description 1
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QDBOAKPEXMMQFO-UHFFFAOYSA-N 4-(4-carbonochloridoylphenyl)benzoyl chloride Chemical compound C1=CC(C(=O)Cl)=CC=C1C1=CC=C(C(Cl)=O)C=C1 QDBOAKPEXMMQFO-UHFFFAOYSA-N 0.000 description 1
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150000001412 amines Chemical class 0.000 description 1
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229910001919 chlorite Inorganic materials 0.000 description 1
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QBWCMBCROVPCKQ-UHFFFAOYSA-N chlorous acid Chemical compound OCl=O QBWCMBCROVPCKQ-UHFFFAOYSA-N 0.000 description 1
238000000576 coating method Methods 0.000 description 1
238000010622 cold drawing Methods 0.000 description 1
230000002301 combined effect Effects 0.000 description 1
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230000036461 convulsion Effects 0.000 description 1
239000002178 crystalline material Substances 0.000 description 1
RHKZVMUBMXGOLL-UHFFFAOYSA-N cyclopentolate hydrochloride Chemical compound Cl.C1CCCC1(O)C(C(=O)OCCN(C)C)C1=CC=CC=C1 RHKZVMUBMXGOLL-UHFFFAOYSA-N 0.000 description 1
230000009089 cytolysis Effects 0.000 description 1
230000003247 decreasing effect Effects 0.000 description 1
230000001627 detrimental effect Effects 0.000 description 1
238000010586 diagram Methods 0.000 description 1
239000012954 diazonium Substances 0.000 description 1
150000001989 diazonium salts Chemical class 0.000 description 1
125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
230000003292 diminished effect Effects 0.000 description 1
230000008034 disappearance Effects 0.000 description 1
SDIXRDNYIMOKSG-UHFFFAOYSA-L disodium methyl arsenate Chemical compound [Na+].[Na+].C[As]([O-])([O-])=O SDIXRDNYIMOKSG-UHFFFAOYSA-L 0.000 description 1
238000004090 dissolution Methods 0.000 description 1
125000005678 ethenylene group Chemical group [H]C([*:1])=C([H])[*:2] 0.000 description 1
239000002657 fibrous material Substances 0.000 description 1
238000010528 free radical solution polymerization reaction Methods 0.000 description 1
210000004907 gland Anatomy 0.000 description 1
239000003292 glue Substances 0.000 description 1
238000000227 grinding Methods 0.000 description 1
GNOIPBMMFNIUFM-UHFFFAOYSA-N hexamethylphosphoric triamide Chemical compound CN(C)P(=O)(N(C)C)N(C)C GNOIPBMMFNIUFM-UHFFFAOYSA-N 0.000 description 1
239000003864 humus Substances 0.000 description 1
125000004356 hydroxy functional group Chemical group O* 0.000 description 1
125000004029 hydroxymethyl group Chemical group [H]OC([H])([H])* 0.000 description 1
238000005286 illumination Methods 0.000 description 1
238000005304 joining Methods 0.000 description 1
238000010030 laminating Methods 0.000 description 1
230000000670 limiting effect Effects 0.000 description 1
KAGBQTDQNWOCND-UHFFFAOYSA-M lithium;chlorite Chemical compound [Li+].[O-]Cl=O KAGBQTDQNWOCND-UHFFFAOYSA-M 0.000 description 1
238000012423 maintenance Methods 0.000 description 1
206010025482 malaise Diseases 0.000 description 1
230000007246 mechanism Effects 0.000 description 1
239000012528 membrane Substances 0.000 description 1
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125000000956 methoxy group Chemical group [H]C([H])([H])O* 0.000 description 1
238000000386 microscopy Methods 0.000 description 1
210000004080 milk Anatomy 0.000 description 1
235000013336 milk Nutrition 0.000 description 1
238000002156 mixing Methods 0.000 description 1
125000004433 nitrogen atom Chemical group N* 0.000 description 1
239000003921 oil Substances 0.000 description 1
239000012044 organic layer Substances 0.000 description 1
125000002971 oxazolyl group Chemical group 0.000 description 1
SOQBVABWOPYFQZ-UHFFFAOYSA-N oxygen(2-);titanium(4+) Chemical class [O-2].[O-2].[Ti+4] SOQBVABWOPYFQZ-UHFFFAOYSA-N 0.000 description 1
239000002245 particle Substances 0.000 description 1
239000004033 plastic Substances 0.000 description 1
238000005498 polishing Methods 0.000 description 1
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239000000843 powder Substances 0.000 description 1
238000004321 preservation Methods 0.000 description 1
238000003825 pressing Methods 0.000 description 1
230000008569 process Effects 0.000 description 1
230000001737 promoting effect Effects 0.000 description 1
238000000746 purification Methods 0.000 description 1
239000000376 reactant Substances 0.000 description 1
238000011084 recovery Methods 0.000 description 1
230000002829 reductive effect Effects 0.000 description 1
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238000007493 shaping process Methods 0.000 description 1
238000007086 side reaction Methods 0.000 description 1
230000011664 signaling Effects 0.000 description 1
LIVNPJMFVYWSIS-UHFFFAOYSA-N silicon monoxide Chemical class [Si-]#[O+] LIVNPJMFVYWSIS-UHFFFAOYSA-N 0.000 description 1
229910052814 silicon oxide Inorganic materials 0.000 description 1
238000004088 simulation Methods 0.000 description 1
239000010454 slate Substances 0.000 description 1
229910052708 sodium Inorganic materials 0.000 description 1
239000011734 sodium Substances 0.000 description 1
235000010267 sodium hydrogen sulphite Nutrition 0.000 description 1
HYHCSLBZRBJJCH-UHFFFAOYSA-M sodium hydrosulfide Chemical compound [Na+].[SH-] HYHCSLBZRBJJCH-UHFFFAOYSA-M 0.000 description 1
235000010288 sodium nitrite Nutrition 0.000 description 1
239000011343 solid material Substances 0.000 description 1
230000007928 solubilization Effects 0.000 description 1
238000005063 solubilization Methods 0.000 description 1
239000000758 substrate Substances 0.000 description 1
229940124530 sulfonamide Drugs 0.000 description 1
150000003456 sulfonamides Chemical class 0.000 description 1
BDHFUVZGWQCTTF-UHFFFAOYSA-M sulfonate Chemical compound [O-]S(=O)=O BDHFUVZGWQCTTF-UHFFFAOYSA-M 0.000 description 1
150000003459 sulfonic acid esters Chemical class 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
125000004001 thioalkyl group Chemical group 0.000 description 1
125000004055 thiomethyl group Chemical group [H]SC([H])([H])* 0.000 description 1
229940034208 thyroxine Drugs 0.000 description 1
XUIIKFGFIJCVMT-UHFFFAOYSA-N thyroxine-binding globulin Natural products IC1=CC(CC([NH3+])C([O-])=O)=CC(I)=C1OC1=CC(I)=C(O)C(I)=C1 XUIIKFGFIJCVMT-UHFFFAOYSA-N 0.000 description 1
GWEVSGVZZGPLCZ-UHFFFAOYSA-N titanium dioxide Inorganic materials O=[Ti]=O GWEVSGVZZGPLCZ-UHFFFAOYSA-N 0.000 description 1
235000010215 titanium dioxide Nutrition 0.000 description 1
230000009466 transformation Effects 0.000 description 1
238000002211 ultraviolet spectrum Methods 0.000 description 1
238000002371 ultraviolet--visible spectrum Methods 0.000 description 1
238000001771 vacuum deposition Methods 0.000 description 1

Landscapes

Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)

CA000397302A 1981-03-02 1982-03-01 Dispositif optique au polymere birefringent Expired CA1216111A (fr)

Applications Claiming Priority (4)

Application Number	Priority Date	Filing Date	Title
US238,054		1981-03-02
US06/238,054 US4446305A (en)	1981-03-02	1981-03-02	Optical device including birefringent polymer
US06/239,180 US4393194A (en)	1981-03-02	1981-03-02	Substituted-quaterphenylene polyamide
US239,180		1981-03-02

Publications (1)

Publication Number	Publication Date
CA1216111A true CA1216111A (fr)	1987-01-06

Family

ID=26931303

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
CA000397302A Expired CA1216111A (fr)	1981-03-02	1982-03-01	Dispositif optique au polymere birefringent

Country Status (1)

Country	Link
CA (1)	CA1216111A (fr)

1982
- 1982-03-01 CA CA000397302A patent/CA1216111A/fr not_active Expired

Legal Events

Date	Code	Title	Description
2004-01-06	MKEX	Expiry

Publication	Publication Date	Title
US4446305A (en)	1984-05-01	Optical device including birefringent polymer
US4521588A (en)	1985-06-04	Optical device including birefringent polyhydrazide polymer
US4520189A (en)	1985-05-28	Optical device including birefringent aromatic amino carboxylic acid polymer
US4525413A (en)	1985-06-25	Optical device including birefringent polymer
US4384107A (en)	1983-05-17	Polyamide comprising substituted biphenylene or substituted stilbene radicals
US4461886A (en)	1984-07-24	Substituted birefringent polyamide
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JP2002006138A (ja)	2002-01-09	光学補償シートおよびその製造方法
EP0061026B1 (fr)	1985-01-30	Polyamides contenant des motifs quaterphénilènes substitués
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JP2002156528A (ja)	2002-05-31	熱可塑性高分子フィルム
CA1216111A (fr)	1987-01-06	Dispositif optique au polymere birefringent
US4503248A (en)	1985-03-05	Substituted-quaterphenylene monomers for the production of polyamides therefrom
WO2023101014A1 (fr)	2023-06-08	Combinateur de faisceau, procédé de formation d'un film d'alignement, et procédé de production d'élément optique
US9829617B2 (en)	2017-11-28	Polymer-small molecule film or coating having reverse or flat dispersion of retardation
US4461888A (en)	1984-07-24	Substituted birefringent polyhydrazide
US4461887A (en)	1984-07-24	Birefringent polymer containing recurring units from dienoic acid
JP2004309617A (ja)	2004-11-04	ロール状位相差フィルム
JP2008026730A (ja)	2008-02-07	光学補償フィルム、及びその製造方法、並びに偏光板
US4393196A (en)	1983-07-12	Polymers containing recurring units from dienoic acid