IL101993A - Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized - Google Patents

Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized

Info

Publication number: IL101993A
Authority: IL; Israel
Prior art keywords: liquid crystal; monomer; photoinitiator; diacrylate; adduct
Prior art date: 1991-10-23

Application number

IL10199392A

Other languages

English (en)

Hebrew (he)

Original Assignee

Hughes Aircraft Co

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.)

1991-10-23

Filing date

1992-05-25

Publication date

1995-06-29

1992-05-25 Application filed by Hughes Aircraft Co filed Critical Hughes Aircraft Co

1995-06-29 Publication of IL101993A publication Critical patent/IL101993A/en

Links

239000004983 Polymer Dispersed Liquid Crystal Substances 0.000 title claims description 97
238000000034 method Methods 0.000 title claims description 33
239000004973 liquid crystal related substance Substances 0.000 claims description 135
239000000178 monomer Substances 0.000 claims description 64
239000000203 mixture Substances 0.000 claims description 61
239000000463 material Substances 0.000 claims description 36
239000000243 solution Substances 0.000 claims description 32
XXROGKLTLUQVRX-UHFFFAOYSA-N allyl alcohol Chemical compound OCC=C XXROGKLTLUQVRX-UHFFFAOYSA-N 0.000 claims description 28
MYWOJODOMFBVCB-UHFFFAOYSA-N 1,2,6-trimethylphenanthrene Chemical compound CC1=CC=C2C3=CC(C)=CC=C3C=CC2=C1C MYWOJODOMFBVCB-UHFFFAOYSA-N 0.000 claims description 20
JQRRFDWXQOQICD-UHFFFAOYSA-N biphenylen-1-ylboronic acid Chemical compound C12=CC=CC=C2C2=C1C=CC=C2B(O)O JQRRFDWXQOQICD-UHFFFAOYSA-N 0.000 claims description 17
LSDPWZHWYPCBBB-UHFFFAOYSA-N Methanethiol Chemical compound SC LSDPWZHWYPCBBB-UHFFFAOYSA-N 0.000 claims description 15
125000004386 diacrylate group Chemical group 0.000 claims description 15
NIMLQBUJDJZYEJ-UHFFFAOYSA-N isophorone diisocyanate Chemical compound CC1(C)CC(N=C=O)CC(C)(CN=C=O)C1 NIMLQBUJDJZYEJ-UHFFFAOYSA-N 0.000 claims description 14
239000005058 Isophorone diisocyanate Substances 0.000 claims description 13
VLCCKNLIFIJYOQ-UHFFFAOYSA-N [3-hydroxy-2,2-bis(hydroxymethyl)propyl] 2,2,3,3-tetrakis(sulfanyl)propanoate Chemical compound OCC(CO)(CO)COC(=O)C(S)(S)C(S)S VLCCKNLIFIJYOQ-UHFFFAOYSA-N 0.000 claims description 12
DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 claims description 11
JMMVHMOAIMOMOF-UHFFFAOYSA-N (4-prop-2-enoyloxyphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=C(OC(=O)C=C)C=C1 JMMVHMOAIMOMOF-UHFFFAOYSA-N 0.000 claims description 9
238000006116 polymerization reaction Methods 0.000 claims description 9
-1 acryloxy-2-hydroxypropyl Chemical group 0.000 claims description 8
125000000217 alkyl group Chemical group 0.000 claims description 7
ZDQNWDNMNKSMHI-UHFFFAOYSA-N 1-[2-(2-prop-2-enoyloxypropoxy)propoxy]propan-2-yl prop-2-enoate Chemical compound C=CC(=O)OC(C)COC(C)COCC(C)OC(=O)C=C ZDQNWDNMNKSMHI-UHFFFAOYSA-N 0.000 claims description 6
RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 claims description 6
WLPATYNQCGVFFH-UHFFFAOYSA-N 2-phenylbenzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1 WLPATYNQCGVFFH-UHFFFAOYSA-N 0.000 claims description 5
ATVJXMYDOSMEPO-UHFFFAOYSA-N 3-prop-2-enoxyprop-1-ene Chemical compound C=CCOCC=C ATVJXMYDOSMEPO-UHFFFAOYSA-N 0.000 claims description 5
239000002019 doping agent Substances 0.000 claims description 5
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 claims description 5
229920001223 polyethylene glycol Polymers 0.000 claims description 5
LEJBBGNFPAFPKQ-UHFFFAOYSA-N 2-(2-prop-2-enoyloxyethoxy)ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOC(=O)C=C LEJBBGNFPAFPKQ-UHFFFAOYSA-N 0.000 claims description 4
PSYGHMBJXWRQFD-UHFFFAOYSA-N 2-(2-sulfanylacetyl)oxyethyl 2-sulfanylacetate Chemical compound SCC(=O)OCCOC(=O)CS PSYGHMBJXWRQFD-UHFFFAOYSA-N 0.000 claims description 4
HCLJOFJIQIJXHS-UHFFFAOYSA-N 2-[2-[2-(2-prop-2-enoyloxyethoxy)ethoxy]ethoxy]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCOCCOCCOCCOC(=O)C=C HCLJOFJIQIJXHS-UHFFFAOYSA-N 0.000 claims description 4
JJSYPAGPNHFLML-UHFFFAOYSA-N 2-ethyl-2-(hydroxymethyl)propane-1,3-diol;3-sulfanylpropanoic acid Chemical compound OC(=O)CCS.OC(=O)CCS.OC(=O)CCS.CCC(CO)(CO)CO JJSYPAGPNHFLML-UHFFFAOYSA-N 0.000 claims description 4
DKIDEFUBRARXTE-UHFFFAOYSA-M 3-mercaptopropionate Chemical compound [O-]C(=O)CCS DKIDEFUBRARXTE-UHFFFAOYSA-M 0.000 claims description 4
LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 4
239000002202 Polyethylene glycol Substances 0.000 claims description 4
FHLPGTXWCFQMIU-UHFFFAOYSA-N [4-[2-(4-prop-2-enoyloxyphenyl)propan-2-yl]phenyl] prop-2-enoate Chemical compound C=1C=C(OC(=O)C=C)C=CC=1C(C)(C)C1=CC=C(OC(=O)C=C)C=C1 FHLPGTXWCFQMIU-UHFFFAOYSA-N 0.000 claims description 4
ZUOUZKKEUPVFJK-UHFFFAOYSA-N diphenyl Chemical compound C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 claims description 4
NDJCDNQKIINPMP-UHFFFAOYSA-N 2,4-dihydroxy-2,4-dimethyl-1,5-diphenylpentan-3-one Chemical compound C=1C=CC=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=CC=C1 NDJCDNQKIINPMP-UHFFFAOYSA-N 0.000 claims description 3
125000003545 alkoxy group Chemical group 0.000 claims description 3
229910052739 hydrogen Inorganic materials 0.000 claims description 3
WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 claims description 3
238000005191 phase separation Methods 0.000 claims description 3
ZEMYZPXPNMSHCE-UHFFFAOYSA-N (3-methyl-1-prop-2-enoyloxypentyl) prop-2-enoate Chemical compound CCC(C)CC(OC(=O)C=C)OC(=O)C=C ZEMYZPXPNMSHCE-UHFFFAOYSA-N 0.000 claims description 2
YJTKZCDBKVTVBY-UHFFFAOYSA-N 1,3-Diphenylbenzene Chemical group C1=CC=CC=C1C1=CC=CC(C=2C=CC=CC=2)=C1 YJTKZCDBKVTVBY-UHFFFAOYSA-N 0.000 claims description 2
HMQFJYLWNWIYKQ-UHFFFAOYSA-N 1,4-diphenylbutadiyne Chemical group C1=CC=CC=C1C#CC#CC1=CC=CC=C1 HMQFJYLWNWIYKQ-UHFFFAOYSA-N 0.000 claims description 2
IBLKWZIFZMJLFL-UHFFFAOYSA-N 1-phenoxypropan-2-ol Chemical compound CC(O)COC1=CC=CC=C1 IBLKWZIFZMJLFL-UHFFFAOYSA-N 0.000 claims description 2
KAJBSGLXSREIHP-UHFFFAOYSA-N 2,2-bis[(2-sulfanylacetyl)oxymethyl]butyl 2-sulfanylacetate Chemical compound SCC(=O)OCC(CC)(COC(=O)CS)COC(=O)CS KAJBSGLXSREIHP-UHFFFAOYSA-N 0.000 claims description 2
YIJYFLXQHDOQGW-UHFFFAOYSA-N 2-[2,4,6-trioxo-3,5-bis(2-prop-2-enoyloxyethyl)-1,3,5-triazinan-1-yl]ethyl prop-2-enoate Chemical compound C=CC(=O)OCCN1C(=O)N(CCOC(=O)C=C)C(=O)N(CCOC(=O)C=C)C1=O YIJYFLXQHDOQGW-UHFFFAOYSA-N 0.000 claims description 2
XNLHQURWXIWCDF-UHFFFAOYSA-N 2-[4-[2,4-dihydroxy-2,4-dimethyl-3-oxo-5-[4-(2-prop-2-enoyloxyethoxy)phenyl]pentyl]phenoxy]ethyl prop-2-enoate Chemical compound C=1C=C(OCCOC(=O)C=C)C=CC=1CC(C)(O)C(=O)C(O)(C)CC1=CC=C(OCCOC(=O)C=C)C=C1 XNLHQURWXIWCDF-UHFFFAOYSA-N 0.000 claims description 2
XMLYCEVDHLAQEL-UHFFFAOYSA-N 2-hydroxy-2-methyl-1-phenylpropan-1-one Chemical class CC(C)(O)C(=O)C1=CC=CC=C1 XMLYCEVDHLAQEL-UHFFFAOYSA-N 0.000 claims description 2
KUDUQBURMYMBIJ-UHFFFAOYSA-N 2-prop-2-enoyloxyethyl prop-2-enoate Chemical compound C=CC(=O)OCCOC(=O)C=C KUDUQBURMYMBIJ-UHFFFAOYSA-N 0.000 claims description 2
DMQYPVOQAARSNF-UHFFFAOYSA-N 3-[2,3-bis(3-prop-2-enoyloxypropoxy)propoxy]propyl prop-2-enoate Chemical compound C=CC(=O)OCCCOCC(OCCCOC(=O)C=C)COCCCOC(=O)C=C DMQYPVOQAARSNF-UHFFFAOYSA-N 0.000 claims description 2
FIHBHSQYSYVZQE-UHFFFAOYSA-N 6-prop-2-enoyloxyhexyl prop-2-enoate Chemical compound C=CC(=O)OCCCCCCOC(=O)C=C FIHBHSQYSYVZQE-UHFFFAOYSA-N 0.000 claims description 2
CMKGUZUFURPPJS-UHFFFAOYSA-N C=CC(=O)OC(C(O)C)OC(=O)C1=CC=CC=C1C(=O)OC(OC(=O)C=C)C(C)O Chemical group C=CC(=O)OC(C(O)C)OC(=O)C1=CC=CC=C1C(=O)OC(OC(=O)C=C)C(C)O CMKGUZUFURPPJS-UHFFFAOYSA-N 0.000 claims description 2
JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 claims description 2
CZPWVGJYEJSRLH-UHFFFAOYSA-N Pyrimidine Chemical compound C1=CN=CN=C1 CZPWVGJYEJSRLH-UHFFFAOYSA-N 0.000 claims description 2
DAKWPKUUDNSNPN-UHFFFAOYSA-N Trimethylolpropane triacrylate Chemical compound C=CC(=O)OCC(CC)(COC(=O)C=C)COC(=O)C=C DAKWPKUUDNSNPN-UHFFFAOYSA-N 0.000 claims description 2
239000007983 Tris buffer Substances 0.000 claims description 2
INXWLSDYDXPENO-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-[[3-prop-2-enoyloxy-2,2-bis(prop-2-enoyloxymethyl)propoxy]methyl]propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(COC(=O)C=C)(CO)COCC(COC(=O)C=C)(COC(=O)C=C)COC(=O)C=C INXWLSDYDXPENO-UHFFFAOYSA-N 0.000 claims description 2
RUDUCNPHDIMQCY-UHFFFAOYSA-N [3-(2-sulfanylacetyl)oxy-2,2-bis[(2-sulfanylacetyl)oxymethyl]propyl] 2-sulfanylacetate Chemical compound SCC(=O)OCC(COC(=O)CS)(COC(=O)CS)COC(=O)CS RUDUCNPHDIMQCY-UHFFFAOYSA-N 0.000 claims description 2
YAAUVJUJVBJRSQ-UHFFFAOYSA-N [3-(3-sulfanylpropanoyloxy)-2-[[3-(3-sulfanylpropanoyloxy)-2,2-bis(3-sulfanylpropanoyloxymethyl)propoxy]methyl]-2-(3-sulfanylpropanoyloxymethyl)propyl] 3-sulfanylpropanoate Chemical compound SCCC(=O)OCC(COC(=O)CCS)(COC(=O)CCS)COCC(COC(=O)CCS)(COC(=O)CCS)COC(=O)CCS YAAUVJUJVBJRSQ-UHFFFAOYSA-N 0.000 claims description 2
235000010290 biphenyl Nutrition 0.000 claims description 2
239000004305 biphenyl Substances 0.000 claims description 2
JRXXLCKWQFKACW-UHFFFAOYSA-N biphenylacetylene Chemical compound C1=CC=CC=C1C#CC1=CC=CC=C1 JRXXLCKWQFKACW-UHFFFAOYSA-N 0.000 claims description 2
125000001589 carboacyl group Chemical group 0.000 claims description 2
125000001309 chloro group Chemical group Cl* 0.000 claims description 2
125000004093 cyano group Chemical group *C#N 0.000 claims description 2
IGARGHRYKHJQSM-UHFFFAOYSA-N cyclohexylbenzene Chemical compound C1CCCCC1C1=CC=CC=C1 IGARGHRYKHJQSM-UHFFFAOYSA-N 0.000 claims description 2
ZAXCOQRALRPOSO-UHFFFAOYSA-N ethyl prop-2-eneperoxoate propane-1,2,3-triol Chemical compound C(C=C)(=O)OOCC.C(C=C)(=O)OOCC.C(C=C)(=O)OOCC.OCC(O)CO ZAXCOQRALRPOSO-UHFFFAOYSA-N 0.000 claims description 2
125000001153 fluoro group Chemical group F* 0.000 claims description 2
229910052736 halogen Inorganic materials 0.000 claims description 2
150000002367 halogens Chemical class 0.000 claims description 2
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 2
YDKNBNOOCSNPNS-UHFFFAOYSA-N methyl 1,3-benzoxazole-2-carboxylate Chemical compound C1=CC=C2OC(C(=O)OC)=NC2=C1 YDKNBNOOCSNPNS-UHFFFAOYSA-N 0.000 claims description 2
229910052757 nitrogen Inorganic materials 0.000 claims description 2
FCJSHPDYVMKCHI-UHFFFAOYSA-N phenyl benzoate Chemical class C=1C=CC=CC=1C(=O)OC1=CC=CC=C1 FCJSHPDYVMKCHI-UHFFFAOYSA-N 0.000 claims description 2
229910052717 sulfur Inorganic materials 0.000 claims description 2
NIXOWILDQLNWCW-UHFFFAOYSA-N acrylic acid group Chemical group C(C=C)(=O)O NIXOWILDQLNWCW-UHFFFAOYSA-N 0.000 claims 3
SCBKKGZZWVHHOC-UHFFFAOYSA-N 2,2-bis(sulfanyl)propanoic acid Chemical compound CC(S)(S)C(O)=O SCBKKGZZWVHHOC-UHFFFAOYSA-N 0.000 claims 1
CNDCQWGRLNGNNO-UHFFFAOYSA-N 2-(2-sulfanylethoxy)ethanethiol Chemical compound SCCOCCS CNDCQWGRLNGNNO-UHFFFAOYSA-N 0.000 claims 1
FQMIAEWUVYWVNB-UHFFFAOYSA-N 3-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OC(C)CCOC(=O)C=C FQMIAEWUVYWVNB-UHFFFAOYSA-N 0.000 claims 1
GFLJTEHFZZNCTR-UHFFFAOYSA-N 3-prop-2-enoyloxypropyl prop-2-enoate Chemical compound C=CC(=O)OCCCOC(=O)C=C GFLJTEHFZZNCTR-UHFFFAOYSA-N 0.000 claims 1
JHWGFJBTMHEZME-UHFFFAOYSA-N 4-prop-2-enoyloxybutyl prop-2-enoate Chemical compound C=CC(=O)OCCCCOC(=O)C=C JHWGFJBTMHEZME-UHFFFAOYSA-N 0.000 claims 1
HVVWZTWDBSEWIH-UHFFFAOYSA-N [2-(hydroxymethyl)-3-prop-2-enoyloxy-2-(prop-2-enoyloxymethyl)propyl] prop-2-enoate Chemical compound C=CC(=O)OCC(CO)(COC(=O)C=C)COC(=O)C=C HVVWZTWDBSEWIH-UHFFFAOYSA-N 0.000 claims 1
125000004414 alkyl thio group Chemical group 0.000 claims 1
229940068918 polyethylene glycol 400 Drugs 0.000 claims 1
239000002861 polymer material Substances 0.000 claims 1
239000010408 film Substances 0.000 description 50
210000004027 cell Anatomy 0.000 description 40
PIZHFBODNLEQBL-UHFFFAOYSA-N 2,2-diethoxy-1-phenylethanone Chemical compound CCOC(OCC)C(=O)C1=CC=CC=C1 PIZHFBODNLEQBL-UHFFFAOYSA-N 0.000 description 34
239000000499 gel Substances 0.000 description 30
239000012071 phase Substances 0.000 description 22
229920000642 polymer Polymers 0.000 description 19
239000003999 initiator Substances 0.000 description 17
230000000694 effects Effects 0.000 description 13
238000000149 argon plasma sintering Methods 0.000 description 10
RWCCWEUUXYIKHB-UHFFFAOYSA-N benzophenone Chemical compound C=1C=CC=CC=1C(=O)C1=CC=CC=C1 RWCCWEUUXYIKHB-UHFFFAOYSA-N 0.000 description 10
229940024874 benzophenone Drugs 0.000 description 10
239000012965 benzophenone Substances 0.000 description 10
238000011109 contamination Methods 0.000 description 10
239000011159 matrix material Substances 0.000 description 10
UUEYEUDSRFNIQJ-UHFFFAOYSA-N CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O Chemical compound CCOC(N)=O.CCOC(N)=O.CC(=C)C(O)=O.CC(=C)C(O)=O UUEYEUDSRFNIQJ-UHFFFAOYSA-N 0.000 description 9
230000015572 biosynthetic process Effects 0.000 description 6
239000011521 glass Substances 0.000 description 6
238000006243 chemical reaction Methods 0.000 description 5
HTSGKJQDMSTCGS-UHFFFAOYSA-N 1,4-bis(4-chlorophenyl)-2-(4-methylphenyl)sulfonylbutane-1,4-dione Chemical compound C1=CC(C)=CC=C1S(=O)(=O)C(C(=O)C=1C=CC(Cl)=CC=1)CC(=O)C1=CC=C(Cl)C=C1 HTSGKJQDMSTCGS-UHFFFAOYSA-N 0.000 description 4
230000005540 biological transmission Effects 0.000 description 4
230000000994 depressogenic effect Effects 0.000 description 4
230000005684 electric field Effects 0.000 description 4
239000007787 solid Substances 0.000 description 4
ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 3
238000013459 approach Methods 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
230000008859 change Effects 0.000 description 3
239000002131 composite material Substances 0.000 description 3
150000001875 compounds Chemical class 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000006731 degradation reaction Methods 0.000 description 3
QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 3
229910052753 mercury Inorganic materials 0.000 description 3
229940113165 trimethylolpropane Drugs 0.000 description 3
229920002799 BoPET Polymers 0.000 description 2
229910014033 C-OH Inorganic materials 0.000 description 2
229910014570 C—OH Inorganic materials 0.000 description 2
239000005041 Mylar™ Substances 0.000 description 2
239000004988 Nematic liquid crystal Substances 0.000 description 2
239000004642 Polyimide Substances 0.000 description 2
239000011203 carbon fibre reinforced carbon Substances 0.000 description 2
235000013351 cheese Nutrition 0.000 description 2
238000000576 coating method Methods 0.000 description 2
229920001577 copolymer Polymers 0.000 description 2
238000002425 crystallisation Methods 0.000 description 2
230000008025 crystallization Effects 0.000 description 2
238000009472 formulation Methods 0.000 description 2
230000001788 irregular Effects 0.000 description 2
238000002156 mixing Methods 0.000 description 2
238000012986 modification Methods 0.000 description 2
230000004048 modification Effects 0.000 description 2
230000003287 optical effect Effects 0.000 description 2
229940059574 pentaerithrityl Drugs 0.000 description 2
229920001721 polyimide Polymers 0.000 description 2
230000008569 process Effects 0.000 description 2
239000011347 resin Substances 0.000 description 2
229920005989 resin Polymers 0.000 description 2
239000007790 solid phase Substances 0.000 description 2
125000006850 spacer group Chemical group 0.000 description 2
DSTUKHPLWATFCG-UHFFFAOYSA-N (2-benzoylphenyl) prop-2-enoate Chemical compound C=CC(=O)OC1=CC=CC=C1C(=O)C1=CC=CC=C1 DSTUKHPLWATFCG-UHFFFAOYSA-N 0.000 description 1
AUXIEQKHXAYAHG-UHFFFAOYSA-N 1-phenylcyclohexane-1-carbonitrile Chemical compound C=1C=CC=CC=1C1(C#N)CCCCC1 AUXIEQKHXAYAHG-UHFFFAOYSA-N 0.000 description 1
SHFGENOBPXWUJF-UHFFFAOYSA-N 2-(2-phenylphenyl)benzonitrile Chemical group N#CC1=CC=CC=C1C1=CC=CC=C1C1=CC=CC=C1 SHFGENOBPXWUJF-UHFFFAOYSA-N 0.000 description 1
JPBFKTCKZLMJED-UHFFFAOYSA-N 4-(4-heptoxyphenyl)benzonitrile Chemical group C1=CC(OCCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 JPBFKTCKZLMJED-UHFFFAOYSA-N 0.000 description 1
ZGOWXOZNUNZPAV-UHFFFAOYSA-N 4-(4-heptylphenyl)benzonitrile Chemical group C1=CC(CCCCCCC)=CC=C1C1=CC=C(C#N)C=C1 ZGOWXOZNUNZPAV-UHFFFAOYSA-N 0.000 description 1
HASJHBAIJYYACQ-UHFFFAOYSA-N 4-(4-pentyl-4-phenylcyclohexa-1,5-dien-1-yl)benzonitrile Chemical group C1=CC(CCCCC)(C=2C=CC=CC=2)CC=C1C1=CC=C(C#N)C=C1 HASJHBAIJYYACQ-UHFFFAOYSA-N 0.000 description 1
RZCQJZFWJZHMPK-UHFFFAOYSA-N 4-(4-propoxyphenyl)benzonitrile Chemical group C1=CC(OCCC)=CC=C1C1=CC=C(C#N)C=C1 RZCQJZFWJZHMPK-UHFFFAOYSA-N 0.000 description 1
239000005214 4-Cyano-4'-heptyloxybiphenyl Substances 0.000 description 1
239000005212 4-Cyano-4'-pentylbiphenyl Substances 0.000 description 1
HHPCNRKYVYWYAU-UHFFFAOYSA-N 4-cyano-4'-pentylbiphenyl Chemical group C1=CC(CCCCC)=CC=C1C1=CC=C(C#N)C=C1 HHPCNRKYVYWYAU-UHFFFAOYSA-N 0.000 description 1
GVGDOJCINGKAJB-UHFFFAOYSA-N CC(C)(C)C.OC(=O)CS.OC(=O)CS.OC(=O)CS Chemical compound CC(C)(C)C.OC(=O)CS.OC(=O)CS.OC(=O)CS GVGDOJCINGKAJB-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
239000005977 Ethylene Substances 0.000 description 1
238000003848 UV Light-Curing Methods 0.000 description 1
150000001252 acrylic acid derivatives Chemical class 0.000 description 1
239000000654 additive Substances 0.000 description 1
230000009286 beneficial effect Effects 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
239000004020 conductor Substances 0.000 description 1
239000000356 contaminant Substances 0.000 description 1
210000002858 crystal cell Anatomy 0.000 description 1
238000001723 curing Methods 0.000 description 1
239000012799 electrically-conductive coating Substances 0.000 description 1
230000007613 environmental effect Effects 0.000 description 1
NLFBCYMMUAKCPC-KQQUZDAGSA-N ethyl (e)-3-[3-amino-2-cyano-1-[(e)-3-ethoxy-3-oxoprop-1-enyl]sulfanyl-3-oxoprop-1-enyl]sulfanylprop-2-enoate Chemical compound CCOC(=O)\C=C\SC(=C(C#N)C(N)=O)S\C=C\C(=O)OCC NLFBCYMMUAKCPC-KQQUZDAGSA-N 0.000 description 1
HNPDNOZNULJJDL-UHFFFAOYSA-N ethyl n-ethenylcarbamate Chemical class CCOC(=O)NC=C HNPDNOZNULJJDL-UHFFFAOYSA-N 0.000 description 1
239000012530 fluid Substances 0.000 description 1
AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
KCWDJXPPZHMEIK-UHFFFAOYSA-N isocyanic acid;toluene Chemical compound N=C=O.N=C=O.CC1=CC=CC=C1 KCWDJXPPZHMEIK-UHFFFAOYSA-N 0.000 description 1
230000014759 maintenance of location Effects 0.000 description 1
150000002734 metacrylic acid derivatives Chemical class 0.000 description 1
239000007777 multifunctional material Substances 0.000 description 1
239000003973 paint Substances 0.000 description 1
FZUGPQWGEGAKET-UHFFFAOYSA-N parbenate Chemical compound CCOC(=O)C1=CC=C(N(C)C)C=C1 FZUGPQWGEGAKET-UHFFFAOYSA-N 0.000 description 1
230000000704 physical effect Effects 0.000 description 1
238000000053 physical method Methods 0.000 description 1
230000010287 polarization Effects 0.000 description 1
229920006254 polymer film Polymers 0.000 description 1
230000000379 polymerizing effect Effects 0.000 description 1
238000012545 processing Methods 0.000 description 1
239000011253 protective coating Substances 0.000 description 1
238000012360 testing method Methods 0.000 description 1
239000010409 thin film Substances 0.000 description 1
230000007704 transition Effects 0.000 description 1
150000003673 urethanes Chemical class 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-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

Classifications

- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K19/00—Liquid crystal materials
- C09K19/52—Liquid crystal materials characterised by components which are not liquid crystals, e.g. additives with special physical aspect: solvents, solid particles
- C09K19/54—Additives having no specific mesophase characterised by their chemical composition
- C09K19/542—Macromolecular compounds
- C09K19/544—Macromolecular compounds as dispersing or encapsulating medium around the liquid crystal

Landscapes

Chemical & Material Sciences (AREA)
Crystallography & Structural Chemistry (AREA)
Engineering & Computer Science (AREA)
Materials Engineering (AREA)
Organic Chemistry (AREA)
Polymerisation Methods In General (AREA)
Liquid Crystal Substances (AREA)
Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Liquid Crystal (AREA)
Polyurethanes Or Polyureas (AREA)

IL10199392A 1991-10-23 1992-05-25 Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized IL101993A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US78059191A	1991-10-23	1991-10-23

Publications (1)

Publication Number	Publication Date
IL101993A true IL101993A (en)	1995-06-29

Family

ID=25120028

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL10199392A IL101993A (en)	1991-10-23	1992-05-25	Method for creating enhanced liquid crystal membranes with diffused polymer with initiating photo that can be copolymerized

Country Status (5)

Country	Link
EP (1)	EP0538553B1 (2)
JP (1)	JPH0768291B2 (2)
DE (1)	DE69202321T2 (2)
IL (1)	IL101993A (2)
TW (1)	TW255910B (2)

Families Citing this family (12)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
CA2139124A1 (en) *	1993-05-03	1994-11-10	Anthony F. Jacobine	Polymer dispersed liquid crystals in electron-rich alkene-thiol polymers
US5395550A (en) *	1994-03-31	1995-03-07	Raychem Corporation	Amphiphilic telomers
US5641426A (en) *	1994-04-29	1997-06-24	Minnesota Mining And Manufacturing Company	Light modulating device having a vinyl ether-based matrix
US5695594A (en) *	1996-01-05	1997-12-09	Raychem Corporation	Method of making a liquid crystal light valve
DE10257711B4 (de) *	2001-12-27	2019-09-26	Merck Patent Gmbh	Polymerisierbare monocyclische Verbindungen enthaltende Flüssigkristallmischungen
CA2487030A1 (en) *	2002-06-11	2003-12-18	Basf Aktiengesellschaft	(meth)acrylic esters of polyalkoxylated glycerine
EP2199273B1 (en)	2008-12-18	2018-02-21	Agfa Nv	Polymerizable photoinitiators and radiation curable compositions
WO2010133381A1 (en)	2009-05-18	2010-11-25	Agfa Graphics Nv	Polymerizable polymeric photoinitiators and radiation curable compositions
KR20140052240A (ko) *	2012-10-23	2014-05-07	동우 화인켐 주식회사	액정층 형성용 조성물 및 이를 이용하여 제조된 리타더
CN112469739A (zh)	2018-04-30	2021-03-09	巴斯夫欧洲公司	来自连续法的高分子量聚合物
CN113956423B (zh) *	2021-08-19	2023-05-26	Oppo广东移动通信有限公司	组合物、聚合物分散液晶、薄膜和电子设备
CN116107125A (zh) *	2023-03-02	2023-05-12	西京学院	一种三色液晶涂层显示装置

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
NL257095A (2) *	1959-10-21	1900-01-01
DE3534645A1 (de) *	1985-09-28	1987-04-02	Merck Patent Gmbh	Copolymerisierbare fotoinitiatoren
US4891152A (en) *	1987-12-28	1990-01-02	Hughes Aircraft Company	Dispersion of liquid crystal droplets in a photopolymerized matrix and devices made therefrom
WO1989006371A2 (en) *	1987-12-30	1989-07-13	Hughes Aircraft Company	Acrylate polymer-dispersed liquid crystal material and devices made therefrom
US4971719A (en) *	1989-09-22	1990-11-20	General Motors Corporation	Polymer dispersed liquid crystal films formed by electron beam curing

1992
- 1992-05-25 IL IL10199392A patent/IL101993A/en not_active IP Right Cessation
- 1992-05-29 TW TW81104228A patent/TW255910B/zh not_active IP Right Cessation
- 1992-06-01 EP EP19920109214 patent/EP0538553B1/en not_active Expired - Lifetime
- 1992-06-01 DE DE1992602321 patent/DE69202321T2/de not_active Expired - Lifetime
- 1992-06-01 JP JP4140758A patent/JPH0768291B2/ja not_active Expired - Lifetime

Also Published As

Publication number	Publication date
DE69202321D1 (de)	1995-06-08
EP0538553A1 (en)	1993-04-28
JPH0768291B2 (ja)	1995-07-26
EP0538553B1 (en)	1995-05-03
TW255910B (2)	1995-09-01
JPH05230122A (ja)	1993-09-07
DE69202321T2 (de)	1996-01-18

Legal Events

Date	Code	Title
1998-11-26	KB	Patent renewed
2002-06-30	KB	Patent renewed
2006-08-01	KB	Patent renewed
2010-10-31	KB	Patent renewed
2013-02-03	EXP	Patent expired

Publication	Publication Date	Title
EP0575791B1 (en)	1997-05-07	Liquid crystal composite layer of dispersion type, production method thereof and liquid crystal material to be used therein
US5516455A (en)	1996-05-14	Polymer dispersed liquid crystals in radiation curable electron-rich alkene-thiol polymer mixtures
EP0538553B1 (en)	1995-05-03	Copolymerizable initiator for improved polymer dispersed liquid crystal films
US4728547A (en)	1988-03-01	Liquid crystal droplets dispersed in thin films of UV-curable polymers
US5585035A (en)	1996-12-17	Light modulating device having a silicon-containing matrix
US5368770A (en)	1994-11-29	Method of preparing thin liquid crystal films
EP0809682B1 (en)	2001-04-25	Polymeric film
EP0205261B1 (en)	1990-09-19	Liquid crystal droplets dispersed in thin films of uv-curable polymers
KR101832811B1 (ko)	2018-02-28	복합 액정 조성물, 표시 소자 및 전계 검출기
US5604612A (en)	1997-02-18	Paper white PDLC system
CA2187889A1 (en)	1995-11-09	Light modulating device having a matrix prepared from acid reactants
EP0757710A1 (en)	1997-02-12	Light modulating device having a matrix prepared from allyl reactants
JP2807172B2 (ja)	1998-10-08	液晶光シャッター
JPH02116824A (ja)	1990-05-01	液晶デバイス
JP2021066875A (ja)	2021-04-30	重合性組成物および液晶調光素子
JP7796048B2 (ja)	2026-01-08	アントラキノン化合物を含有する調光用液晶組成物、その光硬化物及び調光素子
EP0540806A2 (en)	1993-05-12	Liquid crystal film
KR102316331B1 (ko)	2021-10-21	고분자 분산형 액정 조성물 및 이를 이용한 고분자 분산형 액정 필름
CN119535845A (zh)	2025-02-28	一种高对比度的染料pdlc调光膜
JP2879803B2 (ja)	1999-04-05	ポリマー分散型液晶複合膜およびその製法
JP3864429B2 (ja)	2006-12-27	液晶デバイス
CN116507969A (zh)	2023-07-28	改善的透明性的聚合物壁装置及其制造方法
Maschke et al.	1995	Electron beam processing for polymerization induced phase separation: Preparation of polymer dispersed liquid crystal films
JPH0862561A (ja)	1996-03-08	液晶プレポリマー組成物および該組成物を用いた液晶表示素子
Pane et al.	1999	Liquid crystal properties modulation for high performance PDLC films