IL96468A - Nonlinear optical polymeric epoxy materials - Google Patents

Nonlinear optical polymeric epoxy materials

Info

Publication number: IL96468A
Authority: IL; Israel
Prior art keywords: nonlinear optical; epoxy; optical material; group; groups
Prior art date: 1989-11-27

Application number

IL9646890A

Other languages

English (en)

Hebrew (he)

Other versions

IL96468A0 (en

Inventor

John J Kester

H Craig Silvin

Original Assignee

Dow Chemical 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.)

1989-11-27

Filing date

1990-11-26

Publication date

1994-10-07

1990-11-26 Application filed by Dow Chemical Co filed Critical Dow Chemical Co

1991-08-16 Publication of IL96468A0 publication Critical patent/IL96468A0/xx

1994-10-07 Publication of IL96468A publication Critical patent/IL96468A/en

Links

230000003287 optical effect Effects 0.000 title claims description 144
239000000463 material Substances 0.000 title claims description 96
239000004593 Epoxy Substances 0.000 title claims description 90
239000000203 mixture Substances 0.000 claims description 64
239000010408 film Substances 0.000 claims description 42
239000003795 chemical substances by application Substances 0.000 claims description 41
150000001875 compounds Chemical class 0.000 claims description 39
125000003118 aryl group Chemical group 0.000 claims description 38
125000006575 electron-withdrawing group Chemical group 0.000 claims description 33
238000000034 method Methods 0.000 claims description 29
230000005684 electric field Effects 0.000 claims description 21
GYZLOYUZLJXAJU-UHFFFAOYSA-N diglycidyl ether Chemical class C1OC1COCC1CO1 GYZLOYUZLJXAJU-UHFFFAOYSA-N 0.000 claims description 17
239000004215 Carbon black (E152) Substances 0.000 claims description 16
230000001747 exhibiting effect Effects 0.000 claims description 16
229930195733 hydrocarbon Natural products 0.000 claims description 16
239000007795 chemical reaction product Substances 0.000 claims description 15
125000003055 glycidyl group Chemical group C(C1CO1)* 0.000 claims description 15
125000004433 nitrogen atom Chemical group N* 0.000 claims description 14
230000008569 process Effects 0.000 claims description 14
230000004044 response Effects 0.000 claims description 14
229910052739 hydrogen Inorganic materials 0.000 claims description 13
239000001257 hydrogen Substances 0.000 claims description 13
125000004435 hydrogen atom Chemical group [H]* 0.000 claims description 13
239000000758 substrate Substances 0.000 claims description 13
-1 glycidyl amines Chemical class 0.000 claims description 12
150000001412 amines Chemical class 0.000 claims description 11
239000003054 catalyst Substances 0.000 claims description 11
150000002430 hydrocarbons Chemical class 0.000 claims description 11
IISBACLAFKSPIT-UHFFFAOYSA-N bisphenol A Chemical compound C=1C=C(O)C=CC=1C(C)(C)C1=CC=C(O)C=C1 IISBACLAFKSPIT-UHFFFAOYSA-N 0.000 claims description 10
125000004432 carbon atom Chemical group C* 0.000 claims description 10
125000001931 aliphatic group Chemical group 0.000 claims description 8
239000000047 product Substances 0.000 claims description 8
150000002118 epoxides Chemical group 0.000 claims description 7
229930185605 Bisphenol Natural products 0.000 claims description 6
125000000217 alkyl group Chemical group 0.000 claims description 6
125000003700 epoxy group Chemical group 0.000 claims description 6
150000001408 amides Chemical class 0.000 claims description 5
150000008064 anhydrides Chemical class 0.000 claims description 5
238000000137 annealing Methods 0.000 claims description 5
238000004519 manufacturing process Methods 0.000 claims description 5
150000003568 thioethers Chemical class 0.000 claims description 5
125000001183 hydrocarbyl group Chemical group 0.000 claims description 4
125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 4
150000002460 imidazoles Chemical class 0.000 claims description 4
QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 claims description 4
230000000379 polymerizing effect Effects 0.000 claims description 4
229910052757 nitrogen Inorganic materials 0.000 claims description 3
150000003512 tertiary amines Chemical class 0.000 claims description 3
239000000835 fiber Substances 0.000 claims description 2
150000004714 phosphonium salts Chemical class 0.000 claims description 2
101100172290 Candida albicans (strain SC5314 / ATCC MYA-2876) ENG1 gene Proteins 0.000 claims 1
125000003277 amino group Chemical group 0.000 claims 1
239000002245 particle Substances 0.000 claims 1
229920000642 polymer Polymers 0.000 description 97
229920000647 polyepoxide Polymers 0.000 description 23
239000003822 epoxy resin Substances 0.000 description 21
230000000694 effects Effects 0.000 description 19
238000006243 chemical reaction Methods 0.000 description 18
MQJKPEGWNLWLTK-UHFFFAOYSA-N Dapsone Chemical compound C1=CC(N)=CC=C1S(=O)(=O)C1=CC=C(N)C=C1 MQJKPEGWNLWLTK-UHFFFAOYSA-N 0.000 description 15
239000010453 quartz Substances 0.000 description 14
VYPSYNLAJGMNEJ-UHFFFAOYSA-N silicon dioxide Inorganic materials O=[Si]=O VYPSYNLAJGMNEJ-UHFFFAOYSA-N 0.000 description 14
238000002156 mixing Methods 0.000 description 13
230000009477 glass transition Effects 0.000 description 12
230000010287 polarization Effects 0.000 description 12
239000000126 substance Substances 0.000 description 11
239000000376 reactant Substances 0.000 description 9
238000012360 testing method Methods 0.000 description 8
LNEPOXFFQSENCJ-UHFFFAOYSA-N haloperidol Chemical compound C1CC(O)(C=2C=CC(Cl)=CC=2)CCN1CCCC(=O)C1=CC=C(F)C=C1 LNEPOXFFQSENCJ-UHFFFAOYSA-N 0.000 description 7
239000000178 monomer Substances 0.000 description 7
239000011368 organic material Substances 0.000 description 7
229920005989 resin Polymers 0.000 description 7
239000011347 resin Substances 0.000 description 7
ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 6
HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 6
AFEQENGXSMURHA-UHFFFAOYSA-N oxiran-2-ylmethanamine Chemical compound NCC1CO1 AFEQENGXSMURHA-UHFFFAOYSA-N 0.000 description 6
238000006116 polymerization reaction Methods 0.000 description 6
125000001424 substituent group Chemical group 0.000 description 6
230000006870 function Effects 0.000 description 5
229920006254 polymer film Polymers 0.000 description 5
239000000243 solution Substances 0.000 description 5
239000010409 thin film Substances 0.000 description 5
LXBGSDVWAMZHDD-UHFFFAOYSA-N 2-methyl-1h-imidazole Chemical compound CC1=NC=CN1 LXBGSDVWAMZHDD-UHFFFAOYSA-N 0.000 description 4
VPWNQTHUCYMVMZ-UHFFFAOYSA-N 4,4'-sulfonyldiphenol Chemical class C1=CC(O)=CC=C1S(=O)(=O)C1=CC=C(O)C=C1 VPWNQTHUCYMVMZ-UHFFFAOYSA-N 0.000 description 4
HLBLWEWZXPIGSM-UHFFFAOYSA-N 4-Aminophenyl ether Chemical compound C1=CC(N)=CC=C1OC1=CC=C(N)C=C1 HLBLWEWZXPIGSM-UHFFFAOYSA-N 0.000 description 4
IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 4
150000004982 aromatic amines Chemical class 0.000 description 4
238000007872 degassing Methods 0.000 description 4
230000001419 dependent effect Effects 0.000 description 4
239000010410 layer Substances 0.000 description 4
150000002989 phenols Chemical class 0.000 description 4
239000002861 polymer material Substances 0.000 description 4
239000002904 solvent Substances 0.000 description 4
CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
BRLQWZUYTZBJKN-UHFFFAOYSA-N Epichlorohydrin Chemical compound ClCC1CO1 BRLQWZUYTZBJKN-UHFFFAOYSA-N 0.000 description 3
OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 description 3
ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
239000000987 azo dye Substances 0.000 description 3
230000015556 catabolic process Effects 0.000 description 3
230000001268 conjugating effect Effects 0.000 description 3
230000007423 decrease Effects 0.000 description 3
238000010790 dilution Methods 0.000 description 3
239000012895 dilution Substances 0.000 description 3
239000011521 glass Substances 0.000 description 3
RAXXELZNTBOGNW-UHFFFAOYSA-N imidazole Natural products C1=CNC=N1 RAXXELZNTBOGNW-UHFFFAOYSA-N 0.000 description 3
238000010348 incorporation Methods 0.000 description 3
229920003986 novolac Polymers 0.000 description 3
229920001568 phenolic resin Polymers 0.000 description 3
238000002360 preparation method Methods 0.000 description 3
239000011541 reaction mixture Substances 0.000 description 3
ARXJGSRGQADJSQ-UHFFFAOYSA-N 1-methoxypropan-2-ol Chemical compound COCC(C)O ARXJGSRGQADJSQ-UHFFFAOYSA-N 0.000 description 2
VILCJCGEZXAXTO-UHFFFAOYSA-N 2,2,2-tetramine Chemical compound NCCNCCNCCN VILCJCGEZXAXTO-UHFFFAOYSA-N 0.000 description 2
NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
KAKZBPTYRLMSJV-UHFFFAOYSA-N Butadiene Chemical compound C=CC=C KAKZBPTYRLMSJV-UHFFFAOYSA-N 0.000 description 2
FOQABOMYTOFLPZ-ISLYRVAYSA-N Disperse Red 1 Chemical compound C1=CC(N(CCO)CC)=CC=C1\N=N\C1=CC=C([N+]([O-])=O)C=C1 FOQABOMYTOFLPZ-ISLYRVAYSA-N 0.000 description 2
QIGBRXMKCJKVMJ-UHFFFAOYSA-N Hydroquinone Chemical compound OC1=CC=C(O)C=C1 QIGBRXMKCJKVMJ-UHFFFAOYSA-N 0.000 description 2
238000005481 NMR spectroscopy Methods 0.000 description 2
ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
239000002253 acid Substances 0.000 description 2
150000001336 alkenes Chemical class 0.000 description 2
230000015572 biosynthetic process Effects 0.000 description 2
238000004364 calculation method Methods 0.000 description 2
YCIMNLLNPGFGHC-UHFFFAOYSA-N catechol Chemical compound OC1=CC=CC=C1O YCIMNLLNPGFGHC-UHFFFAOYSA-N 0.000 description 2
238000004891 communication Methods 0.000 description 2
238000007796 conventional method Methods 0.000 description 2
238000004132 cross linking Methods 0.000 description 2
MGNZXYYWBUKAII-UHFFFAOYSA-N cyclohexa-1,3-diene Chemical compound C1CC=CC=C1 MGNZXYYWBUKAII-UHFFFAOYSA-N 0.000 description 2
238000000113 differential scanning calorimetry Methods 0.000 description 2
XXBDWLFCJWSEKW-UHFFFAOYSA-N dimethylbenzylamine Chemical compound CN(C)CC1=CC=CC=C1 XXBDWLFCJWSEKW-UHFFFAOYSA-N 0.000 description 2
150000002170 ethers Chemical class 0.000 description 2
238000011156 evaluation Methods 0.000 description 2
239000012467 final product Substances 0.000 description 2
SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 2
150000003944 halohydrins Chemical class 0.000 description 2
238000004128 high performance liquid chromatography Methods 0.000 description 2
230000006872 improvement Effects 0.000 description 2
238000005259 measurement Methods 0.000 description 2
230000009022 nonlinear effect Effects 0.000 description 2
239000004843 novolac epoxy resin Substances 0.000 description 2
JRZJOMJEPLMPRA-UHFFFAOYSA-N olefin Natural products CCCCCCCC=C JRZJOMJEPLMPRA-UHFFFAOYSA-N 0.000 description 2
235000020030 perry Nutrition 0.000 description 2
239000005011 phenolic resin Substances 0.000 description 2
235000013824 polyphenols Nutrition 0.000 description 2
238000012545 processing Methods 0.000 description 2
AOJFQRQNPXYVLM-UHFFFAOYSA-N pyridin-1-ium;chloride Chemical compound [Cl-].C1=CC=[NH+]C=C1 AOJFQRQNPXYVLM-UHFFFAOYSA-N 0.000 description 2
230000009467 reduction Effects 0.000 description 2
238000011160 research Methods 0.000 description 2
GHMLBKRAJCXXBS-UHFFFAOYSA-N resorcinol Chemical compound OC1=CC=CC(O)=C1 GHMLBKRAJCXXBS-UHFFFAOYSA-N 0.000 description 2
230000000717 retained effect Effects 0.000 description 2
NHGXDBSUJJNIRV-UHFFFAOYSA-M tetrabutylammonium chloride Chemical compound [Cl-].CCCC[N+](CCCC)(CCCC)CCCC NHGXDBSUJJNIRV-UHFFFAOYSA-M 0.000 description 2
VDZOOKBUILJEDG-UHFFFAOYSA-M tetrabutylammonium hydroxide Chemical compound [OH-].CCCC[N+](CCCC)(CCCC)CCCC VDZOOKBUILJEDG-UHFFFAOYSA-M 0.000 description 2
229920001187 thermosetting polymer Polymers 0.000 description 2
229960001124 trientine Drugs 0.000 description 2
IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 description 2
230000001960 triggered effect Effects 0.000 description 2
JYEUMXHLPRZUAT-UHFFFAOYSA-N 1,2,3-triazine Chemical compound C1=CN=NN=C1 JYEUMXHLPRZUAT-UHFFFAOYSA-N 0.000 description 1
WZCQRUWWHSTZEM-UHFFFAOYSA-N 1,3-phenylenediamine Chemical compound NC1=CC=CC(N)=C1 WZCQRUWWHSTZEM-UHFFFAOYSA-N 0.000 description 1
IYVYLVCVXXCYRI-UHFFFAOYSA-N 1-propylimidazole Chemical compound CCCN1C=CN=C1 IYVYLVCVXXCYRI-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
125000000954 2-hydroxyethyl group Chemical group [H]C([*])([H])C([H])([H])O[H] 0.000 description 1
XTTIQGSLJBWVIV-UHFFFAOYSA-N 2-methyl-4-nitroaniline Chemical compound CC1=CC([N+]([O-])=O)=CC=C1N XTTIQGSLJBWVIV-UHFFFAOYSA-N 0.000 description 1
VEORPZCZECFIRK-UHFFFAOYSA-N 3,3',5,5'-tetrabromobisphenol A Chemical compound C=1C(Br)=C(O)C(Br)=CC=1C(C)(C)C1=CC(Br)=C(O)C(Br)=C1 VEORPZCZECFIRK-UHFFFAOYSA-N 0.000 description 1
IYKLQEMQEGWXOQ-UHFFFAOYSA-N 3-(7-amino-4-chloro-1-oxoisochromen-3-yl)oxypropyl carbamimidothioate Chemical compound NC1=CC=C2C(Cl)=C(OCCCSC(=N)N)OC(=O)C2=C1 IYKLQEMQEGWXOQ-UHFFFAOYSA-N 0.000 description 1
ZRYCRPNCXLQHPN-UHFFFAOYSA-N 3-hydroxy-2-methylbenzaldehyde Chemical compound CC1=C(O)C=CC=C1C=O ZRYCRPNCXLQHPN-UHFFFAOYSA-N 0.000 description 1
YBRVSVVVWCFQMG-UHFFFAOYSA-N 4,4'-diaminodiphenylmethane Chemical compound C1=CC(N)=CC=C1CC1=CC=C(N)C=C1 YBRVSVVVWCFQMG-UHFFFAOYSA-N 0.000 description 1
TYMLOMAKGOJONV-UHFFFAOYSA-N 4-nitroaniline Chemical compound NC1=CC=C([N+]([O-])=O)C=C1 TYMLOMAKGOJONV-UHFFFAOYSA-N 0.000 description 1
JBRZTFJDHDCESZ-UHFFFAOYSA-N AsGa Chemical compound [As]#[Ga] JBRZTFJDHDCESZ-UHFFFAOYSA-N 0.000 description 1
229940123208 Biguanide Drugs 0.000 description 1
RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 1
RWSOTUBLDIXVET-UHFFFAOYSA-N Dihydrogen sulfide Chemical class S RWSOTUBLDIXVET-UHFFFAOYSA-N 0.000 description 1
229910001218 Gallium arsenide Inorganic materials 0.000 description 1
230000005374 Kerr effect Effects 0.000 description 1
239000004677 Nylon Substances 0.000 description 1
235000019502 Orange oil Nutrition 0.000 description 1
239000004642 Polyimide Substances 0.000 description 1
XUIMIQQOPSSXEZ-UHFFFAOYSA-N Silicon Chemical compound [Si] XUIMIQQOPSSXEZ-UHFFFAOYSA-N 0.000 description 1
239000007983 Tris buffer Substances 0.000 description 1
CKUAXEQHGKSLHN-UHFFFAOYSA-N [C].[N] Chemical group [C].[N] CKUAXEQHGKSLHN-UHFFFAOYSA-N 0.000 description 1
238000004847 absorption spectroscopy Methods 0.000 description 1
150000007513 acids Chemical class 0.000 description 1
230000004913 activation Effects 0.000 description 1
150000001298 alcohols Chemical class 0.000 description 1
150000001299 aldehydes Chemical class 0.000 description 1
229910052782 aluminium Inorganic materials 0.000 description 1
XAGFODPZIPBFFR-UHFFFAOYSA-N aluminium Chemical compound [Al] XAGFODPZIPBFFR-UHFFFAOYSA-N 0.000 description 1
235000019270 ammonium chloride Nutrition 0.000 description 1
150000003868 ammonium compounds Chemical class 0.000 description 1
238000013459 approach Methods 0.000 description 1
150000004945 aromatic hydrocarbons Chemical class 0.000 description 1
239000012298 atmosphere Substances 0.000 description 1
DMLAVOWQYNRWNQ-UHFFFAOYSA-N azobenzene Chemical compound C1=CC=CC=C1N=NC1=CC=CC=C1 DMLAVOWQYNRWNQ-UHFFFAOYSA-N 0.000 description 1
230000008901 benefit Effects 0.000 description 1
HTZCNXWZYVXIMZ-UHFFFAOYSA-M benzyl(triethyl)azanium;chloride Chemical compound [Cl-].CC[N+](CC)(CC)CC1=CC=CC=C1 HTZCNXWZYVXIMZ-UHFFFAOYSA-M 0.000 description 1
NDKBVBUGCNGSJJ-UHFFFAOYSA-M benzyltrimethylammonium hydroxide Chemical compound [OH-].C[N+](C)(C)CC1=CC=CC=C1 NDKBVBUGCNGSJJ-UHFFFAOYSA-M 0.000 description 1
230000001588 bifunctional effect Effects 0.000 description 1
150000004283 biguanides Chemical class 0.000 description 1
230000005540 biological transmission Effects 0.000 description 1
239000004841 bisphenol A epoxy resin Substances 0.000 description 1
238000009835 boiling Methods 0.000 description 1
239000004202 carbamide Substances 0.000 description 1
CREMABGTGYGIQB-UHFFFAOYSA-N carbon carbon Chemical group C.C CREMABGTGYGIQB-UHFFFAOYSA-N 0.000 description 1
239000011203 carbon fibre reinforced carbon Substances 0.000 description 1
239000011248 coating agent Substances 0.000 description 1
238000000576 coating method Methods 0.000 description 1
230000006835 compression Effects 0.000 description 1
238000007906 compression Methods 0.000 description 1
239000004020 conductor Substances 0.000 description 1
230000021615 conjugation Effects 0.000 description 1
238000012937 correction Methods 0.000 description 1
229920006037 cross link polymer Polymers 0.000 description 1
239000013078 crystal Substances 0.000 description 1
125000004093 cyano group Chemical group *C#N 0.000 description 1
125000004122 cyclic group Chemical group 0.000 description 1
238000006731 degradation reaction Methods 0.000 description 1
238000000280 densification Methods 0.000 description 1
QGBSISYHAICWAH-UHFFFAOYSA-N dicyandiamide Chemical compound NC(N)=NC#N QGBSISYHAICWAH-UHFFFAOYSA-N 0.000 description 1
150000001993 dienes Chemical class 0.000 description 1
125000006222 dimethylaminomethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])* 0.000 description 1
238000003618 dip coating Methods 0.000 description 1
230000005672 electromagnetic field Effects 0.000 description 1
230000005670 electromagnetic radiation Effects 0.000 description 1
238000005516 engineering process Methods 0.000 description 1
GKIPXFAANLTWBM-UHFFFAOYSA-N epibromohydrin Chemical compound BrCC1CO1 GKIPXFAANLTWBM-UHFFFAOYSA-N 0.000 description 1
JDVIRCVIXCMTPU-UHFFFAOYSA-N ethanamine;trifluoroborane Chemical compound CCN.FB(F)F JDVIRCVIXCMTPU-UHFFFAOYSA-N 0.000 description 1
LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 1
230000005669 field effect Effects 0.000 description 1
229910052736 halogen Inorganic materials 0.000 description 1
125000005843 halogen group Chemical group 0.000 description 1
150000002367 halogens Chemical class 0.000 description 1
WJRBRSLFGCUECM-UHFFFAOYSA-N hydantoin Chemical compound O=C1CNC(=O)N1 WJRBRSLFGCUECM-UHFFFAOYSA-N 0.000 description 1
229940091173 hydantoin Drugs 0.000 description 1
125000000743 hydrocarbylene group Chemical group 0.000 description 1
WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
238000003384 imaging method Methods 0.000 description 1
239000012535 impurity Substances 0.000 description 1
AMGQUBHHOARCQH-UHFFFAOYSA-N indium;oxotin Chemical compound [In].[Sn]=O AMGQUBHHOARCQH-UHFFFAOYSA-N 0.000 description 1
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230000001678 irradiating effect Effects 0.000 description 1
150000002576 ketones Chemical class 0.000 description 1
239000007788 liquid Substances 0.000 description 1
GQYHUHYESMUTHG-UHFFFAOYSA-N lithium niobate Chemical compound [Li+].[O-][Nb](=O)=O GQYHUHYESMUTHG-UHFFFAOYSA-N 0.000 description 1
230000007774 longterm Effects 0.000 description 1
229920002521 macromolecule Polymers 0.000 description 1
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230000003647 oxidation Effects 0.000 description 1
238000007254 oxidation reaction Methods 0.000 description 1
125000000466 oxiranyl group Chemical group 0.000 description 1
NRNFFDZCBYOZJY-UHFFFAOYSA-N p-quinodimethane Chemical class C=C1C=CC(=C)C=C1 NRNFFDZCBYOZJY-UHFFFAOYSA-N 0.000 description 1
125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 1
XYFCBTPGUUZFHI-UHFFFAOYSA-O phosphonium Chemical compound [PH4+] XYFCBTPGUUZFHI-UHFFFAOYSA-O 0.000 description 1
238000000053 physical method Methods 0.000 description 1
229920003229 poly(methyl methacrylate) Polymers 0.000 description 1
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239000002952 polymeric resin Substances 0.000 description 1
239000004926 polymethyl methacrylate Substances 0.000 description 1
WYOHGPUPVHHUGO-UHFFFAOYSA-K potassium;oxygen(2-);titanium(4+);phosphate Chemical compound [O-2].[K+].[Ti+4].[O-]P([O-])([O-])=O WYOHGPUPVHHUGO-UHFFFAOYSA-K 0.000 description 1
238000000425 proton nuclear magnetic resonance spectrum Methods 0.000 description 1
150000003856 quaternary ammonium compounds Chemical class 0.000 description 1
230000005855 radiation Effects 0.000 description 1
150000003254 radicals Chemical class 0.000 description 1
230000035484 reaction time Effects 0.000 description 1
238000010992 reflux Methods 0.000 description 1
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239000004065 semiconductor Substances 0.000 description 1
229910052710 silicon Inorganic materials 0.000 description 1
239000010703 silicon Substances 0.000 description 1
238000001542 size-exclusion chromatography Methods 0.000 description 1
239000007787 solid Substances 0.000 description 1
125000006850 spacer group Chemical group 0.000 description 1
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239000007921 spray Substances 0.000 description 1
238000005507 spraying Methods 0.000 description 1
230000006641 stabilisation Effects 0.000 description 1
238000011105 stabilization Methods 0.000 description 1
229910001220 stainless steel Inorganic materials 0.000 description 1
239000010935 stainless steel Substances 0.000 description 1
238000000859 sublimation Methods 0.000 description 1
230000008022 sublimation Effects 0.000 description 1
238000003786 synthesis reaction Methods 0.000 description 1
229920003002 synthetic resin Polymers 0.000 description 1
238000010998 test method Methods 0.000 description 1
GFZMLBWMGBLIDI-UHFFFAOYSA-M tetrabutylphosphanium;acetate Chemical compound CC([O-])=O.CCCC[P+](CCCC)(CCCC)CCCC GFZMLBWMGBLIDI-UHFFFAOYSA-M 0.000 description 1
239000012815 thermoplastic material Substances 0.000 description 1
229910001887 tin oxide Inorganic materials 0.000 description 1
238000012546 transfer Methods 0.000 description 1
230000007704 transition Effects 0.000 description 1
238000013519 translation Methods 0.000 description 1
IMFACGCPASFAPR-UHFFFAOYSA-N tributylamine Chemical compound CCCCN(CCCC)CCCC IMFACGCPASFAPR-UHFFFAOYSA-N 0.000 description 1
238000005406 washing Methods 0.000 description 1
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- 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
- 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
- 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
- C08G59/40—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 curing agents used
- C08G59/50—Amines
- C08G59/5033—Amines aromatic
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
- G02F1/3611—Organic materials containing Nitrogen
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
- G02F1/3613—Organic materials containing Sulfur
- G—PHYSICS
- G02—OPTICS
- G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
- G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
- G02F1/35—Non-linear optics
- G02F1/355—Non-linear optics characterised by the materials used
- G02F1/361—Organic materials
- G02F1/3615—Organic materials containing polymers
- G02F1/3616—Organic materials containing polymers having the non-linear optical group in the main chain

Landscapes

Physics & Mathematics (AREA)
Nonlinear Science (AREA)
Chemical & Material Sciences (AREA)
Health & Medical Sciences (AREA)
Chemical Kinetics & Catalysis (AREA)
Medicinal Chemistry (AREA)
Polymers & Plastics (AREA)
Organic Chemistry (AREA)
General Physics & Mathematics (AREA)
Optics & Photonics (AREA)
Epoxy Resins (AREA)

IL9646890A 1989-11-27 1990-11-26 Nonlinear optical polymeric epoxy materials IL96468A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US07/441,805 US5112934A (en)	1989-11-27	1989-11-27	Epoxy polymeric nonolinear optical materials based on glycidyl amines

Publications (2)

Publication Number	Publication Date
IL96468A0 IL96468A0 (en)	1991-08-16
IL96468A true IL96468A (en)	1994-10-07

Family

ID=23754364

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
IL9646890A IL96468A (en)	1989-11-27	1990-11-26	Nonlinear optical polymeric epoxy materials

Country Status (8)

Country	Link
US (1)	US5112934A (fr)
EP (1)	EP0430142A3 (fr)
JP (1)	JPH03188426A (fr)
KR (1)	KR910009769A (fr)
BR (1)	BR9006149A (fr)
CA (1)	CA2030901A1 (fr)
IL (1)	IL96468A (fr)
MY (1)	MY130101A (fr)

Families Citing this family (17)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US5160661A (en) *	1989-12-22	1992-11-03	Hoffmann-La Roche Inc.	Dioxanylpyridine
US5360884A (en) *	1990-08-03	1994-11-01	The Dow Chemical Company	Mesogenic glycidyl amine blends
US5112881A (en) *	1990-08-24	1992-05-12	University Of Lowell	Photocrosslinked second order nonlinear optical polymers
EP0477666B1 (fr) *	1990-09-24	1995-06-28	Siemens Aktiengesellschaft	Epoxy-résines réticulées à propriétés optiques non-linéaires
US5403520A (en) *	1990-09-25	1995-04-04	Ube Industries, Ltd.	Nonlinear optical device and optical signal processing unit
DE69230067T2 (de) *	1991-03-01	2000-01-05	The Dow Chemical Co., Midland	Mesogene Glycidylamine
DE69307189T2 (de) *	1992-06-05	1997-04-24	Matsushita Electric Ind Co Ltd	Nichtlinear optisches Material, Verfahren zur dessen Herstellung sowie Wellenlängenkonverter
US5347394A (en) *	1992-06-05	1994-09-13	Matsushita Electric Industrial Co., Ltd.	Nonlinear optical materials, method of manufacturing the same, and optical wavelength converter
US5539100A (en) *	1993-07-01	1996-07-23	The United States Of America As Represented By The United States Department Of Energy	Organic solid state switches incorporating porphyrin compounds and method for producing organic solid state optical switches
JPH0784292A (ja) *	1993-09-16	1995-03-31	Hoechst Japan Ltd	有機非線形光学材料
US5445854A (en) *	1993-11-29	1995-08-29	The Dow Chemical Company	Nonlinear optical epoxy-containing compositions and crosslinked nonlinear optical polymeric composition therefrom
US5466397A (en) *	1993-11-29	1995-11-14	The Dow Chemical Company	Nonlinear optically active pyrazolines and polymeric compositions containing moieties derived therefrom
US5464924A (en) *	1994-01-07	1995-11-07	The Dow Chemical Company	Flexible poly(amino ethers) for barrier packaging
US6294057B1 (en) *	1998-02-24	2001-09-25	Thames Water Utilities	Enhanced polymer activation system and apparatus
JP4394239B2 (ja) *	2000-02-29	2010-01-06	独立行政法人理化学研究所	二次非線形光学特性を有するポリマーフィルムの製造方法、ポリマーフィルム及び非線形光学素子
KR20130001144A (ko) *	2011-06-23	2013-01-03	(주)켐넥스	광활성 가교제 화합물, 이의 제조방법, 액정 배향제, 액정 배향막 및 액정 표시 소자
KR102875060B1 (ko) *	2023-12-08	2025-10-22	지에프텍 주식회사	무보빈 플라이백 변압기 및 이의 제조 방법

Family Cites Families (5)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
GB907844A (fr) *		1900-01-01
DE3622613A1 (de) *	1986-07-05	1988-01-14	Bayer Ag	Verfahren zur herstellung von polymeren netzwerken mit ueberstrukturen, entsprechende polymere netzwerke und ihre verwendung
DE3622610A1 (de) *	1986-07-05	1988-01-14	Bayer Ag	Fluessig-kristalline diglycidylverbindungen, ihre herstellung und verwendung in haertbaren epoxid-gemischen
JPH0796607B2 (ja) *	1987-09-07	1995-10-18	富山県	高分子圧電材及びその製造方法
JP2585018B2 (ja) *	1987-09-08	1997-02-26	富山県	圧電型感圧素子及びその製造方法

1989
- 1989-11-27 US US07/441,805 patent/US5112934A/en not_active Expired - Fee Related
1990
- 1990-11-23 MY MYPI90002078A patent/MY130101A/en unknown
- 1990-11-26 EP EP19900122554 patent/EP0430142A3/en not_active Withdrawn
- 1990-11-26 KR KR1019900019210A patent/KR910009769A/ko not_active Abandoned
- 1990-11-26 IL IL9646890A patent/IL96468A/en unknown
- 1990-11-26 CA CA002030901A patent/CA2030901A1/fr not_active Abandoned
- 1990-11-26 JP JP2318205A patent/JPH03188426A/ja active Pending
- 1990-11-27 BR BR909006149A patent/BR9006149A/pt not_active Application Discontinuation

Also Published As

Publication number	Publication date
EP0430142A2 (fr)	1991-06-05
EP0430142A3 (en)	1992-02-19
MY130101A (en)	2007-06-29
US5112934A (en)	1992-05-12
JPH03188426A (ja)	1991-08-16
BR9006149A (pt)	1991-09-24
CA2030901A1 (fr)	1991-05-28
IL96468A0 (en)	1991-08-16
KR910009769A (ko)	1991-06-28

Legal Events

Date	Code	Title	Description
1997-01-10	KB	Patent renewed

Publication	Publication Date	Title
US5112934A (en)	1992-05-12	Epoxy polymeric nonolinear optical materials based on glycidyl amines
Chen et al.	1992	Thermosetting polyurethanes with stable and large second-order optical nonlinearity
US4775215A (en)	1988-10-04	Nonlinear optical devices
Yu et al.	1992	Thermally curable second‐order nonlinear‐optical polymer
US5670603A (en)	1997-09-23	Polymers exhibiting nonlinear optical properties
Reck et al.	1990	Crosslinked epoxy polymers with large and stable nonlinear optical susceptibilities
US5279870A (en)	1994-01-18	Cured epoxy resins exhibiting nonlinear optical properties
EP0477665B1 (fr)	1994-11-23	Résines époxy réticulées à propriétés optiques non linéaires
US5266365A (en)	1993-11-30	Epoxy polymeric nonlinear optical materials
IL96471A (en)	1994-08-26	Nonlinear optical materials of polymers
US5080764A (en)	1992-01-14	Novel polymeric nonlinear optical materials from anisotropic dipolar monomers
US5173546A (en)	1992-12-22	Nonlinear optical materials
US5273793A (en)	1993-12-28	Nonlinear optical materials
US5273792A (en)	1993-12-28	Cured epoxy resins exhibiting second-order nonlinear optical response
US4826950A (en)	1989-05-02	Condensation polymers exhibiting nonlinear optical response
EP0477666B1 (fr)	1995-06-28	Epoxy-résines réticulées à propriétés optiques non-linéaires
Tapolsky et al.	1993	Maleimide-based crosslinkable electrooptic polymers with excellent thermal stability characteristics
US5288816A (en)	1994-02-22	Nonlinear optical aminoaryl hydrazones and nonlinear optical polymers thereof
Aramaki et al.	1994	Cross-linked poled polymer: Poling and thermal stability
US4867540A (en)	1989-09-19	Condensation polymers exhibiting nonlinear optical response
US5420172A (en)	1995-05-30	Cross-linked epoxy resins having non-linear optical properties
Schrader et al.	1998	New chromophores and polymers for second-order nonlinear optics
Goodson et al.	1996	The synthesis, characterization, and photochemical crosslinking of an NLO epoxy polymer
Lee	1997	Highly efficient and thermally stable second‐order nonlinear optical polymers
Leng et al.	2001	Modified nonlinear optical polyimide material for electro-optical modulator