CS237223B1 - 2,2-azoimidazole derivatives as dichroic pigments for liquid crystals - Google Patents

2,2-azoimidazole derivatives as dichroic pigments for liquid crystals Download PDF

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CS237223B1
CS237223B1 CS812901A CS290181A CS237223B1 CS 237223 B1 CS237223 B1 CS 237223B1 CS 812901 A CS812901 A CS 812901A CS 290181 A CS290181 A CS 290181A CS 237223 B1 CS237223 B1 CS 237223B1
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derivatives
liquid crystals
azoimidazole
dichroic
dichroic pigments
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CS812901A
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CS290181A1 (en
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Alexandr V Ivascenko
Valentina T Lazareva
Elena K Prudnikova
Vladimir G Rumjancev
Tamara S Pljusnina
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Ivaschenko Alexandr V
Valentina T Lazareva
Elena K Prudnikova
Vladimir G Rumjancev
Tamara S Pljusnina
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Publication of CS290181A1 publication Critical patent/CS290181A1/en
Publication of CS237223B1 publication Critical patent/CS237223B1/en

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Abstract

Vynález se týlfá nových derivátů 2,2- azo^midazolu-1, (, -bisbenzilidenemino4,4 -diaryl-2,2 -azoimidazolů, které mohou být použity jako dichroická barviva pro kapalné krystaly. Nové dichroická barviva mají úvS absorpční pásma ve viditelné oblasti spektra, přičemž dlouhovlnné pásmo je negativně a krátkovlnné pásmo je pozitivně dichroické.The invention relates to novel derivatives of 2,2- azo-imidazole-1, (, -bisbenzilidenemino4.4 diaryl-2,2-azoimidazoles which may be used as dichroic dyes for liquid crystals. New dichroic dyes have absorption absorption bands in the visible area spectrum, with the longwave band being negatively and the shortwave band is positive dichroic.

Description

1

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Rg H —

ΓΛβ: RjfHCN

Ia: Rj=OgHgj »2 = 4-¾ - CgH,;

Id: R *=4—CpHt-OGgH/ ; Rr> = 4—CnH-rp·—CglL;

Ib: rXh|;5 ^(^HprW··

Ir: R¢=4-02^50¾¾» Rg^-C^-OgHj^-CgH^J-CgH^;I«: R ¢=4-(0¾) 2 N ~CgH^; 2^^7^15^6¾ * I e: R ^=4— N θ£θ6^4 * 2^^7¾ 5^6¾ * yKa3aHmie np0H3B0ňHHe 2,2 -83οημηλη3Ολη Moryr hc-πολβ3οβητβοη b xanecTBe ληχροηηηηχ KpacaTejieft JUBL JKBA-KHX KpHCTaJHOB, ΚΟΤΟρΗβ MOryT Η0Π0ΛΒ30ΒβΤΒ0Η B ΠΟΛΗ—XpOMHHX CHCTeMax OTOdpaXeHHfl H ΧρΗΗβΗΗΗ ΗΗ$0ρΜ8ΠΗΗ,ΠρΗΗΠΗΠ padOTH KOTOpKX OCHOBaH Ha δφφβκτβ "Γ00ΤΒ-Χ03Η-hh” b atHAKHx xpucTajuiax. 237223 -2- JÍ3BecTH0 tíojn>moe κοληηθοτβο KpacaTOJieň jyia otakhxKpHCTajtUOB C ΠΟΛΟΧΗΤβΛΒΗΗΜ flHXp0H3M0M (I), ΚΟΤΟρΗβ ΙφΚnjxaHapnofl opneHTamra χηακογο KpncTajuia c πολοκητθλέ.ηο3OTBjíeiďpOTecKOft aHH3OTponne2 b sjíeKTpoonTiraecKoS j-raeS-κβ flamT OKpameHHoe padoněe ime. Ecjm xe κ 3JieKTpoj;aMínefiKH npajiDXHTB HanpjDKeHHe, dojn>tnee οπρβΑβΛβΗΗΟδ no-ρΟΓΟΒΟδ ΒβΛΗΗΗΗΗ, ΟρΗβΗΤβφΙΗ JKHflflOrO KpHCTajUIS CTHHO-BHTCH ΓΟΜβΟΤρΟΠΗΟδ, KpaCHTejEb Ηβ ΠΟΓΛΟΙΙ^ΘΤ ΟΒΘΤ H padO-aee nojie βηγληαητ ποητη decneeTHHM hjih cjaatío οκραιπβΗ-HHM.

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Uejo. αηηηογο H30dpeTeHHH - yBejnreemie πολοοκ no-rjioqeHZH b BHflHMOž odflacTH cneKTpa. IIocTaBJíeHHaH nejn. AOcraraeTOH οοβΑΗΗβΗζβΜ Bume-yita3aHHoft $opMyjm I.

CoeflHHeHZH oáuefi $opMyflH I nojiyneHK Β33ΗΜθΑβ2οτΒΗβΜPHflpa30HOB aMHHOryaHHflHHa C dpOMKeTOHaMH. ΠρΗΜβρ I. K pacTBopy 97,4r π-renTHJideH30JiapeT0- 237223 -3- $eHOHa b 100 mji yKcycHoa khcjioth npadaBJíHKT npa nepeMe-πιηβηηηη b TeneHae 1,5 ^íaca 23 mji dpoMa (TeMnepaTypa20-40°0). PeaiapiOHHyD Maccy BUflepacraaioT I nac npa20-25°C a BHJMBaBT b Bojiy. OpraimrecKzft cjioA aKCTpara-pyiDT ΧΛΟρΟφΟρΜΟΜ. OKCTpaKT npOMHBa»T 5^-HHM BOflHHMcoflOBHM pacTBopoM, BO^ofi a cymaT cyjn>$aTOM naTpuH. Pa-GTBop ^exaHTKpyOT, χ^οροφορΜ οτγοηηκτ b BaKyywe. IloJiy-aaDT I27,6r -dpoM^-renTHjiapeTC^HOHa, κοτορκΑ ac-nojn>3yBT Ha nocjiejiyKmeft cTajma a b npmaepax de3 aoiioji-HHTejn>Ho8 ohhctkh. 29,7r nojiyqeHHoro cd -dpoM-4-ren-τοθπθτοφθΗΟΗΗ a 32,4r óeH3ajn.j®rHjtryaHHJiTHJ5)a3OHaκηπητητ 5 nacoB b 300 mji BTaHOjia. ropanyro peaKnaoHHynMaccy φΗ j&TpyET, ocaflpK Ha φιυΐΒτρβ npoMHBaroT 100 μπKHHHmero 3TaHOJia, cymaT a nepeKpHCTajura3OBHBaDT H3MHHHMajttHoro Kojmree ctb3 yiccycHoro aHraflpafla, Ilojiywff0,5r 1,1* -ÓHCtíeH3HJIHHeHaMHHO-4,4 -,Π}Ι-(4-ΓβΠΤθφβΗθ)--2,2*-a3OHMHfla3OJia (Ia). SjíeKTpoHHHÉ οπβκτρ a ,ερηηηθ3λθμθητηογο aHajiH3a npHBejieHH b Tatíjnme I, IIpaMep 2. K pacTBopy 55,3r aMHHoryaHHUHHa cojihho-KHCjioro b 125 mji Bonn npadaBJKioT π-3T0KcadeH3ajiB(ne-γηλ b KOJuraecTBe 75,Ir. PeaKmiOHHyro Maccy HarpeBamT λο80°C a BHjíepjKHBaioT npa stoř TewinepaType 10 MHHyT, nocjieaero oxjiaxflaBT no 60°C a npadaBJíaioT npa nepeMernaBaHaapacTBop 22r ejncoro HaTpa b 75 μπ βολή. OxjiaawaroT £0κομηητηοΑ TeMnepaTypa, ocanoK οτφιυα,τροΒΗΒΗΒΤ, npoMHBa-K)T 50 mji xojto,hhoh bojch a cymaT. IIojiynaroT 99r π -3T0kch-deH3ajn.lnerHInryaHHjn?Hjipa3OHa, κοτορκΑ acnojn>3yOT Ha no-cjiejjyímefl cTauaa a npaMepax de3 jionojiHHTeji&HoA ohhctkh.29,7r 4?-dpoM- π -rennuiaiieTc^HOHa a 37,4r π-θτοκ-cadeH3ajn»serHKryaHHJirHjnpa3OHa noflBeprawp Β3βΗΜθΛθΑοτΒΗκ,Kaa b npaMepe I. ÍIojzynaET 0,7r I,I*-dac-( π -3Tokch-deH3HjnmeHaMHHo) -4,4* -λη-( π -renTHJs$eHHJieH)-2,21 -a30-HMHjia30Jia (Id). IIpaMep 3. npadaBJDWT npa nepeMernaBaHaa a TeMnepa-Type 50°C κ pacTBopy 30,9r 4-31^0-4’ -οκτπ;ιΰΗφβΗΐυΒ b 237223 -4- 50 μλ yKcycHoií khcjioth 5,1 μλ dpoMa b Teneime I aaca.PeaKUBOHHy» Maccy πβρβΜθπαϊΒβκτ I aac npa κομηβτηο2TeMnepaType, BtumBaioT b Bony, opramniecKHfl cjioh 3KCTpa-rnpyioT χΛοροφορΜΟΜ, sKCTpaKT npoMHBamT 5%-hhm bojihumpacTBopoM cojcu, 3aTeM βολο8 h cywaT cyjn>$aTOM HaTpaa.ΧΛοροφορΜ οτγοηηβτ b BanyyMe, a ocTaTOK nepeicpncTaji-JIH30BHBaDT H3 ΜΗΗΗΜ3ΛΒΗ0Γ0 ΚΟΤΠϊΉΘΟΤΒΒ 3TaH0JI3. IIOJiyaaiDT38r 4-dpoMaixeTiui-4 -OKTHJidH$eHHJia, H3 Ι9,6γ κοτοροΓΟh I6,5r tíeH3ajn.Beraj(ryaHHJiniípa30Ha, KaK b npHMepe I,nojiynaur 0,65r 1,1 -dHCdeH3HjnweHaMHHO-4,4 -^-(4-/4--OKTHj^eHHJieH/-$eHHjreH)-2,2,-a3OHM0fl;a3Ojia (Ib) . ΠρκΜβρ 4. ChhT63 npoBOjyiT aHaJionraió yKa3aHH0My bnpHMepe I. H3 19,6r 4-típoManeTHJi-4--OKTHJitíH$eHHJia hI8,7r 4-3T0KCHdeH3aju>^erHj(ryaHHJinijipa30Ha nojiynaroT 0,7rI ,I-dHC-(4-3TOKCHdeH3EurajieHaMHHo)-4,4í -jqa/4-(4-OKTHJi-φθΗΐυΚΗ)-φθΗΐυΐθΗ/2,2’-α3ΟΙΙΜΗΛ33ΟΛΒ (Ir). ΠρΗΜβρ 5. 0ΗΗΤθ3 npOBOflHT ΘΗΘΛΟΓϊΡίΗΟ yKa3aHHOMy ΒnpHMepe 2. 03 74,5r 4-OTMeTHJiaMHHodeH3ajn>Berima π 55,3raMHHoryaflHflHHa οοληηοκηολογο nojiynajoT ΙΟΙγ 4-αημθτηλ-aMHHotíeH3ajiBiierainyaHHJirH#pa3OHa. 03 37,3r nocjiejmeroh 29,7r -dpoM-4-renniJianeTo$eHOHa noJjyaaiDT I,2r1,1' -ÓHC—(.HHMeTHJiaMHHOdeHSHJIHAeHaMHHO)^ ,4* -HK-( Π -ΓβΠ-THJi$eHHJiefl)—2,2^ —a3OHMHna3ojia (Ijú . ΠρκΜβρ 6. CnHTe3 προΒΟΛΗΤ aHajioraaHO yKa3aHH0My bnpHMepe 2. 03 75,5r 4-HHTpodeH3ajttfleri«a H 55,3r ημηηο—ryaHHAHHa οοληηοκηολογο nojiynaroT 102,3r 4-HHTpodeH3ajcb-AerajiryaHHJirHjipa3OHa. 03 37,5r nocjieAHero h 29,7r ^-típoM-4-renTHJianeTo$eHOHa aHa.ro γηηηο yica3aHHOMy bnpHMepe I nojiynauT 0,07r 1,1 -dHC-(4-HHTpodeH3HJiHJteH-θμζηο)-4,4* — jjji—( π -renTHjťpeHHJieH)-2,2 -a30ZMHjca30Jia (Ie) ΠρκΜβρ 7. PacTBopauT 0,7-1,0^ 2,2 -a3OHMHfla3Ojia(I a-x) b XHAKOKpHCTajunnecKOĚ κομπο 3hhhh, npe^cTaBJuw-met cotíoft CMecB π —ιΐΗΒΗφβΗΗΛΟΒΗχ 3φπροΒ apoMaTHnecKHxκηολοτ. IIojiyneHHHft XHjncoKpHCTajuraraecKHfl Maiepnaji πομθ-maioT b 3JieKTpoonTHnecKyD nneitKy tojmihhoé 20 mkm c hojm- 237223 -5- poHBOM. HcxojiHaH opneHTanza wjtOKpHCTajunreecKoro Ma-Tepnajia iuaHapHaa, ιββθτ ot JKejrro-opaHKeBoro λο χθλτογο.Πρπ noflane HanpoeHHH 5-10 b opueHTannH raAKOKpHCTajura-πβοκοΓΟ MaTepitana μθηηθτοη Ha roMeoTponHym, npa stomHadJDO^aeTCH πβθτ οτ μθληηοβογο λο Φηολθτοβογο. Β Taójni-ue 2 npejioTaBJíeHH πολοοη πογλοπρηκη ( λ Mane., ημ)jKHjctOKpHCTajiJiHHecKHx MaTepaajioB, cosepoamiix προη3βοληηθ2,2,-8301001^330.^ (I a-r,e) η hx Λ0χροκ3Μ ( £ ) h Ha-ÓJDO«aeMHfl Β 3ΛΘΚΤρθΟΠΤΗΗβΟΚΟ0 ΗΗβίΙΚΘ ΠβρβΧΟΛ ΙξΒβΤΟΒ.

Taójnma I

ίΗΗΗΗΘ 3ΛΘΜβΗΤΗ0Γ0 aHaJIH3a Η 3JJBKTpOHHH6ΟΠβΚΤρΗ ΠΡ0Η3Β0ΛΗΗΧ 2,2 -a30HMHfla30Jia oómeS čpopMyjM I

Coejt- :T.iui. : : o0 HaífcneHO, % T—V"" N : BpyTTo-gšopMyjia . I 2 : 3 : 4 : 5 : 6 Ia 184,2-5-186 76,74 7,07 15,68 C4<&amp;2N8 IÓ I94,8řI96,I 74,25 6,90 13,89 C50H60 N 8°2 Ib 232ť233,5 79,82 7,01 12,31 C60H64N8 Ir 204ť206 78,78 7,11 II ,49 θ64%2^8°2 I» 2144-216 74,79 7,36 17,67 C50H62M 10 Ie 214 68,12 6,35 17,20 °46H50^I0°4 237223 -6-

ΠροΑΟΛκβΗΗβ TatíjmuH I

Coeji.: BraicjieHo, % n ; SjKKTpOHHHií CneKT]Jie Λ Mane. ( &amp; ) B 3TSH0) • • v: H : I : 7 : 8 : 9 : 10 Ia 77,05 7,32 15,63 281 (4,57), 385526 (4,13) (4,42), Id 74,59 7,51 13,92 292 (4,53), 345417 (4,25), 532 (4,37), (4,09) Ib 80,32 7,19 12,49 278x(4,50), 307417 (4,45), 533 (4,57),(4,05) Ir 78,03 7,36 11,37 278x(4,54), 310375 (4,46), 543 (4,63), (4,47) ΙΛ 74,78 7,78 17,44 326x(4,54), 351 (4,65),485X(4,3I), 540x(4,33),573 (4,37) Ie 68,46 6,26 17,35 286 (4,55), 394 (4,25), 533 (4,10) χ - njiew

Tatíjnma 2

KpacHTeja h ero co- : λaepjKaHHe β κηλκο- :ΚρΗ0ΤΒΛΠΗΗ60Κ02 KOM-ÍnO3HHHH : MaKC., hm: : : S : • · • · ΠβρβΧΟΛ ΙξΒΘ-TOB I : 2 : 3 : 4 1% coe,n. Ia 400 0,57 seOTHá-MaimHO- 530 - 0,24 BHH 0,7# coe,n. Id 430 0,50 ΧβΛΤΗΖ-φίΟΛΘ- 540 - 0,13 TOBHÍt 0,7# coeju Ib 430 0,64 jKejiTH2-$H0Jie- 550 - 0,29 tobhS 0,7# οοθλ. Ir 440 0,66 ΧδΛΤΗΗ-φΗΟΛΘ- ... 560 - 0,21 TOBH® 237223 -7- IIpojíOjmeHHe Tadjnma 2 I : 2 : 3 4 1% ΟΟΘΛ. Ie 400 0,47 ολτη2-Φηολθτοβη2 550 - 0J5 KSK BHflBO H3 ΠρΗΒΘΛθΗΗΗΧ ΙφΗΜβρΟΒ, ΗΟΒΗθ HpOH3BOJ[-Hue 2,2’-a3OHMHjia3OJia odmeií $opiviyjiH I MoryT c ycnexOMHcnojiB3OBaTBca b Ka^ecTBe ληχροηηηηχ KpacHTejief jmaΟΛΚΗΣ KpHCTaJUIOB. ΟΠΗ ΗΜβΚΤ ΛΒβ HOJTOCH ΠΟΓΛΟΠΙθΗΗΗ ΒBH.W03: oďnacTH cneKTpa, oj&amp;a H3 κοτορκχ προΗΒΛΗθτΠΟΛΟΚΗΤθΛΒΗΗίί, a ΛΡϊΓ^Η 0ΤρΗΙξ3ΤθΛΒΗΗ2 Λ0ΧρθΗ3Μ, Η ΟόθΟΠΘΗΗΒύΒΤ ΠρΗΘΜΛβΜΗΖ RUB. ΠρΗΚΤΗΗθCKHX ΙξθΛθδ ΙΧΒΘΤΟΒΟΗKOHTpacT. 237223 nchr' -8- ΦΟΡΜΠΙΑ Η30ΒΡΕΤΕΗΗΗ ΠρθΗ3ΒθΛΗΗ0 2,2*-a30HMHjia30Jia otímefi φορητοί:

R* H C N rse:

Ia: Rj = CgHg; R2= ló: Rj = 4-C2H50CgH4; R2 = 4-^15-¾¾1Ib: Rj = CgHg; R2 = 4-(4-CgHjy-CgH4) -- CgH4;

Ir: Rj = 4-C2HgOCgH4; R 2=4-(4-0gHpnr-CgH4)-CgH4;Ιπ: Rj = 4-(083)2 N C6H4; R 2=4-C7HI5-0gH4;

Ie: Rj - 4- Ηθ2 CgH4; R2=4-CyHjg-0gH4ΚΒΚ ΛΗΧΡΟΗΗΗΗΘ KpaCHTeJEH JVLH M£KHX KpHCTaJUIOB. 237223 9 A II Η O T A li Μ Η ΠρβΛποχβΗΗ HOBiie np0H3B0,nime 2,2'-a30HMK^a30Jia-1,1'-ÓHCÓeH3HJiH,nenaMHHO-4,4-flnapHji-2,2' -a3omw.a3Ojm, KOTopneΜΟΓΥΤ ΗΟΠΟΛΒ30Β3ΤΒΟΗ B KSHeCTBe AHXpOHHHHX KpaCHTejieŽ *71«κιρξίαιχ KpncTajuiOB. Hobho AHxpoHHHue xpacHTejni μμθϊοτ abgnOJIOCH ΠΟΓΛΟΠξβΗΗΗ B BHAHMOft OÓJiaCTH CIieKTpa, ΠρϊίΗθΜ flfflH-HOBOJIHOBaS nojioca OÓJia*aeT ΟΤρίΐρβΤΘΛΒΗ^Μ, a ΧΟρΟΤΚΟΒΟΛ-HOBaH - ΠΟΛΟΙΚΗΤΘΛΒΗΗΜ AHXP0H3M0M. 237223

1

£ £ HHOe Η300ρβΤΘΗΚ8 OTHOCHTCfl TO HOBHM ΧΗΜΗΗβΟΚΗΜCOeOTHeHHHM - K np0H3B0flHHM 2.2 -a30HMOQ30Jia odmeS $ opMyjm I

Rg H -

ΓΛβ: RjfHCN

Ia: Rj = OgHgj2 = 4-δ-CgH2;

Id: R * = 4-CpHt-OGgH); Rr> = 4 — CnH-rp · —CglL;

Ib: rXh |; ^ 5 ^ (^ HprW ··

Ir: R¢ = 4-02 ^ 50¾¾ »¾ »»ggggg ^ ^ ^Ogj ^ ^ -Cggggggg---ggg;;:::: R R 4- 4- 4- 4- 4- 4- 4- 4- 4- 4- 4- 4- 4- 4-; 2 ^^ 7 ^ 15 ^ 6¾ * I e: 7 ^ 5 ^ 6¾ * yKa3aHmie np0H3B0nHHe 2.2 -83οημηλη3Ολη Moryr hc-πολβ3οβητβοη b xanecTBe ληχροηηηηχ KHX KpHCTaJHOB, ΚΟΤΟρΗβ Ballad Η0Π0ΛΒ30ΒβΤΒ0Η b-ΠΟΛΗ XpOMHHX CHCTeMax OTOdpaXeHHfl H ΧρΗΗβΗΗΗ ΗΗ $ 0ρΜ8ΠΗΗ, ΠρΗΗΠΗΠ padOTH KOTOpKX OCHOBaH Ha δφφβκτβ "Γ00ΤΒ-Χ03Η-hh" b atHAKHx xpucTajuiax. 237,223 -2- JÍ3BecTH0 tíojn> moe κοληηθοτβο KpacaTOJieň jyia otakhxKpHCTajtUOB C ΠΟΛΟΧΗΤβΛΒΗΗΜ flHXp0H3M0M (I) ΚΟΤΟρΗβ ΙφΚnjxaHapnofl opneHTamra χηακογο KpncTajuia c πολοκητθλέ.ηο3OTBjíeiďpOTecKOft aHH3OTponne2 sjíeKTpoonTiraecKoS b j-Raes-κβ flamT OKpameHHoe padoněe ime. Ecjm xe κ 3JieKTpoj; aMínefiKH npajiDXHTB HanpjDKeHHe, milky> tnee οπρβΑβΛβΗΗΟδ no-ρΟΓΟΒΟδ ΒβΛΗΗΗΗΗ, ΟρΗβΗΤβφΙΗ JKHflflOrO KpHCTajUIS CTHHO-BHTCH ΓΟΜβΟΤρΟΠΗΟδ, KpaCHTejEb Ηβ ΠΟ ΛΟΙΙ ΘΤ ΟΒΘΤ ^ H-PADO AEE nojie βηγληαητ ποητη decneeTHHM hjih cjaatío οκραιπβΗ-HHM.

KpacHTejm c οτρΗΐ »τβΛΒΗΗΜ αεκροη3μομ b yKaeaHHHxBhnne ycJBOBHflx binge? otípaTHY »Kaprany, and KOMdHHamw Kpa-cnTejieit c ποΛΟίαιτβΛΒΗΗΜ h oTpunaTejiLHHM flnxpoH3MOMΠΟ3ΒΟΛΗβΤ riOJiyqHTB flByXflBeTHHS HHflHKaTOp. IIoCJieflHHĚμοχθτ dbíTt nojiyaeH πρκ ncnojn.3OBaHHH η οαηογο jmxpoHre-Horo KpacHTejH, ecjm oh κμθθτ αβθ αληηηοβοληοβηθ πολο-οκ B BHflHMOa OdJiaCTH ΟΠβΚΤρβ, ΠρΗΠβΜ 3TH ΠΟΛΟΟΗ flOJDKHNHM6TB flJIXpOH3M, npOTHBOnOJIOKHH2 ΠΟ 3HaKy. Έϊββηοτβθηηημ npHMepoM TAKORA Tuna ahxpohhhhx XPA-CHTejieÉ JMA soiflKHx KpacTajmoB ηβληβτοη dHCMepomaaHHHo-BHE KpacHTejm, κοτορκβ ημθβτ b bhakmoh odJiacTH cneKTpanojiocy πρκ 574 wt πολοκητθλβηκμ ahxpoh3mom c h nojiocynpH 482 HM flJIH KOTOpOH HadJEOflaeTCH ΟΤρΗΕξΒΤβΛΒΗΗΗ FLH-xpOH3M (2). OflHaKO yKa3aHHKe πολοοκ οηθηβ y3KHe (nojry nrapHHa-25wt) noaTOMy Η3ΒβοτΗΗβ αηχροηηηηθ itpacn-Secret (dHCMeponnaHKHOBHe) Ηβ Hanum npaKTHnecKoro πρηΜβ-ΗβΗΗΗ flJIH nOJiyneHKH KHflKOKpHCTaJUIEHeCKHX MaTepnaJIOBH3-3a cjiado BKpaxeHHoro πβθτοβογο KOHTpacTa.

Uejo. H30dpeTeHHH - yBejnreemie πολοοκ no-rjioqeHZH b BHflHMOz odflacTH cneKTpa. IIocTaBJiHHaH no. AOcraraeTOH οοβΑΗΗβΗζβΜ Bume-yita3aHHoft $ opMyjm I.

CoeflHHeHZH oáuefi $ opMyflH I nojiyneHK Β33ΗΜθΑβ2οτΒΗβΜPHflpa30HOB aMHHOryaHHflHHa C dpOMKeTOHaMH. ΠρΗΜβρ I. K pacTBopy 97,4r π-renTHJideH30JiapeT0- 237223 -3- $ eHOHa b 100 mji yKcycHoa khcjioth npadaBJiHKT npa nepeMe-πιηβηηηη b TeneHae 1,5 ^ ia 23 mji dpoMa (TeMnepaTypa20-40 ° 0). PeaiapiOHHyD Maccy BUflepacraaioT I nac npa20-25 ° C and BHJMBaBT b Bojiy. OpraimrecKzft cjioA aKCTpara-pyiDT ΧΛΟρΟφΟρΜΟΜ. OKCTpaKT nPOMHBa T 5 ^ -HHM BOflHHMcoflOBHM pacTBopoM, BO ^ ofi and cymaT cyjn> $ aTOM to TpuH. Pa-GTBop ^ exaHTKpyOT, χ ^ οροφορΜ οτγοηηκτ b BaKyywe. IloJiy-aaDT I27,6r -dpoM ^ -renTHjiapeTC ^ HOHa, κοτορκΑ ac-nojn> 3yBT Ha nocjiejiyKmeft cTajma ab npmaepax de3 aoiioji-HHTejn> Ho8 ohhctkh. 29,7r nojiyqeHHoro cd -dpoM-4-ren-τοθπθτοφθΗΟΗΗ and 32,4r óeH3ajn.j®rHjtryaHHJiTHJ5) a3OHaκηπητητ 5 nacoB b 300 mji BTaHOjia. ropanyro peaKnaoHHynMaccy φΗ j &amp; TpyET, ocaflpK Ha φιυΐΒτρβ npoMHBaroT 100 μπKHHHmero 3TaHOJia, and cymaT nepeKpHCTajura3OBHBaDT H3MHHHMajttHoro Kojmree ctb3 yiccycHoro aHraflpafla, Ilojiywff0,5r -ÓHCtíeH3HJIHHeHaMHHO 1,1 * 4,4 - Π} Ι- (4-ΓβΠΤθφβΗθ) - 2.2 * -a3OHMHfla3OJia (Ia). SjíeKTpoHHHÉ οπβκτρ a, b ερηηηθ3λθμθητηογο aHajiH3a npHBejieHH Tatíjnme I IIpaMep 2. pacTBopy 55,3r aMHHoryaHHUHHa cojihho KHCjioro b-125 np Bonn npadaBJKioT π-3T0KcadeH3ajiB (not γηλ KOJuraecTBe 75 b, Ir. PeaKmiOHHyro MACC HarpeBamT λο80 ° C BHjíepjKHBaioT NPA the TewinepaType 10 MHHyT, nocjeaero oxjiaxflaBT no 60 ° C, and npaaBaiaTaNaNaNaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaaa) T 50 mji xojto, hhoh fight and cymaT. Oj Ha aro oj -3 oj y y y y y y y y y y y y y y y y y y y y y y y cadeH3ajn »serHKryaHHJirHjnpa3OHa noflBeprawp Β3βΗΜθΛθΑοτΒΗκ, Kaa b npaMepe I. ÍIojzynaET 0.7r I, I * -dac- (π -3Tokch-deH3HjnmeHaMHHo) -4.4 * -λη- (π -renTHJs $ eHHJieH) -2.21 -a30 -HMHjia30Jia (Id). IIpaMep 3. npadaBJDWT npa nepeMernaBaHaa and TeMnepa-Type 50 ° C κ pacTBopy 30,9r 4-31 ^ 0-4 '-cap; ιΰΗφβΗΐυΒ b 237223 -4- 50 μλ yKcycHoii khcjioth 5,1 μλ dpoMa b Teneime I aaca.PeaKUBOHHy »MACC πβρβΜθπαϊΒβκτ I aac NPA κομηβτηο2TeMnepaType, BtumBaioT b Bony, opramniecKHfl cjioh 3KCTpa-rnpyioT χΛοροφορΜΟΜ, sKCTpaKT npoMHBamT 5% -hhm bojihumpacTBopoM cojcu, 3aTeM βολο8 h cywaT cyjn> $ b aTOM HaTpaa.ΧΛοροφορΜ οτγοηηβτ BanyyMe and ocTaTOK nepeicpncTaji JIH30BHBaDT-H3 ΜΗΗΗΜ3ΛΒΗ0Γ0 ΚΟΤΠϊΉΘΟΤΒΒ 3TaH0JI3. IIOJiyaaiDT38r 4-dpoMaixeTiui-4 -OKTHJidH $ eHHJia; 4 - OKTHj ^ eHHJieH / - $ eHHjreH) -2,2, -a3OHM0fl; 7r 4-3T0KCHdeH3aju> ^ erHj (ryaHHJinijipa30Ha nojiynaroT 0,7rI, I-dHC- (4-3TOKCHdeH3EurajieHaMHHo) -4,4i -jqa / 4- (4-OKTHJi-φθΗΐυΚΗ) -φθυυΐθΗ / 2,2'-α3ΟΙΙΜΗΛ33ΟΛΒ (Ir ). ΠρΗΜβρ fifth 0ΗΗΤθ3 npOBOflHT ΘΗΘΛΟΓϊΡίΗΟ yKa3aHHOMy ΒnpHMepe second 74,5r 03 4-OTMeTHJiaMHHodeH3ajn> Berima π 55,3raMHHoryaflHflHHa οοληηοκηολογο nojiynajoT ΙΟΙγ 4-αημθτηλ aMHHotíeH3ajiBiierainyaHHJirH # pa3OHa. 03 37,3r nocjiejmeroh 29,7r -dpoM 4-renniJianeTo $ eHOHa noJjyaaiDT I, 2r1,1 '-OHC - (HHMeTHJiaMHHOdeHSHJIHAeHaMHHO) ^ 4 * -HK- (Π-ΓβΠ-THJi eHHJiefl) -2,2 —a3OHMHna3ojia (Ijú. ΠρκΜβρ 6. CnHTe3 προΒΟΛΗΤ aHajioraaHO yKa3aHH0My bnpHMepe 2. 03 75,5r 4-HHTpodeH3ajttfleri and H 55,3r ημηηο — ryaHHAHHa οοληηοκηολογο nojiynaroT 102,3r 4-HHTpodeH3ajcb-AerajiryaHHJirHjipa3OHa. 03 37,5r nocjieAHero h 29,7r ^ -tiM-4-renTHiNiTo $ eHOHa aHa.ro γηηηο yica3aHHOMy bnpHMepe I nojiynauT 0,07r 1,1 -dHC- (4-HHTpodeH3HJiHJteH-θμζηο) -4,4 * - jjji— (π -renTHjťpeHHJieH) -2,2 -a30ZMHjca30Jia (Ie) 7.PacTBopauT 0,7-1,0 ^ 2,2 -a3OHMHfla3Ojia (I ax) b XHAKOKpHCTajunnecKOĚ κομπο 3hhhh, npe ^ cTaBJuw-met cotíoft 3φπροΒ apoMaTHnecKHxκηολοτ. IIojiyneHHHft XHjncoKpHCTajuraraecKHfl Maiepnaji πομθ-maioT b 3JieKTpoonTHnecKyD nneitKy tojmihhoé 20 mkm c hojm- 237223 -5- poHBOM. HcxojiHaH opneHTanza wjtOKpHCTajunreecKoro Ma-Tepnajia iuaHapHaa, ιββθτ OT-JKejrro opaHKeBoro λο χθλτογο.Πρπ noflane HanpoeHHH 5-10 b-opueHTannH raAKOKpHCTajura πβοκοΓΟ MaTepitana μθηηθτοη roMeoTponHym Ha NPA stomHadJDO ^ aeTCH πβθτ οτ μθληηοβογο λο Φηολθτοβογο. Β Taójni UE-2 npejioTaBJíeHH πολοοη πογλοπρηκη (λ Mane., Ημ) jKHjctOKpHCTajiJiHHecKHx MaTepaajioB, cosepoamiix προη3βοληηθ2,2, -8301001 ^ 330 ^ (I ar, e) η HX Λ0χροκ3Μ (£) h-Ha ÓJDO «aeMHfl Β 3ΛΘΚΤρθΟΠΤΗΗβΟΚΟ0 ΗΗβίΙΚΘ ΠβρβΧΟΛ ΙξΒβΤΟΒ.

Taójnma I

ΗΗΗΗΘ 3ΛΘΜβΗΤΗ0Γ0 aHaJIH3a Η 3JJBKTpOHHH6ΟΠβΚΤρΗ ΠΡ0Η3Β0ΛΗΗΧ 2.2 -a30HMHfla30Jia oómeS čpopMyjM I

Coejt-: T.iui. :: o0 Haífcneho,% T - V "" N: BpyTTo-gšopMyjia. I 2: 3: 4: 5: 6 Ia 184.2-5-186 76.74 7.07 15.68 C4 <&amp; 2N8 IÓ I94.8µI96, I 74.25 6.90 13.89 C50H60 N 8 ° 2 Ib 232ť233.5 79.82 7.01 12.31 C60H64N8 Ir 204ť206 78.78 7.11 II, 49 θ64% 2 ^ 8 ° 2 I »2144-216 74.79 7.36 17.67 C50H62M 10 Ie 214 68.12 6.35 17.20 ° 46H50 ^ I0 ° 4 237223 -6-

ΠροΑΟΛκβΗΗβ TatíjmuH I

Coeji: BraicjieHo,% n; SjKKTpOHHHii CneKT] Jie Mane. (&amp;) B 3TSH0) • in: H: I: 7: 8: 9: 10 Ia 77.05 7.32 15.63 281 (4.57), 385526 (4.13) (4.42) , Id 74.59 7.51 13.92 292 (4.53), 345417 (4.25), 532 (4.37), (4.09) Ib 80.32 7.19 12.49 278x (4 , 50), 307417 (4.45), 533 (4.57), (4.05) Ir 78.03 7.36 11.37 278x (4.54), 310375 (4.46), 543 (4) , 63), (4.47) ΙΛ 74.78 7.78 17.44 326x (4.54), 351 (4.65), 485X (4.3I), 540x (4.33), 573 (4 , 37) Ie 68.46 6.26 17.35 286 (4.55), 394 (4.25), 533 (4.10) χ - njiew

Tatijnma 2

KpacHTeja h ero co-: λaepjKaHHe β κηλκο-: ΚρΗ0ΤΒΛΠΗΗ60Κ02 COM-ÍnO3HHHH: MaKC., Hm::: S: • · • · ΠβρβΧΟΛ ΙξΒΘ-TOB I: 2: 3: 4 1% coe, n. Ia 400 0.57 seOTHa-MaimHO- 530 - 0.24 BHH 0.7 # coe, n. Id 430 0.50 ΧβΛΤΗΖ-φίΟΛΘ- 540 - 0.13 TOBHIT 0.7 # coeju Ib 430 0.64 jKejiTH2- $ H0Jie- 550 - 0.29 tobhS 0.7 # οοθλ. Ir 440 0.66 ΧδΛΤΗΗ-φΗΟΛΘ- ... 560 - 0.21 TOBH® 237223 -7- IIConnectOfHHe Tadjnma 2 I: 2: 3 4 1% ΟΟΘΛ. Ie 400 0.47 ολτη2-Φηολθτοβη2 550 - 0J5 KSK BHflBO H3 ΗΜρΗΜθΗΗΗΧ ΙφΗΜβρΟΒ, ΗΟΒΗθ HpOH3BOJ [-Hue 2,2'-a3OHMHjia3OJi me $ $ op op M ory ory ory T T T T T p p p p p p p p p p p p. 03 Η ΗΜ ΚΤ 03 TO TO TO TO 03 03 03. 03 03 03 03 03 03 03 03 03 03 03 03 03 03 03 03 Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ Χ. ΠρΗΚΤΗΗθCKHX ΙξθΛθδ ΙΧΒΘΤΟΒΟΗKOHTpacT. 237223 nchr '-8- ΦΟΡΜΠΙΑ Η30ΒΡΕΤΕΗΗΗ ΠρθΗ3ΒθΛΗΗ0 2,2 * -a30HMHjia30Jia otímefi φορητοί:

R * HCN rse:

Ia: Rj = CgHg; R 2 = 6: R 1 = 4-C 2 H 50 C 8 H 4; R 2 = 4- (15-β-Al): R 1 = C 8 H 8; R 2 = 4- (4-C 8 H 18 -C 8 H 4) -C 8 H 4;

Ir: Rj = 4-C2HgOCgH4; R 2 = 4- (4-OgHpnr-CgH 4) -C 8 H 4; R f = R 4 = 4- (O 3) 2 N C 6 H 4; R 2 = 4-C 7 H 15 OgH 4;

Ie: Rj - 4- 2θ2 CgH4; R2 = 4-CyHjg-0gH4ΚΒΚΚΒΚ KpaCHTeJEH JVLH M £ KHX KpHCTaJUIOB. 237223 9 A II TA OTA li OB Π OB OB OB OB OB H OB OB H ime OB OB OB OB OB OB OB OB OB OB OB KSHeCTBe AHXpOHHHHX KpaCHTejieŽ * 71 «κιρξίαιχ KpncTajuiOB. Hobho AHxpoHHHue xpacHTejni μμθϊοτ abgnOJIOCH B BHAHMOft OÓJiaCTH CIieKTpa, ΠρϊίΗθΜ flfflH-HOBOJIHOBaS nojioca OÓJia * aeT ΟΤρίΐρβΤΘΛΒΗ ^ Μ, and ΧΟρΟΤΚΟΒΟΛ-HOBaH - ΠΟΛΟΙΚΗΤΘΛΒΗΗΜ AHXP0H3M0M. 237223

Claims (1)

237223 PŘEDMĚT VYNÁLEZU Deriváty 2,2-ezoimldazolu obecného vzorce /NCHR,237223 SUBJECT OF THE INVENTION 2,2-Isoimldazole Derivatives of Formula (NCHR) 'λ/ / R,HCN kde Ia: R^CgHjj K2 = 4-C7H,5-CgH4; Ib: R, = 4-C2H5OCgH4; R2 = 4-ΟγΗ,j-Cgí^; Ic: H, e 7“θ6^4^“^6^4’ Id: R, = 4-C2H5OCgH4; R2 = 4-/4-C8H,7-CgH4/-CgH4;le: 8, = 4-/CH3/2NC6H4; R2 = 4-C7H,5-CgH4; If: R, = 4-NO2CgH4; R2 = 4-C7H15-CgH4 jako dichroická barvivo pro tekuté krystaly. Uznáno vynálezem na zákledě výsledků expertizy, provedené Státním výborem pro vynálezya objevy SSSR, Moskva, SU.λ / R, HCN where Ia: R ^CgHHj K2 = 4-C7H, 5-CgH4; Ib: R 1 = 4-C 2 H 5 OC 8 H 4; R 2 = 4-γγ, j-Cγ 3; Ic: H, e 7 "θ 6 ^ 4 ^" ^ 6 ^ 4 "Id: R 1 = 4-C 2 H 5 OC 4 H 4; R2 = 4- (4-C8H, 7-C8H4 / -C8H4; le: 8, = 4- (CH3) 2C6H4; R2 = 4-C7H5-C8H4; If: R 1 = 4-NO 2 C 8 H 4; R2 = 4-C7H15-CgH4 as dichroic liquid crystal dye. Recognized by the invention on the basis of expert results, conducted by the State Committee for Inventions and Discoveries of the USSR, Moscow, SU.
CS812901A 1980-07-31 1981-04-13 2,2-azoimidazole derivatives as dichroic pigments for liquid crystals CS237223B1 (en)

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SU802967265A SU946186A1 (en) 1980-07-31 1980-07-31 Derivatives of 2,2'-azoimidazole as dichronic dyes for liquid crystals

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