PL244629B1 - Chromophore poly(2-[4-[(E)-(4-fluorophenyl)azo]-N-methylanilino]ethyl 2-methylprop-2-enoate) homopolymer and method of its preparation - Google Patents
Chromophore poly(2-[4-[(E)-(4-fluorophenyl)azo]-N-methylanilino]ethyl 2-methylprop-2-enoate) homopolymer and method of its preparation Download PDFInfo
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- PL244629B1 PL244629B1 PL432927A PL43292720A PL244629B1 PL 244629 B1 PL244629 B1 PL 244629B1 PL 432927 A PL432927 A PL 432927A PL 43292720 A PL43292720 A PL 43292720A PL 244629 B1 PL244629 B1 PL 244629B1
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- fluorophenyl
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- methylprop
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- enoate
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- 229920001519 homopolymer Polymers 0.000 title claims abstract description 19
- 238000000034 method Methods 0.000 title claims description 10
- -1 poly(2-[4-[(E)-(4-fluorophenyl)azo]-N-methylanilino]ethyl 2-methylprop-2-enoate) Polymers 0.000 title abstract description 6
- YEJRWHAVMIAJKC-UHFFFAOYSA-N 4-Butyrolactone Chemical compound O=C1CCCO1 YEJRWHAVMIAJKC-UHFFFAOYSA-N 0.000 claims abstract description 16
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 claims abstract description 16
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 claims abstract description 12
- 239000003999 initiator Substances 0.000 claims abstract description 8
- 239000000178 monomer Substances 0.000 claims abstract description 8
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 claims abstract description 8
- 239000000203 mixture Substances 0.000 claims abstract description 7
- VNCRFHLTCKBDNC-QURGRASLSA-N CC(C(=O)OCCN(C1=CC=C(C=C1)/N=N/C1=CC=C(C=C1)F)C)=C Chemical compound CC(C(=O)OCCN(C1=CC=C(C=C1)/N=N/C1=CC=C(C=C1)F)C)=C VNCRFHLTCKBDNC-QURGRASLSA-N 0.000 claims abstract description 5
- 239000011261 inert gas Substances 0.000 claims abstract description 5
- 238000006116 polymerization reaction Methods 0.000 claims abstract description 5
- 239000011541 reaction mixture Substances 0.000 claims abstract description 5
- 239000004342 Benzoyl peroxide Substances 0.000 claims abstract description 4
- OMPJBNCRMGITSC-UHFFFAOYSA-N Benzoylperoxide Chemical compound C=1C=CC=CC=1C(=O)OOC(=O)C1=CC=CC=C1 OMPJBNCRMGITSC-UHFFFAOYSA-N 0.000 claims abstract description 4
- 235000019400 benzoyl peroxide Nutrition 0.000 claims abstract description 4
- 238000006243 chemical reaction Methods 0.000 claims abstract description 4
- 238000010526 radical polymerization reaction Methods 0.000 claims abstract description 4
- OZAIFHULBGXAKX-UHFFFAOYSA-N 2-(2-cyanopropan-2-yldiazenyl)-2-methylpropanenitrile Chemical compound N#CC(C)(C)N=NC(C)(C)C#N OZAIFHULBGXAKX-UHFFFAOYSA-N 0.000 claims abstract description 3
- 239000012298 atmosphere Substances 0.000 claims abstract description 3
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 claims description 10
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 claims description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 claims description 6
- 239000012451 post-reaction mixture Substances 0.000 claims description 6
- 239000002244 precipitate Substances 0.000 claims description 6
- 235000019270 ammonium chloride Nutrition 0.000 claims description 5
- 230000015271 coagulation Effects 0.000 claims description 5
- 238000005345 coagulation Methods 0.000 claims description 5
- 239000011780 sodium chloride Substances 0.000 claims description 5
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 5
- XKRFYHLGVUSROY-UHFFFAOYSA-N Argon Chemical compound [Ar] XKRFYHLGVUSROY-UHFFFAOYSA-N 0.000 claims description 4
- 229910052757 nitrogen Inorganic materials 0.000 claims description 3
- 239000000047 product Substances 0.000 claims description 3
- 229910052786 argon Inorganic materials 0.000 claims description 2
- 238000001556 precipitation Methods 0.000 claims description 2
- 238000004519 manufacturing process Methods 0.000 abstract description 4
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 abstract description 2
- 229920000642 polymer Polymers 0.000 description 6
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 description 3
- IAZDPXIOMUYVGZ-WFGJKAKNSA-N Dimethyl sulfoxide Chemical compound [2H]C([2H])([2H])S(=O)C([2H])([2H])[2H] IAZDPXIOMUYVGZ-WFGJKAKNSA-N 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 229910052731 fluorine Inorganic materials 0.000 description 2
- 238000007699 photoisomerization reaction Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000005160 1H NMR spectroscopy Methods 0.000 description 1
- YCKRFDGAMUMZLT-UHFFFAOYSA-N Fluorine atom Chemical compound [F] YCKRFDGAMUMZLT-UHFFFAOYSA-N 0.000 description 1
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 1
- 238000010521 absorption reaction Methods 0.000 description 1
- 125000003277 amino group Chemical group 0.000 description 1
- 239000012300 argon 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
- 230000015572 biosynthetic process Effects 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 239000011737 fluorine Substances 0.000 description 1
- 125000001153 fluoro group Chemical group F* 0.000 description 1
- 239000004973 liquid crystal related substance Substances 0.000 description 1
- 125000005395 methacrylic acid group Chemical group 0.000 description 1
- 239000011859 microparticle Substances 0.000 description 1
- 239000002105 nanoparticle Substances 0.000 description 1
- 239000012299 nitrogen atmosphere Substances 0.000 description 1
- 230000003287 optical effect Effects 0.000 description 1
- IAMZDPGCACQJGF-UHFFFAOYSA-N phenyl-[4-(trifluoromethoxy)phenyl]diazene Chemical compound FC(OC1=CC=C(C=C1)N=NC1=CC=CC=C1)(F)F IAMZDPGCACQJGF-UHFFFAOYSA-N 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000193 polymethacrylate Polymers 0.000 description 1
- 238000010992 reflux Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
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- Polymerisation Methods In General (AREA)
- Polymerization Catalysts (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
Wynalazek ujawnia chromoforowy homopolimer poli(2-metyloprop-2-enian 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) o wzorze ogólnym 1, w którym n oznacza liczbę merów 2-metyloprop-2-enianu 2-[4-[(E)-(4- fluorofenylo)azo]-N-metylo-anilino]etylu) i mieści się w zakresie od 1 do 50. Wynalazek dotyczy również sposobu wytwarzania chromoforowego homopolimeru poli(2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N- metylo-anilino]etylu) o wzorze ogólnym 1, polegający na tym, że monomer 2-metyloprop-2-enian 2-[4-[(E)-4- fluorofenylo)azo]-N-metylo–anilino] etylu rozpuszcza się w mieszaninie tetrahydrofuranu, γ-butyrolaktonu i N,N-dimetyloformamidu o zawartości 60% objętościowych tetrahydrofuranu, 20% objętościowych γ-butyrolaktonu i prowadzi się polimeryzację rodnikową w obecności inicjatora: nadtlenku benzoilu lub 2,2'-azobis(izobutyronitrylu), utrzymując mieszaninę reakcyjną w temperaturze 70-100°C, i stosuje się od 8 do 12% wagowych inicjatora rodnikowego w stosunku do masy monomeru, przy czym reakcję prowadzi się w atmosferze gazu inertnego, a reakcję polimeryzacji prowadzi się od 68 do 72 godzin.The invention discloses a chromophore homopolymer poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl) of the general formula 1, wherein n is the number of units 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl 2-methylprop-2-enoate) and ranges from 1 to 50. The invention also relates to a process for preparing a chromophore homopolymer 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl poly(2-methylprop-2-enoate) of the general formula 1, consisting in the fact that the monomer 2-methylprop- 2-[4-[(E)-4- fluorophenyl)azo]-N-methyl-anilino]ethyl 2-enate is dissolved in a mixture of tetrahydrofuran, γ-butyrolactone and N,N-dimethylformamide containing 60% tetrahydrofuran by volume, 20 % by volume of γ-butyrolactone and radical polymerization is carried out in the presence of an initiator: benzoyl peroxide or 2,2'-azobis(isobutyronitrile), maintaining the reaction mixture at a temperature of 70-100°C, and using from 8 to 12% by weight of the radical initiator in relative to the weight of the monomer, the reaction is carried out in an inert gas atmosphere and the polymerization reaction lasts from 68 to 72 hours.
Description
Opis wynalazkuDescription of the invention
Przedmiotem wynalazku jest nowy chromoforowy homopolimer poli(2-metyloprop-2-enian 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu), który może być wykorzystany do optycznego zapisu informacji oraz do formowania fotoczułych mikro- i nanocząstek.The subject of the invention is a new chromophore homopolymer poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl), which can be used for optical recording of information. and to form photosensitive micro- and nanoparticles.
Przedmiotem wynalazku jest również sposób wytwarzania chromoforowego homopolimeru metakrylowego poli(2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu).The subject of the invention is also a method for preparing the chromophore methacrylic homopolymer poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl).
Znany jest z polskiego opisu patentowego nr 223365 homopolimer azobenzenowy posiadający w łańcuchu bocznym podstawnik 4-N-(5-metyloizoksazol-3-ilo)benzenosulfonamidowy, otrzymany w wyniku polimeryzacji rodnikowej. Położenie maksimum absorpcji opisanego homopolimeru znajduje się przy długości fali Xmax=346 nm.An azobenzene homopolymer with a 4-N-(5-methylisoxazol-3-yl)benzenesulfonamide substituent in the side chain, obtained as a result of radical polymerization, is known from the Polish patent description No. 223365. The location of the absorption maximum of the described homopolymer is at the wavelength Xmax = 346 nm.
Z kolei w publikacji D. Prescher, T. Thiele, R. Ruhmann, G. Schulz, Journal of Fluorine Chemistry 74 (1995) 185-189 opisano syntezę ciekłokrystalicznych polimetakrylanów i poliakrylanów zawierających mezogenne grupy boczne 4-trifluorometoksyazobenzenu. Reakcję polimeryzacji prowadzono w 70°C przez 24 godziny. Polimery otrzymano przez wylanie mieszaniny reakcyjnej do etanolu.In turn, the publication D. Prescher, T. Thiele, R. Ruhmann, G. Schulz, Journal of Fluorine Chemistry 74 (1995) 185-189 describes the synthesis of liquid crystal polymethacrylates and polyacrylates containing mesogenic side groups of 4-trifluoromethoxyazobenzene. The polymerization reaction was carried out at 70°C for 24 hours. The polymers were obtained by pouring the reaction mixture into ethanol.
Z kolei w publikacji L. Chen, Ch. He, Y. Huang, J. Huang, Y. Zhang, Y. Gao Journal of Applied Polymer Science (2016) 43540 (1-9) przedstawiono fotoaktywne właściwości fluoro-podstawionych azopolimerów opartych na Poliedrycznych Oligomerycznych Silseskwioksanach (POSS). Reakcję prowadzono w kolbie Schlenka, w atmosferze azotu, przez 24 godziny w obecności inicjatora rodnikowego - 2,2'-azobis(izobutyronitrylu). Zbadano kinetykę fotoizomeryzacji trans-cis otrzymanych polimerów oraz określono wpływ procesu fotoizomeryzacji na zwilżalność cienkich warstw polimerowych.In turn, in the publication by L. Chen, Ch. He, Y. Huang, J. Huang, Y. Zhang, Y. Gao Journal of Applied Polymer Science (2016) 43540 (1-9) presented the photoactive properties of fluoro-substituted azopolymers based on Polyhedral Oligomeric Silsesquioxanes (POSS). The reaction was carried out in a Schlenk flask, under a nitrogen atmosphere, for 24 hours in the presence of a radical initiator - 2,2'-azobis(isobutyronitrile). The kinetics of trans-cis photoisomerization of the obtained polymers were examined and the impact of the photoisomerization process on the wettability of thin polymer layers was determined.
Dotychczas nie został opisany w literaturze chromoforowy homopolimer metakrylowy poli(2-metyloprop-2-enian 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) oraz sposób jego wytwarzania.So far, the chromophore methacrylate homopolymer poly(2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl homopolymer) and its production method have not been described in the literature.
Istotą rozwiązania według wynalazku jest chromoforowy homopolimer poli(2-metyloprop-2-enian 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) o wzorze ogólnym 1, w którym n oznacza liczbę merów 2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) i mieści się w zakresie od 3 do 50.The essence of the solution according to the invention is the chromophore homopolymer poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl) of the general formula 1, in which n means the number of units of 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl 2-methylprop-2-enoate) and ranges from 3 to 50.
Wynalazek dotyczy również sposobu wytwarzania chromoforowego homopolimeru poli(2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) o wzorze ogólnym 1, w którym n przyjmuje wartości z zakresu od 3 do 50, charakteryzującego się tym, że monomer 2-metyloprop-2-enian 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu rozpuszcza się w mieszaninie tetrahydrofuranu, γ-butyrolaktonu i N,N-dimetyloformamidu o zawartości 60% objętościowych tetrahydrofuranu, 20% objętościowych γ-butyrolaktonu i prowadzi się polimeryzację rodnikową w obecności inicjatora: nadtlenku benzoilu lub 2,2’-azobis(izobutyronitrylu), utrzymując mieszaninę reakcyjną w temperaturze 70-100°C, i stosuje się od 8 do 12% wagowych inicjatora rodnikowego w stosunku do masy monomeru, przy czym reakcję prowadzi się w atmosferze gazu inertnego, reakcję polimeryzacji prowadzi się od 68 do 72 godzin, a w celu przyspieszenia koagulacji osadu homopolimeru wytrąconego z mieszaniny poreakcyjnej, poprzez wylanie mieszaniny poreakcyjnej do wody, stosuje się chlorek sodu lub chlorek amonu. Korzystnie jako gaz inertny stosuje się azot lub argon.The invention also relates to a process for preparing the chromophore homopolymer of poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl) of the general formula 1, wherein n has values ranging from 3 to 50, characterized by the fact that the monomer 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl 2-methylprop-2-enoate dissolves in a mixture of tetrahydrofuran, γ-butyrolactone and N,N-dimethylformamide containing 60% by volume of tetrahydrofuran, 20% by volume of γ-butyrolactone and radical polymerization is carried out in the presence of the initiator: benzoyl peroxide or 2,2'-azobis(isobutyronitrile), maintaining the reaction mixture at a temperature of 70-100°C, and from 8 to 12% by weight of a radical initiator in relation to the weight of the monomer is used, the reaction is carried out in an inert gas atmosphere, the polymerization reaction is carried out from 68 to 72 hours, and in order to accelerate the coagulation of the precipitate homopolymer precipitated from the post-reaction mixture, sodium chloride or ammonium chloride is used by pouring the post-reaction mixture into water. Nitrogen or argon is preferably used as the inert gas.
Korzystnie produkt wydziela się przez wytrącenie z wody lub mieszaniny wodno-lodowej.Preferably, the product is isolated by precipitation from water or a water-ice mixture.
Korzystnie w celu przyspieszenia koagulacji osadu homopolimeru wytrąconego z mieszaniny poreakcyjnej stosuje się chlorek sodu lub chlorek amonu.Preferably, sodium chloride or ammonium chloride is used to accelerate the coagulation of the homopolymer precipitate precipitated from the post-reaction mixture.
Przedmiot wynalazku przedstawiony jest w przykładach jego wytwarzania oraz określony wzorem ogólnym.The subject of the invention is presented in examples of its production and defined by a general formula.
Przykład 1Example 1
Sposób wytwarzania chromoforowego homopolimeru poli(2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) o wzorze 1.Method for preparing the chromophore homopolymer of poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl) of formula 1.
W kolbie okrągłodennej o pojemności 100 cm3, zaopatrzonej w chłodnicę zwrotną, umieszcza się 5,0 g (14,6 mmol) monomeru 2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu i 50 cm3 mieszaniny rozpuszczalników: tetrahydrofuran, γ-butyrolakton i N,N-dimetyloformamid o zawartości 60% objętościowych tetrahydrofuranu i 20% objętościowych γ-butyrolaktonu i miesza się do całkowitego rozpuszczenia osadu. Następnie dodaje się 0,4 g nadtlenku benzoilu jako inicjatora (8% wag. w stosunku do masy monomeru). Kolbę i chłodnicę przedmuchuje się azotem, mieszaninę reakcyjną ogrzewa do 70°C i utrzymuje w tej temperaturze przez 72 godziny. Po tym czasie zawartość kolby ochładza się do temperatury pokojowej, a następnie wylewa do mieszaniny wodno-lodowej. Za wiesinę wytrąconego polimeru pozostawia się w chłodziarce na minimum 24 godziny, dla poprawy koagulacji osadu dodaje się chlorek sodu lub chlorek amonu. Wytrącony osad odsącza się na lejku ze spiekiem, przemywa kilkukrotnie wodą destylowaną i suszy w temperaturze 60°C. Wydajność produktu otrzymanego tą metodą wynosi 95%.In a 100 cm 3 round-bottom flask equipped with a reflux condenser, 5.0 g (14.6 mmol) of 2-[4-[(E)-(4-fluorophenyl)azo 2-methylprop-2-enoate monomer are placed ]-N-methyl-anilino]ethyl and 50 cm 3 of a mixture of solvents: tetrahydrofuran, γ-butyrolactone and N,N-dimethylformamide with a content of 60% by volume of tetrahydrofuran and 20% by volume of γ-butyrolactone and mixed until the precipitate is completely dissolved. Then 0.4 g of benzoyl peroxide is added as an initiator (8% by weight relative to the weight of the monomer). The flask and condenser are purged with nitrogen, the reaction mixture is heated to 70°C and maintained at this temperature for 72 hours. After this time, the contents of the flask are cooled to room temperature and then poured into the water-ice mixture. The precipitated polymer suspension is left in the refrigerator for a minimum of 24 hours, and sodium chloride or ammonium chloride is added to improve the coagulation of the precipitate. The precipitate was filtered off on a sintered funnel, washed several times with distilled water and dried at 60°C. The yield of the product obtained by this method is 95%.
1HNMR (rozpuszczalnik DMSO-d6, wzorzec TMS): ~1,32 ppm protony od grup -CH2; ~1,52-1,99 ppm protony od grup -CH3 w łańcuchu głównym polimeru; ~3,10 CH3-N; ~4,13 ppm -CH2O-; ~6,756,77 ppm protony w pierścieniu fenylowym w pozycji orto do grupy aminowej; ~7,11-7,24 ppm protony w pierścieniu fenylowym w pozycji orto do atomu fluoru; ~7,80-7,81 ppm protony w pierścieniu fenylowym w pozycji orto i meta do grupy N=N.1HNMR (DMSO-d6 solvent, TMS standard): ~1.32 ppm protons from -CH2 groups; ~1.52-1.99 ppm protons from -CH3 groups in the polymer main chain; ~3.10 CH3-N; ~4.13 ppm -CH2O-; ~6,756.77 ppm protons in the phenyl ring ortho to the amino group; ~7.11-7.24 ppm protons in the phenyl ring ortho to the fluorine atom; ~7.80-7.81 ppm protons in the phenyl ring in the ortho and meta positions to the N=N group.
Przykład 2Example 2
Sposób wytwarzania chromoforowego homopolimeru poli(2-metyloprop-2-enianu 2-[4-[(E)-(4-fluorofenylo)azo]-N-metylo-anilino]etylu) o wzorze 1 jak w przykładzie 1, przy czym polimeryzację prowadzi się w temperaturze 100°C przez 68 godzin, w atmosferze argonu.A method for preparing the chromophore homopolymer of poly(2-methylprop-2-enoate 2-[4-[(E)-(4-fluorophenyl)azo]-N-methyl-anilino]ethyl) of formula 1 as in example 1, wherein polymerization is carried out at a temperature of 100°C for 68 hours, under an argon atmosphere.
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