CS273752B1 - Colour copolymers of 2-dimethylaminoethylmetacrylate with n-phenyl-maleatimide and method of their preparation - Google Patents
Colour copolymers of 2-dimethylaminoethylmetacrylate with n-phenyl-maleatimide and method of their preparation Download PDFInfo
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- CS273752B1 CS273752B1 CS708488A CS708488A CS273752B1 CS 273752 B1 CS273752 B1 CS 273752B1 CS 708488 A CS708488 A CS 708488A CS 708488 A CS708488 A CS 708488A CS 273752 B1 CS273752 B1 CS 273752B1
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- Prior art keywords
- copolymers
- colour
- dimethylaminoethylmethacrylate
- preparation
- phenylmaleinimide
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- 229920001577 copolymer Polymers 0.000 title claims abstract description 22
- 238000002360 preparation method Methods 0.000 title claims description 5
- 238000000034 method Methods 0.000 title claims description 3
- 238000006243 chemical reaction Methods 0.000 claims abstract description 8
- -1 2-dimethylaminoethyl ethyl Chemical group 0.000 claims description 2
- 230000008569 process Effects 0.000 claims description 2
- JKNCOURZONDCGV-UHFFFAOYSA-N 2-(dimethylamino)ethyl 2-methylprop-2-enoate Chemical compound CN(C)CCOC(=O)C(C)=C JKNCOURZONDCGV-UHFFFAOYSA-N 0.000 abstract description 10
- HIDBROSJWZYGSZ-UHFFFAOYSA-N 1-phenylpyrrole-2,5-dione Chemical compound O=C1C=CC(=O)N1C1=CC=CC=C1 HIDBROSJWZYGSZ-UHFFFAOYSA-N 0.000 abstract description 7
- 239000000203 mixture Substances 0.000 abstract description 4
- 230000008859 change Effects 0.000 abstract description 2
- 150000003949 imides Chemical class 0.000 abstract description 2
- 230000002441 reversible effect Effects 0.000 abstract description 2
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 12
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 description 6
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 4
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 4
- CERQOIWHTDAKMF-UHFFFAOYSA-M Methacrylate Chemical compound CC(=C)C([O-])=O CERQOIWHTDAKMF-UHFFFAOYSA-M 0.000 description 4
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000000463 material Substances 0.000 description 3
- 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 description 2
- 125000003006 2-dimethylaminoethyl group Chemical group [H]C([H])([H])N(C([H])([H])[H])C([H])([H])C([H])([H])* 0.000 description 2
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 2
- 238000002835 absorbance Methods 0.000 description 2
- 230000002378 acidificating effect Effects 0.000 description 2
- 230000001476 alcoholic effect Effects 0.000 description 2
- 230000008033 biological extinction Effects 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000977 initiatory effect Effects 0.000 description 2
- 229920005604 random copolymer Polymers 0.000 description 2
- 239000002253 acid Substances 0.000 description 1
- 230000009471 action Effects 0.000 description 1
- 150000001408 amides Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000003086 colorant Substances 0.000 description 1
- 238000012505 colouration Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 230000001351 cycling effect Effects 0.000 description 1
- 239000011521 glass Substances 0.000 description 1
- 230000003993 interaction Effects 0.000 description 1
- 239000012528 membrane Substances 0.000 description 1
- 229910052757 nitrogen Inorganic materials 0.000 description 1
- 238000006116 polymerization reaction Methods 0.000 description 1
- 230000000379 polymerizing effect Effects 0.000 description 1
- 238000003918 potentiometric titration Methods 0.000 description 1
- 238000001556 precipitation Methods 0.000 description 1
- 239000007870 radical polymerization initiator Substances 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 238000007789 sealing Methods 0.000 description 1
- 230000028327 secretion Effects 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 230000007704 transition Effects 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 1
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- Medicinal Preparation (AREA)
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Description
CS 273752 BlCS 273752 Bl
Vynález ee týká barevných kopolymerů Z-diBethylealnoethylnethakrylátu β N-fenylmaleinimldem»t jejich přípravy a barevné přeměny v závislosti na pH prostředí» Tyto kopolyaery,' Jejích syntéza a barevné přechsdy nebyly doeud v literatuře popeány.The invention relates to color copolymers of Z-di-ethylealnoethyl methacrylate β N-phenylmaleimide, and their preparation and color conversion depending on the pH of the environment. These copolymers, their synthesis and color transitions have not been described in the literature.
Podatetou vynálezu jeou barevná kepolyeery 2-dlmethylaminosthylmsthakrylátu β N-fenyleeleinimidom^l která obeehují v řetizci opakující ·β jednotky 2-dieethylaainoethylmethakrylátu vzorce ISUMMARY OF THE INVENTION The present invention relates to color cepolymers of 2-dimethylaminosthyl methacrylate β N-phenyleeleinimidome which contain in the chain repeating β units of 2-diethylaainoethyl methacrylate of formula I
CHg — ch2— c — (I) 'COOCH2CH2N(CH3)2 a N-fenylmaleinimiduí. vzorce IICH 2 --CH 2 - c - (I) COOCH 2 CH 2 N (CH 3 ) 2 and N-phenylmaleimide. of formula II
CH CH — Γ co coCH CH - co what what
a obsahat» 5 al 97 % molárnich vestavěného 2-dieethyle»inoetbylm®thakryXátu« Reverslbllni zrnina jejich barevnosti probíhá v závislosti ne pH prostředí v rozmezí pH 3»'6 až 4,0.and contain < 5 > l and 97 mole% of built-in 2-diethyl-ino-ethyl-methyl-thacrylate.
Této barevné přeměny uvedených kopelymerů lze využit k ecidobazlcké Indikaci,This color conversion of these copelymers can be used for the ecobasic Indication,
Podle vynálezu spočívá zpúaob přípravy těchto kopolymerů v tom,' že ae polymeruje směe 2-dlmethylaminoethylmethakrylátu β N-fenylaslelnlmidem v benzenu,' acetonu nebo v jiném rozpouětědla obou komonomerů účinkem iniciátoru radikálová polymerace^ například 2,2'azo-ble(íeobutyronitrilu), Molární poměr 2-dimethyleminoethylmethakrylát/N-fenylmilelnimid ee může měnit v rozmezí 0,'02 až 40« Teplota kopolymerace ae voli taki! aby iniciační centra vznikala dostatečnou rychloati. Zahájeni kopolymerace a její průběh je charakterizován vznikem červeného zabarvení reakčni směsí, Červeně zbarvené jeou také ziakané kopolyiBory, izolované srážením polymeračních směsi hexane·. Hoeopolyaery 2-diBethylaminoethylmethskrylátu i N-fenylmaleinimidu jaou bezbarvé.According to the invention, the preparation of these copolymers consists in polymerizing a mixture of 2-dimethylaminoethyl methacrylate with β N-phenylaryl amide in benzene, acetone or another solvent of both comonomers by the action of a free radical polymerization initiator such as 2,2'azobutyronitrile. The molar ratio of 2-dimethyleminoethyl methacrylate / N-phenylmilelimide ee can vary between 0.02 and 40 ° C. so that the initiation centers can produce sufficient speed. The initiation of the copolymerization and its course is characterized by the formation of a red colouration of the reaction mixture. The red-colored copolymers are also isolated, isolated by precipitation of the polymerization mixtures with hexane. Both the 2-dimethylaminoethyl methacrylate and N-phenylmaleimide hoeopolymers are colorless.
Barevnost kopolymerů. je způsobena interakci aminových a kerbonylovýoh skupin vestavěných komonomerů,' doprovázenou tvorbou chromoforniho seskupeni v řetězci podlá schématu IColor of copolymers. is due to the interaction of amine and kerbonyl groups of the built-in comonomers, accompanied by the formation of a chromophoric group in the chain according to Scheme I
Potenclometrická tttrace kopolymerů kyselin··! ukazuje,' že v rozsahu pH 3,¾ až 4,0 přechází zabudovaný 2-di(aethylaminoethyleethakrylét na odpovídající sůl (iontovou formu),1 což má za následek zruěoni cbromoforni etruktury β proto Jejich odbarveni. Po zalkall zováni nabývají kopolyméry opět původní červené barvy,Potentiometric tttration of acid copolymers ··! shows that in the pH range of 3 ¾ to 4.0, the incorporated 2-di (aethylaminoethyleethacrylate) is converted to the corresponding salt (ionic form) 1, resulting in the discoloration of the bromoformic β structures, thereby discolouring them. colors,
Kopolyméry obsahující vice než 50 % nalérnich 2-dlmethylaminoethylmethekryláUi jaouCopolymers containing more than 50% of linear 2-dimethylaminoethyl methecrylates are present
CS 273752 Bl dobře rozpustné v benzenu, acetonu, chloroformu, dimethylformamidu a vodné alkoholických roztocích,’ zetiaco vyééí obeah vestavěného imidu vede ke zhorěeni rozpustnosti,' popřípadě k vylučováni pevného produktu už během kopolymerece0 EN 273 752 Bl soluble in benzene, acetone, chloroform, dimethylformamide, and aqueous alcoholic solutions, 'zetiaco vyééí Obeah built imide leads to zhorěeni solubility, secretion or for solid even during kopolymerece 0
Způsob přípravy kopolymerů 2-dimethylaminoethylmethakrylátu s N-fenylmaleinimidem a jejioh charakteristiky jaou uvedeny v následujících příkladech.The preparation of 2-dimethylaminoethyl methacrylate-N-phenylmaleimide copolymers and their characteristics are given in the following examples.
Přiklad 1Example 1
Roztok obsahující 2,1 g 2-dlmethylamlnoethylaethakrylátu,J O,Q g N-fenylmeleinimidu, 0,‘03 g 2,2*-azo-bis-(isobutyronitrilu) a 5 cm benzenu se umístí do skleněné ampule, probublá 20 minut dusíkem a ampule ae po zataveni ponechá 5 hodin v thermostatu při 50 °C, Osminásobným množstvím hexanu se potom vyloučí červený statistický kopolymér (0,7 g, tj.A solution containing 2.1 g of 2-dimethylamino-ethylaethacrylate, JO, Q g of N-phenylmeleinimide, 0. 03 g of 2,2'-azo-bis- (isobutyronitrile) and 5 cm of benzene is placed in a glass vial, purged with nitrogen for 20 minutes and The vial is left in the thermostat at 50 ° C for 5 hours after sealing. A red random copolymer (0.7 g, i.
% konverze),1 který se přesráži hexanem z chloroformového roztoku, Potenciometrickou títraci ae zjistí,] že obsahuje 57 % molárnich zabudovaného 2-dieiethylamlnoethylmethakrylátu. Červený vodně alkoholický roztok kopolymerů (0,‘66 g kopolymeru/dm roztoku s obsahem 65 % hmotnostních vody) se při pH » 3,6 odbarvujeo Extinkčni koeficient v tomto kyselém prostředí mé hodnotu 0,028 dm3g“‘'’ca“’1· při vlnové délce Λ 510 nm a absorbanci% Conversion), one which was reprecipitated from chloroform solution with hexane, potentiometric titrations ae finds] that contains 57 mol% of 2-dieiethylamlnoethylmethakrylátu built. The red aqueous alcoholic solution of the copolymer (0 '66 g copolymer / dm solution containing 65% water) at pH »3.6 odbarvujeo extinction coefficient in the acidic environment of my 0.028 dm 3 g '''' ca '' 1 · At wavelength Λ 510 nm and absorbance
Bi0X *5 1 1Bi0X * 5 1 1
0,0183, Původní naokyselený kopolymér (pH 7,6) má extinkčni koeficient 0,:131 dmJg“ cm“ při vlnové délce λ « 502 nm a absorbanci 0,0863, Po zalkalizování roztok opět zčerΜ0Χ vená.0.0183, The original acidified copolymer (pH 7.6) has an extinction coefficient of 0: 131 dm J g "cm" at a wavelength λ 50 502 nm and an absorbance of 0.0886. After alkalization, the solution is reddened.
Přiklad 2Example 2
Stejným způsobem jako v přikladu 1 se polymeruje 6 hodin při 50 °C směs sestávejici z 3,]9 g 2-dlmethylamlnoethylaethakrylátu0,1 g N-fenylmalelnimidu,] O,.04 g 2,2'-azo-bis(isobutyronitrilu) a 8 cm3 benzenu. Připravený statistický kopolymér (1,6 g, tj. 40 % konverze) obsahuje 97 % molárnich 2-dimethylaminoethylmethakrylátu, Jeho barevné vlastnosti se shoduji s charakteristikami uvedenými v příkladě 1,In the same manner as in Example 1, a mixture consisting of 3.9 g of 2-dimethylaminoethyl ethyl methacrylate and 0.1 g of N-phenylmalelimide, 10.04 g of 2,2'-azobis (isobutyronitrile) was polymerized at 50 ° C for 6 hours. 8 cm 3 of benzene. The prepared random copolymer (1.6 g, i.e. 40% conversion) contains 97 mole% of 2-dimethylaminoethyl methacrylate. Its color properties are identical to those given in Example 1,
Příklad 3Example 3
Stejným způsobem jako v přikladu 1 ae připraví ze aměei Qi]l g 2-dimethylaminoethylmethakrylétuJ 1^9 g N-fenylmaleinimidu^ 0,02 g 2,2'-azo-bia-(Ísobutyronltrilu) a 10 cm3 za 144 hodin při 50 °C 2 g (100 % konverze) kopolymerů,1 obsahujícího 5'% molárnich 2-dimethylamlnoethylmethakrylátu, Tento kopolymér je ve vodně alkoholických roztocích nerozpustný,' avěak Je stejně Intenzivně zabarven Jako kopolymery uvedené v příkladech 1 e 2.In the same manner as in Example 1 ae, 1 - 9 g of N-phenylmaleinimide - 0.02 g of 2,2'-azo-bia- (isobutyronltril) and 10 cm 3 of 144 cm @ 3 were prepared at 50 DEG C. C 2 g (100% conversion) of copolymers 1 containing 5% mole of 2-dimethylaminoethyl methacrylate. This copolymer is insoluble in water-alcoholic solutions but is equally intensely colored as the copolymers mentioned in Examples 1 and 2.
Při protřepáni jemně rozpráěkovaného produktu v kyselém prostředí (pH « 4) dochází také k jeho odbarvení. Po zalkalizování se kopolymér zpětně zabarvi do červené barvy.Shaking of the finely sprayed product under acidic conditions (pH «4) also causes discoloration. After alkalization, the copolymer is red-colored.
Syntetizované poly(2-dimethylaminoethylmethakrylát-co-N-fenylmaleinimid)y ee vyznačují výraznou barevnosti v Širokém rozmezí zastoupeni vestavěných komonomerů (5 až 97 % molárnich zabudovaného 2-dlmathylemlnoathylmethakrylátu), Jejich acldobazická barevná přeměna může být využita například při aplikaci těchto kopolymerů jako hydrofilních,' například membránových materiálů. Vratná změna barevnosti v závislosti na pH prostředí,! ee kterým jsou tyto materiály ve styku,' může charakterizovat proces cyklování, tj, převáděni materiálů na bázi kopolymerů 2-dimethylamlnoethylmethakrylátu s N-fanylmalalnimidem do různých iontových forem.Synthesized poly (2-dimethylaminoethyl methacrylate-co-N-phenylmaleinimide) is characterized by a distinctive color range over a wide range of built-in comonomers (5 to 97 mole% of incorporated 2-dimethylamino monoethyl methacrylate), their acldobasic color conversion can be used For example, membrane materials. Reversible color change depending on pH environment! The contacting of these materials can characterize the cycling process, i.e. converting materials based on copolymers of 2-dimethylamino-ethyl methacrylate with N-phanylmalalnimide into various ionic forms.
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS708488A CS273752B1 (en) | 1988-10-26 | 1988-10-26 | Colour copolymers of 2-dimethylaminoethylmetacrylate with n-phenyl-maleatimide and method of their preparation |
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| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CS708488A CS273752B1 (en) | 1988-10-26 | 1988-10-26 | Colour copolymers of 2-dimethylaminoethylmetacrylate with n-phenyl-maleatimide and method of their preparation |
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| Publication Number | Publication Date |
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| CS708488A1 CS708488A1 (en) | 1990-08-14 |
| CS273752B1 true CS273752B1 (en) | 1991-04-11 |
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| CS708488A CS273752B1 (en) | 1988-10-26 | 1988-10-26 | Colour copolymers of 2-dimethylaminoethylmetacrylate with n-phenyl-maleatimide and method of their preparation |
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1988
- 1988-10-26 CS CS708488A patent/CS273752B1/en unknown
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| CS708488A1 (en) | 1990-08-14 |
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