MD4279C1 - Dye for thermoplastic polymers - Google Patents
Dye for thermoplastic polymers Download PDFInfo
- Publication number
- MD4279C1 MD4279C1 MDA20130015A MD20130015A MD4279C1 MD 4279 C1 MD4279 C1 MD 4279C1 MD A20130015 A MDA20130015 A MD A20130015A MD 20130015 A MD20130015 A MD 20130015A MD 4279 C1 MD4279 C1 MD 4279C1
- Authority
- MD
- Moldova
- Prior art keywords
- dye
- thermoplastic polymers
- burgundy
- color
- compound
- Prior art date
Links
- 229920001169 thermoplastic Polymers 0.000 title claims abstract description 9
- 239000011449 brick Substances 0.000 claims abstract description 10
- 239000003086 colorant Substances 0.000 claims description 8
- 239000000975 dye Substances 0.000 abstract description 24
- 150000001875 compounds Chemical class 0.000 abstract description 20
- IBYSTTGVDIFUAY-UHFFFAOYSA-N vanadium monoxide Chemical compound [V]=O IBYSTTGVDIFUAY-UHFFFAOYSA-N 0.000 abstract description 5
- 239000004698 Polyethylene Substances 0.000 description 11
- 239000004793 Polystyrene Substances 0.000 description 11
- -1 polyethylene Polymers 0.000 description 11
- 229920000573 polyethylene Polymers 0.000 description 11
- 229920002223 polystyrene Polymers 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 9
- 238000004040 coloring Methods 0.000 description 6
- 238000000034 method Methods 0.000 description 6
- YRKCREAYFQTBPV-UHFFFAOYSA-N acetylacetone Chemical group CC(=O)CC(C)=O YRKCREAYFQTBPV-UHFFFAOYSA-N 0.000 description 5
- 229920000642 polymer Polymers 0.000 description 5
- JPVYNHNXODAKFH-UHFFFAOYSA-N Cu2+ Chemical compound [Cu+2] JPVYNHNXODAKFH-UHFFFAOYSA-N 0.000 description 3
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 230000015572 biosynthetic process Effects 0.000 description 3
- 239000002184 metal Substances 0.000 description 3
- 229910052751 metal Inorganic materials 0.000 description 3
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 3
- OITQDWKMIPXGFL-UHFFFAOYSA-N 1-hydroxy-2-naphthaldehyde Chemical compound C1=CC=C2C(O)=C(C=O)C=CC2=C1 OITQDWKMIPXGFL-UHFFFAOYSA-N 0.000 description 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 2
- 241000686250 Talaromyces viridulus Species 0.000 description 2
- 125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
- 239000013078 crystal Substances 0.000 description 2
- 230000002538 fungal effect Effects 0.000 description 2
- 150000002739 metals Chemical class 0.000 description 2
- WQUPOMUBXOPGSN-UHFFFAOYSA-N methyl n'-aminocarbamimidothioate Chemical compound CSC(N)=NN WQUPOMUBXOPGSN-UHFFFAOYSA-N 0.000 description 2
- 239000000203 mixture Substances 0.000 description 2
- 125000000018 nitroso group Chemical group N(=O)* 0.000 description 2
- 230000002351 pectolytic effect Effects 0.000 description 2
- 238000012545 processing Methods 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000002028 Biomass Substances 0.000 description 1
- RYGMFSIKBFXOCR-UHFFFAOYSA-N Copper Chemical compound [Cu] RYGMFSIKBFXOCR-UHFFFAOYSA-N 0.000 description 1
- VEQPNABPJHWNSG-UHFFFAOYSA-N Nickel(2+) Chemical compound [Ni+2] VEQPNABPJHWNSG-UHFFFAOYSA-N 0.000 description 1
- 238000009825 accumulation Methods 0.000 description 1
- XLJKHNWPARRRJB-UHFFFAOYSA-N cobalt(2+) Chemical compound [Co+2] XLJKHNWPARRRJB-UHFFFAOYSA-N 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 229910052802 copper Inorganic materials 0.000 description 1
- 239000010949 copper Substances 0.000 description 1
- 238000000354 decomposition reaction Methods 0.000 description 1
- 238000013461 design Methods 0.000 description 1
- 238000011161 development Methods 0.000 description 1
- 125000000664 diazo group Chemical group [N-]=[N+]=[*] 0.000 description 1
- 239000012153 distilled water Substances 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 238000000921 elemental analysis Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002255 enzymatic effect Effects 0.000 description 1
- 235000019441 ethanol Nutrition 0.000 description 1
- 239000008187 granular material Substances 0.000 description 1
- 150000002500 ions Chemical class 0.000 description 1
- 239000003446 ligand Substances 0.000 description 1
- 238000004020 luminiscence type Methods 0.000 description 1
- 238000004949 mass spectrometry Methods 0.000 description 1
- 239000000155 melt Substances 0.000 description 1
- 230000001617 migratory effect Effects 0.000 description 1
- 235000015097 nutrients Nutrition 0.000 description 1
- 150000002894 organic compounds Chemical class 0.000 description 1
- 229920003023 plastic Polymers 0.000 description 1
- 239000004033 plastic Substances 0.000 description 1
- 239000000843 powder Substances 0.000 description 1
- 238000011160 research Methods 0.000 description 1
- 230000004936 stimulating effect Effects 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000725 suspension Substances 0.000 description 1
- 238000003786 synthesis reaction Methods 0.000 description 1
- 125000002813 thiocarbonyl group Chemical group *C(*)=S 0.000 description 1
- 150000003583 thiosemicarbazides Chemical class 0.000 description 1
- 125000005287 vanadyl group Chemical group 0.000 description 1
- UUUGYDOQQLOJQA-UHFFFAOYSA-L vanadyl sulfate Chemical compound [V+2]=O.[O-]S([O-])(=O)=O UUUGYDOQQLOJQA-UHFFFAOYSA-L 0.000 description 1
- 229910000352 vanadyl sulfate Inorganic materials 0.000 description 1
Landscapes
- Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
Abstract
Изобретение относится к органическим красителям, а именно к применению координационного соединения оксованадия(II) в качестве красителя для термопластичных полимеров.Согласно изобретению, заявляется применение 9-(1',2'-нафтил)-4-метил-7-тиометил-5,6,8-триазанон-2,4,6,8-тетраенато(-)-1',2-диолато(-)-O1',O2,N5,N8-ванадил(II) в качестве красителя бордово-кирпичного цвета для термопластичных полимеров.The invention relates to organic dyes, namely the use of the coordination compound oxovanadium (II) as a dye for thermoplastic polymers. According to the invention, the use of 9- (1 ', 2'-naphthyl) -4-methyl-7-thiomethyl-5, 6,8-triazanone-2,4,6,8-tetraenato (-) - 1 ', 2-diolato (-) - O1', O2, N5, N8-vanadyl (II) as a burgundy-brick dye for thermoplastic polymers.
Description
Invenţia se referă la coloranţii organici, şi anume la aplicarea compusului coordinativ al oxovanadiului(II) în calitate de colorant pentru polimerii termoplastici. The invention refers to organic dyes, namely to the application of the coordinating compound of oxovanadium(II) as a dye for thermoplastic polymers.
Este cunoscută utilizarea în calitate de coloranţi pentru masele plastice a compuşilor organici (compuşi ce conţin legături duble conjugate, grupa nitrozo (NO), grupa diazo (-N=N-), carbonil (>C=O), tiocarbonil (>C=S)), anorganici şi mai puţin a compuşilor coordinativi ai metalelor [1]. Coloranţii anorganici posedă o termostabilitate înaltă, însă la colorarea polimerilor ei sunt folosiţi în cantităţi mari şi nu permit obţinerea pieselor transparente. În ceea ce priveşte coloranţii organici, ei trebuie să posede o termostabilitate înaltă (>250°C). It is known to use organic compounds as dyes for plastics (compounds containing conjugated double bonds, nitroso group (NO), diazo group (-N=N-), carbonyl (>C=O), thiocarbonyl (>C= S)), inorganic and less of the coordination compounds of metals [1]. Inorganic dyes have a high thermostability, but when coloring polymers, they are used in large quantities and do not allow obtaining transparent parts. As far as organic dyes are concerned, they must have a high thermostability (>250°C).
Obţinerea coloranţilor termostabili la temperaturi necesare proceselor tehnologice cu o înaltă fotostabilitate şi consum mic pentru o intensitate pronunţată şi diferite nuanţe a culorii rămâne o problemă actuală. Obtaining thermostable dyes at temperatures necessary for technological processes with high photostability and low consumption for pronounced intensity and different shades of color remains a current problem.
În calitate de cea mai apropiată soluţie serveşte compusul complex al cuprului(II) cu formula: As the closest solution serves the complex compound of copper(II) with the formula:
care colorează polistirenul şi polietilena în culoarea bordo cu nuanţă galbenă [2]. which colors polystyrene and polyethylene in a burgundy color with a yellow tint [2].
Dezavantajul acestui colorant constă în aceea că se descompune la temperatura de 260°C. The disadvantage of this dye is that it decomposes at a temperature of 260°C.
Studiul proprietăţilor coloristice ale şirului de compuşi coordinativi cu formula sus-menţionată, care se deosebesc numai prin prezenţa diferitor metale, a stabilit că asupra nuanţei culorii în mare măsură influenţează atomul metalului şi mai puţin radicalul fragmentului acetilacetonic, şi anume: nichelul(II) colorează polistirenul şi polietilena în culoarea bordo (MD 2881 F1 2005.10.31), cobaltul(II) - în verzuie cu nuanţă galbenă (MD 3431 F1 2007.11.30), cuprul(II) - în bordo cu nuanţă galbenă. The study of the color properties of the series of coordinating compounds with the above-mentioned formula, which differ only by the presence of different metals, established that the color shade is largely influenced by the metal atom and less by the radical of the acetylacetone fragment, namely: nickel(II) colors polystyrene and polyethylene in burgundy color (MD 2881 F1 2005.10.31), cobalt(II) - in green with a yellow shade (MD 3431 F1 2007.11.30), copper(II) - in burgundy with a yellow shade.
Pentru a lărgi gama de culori s-au studiat proprietăţile coloristice ale altor compuşi de acest tip. In order to widen the range of colors, the color properties of other compounds of this type were studied.
Problema pe care o rezolvă invenţia constă în elaborarea unui nou colorant, care colorează polimerii termoplastici în bordo-cărămiziu şi posedă o înaltă fotostabilitate (7 puncte) în ton complet, termostabilitate (285°C) şi consum mic (0,006…0,010 g la 100 g polistiren şi 0,005…0,015 g la 100 g polietilenă). The problem that the invention solves is the development of a new dye, which colors thermoplastic polymers in burgundy-brick and possesses high photostability (7 points) in full tone, thermostability (285°C) and low consumption (0.006...0.010 g per 100 g polystyrene and 0.005...0.015 g per 100 g polyethylene).
Problema se rezolvă prin aceea că se propune aplicarea a 9-(1',2'-naftil)-4-metil-7-tiometil-5,6,8-triazanona-2,4,6,8-tetraenato(-)-1',2-diolato(-)-O1',O2,N5,N8-vanadil(II) cu formula: The problem is solved by proposing the application of 9-(1',2'-naphthyl)-4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenato(-) -1',2-diolato(-)-O1',O2,N5,N8-vanadyl(II) with the formula:
în calitate de colorant de culoare bordo-cărămizie pentru polimerii termoplastici. as a burgundy-brick colorant for thermoplastic polymers.
Proprietăţile coloristice ale compusului 9-(1',2'-naftil)-4-metil-7-tiometil-5,6,8-triazanona-2,4,6,8-tetraenato(-)-1',2-diolato(-)-O1',O2,N5,N8-vanadil(II), anterior sintetizat în baza S-metilizotiosemicarbazonei acetilacetonei şi 1-hidroxi-2-naftaldehidei, au fost supuse cercetării pentru aplicare în polimerii termoplastici. Color properties of the compound 9-(1',2'-naphthyl)-4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenato(-)-1',2- diolato(-)-O1',O2,N5,N8-vanadyl(II), previously synthesized based on S-methylisothiosemicarbazone of acetylacetone and 1-hydroxy-2-naphthaldehyde, were subjected to research for application in thermoplastic polymers.
Metoda de obţinere a compusului The method of obtaining the compound
La soluţia formată din 1 mmol (0,32 g) de S-metilizotiosemicarbazonă a acetilacetonei în 25 ml metanol se adaugă 1 mmol (0,17 g) 1-hidroxi-2-naftaldehidă în 25 ml metanol, 5 ml trietilamină şi 0,22 g VOSO4·3H2O dizolvate în 5 ml apă distilată. Conţinutul balonului se refluxează pe baia de apă până cad cristale. După răcire cristalele aciforme de culoare brună se filtrează, se spală cu metanol şi eter dietilic. Se obţin 0,33 g. Randament 47,4 %. Compusul reprezintă un praf de culoare cafenie-închisă, insolubil în apă, alcool etilic, solubil în cloroform, dimetilsulfoxid, stabil în condiţii obişnuite, se topeşte fără descompunere. To the solution consisting of 1 mmol (0.32 g) of S-methylisothiosemicarbazone of acetylacetone in 25 ml of methanol is added 1 mmol (0.17 g) of 1-hydroxy-2-naphthaldehyde in 25 ml of methanol, 5 ml of triethylamine and 0. 22 g of VOSO4·3H2O dissolved in 5 ml of distilled water. The contents of the flask are refluxed on the water bath until crystals fall out. After cooling, the aciform brown crystals are filtered, washed with methanol and diethyl ether. 0.33 g are obtained. Yield 47.4%. The compound is a dark brown powder, insoluble in water, ethyl alcohol, soluble in chloroform, dimethylsulfoxide, stable under normal conditions, melts without decomposition.
Compoziţia şi structura complexului (C18H17N3O2SVO) au fost confirmate cu ajutorul metodelor tradiţionale RMN (1H, 13C), IR, UV-Vis, analiza elementală, mas-spectrometria. S-a stabilit că coordinarea ionului de vanadil(II), ca şi în cazul compusului coordinativ al cuprului, se efectuează prin atomii O1', O2, N5, N8. The composition and structure of the complex (C18H17N3O2SVO) were confirmed using traditional NMR (1H, 13C), IR, UV-Vis, elemental analysis, mass spectrometry methods. It was established that the coordination of the vanadyl(II) ion, as in the case of the coordination compound of copper, is carried out by the atoms O1', O2, N5, N8.
A fost studiată influenţa acestui compus asupra procesului de biosinteză a enzimelor pectolitice de către tulpina fungică Penicillium viride. S-a stabilit că, în dependenţă de concentraţia în mediul nutritiv, compusul complex manifestă proprietăţi de stimulare (acumularea biomasei, sporirea activităţii enzimatice şi fermentative), stabilizează procesele de biosinteză a enzimelor pectolitice de către tulpina fungică Penicillium viride în condiţii nefavorabile (Cocu M., Gradinaru J., Revenco M., Rîbak-Akimova E., Gărbălău N. Design and synthesis of coordination compounds with tetradentate ligands derived from alkylated thiosemicarbazide. Chemistry Journal of Moldova. General, Industrial and Ecological Chemistry, 2008, 3(2), p. 38-46). The influence of this compound on the process of biosynthesis of pectolytic enzymes by the fungal strain Penicillium viride was studied. It was established that, depending on the concentration in the nutrient medium, the complex compound exhibits stimulating properties (accumulation of biomass, increased enzymatic and fermentative activity), stabilizes the processes of biosynthesis of pectolytic enzymes by the fungal strain Penicillium viride in unfavorable conditions (Cocu M., Gradinaru J., Revenco M., Rîbak-Akimova E., Gărbălău N. Design and synthesis of coordination compounds with tetradentate ligands derived from alkylated thiosemicarbazide. Chemistry Journal of Moldova. General, Industrial and Ecological Chemistry, 2008, 3(2), pp. 38-46).
Polietilena şi polistirenul coloraţi cu compusul coordinativ al oxovanadiului posedă aceleaşi proprietăţi ca şi compusul conform celei mai apropiate soluţii: sunt stabili la prelucrări fizico-mecanice, au stabilitate termică, luminiscenţă migraţională şi datorită adeziunii la polistiren nu sunt necesare substanţe suplimentare pentru prelucrarea granulelor, dar se deosebeşte prin nuanţa culorii polimerului şi prin aceea că compusul coordinativ al oxovanadiului are o termostabilitate mai înaltă cu 25°C. Polyethylene and polystyrene colored with the coordination compound of oxovanadium possess the same properties as the compound according to the closest solution: they are stable to physical-mechanical processing, they have thermal stability, migratory luminescence and due to the adhesion to polystyrene, no additional substances are needed for the processing of the granules, but it is distinguished by the shade of the color of the polymer and by the fact that the coordinating compound of oxovanadium has a higher thermostability by 25°C.
Dacă în aceleaşi condiţii luate pentru o vizibilă comparare, compusul coordinativ al cuprului(II) colorează polistirenul şi polietilena în culoarea bordo cu nuanţă galbenă, atunci compusul coordinativ al oxovanadiului(II) colorează aceiaşi polimeri în culoare bordo-cărămizie. If under the same conditions taken for a visible comparison, the coordinating compound of copper(II) colors polystyrene and polyethylene in a burgundy color with a yellow hue, then the coordinating compound of oxovanadium(II) colors the same polymers in a burgundy-brick color.
La utilizarea compusului propus pentru colorarea polimerilor termoplastici au fost obţinute piese de culoare bordo-cărămizie. În dependenţă de concentraţia colorantului au fost obţinute articole colorate uniform cu diferită intensitate a culorii. When using the proposed compound for coloring thermoplastic polymers, burgundy-brick colored pieces were obtained. Depending on the dye concentration, uniformly colored items with different color intensity were obtained.
Testarea colorantului a fost realizată în condiţii de laborator, iar rezultatele obţinute sunt prezentate în tabel. The dye was tested in laboratory conditions, and the results obtained are presented in the table.
Tabel Table
Caracteristica colorantului şi a analogului proxim Characteristic of the dye and the close analogue
Colorantul Termostabilitatea,ºC Stabilitatea la lumină, puncte Culoarea polistirenului* Culoarea polietilenei* Uniformitatea colorării* Consumul coloranţilor, g/100 g polimer Polistiren Polietilenă De tip Bloc De emulsie, de suspensie Densitate înaltă Densitate joasă Ton mijlociu Ton intens Ton mijlociu Ton intens Ton mijlociu Ton intens Ton mijlociu Ton intens I 260 7 Bordo cu nuanţă galbenă Bordo cu nuanţă galbenă Uniformă 0,006 - 0,010 0,050 - 0,100 0,010 - 0,015 0,020 - 0,080 0,005 - 0,010 0,015 - 0,035 0,008 - 0,010 0,015 - 0,035 II 285 Bordo-cărămiziu Bordo-cărămiziu Dye Thermostability, ºC Light stability, points Color of polystyrene* Color of polyethylene* Uniformity of coloring* Consumption of dyes, g/100 g polymer Polystyrene Polyethylene Block type Emulsion, suspension High density Low density Medium tone Intense tone Medium tone Intense tone Medium tone Intense tone Medium tone Intense tone I 260 7 Bordeaux with yellow shade Bordeaux with yellow shade Uniform 0.006 - 0.010 0.050 - 0.100 0.010 - 0.015 0.020 - 0.080 0.005 - 0.010 0.015 - 0.035 0.008 - 0.010 0, 015 - 0.035 II 285 Burgundy-brick Burgundy-brick
I - colorantul conform celei mai apropiate soluţii I - the dye according to the closest solution
II - colorantul conform invenţiei. II - the dye according to the invention.
*Culoarea şi uniformitatea colorării pieselor a fost apreciată vizual. *The color and uniformity of the coloring of the pieces was visually appreciated.
Exemple de realizare a invenţiei Examples of realization of the invention
Exemplul 1 Example 1
Colorarea polistirenului. Polistirenul granulat se amestecă în prealabil cu colorant într-un reactor dotat cu termometru, agitator şi robinet pentru a fuziona în formă. Amestecul se încălzeşte la agitare până la topirea componentelor, apoi se fuzionează în forma necesară. Polystyrene coloring. Granulated polystyrene is pre-mixed with dye in a reactor equipped with thermometer, stirrer and tap to fuse into shape. The mixture is heated with stirring until the components melt, then it is fused in the required form.
La dozarea a 0,006...0,010 părţi de masă a colorantului cu 100 părţi de masă a polistirenului se obţin piese transparente de culoare bordo-cărămizie, uniform vopsite, iar la folosirea a 0,05...0,15 părţi de masă a colorantului la 100 părţi de masă a polimerului se obţin piese cu nuanţă deplină. When dosing 0.006...0.010 parts by mass of the dye with 100 parts by mass of polystyrene, transparent pieces of burgundy-brick color, uniformly painted, are obtained, and when using 0.05...0.15 parts by mass of of the dye to 100 parts by mass of the polymer, parts with a full shade are obtained.
Exemplul 2 Example 2
Colorarea polietilenei. Polietilena granulată cu o densitate mică sau mare se amestecă cu colorant şi se prelucrează conform procedeului menţionat mai sus. Polyethylene coloring. Granulated polyethylene with a low or high density is mixed with dye and processed according to the process mentioned above.
La dozarea a 0,005...0,015 părţi de masă a colorantului cu 100 părţi de masă a polietilenei se obţin piese transparente de culoare bordo-cărămizie, tonul deplin se obţine la dozarea a 0,015...0,035 părţi de masă a colorantului la 100 părţi de masă de polietilenă. When dosing 0.005...0.015 parts by mass of the dye with 100 parts by mass of polyethylene, transparent pieces of burgundy-brick color are obtained, the full tone is obtained when dosing 0.015...0.035 parts by mass of the dye per 100 parts of polyethylene table.
1. Гордон П., Грегори П. Органическая химия красителей. Москва, Мир, 1986, p. 158 1. Гордон П., Грегори П. Organic chemicals. Moscow, Mir, 1986, p. 158
2. MD 3915 F1 2009.05.31 2. MD 3915 F1 2009.05.31
Claims (1)
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20130015A MD4279C1 (en) | 2013-01-17 | 2013-01-17 | Dye for thermoplastic polymers |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| MDA20130015A MD4279C1 (en) | 2013-01-17 | 2013-01-17 | Dye for thermoplastic polymers |
Publications (2)
| Publication Number | Publication Date |
|---|---|
| MD4279B1 MD4279B1 (en) | 2014-03-31 |
| MD4279C1 true MD4279C1 (en) | 2014-10-31 |
Family
ID=50685393
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| MDA20130015A MD4279C1 (en) | 2013-01-17 | 2013-01-17 | Dye for thermoplastic polymers |
Country Status (1)
| Country | Link |
|---|---|
| MD (1) | MD4279C1 (en) |
Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1040034A (en) * | 1963-09-06 | 1966-08-24 | Ciba Ltd | Heterocyclic water-insoluble monoazo dyestuffs and a process for their manufacture |
| SU472957A1 (en) * | 1973-06-25 | 1975-06-05 | Предприятие П/Я А-7850 | The method of obtaining the complex metal-containing azo pigment |
| US4612014A (en) * | 1982-03-09 | 1986-09-16 | Ciba-Geigy Corporation | Use of metal complexes of hydrazones as pigments |
| US4670486A (en) * | 1984-06-15 | 1987-06-02 | Ciba-Geigy Corporation | Polymer composition pigmented with copper or nickel complexes of ligands containing a semicarbazone moiety |
| EP0349489A2 (en) * | 1988-07-01 | 1990-01-03 | Ciba-Geigy Ag | Organic macromolecular material containing a hydrazone-based metal complex pigment |
| WO1999012929A2 (en) * | 1997-09-12 | 1999-03-18 | Hoffman/Barrett, L.L.C. | Heteroatom-functionalized porphyrazines and multimetallic complexes and polymers derived therefrom |
| MD1206F1 (en) * | 1998-08-11 | 1999-04-30 | Inst De Chimie Al Academiei De | 2,2-Difluor-9-alkylthio-5,6-di(a-furyl)-12-methyl-1,3-dioxa-4,7,8,10,11,14-hexaaza-2-boracyclotetradeca-4,6,8,11,13-penta-enato-N4,N7,N10,N14-nickel(II) as colorants for plastics |
| WO1999033435A1 (en) * | 1997-12-23 | 1999-07-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of transitional metal complexes for dying keratin fibers |
| RU2188200C2 (en) * | 2000-10-04 | 2002-08-27 | Государственный научный центр Российской Федерации "НИОПИК" | β, β, β′, β′-TETRAMETHYLTRIARENOTETRAAZACHLORINES AND METHODS OF THEIR SYNTHESIS |
| MD2881F1 (en) * | 2005-04-15 | 2005-10-31 | Institutul De Chimie Al Academiei De Stiinte A Republicii Moldova | Triazamacrocyclic complex compounds of nickel(II) and their application as colorant for thermoplastic polymers |
| MD3431F1 (en) * | 2007-02-21 | 2007-11-30 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | 9- (2'-naphthyl) -4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenate-1 ', 2-diolate (-2) -O1', O2 , N5, N8-cobalt (II) and its use as a dye for thermoplastic polymers (57MO) The invention relates to a new coordinating compound, in particular to a complex of cobalt (II), which can be used for coloring plastics. The essence of the invention is that a coordinating compound of cobalt (II), namely, 9- (2'-naphthyl) -4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6, is synthesized. , 8-tetraenato-1 ', 2-diolato (-2) -O1', O2, N5, N8-cobalt (II) through the interaction of acetylacetone S-methylisothiosemicarbazone with 1-hydroxy-2-naphthaldehyde, which can be used in dye quality for thermoplastic polymers. |
| US20080015356A1 (en) * | 2004-10-01 | 2008-01-17 | Yoshihisa Kakuta | Binuclear Metal Complex, Metal Complex Dye, Photoelectric Conversion Element, and Photochemical Battery |
| MD3915F1 (en) * | 2008-05-19 | 2009-05-31 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | Use of 9-(1',2'-naphthyl)-4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenato(-)-1',2-diolato(-)-O1',O2,N5,N8-copper(II) as colorant for thermoplastic polymers |
-
2013
- 2013-01-17 MD MDA20130015A patent/MD4279C1/en not_active IP Right Cessation
Patent Citations (13)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB1040034A (en) * | 1963-09-06 | 1966-08-24 | Ciba Ltd | Heterocyclic water-insoluble monoazo dyestuffs and a process for their manufacture |
| SU472957A1 (en) * | 1973-06-25 | 1975-06-05 | Предприятие П/Я А-7850 | The method of obtaining the complex metal-containing azo pigment |
| US4612014A (en) * | 1982-03-09 | 1986-09-16 | Ciba-Geigy Corporation | Use of metal complexes of hydrazones as pigments |
| US4670486A (en) * | 1984-06-15 | 1987-06-02 | Ciba-Geigy Corporation | Polymer composition pigmented with copper or nickel complexes of ligands containing a semicarbazone moiety |
| EP0349489A2 (en) * | 1988-07-01 | 1990-01-03 | Ciba-Geigy Ag | Organic macromolecular material containing a hydrazone-based metal complex pigment |
| WO1999012929A2 (en) * | 1997-09-12 | 1999-03-18 | Hoffman/Barrett, L.L.C. | Heteroatom-functionalized porphyrazines and multimetallic complexes and polymers derived therefrom |
| WO1999033435A1 (en) * | 1997-12-23 | 1999-07-08 | Henkel Kommanditgesellschaft Auf Aktien | Use of transitional metal complexes for dying keratin fibers |
| MD1206F1 (en) * | 1998-08-11 | 1999-04-30 | Inst De Chimie Al Academiei De | 2,2-Difluor-9-alkylthio-5,6-di(a-furyl)-12-methyl-1,3-dioxa-4,7,8,10,11,14-hexaaza-2-boracyclotetradeca-4,6,8,11,13-penta-enato-N4,N7,N10,N14-nickel(II) as colorants for plastics |
| RU2188200C2 (en) * | 2000-10-04 | 2002-08-27 | Государственный научный центр Российской Федерации "НИОПИК" | β, β, β′, β′-TETRAMETHYLTRIARENOTETRAAZACHLORINES AND METHODS OF THEIR SYNTHESIS |
| US20080015356A1 (en) * | 2004-10-01 | 2008-01-17 | Yoshihisa Kakuta | Binuclear Metal Complex, Metal Complex Dye, Photoelectric Conversion Element, and Photochemical Battery |
| MD2881F1 (en) * | 2005-04-15 | 2005-10-31 | Institutul De Chimie Al Academiei De Stiinte A Republicii Moldova | Triazamacrocyclic complex compounds of nickel(II) and their application as colorant for thermoplastic polymers |
| MD3431F1 (en) * | 2007-02-21 | 2007-11-30 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | 9- (2'-naphthyl) -4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenate-1 ', 2-diolate (-2) -O1', O2 , N5, N8-cobalt (II) and its use as a dye for thermoplastic polymers (57MO) The invention relates to a new coordinating compound, in particular to a complex of cobalt (II), which can be used for coloring plastics. The essence of the invention is that a coordinating compound of cobalt (II), namely, 9- (2'-naphthyl) -4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6, is synthesized. , 8-tetraenato-1 ', 2-diolato (-2) -O1', O2, N5, N8-cobalt (II) through the interaction of acetylacetone S-methylisothiosemicarbazone with 1-hydroxy-2-naphthaldehyde, which can be used in dye quality for thermoplastic polymers. |
| MD3915F1 (en) * | 2008-05-19 | 2009-05-31 | Institutul De Chimie Al Academiei De Stiinte A Moldovei | Use of 9-(1',2'-naphthyl)-4-methyl-7-thiomethyl-5,6,8-triazanone-2,4,6,8-tetraenato(-)-1',2-diolato(-)-O1',O2,N5,N8-copper(II) as colorant for thermoplastic polymers |
Non-Patent Citations (1)
| Title |
|---|
| Гордон П., Грегори П. Органическая химия красителей. Москва, Мир, 1986, p. 158 * |
Also Published As
| Publication number | Publication date |
|---|---|
| MD4279B1 (en) | 2014-03-31 |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| Patil et al. | DNA cleavage, antimicrobial, spectroscopic and fluorescence studies of Co (II), Ni (II) and Cu (II) complexes with SNO donor coumarin Schiff bases | |
| Hasan et al. | Nickel complexes of Schiff bases derived from mono/diketone with anthranilic acid: Synthesis, characterization and microbial evaluation | |
| Levín et al. | Water-mediated reduction of [Cu (dmp) 2 (CH 3 CN)] 2+: implications of the structure of a classical complex on its activity as an anticancer drug | |
| İnan et al. | Half-sandwich Ruthenium (II) arene complexes bearing the azo-azomethine ligands: Electrochemical, computational, antiproliferative and antioxidant properties | |
| Tocher et al. | Areneruthenium (II) carboxylates: reactions with ligands and the X-ray structure of the p-cymene pyrazine complex [Ru (η-p-MeC 6 H 4 CHMe 2) Cl (pyz) 2] PF 6 | |
| Yan et al. | Novel quadridentate salen type triple-decker sandwich ytterbium complexes with near infrared luminescence | |
| Booth et al. | Platinum carbonyls substituted by tertiary phosphines | |
| Klein | Synthesis, Spectroscopic Properties, and Crystal Structure of 2, 2′‐Bipyridyldimesitylnickel (II) | |
| US4065481A (en) | 1:1-Azomethine-metal-complex dyestuffs | |
| MD4279C1 (en) | Dye for thermoplastic polymers | |
| Ahmed et al. | Synthesis, spectroscopic and electrochemical characterisation of binuclear dioxomolybdenum complexes derived from disalicylaldehyde succinoyldihydrazone | |
| Kolawole et al. | Synthesis and characterization of some metal (II) complexes of isomeric unsymmetrical Schiff bases and their adducts with triphenylphosphine | |
| Ghosh et al. | Structural, spectroscopic and redox properties of transition metal complexes of dipyrido [3, 2-f: 2′, 3′-h]-quinoxaline (dpq) | |
| Hadi | Coordination Behavior of N/O donor ligand with some transition metals | |
| Mahmoud et al. | Preparation and spectral characterization of new azo imidazole ligand 2-[(2-cyano phenyl) Azo]-4, 5-Diphenyl imidazole and its complexes with Co (II), Ni (II), Cu (II), Zn (II), Cd (II) and Hg (II) ions | |
| Thakar et al. | Synthesis, Characterization and Antibacterial Activity of Novel Schiff Bases Derived from 4‐Phenyl‐2‐aminothiazole and their Mn (II), Fe (II), Co (II), Ni (II) and Cu (II) Metal complexes | |
| Biju et al. | Synthesis, spectral and single crystal X-ray characterization of 5-(2-(2, 3-dimethyl-5-oxo-1-phenyl-2, 5-dihydro-1H-pyrazol-4-yl) hydrazono) pyrimidine-2, 4, 6 (1H, 3H, 5H)-trione and its copper (II) complexes | |
| MD4328C1 (en) | Dye for thermoplastic polymers | |
| Shrestha et al. | Synthesis and characterization of copper complex of salicylaldehyde benzoyl hydrazone | |
| Roy et al. | Luminescent rhenium (I) carbonyl complex with redox noninnocent ONS donor azo-phenol ligand: Synthesis, X-ray structure, photophysical properties and live cell imaging | |
| Habiban et al. | Preparation and Characterization of Some Metal Complexes with Heterocyclic Azo Ligand (4-SuBAI) | |
| El-Sonbati et al. | Supramolecular structure, stereochemistry and substituents effect on the spectral studies of novel ruthenium complexes | |
| Verma et al. | CHAPTER: 4 SYNTHESIS AND CHARACTERIZATION OF SOME MIXED LIGAND COMPLEXES OF NICKEL (II) FORMED WITH 1-METHOXY CARBONYL–1-CYANO ETHYLENE-2, 2-DITHIOLATE LIGAND AND NITROGEN DONORS | |
| Wu et al. | Zinc (II) and Co (II) complexes based on bis (N-allylbenzimidazol-2-ylmethyl) aniline: Synthesis, crystal structures and antioxidative activity | |
| Al-Jeboori et al. | Synthesis and characterization of polydentate ligand and its metal complexes |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| FG4A | Patent for invention issued | ||
| KA4A | Patent for invention lapsed due to non-payment of fees (with right of restoration) | ||
| MM4A | Patent for invention definitely lapsed due to non-payment of fees |