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Benzothiazol-2-ylazo-phenyl compound as dye, compositions including the dye, and method of determining degree of cure of such compositions

A kind of technology of compound, composition, be used in benzothiazol-2-ylazo-phenyl compound as dyestuff

Active Publication Date: 2016-03-30
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

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Problems solved by technology

These methods require equipment and may require interruption of the process since many of these methods cannot be performed while the manufacturing process is taking place
In addition, many of the analytical methods described require a skilled user who can interpret the results

Method used

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  • Benzothiazol-2-ylazo-phenyl compound as dye, compositions including the dye, and method of determining degree of cure of such compositions
  • Benzothiazol-2-ylazo-phenyl compound as dye, compositions including the dye, and method of determining degree of cure of such compositions
  • Benzothiazol-2-ylazo-phenyl compound as dye, compositions including the dye, and method of determining degree of cure of such compositions

Examples

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example

[0097] Reagent .

[0098] Vinyldimethylazlactone is commercially available from IsoChemSAS, Evry, France (IsoChem S.A.S., Evry, France). All other reagents were obtained or are commercially available from fine chemical suppliers such as: Sigma-Aldrich Company, St. Louis, Missouri; EMD Millipore Chemicals, Billerica, Mass. (EMDMillipore Chemicals, Billerica, Massachusetts); Alfa Aesar, Ward Hill, Massachusetts; J.T. Baker, Phillipsburg, New Jersey; Dorset, UK BDH Merck Ltd., Poole, Dorset, Uk, and Cambridge Isotope Laboratories, Inc., Andover, Massachusetts, or may be synthesized by known methods. All ratios are by weight unless otherwise reported.

[0099] The following abbreviations are used to describe instances:

[0100] ℃: degrees Celsius

[0101] cm: centimeter

[0102] CDCl 3 : deuterated chloroform

[0103] d 6 -DMSO: deuterated dimethyl sulfoxide

[0104] mg: milligram

[0105] mil: 10 -3 inch

[0106] mL: milliliter

[0107] mm: mm

[0108] mmol: milli...

example 1

[0117] Synthesis of 2-{(2-cyano-ethyl)-[4-(6-nitro-benzothiazol-2-ylazo)-phenyl]-amino}-ethyl 2-methacrylic acid ester :

[0118]

[0119] At about 21°C, 0.29 mL (2.1 mmol) of triethylamine was added to a 50 mL flask containing 0.55 g (1.39 mmol) of 3-{(2-hydroxy-ethyl)-[4-6-nitrate yl-benzothiazol-2-ylazo)-phenyl]-amino}-propionitrile in 20 mL of tetrahydrofuran, which was then cooled to 0°C. Then 162 μL (1.67 mmol) of methacryloyl chloride was added, and the mixture was stirred under a nitrogen atmosphere for 16 hours while maintaining the temperature at 0°C. The reaction mixture was filtered, and the filtrate was concentrated on a rotary evaporator. The resulting purple substance was dissolved in chloroform, washed twice with saturated sodium carbonate solution, twice with deionized water, and once with saturated sodium chloride solution. The organic portion was then dried over a bed of anhydrous sodium sulfate, filtered and concentrated on a rotary evaporator. The r...

example 2

[0121] Synthesis of 2-{(2-cyano-ethyl)-[4-(6-nitro-benzothiazol-2-ylazo)-phenyl]-amino}-ethyl acrylate:

[0122]

[0123] At about 21°C, 422 μL (3.03 mmol) of triethylamine was added to a 100 mL flask containing 0.399 g (1.01 mmol) of 3-{(2-hydroxyl-ethyl)-[4-(6- A solution of nitro-benzothiazol-2-ylazo)-phenyl]-amino}-propionitrile in 20 mL of N,N-dimethylformamide. This solution was stirred at about 21 °C for 10 minutes under nitrogen atmosphere. Then 195 μL (2.41 mmol) of acryloyl chloride was added. The flask was placed in an oil bath, and the mixture was stirred under a nitrogen atmosphere for 18 hours while maintaining the temperature at about 70°C. The reaction mixture was then partitioned between water (about 50 mL) and dichloromethane (about 50 mL). The aqueous layer was made basic by adding 5 mL of saturated aqueous sodium bicarbonate. The organic layer was then removed, and the aqueous layer was extracted twice more with dichloromethane (about 50 mL each). T...

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Abstract

A compound represented by formula: is disclosed. R is hydrogen or alkyl; X is alkylene; Y is a bond, ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, thiourea, alkylene, arylalkylene, alkylarylene, or arylene, wherein alkylene, arylalkylene, alkylarylene, and arylene are optionally at least one of interrupted or terminated by at least one of an ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea, or thiourea; and Z is an acrylate, a methacrylate, an acrylamide, a methacrylamide, a styrenyl, or a terminal alkenylene having at least three carbon atoms. A composition including the compound, and a method of determining the degree of cure of a curable polymeric resin are also disclosed.

Description

[0001] Cross References to Related Applications [0002] This application claims priority to US Provisional Application 61 / 793,001, filed March 15, 2013, the disclosure of which is incorporated herein by reference in its entirety. Background technique [0003] Inclusion of a dye in the curing agent or catalyst composition may be useful, for example, when the curing agent or catalyst must be mixed with the curable resin prior to placing and curing the resin. Dyes may be useful, for example, to indicate cure or the catalyst is uniformly mixed with the curable resin. Peroxide and dye formulations are also known in which the color disappears when the peroxide is used to generate free radicals during curing of the curable resin. See, eg, Japanese Patent Application Publication SHO59-120612 published Jul. 21, 1984, and US Patent Application Publication 2006 / 0202158 (Chen et al.). While many methods exist to determine the degree of cure in a curing system, most methods require tak...

Claims

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Application Information

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IPC IPC(8): C07D277/82C09B29/033
CPCC07D277/82C09B43/263C09B43/28C09B69/106G01N33/442C09B29/0088C08K3/22C08K3/26C08K3/34C08K3/346C08K3/38C08K2003/2227C08K2003/2244C08K2003/265C08K2003/267C08K2003/387C08L33/04C08L41/00C09B29/00
Inventor 迈克尔·S·文德兰马克·F·舒尔茨凯瑟琳·S·谢弗乔治·W·格里斯格拉伯
Owner 3M INNOVATIVE PROPERTIES CO
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