Benzothiazol-2-ylazo-phenyl compounds as dyes, compositions comprising same, and method for determining the 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: 2019-03-12
3M INNOVATIVE PROPERTIES CO
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  • Summary
  • Abstract
  • Description
  • Claims
  • Application Information

AI Technical Summary

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 compounds as dyes, compositions comprising same, and method for determining the degree of cure of such compositions
  • Benzothiazol-2-ylazo-phenyl compounds as dyes, compositions comprising same, and method for determining the degree of cure of such compositions
  • Benzothiazol-2-ylazo-phenyl compounds as dyes, compositions comprising same, and method for determining the degree of cure of such compositions

Examples

Experimental program
Comparison scheme
Effect test

example

[0097] Reagent .

[0098] Vinyldimethylazlactone is commercially available from 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, MA; EMD Millipore Chemicals, Billerica, Massachusetts; Alfa Aesar, Ward Hill, Massachusetts; J.T. Baker, Phillipsburg, New Jersey Jersey); BDH Merck Ltd., Poole, Dorset, UK, and Cambridge Isotope Laboratories, Inc., Andover, Massachusetts ; or can be synthesized by known methods. All ratios are by weight unless otherwise reported.

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

[0100] ℃: Celsius

[0101] cm: cm

[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: millimole

[0109] μL: microliter

[0110] μmol: m...

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

The invention discloses a compound represented by the following formula: R is hydrogen or alkyl; X is alkylene; Y is bond, ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonic acid Ester, carbamate, thiocarbamate, urea, thiourea, alkylene, arylalkylene, alkylarylene, or arylene, wherein alkylene, arylalkylene , alkylarylene, and arylene are optionally replaced by ether, thioether, amine, amide, ester, thioester, carbonate, thiocarbonate, carbamate, thiocarbamate, urea , or at least one of thiourea for at least one of insertion or termination; and Z is acrylate, methacrylate, acrylamide, methacrylamide, styryl, or a compound having at least three carbon atoms terminal alkenyl. Compositions comprising the compounds, and methods of determining the degree of cure of curable polymeric resins 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 SHO 59-120612 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 ta...

Claims

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Application Information

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Patent Type & Authority Patents(China)
IPC IPC(8): C07D277/82C09B29/033
CPCG01N33/442C07D277/82C08K3/22C08K3/26C08K3/34C08K3/346C08K3/38C08K2003/2227C08K2003/2244C08K2003/265C08K2003/267C08K2003/387C08L33/04C08L41/00C09B29/00C09B29/0088C09B43/263C09B43/28C09B69/106
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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