The analysis of polymeric 2,2,4‐trimethyl‐1,2‐dihydroquinoline

Smejkal, F; Čihová, Alena; Popl, M.; Novák, Jaromír

doi:10.1002/apmc.1980.050880111

Cited by 4 publications

(3 citation statements)

References 7 publications

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“…The aromatic rings presumably are stable because of resonance. The main degradation products of TMQ determined in the literature [29] are as follows: p,p′-diamino-2,2-diphenylpropane, methyl, and small quantities of aniline, whose chemical structures contain groups that can be related to the absorptions observed in the TMQ spectrum (Figure 2a). Figure 2b shows the FT-IR spectrum of the gaseous pyrolysis products of sulfur compounds.…”

Section: Infrared Analysis Of Additivesmentioning

confidence: 99%

Characterization of Additives Typically Employed in EPDM Formulations by using FT-IR of Gaseous Pyrolyzates

Sanches¹,

Cassu²,

Diniz³

et al. 2014

Polímeros

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Abstract:In this study, Fourier transform infrared spectroscopy (FT-IR) was employed to investigate the gaseous pyrolysis products of ethylene-propylene-diene rubber (EPDM). The objective was to evaluate the potential of FT-IR analysis of gaseous pyrolyzates (PY-G/FT-IR) for characterization of EPDM additives. Two EPDM formulations, containing additives typically employed in EPDM rubbers, were analyzed. Initially, gaseous pyrolysis products from paraffin oil, stearic acid, 2,2,4-trimethyl-1,2-dihydroquinoline, tetramethylthiuram monosulfide (TMTM), tetramethylthiuram disulfide (TMTD), and 2-mercaptobenzothiazole (MBT) were characterized separately, and their main absorptions were identified. Subsequently, the gaseous pyrolysis products of raw, unvulcanized, and vulcanized EPDM formulations were analyzed. The similarities observed in the FT-IR spectra of unvulcanized and vulcanized EPDM show that the vulcanization process does not interfere with the pyrolysis products. The identification of the functional groups of the studied additives was possible in both unvulcanized and vulcanized EPDM samples, without solvent extraction. Results also demonstrate that the PY-G/FT-IR technique can identify additives containing sulfur in concentrations as low as 1.4 phr (1.26%) in both unvulcanized and vulcanized EPDM. However, the method showed some limitation due to overlapping and to similarities of TMTM and TMTD PY-G/FT-IR spectra, which could not be distinguished from each other. The PY-G/FT-IR technique is a faster and cheaper alternative to the sophisticated techniques usually applied to detection of additives in rubbers.

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Section: Infrared Analysis Of Additivesmentioning

confidence: 99%

Characterization of Additives Typically Employed in EPDM Formulations by using FT-IR of Gaseous Pyrolyzates

Sanches¹,

Cassu²,

Diniz³

et al. 2014

Polímeros

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“…Santoflex IP and PBNA were determined in NR, SBR, PBD, SMR20, and IR by reverse-phase chromatography on Separon SE (161).…”

Section: Curing Agents and Age Resistersmentioning

confidence: 99%

Air pollution

Fox¹,

Jeffries²

1983

Anal. Chem.

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“…It is found out that heterocyclic compounds containing hydroquinoline derivatives are the basis for a wide range of biological activities [24][25][26] and also have industrial applications such as photo sensitizers in solar cells [27][28][29] and additives to polymers [30,31]. Hence, the construction of new heterocyclic assemblies and functionalization of hydroquinoline compounds have attracted the attention of synthetic organic chemists to further realize their versatile potential.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and PASS-Assisted Evaluation of New Heterocyclic Compounds Containing Hydroquinoline Scaffold

Manahelohe,

Shikhaliev

2024

Preprint

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Now day; the interest for the synthesis of heterocyclic compounds containing hydroquinoline fragments has increased tremendously due to their wide variety of pharmaceutical and industrial applications. This work details the synthesis of linear and fused heterocyclic systems containing hydroquinoline fragments and the pharmacological activity spectra of the synthesized compounds was predicted by in silico method using Prediction of Activity Spectra of Substances (PASS) program. 1,2,2,4-tetramethyl-1,2-dihydroquinoline-6-carbaldehyde 5a was reacted for three hours with a system of hydroxylammonium chloride/pyridinium chloride/toluene to produce 1,2,2,4-tetramethyl-1,2-dihydroquinoline-6-nitrile 7. N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehyde 6b and iodine reacted at room temperature in aqueous ammonia water, followed by aq. treatment with Na2S2O3 and produced N-benzyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-nitrile 8. 30-60% 2-phenyl-1,3-oxazol-5(4H)-ones 9a,b; 10a,b were synthesized via the condensation reaction of N-alkylhydroquinoline-6-carbaldehydes 5a,b; 6a,b with hippuric acid in acetic acid. When activated 7-methylazolopyrimidines 11a,b were reacted with N-alkyl-2,2,4-trimethyl-1,2,3,4-tetrahydroquinoline-6-carbaldehydes 6a,b, the reaction produced 60–70% yield of 7-[(E)-2,2,4-trimethylhydroquinolin-6-ylidenemethyl]azolo[1,5-a]pyrimidin-6-yl carboxylic acids 12a,b. The condensation reaction of 7-hydroxy-1,2,2,4-tetramethyl-1,2-dihydroquinoline 3h with dimethylacetylenedicarboxylate (DMAD) and ethylacetoacetate afforded methyl (Z)-2-(5,7,7,8-tetramethyl-2-oxo-7,8-dihydrofuro[3,2-g]quinolin-3(2H)-ylidene)acetate 16 and 4,6,8,8,9-pentamethyl-8,9-dihydro-2H-pyrano[3,2-g]quinolin-2-one 17, respectively. The condensation reaction of 6-formyl-7-hydroxy-1,2,2,4-tetramethyl-1,2-dihydroquinoline 5e with methylene active compounds ethylcyanoacetate/dimethyl-3-oxopentanedioate/ ethylacetoacetate/diethylmalonate/Meldrum’s acid afforded 3-substituted dihydroquinoline containg coumarins 19 & 21. A pentacyclic coumarin 22 was obtained via the random condensation reaction of malononitrile with 5e in the presence of catalytic amount of piperidine in ethanol. The potential biological activities of the synthesized compounds were evaluated using PASS computer program. According to the prognosis, (E)-4-(N-alkylhydroquinolin-6-yl)-3-buten-2-ones, 13a, b & 14 showed high probability of being active (Pa) as the Gluconate 2-dehydrogenase inhibitor, Anti-allergic, Anti-asthmatic, and Anti-arthritic with the Pa value of 0.849-0.870. It was also found out that hydroquinolinecarbonitrile compounds 7 & 8 have a propensity to act as a good progesterone antagonists, anti-allergic, anti-asthmatic, and anti-arthritic (Pa = 0.276-0.827). Among the coumarin moieties containing hydroquinolines, compounds 17, 19a, and 19c were predicted to be good progesterone antagonists with the Pa values of 0.710, 0.630 and 0.615; respectively.

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The analysis of polymeric 2,2,4‐trimethyl‐1,2‐dihydroquinoline

Cited by 4 publications

References 7 publications

Characterization of Additives Typically Employed in EPDM Formulations by using FT-IR of Gaseous Pyrolyzates

Characterization of Additives Typically Employed in EPDM Formulations by using FT-IR of Gaseous Pyrolyzates

Air pollution

Synthesis and PASS-Assisted Evaluation of New Heterocyclic Compounds Containing Hydroquinoline Scaffold

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