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Novel Homo-and Co-polymers Based on 7-Methacryloyloxy-4-methylcoumarin: Synthesis, Antimicrobial Activity, Pour-Point Depressants and Their Effects on the Rheology of the Waxy Cru

Article

Last updated: 01 Jan 2025

Subjects

-

Tags

Polymer chemistry

Abstract

This study aimed to synthesize new polymeric additives including homo- and co-polymers based on 4-methyl-2-oxo-2H-chromen-7-yl methacrylate monomer and evaluating their activity as potential antimicrobials and as pour-point depressants for modification of waxy crude oil rheology. The resultant compounds were characterized by their IR, 1H NMR and 13C NMR spectral data. The formation of the new polymers, namely, poly(7-methacryloyloxy-4-methylcoumarin) [poly(MAOMC)] homo-polymer, poly(7-methacryloyloxy-4-methylcoumarin-co-vinylacetate) [poly(MAOMC)-co-(VA)] and poly(7-methacryloyloxy-4-methylcoumarin-co- octadecyl 4-(methacryloyloxy)benzoate) [poly(MAOMC)-co-(OMAOB)] co-polymers was based on free radical polymerization. The polymerization reaction was carried at 70±2°C using 2,2'-azobisisobutyronitrile (AIBN) as an initiator and dimethylformamide (DMF)/toluene as a solvent in the case of homo-polymer [poly(MAOMC)] and co-polymer [poly(MAOMC)-co-(VA)], while polymerization proceeds at the same temperature by using benzoyl peroxide as an initiator and toluene as a solvent in the case of co-polymer [poly(MAOMC)-co-(OMAOB)]

The activities of the resultant compounds as potential antibacterial agents were evaluated against the two Gram-positive (Bacillus cereus and Staphylococcus aureus), the four Gram-negative (Escherichia coli, Neisseria gonorrhoeae, Pseudomonas aeruginosa, and Salmonella typhimrium) bacterial strains, and as antifungal agents against two fungal species (Aspergillus flavus and Candids albicans). The results showed that MAOMC monomer and poly(MAOMC)-co-(OMAOB) copolymer indicated moderate potent activity towards the bacterial and fungal strains used. At the other extreme, the influence of coumarin and octadecyl benzoate based compounds on the pour-point depression and on the rheological properties of crude oil with low asphaltene content was studied. The results indicated that all three polymers exhibited very good efficiency as additives to improve the flow-ability of the tested crude oil. Moreover, the poly(MAOMC)-co-(OMAOB) co-polymer was found to exhibit the highest performance to reduce and depress the pour-point of the tested crude oil and decrease the viscosity to a large extent due to the presence of two aromatic units with the long aliphatic carbon chain in its structure.

DOI

10.21608/ejchem.2021.56228.3206

Keywords

Coumarin, pour-point depressants, rheology, poly(7-methacryloyloxy-4-methylcoumarin), poly(7-methacryloyloxy-4-methylcoumarin-co-vinylacetate), poly(7-methacryloyloxy-4-methylcoumarin-co- octadecyl 4-(methacryloyloxy)benzoate)

Authors

First Name

Ahmed

Last Name

Hefny

MiddleName

M. K.

Affiliation

Department of Chemistry, Faculty of Science, Helwan University; Ain Helwan, Cairo 11795, A. R. Egypt

Email

ah.kamal89@gmail.com

City

Cairo

Orcid

-

First Name

Ashraf

Last Name

Ashmawy

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science (boys), AL-Azhar University, 11884, A. R. Egypt

Email

ashraf_ashmawy2002@azhar.edu.eg

City

obour city

Orcid

0000-0002-8006-7605

First Name

Samia

Last Name

Elazabawy

MiddleName

R.

Affiliation

Department of Chemistry, Faculty of Science, Helwan University; Ain Helwan, Cairo 11795, A. R. Egypt

Email

samiaeradwan@science.helwan.edu.eg

City

Cairo

Orcid

-

First Name

Amira

Last Name

Abdallah

MiddleName

-

Affiliation

Department of Chemistry, Faculty of Science, Helwan University; Ain Helwan, Cairo 11795, A. R. Egypt

Email

amiraelsayed135@yahoo.com

City

Cairo

Orcid

0000-0002-6773-3634

First Name

El sayed

Last Name

Elnaggar

MiddleName

M.

Affiliation

Department of Chemistry, Faculty of Science (boys), AL-Azhar University, 11884, A. R. Egypt

Email

elsayed_elmhdy80@yahoo.com

City

Cairo

Orcid

-

Volume

64

Article Issue

4

Related Issue

22914

Issue Date

2021-04-01

Receive Date

2021-01-02

Publish Date

2021-04-01

Page Start

1,941

Page End

1,955

Print ISSN

0449-2285

Online ISSN

2357-0245

Link

https://ejchem.journals.ekb.eg/article_141189.html

Detail API

https://ejchem.journals.ekb.eg/service?article_code=141189

Order

26

Type

Original Article

Type Code

297

Publication Type

Journal

Publication Title

Egyptian Journal of Chemistry

Publication Link

https://ejchem.journals.ekb.eg/

MainTitle

Novel Homo-and Co-polymers Based on 7-Methacryloyloxy-4-methylcoumarin: Synthesis, Antimicrobial Activity, Pour-Point Depressants and Their Effects on the Rheology of the Waxy Crude Oil

Details

Type

Article

Created At

22 Jan 2023