Functionalization of hydroxyl terminated polybutadiene with biologically active fluorescent molecule

Sankar, Rajavelu Murali; Saha, Subhadeep; Meera, K. Seeni; Jana, Tushar

doi:10.1007/s12034-009-0075-z

Cited by 23 publications

(5 citation statements)

References 16 publications

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“…We have developed an alternate synthetic method for the attachment of the CDT molecule to the HTPB polymer backbone which does not require the synthesis of CDT molecule. Cyanuric chloride (CYC) have covalently attached at the terminal carbon atoms of the HTPB polymer backbone (scheme 2) (Muralisankar et al 2009b). The modified HTPB (HTPB-CYC hereafter) has been further reacted with NaN 3 to get the azide substitution at the 3,5 position of the attached cyanuric chloride by replacing the chlorine from the CYC moiety (scheme 2).…”

Section: Functionalization Of Htpbmentioning

confidence: 99%

Functionalization of terminal carbon atoms of hydroxyl terminated polybutadiene by polyazido nitrogen rich molecules

2011

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We report a novel synthetic approach for the attachment of the polyazido nitrogen rich molecule on to the hydroxyl terminated polybutadiene (HTPB) backbone. The terminal carbon atoms of the HTPB are functionalized by attaching cyanuric chloride (CYC) covalently on the HTPB backbone. Further reaction of this modified HTPB with sodium azide yields polyazido nitrogen rich HTPB. The unique physico-chemical properties and the microstructure of the HTPB do not get affected upon modification. IR, gel permeable chromatography (GPC) and absorption spectroscopy studies prove that the polyazido nitrogen rich molecules are covalently attached at the terminal carbon atoms of the HTPB. The π electron delocalization owing to long butadiene chain, strong electron withdrawing effect of the triazine molecules are the major driving forces for the covalent attachment of the triazine at the terminal carbon atoms of the HTPB. The disruption of the intermolecular hydrogen bonding between the terminal hydroxyl groups of the HTPB chains and the presence of hydrogen bonding between the N atoms of the triazine ring with OH group of the HTPB are observed. Theoretical study also reveals the existence of the hydrogen bonding between the OH and N. Theoretical calculation shows that the detonation performance of the polyazido nitrogen rich HTPB are very promising.

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Section: Functionalization Of Htpbmentioning

confidence: 99%

Functionalization of terminal carbon atoms of hydroxyl terminated polybutadiene by polyazido nitrogen rich molecules

2011

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“…Hydroxyl-terminated polybutadiene (HTPB) is a diol oligomeric viscous liquid which finds many applications, especially as a binder in solid rocket propellant. − There are several methods, published by us and other groups, that modify the HTPB backbone with varieties of functionality to enhance the physical properties like energy output − and thermal and mechanical strength of resulting PU obtained from HTPB and diisocyanate polymerization. Recently, we demonstrated that attachment of dinitrobenzene (DNB) to the terminal position of HTPB, called HTPB-DNB, has improved the physical properties, especially tensile properties, significantly owing to the formation of supramolecular hydrogen-bonding network fibrilar structure …”

Section: Introductionmentioning

confidence: 99%

Hydrophobic, Water-Dispersible Polyurethane: Role of Polybutadiene Diol Structure

Malkappa

Jana

2015

Ind. Eng. Chem. Res.

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Preparation of stable, free-standing elastic film with hydrophobic surface from water dispersible polyurethanes (WDPUs) is a challenging task. Here, we have prepared WDPUs from polybutadiene based diols and the resulting PU films are satisfying the requisites. Two types of diols namely hydroxyl terminated polybutadiene (HTPB) and terminal functionalized HTPB with dinitrobenzene (DNB) [HTPB-DNB] were used to make WDPUs and the effects of diol structures were investigated. The synthesized WDPUs displayed particle morphology with size in the range of ~130-270 nm and more than one year storage stability. WDPUs yielded stable and free standing films upon curing and the resulting films showed high thermal and mechanical stabilities. The contact angle of the films is in the range of ~ 80-100° attributing the hydrophobic nature of the surface. Hard segment content of the PU was varied from 30-40 % (by weight) to tune the properties of WDPUs and the resulting films.

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“…Hydroxyl-terminated polybutadiene (HTPB) and modified HTPB are important telechelic liquid rubbers that are widely used in the binder system of composite solid propellants. − Because of its unique properties, such as hydrolytic stability, resistance to aqueous acids and bases, adhesion to a variety of substrates, high processability with high solid loading, low-temperature flexibility, electrical insulation properties, and high elongation with good elastic recovery, HTPB is widely used not only in propellant applications but also in other areas, such as membranes, adhesives, coating, sealants, newer materials, etc. The reactive functional groups in the terminated liquid rubber could also be applied to build ABA triblock copolymers, − toughened resins, , elastomers, − cross-linked elastomers, and supermolecular polymer gels. − …”

Section: Introductionmentioning

confidence: 99%

Preparation of Hydroxyl-Terminated Polybutadiene with High Cis-1,4 Content

Zhou

Jie

2014

Ind. Eng. Chem. Res.

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Hydroxyl-terminated polybutadiene (HTPB) with high cis-1,4 content (>95.0%) has been prepared via a two-step method by taking commercial butadiene rubber (BR9000) as a starting material, including the one-pot synthesis of aldehydegroup-terminated polybutadiene (ATPB) in high efficiency and the subsequent reduction reaction. The double bonds distributed in linear polybutadiene were first epoxidized and then cleaved at the exact epoxidized sites. The epoxidation reaction by 3-chloroperbenzoic acid and chain-cleavage reaction by periodic acid are controllable, highly efficient, selective, and quantitative. Along with an epoxy percent increase, the molecular weight of ATPB prepared via a one-pot method decreased with a relatively narrow polydispersity index. The aldehyde groups in the chain ends were reduced by NaBH 4 to produce HTPB, in which the high cis-1,4 content of BR was retained. INTRODUCTIONHydroxyl-terminated polybutadiene (HTPB) and modified HTPB are important telechelic liquid rubbers that are widely used in the binder system of composite solid propellants. 1−6 Because of its unique properties, such as hydrolytic stability, resistance to aqueous acids and bases, adhesion to a variety of substrates, high processability with high solid loading, lowtemperature flexibility, electrical insulation properties, and high elongation with good elastic recovery, 7 HTPB is widely used not only in propellant applications but also in other areas, such as membranes, adhesives, coating, sealants, newer materials, etc. The reactive functional groups in the terminated liquid rubber could also be applied to build ABA triblock copolymers, 8−10 toughened resins, 11,12 elastomers, 13−17 cross-linked elastomers, 18 and supermolecular polymer gels. 19−21 It is well-known that the properties of HTPB are greatly affected by its chain microstructures. 7 Lower 1,2-vinyl content will lead to lower viscosity of HTPB, and the mechanical properties, such as tensile strength and elongation at break, are enhanced with an increase in the 1,4 content. Furthermore, the higher the 1,4 content, especially higher cis-1,4 content, the lower the glass transition temperature and the better the lowtemperature flexibility. 22 Thus, because of its lower viscosity, good mechanical and thermal properties, and low-temperature flexibility, HTPB with high cis-1,4 content might be the best choice for the preparation of new materials with high processability and high elasticity.HTPB was conventionally prepared by free-radical polymerization 23 and anionic polymerization 22 of 1,3-butadiene using a bifunctional initiator. The microstructure, molecular weight, and molecular weight distribution of HTPB were affected by the type of initiator, polarity of the solvent, and polymerization temperature. According to the literature, 23 HTPB prepared by free-radical polymerization had a maximum 79% of 1,4 content, a degree of functionality of 2.1−2.3, and a polydispersity index (PDI) near 2.0. The anionic polymerization process produced HTPB with a maximum 90% of 1,4...

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Functionalization of hydroxyl terminated polybutadiene with biologically active fluorescent molecule

Cited by 23 publications

References 16 publications

Functionalization of terminal carbon atoms of hydroxyl terminated polybutadiene by polyazido nitrogen rich molecules

Functionalization of terminal carbon atoms of hydroxyl terminated polybutadiene by polyazido nitrogen rich molecules

Hydrophobic, Water-Dispersible Polyurethane: Role of Polybutadiene Diol Structure

Preparation of Hydroxyl-Terminated Polybutadiene with High Cis-1,4 Content

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