<scp>L</scp>‐arabinitol‐based functional polyurethanes

Ferris, Cristina; de-Paz, M.-Violante; Galbis, Juan A.

doi:10.1002/pola.24530

Cited by 27 publications

(37 citation statements)

References 22 publications

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“…We have initially tested this method with the preparation of one highly hydroxylated PU after the effi cient post-functionalization of a tri-O -allyl-L-arabinitol-based PU "via" thiol-ene reaction. [ 15 ] Therefore, the suitability of this procedure for the preparation of both, aromatic and aliphatic multifunctional PUs -bearing diverse polar and ionic functional groups -would need to be investigated.…”

Section: 34-trimentioning

confidence: 99%

“…The utilization of tert -butyl-(2-mercaptoethyl) carbamate (3) (with the amine group conveniently protected) prevented these side reactions (Scheme 3 ). While the polymers were directly modifi ed by a simple CC procedure, these changes can also be accomplished before the polymerization takes place, as is shown in Scheme 3 for the preparation of PU[Ar(S-NH 2 ) 3 -HMDI)] (15). Although the use of cysteamine as thiol moiety would lead to the total consumption of allyl groups in 1,5-di-O -trityl-2,3, 4-tri-O -allyl-L -arabinitol, the amino …”

Section: (C-n) 1052 (C-o-c) CMmentioning

confidence: 99%

“…The synthesis of the diol monomers was accomplished following the synthetic strategy recently reported by us. [ 15 ] The precursor polymers PU(ArAll 3 -MDI) (6), PU(ArAll 2 -MDI) (7), PU(ArAll 3 -HMDI) (8), and PU(ArAll 2 -HMDI) (9) were prepared by reaction of 2,3,4-tri-O -allyl-L -arabinitol (ArAll 3 , 1) or 3,4-tri-O -allyl-2-O -methyl-L -arabinitol (ArAll 2 , 2) with HMDI or MDI (Scheme 1 ). The polymerization took place under argon atmosphere at 25 or 60 ºC in DMF for 5 h to ensure the total consumption of diol monomer.…”

Section: Synthesis Of Functionalized Polymersmentioning

confidence: 99%

“…All glassware was heated overnight at 80 ° C before use, and after assembly was further heated under vacuum to eliminate the surface moisture. The diol monomers 2,3,4-tri-O -allyl-L -arabinitol (ArAll 3 , 1) [ 15 ] and 3,4-tri-O -allyl-2-methyl-L -arabinitol (ArAll 2 , 2) [ 15 ] were dried under high vacuum for at least 3 d. 1,6-Hexamethylene diisocyanate (HMDI) and 4,4 ′ -methylenebis(phenyl isocyanate) (MDI) were stored at 4 ° C, and handled under inert atmosphere. N,NDimethylformamide (DMF) was used as polymerization solvent.…”

Section: Introductionmentioning

confidence: 99%

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Synthesis of Functional Sugar‐Based Polyurethanes

Ferris

de-Paz

Galbis

2012

Macro Chemistry & Physics

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Three new polyurethanes (PUs) with multiple pendant allyl groups were synthesized from L -arabinitol as versatile materials for the preparation of tailor-made PUs with varying degrees of functionalization. Their allyl functional groups can take part in thiol-ene reactions to obtain greatly diverse materials. Thus, six new highly functional PUs were prepared by click chemistry to give polymers with NHBoc [NH-CO-OC(CH 3 ) 3 ], amino, carboxylic, and 1,2-dihydroxyethyl side groups. The thermal stability of the novel PUs was investigated by thermogravimetric analysis and differential scanning calorimetry. This strategy provides a simple and versatile platform for the design of new materials whose functionality can be easily modifi ed to anchor diverse biologically active molecules.following: (a) the incorporation of functional groups in the diol moiety without previous protection, as hydroxyl, [ 8 ] carboxy, [9][10][11] alkynyl [ 5 , 12 , 13 ] or allyl groups, [ 14 , 15 ] and oxazolidine-functionalized PUs [ 16 ] or disulfi de bonds [ 17 ] among others; or (b) in certain cases, functional groups were previously protected as NHBoc moieties [ 18 ] or benzyl ether groups, [ 19 ] and later deprotected once the polymerization had taken place. The diisocyanates do not usually bear any functional group -apart from one example found in the literature (maleimide units). [ 20 ] The methods mentioned above incorporate just one type of functional group each time, the preparation of different diol or diisocyanate monomers is required and poor control on the degree of functionalization is sometimes accomplished. In a previous paper of our group, [ 19 ] we had attempted the preparation of multihydroxylated PUs by using a conveniently protected sugar diol monomer in which secondary groups were blocked as benzyl ethers. Deprotection of secondary hydroxyl groups required severe reaction conditions and was poorly controlled. At most, debenzylation proceeded close to 70% after 5 d of reaction.Therefore, it would be of interest to fi nd a procedure to transform a certain polymer into functionalized new materials by means of a simple and straightforward reaction. To deal with this issue, we now present a strategy based on the use of di-and tri-O -allyl diol monomers for polymerization with aromatic or aliphatic diisocyanates

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Section: 34-trimentioning

confidence: 99%

Section: (C-n) 1052 (C-o-c) CMmentioning

confidence: 99%

Section: Synthesis Of Functionalized Polymersmentioning

confidence: 99%

Section: Introductionmentioning

confidence: 99%

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Synthesis of Functional Sugar‐Based Polyurethanes

Ferris

de-Paz

Galbis

2012

Macro Chemistry & Physics

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“…Therefore, 35 methods leading to functionalized PUs equipped with reactive groups along their backbone 36 remain of particular interest. These functional groups can be converted using 'click' chemistry, 37 providing paths to unique materials with enhanced properties for high-end applications. between n-propylamine 6, -thiobutyrolactone 7 and n-butyl acrylate 8 was studied in detail…”

mentioning

confidence: 99%