Polymerization Reactions of Itaconic Acid and Some of Its Derivatives

Marvel, C. S.; Shepherd, Thomas H.

doi:10.1021/jo01087a006

Cited by 130 publications

(67 citation statements)

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“…Large scale fermentation processes using molasses as the carbohydrate source have now been developed. While itaconic acid can be polymerized in aqueous solution using potassium persulphate as initiator (7,8) it is not a particularly easy reaction and has not been widely used. Improved yields and molecular weights can be obtained if the anhydride is used with subsequent hydrolysis of the polymer to the polyitaconic acid (9).…”

Section: Introductionmentioning

confidence: 99%

Physical properties of polymers based on itaconic acid

Cowie¹

1979

Pure and Applied Chemistry

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Section: Introductionmentioning

confidence: 99%

Physical properties of polymers based on itaconic acid

Cowie¹

1979

Pure and Applied Chemistry

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“…1). 14 Since the corresponding double bond in 2-methylfumaric acid is substantially less reactive than the one in IA, the reaction conditions for the polycondensation were carefully adjusted to reach the targeted monomer conversion without significant isomerization.…”

Section: Resultsmentioning

confidence: 99%

“…The 1,1-disubstituted unsaturation in IA makes it homopolymerizable to some degree because the unsaturation is more reactive compared to the double bond in malate. 13,14 IA has received significant attention during recent years, most likely due to its interesting dual functionality and the possibility of producing it from renewable resources. There are several recent studies on polymerizing IA with different diols to obtain renewable, unsaturated polyesters for various applications, as recently reviewed by Robert and Friebel.…”

Section: Introductionmentioning

confidence: 99%

Biobased UV-curable coatings based on itaconic acid

2017

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A series of renewable unsaturated polyesters were synthesized from itaconic acid (IA), succinic acid, and 1,4-butanediol by solvent-free polycondensation. Previous studies utilizing IA to make polyesters for coating applications have shown great potential; however, the curing and material properties have not been investigated in detail. The aim of this study was to investigate how the curing is affected by the amount of unsaturations and how well itaconate-based polyesters crosslink without the addition of any other unsaturated monomers or reactive diluents. The chemical structures of the polyesters were confirmed with FTIR, 1 H-NMR, and THF-SEC. The degree of curing was studied with FTIR, and the mechanical properties of the crosslinked polyesters were evaluated with DMA, pendulum hardness, and microindentation. The degree of curing was found to be up to 75%, and furthermore, it was found that the final mechanical properties of the crosslinked coatings could be tuned by modifying the IA content in the monomer composition. The results from DMA showed that there is a clear trend between mechanical properties and crosslinking density.

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“…The first homopolymerization of IA reported in 1959 was carried in a 0.5M hydrochloric acid solution with K 2 S 2 O 8 as an initiator, and it took several days to achieve 35% yield. 15 IA was also polymerized in methanol at room temperature with 2,2Ј-azo-bis-isobutyronitrile (AIBN) as a free-radical initiator, and it took 30 days to reach 70% yield. 16 In our previous research, we found that in the presence of a redox initiation system consisting of NaH 2 PO 2 and K 2 S 2 O 8 , IA can polymerize in an aqueous solution.…”

Section: Introductionmentioning

confidence: 99%

Crosslinking cotton with poly(itaconic acid) and in situ polymerization of itaconic acid: Fabric mechanical strength retention

Yang

Lickfield

2003

J of Applied Polymer Sci

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Polycarboxylic acids have been used as nonformaldehyde durable press finishing agents for cotton fabrics. Previously, we found that itaconic acid (IA) polymerized in situ on cotton fabric and also in an aqueous solution in the presence of a K 2 S 2 O 8 /NaH 2 PO 2 initiation system. Both poly(itaconic acid) (PIA) and the polymer formed by in situ polymerization of IA are able to crosslink cotton cellulose, thus imparting wrinkle resistance to cotton. In this research, we compared the performance of the cotton fabric crosslinked by PIA and that crosslinked by in situ polymerization of IA. The fabric treated with PIA and that treated with IA had similar wrinkle recovery angles. The cotton fabric treated with IA, however, lost more tensile strength than that treated with PIA due to cellulose degradation. We determined the magnitude of the fabric tensile strength loss attributed to crosslinking by separating the tensile strength loss due to cellulose degradation from the total tensile strength loss, and found that the tensile strength loss caused by crosslinking for the fabric treated with PIA was significantly higher than that for the fabric treated with IA. This can probably be attributed to more concentrated crosslinkages formed on the near surface of the PIA-treated cotton fabric. PIA had poorer penetration into the amorphous cellulose region in fiber interior due to its much larger molecular size, thus increasing its concentration on the fabric's near surface. The data also suggest that more concentrated crosslinkages on the fabric surface reduced fabric abrasion resistance.

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Polymerization Reactions of Itaconic Acid and Some of Its Derivatives

Cited by 130 publications

References 0 publications

Physical properties of polymers based on itaconic acid

Physical properties of polymers based on itaconic acid

Biobased UV-curable coatings based on itaconic acid

Crosslinking cotton with poly(itaconic acid) and in situ polymerization of itaconic acid: Fabric mechanical strength retention

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