Tunable Hydrophilicity of Poly(ethyl lactate acrylate-<i>co</i>-acrylic acid)

Purushothaman, M.; Krishnan, P. Santhana Gopala; Nayak, Sanket

doi:10.7569/jrm.2015.634114

Cited by 4 publications

(6 citation statements)

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“…The structure of both monomers was verified by NMR and high-resolution mass spectrometry (Figures S1–S4). Previously, our group and others demonstrated that ELA is prone to polymerize either by FRP or LRP to deliver water-insoluble rubbery polymers (i.e., PELA). − The ability of DMLA to polymerize by FRP using AIBN as the initiator was confirmed by 1 H NMR and GPC. 1 H NMR analysis indicated 96% monomer conversion after 8 h at 90 °C.…”

Section: Resultsmentioning

confidence: 88%

“…The chemical structure of EL and DML is also of great appeal to expand the scope of potential application of these green solvents as sustainable feedstock for sustainable polymer synthesis. − Their secondary alcohol offers a simple access to monovinyl derivatives for use in either free or living radical chain growth polymerizations (FRP and LRP, respectively). In this regard, a few publications reported that acrylic and methacrylic derivatives of lactic acid esters (i.e., methyl, ethyl, butyl) are suitable to polymerize by FRP to yield water-insoluble rubbery polymers. − More recently, our group also reported that well-defined polymers derived from this toolbox of monomers are easily accessible by Cu(0) wire-mediated SET-LRP. , However, vinylic derivatives of N -alkyl lactamides and polymers thereof are only reported in the old patent literature, and no study on their physical properties, LRP as well as block copolymer (BCP) synthesis, is yet available to the best of our knowledge.…”

Section: Introductionmentioning

confidence: 99%

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Photoinduced Upgrading of Lactic Acid-Based Solvents to Block Copolymer Surfactants

Bensabeh

Moreno

Roig

et al. 2019

ACS Sustainable Chem. Eng.

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We report a new strategy toward the development of block copolymer surfactants from chemicals of the lactic acid family. A particularly unique aspect of this work is the use of green solvents as biobased platform chemicals to generate well-defined and nanostructure-forming materials. Herein, efficient functionalization of ethyl lactate (EL) and N,N-dimethyl lactamide (DML) solvents with acrylate groups generated monomers that could be polymerized by the photoinduced copper-catalyzed living radical polymerization process to yield polymeric materials with different water solubilities. These lactic acid-derived monomers were used as a major component in well-defined diblock copolymers composed of poly(EL acrylate) and poly(DML acrylate) segments as hydrophobic and hydrophilic building blocks, respectively. The resulting amphiphilic copolymers could self-assemble in aqueous solution to form nanoparticles with different morphologies (e.g., large-compound micelles and vesicles). Subsequently, the formed amphiphilic polymers were employed as efficient stabilizers in the emulsion polymerization of methyl methacrylate and styrene, offering a facile method for the synthesis of well-defined and stable polymer latexes in the range of 100–200 nm, demonstrating the practical significance of these biobased polymers in nanomaterial synthesis.

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Section: Resultsmentioning

confidence: 88%

Section: Introductionmentioning

confidence: 99%

Photoinduced Upgrading of Lactic Acid-Based Solvents to Block Copolymer Surfactants

Bensabeh

Moreno

Roig

et al. 2019

ACS Sustainable Chem. Eng.

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“…In our previous work, we synthesized series of poly(alkyl lactate acrylate)s [16,17], poly(alkyl lactate methacrylate)s [18,19] and poly(ethyl lactate acrylate-co-acrylic acid) [20]. Among them poly(butyl lactate methacrylate) exhibited highest moisture absorption of about 24% (wt/wt) at 97% RH in 30 ± 1°C [18].…”

Section: Functional Polymersmentioning

confidence: 98%

Effect of butyl lactate methacrylate content on the properties of acrylic acid copolymers

Purushothaman¹,

Krishnan

Nayak

2016

Polym. Sci. Ser. A

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In the present work, the effect of butyl lactate methacrylate (BLM) content on the properties of acrylic acid (AA) copolymers was investigated. The BLM monomer was synthesized by reacting butyl lactate with methacrylic acid through azeotropic distillation method, which was confirmed by Mass spectrometric technique. Copolymers were synthesized by free-radical solution polymerization technique to obtain poly(BLM-co-AA). BLM monomer and copolymers were characterized by Fourier transform infrared (FTIR), 1 H-nuclear magnetic resonance ( 1 H-NMR) and proton decoupled 13 C-NMR spectroscopic techniques. The Finemann-Ross method was used to determine the reactivity ratio of AA and BLM and the values were found to be 0.79 and 0.39, respectively. The wide angle X-ray scattering (WAXS) studies exhibited that the increase in BLM content in copolymers, shifted the amorphous halo from 21.34° to 15.39° and also increased the average molecular interchain spacing (〈R〉) from 5.20 to 7.18 Å, which was calculated from 2θ values of amorphous halo of copolymers. Moisture absorption of polymers followed Fickian absorption. Depending upon the copolymer composition, relative humidity and time, the moisture absorption of copolymers can be tuned to a wide range from 11 to 35% (wt/wt). Glass transition temperature of copolymers decreased from 106 to 72.1°C with increase in BLM content. Copolymers were thermally stable up to 150°C and thereafter exhibited three-step thermal degradation in nitrogen atmosphere. Thermal stability of copolymers can be explained on the basis of 〈R〉 value.

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“…As reported in previous publications, alkyl lactate solvents are appealing chemicals to prepare biorenewable acrylic/methacrylic polymers [23][24][25][26][27][28][29]. Here, BuLA was prepared from L-butyl lactate (BuL) by acylation with acryloyl chloride in the presence of base using a solvent with low environmental impact such as Me-THF (Figure 1).…”

Section: Bula Monomer Synthesis and Raft Polymerization Model Studiesmentioning

confidence: 98%

“…Among them, polylactide (PLA), most commonly synthesized by the ring-opening polymerization of the cyclic dimer of lactic acid, is a good alternative replacement for the traditional petroleum-sourced polystyrene glassy end-blocks in ABA TPEs, due to their high modulus characteristics [21]. The potential of alkyl lactate esters, e.g., methyl, ethyl and butyl, goes beyond their well-recognized use as eco-friendly solvents [22], as their secondary alcohol offers a simple access to monovinyl derivatives prone to polymerization by radical mechanisms [23][24][25][26]. In this regard, our group reported that poly(alkyl lactate ester) (meth)acrylates with controlled molecular weight, narrow molecular weight distribution and high end-group fidelity are also easily accessible by Cu(0) wire-mediated single-electron transfer living radical polymerization (SET-LRP) [27,28].…”

Section: Introductionmentioning

confidence: 99%

Biosourced All-Acrylic ABA Block Copolymers with Lactic Acid-Based Soft Phase

et al. 2020

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Lactic acid is one of the key biobased chemical building blocks, given its readily availability from sugars through fermentation and facile conversion into a range of important chemical intermediates and polymers. Herein, well-defined rubbery polymers derived from butyl lactate solvent were successfully prepared by reversible addition–fragmentation chain transfer (RAFT) polymerization of the corresponding monomeric acrylic derivative. Good control over molecular weight and molecular weight distribution was achieved in bulk using either monofunctional or bifunctional trithiocarbonate-type chain transfer agents. Subsequently, poly(butyl lactate acrylate), with a relative low Tg (−20 °C), good thermal stability (5% wt. loss at 340 °C) and low toxicity was evaluated as a sustainable middle block in all-acrylic ABA copolymers using isosorbide and vanillin-derived glassy polyacrylates as representative end blocks. Thermal, morphological and mechanical properties of copolymers containing hard segment contents of <20 wt% were evaluated to demonstrate the suitability of rubbery poly(alkyl lactate) building blocks for developing functional sustainable materials. Noteworthy, 180° peel adhesion measurements showed that the synthesized biosourced all-acrylic ABA copolymers possess competitive performance when compared with commercial pressure-sensitive tapes.

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Tunable Hydrophilicity of Poly(ethyl lactate acrylate-co-acrylic acid)

Cited by 4 publications

References 0 publications

Photoinduced Upgrading of Lactic Acid-Based Solvents to Block Copolymer Surfactants

Photoinduced Upgrading of Lactic Acid-Based Solvents to Block Copolymer Surfactants

Effect of butyl lactate methacrylate content on the properties of acrylic acid copolymers

Biosourced All-Acrylic ABA Block Copolymers with Lactic Acid-Based Soft Phase

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