Homo- and co-polymerisation of di(propylene glycol) methyl ether methacrylate – a new monomer

Constantinou, Anna P.; Patias, Georgios; Somuncuoğlu, Birsen; Brock, Toby; Lester, Daniel W.; Haddleton, David M.; Georgiou, Theoni K.

doi:10.1039/d1py00444a

Cited by 14 publications

(13 citation statements)

References 64 publications

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“…The peak at δ167.8 ppm in the 13 C NMR spectrum of GA (Figure S1a) corresponding to the carbonyl group shifted to ∼165 ppm in spectra of TGPME-1, TGPME-2, and TGPME-3 (Figure S1b–d), which could be attributed the successful esterification of GA with polypropylene glycol monomethyl ether . Meanwhile, new signals at 17–21 ppm belong to the carbon of the branched chain methyl group, and the peaks at ∼50 and ∼44 ppm contributed to the carbon from the epoxy group, as shown in Figure S1b–d, implying the existence of triepoxy gallic acid-based polypropylene glycol monomethyl ether esters.…”

Section: Resultsmentioning

confidence: 96%

Synthesis of Gallic Acid-Derived Plasticizers for Polyvinyl Chloride Featuring Excellent Plasticization, Thermo-Stability, and Migration Resistance

Tan,

Huang,

et al. 2023

ACS Appl. Polym. Mater.

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The development of a facile and environmental strategy for manufacturing a natural aromatic-derived plasticizer for poly(vinyl chloride) (PVC) featuring excellent plasticization, UVshielding, and thermostability, together with migration resistance, is still a challenge. Herein, a series of gallic acid-derived polypropylene glycol monomethyl ether esters with natural aromatic rings (TGPME-n, n = 1, 2, or 3 referring to the number of methylethoxy units in the structure of TGPME-n) were developed as plasticizers for PVC via the simple esterification of gallic acid with polypropylene glycol monomethyl ether and sequent etherification with epichlorohydrin in a one-pot process without any HCl generation. Extensive experiments showed that the performances of PVC blended with TGPME-n were highly dependent on the number of methylethoxy units from TGPME-n, where the performances of PVC plasticized by TGPME-n with more methylethoxy units were better than those of TGPME-n bearing one. Benefiting from the strong interaction of aromatic and polar groups (epoxy, ethoxy, and ester groups) in TGPME-n with a PVC skeleton, plasticization, low temperature resistance, thermal stability, transparency, and UV-shielding as well as migration resistance of PVC plasticized by TGPME-3 with maximum methylethoxy units were superior to those of PVC blended with dioctyl phthalate (DOP), implying that TGPME-3 could be used as an attractive alternative to totally replace the toxic DOP. This study provides a simple and feasible strategy to fabricate a highly efficient natural aromatic-derived plasticizer for the PVC industry.

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Section: Resultsmentioning

confidence: 96%

Synthesis of Gallic Acid-Derived Plasticizers for Polyvinyl Chloride Featuring Excellent Plasticization, Thermo-Stability, and Migration Resistance

Tan,

Huang,

et al. 2023

ACS Appl. Polym. Mater.

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“…To visualize the influence of the nature (hydrophobic vs hydrophilic end group), the chain length of the polyester side chain, and polymer composition on the transition (cloud point) temperature, the corresponding plots were constructed (Figure ). For both series of NIPAM copolymers, i.e., those with methacrylate- (Figure a) and acrylate-terminated polyesters (Figure b), the transition temperature decreased with increasing the content of the hydrophobic polyester, which is consistent with the earlier observations on the influence of a hydrophobic comonomer on the cloud point temperature. − ,− It should be noted that all of the dependences are close to linear for all of the copolymer compositions studied, with the exception of a small region with a very low comonomer content for P(NIPAM- co -PLA-MA600) and P(NIPAM- co -PLA-A500), respectively (Figure ). A similar behavior was observed for copolymers of NIPAM with 2-acrylamidephenylboronic acid or 2-hydroxyethyl acrylate with 2-methoxyethylacrylate .…”

Section: Resultsmentioning

confidence: 99%

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Ksendzov

Nikishau

Зурина

et al. 2022

ACS Appl. Polym. Mater.

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A series of well-defined poly(D,L-lactide) and poly(ε-caprolactone) macromonomers (M n of ∼ 600 and ∼1200 Da) bearing a (meth)acrylate group at one side of the chain and either a hydrophobic nonpolar butyl group or a hydrophilic polar hydroxyl group at the other side of the chain were synthesized via 1,8-diazabicyclo[5.4.0]undec-7-ene-catalyzed ring-opening polymerization (ROP) of D,L-lactide and methanesulfonic acidcatalyzed ROP of ε-caprolactone, respectively. Then, a series of well-defined random copolymers (M n of ∼ 30 000 Da, Đ < 1.25) were prepared via reversible addition−fragmentation chain transfer (RAFT)-mediated copolymerization of N-isopropylacrylamide with these macromonomers. It was found that the cloud point temperature of the graft copolymers almost linearly decreased from 32.1 to ∼14 °C, with increasing the content of the polyester macromonomer with a hydrophobic butyl end group in a copolymer chain from 0 to 17 wt %. A much smaller shift in the transition temperature (from 32.1 to ∼ 23 °C) was observed for the graft copolymers of N-isopropylacrylamide with polyesters bearing a polar hydroxyl group at the chain end. The thermoresponsive behavior dependence on the copolymer composition of the synthesized graft copolymers or their binary mixtures with poly(N-isopropylacrylamide) (PNIPAM) was also demonstrated in this study. Finally, it was proved that the obtained graft copolymers showed no cytotoxicity, and films prepared from these copolymers displayed better cell adhesion as compared to those prepared from neat PNIPAM.

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“…As the concentration of the gelling agent increases, the number of micelles increases; thus, more junction points are formed within the gel structure, leading to a stronger gel. This is a well-established phenomenon, and it has been previously observed in solutions consisting of a single gelling agent, such as methacrylate polymers [57,62] and poly(N-isopropylacrylamide)-based polymers [63,64].…”

Section: Homopolymers As Additives In Thermogelling Triblock Copolymer Solutions-rheological Propertiesmentioning

confidence: 73%

Homopolymer and ABC Triblock Copolymer Mixtures for Thermoresponsive Gel Formulations

Constantinou

Provatakis

et al. 2021

Gels

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Our group has recently invented a novel series of thermoresponsive ABC triblock terpolymers based on oligo(ethylene glycol) methyl ether methacrylate with average Mn 300 g mol‒1 (OEGMA300, A unit), n-butyl methacrylate (BuMA, B unit) and di(ethylene glycol) methyl ether methacrylate (DEGMA, C unit) with excellent thermogelling properties. In this study, we investigate how the addition of OEGMA300x homopolymers of varying molar mass (MM) affects the gelation characteristics of the best performing ABC triblock terpolymer. Interestingly, the gelation is not disrupted by the addition of the homopolymers, with the gelation temperature (Tgel) remaining stable at around 30 °C, depending on the MM and content in OEGMA300x homopolymer. Moreover, stronger gels are formed when higher MM OEGMA300x homopolymers are added, presumably due to the homopolymer chains acting as bridges between the micelles formed by the triblock terpolymer, thus, favouring gelation. In summary, novel formulations based on mixtures of triblock copolymer and homopolymers are presented, which can provide a cost-effective alternative for use in biomedical applications, compared to the use of the triblock copolymer only.

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Homo- and co-polymerisation of di(propylene glycol) methyl ether methacrylate – a new monomer

Abstract: In this study, a new methacrylate monomer with two propylene glycol groups on the side chain, di(propylene glycol) methyl ether methacrylate (diPGMA), was synthesised via an esterification reaction. This new...

Cited by 14 publications

References 64 publications

Synthesis of Gallic Acid-Derived Plasticizers for Polyvinyl Chloride Featuring Excellent Plasticization, Thermo-Stability, and Migration Resistance

Synthesis of Gallic Acid-Derived Plasticizers for Polyvinyl Chloride Featuring Excellent Plasticization, Thermo-Stability, and Migration Resistance

Graft Copolymers of N-Isopropylacrylamide with Poly(d,l-lactide) or Poly(ε-caprolactone) Macromonomers: A Promising Class of Thermoresponsive Polymers with a Tunable LCST

Homopolymer and ABC Triblock Copolymer Mixtures for Thermoresponsive Gel Formulations

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