Phosphonic acid‐based amphiphilic diblock copolymers derived from ROMP

Eren, Tarık; Tew, Gregory N.

doi:10.1002/pola.23425

Cited by 26 publications

(25 citation statements)

References 42 publications

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“…Ring‐opening metathesis polymerization (ROMP) is a versatile technique for the synthesis of various functional block copolymers with well‐defined architecture because of the development of a well‐defined ruthenium catalyst with improved control features and functional group tolerance, and thus become an important objective for the polymerization of functional monomers 1, 2. The synthesis of polymeric core–shell nanoparticles via ROMP using the traditional method has been extensively reported 3–8. Moreover, Nomura et al9 synthesized nanoparticles from the core‐crosslinked soluble star shape polymers by adopting sequential ROMP of norbornene (NBE), crosslinking reagent, and NBE using the molybdenum‐alkylidene initiator; Héroguez and coworkers10 reported NBE and methyl methacrylate being converted to the polymeric composite particles via ROMP and atom transfer radical polymerization (ATRP) in aqueous dispersed media.…”

Section: Introductionmentioning

confidence: 99%

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Yuan

Page

et al. 2010

Cancer

399

270

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BACKGROUNDIpilimumab is a monoclonal antibody that antagonizes cytotoxic T lymphocyte antigen-4, a negative regulator of the immune system. The authors report on advanced refractory melanoma patients treated in a compassionate use trial of ipilimumab at the Memorial Sloan-Kettering Cancer Center.METHODSPatients with advanced refractory melanoma were treated in a compassionate use trial with ipilimumab 10 mg/kg every 3 weeks for 4 doses. Those with evidence of clinical benefit at Week 24 (complete response [CR], partial response [PR], or stable disease [SD]) then received ipilimumab every 12 weeks.RESULTSA total of 53 patients were enrolled, with 51 evaluable. Grade 3/4 immune-related adverse events were noted in 29% of patients, with the most common immune-related adverse events being pruritus (43%), rash (37%), and diarrhea (33%). On the basis of immune-related response criteria, the response rate (CR + PR) was 12% (95% confidence interval [CI], 5%-25%), whereas 29% had SD (95% CI, 18%-44%). The median progression-free survival was 2.6 months (95% CI, 2.3-5.2 months), whereas the median overall survival (OS) was 7.2 months (95% CI, 4.0-13.3 months). Patients with an absolute lymphocyte count (ALC) ≥1000/μL after 2 ipilimumab treatments (Week 7) had a significantly improved clinical benefit rate (51% vs 0%; P = .01) and median OS (11.9 vs 1.4 months; P < .001) compared with those with an ALC <1000/μL.CONCLUSIONSThe results confirm that ipilimumab is clinically active in patients with advanced refractory melanoma. The ALC after 2 ipilimumab treatments appears to correlate with clinical benefit and OS, and should be prospectively validated. Cancer 2010. © 2010 American Cancer Society.This description of 51 patients with advanced, treatment-refractory melanoma who were enrolled in a compassionate use trial of ipilimumab at Memorial Sloan-Kettering Cancer Center confirms that ipilimumab is active in this disease setting. In addition, the results suggest that the absolute lymphocyte count after 2 ipilimumab treatments (at Week 7) highly correlates with the rate of clinical benefit at Week 24 and overall survival.

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Section: Introductionmentioning

confidence: 99%

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Yuan

Page

et al. 2010

Cancer

399

270

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“…The structures of the monomers and polymers are given in Scheme . Homo‐ and copolymer components, monomer 1 and monomer 2, were synthesized by a nucleophilic exchange reaction and a Mitsunobu coupling pathway . The series of polymers, phenyl‐containing homopolymers (2 phenyl ), phosphonate‐containing homopolymers (3 phospho ), and copolymer (2 phenyl ‐ co ‐3 phospho ) with a 4:1 by weight composition, were synthesized by keeping the molecular weight constant ( M n ,th = 50,000 g/mol).…”

Section: Resultsmentioning

confidence: 99%

“…Monomer 2 was synthesized according to the literature . To a dry, round‐bottomed flask were added monomer 1 (3.01 g, 13.2 mmol), triphenylphosphine (4.75 g, 18.1 mmol), diethyl (hydroxymethyl) phosphonate (2.8 mL, 19.0 mmol), and dry THF (30 mL).…”

Section: Methodsmentioning

confidence: 99%

Synthesis of phosphorus‐ and phenyl‐based ROMP polymers and investigation of their effects on the thermomechanical and flammability properties of a polypropylene–IFR system

Turgut

Işıksel

Kahraman

et al. 2017

J of Applied Polymer Sci

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In this study, we present an approach for the synthesis of novel phosphorous‐ or phenyl‐ containing polymers, 2phenyl, 3phospho, and 2phenyl‐co‐3phospho, derived from ring‐opening metathesis polymerization (ROMP), to reduce the flammability of polypropylene (PP). The composites were processed by melt‐blending ROMP polymers and octaphenyl–polyhedral oligomeric silsesquioxane with PP/intumescent flame retardant (IFR) compounds at different compositions. The composites were characterized by limiting oxygen index (LOI), UL‐94, and mechanical tests as well as thermogravimetric analysis (TGA) and differential scanning calorimetry (DSC). The molecular structures of phosphorous‐ and phenyl‐containing polymers were proved by 1H‐NMR, 13C‐NMR, and Fourier transform infrared spectroscopy. The online rheological measurements indicated that the addition of additives to the PP/IFR system increased the melt viscosity of the compounds regardless of the type. The DSC analysis showed that the addition of ROMP polymers to the PP/IFR system influenced the crystal perfection and degree of crystallization. TGA analysis of the composites revealed that the addition of ROMP polymers to PP/IFR compounds deteriorated the thermal stability as the amount of phosphorus increased in the matrix. Dynamic mechanical properties such as storage modulus (E′) and loss modulus (E″) of the composites were lowered by the addition of ROMP polymers. The LOI and UL‐94 rating of PP/IFR were enhanced by the addition of ROMP polymers. It was successfully demonstrated that the novel phosphorous‐ or phenyl‐containing polymers were highly potent additives in optimizing the flammability of PP composites. © 2017 Wiley Periodicals, Inc. J. Appl. Polym. Sci. 2018, 135, 45998.

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“…Rare‐earth metal mediated polymerization has recently be employed to obtain high molecular weight polyvinylphosphonate, which presented exciting opportunities to obtain new macromolecular architectures despite of a few limitations and the methodology is still under investigation . Among the synthetic techniques, ring opening metathesis polymerization (ROMP) has seen an increasing interest in the synthesis of PCPs since 2009 for some reasons: (1) novel norbornene‐based structure (phosphorous on side chain) and some unsaturate linear structure (phosphorous on backbone) can be obtained; (2) olefin methathesis catalysts are highly tolerant of functional groups and reaction conditions are milder (even in ionic liquids) compared to anionic and controlled radical polymerizations; (3) living features and controllability are very good especially when the third generation Grubbs catalyst is used …”

Section: Introductionmentioning

confidence: 99%

“…a few limitations and the methodology is still under investigation. 28 Among the synthetic techniques, ring opening metathesis polymerization (ROMP) has seen an increasing interest in the synthesis of PCPs since 2009 28,29 for some reasons: (1) novel norbornene-based structure (phosphorous on side chain) 28 and some unsaturate linear structure (phosphorous on backbone) 8,30 can be obtained; (2) olefin methathesis catalysts are highly tolerant of functional groups and reaction conditions are milder (even in ionic liquids) 31 compared to anionic and controlled radical polymerizations; 28 (3) living features and controllability are very good especially when the third generation Grubbs catalyst is used. 8,28,30 The current contribution targets at learning the thermal properties of PCPs via ROMP method on the homopolymer and copolymer of norbornene based polymers because these information are very important in applications, 32 however, not paid much attention till now [except in Ref.…”

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confidence: 99%

Phosphonated homopolymers and copolymers via ring opening metathesis polymerization: T _g tuning, flame resistance, and photolithography

Zhang

Xie

et al. 2015

J. Polym. Sci. Part A: Polym. Chem.

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Phosphonated and epoxy‐containing norbornene based monomers were prepared by Diels–Alder reaction. They were then combined with three other commercial cyclic unsaturated monomers to synthesize phosphonated homopolymers and copolymers via ring opening metathesis polymerization (ROMP) using second‐generation Grubbs catalyst. Glass transitions of these polymers were tunable in a broad range from −14 to 91 °C by varying the flexibility of comonomer. Interestingly, copolymerization with cyclopentene inhibited the crystallization of polycyclopentene, and instead, led to a copolymer with two Tgs. Paradoxically, results from thermogravimetric analysis (TGA) were not consistent with the followed flame‐retarding experiment, implying that the early weight loss from phosphonated moieties did not deleteriously affect the flame‐resistant property which actually depended more on the percentage of char residual after thermal degradation. In application studies, the norbornene derivative phosphonated polymer was tested for the first time as flame retarding material, and showed significant self‐extinguishing ability. In a second study, photolithography was also successfully performed via thiol‐ene “click” chemistry, which allowed the phosphonated polymer a promising negative photoresist. © 2015 Wiley Periodicals, Inc. J. Polym. Sci., Part A: Polym. Chem. 2016, 54, 1396‐1408

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Phosphonic acid‐based amphiphilic diblock copolymers derived from ROMP

Cited by 26 publications

References 42 publications

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Synthesis of phosphorus‐ and phenyl‐based ROMP polymers and investigation of their effects on the thermomechanical and flammability properties of a polypropylene–IFR system

Phosphonated homopolymers and copolymers via ring opening metathesis polymerization: T _g tuning, flame resistance, and photolithography

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Phosphonic acid‐based amphiphilic diblock copolymers derived from ROMP

Cited by 26 publications

References 42 publications

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Single‐institution experience with ipilimumab in advanced melanoma patients in the compassionate use setting

Synthesis of phosphorus‐ and phenyl‐based ROMP polymers and investigation of their effects on the thermomechanical and flammability properties of a polypropylene–IFR system

Phosphonated homopolymers and copolymers via ring opening metathesis polymerization: T g tuning, flame resistance, and photolithography

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Phosphonated homopolymers and copolymers via ring opening metathesis polymerization: T _g tuning, flame resistance, and photolithography