Novel flame‐retardant thermosets: Phosphine oxide‐containing diglycidylether as curing agent of phenolic novolac resins

Espinosa, M. A.; Galià, Marina; Cádiz, Virgínia

doi:10.1002/pola.20220

Cited by 55 publications

(31 citation statements)

References 16 publications

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“…The 31 P NMR spectra before and after the procedures only indicated the presence of the starting materials. With respect to the safety aspect of future applications it should be noted that phosphine oxides are efficient flame retardants, and that they are not toxic …”

Section: Resultsmentioning

confidence: 99%

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Ahn

Bhuvanesh

Blümel

2017

Chemistry A European J

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The di(hydroperoxy)alkane adducts of phosphine oxides 1-9, Ph PO⋅(HOO) CMe , Cy PO⋅(HOO) CMe , Ph PO⋅ (HOO) CMeEt, Cy PO⋅(HOO) CMeEt, Cy PO⋅(HOO) CEt , Cy PO⋅ (HOO) C(CH ) , Cy PO⋅(HOO) CMePh, (Ph P(O)CH CH P(O)Ph )⋅ ((HOO) CEt ) , and Ph P(O)CH P(O)Ph ⋅(HOO) CMe , respectively, are synthesized and fully characterized by H, C, and P NMR, and IR spectroscopies. Single crystal X-ray structures are reported for 3-9. Different one-pot synthetic pathways, starting from R P, R PO, R PO⋅H O, and R PO⋅H O are explored and discussed and a mechanism for the formation of the di(hydroperoxy)alkane adducts of phosphine oxides is suggested. The longevity of the adducts is tested by monitoring the oxidation of Ph P with quantitative NMR. The solubilities of the adducts in organic solvents are presented, and their applicability as stoichiometric oxidizing agents for the selective oxidation of sulfides to sulfoxides is reported.

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Section: Resultsmentioning

confidence: 99%

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Ahn

Bhuvanesh

Blümel

2017

Chemistry A European J

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“…[24][25][26][27][28][29][30][31] Among the polymers with phosphorus moieties, the polymers with phosphine oxide moieties have major advantages, such as good flame-retardant properties, high thermal oxidative stability, enhanced solubility in organic solvents, improved miscibility and good adhesion to other compounds. [32][33][34][35][36][37][38] In this article, a series of novel flame-retardant PAIs 5a-g containing phosphine oxide moiety were synthesized by the direct polycondensation reactions of svene chiral N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g with bis(3-amino phenyl) phenyl phosphine oxide 4. On other hand, due to presence chiral segments in polymer backbone, these PAIs are optically active.…”

Section: Introductionmentioning

confidence: 99%

Synthesis and properties of novel flame-retardant and thermally stable poly(amideimide) s fromN,N′-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids and phosphine oxide moiety by two different methods

2009

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N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g were synthesized by the condensation reaction of bicyclo[2,2,2]oct-7-ene-2,3,5,6-tetracarboxylic dianhydride 1 with two equimolars of Lalanine 2a, L-valine 2b, L-leucine 2c, L-isoleucine 2d, L-phenyl alanine 2e, L-2-aminobutyric acid 2f and L-histidine 2g in an acetic acid solution. Seven new poly(amide-imide)s PAIs 5a-g were synthesized through the direct polycondensation reaction of seven chiral N,N'-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids 3a-g with bis(3-amino phenyl) phenyl phosphine oxide 4 by two different methods: direct polycondensation in a medium consisting of N-methyl-2-pyrrolidone (NMP)/triphenyl phosphite (TPP)/calcium chloride (CaCl 2 )/pyridine (py), and direct polycondensation in a tosyl chloride (TsCl)/pyridine (py)/N,N-dimethylformamide (DMF) system. The polymerization reaction produced a series of flame-retardant and thermally stable poly(amide-imide)s 5a-g with high yield. The resulted polymers were fully characterized by FTIR, 1 H NMR spectroscopy, elemental analyses, inherent viscosity, specific rotation and solubility tests. Data obtained by thermal analysis (TGA and DTG) revealed that the good thermal stability of these polymers. These polymers can be potentially utilized in flame retardant thermoplastic materials.

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“…But the contact angle must be 80 • or higher to be a hydrophobic surface. According to these results, we can say that only CPPG(50)-CBGPPO(50)-Si (20) has the highest value for phosphine oxide as well as enough Si content for it to be a hydrophobic-coating material.…”

Section: Surface Propertiesmentioning

confidence: 82%

Nonisocyanate polyurethane/silica hybrid coatings via a sol–gel route

Hoşgör¹,

Kayaman‐Apohan²,

Karataş³

et al. 2011

Adv Polym Technol

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Polyurethane/silica hybrids by a nonisocyanate route were prepared by reacting cyclic carbonate-modified bis(4-glycidyloxy phenyl)phenyl phosphine oxide (BGPPO), and poly(propyleneglycol)diglycidyl ether (PPG-DGE) with hexamethylene diamine. The incorporation of silica was achieved via a sol-gel method. The effect of silica and phosphine oxide moiety on polyurethane coating properties was studied by physical, mechanical, and thermal tests. Modulus and hardness of the coatings were enhanced by increasing the amount of silica and phosphine oxide based resin. The improvement in flame retardancy and thermal stability of nanocomposites was proved with increased char yield values and decomposition temperatures in thermogravimetric analyses. C 2011 Wiley Periodicals, Inc. Adv Polym Techn 00: 1-11, 2011; View this article online at wileyonlinelibrary.com.

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Novel flame‐retardant thermosets: Phosphine oxide‐containing diglycidylether as curing agent of phenolic novolac resins

Cited by 55 publications

References 16 publications

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Di(hydroperoxy)alkane Adducts of Phosphine Oxides: Safe, Solid, Stoichiometric, and Soluble Oxidizing Agents

Synthesis and properties of novel flame-retardant and thermally stable poly(amideimide) s fromN,N′-(bicyclo[2,2,2]oct-7-ene-tetracarboxylic)-bis-L-amino acids and phosphine oxide moiety by two different methods

Nonisocyanate polyurethane/silica hybrid coatings via a sol–gel route

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