Monomers for adhesive polymers, 2. Synthesis and radical polymerisation of hydrolytically stable acrylic phosphonic acids

Moszner, Norbert; Zeuner, Frank; Fischer, Urs; Rheinberger, Volker

doi:10.1002/(sici)1521-3935(19990501)200:5<1062::aid-macp1062>3.0.co;2-#

Cited by 72 publications

(71 citation statements)

References 6 publications

Supporting

Mentioning

Contrasting

Unclassified

Order By: Relevance

“…The reactions of bis(trimethylsilyl) phosphonates with alcohols leads to the corresponding phosphonic acid and alkoxytrimethylsilane [10] in a fast reaction. [11] Use of the trimethylsilyl esters thus allows generation of the phosphonic acid in situ, which may substitute some of the OiPr groups of Ti(OiPr) 4 . The (coordinated or noncoordinated) phosphonic acid could then react with 2-propanol, possibly catalyzed by Ti(OiPr) x moieties, [12] to produce water for condensation and the observed isopropyl monoester.…”

Section: Resultsmentioning

confidence: 99%

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

2013

View full text Add to dashboard Cite

The reaction of titanium isopropoxide, Ti(OiPr)4, with bis(trimethylsilyl) phosphonates has led to structures containingTi3O units [= Ti3(μ3‐O)(μ2‐OiPr)3(OiPr)3(O3PR)3] as the basic structural motif. This unit can be capped by a single Ti(OiPr)2L group (L = neutral ligand) through phosphonate bridges (for R = xylyl), or sandwich‐like structures can be formed with two Ti3O units bonded to a central Ti atom (for R = CH2CH2CH2Cl or benzyl). For R = allyl or ethyl, dimeric clusters were formed in which two Ti4 cluster units are bridged by isopropyl phosphonate ligands. For comparison, Ti(OiPr)4 was also treated with allylphosphonic acid to yield a Ti4 cluster. The reaction of Ti(OiPr)4 with the bulky bis(trimethylsilyl) 2‐naphthylmethyphosphonate did not yield an oxo cluster but instead the phosphonate‐substituted titanium alkoxide Ti4(OiPr)8(O3PCH2naphthyl)4.

show abstract

Section: Resultsmentioning

confidence: 99%

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

2013

View full text Add to dashboard Cite

show abstract

“…Further, it was found that a self-etching primer comprising 10-MDP provided efficient bonding of composite-type resin cement to titanium (Ti) 42) , while an adhesive primer containing 6-MHPA was found to exhibit strong adhesion to zirconia-and alumina-based all-ceramic prostheses 43) . On this note, hydrolytically stable adhesive monomers should be incorporated in single-bottle water-based self-etch primers or all-in-one adhesives [7][8][9][10][11][12][13] . In addition to phosphonic acid and flexible methylene chain moieties, it was suggested that a super-adhesive monomer should possess hydrolytically stable moieties in the molecular structure.…”

Section: Discussionmentioning

confidence: 99%

“…However, they formulated with ethyl alcohol, and did not show significant efficacy on bonding to the teeth 6) . Despite the lack of early success, recently synthesized phosphonic acid monomers appeared to be hydrolytically stable in self-etching primers or adhesives [7][8][9][10][11][12][13] and hence seemed promising. However, since these investigations [7][8][9][10][11][12][13] have not been extended beyond water-based adhesives, little is known about the multi-purpose bonding performance of phosphonic acid monomers with polymerization initiators in hydrophobic adhesive resins.…”

Section: Introductionmentioning

confidence: 99%

Multi-purpose Bonding Performance of Newly Synthesized Phosphonic Acid Monomers

et al. 2007

View full text Add to dashboard Cite

Multi-purpose bonding performance of three kinds of newly synthesized phosphonic acid monomers was investigated. Methacryloxyalkyl or acryloxyalkyl phosphonoacetates of 6-MHPA, 6-AHPA, 10-MDPA were synthesized in 42.8-51.9％ yields with a light yellow viscous liquid, and identified as new compounds by 1 H NMR, IR, and elemental analysis. Conventional adhesive monomers, namely VBPA, 4-META, and 4-AETA, and CEBA-p-TSMo-t-BPMA initiator were also used. Seven experimental composite-type adhesive resins comprising these six kinds of adhesive monomers and None (control) with the initiator were prepared. Tensile bond strengths of adhesive resins to unetched ground enamel and dentin, ground porcelain, and sandblasted Ni-Cr alloy were measured at a crosshead speed of 1.0 mm/min. Results showed that except with VBPA, there were no significant differences among 6-MHPA, 6-AHPA, 10-MDPA, 4-AETA, and 4-META in bonding performance to the adherends (p<0.01). It was found that the new phosphonic acid monomers provided good multipurpose adhesion to all adherends tested.

show abstract

“…Synthesis of monomers was described elsewhere. [24] The structure of Me-PAMA 18 is shown in Figure 1b.…”

Section: Methodsmentioning

confidence: 99%

Cationic Graft Copolymers as Carriers for Delivery of Antisense‐Oligonucleotides

Dautzenberg

Koňák

Reschel

et al. 2003

Macromolecular Bioscience

View full text Add to dashboard Cite

Self‐assembling systems based on ionic complexes of DNA fragments (36 base pairs), bcl‐2 antisense oligonucleotides (octadecamer), oligophosphates (25 phosphate groups) or acrylic oligomers (18 groups of phosphonic acid) with poly(L‐lysine) (PLL) ($\overline M _{\rm w}$ = 130 000 and 88 000) grafted with short poly[N‐(2‐hydroxypropyl)methacrylamide] (PHPMA) chains ($\overline M _{\rm n}$ = 4 300 or 8 600) were studied by static and dynamic light scattering methods as systems suitable for gene therapy applications. The graft copolymers (GPLLs) with shorter PHPMA grafts ($\overline M _{\rm n}$ = 4 300) provide polyelectrolyte complexes (PECs) with smaller $\overline M _{\rm w}$ and RH than the corresponding GPLLs with longer grafts ($\overline M _{\rm n}$ = 8 600) and the same content of PLL. The lowest aggregation number of 2 was observed for PECs prepared from the GPLL with short grafts and 40 wt.‐% of PLL. The complexes of oligonucleotides and DNA fragments with GPLLs showed quite similar behavior to that with oligophosphates and acrylic oligomer. The complexes prepared from GPLLs containing 40 wt.‐% of PLL and at excess of oligophosphate were stable for at least 48 h under physiological conditions (0.15 M NaCl) and in bovine serum albumin solutions (1 mg · mL−1). Additionally, polyanion exchange reactions of the PECs in contact with poly(styrenesulfonate) and DNA were studied in 0.15 M NaCl solutions. The oligophosphates in complexes were at least partially substituted with high‐molecular‐weight polyanions. The structure of the initial PECs dominated the PEC structure after the exchange reaction.The dependence of the molecular weight $\overline M _{\rm w}$ (a) and the hydrodynamic radius RH (b) of complexes of the oligophosphate (OPP) and four graft copolymers (GPLLi, i = 0–3) on the mixing ratio X.magnified imageThe dependence of the molecular weight $\overline M _{\rm w}$ (a) and the hydrodynamic radius RH (b) of complexes of the oligophosphate (OPP) and four graft copolymers (GPLLi, i = 0–3) on the mixing ratio X.

show abstract

Monomers for adhesive polymers, 2. Synthesis and radical polymerisation of hydrolytically stable acrylic phosphonic acids

Cited by 72 publications

References 6 publications

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

Influence of the Phosphonate Ligand on the Structure of Phosphonate‐Substituted Titanium Oxo Clusters

Multi-purpose Bonding Performance of Newly Synthesized Phosphonic Acid Monomers

Cationic Graft Copolymers as Carriers for Delivery of Antisense‐Oligonucleotides

Contact Info

Product

Resources

About