3534-27-8Relevant academic research and scientific papers
Vibrational assignments of N,N-bis(3,5-dimethyl-2-hydroxybenzyl)methylamine in the fingerprint region
Dunkers, J.,Ishida, H.
, p. 855 - 868 (1995)
The compound N,N-bis(3,5-dimethyl-2-hydroxybenzyl)methylamine is synthesized to model the phenolic resulting from ring opening polymerization of benzoxazine monomers.Fundamental vibrational assignments of N,N-bis(3,5-dimethyl-2-hydroxybenzyl)methylamine a
Synthesis and Thermal Curing of Benzoxazine Functionalized Polyurethanes
Kirschbaum, Stefan,Landfester, Katharina,Taden, Andreas
, p. 3811 - 3816 (2015)
Benzoxazine (BOX) functionalized polyurethanes (PU) are introduced to provide a conceptually new thermal curing mechanism for polyurethanes. 3,4-Dihydro-3-methyl-2H-1,3-benzoxazine (P-m) was carefully oligomerized through thermal treatment. In a straightf
Tripodal O-N-O Bis-Phenolato Amine Titanium(IV) Complexes Show High in vitro Anti-Cancer Activity
Abid, Mohammed,Nouch, Ryan,Bradshaw, Tracey D.,Lewis, William,Woodward, Simon
supporting information, p. 2774 - 2780 (2019/06/13)
The octahedral titanium(IV) complexes trans,mer-[Ti{R3N(CH2C6H2-2-O-4-R2-6-R1)2}2] (R1 = Me, OMe, Cl; R2 = Me, OMe, F, Cl; R3 = Me, Et; not all combinations) are synthesised in two steps from simple phenols in 36–53 % overall yield. The highly crystalline (4 X-ray structures) complexes are active against MCF-7 (breast) and HCT-116 (colon) cancer cell lines showing widely varying GI50 values in the range 1–100 μM depending on R1–R3. Highest activities are realised when R1 = OMe and R2, R3 = Me (GI50 ca. 1 μM for MCF-7 and 2–3 μM for HCT-116). These are respectively 8× and 3× times greater than the activities of cisplatin in the same cell lines. These titanium complexes show some significant selectivity for cancer cell lines; up to 7× higher in MCF-7 compared to non-cancer (MRC-5) fibroblast cells. Details of cellular mode of action indicators (cell cycle perturbation, Annexin V, γ-H2AX, and caspase studies) that point to an apoptosis mode for the most active compound (R1 = OMe and R2, R3 = Me) are also reported.||||||.
Cationic ring-opening polymerization of 1,3-benzoxazines: Mechanistic study using model compounds
Chutayothin, Papinporn,Ishida, Hatsuo
experimental part, p. 4562 - 4572 (2011/10/18)
The benzoxazine monomer is used to simplify the study of the benzoxazine initiation mechanism. The HPLC retention time and the 1H NMR spectra of crude products from the benzoxazine reaction are compared with the results from a vast number of pure model compounds, which are synthesized based on the hypothesized mechanisms. Products involved in the process are identified, with species having benzoxazine structures, Mannich base and other components (acetal, nonacetal phenoxy structures, and methylene bridge structure). Initiation mechanisms of benzoxazine, e.g., the oxygen protonation and the nitrogen protonation, are proposed.
Self termination of ring opening reaction of p-substituted phenol-based benzoxazines: An obstructive effect via intramolecular hydrogen bond
Chirachanchai, Suwabun,Laobuthee, Apirat,Phongtamrug, Suttinun
experimental part, p. 714 - 721 (2009/12/01)
(Chemical Equation Presented) The ring opening polymerizations of p-substituted phenol-based benzoxazines are self-terminated as soon as dimers form. The polymerization of benzoxazine monomers does not proceed according to the theoretical mechanism even though the conditions, temperature, molar ratio, solvent polarity, and reactant ratio are varied. The speculated mechanism, involving the unique structure of a dimer with interand intramolecular hydrogen bonds, is applied to explain an obstructive effect on ring opening polymerization. In this article, we clarify an important case which the stereo structure of the compound controls the reaction and prevents the polymerization expected from the theoretical mechanism.
Selective crown ether based macrocyclization: a model case study from N,N-bis(2-hydroxyalkylbenzyl)alkylamine
Chirachanchai, Suwabun,Rungsimanon, Thitiporn,Phongtamrug, Suttinun,Miyata, Mikiji,Laobuthee, Apirat
experimental part, p. 5855 - 5861 (2009/12/01)
A model case of selective crown ether based macrocycles, i.e., [1+1] or [2+2] macrocycles, obtained from a simple reaction of N,N-bis(2-hydroxyalkylbenzyl)alkylamine, HBA, and ditosylated compounds is proposed. For HBA with the methyl group at ortho and p
A study on hydrogen-bonded network structure of polybenzoxazines
Kim, Ho-Dong,Ishida, Hatsuo
, p. 3271 - 3280 (2007/10/03)
The hydrogen-bonded network structure for polybenzoxazines is investigated by Fourier Transform Infrared Spectroscopy (FT-IR) with model dimer systems. Comparing the FT-IR spectra of the polybenzoxazines and model dimers, it is shown that the simpler structures of asymmetric dimers well simulate the hydrogen-bonded network structure between polymer chains while the structures of symmetric dimers reflect the hydrogen bonding scheme related to the end-groups of polymer chains. It is confirmed that the amine functional group in the Mannich bridge is greatly responsible for the distribution of hydrogen bonding species. Bisphenol A/methylamine-based polymer (BA-m) mainly consists of -OH...N intramolecular hydrogen bonding while bisphenol A/aniline-based polymer (BA-a) has a large amount of intermolecular hydrogen bonding and relatively weak hydrogen bonding groups in the polymer network structure. The possible network structure, in the sense of hydrogen bonding, for BA-m and BA-a polymers is proposed and a generalized explanation for the structure-property relationships in polybenzoxazines is also discussed.
