Photopolymerization of 1,6-hexanediol diacrylate: The effect of functionalized amines

Hoyle, Charles E.; Keel, Monty; Kim, Kyu‐Jun

doi:10.1016/0032-3861(88)90194-2

Cited by 50 publications

(17 citation statements)

References 4 publications

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“…Numerous dyes were reported as PS [9,27–32]. Hydrogen donor coinitiators could be amines [33–38], ethers [39–40], sulfides [41–43] or thiols [43–45]. Electron transfer coinitiators could be borate salts [46–47], iodonium [48–49] or triazine [32] derivatives.…”

Section: Introductionmentioning

confidence: 99%

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

Ley¹,

Christmann²,

Ibrahim³

et al. 2014

Beilstein J. Org. Chem.

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SummaryThe combination of a dye which absorbs the photon, an electron acceptor and an electron donor leading to energy conversion through electron transfer, was the basis of the so called three-component systems. In this paper, an experimental work combining Rose bengal dye with a triazine derivative as electron acceptor and ethyl 4-(dimethylamino)benzoate as electron donor, will underline the benefit of the photocyclic behavior of three-component systems leading to the dye regeneration. A thermodynamic approach of the photocycle is presented, followed by a mechanistic and computational study of ideal photocycles, in order to outline the specific kinetics occuring in so called photocatalytic systems. The simple kinetic model used is enough to outline the benefit of the cyclic system and to give the basic requirements in term of chemical combination needed to be fulfilled in order to obtain a photocatalytic behavior.

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Section: Introductionmentioning

confidence: 99%

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

Ley¹,

Christmann²,

Ibrahim³

et al. 2014

Beilstein J. Org. Chem.

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“…[27] Interestingly, two monosubstituted tertamine compounds, DMABPA-1M and DMABPA-1A exhibited double doublet (dd) proton peaks at the corresponding positions because they have two isomers each. The DMA-benzoate and BPA groups in DMABPAwere furthermore confirmed by 13 C NMR spectra at 39.9 ppm for amino methyl, and 110.7, 116.1, 131.5, and 153.5 ppm for benzoate and BPA groups. [14] Characteristic FTIR absorption bands appeared at 3 400 cm À1 (OH), 1 687 cm À1 (C O), 1 280 and 1 180 cm À1 (C-O), corresponding to the DMABPA structure.…”

Section: Synthesis Of Bpa-based Tert-aminesmentioning

confidence: 66%

“…The structures of BPA-based tert-amine compounds were confirmed with 1 H NMR, 13 C NMR, and FTIR spectra, and elemental analysis. The proton NMR spectrum of DMABPA confirmed the DMA-benzoate group with a singlet peak of the DMA protons and two doublet peaks of aromatic protons at 3.04 and 7.27 ppm, respectively, and the skeletal BPA structure was matched with the known Bis-GMA structure.…”

Section: Synthesis Of Bpa-based Tert-aminesmentioning

confidence: 84%

“…Such monomers are p-(N,N-dimethylamino)styrene, [11] p-(N,N-dimethylamino)benzyl methacrylate, [12] and N,N-dimethylaminoethyl methacrylate (DMAEMA), [13,14] and these were applied along with aromatic carbonyls as polymerizable PIs. In practice, a visible light photoinitiator consisting of CQ and ethyl p-(N,N-dimethylamino)benzoate (EDMAB) as the tert-amine is used in commercial dental resin formulations.…”

Section: Introductionmentioning

confidence: 99%

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New Aromatic tert‐Amines for Application as Photoinitiator Components in Photocurable Dental Materials

Ahn

Han

Lee

et al. 2003

Macro Chemistry & Physics

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A new type of aromatic tert‐amine with a bisphenol A (BPA) skeleton has been prepared and applied as a photoinitiator (PI) component for enhancing photosensitivity in formulations of visible light curable dental polymers. Two N,N‐dimethylamino (DMA) groups were incorporated into BPA diglycidyl ether to make 2,2‐bis[4‐(2‐hydroxy‐3‐(p‐N,N‐dimethylaminobenzoyloxy)propyloxy)phenyl]propane (DMABPA). One or two (meth)acryloyl groups were reacted with the hydroxyl groups of DMABPA to obtain the polymerizable, BPA‐based tert‐amines DMABPA‐1M (one methacrylate), DMABPA‐2M (two methacrylates), and DMABPA‐1A (one acrylate). The aromatic tert‐amines and ethyl p‐(N,N‐dimethylamino)benzoate (EDMAB) were combined with a camphorquinone sensitizer to form a photoinitiating system, which was applied in photopolymerizations of dental resin formulations, based on Bis‐GMA as a matrix prepolymer, by visible light exposure. The photoconversion of the formulations using the new aromatic tert‐amines as PIs was determined by the spectral changes in FTIR absorption intensities of methacrylate groups in cast films. High conversion (over 70%) resulted from photopolymerizations with (meth)acrylated DMABPA‐(1M, 2M, and 1A).magnified image

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“…This may be addressed to chain transfer reactions involving Photoinitiation Activity Experiments the tertiary amino groups of the monomers. 21 Indeed, the a-alkylamino radicals thus generated HDDA/BA equimolar mixtures containing 0.3 usually have a lower reinitiation rate constant mol % of a-aminoacetophenone moieties were as compared with the propagation process, 21 thus cured on film matrix (300 mm) at 25ЊC under nitroimplying a lowering of the overall polymerization gen, by irradiation with a high-pressure 100W rate and hence of the conversion to polymer. This OSRAM HBO Hg lamp.…”

Section: Introductionmentioning

confidence: 99%

Novel polymeric photoinitiators bearing side-chain ?-aminoacetophenone moieties for ultraviolet-curable pigmented coatings

Carlini

Angiolini

Caretti

et al. 1997

J. Appl. Polym. Sci.

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New polymeric photoinitiators with pendant a-aminoacetophenone moieties, such as the homopolymers of 1-(4-morpholinophenyl)-2-benzyl-2- [N-methyl-N-(3-methacryloyloxypropyl)]aminopropan-1-one and of 1-(4-morpholinophenyl)-2-benzyl-2-[N-methyl-N-(3-methacryloyloxypropyl)]aminobutan-1-one have been prepared and fully characterized. Their photoinitiation activity has been also checked in the ultraviolet cure of a standard acrylic mixture, under irradiation over 380 nm, thus simulating the absorption conditions of a TiO 2 -pigmented coating formulation. The results have been compared with those found by using the corresponding low-molecularweight structural models, purposely synthesized. The activity data obtained are discussed and related to the structural requirements of the above systems.

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Photopolymerization of 1,6-hexanediol diacrylate: The effect of functionalized amines

Cited by 50 publications

References 4 publications

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

Tailoring of organic dyes with oxidoreductive compounds to obtain photocyclic radical generator systems exhibiting photocatalytic behavior

New Aromatic tert‐Amines for Application as Photoinitiator Components in Photocurable Dental Materials

Novel polymeric photoinitiators bearing side-chain ?-aminoacetophenone moieties for ultraviolet-curable pigmented coatings

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