Polymeric photoinitiators bearing side‐chain benzoyldiphenylphosphinoxide moieties for UV curable coatings

Angiolini, Luigi; Caretti, Daniele; Carlini, Carlo; Lelli, Nicola; Rolla, Pierangelo

doi:10.1002/app.1994.070510114

Cited by 8 publications

(3 citation statements)

References 25 publications

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“…21). On photoinitiation activity, poly(VBPO-co-MMA)s exhibited markedly improved activity than analogous aliphatic polymeric systems bearing the acylphosphine oxide moiety in the side chain 54) . On stability to daylight, poly(ADBPO-co-BA) exhibited appreciably higher stability than TMDPO, which is reported to be the most stable commercial member of this class of photoinitiators 55) .…”

Section: Synthesis and Kinetics Of Polymeric Photoinitiators Bearing mentioning

confidence: 98%

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A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

2010

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This paper reviews our recent studies on radical photopolymerization initiators, which are used in the design of light-curing dental adhesives and resin composites, by collating information of related studies from original scientific papers, reviews, and patent literature. The photopolymerization reactivities of acylphosphine oxide (APO) and bisacylphosphine oxide (BAPO) derivatives, and D,L-camphorquinone (CQ)/tertiary amine were investigated, and no significant differences in degree of conversion (DC) were found between BAPO and CQ/amine system (p>0.05). In addition, a novel 7,7-dimethyl-2,3-dioxobicyclo[2.2.1]heptane-1-carbonyldiphenyl phosphine oxide (DOHC-DPPO=CQ-APO) was synthesized and its ultraviolet and visible (UV-VIS) spectral behavior was investigated. CQ-APO possessed two maximum absorption wavelengths (λmax) at 350-500 nm [372 nm (from APO group) and 475 nm (from CQ moiety)], and CQ-APO-containing resins exhibited good photopolymerization reactivity, excellent color tone, relaxed operation time, and high mechanical strength. It was also found that a newly synthesized, water-soluble photoinitiator (APO-Na) improved adhesion to ground dentin.

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Section: Synthesis and Kinetics Of Polymeric Photoinitiators Bearing mentioning

confidence: 98%

“…20 Structural formula of a polymeric photoinitiator bearing side-chain benzoyl diphenylphosphine oxide moieties and its α-cleavage photoinitiation 54) . Full names of poly(VBPO) and poly(VBPO-co-MMA) are given in Table 1.…”

Section: Synthesis and Kinetics Of Polymeric Photoinitiators Bearing mentioning

confidence: 99%

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

2010

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“…Angiolini et al linked acyl phosphine oxides to polymers successfully. , Polymeric photoinitiators were prepared by reacting homopolymers or copolymers of 4-acryloyl benzoic acid or 4-acryloyl-2,6-dimethyl benzoic acid with thionyl chloride followed by methoxydiphenylphosphine. By linking the acylphosphine oxide at the benzoyl side to the polymer, the more reactive phosphinoyl radical can initiate the polymerization.…”

Section: Introductionmentioning

confidence: 99%

Hydrophilic Polymeric Acylphospine Oxide Photoinitiators/Crosslinkers for in Vivo Blue-Light Photopolymerization

Jh¹,

K²,

Deuring³

et al. 2001

Biomacromolecules

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Three vinyl-functionalized phosphine oxide photoinitiating monomers have been synthesized: 4-vinylbenzoyldiphenylphosphine oxide (VBPO), 2,6-dimethyl-4-vinylbenzoyldiphenylphosphine oxide (DMVBPO), and 2,4,6-trimethylbenzoylphenyl-4-vinylphenylphosphine oxide (TMBVPO). VBPO was copolymerized with vinylpyrrolidone or vinyl acetate (PPI-1a) and dimethylacrylamide (PPI-1b). DMVBPO and TMBVPO were both copolymerized with dimethylacrylamide (PPI-2 and PPI-3, respectively). The choice of vinylphosphine oxide and comonomer(s) had a significant influence on the properties of the resulting PPI. PPI-1a was not stable in solution in 2-hydroxyethyl methacrylate (HEMA), whereas the VBPO-dimethylacrylamide (DMA) copolymer (PPI-1b) was stable in HEMA but not stable in aqueous solutions. PPI-2 was both soluble and stable in water up to 22 months. PPI-1a was as effective as trimethylbenzoyldiphenylphosphine oxide (TPO, BASF Lucirin). PPI-2 was more effective in the polymerization of HEMA/water mixtures than PPI-3. PPI-2 and PPI-3 acted as self-cross-linking species, resulting in the formation of hydrogels; PPI 3 was more effective in this. PPI-2 was very effective in forming hydrogels based on poly(ethylene glycol) diacrylate.

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Polymeric systems bearing side‐chain 2,6‐dimethylbenzoyldiphenylphosphinoxide moieties for UV curable coatings: Synthesis and photoinitiation activity

Angiolini¹,

Caretti²,

Carlini³

1995

J of Applied Polymer Sci

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SYNOPSISPolymeric photoinitiators with pendant 2,6-dimethylbenzoyldiphenylphosphinoxide moieties were prepared by reacting the homopolymer of 4-acryloyloxy-2,6-dimethyl benzoic acid, and its copolymers with n-butyl acrylate with thionyl chloride followed by methoxydiphenylphosphine. These polymeric systems were characterized and their photoinitiation activity checked in the UV curing of a standard acrylic mixture, by irradiation both a t 330 and over 380 nm, the latter conditions being applied to simulate a Ti0,-pigmented coating formulation. The results were compared with those obtained by using the low molecular weight analog 2,4,6-trimethylbenzoyldiphenylphosphinoxide and previously prepared polymeric systems based on the benzoyldiphenylphosphinoxide moiety. The stability to light and to hydrolytic conditions of the polymeric photoinitiators with respect to the model compound was also tested. The results obtained are discussed and related to the structural requirements of these systems. 0 1995 John Wiley & Sons, Inc.

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Polymeric photoinitiators bearing side‐chain benzoyldiphenylphosphinoxide moieties for UV curable coatings

Cited by 8 publications

References 25 publications

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

A review of the development of radical photopolymerization initiators used for designing light-curing dental adhesives and resin composites

Hydrophilic Polymeric Acylphospine Oxide Photoinitiators/Crosslinkers for in Vivo Blue-Light Photopolymerization

Polymeric systems bearing side‐chain 2,6‐dimethylbenzoyldiphenylphosphinoxide moieties for UV curable coatings: Synthesis and photoinitiation activity

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