Highly reactive, liquid diacrylamides via synergistic combination of spatially arranged curing moieties

• Maximilian Maier,
• Magnus S. Schmidt,
• Markus Ringwald and
• Christoph P. Fik

Beilstein J. Org. Chem. 2017, 13, 372–383, doi:10.3762/bjoc.13.40

• % camphorquinone, 0.4 wt % ethyl 4-dimethylaminobenzoate and irradiated twice. After the first run a second run was made that was subtracted from the first one. The subtraction of these runs from one another removed the effect of sample heating by illumination. The DSC experiments were carried out twice and

• heat released per mole of double bonds reacted, and m the mass of the monomer in the sample. Mechanical data was measured in the 3-point bending mode according to ISO 4049:2009 using a Zwick instrument. Sample activation was done by adding 0.3 wt % camphorquinone and 0.4 wt % ethyl 4

Strecker degradation of amino acids promoted by a camphor-derived sulfonamide

• M. Fernanda N. N. Carvalho,
• M. João Ferreira,
• Ana S. O. Knittel,
• Maria da Conceição Oliveira,
• João Costa Pessoa,
• Rudolf Herrmann and
• Gabriele Wagner

Beilstein J. Org. Chem. 2016, 12, 732–744, doi:10.3762/bjoc.12.73

• unusual redox reactions [11][12][13][14]. Since camphorquinone (Figure 1) is known to react with amines through the C=O group (position 3, Figure 1) forming imine camphor compounds [2][15][16][17], one could expect that an amine condensation with the C=O double bond of oxoimine 1 would also lead to imine

• 1 proceeds rapidly under mild conditions. The only other camphor derivative found to promote the Strecker degradation is camphorquinone [27] (Figure 1), no Strecker degradation is observed with camphor itself. For imines obtained from reaction of amino acids with ninhydrin, a mechanism of the

Synthesis of a resin monomer-soluble polyrotaxane crosslinker containing cleavable end groups

• Ji-Hun Seo,
• Shino Nakagawa,
• Koichiro Hirata and
• Nobuhiko Yui

Beilstein J. Org. Chem. 2014, 10, 2623–2629, doi:10.3762/bjoc.10.274

• solution. In any event, it could be confirmed that C12-Bu12-MA12 is completely degraded by the cleavage of the disulfide end groups, and a large number of α-CD molecules are released. Synthesized C12-Bu12-MA12 was then polymerized with HEMA and UDMA via camphorquinone-initiated polymerization. Figure 4

• potentially be utilized in the industrial or biomedical field. Experimental Materials A PRX containing 50 α-CDs with disulfide end groups was synthesized by using PEG 10k as previously reported in [11]. n-Butylamine and camphorquinone were purchased from Tokyo Kasei Co. (Tokyo, Japan). 2-Aminoethyl

• crosslinker (50 wt % C12-Bu12-MA12 PRX and 25 wt % UDMA) with 5 wt % (to total monomer mixture) of initiator mixture (camphorquinone 2 wt %, CMBE 2 wt %, BHT 1 wt %) was dissolved in 200 wt % acetone and cast in a 8 mm in diameter and 0.5 mm deep disk-type Teflon assembly mold and dried by air blowing. The

Synthesis and photooxidation of styrene copolymer bearing camphorquinone pendant groups

• Branislav Husár,
• Norbert Moszner and
• Ivan Lukáč

Beilstein J. Org. Chem. 2012, 8, 337–343, doi:10.3762/bjoc.8.37

• groups on the polymer backbone. An equivalent irradiation of MCQ/S led mainly to the insertion of only one oxygen atom between the carbonyl groups of camphorquinone (CQ) and to the formation of camphoric anhydride (11) covalently bound to the polymer backbone. While the decomposition of pendant BP groups

• formed in irradiated films of styrene copolymers with pendant BZ groups leads to crosslinking, only small molecular-weight changes in irradiated MCQ/S were observed. Keywords: camphorquinone; 1,2-diketone; (±)-10-methacryloyloxycamphorquinone; photooxidation; polystyrene; Introduction Camphorquinone

Novel 2-(ω-phosphonooxy-2-oxaalkyl)acrylate monomers for self-etching self-priming one part adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2010, 6, 766–772, doi:10.3762/bjoc.6.95

• ), 168.5 (CO). 31P NMR (CD3OD; ppm): −0.11/0.07 (d, PO3H2). Adhesive composition 4a: 1.5261 g N,N´-bisacrylamido-1,3-propane, 2.2150 g 3,(4),8,(9)-bis(acrylamidomethyl)tricyclo[5.2.1.02,6]decane, 0.5551 g of 3a, 0.2776 g 2-acrylamido-2-methylpropanesulfonic acid, 0.0337 g camphorquinone, 0.0849 g bis(2,4,6

• conditions. The subtraction of these runs from one another removed the effect of different baselines for the dark and the illumination periods. In the monomers were dissolved 0.3 mol % camphorquinone and 0.35 mol % 4-(N,N-dimethylamino)benzoic acid ethyl ester. Adhesion of an adhesive composition 4

Synthesis of bis(3-{[2-(allyloxy)ethoxy]methyl}-2,4,6-trimethylbenzoyl)(phenyl)phosphine oxide – a tailor-made photoinitiator for dental adhesives

• Norbert Moszner,
• Iris Lamparth,
• Jörg Angermann,
• Urs Karl Fischer,
• Frank Zeuner,
• Thorsten Bock,
• Robert Liska and
• Volker Rheinberger

Beilstein J. Org. Chem. 2010, 6, No. 26, doi:10.3762/bjoc.6.26

• -butyl]acrylate [3] or 1,3-bis(methacrylamido)propane-2-yl dihydrogen phosphate (BMAMHP) [4], which show improved hydrolytic stability under acidic aqueous conditions. The visible-light (VL) photoinitiators (PIs) in current SEAs are based on mixtures of camphorquinone (CQ) and tertiary amines (A) [5

• acid by chloromethylation according to the literature [15]. DBDEG was synthesized as described previously [18]. DL-camphorquinone (CQ, Rahn, Switzerland), ethyl p-dimethylaminobenzoate (EMBO, Fluka Chemie AG, Switzerland) and Irgacure® 819 (BAPO, Ciba Specialty Chemical, Switzerland) were used without

N-alkyl-N-(phosphonoethyl) substituted (meth)acrylamides – new adhesive monomers for self-etching self-priming one part dental adhesive

• Joachim E. Klee and
• Uwe Lehmann

Beilstein J. Org. Chem. 2009, 5, No. 72, doi:10.3762/bjoc.5.72

• , trimethylbromosilane, butylamine, 3,6-dioxaoctane-1,8-diamine, camphorquinone and 4-(N,N-dimethylamino)benzoic acid ethyl ester, diethyl (hydroxymethyl)phosphonate, 2,2′-azobisisobutyronitrile (AIBN) and 2,6-di-tert-butyl-4-methylphenol were purchased from Sigma-Aldrich and phenylbis(2,4,6-trimethylbenzoyl)phosphine

• mol % camphorquinone and 0.35 mol % 4-(N,N-dimethylamino)benzoic acid ethyl ester. The hydrolytic stability was studied by detection of acrylic or methacrylic acid in HPLC using solutions of 1.5 mmol of 3c, 3d and 3e and solutions of 0.6 mmol 3g in 5 mL of a 1:1 mixture of distilled water and ethanol

• which were stored at 50 °C. The adhesion on enamel and dentin of phosphonic acids 3 was tested using the following formulation: 0.2499 g N,N′-diethyl-1,3-bis(acrylamido)propane, 0.3000 g phosphonic acid 3, 0.4168 g 3(4),8(9)-bis(acrylamidomethyl)tricyclo[5.2.1.02,6]decane, 0.0071 g camphorquinone