Addition-fragmentation agent
A breaking agent, addition technology, used in dental formulations, organic chemistry, coatings, etc., can solve problems affecting the durability of cured compositions, adhesion failure, etc.
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example 1-9
[0105] Examples 1-9: Synthesis of Addition-Fragmentation Monomers (AFMs)
[0106] General procedure: All reactions were performed in round bottom flasks or jars or vials using unpurified commercial reagents.
[0107] Materials: Commercial reagents were used directly. Dichloromethane, ethyl acetate and toluene were obtained from EMD Chemicals Inc. (Gibbstown, NJ, USA) . Glycidyl methacrylate, 4-(dimethylamino)pyridine, methacryloyl chloride, triphenylphosphine, 2,6-di-tert-butyl-4-methylphenol and dibutyltin dilaurate were obtained from Alfa Aesar (Ward Hill, MA, USA) of Ward Hill, Massachusetts, USA. 2-Isocyanatoethyl methacrylate, 1,2-epoxy-3-phenoxypropane, and 1,2-epoxydecane were obtained from TCI Corporation, Portland, OR, USA (TCI America (Portland, OR, USA)). Acryloyl chloride, triethylamine and triphenylantimony were obtained from Sigma Aldrich (St. Louis, MO, USA). 4-Hydroxybutyl acrylate glycidyl ether was obtained from Nippon Kasei Chemical (Tokyo, Japan) in ...
example 1
[0119] Example 1: Preparation of AFM-1
[0120]
[0121]Into an approximately 250 mL amber bottle equipped with a magnetic stir bar was charged glycidyl methacrylate (23.0 mL, 24.8 g, 174 mmol) and triphenylantimony (0.369 g, 1.04 mmol). The reaction was covered with a plastic cap with two 16 gauge needles piercing the plastic cap to allow air into the reaction. With stirring, the mixture was heated to 100°C in an oil bath. Dibasic acid 1 (15.0 g, 87.1 mmol) was added to the reaction in small portions over 1.5 hours. After 21 hours, triphenylphosphine (0.091 g, 0.35 mmol) was added. The reaction was stirred continuously at 100°C. After an additional 6.5 hours the reaction was sampled and 1H NMR analysis was consistent with the desired product as a mixture of isomers with an indicated consumption of glycidyl methacrylate. The reaction was cooled to room temperature to afford AFM-1 as a clear, very pale yellow viscous material.
example 2
[0122] Example 2: Preparation of AFM-2 by diol 2
[0123]
[0124] Preparation of Diol 2
[0125] Charge 1,2-epoxy-3-phenoxypropane (3.93 mL, 4.36 g, 29.0 mmol) and triphenylantimony (0.0593 g, 0.168 mmol) into an approximately 30 mL glass vial equipped with a magnetic stir bar . The reaction was sealed with a plastic cap. With stirring, the mixture was heated to 100°C in an oil bath. Dibasic acid 1 (2.50 g, 14.5 mmol) was added to the reaction in small portions over 35 minutes. After 18 hours, triphenylphosphine (0.0162 g, 0.0618 mmol) was added. The reaction was stirred continuously at 100°C. After an additional 24 hours the reaction was sampled and1HNMR analysis was consistent with the desired product as a mixture of isomers. The reaction was cooled to room temperature to afford diol 2 as a clear, colorless glassy material.
[0126]
[0127] Preparation of AFM-2
[0128] A 100 mL round bottom flask equipped with a magnetic stir bar was charged with diol ...
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