Carbamic acid, ethyl ester → Sebacic Acid
Reaction equation
[N-]=[C:2]=O.N[C:5]([O:7][CH2:8][CH3:9])=[O:6].[CH3:10][CH:11]([C:18]([O-:20])=[O:19])[CH2:12][C@@H:13]([C:15]([O-])=O)N.C(N([CH2:26][CH3:27])CC)C.CN(C)[CH:30]=[O:31].[O:33]1CCOCC1>>[C:18]([OH:20])(=[O:19])[C:11]1[CH:12]=[CH:13][C:15]([C:5]([OH:7])=[O:6])=[CH:2][CH:10]=1.[C:30]([OH:31])(=[O:33])[CH2:8][CH2:9][CH2:26][CH2:27][CH2:15][CH2:13][CH2:12][CH2:11][C:18]([OH:20])=[O:19]Participants
Procedure
A 985 g quantity of polytetramethylene glycol (OH value: 56.9) and 222 g of isophorone diisocyanate were reacted at 110° C. for 5 hours to obtain a urethane prepolymer (NCO equivalent: 1233) having an isocyanate ending. A 93.5 g quantity of the urethane prepolymer and 76.5 g of γ-methyl-L-glutamate NCA were dissolved in 666 g of solvent mixture of dimethylformamide/dioxane (7/3 in weight ratio), and 45 g of 2% triethylamine solution was added to the solution with stirring. The mixture was reacted at 30° C. for 5 hours, giving a satisfactorily fluid, yellowish brown, milky and turbid solution of PAU resin Y having a viscosity of 42,000 cps (25° C.) The PAU resin Y was used for Formulations 8 to 12 given later. On the other hand, a polyester resin Z was prepared which had a molecular weight of 30,000 and produced from a mixture of terephthalic acid and sebacic acid in a molar ratio of 6:4 and a mixture of ethylene glycol and neopentyl glycol in a molar ratio of 5:5 by copolymerization. The resin Z was used for Formulation 8 stated below.
Workup
- additionwas added to the solution
- customThe mixture was reacted at 30° C. for 5 hours
- customgiving a satisfactorily fluid
- customa viscosity of 42,000 cps (25° C.)
Sources & evidence
- ORD record
- ord-cf16f8950ebc45e4945d94ae8f12c661
- Source dataset
- uspto-grants-1987_01
- Patent number
- US04636424
Reaction notes
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