Ammonia → 2-(Acetoacetoxy)ethyl methacrylate

HRID 487667

Reaction equation

HRID 487667 reaction equation
N.[CH2:2](O)[CH:3]([OH:5])[CH3:4].CC(C(O)[C:11]([CH2:14][O:15][C:16]([CH:18]([CH3:20])[CH3:19])=[O:17])(C)C)C.N[C:23]([O:25]CC)=[O:24]>C(C(C)=O)C>[CH3:20][C:18]([C:16]([O:15][CH2:14][CH2:11][O:25][C:23]([CH2:2][C:3]([CH3:4])=[O:5])=[O:24])=[O:17])=[CH2:19]

Participants

6

Reactant 4

HCID 222Ammonia2×HCID 1030Propylene GlycolHCID 5641Carbamic acid, ethyl esterHCID 6490Texanol

Product 1

HCID 888552-(Acetoacetoxy)ethyl methacrylate

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Procedure

A 100 g. portion of each polymer was neutralized to pH=9.5 with ammonia, an additional 0.52 g. of ammonia was added (one equivalent based on acetoacetate) to ensure complete enamine formation. To all three samples was added a premix consisting of 0.32 g. nonionic surfactant (Triton X-405; Union Carbide, 4.4 g. propylene glycol, 4.4 g. coalescent (Texanol) and 1.1 g. a 10% aqueous solution of urethane rheology modifier (QR-708; Rohm and Haas). The formulated mixture was equilibrated for 24 hours and then coatings were applied on glass plates to give 3-4 mil thick coatings. Films were placed outdoors in complete sunlight for 12 days. Film swell ratios in methyl ethyl ketone were obtained.

Workup

  1. additionTo all three samples was added a premix
  2. customto give 3-4 mil thick coatings
  3. customfor 12 days

Sources & evidence

ORD record
ord-d26d0372baff4709807069e29e65f9e2
Source dataset
uspto-grants-1994_03
Patent number
US05296530

Linked notes

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