Acrylic Acid → Urethane acrylate

HRID 2259794Notes

Reaction equation

C[C@@]12[CH:10]([C:11]([C:13]([O-:15])=[O:14])=C)C[C@H](C1(C)C)CC2.C([O-])(=O)CCCCCCCCC[CH2:26][CH3:27].C([O-])(=O)CCCCCCCCCCC.C([Sn+2]CCCC)CCC.C(OCCO)(=O)C=C.[N-:61]=C=O.C(O)(=O)C=C.OC(C)(C)C(C1C=CC=CC=1)=O>C(OCC1OCCC1)(=O)C=C.C(O)C>[NH2:61][C:13]([O:15][CH2:26][CH3:27])=[O:14].[C:13]([OH:15])(=[O:14])[CH:11]=[CH2:10]

Participants

Conditions

Temperature: 80 °C

Procedure

An acrylate urethane oligomer composition was prepared in the following manner. A flask was charged with 202.8 g of PPG 1025 (polypropylene glycol with average molecular weight of 1025), 83.2 g of PPG 425 (polypropylene glycol with average molecular weight of 425), 221.6 g of isobornyl acrylate, 150.0 g of diphenylmethane 4,41 diisocyanate and 0.4 g of dibutyltin dilaurate. The mixture was heated at 80° C. for two hours. Hydroxyethyl acrylate, 23.2 g, was added and the heating continued for one hour. Ethanol, 9.7 g, was added and heating continued until the isocyanate band in the IR at 2268 cm-1 disappeared. The still warm product was diluted with 211.6 g of tetrahydrofurfuryl acrylate, 35.2 g acrylic acid and 35.2 g of Darocure 1173 initiator which is 2-hydroxy-2-methyl-1-phenyl-propane-1-one, a product of Ciba-Geigy. After thoroughly mixing, the mixture was poured warm into an opaque container. The yield of colorless product was 973 g with a viscosity of 8100 cP.

Workup

temperatureheating
additionAfter thoroughly mixing
additionthe mixture was poured
temperaturewarm into an opaque container

Sources & evidence

ORD record: ord-c4c9dd2e963747218d6ab6f32af6e9ea
Source dataset: uspto-grants-1995_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05475038

Reaction notes

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