Ethylene Oxide → Urethane acrylate

HRID 1439980Notes

Reaction equation

HRID 1439980 reaction equation
CC1C(N=C=O)=CC([N:8]=[C:9]=[O:10])=CC=1.C([C:18]1C=C(C)C=C(C(C)(C)C)[C:19]=1[OH:29])(C)(C)C.OCC[O:33][C:34](=[O:37])[CH:35]=[CH2:36].C1OC1.C1OC1CC>>[C:34]([OH:37])(=[O:33])[CH:35]=[CH2:36].[NH2:8][C:9]([O:29][CH2:19][CH3:18])=[O:10]

Participants

6

Reactant 5

HCID 6354Ethylene OxideHCID 78341,2-EpoxybutaneHCID 11443Toluene 2,4-DiisocyanateHCID 131652-Hydroxyethyl acrylateHCID 314042,6-Di-tert-butyl-4-methylphenol

Product 1

HCID 21863578Urethane acrylate

Procedure

To a reaction vessel equipped with a stirrer, 233.1 gm of 2,4-tolylene diisocyanate, 1 gm of dibutyltindilaurate, and 0.3 gm of 2,6-di-t-butyl-4-methylphenol as a polymerization inhibitor was added. To this, 250.6 gm of 2-hydroxyethylacrylate was added while controlling the temperature to 20° C. or less. After the addition was completed the mixture was continuously stirred for an additional one hour at 10° to 20° C. Following this, 516.8 gm of a copolymerized diol of ethylene oxide and 1,2-butylene oxide [ethylene oxide:1,2-butylene oxide =1:9 (by weight)] of a number average molecular weight of 2,000 was added while maintaining the temperature in the 40° to 50° C. range, after which the mixture was continuously stirred for 5 hours at 50° to 60° C. to complete the reaction. A urethane acrylate [A-4] of a number of average molecular weight of about 1,850 was obtained.

Workup

  1. customTo a reaction vessel equipped with a stirrer
  2. customto 20° C. or less
  3. additionAfter the addition
  4. additionwas added
  5. temperaturewhile maintaining the temperature in the 40° to 50° C. range
  6. stirringafter which the mixture was continuously stirred for 5 hours at 50° to 60° C.
  7. customthe reaction

Sources & evidence

ORD record
ord-bb1f6c118357423ba905e0f117f42ed9
Source dataset
uspto-grants-1996_03
Patent number
US05496870

Reaction notes

Loading…