Hydroquinone → Urethane acrylate

HRID 1262625Notes

Reaction equation

HRID 1262625 reaction equation
C1(C=[CH:7][C:5]([OH:6])=CC=1)O.[C:9]([O-:13])(=[O:12])[CH:10]=[CH2:11].CC(C(OCCO)=O)=C.[N-:23]=[C:24]=[O:25]>[Sn].C(O)CCC>[C:9]([OH:13])(=[O:12])[CH:10]=[CH2:11].[NH2:23][C:24]([O:6][CH2:5][CH3:7])=[O:25]

Participants

7

Reactant 4

HCID 785HydroquinoneHCID 133602-Hydroxyethyl MethacrylateHCID 25188AcrylateHCID 105034Isocyanate2×

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 2

HCID 5352426Tin atomCatalystHCID 2631-ButanolSolvent

Procedure

First 700 parts of 535 molecule weight, polyhexyl orthophthalate were added to a glass resin kettle. A heating mantel was used to supply heat. The pot was also fitted with a thermometer and motorized stirrer. While stirring, the polyol was heated to 162° F. (72° C.) to degass at which temperature, 570 parts of isophorone diisocyanate (IPDI) were added. The temperature dropped to 130° F. (54° C.), but after 10 minutes began to rise again. Ten minutes later the material had exothermed to a peak temperature of 260° F. (127° C.) The prepolymer was allowed to react fully for 45 minutes with continuous stirring without heating. Two parts of hydroquinone were added next to stabilize the acrylate to be added in the subsequent phase of the reaction. The prepolymer was cooled further to 160° F. (71° C.) at which temperature, 367 parts of HEMA were added to completely react with the theoretical amount of free isocyanate available from the prepolymer. The temperature dropped to 150° F. (66° C.). A tin catalyst (T832) was added to the stirred material in the amount of 64 drops, the material exothermed to a peak temperature of 184° F. (84° C.) in 5 minutes. The material was then cooled to room temperature. After the acrylated urethane was allowed to sit at room temperature for 18 hours, an analysis for any residual amount of isocyanate was made. The % free NCO was 0.11. Four grams of butanol (a slight excess) were added to the reheated material to quench the remaining NCO groups. The viscous liquid was then poured into two glass quart jars which were then sealed.

Workup

  1. temperatureto supply heat
  2. customThe pot was also fitted with a thermometer
  3. customto degass at which temperature, 570 parts of isophorone diisocyanate (IPDI)
  4. additionwere added
  5. additionThe temperature dropped to 130° F. (54° C.)
  6. customTen minutes
  7. customhad exothermed to a peak temperature of 260° F. (127° C.)
  8. customto react fully for 45 minutes
  9. stirringwith continuous stirring
  10. temperaturewithout heating
  11. additionto be added in the subsequent phase of the reaction
  12. additionwere added
  13. additionThe temperature dropped to 150° F. (66° C.)
  14. waitthe material exothermed to a peak temperature of 184° F. (84° C.) in 5 minutes
  15. waitto sit at room temperature for 18 hours
  16. customto quench the remaining NCO groups
  17. additionThe viscous liquid was then poured into two glass quart jars which
  18. customwere then sealed

Sources & evidence

ORD record
ord-df838826484645b18abd8bc010c13192
Source dataset
uspto-grants-1984_06
Patent number
US04452964

Reaction notes

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