Reaktion #641244

ord-40762ffc358245eabd6dd48c30a9c1a1

Reaktionsgleichung

C=CC/C=C\C/C=C\CCCCCCCc1cccc(O)c1
cardanol
C=CC/C=C\C/C=C\CCCCCCCc1cccc(O)c1
Cardanol
O=C([O-])[O-].[K+].[K+]
K2CO3
O=C=NCCCCCCN=C=O
Hexamethylene diisocyanate
C=C(C)C(=O)OCCO
HEMA
OCCCl
2-chloroethanol
C=C(C)C(=O)OCCO.C=CC/C=C\C/C=C\CCCCCCCc1cccc(O)c1.O=C=NCCCCCCN=C=O
Cardanol HMDI HEMA
Ausbeute 62.0%

Lösungsmittel

Reaktionsbedingungen

Temperatur
50°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    Temperaturthe contents were cooled with ice
  2. 2
    Sonstigefor 2 hr
  3. 3
    workup.ADDITIONwas added as catalyst
  4. 4
    workup.WAITIt was left
  5. 5
    workup.STIRRINGstirring under cold condition for a further 1 hr
  6. 6
    Sonstigeto attain room temperature
  7. 7
    Extraktionextracted with dichloromethane
  8. 8
    WaschenIt was then washed with plenty of water
  9. 9
    Sonstigedried in vacuum oven at 60° C. for 12 hrs
  10. 10
    Sonstigeto obtain the final UV curable telechelic pre polymer with varying R1, R2, R3, R4, R5 and R6

Vorschrift

Cardanol was modified by coupling it with 2-chloroethanol in presence of K2CO3 and KI in DMF under inert atmosphere. Hexamethylene diisocyanate [HMDI] (0.49 g, 0.003 moles) in 10 ml dry DMF was taken in a 100 ml two necked flask and the contents were cooled with ice. HEMA (0.38 g, 0.003 moles) was added drop wise with constant stirring under nitrogen. The reaction was allowed to proceed under ice cold condition for 2 hr. Then the reaction was kept at room temperature for 1 hr. After that the reaction was changed to ice cold condition and 3 drops of DBTDL was added as catalyst followed by drop wise addition of modified cardanol (1 g, 0.003 moles) in 10 ml DMF. It was left stirring under cold condition for a further 1 hr and allowed to attain room temperature. Then the reaction was heated to 50° C. for 12 hrs. The contents were poured to 150 ml water and extracted with dichloromethane. It was then washed with plenty of water and dried in vacuum oven at 60° C. for 12 hrs. Yield=62% (1.17 g). The same synthetic procedure is adopted for all types of variation in the diisocyanate chemistry or in the hydroxy(meth)acryloxy chemistry or natural resource with active hydrogen atom to obtain the final UV curable telechelic pre polymer with varying R1, R2, R3, R4, R5 and R6.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08048979B2uspto-grants-2011_11