Methacrylic Acid → Urethane acrylate

HRID 2099602Notes

Reaction equation

HRID 2099602 reaction equation
C=C[C:3]1[CH:8]=CC=CC=1.[C:9]([O:14]CCCCCC)(=[O:13])[C:10](C)=[CH2:11].C(O)(=O)C(C)=C.C(OCCOC(=O)C(C)=C)(=O)C(C)=C.C(OSCCCCCC(C)C)(=O)CO.S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].[NH2:67][C:68]([O:70]CC)=[O:69].[OH-].[K+]>O>[C:9]([OH:14])(=[O:13])[CH:10]=[CH2:11].[NH2:67][C:68]([O:70][CH2:8][CH3:3])=[O:69]

Participants

10

Reactant 8

HCID 4093Methacrylic AcidHCID 5641Carbamic acid, ethyl ester2×HCID 7355Ethylene glycol dimethacrylateHCID 7501StyreneHCID 8872Hexyl methacrylateHCID 14797Potassium HydroxideHCID 24412Potassium PersulfateHCID 53936142HCID 53936142, compound

Product 1

HCID 21863578Urethane acrylate

Reagents, catalysts & solvents 1

HCID 962WaterSolvent5×

Conditions

Temperature
90 °C

Procedure

In a round-bottom flask, 76 g of styrene, 276 g of hexyl methacrylate, 24 g of methacrylic acid, 4 g of ethylene glycol dimethacrylate, 1.6 g of isooctylthio glycolate as a chain transfer agent, and 33.28 g of 30% Rhodafac RS 710 as an emulsifying agent are mixed in 136 ml of water forming an emulsion. An initiator solution is prepared by adding 1.39 g of potassium persulfate to 160 ml of water. A hot water solution is prepared by adding 32 ml of the initiator solution to 1160 ml of water preheated to 90° C. Simultaneous addition of the remaining initiator solution with the emulsion is added to the hot water solution over a period of 32 minutes to form a reaction mixture. After about 60% of the emulsion addition, another component, aliphatic urethane acrylate CN968 from Sartomer, is added to the reaction mixture for the incorporation of urethane linkages on the surface of the latex particle. The reaction mixture is maintained at 90° C. for 1.75 hours and then cooled to ambient temperature. The reaction mixture is then neutralized with 50% potassium hydroxide solution and filtered using 200 μm filter to obtain a latex with a rigid polymer shell containing urethane linkages.

Workup

  1. customAn initiator solution is prepared
  2. custompreheated to 90° C
  3. additionSimultaneous addition of the remaining initiator solution with the emulsion
  4. customto form a reaction mixture
  5. additionAfter about 60% of the emulsion addition
  6. temperaturecooled to ambient temperature
  7. filtrationfiltered
  8. filtrationfilter
  9. customto obtain a latex with a rigid polymer shell

Sources & evidence

ORD record
ord-1a6d47719905404e9c5d1cab0097d199
Source dataset
uspto-grants-2009_08
Patent number
US07569650B2

Reaction notes

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