Itaconic acid → Styrene-butadiene itaconic acid

HRID 1034311Notes

Reaction equation

HRID 1034311 reaction equation
[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3].C1CC(NC2[C:25]3[C:20](=[CH:21][C:22](Cl)=[C:23](Cl)[CH:24]=3)[C:19]([C:28]3C=CN=CC=3)=NN=2)CC1.S(OOS([O-])(=O)=O)([O-])(=O)=O.[Na+].[Na+].C=CC=C.C(N(CC([O-])=O)CC([O-])=O)CN(CC([O-])=O)CC([O-])=O.[Na+].[Na+].[Na+].[Na+]>C=CC1C=CC=CC=1.O>[CH2:1]=[CH:2][CH:4]=[CH2:5].[CH2:28]=[CH:19][C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1.[C:1]([OH:9])(=[O:8])[C:2]([CH2:4][C:5]([OH:7])=[O:6])=[CH2:3]

Participants

8

Reactant 5

HCID 811Itaconic acid2×HCID 6144Edetate SodiumHCID 78451,3-ButadieneHCID 62655Sodium Persulfate2×HCID 1170725486,7-dichloro-N-cyclopentyl-4-(pyridin-4-yl)phthalazin-1-amine2×

Product 1

HCID 169127Styrene-butadiene itaconic acid

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 7501StyreneSolvent2×

Conditions

Temperature
165 fahrenheit

Procedure

A styrene-butadiene-itaconic acid copolymer latex was prepared by adding to a pressure reactor with constant stirring 34.7 parts water, 1 part itaconic acid, 0.8 part of a 10% solution of Aerosol A-196 surfactant (sodium dicyclohexyl sulfosuccinate available from American Cyanamid Co., Wayne, N.J.), and 1 part of a polystyrene seed, 25 nm particle size. The mixture was heated to 165° F and 0.2 part sodium persulfate was added to initiate the reaction. Then 40 parts butadiene, 60 parts styrene, 1.0 part Sulfole 120 mercaptan (tertiary dodecyl mercaptan available from Phillips Chemical Co., a subsidiary of Phillips Petroleum Co., Bartlesville, Okla.) dissolved in styrene, an additional 0.5 part sodium persulfate, an additional 1.5 parts Aerosol A-196, 0.03 part Versene 100 (sodium ethylene diamine tetraacetate available from Dow Chemical Co., Midland, Mich.), 4 parts itaconic acid, and 58.5 parts water were added over a 6 hour period. The final mixture was heated at a temperature of 190° F for 5 hours. The resulting emulsion polymer was cooled and removed from the reactor. It had a pH value of 2.2, which was adjusted to pH 7.0 with ammonium hydroxide. Total solids were 44.1 percent. Viscosity was measured with a Brookfield Model RVF viscometer at 20 rpm and found to be 360 cps. Average particle size was 122 nm.

Workup

  1. additionby adding to a pressure reactor
  2. customthe reaction
  3. temperatureThe resulting emulsion polymer was cooled
  4. customremoved from the reactor

Sources & evidence

ORD record
ord-1e00fcf28f8d4a8da5876ed4dd9db9cd
Source dataset
uspto-grants-1994_05
Patent number
US05314943

Reaction notes

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