4-ethenylphenol

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In 40 ml of pyridine was dissolved poly p-hydroxystyrene (VP-8000, manufactured by Nippon Soda Co., Ltd., weight average molecular weight 1000), and 1.28 g of di-t-butyl dicarbonate was added to the solution with stirring at room temperature. After carrying out the reaction at room temperature for 3 hours, the reaction liquid was added to a solution of 1 liter of ion-exchanged water and 20 g of concentrated hydrochloric acid. The powder precipitated was collected by filtration, washed with water, and dried to obtain a p-hydroxystyrene/p-(t-butyloxycarbonyloxy)-styrene copolymer (60/40). was added to the solution the reaction at room temperature for 3 hours the reaction liquid The powder precipitated was collected by filtration washed with water dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: The GPC analysis of the copolymer thus obtained revealed that its Mw and MwD were 10,600 and 1.82, respectively. Besides, the 1H-NMR spectrum analysis of the copolymer revealed that the copolymerization ratio of 4-hydroxystyrene to 3-methyl-2-butenyl acrylate was 54:46. The GPC analysis of the copolymer thus obtained

Conditions: temp:25.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: p-Hydroxystyrene (VP-8000, produced by Nippon Soda Co., Ltd.) in an amount of 70 g was dissolved in 320 g of propylene glycol monomethyl ether acetate (PGMEA) with heating, dehydrated by vacuum distillation, and then cooled to 25° C. To this solution, 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol were added, and further 17.5 g of t-butyl vinyl ether was added at a slow speed. In the resulting mixture, reaction was run for 5 hours at 20° C. Thereafter, the reaction solution was admixed with 0.28 g of triethylamine and 320 ml of ethyl acetate, and washed with 150 ml each of distilled water for three times. Therefrom, the solvent was distilled away, and the residue was concentrated. The thus obtained oil was dissolved in 100 ml of acetone, and poured slowly into 2 liter of distilled water. As a result, a powdery matter separated out. This powdery matter was filtered off and dried to yield 54 g of the desired resin. with heating dehydrated by vacuum distillation To this solution, 0.35 g of pyridinium p-toluenesulfonate and 22.4 g of cyclohexane ethanol were added further 17.5 g of t-butyl vinyl ether was added at a slow speed In the resulting mixture, reaction washed with 150 ml each of distilled water for three times Therefrom, the solvent was distilled away the residue was concentrated The thus obtained oil was dissolved in 100 ml of acetone poured slowly into 2 liter of distilled water As a result, a powdery matter separated out This powdery matter was filtered off dried

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1500 ml sulfonation flask, 135.6 g (1.13 mol) of 4-hydroxystyrene and 220.2 g (1.13 mol) of tert-butyl bromoacetate are dissolved in 800 ml of acetone and to the solution are added 195.0 g (1.41 mol) of potassium carbonate and 0.8 g of potassium iodide. The resultant suspension is stirred for 4 hours at 60° C. bath temperature. After cooling, the inorganic salts are removed by filtration and the filtrate is concentrated. The oily residue is taken up in 1000 ml of diethyl ether, washed twice with 800 ml of 1.0N sodium hydroxide solution and then three times with 1000 ml of water. The organic phase is separated, dried over magnesium sulfate and concentrated, giving 246.5 g of the desired product as a clear oil (93.2 %). After cooling the inorganic salts are removed by filtration the filtrate is concentrated washed twice with 800 ml of 1.0N sodium hydroxide solution The organic phase is separated dried over magnesium sulfate concentrated

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 250 ml round-bottomed flask, 15 g (125 mmol) of 4-hydroxystyrene and 0.4 g (2.3 mmol) of p-toluenesulfonic acid monohydrate are dissolved in 120 ml of diethyl ether. Then, at 5° C., 11.6 g (137 mmol) of 3,4-dihydro-2H-pyran are added dropwise over a period of 10 minutes. The mixture is allowed to reach room temperature and is further stirred for 20 hours. 1N NaOH solution is then added and the organic phase is washed twice with water, dried over magnesium sulfate and concentrated to yield 23.3 g (114 mmol, 90% of the theoretical yield) of 4-tetrahydropyran-2-yloxystyrene in the form of a colourless oil that can be used for the copolymerisation without being further purified. 1H-NMR (CDCl3, 100 mHz): δ7.37/d (J=9 Hz)/2H, 7.02/d (J=9 Hz)/2H, 6.52/dd (J1 =18 Hz, J2 =11 Hz)/1H, 5.50/dd (J1 =18 Hz, J2 =2 Hz)/1H, 5.41/m/1H, 5.11/dd (J1 =11 Hz, J2 =2 Hz)/1H, 4.0-3.7/m/1H, 3.7-3.4/m/1H, 2.2-1.2/m/6H. to reach room temperature the organic phase is washed twice with water dried over magnesium sulfate concentrated to yield 23.3 g (114 mmol, 90% of the

Conditions: temp:135.01; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: In a 1-liter sulfonating flask equipped with mechanical stirrer, reflux condenser and nitrogen delivery line, 300 ml of dimethyl sulfoxide are added to 150 g (0.91 mol) of 4-hydroxycinnamic acid, 6 g (54 mmol) of hydroquinone and 6 g (39 mmol) of 1,8-diazabicyclo[5.4.0]undec-7-ene. The mixture is then heated at 135° C. for 31/2 hours. After cooling, the mixture is poured onto ice and extracted three times with 500 ml of diethyl ether, and the organic phase is washed five times with 100 ml of water, dried over magnesium sulfate and concentrated. The resulting oil is recrystallised twice from n-hexane to yield 69.07 g (0.58 mol, 63% of the theoretical yield) of 4-hydroxystyrene in the form of a white powder (m.p. 68° C.). equipped with mechanical stirrer reflux condenser After cooling the mixture is poured onto ice extracted three times with 500 ml of diethyl ether the organic phase is washed five times with 100 ml of water dried over magnesium sulfate concentrated The resulting oil is recrystallised twice from n-hexane to yield 69.07 g (0.58 mol, 63% of the

Conditions: temp:0.00; pressure:0.00; stir:; See reaction.notes.procedure_details.

Procedure: Corresponding method-wise to example 1, 4-VP was used as cationic comonomer. Additions of vinylpyridine in 20 ml purest water via the injection pump: (11) 0.195 g or (12) 0.389 g or (13) 0.585 g or (14) 0.78 g or (15) 0.975 g—latices no. 11—no. 15 in Tab. 1.