Jan. 10, 2019  58  US 2019/0010119 Al  dropwise addition, stirring was continued for 18 hours while  the polymerization temperature was kept at 80°  C., followed  by cooling to room temperature. The obtained polymer  solution was added dropwise to 22.5 kg of diisopropyl ether,  thereby making the copolymer aggregated. The diisopropyl  ether was removed by decantation, and the copolymer was  dissolved in 2,250 g of acetone. This acetone solution was  added dropwise to 22.5 kg of diisopropyl ether, and the  precipitated copolymer was filtered off. The filtered copo› lymer was dissolved in 2,250 g of acetone again. This  acetone solution was added dropwise to 22.5 kg of water,  and the precipitated copolymer was filtered off. Subse› quently, this was dried at 40°  C. for 40 hours to give 700 g  of Polymer-16 as a white polymer. Polymer-16 was mea› sured for $^{13}$C-NMR, $^{1}$H-NMR, and GPC to give the follow› ing results.  [0252]  In the same manner as in Synthesis Example 3-1  except for changing the type and incorporated ratio (molar  ratio) of each monomer, Polymers-IO to 15 were synthe› sized.  [0253]  Under nitrogen atmosphere, a 3,000 mL of drop› ping cylinder was charged with 890 g of 50.0 mass  %  PGMEA solution of 4-hydroxystyrene, 47.7 g of acenaph› thylene, 310 g of 54.7 mass  % PGMEA solution of 4-(2- hydroxy-2-propyl)styrene, 87.0 g of triphenylsulfonium-1,  1,3 ,3 ,3-pentafluoro-2-methacry loy loxypropane-1-sulfonate,  96.1  g  of  dimethyl-2,2’-azobis-(2-methylpropionate)  (V-601, manufactured by Waka Pure Chemical Industries,  Ltd.), as well as 360 g of y-butyrolactone and 220 g of  PGMEA as solvents to prepare a solution. Additionally,  another 5,000 mL of flask for polymerization under nitrogen  atmosphere was charged with 580 g of y-butyrolactone. To  this, being heated to 80°  C., the prepared solution described  above was added dropwise over 4 hours. After finishing the  [0255]  The types and incorporated ratios of monomers in  Polymers-9 to 26 are summarized in Table 4. The structures  of the repeating units incorporated to the polymers are  shown in Tables 5 to 8. Incidentally, each Mw of Polymers-9  to 15 and 25 is a value measured by GPC using THF as a  solvent in terms of polystyrene, and each Mw of Polymers- 16 to 24 and 26 is a value measured by GPC using  dimethylformamide as a solvent in terms of polystyrene.  [0254]  In the same manner as in Synthesis Example 3-2  except for changing the type and incorporated ratio (molar  ratio) of each monomer, Polymers-17 to 26 were synthe› sized.  [Synthesis Examples 3-9 to 3-18] Synthesis of  Polymers-17 to 26  [Synthesis Example 3-8] Synthesis of Polymer-16  [Synthesis Examples 3-2 to 3-7] Synthesis of  Polymers-IO to 15  Polymer-16  Q_  +s--0  Polymer-9  OH  Cl  (Mw  ~  13,000, Mw/Mn  ~  1.62)  (Mw  ~  4,500, Mw/Mn  ~  1.65)  trated to ‰, and added to 15 L of methanol, thereby forming  precipitate. The obtained white solid was filtered off, dried  at 40°  C. under vacuum to give 309 g of white polymer.  [0251]  The obtained polymer was dissolved in a mixed  solvent of 488 g of methanol and 540 g of THF again, and  162 g oftriethylamine and 32 g of water were added thereto  to perform deprotection reaction at 60°  C. for 40 hours. This  reaction solution was concentrated, and then dissolved in  870 g of ethyl acetate. This was subjected to neutralization,  separation, and washing with a mixed liquid of 250 g of  water and 98 g of acetic acid for once, and was subjected to  separation and washing with a mixture of 225 g of water and  7 5 g of pyridine for once, together with 225 g of water for  four times. Then, the upper layer of ethyl acetate solution  was concentrated, and dissolved in 250 g of acetone. This  was added to 15 L of water to precipitate, followed by  filtration and drying at 50°  C. for 40 hours in vacuum to give  223 g of Polymer-9 as a white polymer. Polymer-9 was  measured for $^{13}$C-NMR, $^{1}$H-NMR, and GPC to give the  following results. 