US 11,897,974 B2
Method for manufacturing thermoplastic poly(vinyl alcohol) derivative in a melt state reaction and products thereof
Kuisma Littunen, Lappeenranta (FI); Harri Kosonen, Lappeenranta (FI); Janne Antila, Hämeenlinna (FI); Jaakko Rautalahti, Valkeakoski (FI); and Mikko Rissanen, Espoo (FI)
Assigned to UPM-KYMMENE CORPORATION, Helsinki (FI)
Appl. No. 17/434,870
Filed by UPM-Kymmene Corporation, Helsinki (FI)
PCT Filed Mar. 18, 2019, PCT No. PCT/FI2019/050225
§ 371(c)(1), (2) Date Aug. 30, 2021,
PCT Pub. No. WO2020/188138, PCT Pub. Date Sep. 24, 2020.
Prior Publication US 2022/0162357 A1, May 26, 2022
Int. Cl. C08F 16/06 (2006.01); C09J 7/40 (2018.01); C09J 7/21 (2018.01); C08F 8/14 (2006.01); D21H 19/20 (2006.01); D21H 19/32 (2006.01); D21H 19/82 (2006.01); D21H 27/00 (2006.01); D21H 27/06 (2006.01)
CPC C08F 16/06 (2013.01) [C08F 8/14 (2013.01); C09J 7/21 (2018.01); C09J 7/401 (2018.01); D21H 19/20 (2013.01); D21H 19/32 (2013.01); D21H 19/824 (2013.01); D21H 27/001 (2013.01); D21H 27/06 (2013.01); C08F 2810/30 (2013.01); C09J 2400/283 (2013.01)] 17 Claims
OG exemplary drawing
 
1. A method for manufacturing thermoplastic poly(vinyl alcohol) derivative (CMP1; CMP2; CMP3) which contains pendant chains which end into vinyl groups, the method comprising:
heating (HT1) thermoplastic poly(vinyl alcohol) (PVA1) having hydroxyl groups, wherein the thermoplastic poly(vinyl alcohol) (PVA1) has been dried and has a degree of hydrolysis in the range of 65 to 90 mol-%, and
admixing (AD1) reagent (RGT1) with the thermoplastic poly(vinyl alcohol) (PVA1), wherein said reagent (RGT1) is an organic acid anhydride (AH1; AH2; AH3; AH4; AH5) having at least a chain which has a catenated carbon structure of at least 4 carbon atoms and which ends into a vinyl group,
such that a mixture (MXT1) is obtained which contains molten thermoplastic poly(vinyl alcohol) (PVA1) having hydroxyl groups and organic acid anhydride (AH1; AH2; AH3; AH4; AH5) which contains chains which end into vinyl groups, and
mixing (MR1) the mixture (MXT1) at a temperature which is above the melting point of the mixture (MXT1), thereby causing a reaction in a melt state, wherein at least some of the organic acid anhydride (AH1; AH2; AH3; AH4; AH5) reacts with the hydroxyl groups of the thermoplastic poly(vinyl alcohol) (PVA1) in an ester bond forming condensation reaction,
such that reaction product (PROD1) is formed which contains
carboxylic acid residue (RD1; RD2; RD3) of the ester bond forming condensation reaction, wherein at least some of said carboxylic acid residue contains chains which end into vinyl groups, and
thermoplastic poly(vinyl alcohol) derivative (CMP1; CMP2; CMP3) which contains ester bonded pendant chains of which at least some end into vinyl groups.