US 11,952,530 B2
Aryl-substituted saccharides or glycosides and use thereof in a drilling fluid composition
Xiqiang Si, Henan (CN); Zhonghua Wang, Henan (CN); Weiting Li, Henan (CN); Jun Wei, Henan (CN); Zhongjin Wang, Henan (CN); and Yuebin Lv, Henan (CN)
Assigned to CHINA PETROLEUM & CHEMICAL CORPORATION, Beijing (CN); Sinopec Petroleum Engineering Technology Service Co., Ltd., Beijing (CN); Drilling Engineering Technology Research Institute of Sinopec Zhongyuan Petroleum Engineering Co., LTD, Henan (CN); and SINOPEC ZHONGYUAN PETROLEUM ENGINEERING CO., LTD, Henan (CN)
Appl. No. 16/966,870
Filed by CHINA PETROLEUM & CHEMICAL CORPORATION, Beijing (CN); Sinopec Petroleum Engineering Technology Service Co., Ltd., Beijing (CN); Drilling Engineering Technology Research Inst. of Sinopec Zhongyuan Petroleum Engineering Co., LTD, Henan (CN); and SINOPEC ZHONGYUAN PETROLEUM ENGINEERING CO., LTD, Henan (CN)
PCT Filed Nov. 29, 2019, PCT No. PCT/CN2019/121908
§ 371(c)(1), (2) Date Jul. 31, 2020,
PCT Pub. No. WO2020/119478, PCT Pub. Date Jun. 18, 2020.
Claims priority of application No. 201811525211.1 (CN), filed on Dec. 13, 2018.
Prior Publication US 2021/0040373 A1, Feb. 11, 2021
Int. Cl. C09K 8/08 (2006.01); C07H 15/207 (2006.01)
CPC C09K 8/08 (2013.01) [C07H 15/207 (2013.01)] 19 Claims
OG exemplary drawing
 
1. An aryl-substituted saccharide or glycoside or a mixture of a plurality of aryl-substituted saccharides or glycosides, individually or in combination, bearing a substituent A and a sub stituent B, wherein the substituent A contains in its structure a unit

OG Complex Work Unit Chemistry
wherein R6 is C2-8 linear or branched alkylene, the substituent B contains in its structure a unit

OG Complex Work Unit Chemistry
wherein Ar is an optionally substituted C6-20 aryl.
 
15. A process of producing an aryl-substituted saccharide or glycoside or a mixture of a plurality of aryl-substituted saccharides or glycosides comprising the steps of:
1) reacting a saccharide or glycoside represented schematically by the following formula (X-1) or formula (X-2), optionally in the presence of a catalyst, to obtain an etherified saccharide or glycoside,

OG Complex Work Unit Chemistry
in formula (X-1) and formula (X-2), two R1, same as or different from one another, are each independently selected from the group consisting of hydrogen and C1-20 linear or branched alkyl group, and m is an integer of 1 to 3, wherein the etherifying agent is an alkylene oxide monomer represented schematically by the following formula (A-11), a polyhydroxyl monomer represented schematically by the following formula (A-21) or a combination thereof,

OG Complex Work Unit Chemistry
in formula (A-11), Ra is a hydrogen atom or a C1-5 linear or branched alkyl group, and

OG Complex Work Unit Chemistry
in formula (A-21), Rb is a C1-4 linear or branched alkylenyl group and X is a hydroxyl group or a halogen atom,
2) reacting the etherified saccharide or glycoside with an arylethylene monomer represented schematically by the following formula (B-11) or formula (B-12), optionally using an acrylamide monomer represented schematically by the following formula (B-21), optionally using a sulfoethylene monomer represented schematically by the following formula (B-31) or formula (B-32), optionally using a siloxyethylene monomer represented schematically by the following formula (B-41) or formula (B-42), and optionally using a carboxyethylene monomer represented schematically by the following formula (B-51) or formula (B-52) for the reaction, to obtain the aryl-substituted saccharide or glycoside or the mixture of a plurality of aryl-substituted saccharides or glycosides,

OG Complex Work Unit Chemistry
in formula (B-11), Ar is an optionally substituted C6-20 aryl group,

OG Complex Work Unit Chemistry
in formula (B-31) and formula (B-32), L1 is any linking group having no more than 10 carbon atoms and M is hydrogen, alkali metal or ammonium (NH4),

OG Complex Work Unit Chemistry
in formula (B-41) and formula (B-42), L2 is any linking group having no more than 10 carbon atoms, and R′ is a C1-4 linear or branched alkyl group,

OG Complex Work Unit Chemistry
in formula (B-51) and formula (B-52), L3 is any linking group having no more than 10 carbon atoms, and M is hydrogen, alkali metal, or ammonium (NH4).