Functionalized Particulate Support Material and Methods of Making and Using the Same

• US 20150251158A1
• Filed: 09/16/2013
• Published: 09/10/2015
• Est. Priority Date: 09/17/2012
• Status: Active Grant

• Current Assignee: W R Grace & Company - CONN (WR Grace & Company)
• Original Assignee: W R Grace & Company - CONN (WR Grace & Company)
• Inventors: Gu, Feng
• Granted Patent: US 11,529,610 B2
• Time in Patent Office: Days
• US Class Current: 1/1
• CPC Class Codes: B01D 15/361 Ion-exchange
• CPC Class Codes: B01J 20/0229 Compounds of Fe
• CPC Class Codes: B01J 20/0248 Compounds of B, Al, Ga, In, Tl B01J20/08 takes precedence
• CPC Class Codes: B01J 20/04 comprising compounds of alkali metals, alkaline earth metals or magnesium
• CPC Class Codes: B01J 20/24 Naturally occurring macromolecular compounds, e.g. humic acids or their derivatives
• CPC Class Codes: B01J 20/261 obtained by reactions only involving carbon to carbon unsaturated bonds macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds per se C08F
• CPC Class Codes: B01J 20/262 obtained otherwise than by reactions only involving carbon to carbon unsaturated bonds, e.g. obtained by polycondensation macromolecular compounds obtained otherwise than by reactions only involving unsaturated carbon-to-carbon bonds per se C08G
• CPC Class Codes: B01J 20/264 derived from different types of monomers, e.g. linear or branched copolymers, block copolymers, graft copolymers
• CPC Class Codes: B01J 20/283 based on silica
• CPC Class Codes: B01J 2220/44 Materials comprising a mixture of organic materials materials coated or impregnated on a carrier B01J20/32
• CPC Class Codes: B01J 2220/46 Materials comprising a mixture of inorganic and organic materials materials coated or impregnated on a carrier B01J20/32
• CPC Class Codes: B01J 2220/52 Sorbents specially adapted for preparative chromatography
• CPC Class Codes: B01J 2220/58 Use in a single column
• CPC Class Codes: B01J 2220/62 In a cartridge
• CPC Class Codes: B65B 3/04 Methods of, or means for, filling the material into the containers or receptacles
• CPC Class Codes: B65B 7/02 Closing containers or receptacles deformed by, or taking-up shape, of, contents, e.g. bags, sacks
• CPC Class Codes: C08F 222/38 Amides
• CPC Class Codes: G01N 2030/8813 biological materials
• CPC Class Codes: G01N 30/96 using ion-exchange G01N30/02, G01N30/90 take precedence
• CPC Class Codes: Y10T 428/2982 Particulate matter [e.g., sphere, flake, etc.]

Abstract

Functionalized particulate support material suitable for use in chromatography columns or cartridges, such as in a liquid chromatography (HPLC) column, is disclosed. Chromatography columns or cartridges containing the functionalized particulate support material, methods of making functionalized particulate support material, and methods of using functionalized particulate support material, such as a media in a chromatography column or cartridge, are also disclosed.

Claims

32-1. The method of claim 32, wherein said treating step bonds at least one of said first set of functional groups or second set of functional groups to the particle surface followed by said polymerization.

64. A chromatography column or cartridge housing functionalized particulate support material comprising:

a particle having a particle surface; and

a combination of functional groups extending from the particle surface, said combination of functional groups comprising (i) a first set of functional groups on the particle surface bonded to at least one polymer that extends from the particle surface, and (ii) a second set of functional groups that increases the wettability of said particle surface.

65. The chromatography column or cartridge of claim 64, wherein said second functional group is bonded to said one or more monomers or to the particle surface.

66. The chromatography column or cartridge of claim 64 or 65, wherein said particle comprises an inorganic particle,

67. The chromatography column or cartridge of any one of claims 64 to 66, wherein said particle comprises a silica particle.

68. The chromatography column or cartridge of any one of claims 64 to 67, wherein said particle has a particle size, as measured by a median particle dimension, ranging from about 1 μ

m to about 120 μ

m.

69. The chromatography column or cartridge of any one of claims 64 to 68, wherein said particle comprises a porous particle having a particle size, as measured by a median particle dimension, ranging from about 10 μ

m to about 120 μ

m, and a median pore size of at least 150 Å

.

70. The chromatography column or cartridge of any one of claims 64 to 69, wherein said first set of functional groups comprises unsaturated bonds.

71. The chromatography column or cartridge of any one of claims 64 to 70, wherein said first set of functional groups comprises vinyl groups, allyl groups, acryl groups, methacryl groups, or any combination thereof.

72. The chromatography column or cartridge of any one of claims 64 to 71, wherein said second set of functional groups comprises at least one hydrophilic organic group.

73. The chromatography column or cartridge of any one of claims 64 to 72, wherein said second set of functional groups comprises hydroxyl groups, diol groups, oxyethylene groups, polyethylene groups, carboxylic acid groups, amine groups, amide groups, or any combination thereof.

74. The chromatography column or cartridge of any one of claims 64 to 73, wherein wherein the carbon content on said particle surface is less than or equal to about 2.0 wt % by weight of the particulate support material.

75. The chromatography column or cartridge of any one of claims 64 to 74, wherein said first set of functional groups comprises vinyl groups, and said second set of functional groups comprises diol groups.

76. The chromatography column or cartridge of any one of claims 64 to 75, wherein said first and second set of functional groups are part of a molecule comprising azo groups and carboxylic acid groups.

77. The chromatography column or cartridge of any one of claims 64 to 76, wherein said particle surface is further treated with a quaternary ammonium salt or a quaternary ammonium cation thereof.

78. The chromatography column or cartridge of any one of claims 64 to 77, wherein said particle surface is further treated with a quaternary ammonium cation comprising tetramethylammonium chloride or a tetramethylammonium cation.

79. The chromatography column or cartridge of any one of claims 64 to 78, wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface.

80. The chromatography column or cartridge of any one of claims 64 to 79, wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more spacer monomers so as to form polymer chains extending from said particle surface.

81. The chromatography column or cartridge of claim 80, wherein the polymer chains comprise identical or different repeating units of the following formula

82. The chromatography column or cartridge of any one of claims 64 to 81, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one anionic monomer.

83. The chromatography column or cartridge of any one of claims 64 to 82, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 2-acrylamido-2-methylpropane sulfonic acid, and said one or more optional spacer monomers comprising methylenebisacrylamide.

84. The chromatography column or cartridge of any one of claims 64 to 83, wherein polymerization includes a chain transfer agent.

85. The chromatography column or cartridge of any one of claims 64 to 84, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one cationic monomer.

86. The chromatography column or cartridge of any one of claims 64 to 85, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 3-acrylamidopropyltrimethylammonium chloride or methylacrylamidopropyl, and said one or more optional spacer monomers comprising diallyidimethylammonium chloride.

87. A functionalized particulate support material comprising:

a particle having a particle surface and

a combination of functional groups extending from the particle surface, said combination of functional groups comprising (i) a first set of functional groups on the particle surface bonded to at least one polymer that extends from the particle surface, and (ii) a second set of functional groups that increases the wettability of said particle surface.

88. The functionalized particulate support material of claim 87, wherein said second functional group is bonded to said one or more monomers or to the particle surface.

89. The functionalized particulate support material of claim 87 or 88, wherein said particle comprises an inorganic particle.

90. The functionalized particulate support material of any one of claims 87 to 89, wherein said particle comprises a silica particle.

91. The functionalized particulate support material of any one of claims 87 to 90, wherein said particle has a particle size, as measured by a median particle dimension, ranging from about 1 μ

m to about 120 μ

m.

92. The functionalized particulate support material of any one of claims 87 to 91, wherein said particle comprises a porous particle having a particle size, as measured by a median particle dimension, ranging from about 10 μ

m to about 120 μ

m, and a median pore size of at least 150 Å

.

93. The functionalized particulate support material of any one of claims 87 to 92, wherein said first set of functional groups comprises unsaturated bonds.

94. The functionalized particulate support material of any one of claims 87 to 93, wherein said first set of functional groups comprises vinyl groups, allyl groups, acryl groups, methacryl groups, or any combination thereof.

95. The functionalized particulate support material of any one of claims 87 to 94, wherein said second set of functional groups comprises at least one hydrophilic organic group.

96. The functionalized particulate support material of any one of claims 87 to 95, wherein said second set of functional groups comprises hydroxyl groups, diol groups, oxyethylene groups, polyethylene groups, carboxylic acid groups, amine groups, amide groups, or any combination thereof.

97. The functionalized particulate support material of any one of claims 87 to 96, wherein wherein the carbon content on said particle surface is less than or equal to about 2.0 wt % by weight of the particulate support material.

98. The functionalized particulate support material of any one of claims 87 to 97, wherein said first set of functional groups comprises vinyl groups, and said second set of functional groups comprises diol groups.

99. The functionalized particulate support material of any one of claims 87 to 98, wherein said first and second set of functional groups are part of a molecule comprising azo groups and carboxylic acid groups.

100. The functionalized particulate support material of any one of claims 87 to 99, wherein said particle surface is further treated with a quaternary ammonium salt or a quaternary ammonium cation thereof.

101. The functionalized particulate support material of any one of claims 87 to 100, wherein said particle surface is further treated with a quaternary ammonium cation comprising tetramethylammonium chloride or a tetramethylammonium cation.

102. The functionalized particulate support material of any one of claims 87 to 101 wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface.

103. The functionalized particulate support material of any one of claims 87 to 102, wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more spacer monomers so as to form polymer chains extending from said particle surface.

104. The functionalized particulate support material of claim 103, wherein the polymer chains comprise identical or different repeating units of the following formula

105. The functionalized particulate support material of any one of claims 87 to 104, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one anionic monomer.

106. The functionalized particulate support material of any one of claims 87 to 105, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 2-acrylamido-2-methylpropane sulfonic acid, and said one or more optional spacer monomers comprising methylenebisacrylamide.

107. The functionalized particulate support material of any one of claims 87 to 106, wherein polymerization includes a chain transfer agent.

108. The functionalized particulate support material of any one of claims 87 to 107, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one cationic monomer.

109. The functionalized particulate support material of any one of claims 87 to 108, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 3-acrylamidopropyltrimethylammonium chloride or methylacrylamidopropyl, and said one or more optional spacer monomers comprising diallyldimethylammonium chloride.

110. A functionalized particulate support material comprising:

a particle having a particle surface and a median pore size of at least 150 Å

; and

a first set of functional groups extending from the particle surface, said first set of functional groups on the particle surface bonded to at least one polymer that extends from the particle surface.

111. The functionalized particulate support material of claim 110, wherein the particle surface comprises, a second set of functional groups that increases the wettability of said particle surface.

112. The functionalized particulate support material of claim 111, wherein said second functional group is bonded to said one or more monomers or to the particle surface.

113. The functionalized particulate support material of any one of claims 110 to 112, wherein said particle comprises an inorganic particle.

114. The functionalized particulate support material of any one of claims 110 to 113, wherein said particle comprises a silica particle.

115. The functionalized particulate support material of any one of claims 110 to 114, wherein said particle has a particle size, as measured by a median particle dimension, ranging from about 1 μ

m to about 120 μ

m.

116. The functionalized particulate support material of any one of claims 110 to 115, wherein said particle comprises a porous particle having a median pore size of at least about 150 Å

up to about 6000 Å

.

117. The functionalized particulate support material of any one of claims 110 to 116, wherein said first set of functional groups comprises unsaturated bonds.

118. The functionalized particulate support material of any one of claims 110 to 117, wherein said first set of functional groups comprises vinyl groups, allyl groups, acryl groups, methacryl groups, or any combination thereof.

119. The functionalized particulate support material of any one of claims 110 to 118, wherein said second set of functional groups comprises at least one hydrophilic organic group.

120. The functionalized particulate support material of any one of claims 110 to 119, wherein said second set of functional groups comprises hydroxyl groups, diol groups, oxyethylene groups, polyethylene groups, carboxylic acid groups, amine groups, amide groups, or any combination thereof.

121. The functionalized particulate support material of any one of claims 110 to 120, wherein wherein the carbon content on said particle surface is less than or equal to about 2.0 wt % by weight of the particulate support material.

122. The functionalized particulate support material of any one of claims 110 to 121, wherein said first set of functional groups comprises vinyl groups, and said second set of functional groups comprises diol groups.

123. The functionalized particulate support material of any one of claims 110 to 122, wherein said first and second set of functional groups are part of a molecule comprising azo groups and carboxylic acid groups.

124. The functionalized particulate support material of any one of claims 110 to 123, wherein said particle surface is further treated with a quaternary ammonium salt or a quaternary ammonium cation thereof.

125. The functionalized particulate support material of any one of claims 110 to 124, wherein said particle surface is further treated with a quaternary ammonium cation comprising tetramethylammonium chloride or a tetramethylammonium cation.

126. The functionalized particulate support material of any one of claims 110 to 125, wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface.

127. The functionalized particulate support material of any one of claims 110 to 126, wherein at least a portion of said first set of functional groups is polymerized with one or more monomers and one or more spacer monomers so as to form polymer chains extending from said particle surface.

128. The functionalized particulate support material of claim 127, wherein the polymer chains comprise identical or different repeating units of the following formula

129. The functionalized particulate support material of any one of claims 110 to 128, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one anionic monomer.

130. The functionalized particulate support material of any one of claims 110 to 129, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 2-acrylamido-2-methylpropane sulfonic add, and said one or more optional spacer monomers comprising methylenebisacrylamide.

131. The functionalized particulate support material of any one of claims 110 to 130, wherein polymerization includes a chain transfer agent.

132. The functionalized particulate support material of any one of claims 110 to 131, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising at least one cationic monomer.

133. The functionalized particulate support material of any one of claims 110 to 132, wherein at least a portion of said first set of functional groups are polymerized with one or more monomers and one or more optional spacer monomers so as to form polymer chains extending from said particle surface, said one or more monomers comprising 3-acrylamidopropyltrimethylammonium chloride or methylacrylamidopropyl, and said one or more optional spacer monomers comprising diallyldimethylammonium chloride.