Patent US4650784A successfully refreshed from Google Patents.
US4650784A
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Bonded phase of silica for solid phase extraction
Assignee: Avantor Performance Materials LLC
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Filing: 1986-02-20
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Granted: 1987-03-17
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Expires: 2006-02-20
Abstract
Abstract A bonded phase silica product of the formula: ##STR1## in which ##STR2## is the backbone of a silica gel or controlled pore glass, X is selected from --O--, --S--, ##STR3## each R and R 1 are each independently selected from hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently alkyl of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4, is suitable for use in solid phase extraction for cleanup of urine samples for analysis of cannabinoids.
Inventors
- 👤 Hugh E. Ramsden
- 👤 Joseph M. Patterson, III
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-09 03:51
CPC Classifications
C; C07; C07F; C07F7/00; G; G01; G01N; G01N33/00; G01N33/48; G01N33/50; G01N33/94; G01N33/948; B; B01; B01J; B01J20/00; B01J20/02; B01J20/10; B01J20/103; B01J20/28; B01J20/28002; B01J20/28004; B01J20/28054; B01J20/28078; B01J20/281; B01J20/286; B01J20/30; B01J20/3092; B01J20/32; B01J20/3202; B01J20/3204; B01J20/3231; B01J20/3242; B01J20/3244; B01J20/3246; B01J20/3257; B01J20/3259; B01J20/3263; B01J2220/00; B01J2220/50; B01J2220/54; B01J2220/58
Claims Analysis
Total Claims: 34
Claim 1
Independent Claim
109 words
A solid phase bonded silica product of the formula: ##STR16## in which ##STR17## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--,--S--, ##STR18## each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4.
Claim 2
Dependent Claim
109 words
A solid phase bonded silica product of the formula: ##STR16## in which ##STR17## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--,--S--, ##STR18## each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4.
Claim 3
Dependent Claim
81 words
A solid phase bonded silica product of claim 1 wherein the silica is selected from the group consisting of particulate silica gel having an average particle diameter of from about 3 to about 70 microns and an average pore size of from about 50 to about 1000 Angstrom units, and particulate controlled pore glass having an average particle diameter of from about 37 to about 177 microns and an average pore size of from about 40 to about 1000 Angstrom units.
Claim 4
Dependent Claim
43 words
A solid phase bonded silica product of claim 2 wherein the silica is particulate silica gel having an average particle diameter of from about 3 to about 70 microns and an average pore size of from about 50 to about 1000 Angstrom units.
Claim 5
Dependent Claim
88 words
The solid phase bonded silica product of claim 2 wherein n is 3, X is --S--, each R is selected from hydrogen, --CH 3 or --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero or 1, R 1 is hydrogen or --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , and R 2 is selected from --CH 3 , --C 2 H 5 and --C 4 H 9 .
Claim 6
Dependent Claim
31 words
The solid phase bonded silica product of claim 2 in which n is 3, X is ##STR19## each R is H, p is zero and R 2 is --CH 3 .
Claim 7
Dependent Claim
33 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, each R is hydrogen, p is zero and R 2 is --C 2 H 5 .
Claim 8
Dependent Claim
35 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is hydrogen and R 2 is --CH 3 .
Claim 9
Dependent Claim
33 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, each R is hydrogen, p is zero and R 2 is --C 2 H 5 .
Claim 10
Dependent Claim
53 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, one R is hydrogen and the other R is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 11
Dependent Claim
39 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --O--, one R is hydrogen and the other R is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 12
Dependent Claim
47 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --O--, each R is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 13
Dependent Claim
51 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , and R 2 is --CH 3 .
Claim 14
Dependent Claim
37 words
The solid phase bonded silica product of claim 2 in which n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is hydrogen and R 2 is --C 4 H 9 .
Claim 15
Dependent Claim
122 words
A column suitable for solid phase extraction comprising a column packed with a solid phase bonded silica product of the formula: ##STR20## in which ##STR21## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--, --S--, ##STR22## each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4.
Claim 16
Dependent Claim
122 words
A column suitable for solid phase extraction comprising a column packed with a solid phase bonded silica product of the formula: ##STR20## in which ##STR21## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--, --S--, ##STR22## each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4.
Claim 17
Dependent Claim
77 words
A column of claim 14 wherein the silica is selected from the group consisting of particulate silica gel having an average particle diameter of from about 3 to about 70 microns and an average pore size of from about 50 to about 1000 Angstrom units, and particulate controlled pore glass having an average particle diameter of from about 37 to about 177 microns and an average pore size of from about 40 to about 1000 Angstrom units.
Claim 18
Dependent Claim
39 words
A column of claim 15 wherein the silica is particulate silica gel having an average particle diameter of from about 3 to about 70 microns and an average pore size of from about 50 to about 1000 Angstrom units.
Claim 19
Dependent Claim
91 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, each R is selected from hydrogen, --CH 3 or --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero or 1, R 1 is hydrogen or --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , and R 2 is selected from --CH 3 , --C 2 H 5 and --C 4 H 9 .
Claim 20
Dependent Claim
33 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is ##STR23## each R is H, p is zero and R 2 is --CH 3 .
Claim 21
Dependent Claim
35 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, n is --S--, each R is hydrogen, p is zero and R 2 is --C 2 H 5 .
Claim 22
Dependent Claim
37 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is hydrogen and R 2 is --CH 3 .
Claim 23
Dependent Claim
35 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, each R is hydrogen, p is zero and R 2 is --C 2 H 5 .
Claim 24
Dependent Claim
55 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, one R is hydrogen and the other R is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 25
Dependent Claim
41 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --O--, one R is hydrogen and the other R is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 26
Dependent Claim
49 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --O--, each R is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , p is zero and R 2 is --CH 3 .
Claim 27
Dependent Claim
53 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is --CH 2 ) m COOR 3 where m is 1 and R 3 is --CH 3 , and R 2 is --CH 3 .
Claim 28
Dependent Claim
39 words
A column of claim 15 wherein in the solid phase bonded silica product n is 3, X is --S--, each R is hydrogen, p is 1, R 1 is hydrogen and R 2 is --C 4 H 9 .
Claim 29
Independent Claim
358 words
A method of preparing a solid phase bonded silica product of the formula: ##STR24## in which ##STR25## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--, --S--, ##STR26## each R and R 1 are each independently selected from the group consisting of hydrogen, and alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4, which comprises: (a) reacting in a suitable inert organic solvent having a boiling point of at least about 80° C. (1) a bonded phase silica reactant of the formula ##STR27## wherein ##STR28## is the backbone of a silica gel or controlled pore glass and Z is selected from the group consisting of ##STR29## wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms and x is an integer of from zero to 3 with the proviso that the total number of carbon atoms in the radical Z, when Z is the unsaturated group, does not exceed 5 carbon atoms, and m is an integer of from 2 to 5, with (2) a compound of the formula: ##STR30## wherein Y is selected from the group consisting of --O-- and --S-- and each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , and R 2 and R 3 each independently an alkyl group of from 1 to 4 carbon atoms, p is zero or one and m is an integer of from 1 to 4, (b) recovering the resultant solid fraction from the reaction mixture; and (c) heating said solid fraction at a temperature and for a time sufficient to dry said solid fraction.
Claim 30
Independent Claim
358 words
A method of preparing a solid phase bonded silica product of the formula: ##STR24## in which ##STR25## is the backbone of a silica gel or controlled pore glass, X is selected from the group consisting of --O--, --S--, ##STR26## each R and R 1 are each independently selected from the group consisting of hydrogen, and alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4, which comprises: (a) reacting in a suitable inert organic solvent having a boiling point of at least about 80° C. (1) a bonded phase silica reactant of the formula ##STR27## wherein ##STR28## is the backbone of a silica gel or controlled pore glass and Z is selected from the group consisting of ##STR29## wherein R 4 , R 5 and R 6 are each independently selected from the group consisting of hydrogen and an alkyl group of 1 to 3 carbon atoms and x is an integer of from zero to 3 with the proviso that the total number of carbon atoms in the radical Z, when Z is the unsaturated group, does not exceed 5 carbon atoms, and m is an integer of from 2 to 5, with (2) a compound of the formula: ##STR30## wherein Y is selected from the group consisting of --O-- and --S-- and each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , and R 2 and R 3 each independently an alkyl group of from 1 to 4 carbon atoms, p is zero or one and m is an integer of from 1 to 4, (b) recovering the resultant solid fraction from the reaction mixture; and (c) heating said solid fraction at a temperature and for a time sufficient to dry said solid fraction.
Claim 31
Dependent Claim
41 words
The method of claim 27 in which the silica is a particulate silica gel having an average particle diameter of from about 20 to about 70 microns and an average pore size of from about 50 to about 500 Angstrom units.
Claim 32
Independent Claim
264 words
A method of preparing a solid phase bonded silica product of the formula: ##STR31## in which ##STR32## is the backbone of a silica gel or controlled pore glass, X is --S--, each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4, which comprises: reacting in the presence of a free radical initiator and a suitable inert organic solvent having a boiling point of at least about 80° C. (1) a bonded phase silica reactant of the formula: ##STR33## wherein n is an integer of from 2 to 5, with (2) a compound of the formula: ##STR34## wherein each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently of alkyl of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4; (3) recovering the resultant solid fraction from the reaction mixture; and (4) heating the solid fraction at a temperature for a time sufficient to dry said solid fraction.
Claim 33
Independent Claim
264 words
A method of preparing a solid phase bonded silica product of the formula: ##STR31## in which ##STR32## is the backbone of a silica gel or controlled pore glass, X is --S--, each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently an alkyl group of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4, which comprises: reacting in the presence of a free radical initiator and a suitable inert organic solvent having a boiling point of at least about 80° C. (1) a bonded phase silica reactant of the formula: ##STR33## wherein n is an integer of from 2 to 5, with (2) a compound of the formula: ##STR34## wherein each R and R 1 are each independently selected from the group consisting of hydrogen, an alkyl group of from 1 to 3 carbon atoms and --CH 2 ) m COOR 3 , R 2 and R 3 are each independently of alkyl of from 1 to 4 carbon atoms, n is an integer of from 2 to 5, p is zero or one and m is an integer of from 1 to 4; (3) recovering the resultant solid fraction from the reaction mixture; and (4) heating the solid fraction at a temperature for a time sufficient to dry said solid fraction.
Claim 34
Dependent Claim
41 words
The method of claim 29 in which the silica is a particulate silica gel having an average particle diameter of from about 20 to about 70 microns and an average pore size of from about 50 to about 500 Angstrom units.
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