IP Library Granted Patent US 8,361,779
Granted Patent B2
US 8,361,779 · App. 12/953,569 · Granted Jan 29, 2013

Buffer compounds

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Quick Facts
Patent No.
US 8,361,779
App. No.
12/953,569
Granted
Jan 29, 2013
Kind
B2
Abstract

A method of buffering a chemical or biological composition, comprising adding to the composition an effective buffering amount of at least one protonated or un-protonated amine-quaternary ammonium compound having a general formula: wherein the variables R, G, n and k are as defined herein.

Claims (33)

1. A method of buffering a chemical or biological composition, comprising adding to the composition an effective buffering amount of at least one protonated or un-protonated amine-quaternary ammonium compound having a general formula:

wherein:

n has integer values in the range 0-4,

k is 0 for the un-protonated compound and k is 1 for the protonated compound;

each G 1 , G 3 and G 5 is a chemical moiety independently selected from —H, —CH 3 , —C 2 H 5 , or is a component of a cyclic chemical moiety,

each G 2 and G 4 is a chemical moiety independently selected from —H, —CH 3 , —CH 2 OH, —C 2 H 5 , —CO 2 H, —SO 3 H, —PO 3 H 2 , —CO 2 − , —SO 3 − , —PO 3 H − , and —PO 3 2− , or is a component of the cyclic chemical moiety,

each G 6 is a chemical moiety independently selected from —H, —CH 3 , —CH 2 OH, —C 2 H 5 , —OH, —OCH 3 , —CO 2 H, —SO 3 H, —PO 3 H 2 , —CO 2 − , —SO 3 − , —PO 3 H − , and —PO 3 2− , or is a component of the cyclic chemical moiety and

each R 1 , R 2 , R 3 , R 4 and R 5 is a chemical moiety independently selected from —CH 3 , —C 2 H 5 , —CH(CH 3 ) 2 , -cyclohexyl, —C 2 H 4 OH, —C 2 H 4 OCH 3 , —(CH 2 ) 2-3 NHC(O)CH 3 , —(CH 2 ) 2-3 N(CH 3 )C(O)CH 3 , —(CH 2 ) 1-3 C(O)NH 2 , —(CH 2 ) 1-3 C(O)NHCH 3 , —(CH 2 ) 1-3 C(O)N(CH 3 ) 2 , —CH 2 (CG 5 G 6 ) m SO 3 − , —CH 2 (CG 5 G 6 ) m CO 2 − , —CH 2 (CG 5 G 6 ) m CO 2 H, —CH 2 (CG 5 G 6 ) m PO 3 2− , —CH 2 (CG 5 G 6 ) m PO 3 H − , —CH 2 (CG 5 G 6 ) m PO 3 H 2 with m being 0, 1, 2 or 3, or is a component of the cyclic chemical moiety, or R 5 is a chemical moiety —[CG 7 G 8 -(CG 7 G 9 ) r -CG 7 G 8 -H j NR 6 R 7 ] j+ , wherein each G 7 is a chemical moiety independently selected from —H, —CH 3 , —C 2 H 5 , each G 8 is a chemical moiety independently selected from —H, —CH 3 , —CH 2 OH, —C 2 H 5 , —CO 2 H, —SO 3 H, —PO 3 H 2 , —CO 2 − , —SO 3 − , —PO 3 H − , and —PO 3 2− , G 9 is a chemical moiety independently selected from —H, —CH 3 , —CH2, —OH, —C 2 H 5 , —OH, —OCH 3 , —CO 2 H, —SO 3 H, —PO 3 H 2 , —CO 2 − , —SO 3 − , —PO 3 H − , and —PO 3 2− , r has integer values in the range 0-4, and j is 0 or 1, and each R 6 and R 7 is a chemical moiety independently selected from —CH 3 , —C 2 H 5 , —CH(CH 3 ) 2 , -cyclohexyl, —C 2 H 4 OH, —C 2 H 4 OCH 3 , —(CH 2 ) 2-3 NHC(O)CH 3 , —(CH 2 ) 2-3 N(CH 3 )C(O)CH 3 , —(CH 2 ) 1-3 C(O)NH 2 , —(CH 2 ) 1-3 C(O)NHCH 3 , —(CH 2 ) 1-3 C(O)N(CH 3 ) 2 , —CH 2 (CG 5 G 6 ) m SO 3 − , —CH 2 (CG 5 G 6 ) m CO 2 − , —CH 2 (CG 5 G 6 ) m CO 2 H, —CH 2 (CG 5 G 6 ) m PO 3 2− , —CH 2 (CG 5 G 6 ) m PO 3 H − , —CH 2 (CG 5 G 6 ) m PO 3 H 2 , with m being 0, 1, 2 or 3;

wherein when the compound comprises the cyclic chemical moiety, the cyclic chemical moiety is one or more selected from (a), (b), (c), (d), (e), (f) and (g):

(a) one or more pair of R 1 and R 2 , R 3 and R 4 , R 3 and R 5 , and/or R 4 and R 5 , forms a single chemical moiety such that the pair is individually and independently —CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH(OH)CH(OH)CH 2 —, —CH 2 CH 2 CH 2 CH 2 CH 2 —, —CH 2 CH 2 OCH 2 CH 2 —, —CH 2 CH 2 CH(OH)CH 2 CH 2 —, —CH 2 CH 2 N(C(O)G 1 )CH 2 CH 2 —, —CH 2 C(O)N(G 1 )CH 2 CH 2 —, —CH 2 CH(OH)CH(OH)CH 2 —, ═C(NG 1 2 ) 2 ,

(b) one or more pair of R 1 and R 3 , R 1 and R 4 , R 1 and R 5 , R 2 and R 3 , R 2 and R 4 and/or R 2 and R 5 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 2 ) g - with n being 0 or 1 and g being 2 or 3;

(c) one or more pair of G 1 and G 3 , G 2 and G 4 , G 1 and G 4 and/or G 2 and G 3 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 6 ) q - with q having integer values 0-4 and the sum of q and n having integer values 3-4, and, when q=0, —(CG 1 G 6 ) 0 - is a single carbon-carbon bond between the carbon atoms to which the pair is attached in the general formula;

(d) one or more pair of G 1 and G 2 , G 3 and G 4 , and/or G 5 and G 6 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 6 ) w - with w having integer values 4-5;

(e) one or more pair of R 1 and G 3 , R 1 and G 4 , R 2 and G 3 , R 2 and G 4 , R 3 and G 1 , R 3 and G 2 , R 4 and G 1 , R 4 and G 2 , R 5 and G 1 , and/or R 5 and G 2 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 2 ) s - with s having integer values 1-3, n having integer values 0-2 and the sum of s and n having integer values 2-3;

(f) one or more pair of R 1 and G 5 , R 1 and G 6 , R 2 and G 5 , R 2 and G 6 , R 3 and G 5 , R 3 and G 6 , R 4 and G 5 , R 4 and G 6 , R 5 and G 5 , and/or R 5 and G 6 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 2 ) v - with v having integer values 0-3, n having integer values 1-4 and the sum of v and n having integer values 3-4 and, when v=0, —(CG 1 G 2 ) 0 - is a single carbon-carbon bond between the carbon atoms to which the pair is attached in the general formula; and

(g) one or more pair of R 1 and G 1 , R 1 and G 2 , R 2 and G 1 , R 2 and G 2 , R 3 and G 3 , R 3 and G 4 , R 4 and G 3 , R 4 and G 4 , R 5 and G 3 , and/or R 5 and G 4 forms a single chemical moiety such that the pair is individually and independently —(CG 1 G 2 ) u - with u having integer values 3-4;

wherein CI is a non-interfering counter-ion or mixture of non-interfering counter-ions as needed to maintain electroneutrality, with the charge on the amine-quaternary ammonium compound being equal to the value of quantity (j+k−z+1) wherein z equals the absolute value of the numerical sum of all negative charges on each —CO 2 − , —SO 3 − , —PO 3 H − , and —PO 3 2− moiety contained within the R 1 , R 2 , R 3 , R 4 , R 5 , R 6 , R 7 , G 2 , G 4 , G 6 G 8 and/or G 9 present, and

wherein d equals |j+k−z+1| for monovalent counter-ions, |j+k−z+1|/2 for divalent counter-ions, |j+k−z+1|/3 for trivalent counter-ions, |j+k−z+1|/4 for tetravalent counter-ions and the sign of (z−j−k+1) reflects the charge on the counter-ion(s), except that when (j+z−k+1) is zero, d is zero and no separate counter-ion is present.

2. A method as defined in claim 1 wherein CI is a non-interfering anion or a mixture of non-interfering anions selected from Cl − , Br − , I − , OH − , F − , OCH 3 − , HCO 2 − , CH 3 CO 2 − , CF 3 CO 2 − , NO 3 − , ClO 4 − , BF 4 − , PF 6 − , HSO 4 − , HCO 3 − , H 2 PO 4 − , CH 3 OCO 2 − , CH 3 OSO 3 − , CH 3 SO 3 − , CF 3 SO 3 − , H 2 PO 3 − , CH 3 PO 3 H − , HPO 3 2− , CH 3 PO 3 2− , CO 3 2− , SO 4 2− , HPO 4 2− and PO 4 3− .

3. A method as defined in claim 1 wherein CI is a non-interfering cation or a mixture of non-interfering cations selected from: Li + , Na + , K + , Rb + , Cs + , NH 4 + , Ag + , Ti + , Mg 2+ , Ca 2+ , Sr 2+ , Ba 2+ , VO 2+ , Mn 2+ , Fe 2+ , Co 2+ , Ni 2+ , Cu 2+ , Zn 2+ Cd 2+ , Hg 2+ , Eu 2+ , UO 2 2+ , Pb 2+ , Al 3+ , Ga 3+ , Y 3+ , BiO 3+ , La 3+ , Ce 3+ , Pr 3+ , Nd 3+ , Sm 3+ , Eu 3+ , Gd 3+ , Tb 3+ , Dy 3+ , Ho 3+ , Er 3+ , Tm 3+ , Yb 3+ , Lu 3+ and Th 4+ .

4. A method as defined in claim 1 wherein CI is a non-interfering cation or a mixture of non-interfering cations selected from: a protonated primary alkyl or hydroxyalkyl amine, a protonated secondary alkyl or hydroxyalkyl amine, a protonated tertiary alkyl or hydroxyalkyl amine, a diprotonated alkyl, alkylene, hydroxyalkyl or hydroxyalkylene diamine, a quaternary alkyl or hydroxyalkyl ammonium compound, an alkyl or hydroxyalkyl sulfonium compound, an alkyl or hydroxyalkyl sulfoxonium compound, a quaternary alkyl or hydroxyalkyl phosphonium compound and a di-quaternary alkyl, alkylene, hydroxyalkyl or hydroxyalkylene ammonium compound, wherein the foregoing alkyl, alkylene, hydroxyalkyl and hydroxyalkylene groups contain one to three carbon atoms, and wherein the cation or the mixture of cations is not a compound as defined in claim 1 .

5. A method as defined in claim 1 wherein CI is a non-interfering buffering anion, a mixture of non-interfering buffering anions, a non-interfering buffering cation or a mixture of non-interfering buffering cations, with pKa value(s) in the range 2-12, and wherein CI is not an amine-quaternary ammonium compound as defined in claim 1 .

6. A method as defined in claim 1 wherein CI is a non-interfering buffering anion, a mixture of non-interfering buffering anions, a non-interfering buffering cation or a mixture of non-interfering buffering cations, with pKa value(s) in the range 1-13, and wherein CI is an amine-quaternary ammonium compound as defined in claim 1 , and has a charge conferring electroneutrality on the compound.

7. A method as defined in claim 1 wherein the compound comprises the cyclic moiety as defined in (a), wherein the cyclic moiety has one of the following structures:

wherein G 1 and other components of the compound are as defined as in claim 1 .

8. A method as defined in claim 1 wherein the compound comprises the cyclic moiety as defined in (a), wherein the cyclic moiety has one of the following structures:

wherein G 1 and other components of the compound are as defined as in claim 1 .

9. A method as defined in claim 1 wherein the compound comprises the cyclic moiety as defined in (b), wherein the compound has one of the following structures:

wherein each of G 1 , G 1 , G 2 , G 3 , G 4 , G 5 , R 2 , R 4 and R 5 is independently defined as in claim 1 .

10. A method as defined in claim 1 wherein the compound comprises the cyclic moiety as defined in (c), wherein the compound has one of the following structures:

wherein each of G 1 , G 1 , G 2 , G 3 , G 4 , G 5 , G 6 , R 1 , R 2 , R 3 , R 4 and R 5 is independently defined as in claim 1 .

11. A method as defined in claim 1 wherein the compound comprises the cyclic moiety as defined in (e) wherein the compound has one of the following structures:

wherein each of G 1 , G 1 , G 2 , G 3 , G 4 , G 5 , G 6 , R 1 , R 2 , R 3 , R 4 and R 5 is independently defined as in claim 1 .

Assignments (5)
SECURITY INTEREST Recorded Aug 4, 2026
From: SACHEM, INC.
To: FIRST BUSINESS SPECIALTY FINANCE, LLC
Reel/Frame 075521/0429 →
RELEASE OF SECURITY INTEREST Recorded Jun 10, 2025
From: PNC BANK, NATIONAL ASSOCIATION
To: SACHEM, INC.; SACHEM ASIA, INC.
Reel/Frame 071368/0642 →
SECURITY INTEREST Recorded May 6, 2024
From: SACHEM, INC.; SACHEM ASIA, INC.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 067318/0340 →
FIRST AMENDMENT TO PATENT, TRADEMARK AND COPYRIGHT SECURITY AGREEMENT Recorded May 5, 2014
From: SACHEM, INC.; SACHEM ASIA, INC.
To: PNC BANK, NATIONAL ASSOCIATION
Reel/Frame 032817/0478 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Nov 24, 2010
From: HAYMORE, BARRY L.
To: SACHEM, INC.
Reel/Frame 025418/0543 →