Biodegradable surfactants and related compositions, methods and systems

Patent metadata

Field	Value
Publication number	US-11066359-B2
Application number	US-201816484817-A
Country	US
Kind code	B2
Filing date	Feb 8, 2018
Priority date	Feb 10, 2017
Publication date	Jul 20, 2021
Grant date	Jul 20, 2021

Abstract

Biodegradable surfactants are described, in which an amphiphilic heteroatom containing hydrocarbon optionally comprising at least one counterion (Z), and related compositions, methods and systems. Biodegradable surfactant described herein has an aHLB value in accordance with equation (1): aHLB=20*Gh/(Gh−Gt) (1) wherein Gh is the Group Number of a hydrophilic head portion of the biodegradable surfactant optionally comprising the at least one counterion (Z), and Gt is the Group Number of a hydrophobic tail portion of the biodegradable surfactant. A biodegradable surfactant in the sense of the disclosure can be tuned to a set hydrophilic-lipophilic balance (aHLB) by selectively modifying at least one tuning moiety of the biodegradable surfactants to provide tuned biodegradable surfactants having an increase or decrease in their adjusted hydrophilic-lipophilic balance (aHLB).

First claim

The invention claimed is:

1. A method of modifying a tunable biodegradable surfactant having a first aHLB value to obtain a tuned biodegradable surfactant having a second aHLB value, the method comprising:
providing the tunable biodegradable surfactant having the first aHLB value, the tunable biodegradable surfactant comprising an amphiphilic heteroatom containing hydrocarbon and optionally at least one counterion (Z), the amphiphilic heteroatom containing hydrocarbon comprising
a hydrophilic head portion of containing a maximum number of a hydrophilic functional group with a positive Group Number on the hydrocarbon the hydrophilic function group comprising at least one tunable moiety, and
a hydrophobic tail portion containing the maximum number of a hydrophobic group of atoms with a negative Group Number on the hydrocarbon and forming a contiguous terminal section of the biodegradable surfactant; and
modifying the at least one tunable moiety of the tunable biodegradable surfactant to obtain the tuned biodegradable surfactant comprising at least one tuned moiety and having the second aHLB value and optionally the at least one counterion (Z),

wherein the amphiphilic heteroatom containing hydrocarbon has Formula (X):

in which
represents a single or double bond when R21 is H, and a single bond when R21 is other than H;
X is selected from one of O, NH, or NCH3;
Y is selected from C2-C8 linear or branched alkyl, C4-C8 cycloalkyl, C2-C8 linear or branched heteroalkyl, C4-C8 heterocycloalkyl, C4-C8 heteroalkyl heterocycloalkyl, C4-C8 aryl alkyl, C4-C8 alkyl aryl, C4-C8 heteroaryl alkyl, and C4-C8 alkyl heteroaryl groups, optionally substituted with 1-6 tuning moieties independently selected from sulfate, sulfonate, phosphate, phosphonate, carboxylate, amine, C1-C2 alkyl amine, C1-C2 dialkyl amine, C1-C2 trialkyl ammonium, pyridinium, hydroxyl, acetyloxy, C1-C2 alkoxy;
R20 is a C11-C21 linear or branched alkyl, alkenyl, or alkynyl group; and
R21 is selected from H, sulfate, sulfonate, phosphate, phosphonate, carboxylate, amine, C1-C2 alkyl amine, C1-C2 dialkyl amine, C1-C2 trialkyl ammonium, pyridinium, hydroxyl, acetyloxy, C1-C2 alkoxy; and
the at least one counterion (Z) is selected from the group selected from the group consisting of proton, ammonium, C-C4 tetraalkyl ammonium, sodium (I), potassium (I), cesium (I), magnesium (II), calcium (II), zinc (II), inorganic sulfate (SO 4 2− ), inorganic phosphate (PO 4 3− ), tetrafluorborate, hexafluorophospate, p-toluenesulfonate, benzenesulfonate, nitrate, trifluoroacetate, fluoride, chloride, bromide, and iodide or any combinations thereof;

wherein the at least one counterion (Z) is selected from the group selected from the group consisting of proton, ammonium, C-C4 tetraalkyl ammonium, sodium (I), potassium (I), cesium (I), magnesium (II), calcium (II), zinc (II), inorganic sulfate (SO 4 2- ), inorganic phosphate (PO 4 3- ), tetrafluorborate, hexafluorophospate, p-toluenesulfonate, benzenesulfonate, nitrate, trifluoroacetate, fluoride, chloride, bromide, and iodide or any combinations thereof;
and wherein
aHLB= 20* G h /( G h −G t )  (1)

in which
G h is the Group Number of the head portion of the amphiphilic heteroatom containing hydrocarbon,
G t is the Group Number of the tail portion of amphiphilic heteroatom containing hydrocarbon.

2. The method of claim 1 , further comprising:
providing a look-up table containing a list of Group Numbers each corresponding to a reference moiety,
calculating a head-portion Group Number of the at least one tuned moiety,
identifying the at least one tuned moiety having the head-portion Group Number from the look-up table, and
converting the at least one tunable moiety of the tunable biodegradable surfactant into the at least one tuned moiety.

3. The method of claim 1 , wherein the first aHLB value is in a range of 5-10 and the second aHLB value is in a range of 15-20.

4. The method of claim 1 , wherein when the first aHLB is in the range of 5-10, the at least one tuned moiety is independently selected from acetyloxy, or C1-C2 alkoxy.

5. The method of claim 1 , wherein when the first aHLB value is in the range of 15-20, the at least one tuned moiety is independently selected from sulfate, sulfonate, phosphate, phosphonate having at least one counter ion selected from the group consisting of proton, ammonium, C-C4 tetraalkyl ammonium, sodium (I), potassium (I), cesium (I), magnesium (II), calcium (II), zinc (II) or any combinations thereof.

6. The method of claim 1 , wherein the tunable biodegradable surfactant has Formula (XX):

in which
represents a single or double bond when Q is H, and a single bond when Q is other than H;
n is 1-6;
A is a node moiety selected from C2-C8 linear or branched alkyl, C4-C8 cycloalkyl, C2-C8 linear or branched heteroalkyl, C4-C8 heterocycloalkyl, C4-C8 heteroalkyl heterocycloalkyl, C4-C8 aryl alkyl, C4-C8 alkyl aryl, C4-C8 heteroaryl alkyl, and C4-C8 alkyl heteroaryl group,
T each is a tuning moiety each independently selected from OH, or NH 2 ;
Q is selected from H, OH, or NH 2 ;
R10 is H, or C1-C2 alkyl group;
R20 is a C11-C21 linear or branched alkyl, alkenyl, or alkynyl group;
the R22 and each of R12 groups are independently selected from H, sulfate, sulfonate, phosphate, phosphonate, carboxylate, C1-C2 alkyl amine, C1-C2 dialkyl amine, C1-C2 trialkyl ammonium, pyridinium, acetyloxy, C1-C2 alkoxy; and

and the tuned biodegradable surfactant has Formula (XXII),

in which
represents a single or double bond when R22 is H, and a single bond when R22 is other than H;
n is 1-6;
A is a node moiety selected from C2-C8 linear or branched alkyl, C4-C8 cycloalkyl, C2-C8 linear or branched heteroalkyl, C4-C8 heterocycloalkyl, C4-C8 heteroalkyl heterocycloalkyl, C4-C8 aryl alkyl, C4-C8 alkyl aryl, C4-C8 heteroaryl alkyl, and C4-C8 alkyl heteroaryl group,
each is a tuning moiety each independently selected from OH, or NH 2 ;
Q is selected from H, OH, or NH 2 ;
R10 is H, or C1-C2 alkyl warn;
R20 is a C11-C21 linear or branched alkyl, alkenyl, or alkynyl group;
the R22 and each of R12 groups are independently selected from H, sulfate, sulfonate, phosphate, phosphonate, carboxylate, C1-C2 alkyl amine, C1-C2 dialkyl amine, C1-C2 trialkyl ammonium, pyridinium, acetyloxy, C1-C2 alkoxy;
and wherein the at least one counterion (Z) is selected from the group selected from the group consisting of proton, ammonium, C-C4 tetraalkyl ammonium, sodium (I), potassium (I), cesium (I), magnesium (II), calcium (II), zinc (II), inorganic sulfate (SO 4 2− ), inorganic phosphate (PO 4 3- ), tetrafluorborate, hexafluorophospate, p-toluenesulfonate, benzenesulfonate, nitrate, trifluoroacetate, fluoride, chloride, bromide, and iodide or any combinations thereof.

7. The method of claim 1 , wherein the tunable biodegradable surfactant has Formula (XXI),

In which
represents a single or double bond when Q is H, and a single bond when Q is other than H;
n is 1-6,
T each is a tuning moiety each independently selected from OH, or NH 2 ;
Q is a selected from H, OH, or NH 2 ;
R10 is H, or C1-C2 alkyl group; and
R20 is a C11-C21 linear or branch

Assignees

• L Livermore Nat Security Llc

Inventors

• Lyman Mathew Gerald
• Dugan Lawrence
• Leif Roald N
• Rubinfeld Bonnee
• Souza Brian E
• Valdez Carlos A

Classifications

• A61K8/375

  the alcohol moiety containing more than one hydroxy group · CPC title

• A61K2800/596

  Mixtures of surface active compounds · CPC title

• A61Q5/02

  Preparations for cleaning the hair · CPC title

• A61Q11/00

  Preparations for care of the teeth, of the oral cavity or of dentures; Dentifrices, e.g. toothpastes; Mouth rinses · CPC title

• A61K8/42

  Amides · CPC title