Humic acid derivatives and methods of preparation and use

Patent metadata

Field	Value
Publication number	US-2016108010-A1
Application number	US-201314894660-A
Country	US
Kind code	A1
Filing date	May 28, 2013
Priority date	May 28, 2013
Publication date	Apr 21, 2016
Grant date	—

Abstract

Disclosed are antioxidative natural compounds, their salts, chelates and cleavage derivatives that exhibit a superior combination of properties. The compounds can be used for a variety of purposes, including the stabilization of polymers. The compounds can be prepared by substantially cleaving a humic acid of formula I followed by esterification to provide at least one antioxidant compounds of formula V, formula VI, formula VII, formula VIII, salts thereof, or chelates thereof.

First claim

1 . A stabilizing compound comprising at least one compound of formula V, formula VI, formula VII, formula VIII:

R 2 is hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 4 is hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 11 is —N(R 111 )(R 112 ), wherein R 111 is C-acetamido or substituted C-acetamido; R 112 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 12 , R 141 , R 142 , R 143 , and R 144 are independently hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 13 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 16 is a hydrogen, glucuronate or substituted glucuronate;
R 21 , R 22 , R 31 , R 32 , and R 41 are independently hydrogen, —(C 4 -C 20 )alkyl, or substituted —(C 4 -C 20 )alkyl;
R 23 , R 24 , R 25 , R 26 , R 27 , R 33 , R 34 , R 35 , R 36 , R 42 , R 43 , and R 44 are independently hydrogen, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl; and
R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 are independently hydrogen, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl; and
wherein at least one of R 141 , R 142 , R 143 , R 144 , R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 is not hydrogen; at least one of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 is not hydrogen; at least one of R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 , is not hydrogen; and at least one of R 41 , R 42 , R 43 , and R 44 is not hydrogen;
a salt thereof, chelate thereof, or combination thereof.

2 . The compound of claim 1 , comprising at least one compound of formula VI, formula VII, formula VIII, a salt thereof, chelate thereof, or combination thereof,
wherein R 2 is hydrogen or —(C 1 -C 20 )alkyl; R 23 , R 24 , R 25 , R 26 , and R 27 , are independently hydrogen or —(C═O)—(C 3 -C 19 )alkyl;
R 4 is hydrogen or —(C 1 -C 20 )alkyl;
R 41 is independently hydrogen or —(C 4 -C 20 )alkyl; and
R 42 , R 43 , and R 44 are independently hydrogen or —(C═O)—(C 3 -C 19 )alkyl,
wherein at least one of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , R 27 R 41 , R 42 , R 43 and R 44 is not hydrogen.

3 . The compound of claim 1 , wherein the compound is formula V, a salt thereof, or chelate thereof.

4 . The compound of claim 3 wherein
R 11 is —N(R 111 )(R 112 ), wherein R 111 is C-acetamido or substituted C-acetamido; R 112 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 12 , R 141 , R 142 , R 143 , and R 144 are independently hydrogen, —(C 4 -C 20 )alkyl, or substituted —(C 4 -C 20 )alkyl;
R 13 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 are independently hydrogen, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl; and
R 16 is a hydrogen, glucuronate or substituted glucuronate;
wherein at least one of R 141 , R 142 , R 143 , R 144 , R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 is not hydrogen.

5 . The compound of claim 3 wherein R 141 , R 142 , R 143 , and R 144 are independently hydrogen or —(C 4 -C 20 )alkyl.

6 . The compound of claim 3 wherein R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 are independently hydrogen or —(C═O)—(C 3 -C 19 )alkyl.

7 . (canceled)

8 . The compound of claim 3 wherein
R 2 is hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 21 , R 22 , are independently hydrogen, —(C 4 -C 20 )alkyl, or substituted —(C 4 -C 20 )alkyl;
R 23 , R 24 , R 25 , R 26 , and R 27 , are independently hydrogen, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl; and
wherein at least one of R 21 , R 22 , R 23 , R 24 , R 25 , R 26 , and R 27 is not hydrogen.

9 .- 13 . (canceled)

14 . The compound of claim 8 , wherein
R 31 , R 32 , are independently hydrogen, —(C 4 -C 20 )alkyl, or substituted —(C 4 -C 20 )alkyl; R 33 , R 34 , R 35 , and R 36 , are independently hydrogen, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl; and wherein at least one of R 31 , R 32 , R 33 , R 34 , R 35 , and R 36 is not hydrogen.

15 . The compound of claim 8 , wherein R 31 and R 32 , are independently hydrogen or —(C 4 -C 20 )alkyl.

16 . The compound of claim 8 , wherein R 33 , R 34 , R 35 , and R 36 are independently hydrogen or —(C═O)—(C 3 -C 19 )alkyl.

17 .- 22 . (canceled)

23 . The compound of claim 1 , wherein the compound is a lithium salt, sodium salt, ammonium salt, potassium salt, calcium salt, barium salt, magnesium salt, manganese salt, zinc salt, aluminum salt, iron salt, or a combination thereof.

24 . (canceled)

25 . The compound of claim 1 , wherein the at least one compound is a polyvalent cation chelate.

26 . The compounds of claim 1 , wherein the at least one compound is independently a calcium chelate, magnesium chelate, iron chelate, or zinc chelate or combination thereof.

27 . A method of preparing a polymer stabilizing mixture of compounds, the method comprising:
substantially hydrolyzing a humic acid to form a mixture of compounds; and esterifying at least one functional group of the mixture of compounds to give a polymer stabilizing mixture of compounds.

28 . The method of claim 27 , wherein forming the mixture of compounds comprises forming a mixture of at least one compound of formulas V-VIII, a salt thereof, or chelate thereof:

wherein:
R 11 is —N(R 111 )(R 112 ), wherein R 111 is C-acetamido or substituted C-acetamido; R 112 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 12 is hydrogen, —(C 4 -C 20 )alkyl, or substituted —(C 4 -C 20 )alkyl;
R 13 is hydrogen, —(C 1 -C 20 )alkyl, substituted —(C 1 -C 20 )alkyl, —(C═O)—(C 3 -C 19 )alkyl, or substituted —(C═O)—(C 3 -C 19 )alkyl;
R 16 is hydrogen, glucuronate, or substituted glucuronate;
R 2 is hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 4 is hydrogen, —(C 1 -C 20 )alkyl, or substituted —(C 1 -C 20 )alkyl;
R 21 , R 22 , R 31 , R 32 , R 41 , R 23 , R 24 , R 25 , R 26 , R 27 , R 33 , R 34 , R 35 , R 36 , R 42 , R 43 , R 44 , R 141 , R 142 , R 143 , R 144 , R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 are hydrogen; and
esterifying at least one of R 21 , R 22 , R 31 , R 32 , R 41 , R 23 , R 24 , R 25 , R 26 , R 27 , R 33 , R 34 , R 35 , R 36 , R 42 , R 43 , R 44 , R 141 , R 142 , R 143 , R 144 , R 151 , R 152 , R 153 , R 154 , R 155 , and R 156 .

29 . (canceled)

30 . (canceled)

31 . (canceled)

32 . The method of claim 27 , further comprising forming a chelate of at least one compound of the polymer stabilizing mixture with a calcium cation, magnesium cation, zinc cation, iron cation, or combinations thereof.

33 . (canceled)

34 . The method of clai

Assignees

• Empire Technology Dev Llc

Inventors

• Adam Georgius Abidal
• Needham Anita

Classifications

• C09K15/30

  containing heterocyclic ring with at least one nitrogen atom as ring member · CPC title

• C08K5/1535

  Five-membered rings · CPC title

• C08K5/357

  Six-membered rings · CPC title

• C09K15/06

  containing oxygen · CPC title

• C07D307/91

  Dibenzofurans; Hydrogenated dibenzofurans · CPC title