Fatty amines, amidoamines, and their derivatives from natural oil metathesis

Patent metadata

Field	Value
Publication number	US-2016016897-A1
Application number	US-201514867039-A
Country	US
Kind code	A1
Filing date	Sep 28, 2015
Priority date	Oct 25, 2010
Publication date	Jan 21, 2016
Grant date	—

Abstract

Fatty amine compositions made from a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives are disclosed. In another aspect, fatty amidoamines made by reacting a metathesis-derived C10-C17 monounsaturated acid, octadecene-1,18-dioic acid, or their ester derivatives with an aminoalkyl-substituted tertiary amine are disclosed. The fatty amines or amidoamines are advantageously sulfonated, sulfitated, oxidized, or reduced. In other aspects, the ester derivative is a modified triglyceride made by self-metathesis of a natural oil or an unsaturated triglyceride made by cross-metathesis of a natural oil with an olefin.

First claim

1 - 71 . (canceled)

72 . A fatty amine having the formula:
R 2 (R 3 )NR 1
wherein R 1 is —(CH 2 ) 8 —CH═CHR 4 or —(CH 2 ) 8 —CH═CH—(CH 2 ) 8 —NR 2 R 3 ; each of R 2 and R 3 is independently substituted or unsubstituted alkyl, aryl, alkenyl, oxyalkylene, or polyoxyalkylene; and R 4 is hydrogen or C 1 -C 7 alkyl, wherein when R 4 is C 1 -C 7 alkyl, the fatty amine has at least 1 mole % of trans-Δ 9 unsaturation.

73 . A derivative made by one or more of sulfonating, sulfitating, or oxidizing the fatty amine of claim 72 .

74 . The fatty amine of claim 72 wherein the fatty amine has at least 25 mole % of trans-Δ 9 unsaturation.

75 . The fatty amine of claim 72 wherein the fatty amine has at least 50 mole % of trans-Δ 9 unsaturation.

76 . The fatty amine of claim 72 produced from a metathesis-based modified triglyceride or a metathesis-based unsaturated triglyceride.

77 . A glyphosate formulation, a water-soluble herbicide composition, an agricultural solvent, or an anionic emulsifier for agricultural compositions, each comprising the fatty amine of claim 72 .

78 . A glyphosate formulation, a water-soluble herbicide composition, an agricultural solvent, or an anionic emulsifier for agricultural compositions, each comprising the derivative of claim 73 .

79 . A hard-surface cleaner, a laundry detergent formulation, or a personal cleanser or handsoap, each comprising the fatty amine of claim 72 .

80 . A hard-surface cleaner, a laundry detergent formulation, or a personal cleanser or handsoap, each comprising the derivative of claim 73 .

81 . A paraffin dispersant, a gas well foamer, or a corrosion inhibitor, each for use in oilfield applications, each comprising the fatty amine of claim 72 .

82 . A paraffin dispersant, a gas well foamer, or a corrosion inhibitor, each for use in oilfield applications, each comprising the derivative of claim 73 .

83 . A paint or coating additive composition comprising the fatty amine of claim 72 .

84 . A paint or coating additive composition comprising the derivative of claim 73 .

85 . A foamer, foam additive, or dispersant for use in gypsum, concrete, or firefighting applications comprising the fatty amine of claim 72 .

86 . A foamer, foam additive, or dispersant for use in gypsum, concrete, or firefighting applications comprising the derivative of claim 73 .

Assignees

• Stepan Co

Inventors

• Allen Dave R
• Alonso Marcos
• Bernhardt Randal J
• Brown Aaron
• Buchek Kelly
• Luebke Gary
• Luka Renee
• Malec Andrew D
• Masters Ronald A
• Munie Lawrence A
• Murphy Dennis S
• Shapiro Irene
• Skelton Patti
• Sook Brian
• Terry Michael R
• Whitlock Laura Lee
• Wiester Michael
• Wolfe Patrick Shane

Classifications

• C07C309/69 Primary

  of a carbon skeleton substituted by nitrogen atoms, not being part of nitro or nitroso groups · CPC title

• A61K8/42

  Amides · CPC title

• C09K8/584

  characterised by the use of specific surfactants · CPC title

• C08K5/17

  Amines; Quaternary ammonium compounds · CPC title

• C09D7/1233

  Chemistry & Metallurgy · mapped topic