US5248333A
Expired / Lapsed
US
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Mixtures of fatty acid alkylene diamides, fatty acid esters and metal soaps, and their use as additives in plastics
Assignee: Neynaber Chemie GmbH
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Filing: 1990-05-10
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Granted: 1993-09-28
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Expires: 2010-05-10
Abstract
Abstract Mixtures of light colored bis(C 8 -C 22 fatty acid) alkylene diamides, C 8 -C 22 fatty acid esters, and, if desired, metal soaps of C 8 -C 22 fatty acids can be obtained if, in a melt containing fatty acids with 8 to 22 carbon atoms, a part of the fatty acids are condensed to the corresponding fatty acid diamides with diamines of the general formula NH 2 --R--NH 2 , in which R is a straight chain, branched, or cyclic alkylene group with 2 to 12 carbon atoms; a part of the fatty acids are esterified with fatty alcohols with 8 to 22 carbon atoms and/or multifunctional alkanols with 2 to 15 carbon atoms and 2 to 6 hydroxyl groups; and, if desired, a part of the fatty acids are converted to the corresponding metal soaps with basic compounds of divalent metals. The condensation with the diamines is carried out before the esterification of the fatty acids with fatty alcohols and/or multifunctional alkanols. The mixtures so obtained can be used as additives in plastics.
Inventors
- 👤 Kurt Worschech
- 👤 Erwin Fleischer
- 👤 Peter Wedl
- 👤 Frido Loeffelholz
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-11-05 23:18
CPC Classifications
C; C08; C08K; C08K5/00; C08K5/16; C08K5/20; C07; C07C; C07C231/00; C07C231/02
Claims Analysis
Total Claims: 22
Claim 1
Independent Claim
204 words
A process for the preparation of mixtures of light-colored bis(C 8 -C 22 -fatty acid) alkylenediamides and C 8 -C 22 -fatty acid esters and, optionally, metal soaps of C 8 -C 22 -fatty acids, said process comprising: (A) reacting a part of the fatty acid in a melt containing fatty acid or acids having 8 to 22 carbon atoms with diamines of the general formula NH.sub.2 --R--NH.sub.2 in which R is a linear, branched or cyclic alkylene group having 2 to 12 carbon atoms, to give the corresponding fatty acid diamides, the amount of fatty acid present in said melt being in excess of the amount stoichiometrically required to react with all the diamines also present in the melt; (B) esterifying at least a part of the remaining fatty acid or acids with alcohols selected from the group consisting of fatty alcohols having 8 to 22 carbon atoms and polyfunctional alkanols having 2 to 15 carbon atoms and 2 to 6 hydroxyl groups; and, optionally, (C) reacting at least a part of the remaining fatty acid or acids with basic compounds of divalent metals to give the corresponding metal soaps, the condensation reaction step (A) being carried out before the esterification step (B).
Claim 2
Dependent Claim
204 words
A process for the preparation of mixtures of light-colored bis(C 8 -C 22 -fatty acid) alkylenediamides and C 8 -C 22 -fatty acid esters and, optionally, metal soaps of C 8 -C 22 -fatty acids, said process comprising: (A) reacting a part of the fatty acid in a melt containing fatty acid or acids having 8 to 22 carbon atoms with diamines of the general formula NH.sub.2 --R--NH.sub.2 in which R is a linear, branched or cyclic alkylene group having 2 to 12 carbon atoms, to give the corresponding fatty acid diamides, the amount of fatty acid present in said melt being in excess of the amount stoichiometrically required to react with all the diamines also present in the melt; (B) esterifying at least a part of the remaining fatty acid or acids with alcohols selected from the group consisting of fatty alcohols having 8 to 22 carbon atoms and polyfunctional alkanols having 2 to 15 carbon atoms and 2 to 6 hydroxyl groups; and, optionally, (C) reacting at least a part of the remaining fatty acid or acids with basic compounds of divalent metals to give the corresponding metal soaps, the condensation reaction step (A) being carried out before the esterification step (B).
Claim 3
Dependent Claim
24 words
The process as claimed in claim 1, wherein saturated fatty acid or acids having 16 to 22 carbon atoms, or mixtures thereof, are reacted.
Claim 4
Dependent Claim
24 words
The process as claimed in claim 1, wherein diamines selected from the group consisting of ethylenediamine, tetramethylenediamine and hexamethylenediamine are reacted in step (A).
Claim 5
Dependent Claim
32 words
The process as claimed in claim 1, wherein 2.2 to 10, moles of the fatty acid or acids present in the melt are employed in the condensation reaction per mole of diamine.
Claim 6
Dependent Claim
50 words
The process as claimed in claim 1, wherein the fatty acid diamides, fatty acid esters and, if present, the metal soaps in the melt after reaction steps (A), (B), and, if performed, (C), are present in ratios by weight to one another of 4 to 6:1 to 2:2 to 4.
Claim 7
Dependent Claim
27 words
The process as claimed in claim 1, wherein the fatty acids and diamines are subjected to a condensation reaction at a temperature of 140° to 190° C.
Claim 8
Dependent Claim
29 words
The process as claimed in claim 1, wherein the condensation reaction is terminated when the amine number of the reaction mixture has reached a value of less than 1.
Claim 9
Dependent Claim
26 words
The process as claimed in claim 1, wherein step (B) is performed at melt temperatures of 150° to 190° C. in the presence of esterification catalysts.
Claim 10
Dependent Claim
26 words
The process as claimed in claim 1, wherein saturated fatty alcohols having 12 to 22 carbon atoms are used for the esterification of the fatty acids.
Claim 11
Dependent Claim
46 words
The process as claimed in claim 1, wherein polyfunctional alkanols from the group composed of ethylene glycol, propylene glycol, glycerol, diglycerol, triglycerol, tetraglycerol, trimethylolpropane, di-trimethylolpropane, pentaerythritol and di-pentaerythritol are used for the esterification and are reacted with the fatty acids to give complete or partial esters.
Claim 12
Dependent Claim
25 words
The process as claimed in claim 1, wherein a reaction to give metal soaps is carried out at melt temperatures of 150° to 160° C.
Claim 13
Dependent Claim
44 words
The process as claimed in claim 1, wherein a reagent selected from the group consisting of oxides, hydroxides and carbonates of Mg, Ca, Ba, Cd, Zn and Pb, and mixtures thereof is used for the formation of the metal soaps of the fatty acids.
Claim 14
Dependent Claim
41 words
The process as claimed in claim 1, wherein, before the condensation reaction and any formation of other metal soaps, a zinc soap of the fatty acids is added to the melt containing the fatty acids or is generated in this melt.
Claim 15
Dependent Claim
41 words
The process as claimed in claim 1, wherein the fatty acid diamides and fatty acid esters and, optionally, metal soaps from the group consisting of Mg, Ca, Ba, Cd and Pb soaps, are generated successively in the melt containing fatty acids.
Claim 16
Dependent Claim
45 words
The process as claimed in claim 1, wherein further C 8 -C 22 -fatty acids are added to the melt containing the fatty acid diamides and the esters of the fatty acids with polyfunctional alkanols, before a reaction with the basic compounds of divalent metals.
Claim 17
Dependent Claim
63 words
The process as claimed in claim 1 for the preparation of mixtures containing zinc soaps, wherein fatty acids, zinc soaps or basic zinc compounds, and, optionally, basic compounds of other divalent metals, and also diamines and fatty alcohols or polyfunctional alkanols are reacted in molar ratios with one another to give acid numbers within the range from 5 to 20 in the mixtures.
Claim 18
Dependent Claim
50 words
Mixtures consisting essentially of light-colored bis-(C 8 -C 22 -fatty acid) alkylenediamides and esters of C 8 -C 22 -fatty acids, and, optionally, metal soaps, said mixtures having ratios by weight of alkylenediamides to fatty acids esters and, if present, metal soaps of 4 to 6:1 to 2:2 to 4.
Claim 19
Dependent Claim
50 words
Mixtures consisting essentially of light-colored bis-(C 8 -C 22 -fatty acid) alkylenediamides and esters of C 8 -C 22 -fatty acids, and, optionally, metal soaps, said mixtures having ratios by weight of alkylenediamides to fatty acids esters and, if present, metal soaps of 4 to 6:1 to 2:2 to 4.
Claim 20
Dependent Claim
16 words
The process as claimed in claim 14, wherein a calcium soap is generated in the melt.
Claim 21
Dependent Claim
28 words
The process according to claim 6, wherein the fatty acids and diamines are subjected to a condensation reaction at temperatures in the range from 160° to 180° C.
Claim 22
Dependent Claim
32 words
The process as claimed in claim 4, wherein 2.5 to 4 moles of the fatty acid or acids per mole of diamine employed in the condensation reaction are present in the melt.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1996-09-27 | 1997-03-29 | 1997-09-28 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 2000-09-27 | 2001-03-29 | 2001-09-28 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 2004-09-27 | 2005-03-29 | 2005-09-28 | $7700.00 | Window Closed / Lapsed |