Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2001-11-19
2004-08-17
Truong, Duc (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S310000, C528S332000, C528S345000, C528S354000
Reexamination Certificate
active
06777527
ABSTRACT:
TECHNICAL FIELD
The present invention relates to alkoxylated, condensed basic amino acid-containing polymers and a process for their production.
BACKGROUND OF THE INVENTION
Ethoxylated polyamines, especially polyethyleneimines and processes for their production are known, cf. U.S. Pat. No. 3,313,736, U.S. Pat. No. 4,891,160, U.S. Pat. No. 4,551,506 and WO-A-97/23546. The ethoxylated polyamines are for example used in cleaning compositions.
DE-A-2 227 546 relates to the use of alkoxylated polyalkyleneimines for the dehydration of crude oils. The alkoxylated polyalkyleneimines are prepared by a two-stage process in which, in the first stage, one mole of an alkylene oxide, based on one mole of NH groups in the polyethyleneimine, is reacted with a polyalkylenepolyamine in the presence of water with formation of hydroxyalkyl groups. In the second process stage water is initially removed from the reaction mixture, an alkaline catalyst added, alkylene oxide forced in and the reaction carried out under pressure at temperatures between 125° and 135° C. From 10 to 300 alkylene oxide units are added per NH group. Alternatively, the alkoxylation can be carried out in a single stage, by forcing in alkylene oxide in the presence of aqueous or anhydrous alkaline catalysts and causing it to react under pressure with polyethyleneimines at temperatures between 125 and 135° C.
EP-A-0,112,593 relates to detergent formulations containing ethoxylated amines. In this case the preparation of the alkoxylated amines likewise takes place in two stages, a hydroxyethylated polyethyleneimine being produced in the first stage by the action of ethylene oxide and the necessary amount of ethylene oxide being added in the second stage by further addition of ethylene oxide at temperatures ranging from 130 to 140° C. under super-atmospheric pressure. The degree of ethoxylation is for example from 15 to 42.
WO-A-97/20879 relates to a process for the preparation of hydroxyalkylated polyethyleneimines by hydroxyalkylation of polyethyleneimines in one or two procedural stages to form reaction products which contain 1 to 200 mol of alkylene oxide groups per NH group in the polyethyleneimine. In the one-stage process, there are anhydrous polyethyleneimines and 1 to 200 mol %, in relation to the polyethyleneimines, of at least one anhydrous base, or aqueous solutions of said substances are dehydrated and after removing all the water are reacted at temperatures above 135-150° C. with at least one alkylene oxide. Alternatively, in the two-stage process, in the first stage polyethyleneimine is reacted at temperatures from 80 to 100° C. with 0.7 to 0.9 mol, in relation to one mole of NH groups in the polymer, of at least one alkylene oxide in an aqueous solution, and in the second stage the reaction product obtained in the first step in reacted in the presence of 1 to 20 mol %, in relation to polyethyleneimine, of an alkaline catalyst in the absence of water at temperatures from 120 to 150° C. with at least one alkylene oxide to form hydroxyalkylated polyethyleneimines which contain 1 to 200 mol of alkylene oxide groups per NH group in the polyethyleneimine. The resulting alkoxylated products are only slightly colored.
U.S. patent application Ser. No. 09/131,234 relates to an amino acid based polymer, oligomer or copolymer containing at least 5 mol % of units of a basic amino acid selected from the group consisting of lysine, arginine, ornithine; tryptophan and mixtures thereof and at least about 5 mol % of a polymerizable compound selected from the group consisting of aliphatic or cycloaliphatic amines, alicyclic amines, diamines, triamines, tetraamines, aliphatic amino alcohols or mixtures thereof. The said polymers, oligomers or copolymers are obtained by condensing said basic amino acids at a temperature of at least 120° C. with at least one of said polymerizable compounds. The condensation products may be used as additives for detergents and/or other laundry additives.
U.S. patent application Ser. No. 09/131,282 relates to condensation products of basic amino acids with copolymerizable compounds which are obtained by condensing
(a) a basic amino acid selected from the group consisting of lysine, arginine, ornithine, tryptophan and mixtures thereof,
(b) a copolymerizable compound selected from the group consisting of saturated monobasic carboxylic acids, unsaturated mono-basic carboxylic acids, polybasic carboxylic acids, carboxylic anhydrides, diketenes, monohydroxycarboxylic acids, polyhydroxycarboxylic acids and mixtures thereof, and optionally
(c) at least one compound selected from the group consisting of amines, lactams, non-proteinogenic amino acids, alcohols, alkoxylated alcohols, alkoxylated amines, amino sugars, carbohydrates and sugar carboxylic acids
in a molar ratio of (a):(b) of from 100:1 to 1:1 at a temperature of at least 120° C. The condensation products may be used as an additive in detergents.
It is an object of the present invention to provide new condensation products of basic amino acids.
SUMMARY OF THE INVENTION
We have found that the above object is achieved with alkoxylated, condensed basic amino acid-containing polymers comprising the addition products of alkylene oxides with
homocondensates of basic amino acids,
condensates of mixtures of two or more basic amino acids and
cocondensates of basic amino acids and cocondensable compounds.
We have found that the object is also achieved with a process for the production of alkoxylated, condensed basic amino acid-containing polymers by reacting
homocondensates of basic amino acids,
condensates of mixtures of two or more basic amino acids and
cocondensates of basic amino acids and cocondensable compounds
with at least one alkylene oxide selected from the group consisting of C
2
- to C
30
-alkylene oxides and styrene oxide. The alkoxylated, condensed basic amino acid-containing polymers may be used as additives for detergents.
DETAILED DESCRIPTION OF THE INVENTION
In order to produce condensed basic amino acid-containing polymers, basic amino acids are preferably condensed thermally. Other methods for the production of basic amino acid-containing polymers are based on chemical methods (e.g. via N-carboxy anhydrides of the basic amino acids) or on microorganisms. Basic amino acids, which are hereinafter referred to as compounds of group (a), are lysine, arginine, ornithine, tryptophan and their mixtures. These compounds may be used in the form of their hydrates, their esters with lower alcohols or their salts, for instance their sulfates, hydrochlorides or acetates. The esters of the basic amino acids are preferably derived from monovalent C
1
to C
4
-alcohols such as methanol, ethanol, n-propanol, isopropanol, n-butanol, sec.-butanol or tert-butanol. When hydrochlorides are used, approximately equivalent quantities of a base should be added to the reaction mixture for neutralization of hydrogen chloride. Sodium hydroxide and potassium hydroxide are the preferred bases. If a monohydrochloride of a basic amino acid is used, one equivalent of a base is necessary, whereas in the case of dihydrochlorides two equivalents are required. Lysine hydrate and aqueous solutions of lysine are preferably used as basic amino acid. Lysine can also be used in the form of its cyclic lactam, i.e. &agr;-amino-t-caprolactam.
Compounds which are cocondensable with basic amino acids are hereinafter referred to as compounds of group (b), for example compounds having at least one carboxyl group, carboxylic anhydrides, diketenes, amines, lactams, alcohols, alkoxylated alcohols and alkoxylated amines. Carboxyl-containing compounds are for instance saturated monobasic carboxylic acids, unsaturated monobasic carboxylic acids, polybasic carboxylic acids, monohydroxycarboxylic acids, monobasic polyhydroxycarboxylic acids, non-proteinogenic amino acids and mixtures thereof. Examples of saturated monobasic carboxylic acids are formic acid, acetic acid, propionic acid, butyric acid, valeric acid, capric acid, octanoic acid, nonanoic acid, decanoic acid, lauric acid, palmitic acid, st
Boeckh Dieter
Borzyk Oliver
Mohr Bernhard
BASF - Aktiengesellschaft
Oblon & Spivak, McClelland, Maier & Neustadt P.C.
Truong Duc
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