Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
2000-06-08
2001-12-18
Hightower, P. Hampton (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C528S310000, C528S320000, C528S328000
Reexamination Certificate
active
06331607
ABSTRACT:
BACKGROUND OF THE INVENTION
Antimicrobial agents obtained by reacting N-substituted propylenediamines with 2-aminoglutaric acid esters are known from DE-A1 3410956 (Henkel). The amides formed in this reaction, which are marketed as Glucoprotamin®, may optionally be derivatized with alkylene oxides and/or acids. An overview of the antimicrobial properties of these substances was published in Hyg. Med. 17, 529 (1992). In addition, the use of Glucoprotamin® as a virucidal agent is known from DE-A1 4340124 (Ecolab).
Unfortunately, the known aminoglutaric acid ester amides have the disadvantage that concentrates, i.e. aqueous preparations thereof with an active substance content of about 20 to 50% by weight, are often neither color-stable nor storage-stable. On the contrary, the concentrates tend to thicken in storage, to separate crystals and to turn cloudy.
Accordingly, the complex problem addressed by the present invention was to provide a simple process by which glucoprotamines with excellent color quality, which would combine a low viscosity after dilution with water with improved storage stability, could be obtained in a high yield and selectivity.
BRIEF SUMMARY OF THE INVENTION
The present invention includes a process for the production of antimicrobial agents of the glucoprotamine type using aminosilicones and to their use as antifoam agents glucoprotamines by condensation of N-substituted propylene-diamines with 2-aminoglutaric compounds, characterized in that the reaction is carried out in the presence of aminosilicones.
It has surprisingly been found that the presence of aminosilicones not only reduces foaming during the condensation reaction, which is desirable from the point of view of process technology, it also leads to an increase in the volume/time yield. Through the inhibition of foaming, the elimination of water can be very closely controlled so that the exact degree of condensation required can be obtained.
In addition, it had not been expected that this measure would also lead to products distinguished by a much lighter color and distinctly improved stability in storage in relation to the prior art.
DETAILED DESCRIPTION OF THE INVENTION
N-substituted Propylenediamines
The N-substituted propylenediamnes to be used as starting materials preferably correspond to formula (I):
R
1
-NH-CH
2
CH
2
CH
2
NH
2
(I)
in which R
1
is a linear alkyl group containing 6 to 22 carbon atoms and, more particularly, 12 to 14 carbon atoms. They may be obtained by the conventional methods of organic synthesis, for example by reaction of the corresponding alkylamines with acrylonitrile and subsequent hydrogenation [cf. for example FR-B 1351793]. N-substituted propylenediamines where the alkyl group contains 12 to 14 carbon atoms, the C
12
component preferably making up from 65 to 70 mole-%, have proved successful from the applicational point of view.
2-Aminoglutaric Derivatives
The 2-aminoglutaric derivatives suitable for use as the second component preferably correspond to formula (II):
in which R
2
is hydrogen or a C
1-4
alkyl group. Processes for their production are described, for example, in DE-AS 2158562, DE-OS 1493991 and DE-AS 1254635. D- or L-glutamic acid or racemates thereof are normally used, the L form preferably being used. Instead of the acid, its methyl, ethyl, propyl or butyl ester may also be used. If free glutamic acid is used, the condensation reaction may be carried out in the absence of a solvent and the water formed during the reaction may be directly distilled off.
Condensation Reaction
The condensation reaction is carried out in known manner, i.e. the N-substituted propylenediamnes and the 2-aminoglutaric derivatives are normally used in a molar ratio of 1:1 to 1:2. It is generally carried out at temperatures of 60 to 175° C. and is preferably carried out at temperatures in the range from 100 to 150° C.
Aminosilicones
The aminosilicones to be used in accordance with the invention are commercially available substances. Polymers containing 50 to 2,000, preferably 100 to 1,000 and more preferably 200 to 800 monomer units corresponding to formulae (IIIa) and (IIIb):
in which R
3
and R
4
independently of one another represent alkyl groups containing 1 to 8 carbon atoms, R
5
and R
6
independently of one another represent optionally hydroxysubstituted alkylene groups containing 1 to 8 carbon atoms and n is 0 or a number of 1 to 3, are preferably used. Aminosilicones corresponding to formula (III) which have a nitrogen content of 0.1 to 5 and more particularly 0.5 to 2% by weight are particularly preferred. These silicone compounds may be produced, for example, by equilibration of organopolysiloxanes and aminofunctional silanes or siloxanes, as described in U.S. Pat. No. 4,584,125. Suitable organopolysiloxanes are, for example, hexamethyl cyclotrisiloxane, octamethyl cyclotrisiloxane, trimethylsiloxy-terminated dimethyl or diethyl polysiloxanes. Examples of suitable aminofunctional siloxanes are &ggr;-aminopropyl trimethoxysilane, &ggr;-aminopropyl triethoxysilane and N-(&bgr;-aminoethyl)&ggr;-aminopropyl trimethoxysilane. The aminosilicones are normally used in quantities of 0.0001 to 0.2, preferably 0.001 to 0.1 and more preferably 0.01 to 0.05% by weight, based on the glucoprotamine. Another advantage of the process according to the invention is that there is no need to use organic entraining agents to remove water, as described in EP-B1 0156275, so that the outlay on equipment involved in production is significantly reduced.
Commercial Applications
The glucoprotamines obtainable by the process according to the invention are far lighter in color than the prior art products so that colorless application solutions can be prepared for the first time. In contrast to the hitherto known processes, the presence of aminosilicones during the production process makes it possible to obtain even more concentrated active-substance solutions which have distinctly improved stability in storage and a lower viscosity due to the absence of unwanted polymers which can easily flocculate. Accordingly, the present invention also relates to the use of aminosilicones as antifoam agents and stabilizers in the condensation of N-substituted propylenediamnes with 2-aminoglutaric derivatives.
REFERENCES:
patent: 3702313 (1972-11-01), Gilch et al.
patent: 3770807 (1973-11-01), Sumikawa et al.
patent: 4584125 (1986-04-01), Griswold et al.
patent: 4652585 (1987-03-01), Gerhardt et al.
patent: 4652858 (1987-03-01), Kokubo et al.
patent: 5352756 (1994-10-01), Meldal
patent: 5824708 (1998-10-01), Disch et al.
patent: 1 254 635 (1967-11-01), None
patent: 1 493 991 (1969-10-01), None
patent: 21 58 562 B2 (1972-06-01), None
patent: 34 10 956 A1 (1985-09-01), None
patent: 39 30 410 A (1991-03-01), None
patent: 43 40 124 A1 (1995-06-01), None
patent: 0 156 275 A2 (1985-10-01), None
patent: 1 351 793 B (1963-12-01), None
K. Disch, “Glucoprotamin—a New Antimicrobial Substance1”, Hyg. Med., 17, No. 12, (1992), pp. 529-534.
Bohlander Ralf
Jaensch Sven
Springer Dirk
Cognis Deutschland GmbH
Drach John E.
Ettelman Aaron R.
Hampton Hightower P.
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