Cleaning compositions for solid surfaces – auxiliary compositions – Cleaning compositions or processes of preparing – For cleaning a specific substrate or removing a specific...
Reexamination Certificate
1999-12-20
2001-03-13
Hardee, John R. (Department: 1751)
Cleaning compositions for solid surfaces, auxiliary compositions
Cleaning compositions or processes of preparing
For cleaning a specific substrate or removing a specific...
C510S130000, C510S500000, C510S515000, C162S076000, C508S284000, C514S399000, C548S349100
Reexamination Certificate
active
06200938
ABSTRACT:
FIELD OF THE INVENTION
The present invention relates to amphoteric surface active agents, and more particularly to amphoteric derivatives of aliphatic polyamines, such as diethylenetriamine and triethylenetetramine reacted with long chain fatty acids, esters or triglycerides. In addition to being novel materials, the amphoteric derivatives of this invention are useful in a variety of applications including the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, as well as in applications for metal working, and lubrication.
BACKGROUND OF THE INVENTION
Amphoteric compositions of various types including derivatives of polyamines are known and have been used over the years for a variety of applications including surfactants in detergent and dishwashing formulations, fabric and paper treating compositions, metal treating and corrosion inhibition, and the like. For example, U.S., Pat. No. 2,999,069 to Masci teaches detergent compositions containing amphoteric derivatives of amidoamines but does not teach or disclose diamide or polyamide compositions having a reactive secondary, internal nitrogen amine site which is carboxyalkylated as provided in the present invention. Liquid dishwashing compositions disclosed in European Patent Application No. 92 203 230.5 to Jadwiga Palicka include amphoteric surface active agents; however, neither diamide nor polyamide compositions having a secondary, internal nitrogen amine site which is carboxyalkylated are disclosed by Palicka. U.S. Pat. No. 5,322,630 to Williams et al. discloses amphoteric derivatives of a broad range of fatty polyamines, fatty amidoamines, fatty imidazoline amines and polyamines which are employed as oilfield corrosion inhibitors. There is, however, no disclosure or suggestion in the Williams patent of the applications of the amphoteric derivatives of the polyamines herein disclosed, including neither the softening/texture modification of substrates such as paper, textiles, human skin surfaces and hair tresses, nor applications for metal working and lubrication.
Furthermore, providing non-irritating softening agents for fabric or paper substrates, or to human skin or hair, has been a long felt need. Fabrics tend to become slightly harsher after wear and laundering. Moreover, untreated personal hygiene facial tissue paper may be harsh and irritating to inflamed tissues, such as nasal orifice skin.
Various attempts have been made to soften fabrics such as suggested in patents directed to fabric softeners, for example, U.S. Pat. No. 3,904,533 of Neiditch for a liquid fabric softener, and U.S. Pat. No. 4,237,155 of Kardouche and U.S. Pat. No. 5,376,287 of Borcher et al which describe antistatic fabric softener sheets, which include fabric-softening agents, such as cationic and nonionic surfactants.
OBJECTS OF THE INVENTION
It is therefore an object of the present invention to define a family of amphoteric compounds comprising derivatives of aliphatic polyamines such as diethylenietriamine and triethylenetetramine wherein the polyamines are first converted to polyamides or imidazoline/amide derivatives thereof.
A further object of the present invention is to define and describe a process by which the above described amphoteric derivatives of aliphatic polyamides [ADAPS] may be made.
It is another object of the present invention to provide an effective softener for various substrates which might contact human skin, as well as skin and hair substrates themselves.
It is a still further object of the present invention to provide amphoteric surface active agents for use in other applications, such as metal working, lubricating, etc.
SUMMARY OF THE INVENTION
The present invention relates to amphoteric derivatives of aliphatic polyamines [ADAPS] that have important industrial and personal care uses, such as, for example, softeners, lubricants, and conditioners, etc. The ADAPs comprise derivatives of compositions which are intermediate aliphatic polyamides or imidazolines, and preferably aliphatic diamides, containing more than one substituent moiety selected from the group consisting of long alkyl chain fatty acids, esters and triglycerides, such as derived from animal, vegetable or synthetic sources ranging in molecular distribution from butyric through erucic acids. (e.g. milkfat, soybean oil, rapeseed oil).
The intermediate amide compound is then converted into an amphoteric compound by reacting it with unsaturated carboxylic acids, halogenated carboxylic acids, carboxylated epoxy compounds or in the case of the higher polyamines, acid anhydrides or polycarboxylic acids.
The carboxyalkylation step of the present invention attaches an alkyl carboxylic acid functional group to at least one secondary internal amine nitrogen atom, thereby forming the amphoteric products of the present invention. The amphoteric product is thus a polyamide or imidazoline derivative of the aliphatic polyamine starting material.
Compounds containing acidic functional groups suitable for use in reacting with aliphatic polyamides in accordance with the present invention include alkyl carboxyl groups [i.e., carboxylic acid functional moiety, COOH] where the carboxylic acid is derived from one or more unsaturated or halogenated carboxylic acids, carboxylated epoxy compounds, acid anhydrides and/or polycarboxylic acids with the proviso that the amphoteric composition must contain at least one ionizable nitrogen site. For the purposes of the present invention such above-mentioned unsaturated carboxylic acids, halogenated acids, carboxylated epoxy compounds, acid anhydrides or polycarboxylic acids, comprise an amphoteric forming group because the product produced by reacting with one of the acids is an amphoteric product.
DETAILED DESCRIPTION OF THE INVENTION
Consistent with the above discussion, a first specific group of ADAPs of the present invention may comprise amphoteric derivatives of diethylenetriamine [DETA] wherein the amphoteric derivatives of the present invention are prepared by first reacting DETA as a starting material with at least one member selected from long-alkyl-chain plant, animal or synthetic derived fatty acids, esters and triglycerides, such as, for example, compositions containing substituted or unsubstituted, branched or straight chain, saturated or unsaturated alkyl chain groups ranging in molecular distribution from butyric through erucic acids, that is, containing from 3 to 21 carbon atoms in addition to the carbonyl group.
An intermediate substituted DETA predominately diamide (preferably) or polyamide is thus formed having fatty alkyl moieties of 3 to 21 carbon atoms.
Amphoteric forming agents suitable for use in reacting with aliphatic polyamides in accordance with the present invention include alkyl carboxyl groups (i.e., carboxylic acid functional moiety, COOH] where the carboxylic acid is one or more unsaturated or halogenated carboxylic acids, or carboxylated epoxy compounds. Exemplary suitable amphoteric forming agents include vemolic acid, acrylic acid, itaconic acid, chloroacetic acid, maleic anhydride, octadecenyl anhydrides and adipic acid.
The ADAPS of the present invention also comprise a second group of compounds analogous to the above described DETA derivatives, that are amphoteric derivatives of triethylene tetramine [TETA]. The foregoing discussion applies to TETA just as it does to DETA.
As with the DETA derivatives, the amphoteric TETA derivatives also have more than one substituent which includes those derived from long alkyl-chain plant, animal or synthetic derived fatty acids, esters and triglycerides, ranging in molecular distribution from butyric through erucic acids (4-22 carbon atoms) with long length fatty alkyl amide moieties having from 3 to 21 carbon atoms.
In the case of higher polyamides the polyamide TETA derivatives are made amphoteric by reacting them with a member of the above-discussed amphoteric forming agent group, consisting of unsaturated carboxylic acids, halogenated carboxylic acids,
Katstra Richard D.
Komor Joseph A.
Perella James e.
Hardee John R.
Lehrer Norman E.
Mona Industries, Inc.
Schoenberg Franklyn
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