Organic compounds -- part of the class 532-570 series – Organic compounds – Amino nitrogen containing
Reexamination Certificate
2000-06-13
2002-08-20
Badio, Barbara P. (Department: 1616)
Organic compounds -- part of the class 532-570 series
Organic compounds
Amino nitrogen containing
C564S292000
Reexamination Certificate
active
06437185
ABSTRACT:
BACKGROUND OF THE INVENTION
1. Field of the Invention
The present invention relates to novel quaternary ammonium compounds, and more particularly to monomeric polyquaternary ammonium derivatives of substituted dipropylene triamine, their process of manufacture, their use in hair care products and in the treatment of fibers and textiles, and preparations containing the quaternary ammonium compounds.
The novel quaternary ammonium compounds of the invention have very high substantivity to fibers such as wool fiber, acrylic fibers, human hair and textiles made of wool and acrylic fibers or mixed fibers, with excellent conditioning and softening effects. By “mixed fibers” is meant a combination of polyester and cotton or rayon fibers, or polyester and wool fibers.
2. Description of the Related Art
Quaternary ammonium compounds are known for a variety of different applications.
U.S. Pat. Nos. 2,654,785 and 2,668,854 to Miescher discloses wholly or partially quaternated azalkane diamines. The quaternary ammonium compounds may be used as medication. The patent further discloses use of diethyl sulfate as a quaternating agent.
U.S. Pat. No. 4,126,562 to Goffinet et al. discloses non-ionic textile softening compositions comprising a cationic surfactant and a non-ionic fabric-conditioning substance selected from fatty acid esters of mono-or polyhydric alcohols having from 1 to 8 carbon atoms and anhydrides thereof. The composition may additionally comprise an insoluble cationic softener selected from di-C10-C22 alkyl quaternary ammonium salts and C8-C25 imidazolinium salts.
U.S. Pat. No. 4,250,112 to Lobach et al. discloses polyalkylenepolyamines containing quaternary dialkylammonium groups and their use as agents for retention of fibers in the manufacture of papers.
U.S. Pat. No. 4,997,912 to Wirtz et al. discloses esters of oxalkylated alkylalkylenediamines, which may be quaternized, obtained by esterifying oxyalkylated alkylalkylenediamines. The compounds are used as corrosion inhibitors in crude oil recovery and treatment plants.
U.S. Pat. No. 4,157,388 to Christiansen discloses polycationic or polyquaternary ammonium ionenes, which generally are hygroscopic. The compounds are useful as conditioning agents for skin, hair and textile products.
U.S. Pat. No. 4,720,383 to Drach et al. discloses imidazolinium compounds used for softening and conditioning fibers, hair and skin. The patent discloses that it is known to prepare softeners comprising quaternaries of ethoxylated or nonethoxylated amido amines derived from the reaction of high molecular weight acid like stearic and a multi amine such as diethylenetriamine. The standard alkylating agents are diethyl sulfate or dimethyl sulfate.
U.S. Pat. No. 4,764,306 to Login discloses a process for the production of bis-quaternary ammonium compounds comprising contacting a tertiary amine with a neutralizing acid, such as HCL, and subsequently contacting the resulting mixture with an epoxide, preferably epihalohydrin or epichlorohydrin. The tertiary amine is preferably stearlyl dimethyl amine or lauryl dimethyl amine. The resulting bis-quaternary ammonium compounds are incorporated into hair conditioners.
U.S. Pat. No. 4,808,321 to Walley discloses liquid fabric softening and antistatic compositions which contain mono-ester analogs of ditallow, dimethyl ammonium chloride.
U.S. Pat. No. 4,913,828 to Caswell et al. discloses alkyl amine-anionic surfactant ion-pair/wax composites useful as fiber, hair and fabric conditioning agents.
U.S. Pat. Nos. 5,087,733 and 5,206,013 to Deppert et al. disclose sulfur containing quaternary ammonium compounds, and their use as hair conditioning agents.
U.S. Pat. No. 5,254,271 to Hamann et al. discloses hair and fabric conditioning compositions comprising mixtures of quaternary ammonium compounds with or without ester groups prepared by reacting amines with dimerized fatty acids and subsequent quaternization or protonation with inorganic or organic acids.
U.S. Pat. Nos. 5,427,773; 5,427,774; and 5,451,394 to Chaudhuri et al. discloses non-irritating, hair, skin and textile substantive, quaternary ammonium salts of paradialkylamino benzamides. These benzamide derivatives are also active sunscreening agents.
U.S. Pat. No. 5,863,526 to Yeung et al. discloses a hair conditioning composition comprising homopolymers prepared from ammonium quaternary salts of amino alkylacrylamides.
U.S. Pat. No. 5,916,863 to Iacobucci et al. discloses a textile softening agent comprising a quaternary ammonium salt which comprises a mixture of mono-, di-, and tri-ester components, having high diester content and low triester content.
The references describe the production of cationic and quaternary ammonium compounds and their use in the treatment of hair, fiber and textiles as softening and conditioning agents. However, none of the references disclose or suggest the specific, novel quaternary ammonium compounds of the invention, a process of preparing same, or the use of such compounds in the treatment of fibrous materials.
Additionally, the substantivity characteristics of the quaternary ammonium compounds of the invention are superior to known quaternary ammonium compounds, and are stable in highly acidic or highly alkaline medium. These properties make the quaternary ammonium compounds of the invention suitable for use in specialized alkaline fiber or hair treatment systems such as in hair straightening treatments, at a high pH of 12.00, and also in permanent waving, at a pH of 9-10. The quaternary ammonium compounds of the invention are stable to these extreme pH conditions. The quaternary ammonium compounds of the invention also have very high substantivity to fibers such as wool fiber, acrylic fibers, human hair and textiles made of wool and acrylic fibers or mixed fibers, with excellent conditioning and softening effects, as shown in Examples 52 and 53 below.
OBJECTS AND SUMMARY OF THE INVENTION
It is an object of the present invention to provide a process for producing quaternary ammonium compounds which are very mild.
It is another object of the invention to provide a process for making quaternary ammonium compounds for use in the treatment of hair, fiber and textile materials.
It is yet another object of the invention to provide a process for making quaternary ammonium compounds for use in hair care products that allow the use and application of thio-based hair treatment specialties and formulations.
It is a further object of the invention to provide a process for making quaternary ammonium compounds which have very high substantivity to fibers such as wool fiber, acrylic fibers, human hair, and textiles made of wool and acrylic fibers or mixed fibers.
Yet another object of the invention is to provide a method for producing quaternary ammonium compounds for use in hair shampoo products which have excellent conditioning effects when used alone or in combination with other surfactants.
Another object of the invention is to provide a method of producing quaternary ammonium compounds which are stable in highly acidic or highly alkaline medium.
It is another object of the invention to provide quaternary ammonium compounds which are excellent conditioners and softeners for fibrous materials.
Yet another object of the invention is to provide quaternary ammonium compounds which are suitable for use in alkaline fiber or hair care systems such as hair straighteners and permanent wave treatments.
These and other objects are accomplished by providing a process for preparing quaternary ammonium compounds, and specifically monomeric, multi-charge, multi-functional quaternary ammonium compounds. These quaternary ammonium compounds are improved as compared to commercially available quaternary ammonium compounds, as they are milder and less irritating to the skin and eyes. Hair care formulations containing the quaternary ammonium compounds of the invention are conditioning and emollient, have very low toxicological profiles, and are not irritating to the skin and eyes.
DETAILED DESCRIPTION OF THE INVENTION
The novel guaternary ammonium compou
Syed Samad A.
Walele Ismail I.
Badio Barbara P.
Finetex, Inc.
Weingram & Associates P.C.
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