Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From reactant having at least one -n=c=x group as well as...
Reexamination Certificate
2001-08-20
2004-10-05
Gorr, Rachel (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From reactant having at least one -n=c=x group as well as...
C528S071000, C554S106000, C560S026000, C560S115000, C560S158000, C424S401000, C424S070110, C424S070280, C424S078030, C424S078170
Reexamination Certificate
active
06800716
ABSTRACT:
FIELD OF THE INVENTION
This invention relates to novel Polymeric Urethane compositions which are obtained by reacting trialkanolamines with hydroxy fatty acids to form mono, di and/or triesters, which are further reacted with diisocyantes to form polymers, which are thereafter quaternized. The resultant polymeric urethane ester quaternary compositions of the present invention exhibit the normal characteristics of existing quaternary compositions such as conditioning, prevention of static charge and softening, emolliency, lubricity, enhanced wet and dry compability, and in addition, increased adhesion to the skin and hair. Also, increased adhesion to the skin and hair occurs as a result of the presence of the urethane linkages directly attributable to the diurethane functionalities which enhance the cationic character of tenacity of the present invention in skin and hair contacting formulations.
BACKGROUND OF THE INVENTION
Quaternary amine-containing compositions have long been in existence and have been used in a myriad of applications. These compositions range from derivatives of tallow such as Dimethyl Di-Hydrogenated Tallow Ammonium Chloride which has been the standard for fabric softeners and as an antistat in fabric spray applications. Quaternaries based on Benzyl Chloride, i.e., Benzylkonium Chloride have been used in conditoners for hair; but the tendency has been to shy away from the Benzene radical, which has some definite irritation and toxicological properties. Quarternaries such as Trimethyl Cetyl ammonium chloride has long been used in hair conditioners for their outstanding compability and antistatic properties. The drawback of the prior art composition is the viscosity which necessitates the addition of water and/or solvents to make the product useable by the cosmetic manufacturer.
In contrast to the art, the compositions according to the present invention bring novel unanticipated properties which can be traced to the presence of the “urethane linkage” within the polymer. This linkage synergistically increased adhesion to hair and skin contacting formulations resulting in the use of less quaternary than those products which are available in the current marketplace, thus resulting in a significant reduction in the cost of manufacturing personal care products. In addition, the use of polyurethane allows the manufacturer a considerable degree of flexibility for formulation due to the viscosity and molecular weight of the composition, which may vary as a function of the polymeric chain size and substituents.
BRIEF DESCRIPTION OF THE INVENTION
One aspect of the present invention relates to a polymeric urethane ester quaternary composition which is made by reacting a trialkanolamine with a hydroxy-containing fatty acid to form a mono-, di- or triester. The ester obtained is then reacted with a diisocyanate as otherwise described herein to produce a polyurethane ester containing tertiary amine groups which tertiary amine groups may be quaternized with a quaternizing agent in optional preferred embodiments according to the present invention. Methods of making and using these compositions are also contemplated by the present invention as are personal care products which include these compositions.
Preferred non-quaternized compositions according to the present invention may be represented by a chemical formula represented by Formula I:
wherein
R
1
is a C
2
to C
12
saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group which is either unsubstituted or substituted with a pendant hydroxyl group, but is preferably unsubstituted;
R
2
is a C
1
to C
24
saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group wherein said hydrocarbon group may be a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or a substituted alkylphenyl or alkylbenzyl group; and
R
3
is a C
2
through C
22
(preferably, C
6
through C
12
) linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group; and
n is an integer from about 2 to 5,000, preferably about 2 to 1000, more preferably about 10 to 500.
Preferred quaternized compositions according to the present invention may be represented by a chemical formula represented by formula II:
wherein
R
1
is a C
2
to C
12
saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group which is either unsubstituted or substituted with a pendant hydroxyl group, but is preferably unsubstituted;
R
2
is a C
1
to C
24
saturated or unsaturated, linear, branch-chained, cyclic or aromatic hydrocarbon group wherein said hydrocarbon group may be a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or a substituted alkylphenyl or alkylbenzyl group;
R
3
is a C
2
through C
22
(preferably, C
6
through C
12
) linear, cyclic or branch-chained saturated or unsaturated hydrocarbon group which is substituted or unsubstituted, an aromatic group, including a phenyl or benzyl group or substituted phenyl or benzyl group, an alkylphenyl, alkylbenzyl or substituted alkylphenyl or alkylbenzyl group;
R
4
is an electron pair (unsubstituted) or a quaternizing group;
R
5
is non-existent (unreacted) or is a counterion to the quaternizing group; and
n is an integer from about 2 to 5,000, preferably about 2 to 1000, more preferably about 10 to 500.
In preferred aspects of the present invention, R
3
is a C
10
hydrocarbon, more preferably a methyl substituted cyclohexyl or isophorone group which is obtained after reaction of isophorone diisocyanate with the trialkanolamine esters. Preferably, R
2
is obtained from the reaction of a fatty acid selected from the group consisting of caproic, caprylic, capric, lauric, myristic, palmitic, stearic, arachadonic acid, linoleic, oleic, linoleic, linolenic, 2-ethylhexoic, isooctanoic, pelargonic, heptanoic, undecanoic, isolauric, isomyristic, isopalmitic, isostearic and mixtures such as those generally known in the art as coconut fatty acids, palm kernal fatty acids, soybean fatty acids, safflower fatty acids, castor oil, etc. In addition to the aforementioned acids, alpha hydroxy acids such as lactic acid, glycolic acid, invention include for example, lactic acid, glycolic acid, alpha hydroxy butyric acid, alpha hydroxy pentanoic acid, alpha hydroxy hexanoic acid, alpha hydroxy heptanoic acid, alpha hydroxy octanoic acid, alpha hydroxy nonanoic acid, alpha hydroxy decanoic acid, alpha hydroxy dodecanoic acid, among others and beta-hydroxy acids such as salicylic acid, among numerous others, as well a ricinoleic and 12-hydroxystearic cid. In more preferred aspects of the present invention, the fatty acid is selected from the group consisting of ricinoleic acid, 12-hydroxystearic acid or mixtures thereof, or representative mixtures of fatty acids obtained from sources (triglycerides) such as castor oil, coconut oil, palm kernel oil, soybean oil, safflower oil, rape seed (canola) oil, among others. Preferred alpha hydroxy acids include lactic acid and glycolic acid. Noted here is the fact that in certain transesterification reactions involving trialkanolamines and triglycerides, the trialkanol fatty ester may represent a mixture of compositions having various fatty acid group substituents.
In particularly preferred aspects of the present invention, the trialkanolamine is triethanolamine, the acid is ricinoleic acid, lactic acid or salicylic acid, or a mixture of any one or more of the aforementioned acids in combinatnion with erucic acid and/or oleic acid. Mixtures of lactic acid and erucic acid or salicylic acid and oleic acid are also preferred for use in the present invention.
The present invention relates to polymeric urethane ester quaternary compositions (“polymeric urethane ester quats”) which are produced by taking trialkanolamines and reacting the
Obeji John
Zofchak Albert
Alzo International
Coleman Sudal Sapone, P.C.
Gorr Rachel
LandOfFree
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