Synthetic resins or natural rubbers -- part of the class 520 ser – Synthetic resins – From carboxylic acid or derivative thereof
Reexamination Certificate
1997-08-29
2001-06-05
Mosley, Terressa (Department: 1711)
Synthetic resins or natural rubbers -- part of the class 520 ser
Synthetic resins
From carboxylic acid or derivative thereof
C510S109000, C510S458000
Reexamination Certificate
active
06242559
ABSTRACT:
FIELD OF THE INVENTION
This invention is directed to processes for making polymeric compounds and more particularly to methods for making hydroxy fatty acid polymers and methods of using the same.
BACKGROUND OF THE INVENTION
Surface active agents can be prepared by reacting hydrophobic molecules, such as C10-C22 chain length alcohols, acids or olefins, with various reactants to produce surface active molecules. The resultant compounds can have cationic, anionic, nonionic and amphoteric natures. The compounds find a variety of uses, for example, in textiles, cosmetics, leather treatments, household detergents and other applications. Typically, surface active agents based on cetyl, stearate, oleate, tallow, and behenyl compounds give high levels of lubricity to a given surface.
As the length of the carbon chain increases from C10 to C22, however, the melting points of the compounds increase, and one must increase the strength of hydrophilic group to maintain the desired HLB balance, its ability to be oil or water soluble, or dispersible in oil and water. Further, these products do not provide the same level of the properties provided by silicone-based products at the same percentage of solid concentration. This is particularly true for amino silicones, reactive silicones and elastomeric silicones on a variety of surfaces. These compounds also can have limited long term stability in emulsion formulations.
Most of the surface active agents which show good smoothness and lubricity when applied on textile fibers and fabrics make the surface hydrophobic, i.e, wetting by water is poor. For example, fabric softeners when used in household laundry or mill finishing can make the fabric smooth and silky, but can also lead to poor water uptake, thereby reducing the comfort level of the treated fabrics.
Also, most of these surface active agents which impart smoothness and softness are not water soluble or capable of forming microemulsions on their own. Rather, they form large particle sizes (1-2 microns), which may be a disadvantage at lower levels of application.
SUMMARY OF THE INVENTION
The present invention provides methods for making poly(hydroxy acid) long chain functional molecules having carboxyl and hydroxyl groups. The present invention also provides methods for using the molecules as base materials of various chain lengths which can be reacted with various reactants to form surface active agents which can be cationic, anionic, nonionic or amphoteric in nature.
The present invention of making polymeric surface active molecules overcomes numerous disadvantages of various surface active agents produced by the prior art. For example, the resultant polymers can be branched, and accordingly the melting point of the polymer can drop, despite increasing chain length. Thus the present invention can provide polymeric long chain compounds having improved stabilization, lubricity, solubility, dispersiblility, surface activity, and the like.
The products of the invention can be useful in numerous applications, for example, in textiles, leather, cosmetics, oil industry, detergents, emulsion polymerization and other fields in which conventional emulsifiers are used.
DETAILED DESCRIPTION OF THE INVENTION
The present invention provides methods for producing long chain hydroxy fatty acid based polymers. The resultant long chain hydroxy fatty acid polymers can be reacted with suitable reactants or functionalizing agents to produce a variety of novel surface active agents. The resultant surface active agents can be cationic, anionic, nonionic and/or amphoteric, depending upon the subsequent reaction.
In the invention, at least one long chain hydroxy fatty acid having at least one carboxyl and at least one hydroxyl functionality is polymerized by esterification to make longer chain polyester polymers (referred to herein as poly(hydroxy acid) polymers) having at least one hydroxy and at least one carboxyl group. Polyesters derived from hydroxy fatty acids can be obtained by heating the hydroxy fatty acid, or a mixture of such acids, optionally in the presence of an esterification catalyst, until the required polyester has been obtained. The esterification preferably is conducted at temperatures ranging from about 120° C. to about 280° C. under reflux conditions for 30 minutes or longer until the desired level of conversion is achieved.
The preferred molecular weight range of the resultant poly(hydroxy acid) is from about 300 to about 3000. The preferred degree of polymerization is from about 1.0 to about 10, more preferably from about 2.0 to about 2.5 and from about 4 to about 4.5, depending upon the specific application of the end product. The degree of polymerization can be controlled by monitoring the acid number value and/or water of esterification of the reaction mixture periodically during esterification. For example, the acid number of the reaction mixture can be periodically measured during esterification so that the reaction can be stopped when the acid number is within the desired range, preferably from about 175 to about 5. For example, the acid value of 12-hydroxy stearic acid is about 170-175, and the acid value of the reaction mixture can be about 5 after polymerization. Water is formed in the esterification reaction and is removed from the reaction mixture, for example, by passing a stream of nitrogen over the reaction mixtures, or by carrying out the reaction in the presence of a solvent such as toluene or xylene and azeotropically removing the water as it is formed.
Acid number is a well known value associated with the acid strength of a substance and is defined as the milligrams (mgs) of KOH required to neutralize the acid in a one gram sample of the product being measured. The higher the amount of acid in the sample, the more KOH needed to neutralize the acid and the higher the acid number.
The resultant polymer or oligomer is then reacted at hydroxyl, carboxyl, or both functionalities, with any of a variety of reactants to impart excellent surface active properties thereto.
A preferred class of long chain hydroxy fatty acids useful in the production of poly(hydroxy acids) in accordance with the invention have the following formula:
wherein:
each R′ and R″ is independently selected from (CH
2
)
m
, in which each m is an integer from 1 to 18. Hydroxy fatty acids useful to form the poly(hydroxy acid) compounds preferably contain from 10 to 22 carbon atoms. Exemplary hydroxy fatty acids include, but are not limited to, 5-hydroxy dodecanoic acid, 5-hydroxyhexadeanoic acid, 12-hydroxy stearic acid (12-HSA), and the like. Mixtures of hydroxy fatty acids can also be used.
The polymeric or oligomeric poly(hydroxy acids) can be reacted using standard reactants according to conventional industrial practice to convert a hydroxyl group, or a carboxyl group, or both, on a pendent hydrocarbon chain to produce a variety of cationic, anionic, nonionic and amphoteric surface active agents. For example, the poly(hydroxy acid) can be reacted with amines or polyamines at the carboxyl groups. Such compounds could be further alkylated to make a quaternary amine of poly(hydroxy acid). The preferred type amines are of the following structure:
C
n
H
m
NR
1
R
2
wherein:
n is an integer from 1 to 10;
m is an integer from 3 to 23;
and each R
1
and R
2
can be the same or different and is independently selected from hydrogen or C1 to C10 alkyl.
Preferably, the organic amine is a polyfunctional amine, and more preferably a polyalkylene polyamine. Exemplary polyalkylene polyamines include those including at least one reactive —NH or —NH2 group, and having the general formula:
R
3
R
3
N—[A—B]
n
—A—NR
3
R
3
wherein:
each R
3
can be the same or different and is independently selected from hydrogen or C1 to C10 alkyl, which can be unsubstituted or monosubstituted with C1 to C4 alkoxy or cyano group;
n is an integer from 0 to 100;
each A is the same or different and is independently selected from C2 to C4 alkylene or hydroxyalkylene; and
B is O, S, or NR
3
, with R
3
having the definition des
Alston & Bird LLP
Mosley Terressa
Zydex Industries
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