CA2294400A1 - Process for improving the odor of commercial solvent used in fabric softening compositions - Google Patents

Abstract

Commercially available 2,2,4-trimethyl-1,3-pentanediol is processed by reduction, hydrogenation, recrystallization, ion exchange treatment, fractional distillation, base treatment, aqueous extraction, vacuum stripping, nitrogen sparging, or combinations thereof to improve its odor by reducing the gas phase concentrations of odorant materials typically found in commercially available 2,2,4-trimethyl-1,3-pentanediol. The resulting 2,2,4-trimethyl-1,3-pentanediol having improved odor is employed in various fabric softening compositions.

Description

PROCESS FOR IMPROVING THE ODOR OF COMMERCIAL SOLVENT
USED IN FABRIC SOFTENING COMPOSITIONS
TECHNICAL FIELD
The present invention relates to processes for improving the odor of certain commercially available solvents and the resulting compositions. Specifically, processes for improving the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol and the resulting compositions are provided that solve problems that have previously gone unnoticed, particularly for clear or translucent liquid fabric softening compositions.
BACKGROUND OF THE INVENTION
As a well-known compound, 2.2,4-trimethyl-1,3-pentanediol is used in a variety of contexts. For instance, 2,2,4-trimethyl-1,3-pentanediol has been used in surface coating and unsaturated polyester resins, as an intermediate for synthetic lubricants and polyurethane elastomers and foams, and as a part of glycol mixtures to improve rosin solubility in inks. See KIRK-OTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY (3d ed. 1978). As used in such industrial products, the offensive odor typically associated with commercially available 2,2,4-trimethyl-1,3-pentanediol does not adversely affect the acceptability of such products when incorporated therein, since the acceptability of such products does not largely depend on the odor of the product.
It has recently been found that 2,2,4-trimethyl-1,3-pentanediol is a useful solvent in consumer products such as fabric softening compositions. See Trinh et al., PCT Patent Application Nos. W09703169-A1 and W09703170-A1, both published on January 30, 1997, said documents being incorporated herein by reference. In consumer products such as fabric softeners, the acceptability of the product depends largely on the pleasant odor of the product. However, a problem with using 2,2,4-trimethyl-1,3-pentanediol as a solvent in consumer products relates to the offensive odor typically associated with commercially available 2,2,4-trimethyl-1,3-pentanediol. Consumer products containing commercially available 2,2,4-trimethyl-1,3-pentanediol usually suffer from unacceptable odor problems which are related to the use of 2,2,4-trimethyl-1,3-pentanediol.
Therefore, industry, especially the consumer products industry, continues to seek ways in which to incorporate commercially available 2,2,4-trimethyl-1,3-pentanediol in consumer products, particularly fabric softening products, without the products suffering from unacceptable odor problems related to the use of 2,2,4-trimethyl-1,3-pentanediol.
It has now been discovered that commercially available 2,2,4-trimethyl-1,3-pentanediol can be processed so that its offensive odor is significantly reduced and so _7_ that it can be used in a consumer product, especially fabric softening products, without imparting an unacceptable odor effect to the product.
SUMMARY OF THE INVENTION
The present invention relates to processes for improving the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol by reducing the gas phase concentrations) of one or more odorant materials typically found in commercially available 2,2,4-trimethyl-1,3-pentanediol. The processes utilized in the present invention to reduce the gas phase concentrations of odorant materials typicaiiy found in commercially available 2,2,4-trimethyl-1,3-pentanediol include, but are not limited to, reduction, hydrogenation, recrystallization, ion exchange treatment, fractional distillation. base treatment, aqueous extraction, vacuum stripping, nitrogen sparging, and combinations of the processes described herein.
The present invention also encompasses the compositions resulting from the processes described herein to remove odorant materials from commercially available 2,2,4-trimethyl-1,3-pentanediol. Additionally, the present invention relates to fabric softening compositions containing commercially available 2,2,4-trimethyl-1,3-pentanediol which has been processed according to the present invention.
DETAILED DESCRIPTION OF THE INVENTION
I Commercial ~ ~ 4-Trimethyl-1 3-Pentanediol Having Improved Odor The compound 2,2,4-trimethyl-1,3-pentanediol is commercially available from the Eastman Chemical Company. As a commercial material, 2,2,4-trimethyl-1,3-pentanediol typically contains one or more odorant materials which have been found to contribute to the offensive odor usually associated with commercially available 2,2,4-trimethyl-1,3-pentanediol. Specifically, it has been found that commercially available 2,2,4-trimethyl-1,3-pentanediol contains one or more odorant materials, including, but not limited to: isobutyl aldehyde, isobutyric acid, 2,2,4-trimethyl-3-keto-pentanol, 2,2,4-trimethyl-3-keto-pentanol isobutyrate, diisopropyl ketone, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, and mixtures of such odorant materials.
The odorant materials described herein are characterized as having offensive and/or repulsive odors. Isobutyl aldehyde has been described as having an "extremely diffusive, penetrating odor, pungent and - undiluted - unpleasant, sour, repulsive." See Steffen Arctander, PERFUME AND FLAVOR CHEMICALS, Vol. I, No. 548 (1969).
Isobutyric acid has been described as having a "powerful, diffusive sour (acid) odor, slightly less repulsive and less buttery than n-Butyric acid." See Steffen Arctander, PERFUME AND FLAVOR CHEMICALS, Vol. I, No. S50 (1969). Diisopropyl ketone has been described as having a "powerful and diffusive ethereal-fruity, pungent odor."
See Steffen Arctander, PERFUME AND FLAVOR CHEMICALS, Vol. I, No. 1090 (1969).
The compound 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate is available from - the Eastman Chemical Company under the trade name Texanol0. This monoester of 2,2,4-trimethyl-1,3-pentanediol is used as a coalescing aid in flat and semigloss latex paint formulations. See KIRK-UTHMER ENCYCLOPEDIA OF CHEMICAL TECHNOLOGY (3d ed. 1978). A "solvent" odor is typically associated with commercially available Texanol~ due to impurities found in the commercial material. However, as a pure substance, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate has a more acceptable odor due to its low volatility resulting from its high molecular weight.
It is preferable that the gas phase concentrations) of at least one or more of these odorant materials which are found in commercially available 2,2,4-trimethyl-1,3-pentanediol be significantly reduced in order to improve the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. As a result of reducing the gas phase concentrations of one or more of these odorant materials, consumer products containing 2,2,4-trimethyl-1,3-pentanediol will typically achieve more acceptable odor characteristics.
The "gas phase concentration" of odorant material is defined by measuring the level of odorant material in a head space over a 2,2,4-trimethyl-1,3-pentanediol sample containing odorant materials. Chromatograms are generated using a 105 mL head space sample over about 2 grams of sample. The head space sample is trapped onto a solid absorbent and thermally desorbed onto a column directly via cryofocusing at about -100°C. The identification of materials is based on the peaks in the chromatograms. The gas phase concentration of each odorant material found in a typical commercially available 2,2,4-trimethyl-1,3-pentanediol sample and a typical invention sample is as follows:
Approximate Concentration of Head Space Impurities Chemical Identification Gas chase concentration (~aIL1 Decreased by Commercial Typical Typical Typical Invention Sample invention Invention Invention Sample Sample Sample #1 #2 #3 Isobutyl aldehyde> 17 0.1 0.1 0.2 Isobutyric acid >8 0.1 <0.1 0.1 2,2,4-Trimethyl-3-keto-> 20 0.2 0.1 0.1 pentanol 2,2,4-Trimethyl-3-keto->2 < 0.1 < 0.1 ~ < 0.1 pentanol isobutyrate Diisopropyt ketone1 0.1 0.1 <0.1 2,2,4-Trimethyl-1,3- 1 <0.1 <0.1 <0.1 pentanediol monoisobutyrate Increased by Invention Isobutanol 3 > 17 > 19 > 26 Isobutyl isobutyrate 9 > 10 > 12 > 22 The acceptable gas phase concentrations of each odorant material are as follows:
isobutyl aldehyde should be less than about 1 ~, preferably less than about 10, more preferably less than about 5, and most preferably less than about 1 micrograms per liter pg/L); isobutyric acid should be less than about 7, preferably less than about 4, and more preferably less than about 1 micrograms per liter (~g/L); 2,2,4-trimethyl-3-keto-pentanol should be less than about 19, preferably less than about 10, and more preferably less than about 1 micrograms per liter (~g/L); 2,2,4-trimethyl-3-keto-pentanol isobutyrate should be less than about 2, preferably less than about 1.5, and more preferably less than about 1 micrograms per liter(~g/L); diisopropyl ketone should be less than about 3, preferably less than about 2, and more preferably less than about 1 micrograms per liter (pg/L);
2,2,4-trimethyl-1,3-pentanediol monoisobutyrate should be less than about 3, preferably less than about 2, and more preferably less than about 1 micrograms per liter (~g/L).
These gas phase concentration levels provide better odor than the commercially available 2,2,4-trimethyl-1,3-pentanediol.
Decreasing the gas phase concentration of the above odorant materials by some methods result in increasing the gas phase concentration of other materials, such as isobutanol and isobutyl isobutyrate. Isobutanol has been described as having a "[c]hoking, cough-provoking odor unless diluted; then rather mild, chemical, sweet, yet harsh." See Steffen Arctander, PERFUME AND FLAVOR CHEMICALS, Vol. I, No. 390 (1969). Isobutyl isobutyrate has an odor described as a "[s]weet-fruity, but also rather harsh-Pineapple-like, diffusive-ethereal odor. Fresher, but less characteristic (a non-descript fruit type) than the other isomers. Occasionally used in masking odors for industrial masking of repulsive odors, phenolic, cresylic, "chemical" odors, solvent odors, etch The relatively low boiling point (and high vapor pressure at room temperature) of this ester makes it particularly suitable for such purposes."
See Steffen Arctander, PERFUME AND FLAVOR CHEMICALS, Vol. I, No. 415 (1969).
It is especially novel and unobvious to process commercially available 2,2,4-trimethyl-1,3-pentanediol so that the gas phase concentrations of certain odorant materials, such as isobuty! aldehyde and isobutyric acid, are decreased while the gas phase concentrations of other materials, such as isobutanol and isobutyl isobutyrate, are increased, which surprisingly results in an overall improvement in the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. It is also novel and unobvious to process commercially available 2,2,4-trimethyl-1,3-pentanediol as described herein and use the 2,2,4-trimethyl-1,3-pentanediol having improved odor in consumer products, such as fabric softeners, to achieve a more acceptable product odor.
It is surprising that an increase in the gas phase concentration of isobutanol, along with a decrease in the gas phase concentration of odorant materials, particularly isobutyl aldehyde and isobutyric acid, will result in an overall improvement in the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. This is especially unexpected when one considers the typically offensive odor associated with isobutanol. It is theorized, although not wanting to be bound by theory, that the combined positive effect of reducing the gas phase concentrations of odorant materials like isobutyl aldehyde, isobutyric acid, and diisopropyl ketone, along with a masking effect of increasing the gas concentration of isobutyl isobutyrate, will outweigh any negative effect of increasing the gas phase concentration of isobutanol, which will result in commercially available 2,2,4-trimethyl-1,3-pentanediol having a much improved odor.
It is also theorized, although not wanting to be bound by theory, that it is important to incorporate the 2,2,4-trimethyl-1,3-pentanediol having improved odor into a fabric softening composition having a low pH. This is important because it is believed that the low pH of the fabric softening composition reduces the tendency of any esters, such as isobutyl isobutyrate, to hydrolyze over time to form isobutyric acid, which would negatively impact the odor of the composition.
II. Process for Imnrovin~ the Odor of Commercial 2.2.4-Trimethyl-1 3-Pentanediol Reduction is an effective process for improving the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. For maximum improvement in odor, reduction of 2,2,4-trimethyl-I,3-pentanediol can be accomplished by treating it with sodium borohydride as a reducing agent. Any of several forms of sodium borohydride may be used. For example, sodium borohydride powder, pellets, granules, or aqueous solution in combination with a base stabilizing agent, such as sodium hydroxide can be used. Potassium borohydride or other metal borohydrides can also be used. The amount of sodium borohydride used to reduce commercially available 2,2,4-trimethyl-1,3-pentanediol is 0.05% to 5%, preferably 0.2% to 2%, and more preferably 0.5% to i .5%, by weight of the 2,2,4-trimethyl-1,3-pentanediol.
Commercially available 2,2,4-trimethyl-1,3-pentanediol can also be reduced by catalytieally hydrogenating it to improve its odor. Hydrogenation of 2,2,4-trimethyl-1,3-pentanediol is preferably accomplished by using hydrogen and a hydrogenation catalyst, including, but not limited to, palladium, nickel, copper, platinum, and copper chromite catalysts, or combinations of such catalysts. This can be accomplished in either a batch or continuous hydrogenation process. The catalyst can be slurried or used in a fixed bed.
Other catalytic hydrogenation processes are described in Robert J. Peterson, HYDROGENATION CATALYSTS ( 1977), incorporated herein by reference.
Recrystallization of commercially available 2,2,4-trimethyl-1,3-pentanediol is another effective way to remove odorant materials. One preferred recrystallization process involves taking up the 2,2,4-trimethyl-1,3-pentanediol in hexane to form a solution, optionally treating the solution with activated carbon, crystallizing the 2,2,4-trimethyl-1,3-pentanediol from hexane, and then evaporating the hexane solvent.
Another, more preferred, recrystallization process includes taking up the 2,2,4-trimethyi-1,3-pentanediol in hexane to form a solution, treating the solution with an an ion exchange resin. crystallizing 2.2,4-trimethyl-1.3-pentanediol from hexane, extracting it with an aqueous solution, drying it over sodium sulfate, and then evaporating the hexane solvent. Other recrystallization processes are discussed in Robert H. Perry &
Cecil H.
Chilton, CHEMICAL ENGINEERS HANDBOOK 17-8 to 17-25 (5th ed. 1973), incorporated herein by reference.
The present invention also involves fractionally distilling commercially available 2,2,4-trimethyl-1,3-pentanediol in order to remove at least one odorant material. The fractional distillation can be carried out in either a batch or continuous feed mode. with the resulting 2,2,4-trimethyl-1,3-pentanediol taken off as either an overhead or side stream. A fractional distillation process typically results in a light fraction, a middle fraction, and a heavy fraction. wherein the middle fraction of 2,2,4-trimethyl-I ,3-pentanediol has improved odor. The odor of the fractionally distilled 2,2,4-trimethyl-1,3-pentanediol can then be further improved by reducing or hydrogenating the fractionally distilled 2,2,4-trimethyl-1,3-pentanediol by using the reducing or hydrogenating agents described herein. Fractional distillation processes are also described in Robert H. Perry & Cecil H. Chilton, CHEMICAL ENGINEERS HANDBOOK 13-I to 13-60 (5th ed. 1973), incorporated herein by reference.
A base treatment process can also improve the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. A base treatment process useful for the present invention involves adding a solution containing a base, such as sodium hydroxide, sodium carbonate. or sodium methoxide at 25%, and a solvent, such as methanol or water. to 2,2,4-trimethyl-1,3-pentanediol in order to form an alkaline liquid mixture. The alkaline mixture is then heated to reflux the solvent. An acid, such as hydrochloric acid, is added to the alkaline mixture to adjust the pH in order to create a neutral liquid mixture. The neutral liquid mixture is then fractionally distilled to form a light fraction, _7_ a middle fraction, and a heavy fraction. The resulting middle fraction and heavy fraction of 2,2,4-trimethyl-1,3-pentanediol have improved odor.
The odor of the 2,2,4-trimethyl-1,3-pentanediol processed according to any of the processes described above can be further improved by aqueous extraction(s), which can be carried out in either a batch or continuous operation. A counter-current column can be utilized for continuous aqueous extractions. Aqueous extraction(s) alone can improve the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol, but it is preferred to use aqueous extraction(s) in combination with one or more processes described herein.
Aqueous extration steps) can also incorporate a base, such as sodium hydroxide or sodium carbonate, to further improve the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol.
Vacuum stripping will also improve the odor of commercially available 2,2,4-trimethyl-1,3-pentanediol. It is preferred that vacuum stripping be used in combination with at least one or more of the processes described herein.
Another process involves nitrogen sparging of molten 2,2,4-trimethyl-1,3-pentanediol to decrease the gas phase concentration of odorant materials.
While this process by itself is not as effective as the previously described processes, nitrogen sparging can be useful as a final odor-improving step in combination with at least one or more of the previously mentioned processes. Nitrogen sparging can aid in the removal of solvent odor from a recrystallization process.
The present invention also encompasses improving the odor of commercially available 2,2,4-trimethyl-I ,3-pentanediol by a combination of the processes described herein. Preferred embodiments of the present invention are described in the Examples provided hereinafter.
It is preferred that the odorant materials found in commercially available 2,2,4-trimethyl-1,3-pentanediol not be reduced by alkoxyiation because the alkoxylated materials will change the nature of the 2,2,4-trimethyl-1,3-pentanediol. As described in PCT Application No. W09703169-AI, incorporated by reference hereinbefore, the alkoxylation changes the ClogP of the 2,2,4-trimethyl-1,3-pentanediol.
III. Fabric Softening Compositions A. Other Solvents The commercially available 2,2,4-trimethyl-1,3-pentanediol having improved odor of the present invention can be used as a principal solvent in liquid fabric softening compositions, as disclosed in PCT Application Nos. W09703169-AI and W09703170-A1, incorporated by reference hereinbefore. It can also be used in such compositions as part of a mixture of other suitable solvents to form a principal solvent system.

_g_ For the clear fabric softening compositions of the present invention, the principal solvent is typically less than about 40%, preferably from about 5% to about 35%, more preferably from about 10% to about 25%, and even more preferably from about 12% to about 18%, by weight of the composition. Said principal solvent is selected to minimize solvent odor impact in the composition and to provide a iow viscosity to the final composition. For example, isopropyl alcohol is not very effective and has a strong odor.
n-Propyl alcohol is more effective, but also has a distinct odor. Several butyl aicohols also have odors but can be used for effective clarity/stability, especially when used as part of a principal solvent system to minimize their odor. The alcohols are also selected for optimum low temperature stability, that is they are able to form compositions that are liquid with acceptable low viscosities and translucent, preferably clear, down to about 40°F (about 4.4°C) and are able to recover after storage down to about 20°F (about 6.7°C).
The suitability of any principal solvent for the formulation of the liquid, concentrated, preferably clear, fabric softener compositions herein with the requisite stability is surprisingly selective. Suitable solvents can be selected based upon their octanol/water partition coefficient (P). Octanol/water partition coefficient of a principal solvent is the ratio between its equilibrium concentration in octanol and in water. The partition coefficients of the principal solvent ingredients of this invention are conveniently given in the form of their logarithm to the base 10, loge.
The loge of many ingredients has been reported; for example, the Pomona92 database, available from Daylight Chemical Information Systems, Ine. (Daylight CIS), Irvine, California, contains many, along with citations to the original literature.
However, the iogP values are most conveniently calculated by the "CLOGP"
program, also available from Daylight CIS. This program also lists experimental loge values when they are available in the Pomona92 database. The "calculated loge"
(ClogP) is determined by the fragment approach of Hansch and Leo (cf., A. Leo, in Comprehensive Medicinal Chemistry, Vol. 4. C. Hansch, P. G. Sammens, J. B. Taylor and C. A.
Ramsden, 'ids., p. 295. Pergamon Press, 1990, incorporated herein by reference). The fragment approach is based on the chemical structure of each ingredient, and takes into account the numbers and types of atoms, the atom connectivity, and chemical bonding.
The CIogP values, which are the most reliable and widely used estimates for this physicochemical property, are preferably used instead of the experimental loge values in the selection of the principal solvent ingredients which are useful in the present invention. Other methods that can be used to compute ClogP include, e.g., Crippen's fragmentation method as disclosed in J. Chem. Inf. Comput. Sci., 27, 21 (1987);

Viswanadhan's fragmentation method as disclose in J. Chem. lnf. Comput. Sci., 29, 163 ( I 989); and Broto's method as disclosed in Eur. 3. Med. Chem. - Chim.
Theor., 19, 71 ( 1984).
The principal solvents herein are selected from those having a ClogP of from about 0.15 to about 0.64, preferably from about 0.25 to about 0.62, and more preferably from about 0.40 to about 0.60, said principal solvent preferably being asymmetric, and preferably having a melting, or solidification, point that allows it to be liquid at, or near room temperature. Solvents that have a low molecular weight and are biodegradable are also desirable for some purposes. The more asymmetric solvents appear to be very desirable, whereas the highly symmetrical solvents, having a center of symmetry, such as 1,7-heptanediol, or 1,4-bis(hydroxymethyl)cyclohexane, appear to be unable to provide the essentially clear compositions when used alone, even though their CIogP
values fall in the preferred range. One can select the most suitable principal solvent by determining whether a composition containing about 27% di(oleyoyloxyethyl)dimethylammonium chloride, about 16-20% of principal solvent, and about 4-6% ethanol remains clear during storage at about 40°F (about 4.4°C) and recovers from being frozen at about 0°F
(about -18°C).
When there is an insufficient amount of principal solvent e.g.: 2,2,4-trimethyl-1,3-pentanediol having improved odor of the present invention; the ethoxylate, diethoxylate, or triethoxylate derivatives of 2,2,4-trimethyl-I,3-pentanediol;
2-ethyl-1,3-hexanediol; and/or 2-ethyl-1,3-hexanediol ethoxylates (I-3) and/or mixtures thereof, to provide a clear product, or even to provide a stable product, other solvents can be added, preferably I,4-cyclohexanedimethanol.
The typical principal solvent, in addition to 2,2,4-trimethyl-1,3-pentanediol having improved odor of the present invention, is preferably selected from the group consisting of:
I. mono-ols including:
a. n-propanol; and/or b. ' 2-butanol and/or 2-methyl-2-propanol;
II. hexane diol isomers including: 2,3-butanediol, 2,3-dimethyl-; 1,2-butanediol, 2,3-dimethyl-; I,2-butanediol, 3,3-dimethyl-; 2,3-pentanediol, 2-methyl-; 2,3-pentanediol, 3-methyl-; 2,3-pentanediol, 4-methyl-; 2,3-hexanediol; 3,4-hexanediol; 1,2-butanediol, 2-ethyl-; 1,2-pentanediol, 2-methyl-; 1,2-pentanediol, 3-methyl-; 1,2-pentanedioh 4-methyl-; and/or 1,2-hexanediol;
III. heptane diol isomers including: 1,3-propanediol, 2-butyl-;,1,3-propanediol, 2,2-diethyl-; 1,3-propanediol, 2-(1-methylpropyl)-; 1,3-propanediol, 2-(2-methylpropyl)-;

1,3-propanedioh 2-methyl-2-propyl-; 1,2-butanediol, 2,3,3-trimethyl-; 1,4-butanediol, 2-ethyl-2-methyl-; 1,4-butanediol, 2-ethyl-3-methyl-; 1,4-butanediol, 2-propyl-;
1,4-butanediol, 2-isopropyl-; 1,5-pentanediol, 2,2-dimethyl-; 1,5-pentanedioh 2,3-dimethyl-;
1,5-pentanediol, 2,4-dimethyl-; I,5-pentanediol, 3,3-dimethyl-; 2,3-pentancdiol, 2,3-dimethyl-; 2,3-pentanediol, 2.4-dimethyl-; 2,3-pentanediol, 3,4-dimethyl-; 2,3-pentanediol, 4,4-dimethyl-; 3,4-pentanediol, 2,3-dimethyl-; I,S-pentanediol, 2-ethyl-;
1,6-hexanediol, 2-methyl-; 1,6-hexanediol, 3-methyl-; 2,3-hexanediol, 2-methyl-; 2,3-hexanediol, 3-methyl-; 2,3-hexanediol, 4-methyl-; 2,3-hexanediol, S-methyl-;
3,4-hexanediol, 2-methyl-; 3,4-hexanediol, 3-methyl-; 1,3-heptanediol; 1,4-heptanediol; 1,5-heptanediol; and/or 1,6-heptanediol;
IV. octane diol isomers including: 1,3-propanediol, 2-(2-methylbutyl)-; 1,3-propanediol, 2-(1,1-dimethylpropyl)- 1,3-propanediol, 2-(1,2-dimethylpropyl)-;
1,3-propanediol, 2-(1-ethylpropyl)-; 1,3-propanediol, 2-(1-methylbutyl)-; 1,3-propanediol, 2-(2,2-dimethylpropyl)-; 1,3-propanediol. 2-(3-methylbutyl)-; 1,3-propanediol, 2-butyl-2-methyl-; 1,3-propanediol, 2-ethyl-2-isopropyl-; 1.3-propanediol, 2-ethyl-2-propyl-; 1,3-propanediol, 2-methyl-2-(I-methylpropyl)-; 1,3-propanediol, 2-methyl-2-(2-methylpropyl)-; 1,3-propanediol, 2-tertiary-butyl-2-methyl-; 1,3-butanediol, 2,2-diethyl-;
1,3-butanediol, 2-(I-methyipropyl)-; 1,3-butanediol, 2-butyl-; 1,3-butanediol, 2-ethyl-2,3-dimethyl-; 1,3-butanediol, 2-( I , I -dimethylethyl)-; 1,3-butanediol, 2-(2-methylpropyl)-; 1,3-butanediol, ?-methyl-2-isopropyl-; 1,3-butanediol, 2-methyl-2-propyl-; 1,3-butanediol, 3-methyl-2-isopropyl-; 1,3-butanediol, 3-methyl-2-propyl-; 1,4-butanediol. 2,2-diethyl-; 1,4-butanediol, 2-methyl-2-propyl-; 1,4-butanediol, 2-(1-methylpropyl)-; I ,4-butanediol, 2-ethyl-2,3-dimethyl-; I ,4-butanediol, 2-ethyl-3,3-dimethyl-; I ,4-butanediol, 2-( I ,1-dimethylethyl)-; 1,4-butanediol, 2-(2-methylpropyl)-;
1,4-butanediol, 2-methyl-3-propyl-; 1,4-butanediol, 3-methyl-2-isopropyl-; I,3-pentanediol, 2,2,3-trimethyl-; 1,3-pentanediol, 2,2,4-trimethyl-; 1,3-pentanediol, 2,3,4-trimethyl-; 1,3-pentanediol, 2,4,4-trimethyl-; 1,3-pentanediol, 3,4,4-trimethyl-; 1,4-pentanediol, 2,2,3-trimethyl-; 1,4-pentanediol, 2,2,4-trimethyl-; 1,4-pentanediol, 2,3,3-trimethyl-; 1,4-pentanediol, 2,3,4-trimethyl-; 1,4-pentanediol, 3,3,4-trimethyl-; 1,5-pentanediol, 2,2,3-trimethyl-; I ,S-pentanediol, 2,2,4-trimethyl-; 1,5-pentanediol, 2,3,3-trimethyl-; I,5-pentanediol, 2,3,4-trimethyl-; 2,4-pentanediol, 2,3,3-trimethyl-; 2,4-pentanediol, 2,3,4-trimethyl-; 1,3-pentanediol, 2-ethyl- 2-methyl-; 1,3-pentanediol, 2-ethyl-3-methyl-; 1,3-pentanediol, 2-ethyl-4-methyl-; 1,3-pentanediol, 3-ethyl-2-methyl-;
1,4-pentanediol, 2-ethyl-2-methyl-; 1,4-pentanediol, 2-ethyl-3-methyl-; 1,4-pentanediol, 2-ethyl-4-methyl-; 1,4-pentanediol, 3-ethyl-2-methyl-; 1,4-pentanediol, 3-ethyl-3-methyl-; I,5-pentanediol, 2-ethyl-2-methyl-; 1,5-pentanediol, 2-ethyl-3-methyl-; I,5-pentanediol, 2-ethyl-4-methyl-; 1,5-pentanediol, 3-ethyl-3-methyl-; 2,4-pentanediol, 3-ethyl-2-methyl-; 1,3-pentanediol, 2-isopropyl-; 1,3-pentanediol, 2-propyl-;
1,4-pentanediol, 2-isopropyl-; 1,4-pentanediol, 2-propyl-; 1,4-pentanediol, 3-isopropyl-; 1,5-pentanediol, 2-isopropyl-; 2,4-pentanediol, 3-propyl-; I,3-hexanediol, 2,2-dimethyl-; 1,3-hexanediol, 2,3-dimethyl-; 1,3-hexanediol, 2,4-dimethyl-; 1,3-hexanediol, 2,5-dimethyl-;
I ,3-hexanediol, 3,4-dimethyl-; 1,3-hexanediol, 3,5-dimethyl-; 1,3-hexanediol, 4,5-dimethyl-; I,4-hexanediol, 2,2-dimethyl-; 1,4-hexanediol, 2,3-dimethyl-; 1,4-hexanediol, 2,4-dimethyl-; 1,4-hexanediol, 2,5-dimethyl-; 1,4-hexanediol, 3,3-dimethyl-;
1,4-hexanediol, 3,4-dimethyl-; 1,4-hexanediol, 3,5-dimethyl-; 1,3-hexanediol, 4,4-dimethyl-;
1,4-hexanediol, 4,5-dimethyl-; 1,4-hexanediol, 5,5-dimethyl-; 1,5-hexanediol, 2,2-dimethyl-; 1,5-hexanediol, 2,3-dimethyl-; 1,5-hexanediol, 2,4-dimethyl-; 1,5-hexanediol, 2.5-dimethyl-; 1,5-hexanediol, 3,3-dimethyl-; 1,5-hexanediol, 3,4-dimethyl-;
1,5-hexanediol, 3,5-dimethyl-; I,5-hexanediol, 4,5-dimethyl-; 1,6-hexanediol, 2,2-dimethyl-;
1,6-hexanediol, 2,3-dimethyl-; 1,6-hexanediol, 2,4-dimethyl-; 1,6-hexanediol, 2,5-dimethyl-; 1,6-hexanediol, 3,3-dimethyl-; 1,6-hexanediol, 3,4-dimethyI-; 2,4-hexanediol, 2,3-dimethyl-; 2,4-hexanediol, 2,4-dimethyl-; 2,4-hexanediol, 2,5-dimethyl-;
2,4-hexanediol, 3,3-dimethyl-; 2,4-hexanediol, 3,4-dimethyl-; 2,4-hexanediol, 3,5-dimethyl-;
2,4-hexanediol, 4,5-dimethyl-; 2,4-hexanediol, 5,5-dimethyl-; 2,5-hexanediol, 2,3-dimethyl-; 2,5-hexanediol, 2,4-dimethyl-; 2,5-hexanediol, 2,5-dimethyl-; 2,5-hexanediol, 3,3-dimethyl-; 2,5-hexanediol, 3,4-dimethyl-; 2,6-hexanediol, 3,3-dimethyl-;
1,3-hexanediol, 2-ethyl-; 1,3-hexanediol, 4-ethyl-; 1,4-hexanediol, 2-ethyl-; 1,4-hexanediol, 4-ethyl-; 1,5-hexanediol, 2-ethyl-; 2,4-hexanediol, 3-ethyl-; 2,4-hexanediol, 4-ethyl-; 2,5-hexanediol, 3-ethyl-; 1,3-heptanediol, 2-methyl-; 1,3-heptanediol, 3-methyl-;
1,3-heptanediol, 4-methyl-; 1,3-heptanediol, 5-methyl-; 1,3-heptanediol, 6-methyl-; 1,4-heptanediol, 2-methyl-; 1,4-heptanediol, 3-methyl-; 1,4-heptanediol, 4-methyl-; 1,4-heptanediol, 5-methyl-; 1,4-heptanediol, 6-methyl-; 1,5-heptanediol, 2-methyl-; 1,5-heptanediol, 3-methyl-; 1,5-heptanediol, 4-methyl-; I,5-heptanediol, 5-methyl-; 1,5-heptanediol, 6-methyl-; 1,6-heptanediol, 2-methyl-; 1,6-heptanediol, 3-methyl-; I,6-heptanediol, 4-methyl-; 1,6-heptanediol, 5-methyl-; 1,6-heptanediol, 6-methyl-; 2,4-heptanediol, 2-methyl-; 2,4-heptanediol, 3-methyl-; 2,4-heptanediol, 4-methyl-; 2,4-heptanediol, 5-methyl-; 2,4-heptanediol, 6-methyl-; 2,5-heptanediol, 2-methyl-; 2,5-heptanediol, 3-methyl-; 2,5-heptanediol, 4-methyl-; 2,5-heptanediol, 5-methyl-; 2,5-heptanediol, 6-methyl-; 2,6-heptanedioi, 2-methyl-; 2,6-heptanediol, 3-methyl-; 2,6-heptanediol, 4-methyl-; 3,4-heptanediol, 3-methyl-; 3,5-heptanediol, 2-methyl-; 3,5-heptanediol, 3-methyl-; 3,5-heptanediol, 4-methyl-; 2,4-octanedioh 2,5-octanediol; 2,6-octanediol; 2,7-octanediol; 3,5-octanediol; and/or 3,6-octanediol;

V. nonane diol isomers including: 2,4-pentanediol, 2,3,3,4-tetramethyl-; 2,4-pentanediol, 3-tertiarybutyl-; 2,4-hexanediol, 2,5,5-trimethyl-; 2,4-hexanediol, 3,3,4-trimethyl-; 2,4-hexanediol, 3.3,5-trimethyl-; 2,4-hexanediol, 3,5,5-trimethyl-; 2,4-hexanediol, 4,5,5-trimethyi-; 2,5-hexanediol, 3,3,4-trimethyl-; and/or 2,5-hexanediol, 3,3,5-trimethyl-;
VI. glyceryl ethers and/or di(hydroxyalkyl)ethers including: 1,2-propanediol, 3-(n-pentyloxy)-; 1,2-propanediol, 3-(2-pentyloxy)-; 1,2-propanediol, 3-(3-pentyloxy)-; 1,2-propanediol, 3-(2-methyl-1-butyloxy)-; 1,2-propanediol, 3-(iso-amyloxy)-; 1,2-propanediol, 3-(3-methyl-2-butyloxy)-; 1,2-propanediol, 3-(cyclohexyloxy)-;
1,2-propanediol, 3-(I-cyclohex-I-enyloxy)-; 1,3-propanediol, 2-(pentyloxy)-; 1,3-propanediol, 2-{2-pentyloxy)-; 1,3-propanediol, 2-(3-pentyloxy)-; 1,3-propanediol, 2-(2-methyl-I-butyloxy)-; I_3-propanediol. 2-(iso-amyloxy)-; 1,3-propanediol, 2-(3-methyl-2-butyloxyj-; 1,3-propanediol, 2-(cyclohexyloxy)-; 1,3-propanediol, 2-(1-cyclohex-1-enyloxy)-; 1,2-propanediol, 3-(butyloxy)-, triethoxylated; 1,2-propanediol, 3-(butyloxy)-, tetraethoxylated; 1,2-propanediol, 3-(butyloxy)-, pentaethoxylated; 1,2-propanediol, 3-(butyloxy)-, hexaethoxylated: 1,2-propanediol. 3-{butyloxy)-, heptaethoxylated; 1,2-propanediol, 3-(butyloxy)-, octaethoxylated; 1,2-propanediol, 3-{butyloxy)-, nonaethoxylated; 1,2-propanediol, 3-(butyloxy)-, monopropoxylated; 1,2-propanediol, 3-(butyloxy)-, dibutyleneoxylated; 1,2-propanediol, 3-(butyloxy)-, tributyleneoxylated;
1,2-propanediol, 3-phenyloxy-; 1,2-propanediol, 3-benzyloxy-; I ,2-propanediol, 3-(2-phenylethyloxy)-; 1,2-propanediol, 3-(I-phenyl-2-propanyloxy)-; 1,3-propanediol, 2-phenyloxy-; 1,3-propanediol. 2-(m-cresyloxy)-; 1,3-propanediol, 2-{p-cresyloxy)-; 1.3-propanediol, -benzyloxy-; 1,3-propanediol, 2-(2-phenylethyloxy}-; 1,3-propanediol, 2-(1-phenylethyloxy)-; bis(2-hydroxybutyl)ether; and/or bis(2-hydroxycyclopentyl)ether:
VII. saturated and unsaturated alicyclic diols and their derivatives including:
(a) the saturated diols and their derivatives, including:
1-isopropyl-1,2-cyclobutanediol; 3-ethyl-4-methyl-1,2-cyclobutanediol; 3-propyl-1.2-cyclobutanediol; 3-isopropyl-1,2-cyclobutanediol; 1-ethyl-1,2-cyclopentanediol; 1,2-dimethyl-lt2-cyclopentanediol; 1,4-dimethyl-1,2-cyclopentanediol; 2,4,5-trimethyl-1,3-cyciopentanediol; 3,3-dimethyl-1,2-cyclopentanediol; 3,4-dimethyl-1,2-cyclopentanediol; 3,5-dimethyl-1.2-cyclopentanediol; 3-ethyl-1,2-cyclopentanediol; 4,4-dimethyl-1,2-cyclopentanediol; 4-ethyl- I ,2-cyciopentanediol; I , I -bis(hydroxymethyl)cyclohexane; 1,2-bis(hydroxymethyl)cyclohexane; 1,2-dimethyl-1,3-cyclohexanediol; 1,3-bis(hydroxymethyl)cyclohexane; 1,3-dimethyl-1,3-cyclohexanediol; 1,6-dimethyl-1,3-cyclohexanediol; 1-hydroxy-cyclohexaneethanol; I-hydroxy-cyclohexanemethanol; I-ethyl-1,3-cyclohexanediol; 1-methyl-1,2-cyclohexanediol; 2,2-dimethyl-1,3-cyclohexanediol; 2,3-dimethyl-1,4-cyclohexanediol;
2,4-dimethyl-1,3-cyclohexanediol; 2,5-dimethyl-1,3-cyclohexanediol; 2,6-dimethyi-1,4-cyclohexanediol; 2-ethyl-1,3-cyclohexanediol; 2-hydroxycyclohexaneethanol; 2-hydroxyethyl-1-cyclohexanol; 2-hydroxymethylcyclohexanol; 3-hydroxyethyl-1-cyclohexanol; 3-hydroxycyclohexaneethanol; 3-hydroxymethylcyclohexanol; 3-methyl-1,2-cyclohexanediol; 4,4-dimethyl-1,3-cyclohexanediol; 4,5-dimethyl-1,3-cyclohexanediol; 4,6-dimethyl-1,3-cyclohexanediol; 4-ethyl-1,3-cyclohexanediol; 4-hydroxyethyl-I-cyclohexanol; 4-hydroxymethylcyclohexanol; 4-methyl-1,2-cyclohexanediol; 5,5-dimethyl-I,3-cyclohexanediol; 5-ethyl-I,3-cyclohexanediol; 1,2-cycloheptanediol; 2-methyl-1,3-cycloheptanediol; 2-methyl-1,4-cycloheptanediol; 4-methyl-1,3-cycloheptanediol; 5-methyl-1,3-cycloheptanediol; 5-methyl-1,4-cycloheptanediol; 6-methyl-1,4-cycloheptanediol; ; 1,3-cyclooctanediol; 1,4-cyclooctanediol; I,5-cyclooctanediol; 1,2-cyclohexanediol, diethoxylate; 1,2-cyclohexanediol, triethoxylate; I,2-cyclohexanediol, tetraethoxylate; 1,2-cyclohexanediol, pentaethoxylate; 1,2-cyclohexanediol, hexaethoxylate; 1,2-cyclohexanediol, heptaethoxylate; 1,2-cyclohexanediol, octaethoxylate; 1,2-cyclohexanediol, nonaethoxylate; 1,2-cyclohexanediol, monopropoxylate; 1,2-cyclohexanediol, monobutylenoxylate; 1,2-cyclohexanediol, dibutylenoxylate;
and/or I,2-cyclohexanediol, tributylenoxylate; and (b). the unsaturated alicyclic diols including: 1,2-cyclobutanediol, 1-ethenyl-2-ethyl-; 3-cyclobutene-1,2-diol, 1,2,3,4-tetramethyl-; 3-cyclobutene-1,2-diol, 3,4-diethyl-; 3-cyclobutene-1,2-diol, 3-(1,1-dimethylethyl)-; 3-cyclobutene-1,2-diol, 3-butyl-; 1,2-cyclopentanediol, 1,2-dimethyl-4-methylene-; 1,2-cyclopentanediol, 1-ethyl-3-methylene-; 1,2-cyclopentanediol, 4-{1-propenyl); 3-cyclopentene-1,2-diol, 1-ethyl-3-methyl-; 1,2-cyclohexanediol, 1-ethenyl-; 1,2-cyclohexanediol, 1-methyl-3-methylene-;
1,2-cyclohexanediol, 1-methyl-4-methylene-; 1,2-cyclohexanediol, 3-ethenyl-;
1,2-cyclohexanediol, 4-ethenyl-; 3-cyclohexene-1,2-diol, 2,6-dimethyl-; 3-cyclohexene-1,2-diol, 6,6-dimethyl-; 4-cyciohexene-1,2-diol, 3,6-dimethyl-; 4-cyclohexene-1,2-diol, 4,5-dimethyl-; 3-cyclooctene-1,2-diol; 4-cyclooctene-1,2-diol; and/or 5-cyclooctene-1,2-diol;
VIII. Alkoxylated derivatives of C3_g diols [In the following disclosure, "EO"
means polyethoxylates, i.e., -(CH2CH20)nH; Me-En means methyl-capped polyethoxylates -(CH2CH20)nCH3 ; "2(Me-En)" means 2 Me-En groups needed; "PO" means polypropoxylates, -(CH(CH3)CH20)nH ; "BO" means polybutyleneoxy groups, (CH(CH2CH3)CH20)nH ; and "n-BO" means poly(n-butyleneoxy) or poly(tetramethylene)oxy groups -(CH2CH2CH2CH20)nH. The use of the term "(Cx)"

herein refers to the number of carbon atoms in the base material which is alkoxylated.J
including:
I. 1,2-propanediol 2(Me-EI_4); 1,2-propanediol P04; 1,2-propanediol, 2-methyl- (Me-E4_Ip): 1,2-propanediol, 2-methyl- 2(Me-EI); 1,2-propanediol. 2-methyl-P03; 1,2-propanediol, 2-methyl- BOI; 1,3-propanediol 2(Me-E6_g); 1,3-propanediol POS_6; 1,3-propanediol, 2,2-diethyl- EI_~; 1,3-propanediol, 2,2-diethyl- POI;
1,3-propanediol, 2,2-diethyl- n-BO I _2; 1,3-propanediol, 2,2-dimethyl- 2(Me E I
_2); 1,3-propanediol, 2,2-dimethyl- P03_4; 1,3-propanediol, 2-(I-methylpropyl)- E1_~;
1,3-propanediol, 2-( I-methylpropyl)- POI ; 1,3-propanediol, 2-( 1-methylpropyl)-n-BOI _2;
1,3-propanediol, 2-{2-methylpropyl)- E I _~; I ,3-propanediol, 2-(2-methylpropyl)- POI ;
1,3-propanediol, 2-(2-methylpropyl)- n-BOI_~; 1,3-propanediol, 2-ethyl- (Me E6_10) 1,3-propanediol, 2-ethyl- 2(Me E I ); 1,3-propanediol, 2-ethyl- P03; 1,3-propanediol, 2-ethyl-2-methyl- (Me E I _6); 1,3-propanediol, 2-ethyl-2-methyl- P02; I ,3-propanediol, 2-ethyl-2-methyl- BOI ; 1,3-propanediol, 2-isopropyl- (Me E1 _6); 1,3-propanediol, 2-isopropyl- P02; 1,3-propanediol, 2-isopropyl- BO I ; I ,3-propanediol, 2-methyl- 2(Me E2_5); 1,3-propanediol, 2-methyl- P04_5; 1,3-propanediol, 2-methyl- B02; 1,3-propanediol, 2-methyl-2-isopropyl- E2-9; 1,3-propanediol, 2-methyl-2-isopropyl-POI;
1,3-propanediol, 2-methyl-2-isopropyl- n-BOI_3; 1,3-propanediol, 2-methyl-2-propyl-EI _7; I ,3-propanediol, 2-methyl-2-propyl- POI ; I ,3-propanediol, 2-methyl-2-propyl- n-BOI _2; 1,3-propanediol, 2-propyl- (Me E I _4); 1,3-propanediol, 2-propyl-P02; I ,3-propanediol, 2-propyl- BOI;
2. 1.2-butanediol (Me E2_g); 1.2-butanediol P02-3; 1.2-butanediol BOI;
1,2-butanediol, 2,3-dimethyl- E 1 _H; I .2-butanediol. 2.3-dimethyl- n-BOI _2;
I ,2-butanediol, 2-ethyl- E I _3; 1,2-butanediol, 2-ethyl- n-BO I ; 1,2-butanediol, 2-methyl- (Me E I _2); 1,2-butanediol, 2-methyl- PO I ; I ,2-butanediol, 3,3-dimethyl- E I
_6; 1,2-butanediol, 3,3-dimethyl- n-BOI_2; 1,2-butanediol, 3-methyl- (Me EI_2); 1,2-butanediol, 3-methyl- POI; 1,3-butanediol 2(Me E3_6); 1,3-butanediol POS; 1,3-butanediol B02;
1,3-butanediol, 2,2,3-trimethyl- (Me EI_3); 1,3-butanediol, 2,2,3-trimethyl-POI_2; 1,3-butanedioI;~2,2-dimethyl- (Me E3_g); 1,3-butanediol, 2,2-dimethyl- P03; 1,3-butanediol, 2,3-dimethyl- (Me E3_g); 1,3-butanediol, 2,3-dimethyl- P03; 1,3-butanediol, 2-ethyl-(Me EI_6); 1.3-butanediol, 2-ethyl- P02_3; 1,3-butanediol, 2-ethyl- BOI; 1,3-butanediol, 2-ethyl-2-methyl- (Me EI); 1,3-butanediol, 2-ethyl-2-methyl- POI; 1,3-butanediol, 2-ethyl-2-methyl- n-B02_4; 1,3-butanediol, 2-ethyl-3-methyl- (Me EI); 1,3-butanediol, 2-ethyl-3-methyl- POI ; 1,3-butanediol, 2-ethyl-3-methyl- n-B02_4; 1,3-butanediol, 2-isopropyl- (Me E I ); I ,3-butanediol, 2-isopropyl- PO I ; I ,3-butan~diol, 2-isopropyl- n-B02_4; 1,3-butanediol, 2-methyl- 2(Me El_3); 1,3-butanediol, 2-methyl- P04;
I,3-butanediol, 2-propyl- E2_9; 1,3-butanediol, 2-propyl- POI; 1,3-butanediol, 2-propyl- n-BOI_3; 1,3-butanediol, 3-methyl- 2(Me EI_3); 1,3-butanediol, 3-methyl- P04;
1,4-butanediol 2(Me E2_4); I ,4-butanediol P04_5; I ,4-butanediol B02; 1,4-butanediol, 2,2,3-trimethyl- E2_9; 1,4-butanediol, 2,2,3-trimethyl- POI; 1,4-butanediol, 2,2,3-trimethyl- n-BOI_3; 1,4-butanediol, 2,2-dimethyl- (Me EI_6); 1,4-butanediol, 2,2-dimethyl- P02; I ,4-butanediol, 2,2-dimethyl- BO I ; 1,4-butanediol, 2,3-dimethyl- (Me E I _6); 1,4-butanediol, 2,3-dimethyl- P02; I ,4-butanediol, 2,3-dimethyl- BO
I ; 1,4-butanediol, 2-ethyl- (Me EI_4); 1,4-butanediol, 2-ethyl- P02; 1,4-butanediol, 2-ethyl-BO I ; I ,4-butanediol, 2-ethyl-2-methyl- E I _~; 1,4-butanediol, 2-ethyl-2-methyl- PO I ;
1,4-butanediol, 2-ethyl-2-methyl- n-BO I _2; I,4-butanediol, 2-ethyl-3-methyl-E I _~; 1,4-butanediol, 2-ethyl-3-methyl- PO I ; I ,4-butanediol, 2-ethyl-3-methyl- n-BO I
_2; 1,4-butanediol, 2-isopropyl- E I _~; I ,4-butanediol, 2-isopropyl- PO I ; I ,4-butanediol, 2-isopropyl- n-BOI_2; 1,4-butanediol, 2-methyl- (Me E6_10); 1,4-butanediol, 2-methyl-2(Me E I ); I ,4-butanediol, 2-methyl- P03; 1,4-butanediol, 2-methyl- BOI ;
1,4-butanediol, 2-propyl- E I _5; I ,4-butanediol, 2-propyl- n-BO I _2; 1,4-butanediol, 3-ethyl-1-methyl- E2_9; 1,4-butanediol, 3-ethyl-1-methyl- POI; 1,4-butanediol, 3-ethyl-I-methyI- n-BOI_3; 2,3-butanediol (Me E6_IO); 2,3-butanediol 2(Me EI); 2,3-butanediol P03_4; 2,3-butanediol BOI; 2,3-butanediol, 2,3-dimethyl- E3_9; 2,3-butanediol, 2,3-dimethyl- POI; 2,3-butanediol, 2,3-dimethyl- n-BOI_3; 2,3-butanediol, 2-methyl-(Me EI_5); 2,3-butanediol, 2-methyl- P02; 2,3-butanediol, 2-methyl- BOI;
3. 1,2-pentanediol E3_I0; 1,2-pentanediol, POI; 1,2-pentanediol, n-B02_3;
1,2-pentanediol, 2-methyl E I _3; 1,2-pentanediol, 2-methyl n-BO I ; I ,2-pentanediol, 2-methyl BOI; 1,2-pentanediol, 3-methyl EI_3; 1,2-pentanediol, 3-methyl n-BOI;
1,2-pentanediol, 4-methyl E I _3; 1,2-pentanediol, 4-methyl n-BO I ; 1,3-pentanediol 2(Me-E I _ 2); 1,3-pentanediol P03_4; 1,3-pentanediol, 2,2-dimethyl- (Me-EI); 1,3-pentanediol, 2,2-dimethyl- POI; 1,3-pentanediol, 2,2-dimethyl- n-B02_4; 1,3-pentanediol, 2,3-dimethyl-(Me-EI); 1,3-pentanediol, 2,3-dimethyl- POI; 1,3-pentanediol, 2,3-dimethyl- n-B02_4;
I ,3-pentanediol, 2,4-dimethyl- (Me-E I ); I ,3-pentanediol, 2,4-dimethyl- PO
I ; 1,3-pentanediol', 2,4-dimethyl- n-B02_4; 1,3-pentanediol, 2-ethyl- E2_9; 1,3-pentanediol, 2-ethyl- POI; 1,3-pentanediol, 2-ethyl- n-BOI_3; 1,3-pentanediol, 2-methyl- 2(Me-EI-6);
1,3-pentanediol, 2-methyl- P02_3; 1,3-pentanediol, 2-methyl- BOI; 1,3-pentanediol, 3,4-dimethyl- (Me-EI); 1,3-pentanediol, 3,4-dimethyl- POI; 1,3-pentanediol, 3,4-dimethyl-n-B02_4; 1,3-pentanediol, 3-methyl- {Me-EI_6); 1,3-pentanediol, 3-methyl-P02_3; 1,3-pentanediol, 3-methyl- BOI; 1,3-pentanedioI, 4,4-dimethyl- (Me-EI); 1,3-pentanediol, 4,4-dimethyl- POI; 1,3-pentanediol, 4,4-dimethyl- n-B02_4; 1,3-pentanediol, 4-methyl-(Me-EI_6); 1,3-pentanediol, 4-methyl- P02_3; 1,3-pentanediol, 4-methyl- BOI;
1,4-pentanediol, 2(Me-E1_2); 1,4-pentanediol P03_4; 1,4-pentanediol, 2,2-dimethyl-(Me-EI); 1,4-pentanediol, 2,2-dimethyl- POI; 1,4-pentanediol, 2,2-dimethyl- n-B02_4; 1,4-pentanediol, 2,3-dimethyl- (Me-E I ); 1,4-pentanediol, 2,3-dimethyl- PO I ; I
,4-pentanediol, 2,3-dimethyl- n-B02_4; 1,4-pentanediol, 2,4-dimethyl- (Me-EI);
1,4-pentanediol, 2,4-dimethyl- POI; 1,4-pentanediol, 2,4-dimethyl- n-B02_4; 1,4-pentanediol, 2-methyl- (Me-E I _6); I ,4-pentanediol, 2-methyl- P02_3; 1,4-pentanediol, 2-methyl- BOI; 1,4-pentanediol, 3,3-dimethyl- (Me-EI); 1,4-pentanediol, 3,3-dimethyl-POI; 1,4-pentanediol, 3,3-dimethyl- n-B02-4; 1,4-pentanedioi, 3,4-dimethyl-(Me-EI);
1,4-pentanediol, 3,4-dimethyl- POI; 1,4-pentanediol, 3,4-dimethyl- n-B02_4;
1,4-pentanediol, 3-methyl- 2(Me-EI_6); 1,4-pentanediol, 3-methyl- P02_3; 1,4-pentanediol, 3-methyl- BOI; 1,4-pentanediol, 4-methyl- 2(Me-EI_6); 1,4-pentanediol, 4-methyl-PO~_3; 1,4-pentanediol, 4-methyl- BOI; 1,5-pentanediol, (Me-E4_10); 1,5-pentanediol 2(Me-EI); 1,5-pentanediol P03; 1,5-pentanediol, 2,2-dimethyl- EI_~; 1,5-pentanediol, 2,2-dimethyl- POI ; 1,5-pentanediol, 2 2-dimethyl- n-BOI _2; 1,5-pentanediol, 2,3-dimethyl- EI_~; 1,5-pentanediol, 2,3-dimethyl- POI; 1,5-pentanediol, 2,3-dimethyl- n-BOI_2; 1,5-pentanediol, 2,4-dimethyl- EI_~; 1,5-pentanediol, 2,4-dimethyl-POI; 1,5-pentanediol, 2,4-dimethyl- n-BOI_2; 1,5-pentanediol, 2-ethyl- El_5; 1,5-pentanediol, 2-ethyl- n-BOI_2; 1,5-pentanediol, 2-methyl- (Me-EI_4); 1,5-pentanediol, 2-methyl- P02;
1,5-pentanediol, 3,3-dimethyl- E I _~; 1,5-pentanediol, 3,3-dimethyl- PO I ;
1,5-pentanediol, 3,3-dimethyl- n-BO I _2; I ,5-pentanediol, 3-methyl- (Me-E I _4);
1,5-pentanediol, 3-methyl- PO~; ~,3-pentanediol, (Me-E I _3); 2,3-pentanediol, P02; 2,3-pentanediol. 2-methyl- E I _~; 2,3-pentanediol, 2-methyl- PO I ; 2,3-pentanediol, 2-methyl-n-BOI_2; ~,3-pentanediol. 3-methyl- EI_~; 2,3-pentanediol, 3-methyl- POI; 2,3-pentanediol, 3-methyl- n-BOI_2; '',3-pentanediol, 4-methyl- EI_~; 2,3-pentanediol, 4-methyl- POI; 2,3-pentanediol, 4-methyl- n-BOI_2; 2,4-pentanediol, 2(Me-EI-4);
2,4-pentanediol P04; 2,4-pentanediol. 2,3-dimethyl- (Me-EI_4); 2,4-pentanediol, 2,3-dimethyl- P02; 2,4-pentanediol, 2,4-dimethyl- (Me-EI-4); 2,4-pentanediol, 2,4-dimethyl- P02; 2,4-pentanediol, 2-methyl- (Me-E5_10); 2,4-pentanediol, 2-methyl- P03;
2,4-pentanediol, 3,3-dimethyl- (Me-EI_4); 2,4-pentanediol, 3,3-dimethyl- P02;
2,4-pentanediol, 3-methyl- (Me-E5_Ip); 2,4-pentanediol, 3-methyl- P03;
4. 1,3-hexanedioi (Me-EI_5); 1,3-hexanediol P02; 1,3-hexanediol BOI; 1,3-hexanediol, 2-methyl- E2_9; 1,3-hexanediol, 2-methyl- POI; 1,3-hexanediol, 2-methyl-n-BO I _3; 1,3-hexanediol, 2-methyl- BO I ; 1,3-hexanediol, 3-methyl- E2_9;
1,3-hexanediol, 3-methyl- POI; 1,3-hexanediol, 3-methyl- n-BOI_3; 1,3-hexanediol, methyl- E2_9; 1,3- .hexanediol, 4-methyl- POI; 1,3-hexanediol, 4-methyl- n-BOI_3; 1,3-hexanediol. 5-methyl- E2_9; 1,3-hexanediol, 5-methyl- POI; 1,3-hexanediol, 5-methyl-_17_ n-BO1_3; 1,4-hexanediol (Me-EI_5); 1,4-hexanediol P02; 1,4-hexanediol BOI; 1,4-hexanediol, 2-methyl- E2_9; 1,4-hexanediol, 2-methyl- POI; 1,4-hexanediol, 2-methyl-n-BO 1 _3; 1,4-hexanediol, 3-methyl- E2_9; 1,4-hexanediol, 3-methyl- PO ~ ;
1,4-hexanediol, 3-methyl- n-BO1_3; 1,4-hexanediol, 4-methyl- E2_g; 1,4-hexanediol, methyl- POI ; 1,4-hexanedioi, 4-methyl- n-BOI _3; 1,4-hexanediol, 5-methyl-E2_9; 1,4-hexanediol, 5-methyl- POI; 1,4-hexanediol, 5-methyl- n-BOI_3; 1,5-hexanediol (Me-E1_ 5); 1,5-hexanediol P02; 1,5-hexanediol BOI; 1,5-hexanediol, 2-methyl- E2_9;
1,5-hexanediol, 2-methyl- POI; 1,5-hexanediol, 2-methyl- n-BOl_3; 1,5-hexanediol, methyl- E2_9; 1,5-hexanediol, 3-methyl- POI; 1,5-hexanediol, 3-methyl- n-BO1_3; 1,5-hexanediol, 4-methyl- E2_9; 1,5-hexanediol, 4-methyl- POI; 1,5-hexanediol, 4-methyl-n-BO 1 _3; I ,5-hexanediol, 5-methyl- E2_9; 1,5-hexanediol, 5-methyl- PO I ;
1,5-hexanediol, 5-methyl- n-BO I _~; I ,6-hexanediol (Me-E I _2); I ,6-hexanediol POI _2; 1,6-hexanediol n-B04; 1,6-hexanediol, 2-methyl- EI_5; 1,6-hexanediol, 2-methyl- n-BOI_2;
1,6-hexanediol, 3-methyl- E I _5; I ,6-hexanedioi, 3-methyl- n-BO 1 _2; 2,3-hexanediol E I _ 5; 2,3-hexanediol n-BOI; 2,3-hexanediol BOI; 2,4-hexanediol (Me-E3_g); 2,4-hexanediol P03; 2,4-hexanediol, 2-methyl- (Me-E I _2); 2,4-hexanediol 2-methyl-POI _2;
2,4-hexanediol, 3-methyl- (Me-E I _2); 2,4-hexanediol 3-methyl- PO I _2; 2,4-hexanediol, 4-methyl- (Me-E I _2); 2,4-hexanediol 4-methyl- POI _2; 2,4-hexanediol, 5-methyl- (Me-EI _2}; 2,4-hexanediol 5-methyl- POI _2; 2,5-hexanediol (Me-E3_g); 2,5-hexanediol P03;
2,5-hexanediol, 2-methyl- (Me-E I _2); 2,5-hexanediol 2-methyl- POI _2; 2,5-hexanediol, 3-methyl- (Me-EI _2); 2,5-hexanediol 3-methyl- POI _2; 3,4-hexanediol EOI _5;
3,4-hexanediol n-BO I ; 3,4-hexanediol BO I ;
5. I ,3-heptanediol E I _7; 1,3-heptanediol PO I ; I ,3-heptanediol n-BO I _2;
1,4-heptanediol EI_7; 1,4-heptanediol PO I; 1,4-heptanediol n-BOI_2; 1,5-heptanediol EI_7; 1,5-heptanediol POI; 1,5-heptanediol n-BOI_2; 1,6-heptanediol EI_7; 1,6-heptanediol POI ; 1,6-heptanediol n-BO I _2; I ,7-heptanediol E I _2; 1,7-heptanediol n-BOI; 2,4-heptanediol E3_10; 2,4-heptanediol (Me-EI); 2,4-heptanediol POI; 2,4-heptanediol n-B03; 2,5-heptanediol E3_10; 2,5-heptanediol (Me-EI); 2,5-heptanediol POI; 2,5-heptanediol n-B03; 2,6-heptanediol E3_I0; 2,6-heptanediol (Me-EI);
2,6-heptanediol POI; 2,6-heptanediol n-B03; 3,5-heptanediol E3_10; 3,5-heptanediol (Me-EI); 3,5-heptanediol POI; 3,5-heptanediol n-B03;
6. 1,3-butanediol, 3-methyl-2-isopropyl- POI; 2,4-pentanediol, 2,3,3-trimethyl- POI; 1,3-butanediol, 2,2-diethyl- E2_5; 2,4-hexanediol, 2,3-dimethyl- E2_5;
2,4-hexanediol, 2,4-dimethyl- E2_5; 2,4-hexanediol, 2,5-dimethyl- E2_5; 2,4-hexanediol, 3,3-dimethyl- E2_5; 2,4-hexanediol, 3,4-dimethyl- E2_5; 2,4-hexanediol, 3,5-dimethyl-E2_5; 2,4-hexanediol, 4,5-dimethyl- E2_5; 2,4-hexanediol, 5,5-dimethyl- E2_5;
2,5-hexanediol, 2,3-dimethyl- E2_5; 2,5-hexanediol, 2,4-dimethyl- E2_5; 2,5-hexanediol, 2,5-dimethyl- E2-5; 2,5-hexanediol, 3,3-dimethyl- E2_5; 2,5-hexanediol, 3,4-dimethyl- E2_5;
3,5-heptanediol, 3-methyl- E2_5; 1,3-butanediol, 2,2-diethyl- n-BO1_2; 2,4-hexanediol, ~,3-dimethyl- n-BOl _2; ~,4-hexanediol, 2,4-dimethyl- n-BO 1 _2; 2,4-hexanediol, 2,5-dimethyl- n-BOl _2; 2,4-hexanediol, 3,3-dimethyl- n-BOl _2; 2,4-hexanediol, 3,4-dimethyl- n-BO 1 _2; 2,4-hexanediol. 3,5-dimethyl- n-BOl _2; 2,4-hexanediol, 4,5-dimethyl- n-BOl _2; 2,4-hexanediol, 5,5-dimethyl-, n-BOl _2; 2,5-hexanediol, 2,3-dimethyl- n-BOl _2; 2,5-hexanediol, 2.4-dimethyl- n-BO1 _2; 2,5-hexanediol, 2,5-dimethyl- n-BOl _2; 2,5-hexanediol, 3,3-dimethyl- n-BOl _2; 2,5-hexanediol, 3,4-dimethyl- n-BOl_2; 3,5-heptanediol, 3-methyl- n-BOl_2; 1,3-propanediol, 2-(1,2-dimethylpropyl)- n-BOl ; 1,3-butanediol, 2-ethyl-2,3-dimethyl- n-BOl ; 1,3-butanediol, 2-methyl-2-isopropyl- n-BOl ; 1.4-butanediol. 3-methyl-2-isopropyl- n-BOl ;
1,3-pentanediol, 2,2,3-trimethyl- n-BOI; 1,3-pentanediol, 2,2,4-trimethyl- n-BOI;
1,3-pentanediol, 2,4,4-trimethyl- n-BO l ; 1,3-pentanediol, 3,4,4-trimethyl- n-BOl ; 1,4-pentanediol, 2,2,3-trimethyl- n-BOI; 1,4-pentanediol, 2,2,4-trimethyl- n-BO1;
1,4-pentanediol, 2,3,3-trimethyl- n-BOI; 1,4-pentanediol, 2,3,4-trimethyl- n-BO1;
1,4-pentanediol, 3,3,4-trimethyl- n-BOI; ~,4-pentanediol, 2,3,4-trimethyl- n-BO1;
2,4-hexanediol, 4-ethyl- n-BOI; ~,4-heptanediol, 2-methyl- n-BOI; 2,4-heptanediol, methyl- n-BO1; 2,4-heptanediol, 4-methyl- n-BO1; 2,4-heptanediol, 5-methyl- n-BOI;
2,4-heptanediol, 6-methyl- n-BOI; 2,5-heptanediol. 2-methyl- n-BOl; 2,5-heptanediol, 3-methyl- n-BOl ; 2,5-heptanediol, 4-methyl- n-BOl ; 2,5-heptanediol, 5-methyl-n-BO l ;
2,5-heptanediol, 6-methyl- n-BO ~ ; 2,6-heptanediol, 2-methyl- n-BO 1; 2,6-heptanediol, 3-methyl- n-BOl ; 2,6-heptanediol. 4-methyl- n-BO l ; 3,5-heptanediol, 2-methyl- n-BOl ;
1,3-propanediol, 2-(1,2-dimethylpropyl)- E1_3; 1,3-butanediol, 2-ethyl-2,3-dimethyl- El_ 3; 1,3-butanediol, 2-methyl-2-isopropyl- El_3; 1,4-butanediol, 3-methyl-2-isopropyl- El_ 1,3-pentanediol, 2,2,3-trimethyl- El_3; 1,3-pentanediol, 2,2,4-trimethyl-El_3; 1,3-pentanediol, 2,4,4-trimethyl- E 1-3; 1,3-pentanediol, 3,4,4-trimethyl- E 1-3;
1,4-pentanediol, 2,2,3-trimethyl- El_3; 1,4-pentanediol, 2,2,4-trimethyl- E1_3;
1,4-pentanedio'l, 2,3,3-trimethyl- E 1-3; 1,4-pentanediol, 2,3,4-trimethyl- E 1 _3; 1,4-pentanediol, 3,3,4-trimethyl- E1_3; 2,4-pentanediol, 2,3,4-trimethyl- E1_3;
2,4-hexanediol, 4-ethyl- E1_3; 2,4-heptanediol. 2-methyl- El_3; 2,4-heptanediol, 3-methyl-E 1 _3; 2,4-heptanediol, 4-methyl- E ~ -3; 2,4-heptanediol, 5-methyl- E 1 _3;
2,4-heptanediol, 6-methyl- E1_3; 2,5-heptanediol, 2-methyl- El-3; 2,5-heptanediol, 3-methyl-El_3; 2,5-heptanediol, 4-methyl- EI_3; 2,5-heptanediol, 5-methyl- El_3; 2,5-heptanediol, methyl- E1_3; 2,6-heptanediol, 2-methyl- E1_3; 2,6-heptanediol,,3-methyl-E1_3; 2,6-heptanediol, 4-methyl- El_3; and/or 3,5-heptanedioh 2-methyl- El_3; and 7. mixtures thereof;
IX. aromatic diols including: I-phenyl-1,2-ethanediol; 1-phenyl-1,2-propanediol; 2-phenyl-1,2-propanediol; 3-phenyl-1,2-propanediol; I-(3-methylphenyl)-1,3-propanediol;
I-(4-methylphenyl)-1,3-propanediol; 2-methyl-1-phenyl-1,3-propanediol; I-phenyl-1,3-butanediol; 3-phenyl-1,3-butanediol; I-phenyl-1,4-butanediol; 2-phenyl-1,4-butanediol;
and/or 1-phenyl-2,3-butanediol;
X. principal solvents which are homologs, or analogs, of the above structures where one, or more, CH2 groups are added while, for each CH2 group added, two hydrogen atoms are removed from adjacent carbon atoms in the molecule to form one carbon-carbon double bond, thus holding the number of hydrogen atoms in the molecule constant, including the following:
1,3-Propanediol, 2,2-di-2-propenyl-; 1,3-Propanediol, 2-( 1-pentenyl)-; 1,3-Propanediol, 2-(2-methyl-2-propenyl)-2-(2-propenyl)-; 1,3-Propanediol, 2-(3-methyl-I-butenyl)-; 1,3-Propanediol, 2-(4-pentenyl)-; 1,3-Propanediol, 2-ethyl-2-(2-methyl-2-propenyl)-; 1,3-Propanediol, 2-ethyl-2-(2-propenyl)-; 1,3-Propanediol, 2-methyl-2-(3-methyl-3-butenyl)-1,3-Butanediol, 2,2-diallyl-; 1,3-Butanediol, 2-(1-ethyl-I-propenyl)-; 1,3-Butanediol, 2-(2-butenyl)-2-methyl-; 1,3-Butanediol, 2-(3-methyl-2-butenyl)-; 1,3-Butanediol, 2-ethyl-2-(2-propenyl)-; 1,3-Butanediol, 2-methyl-2-(I-methyl-2-propenyl)-; 1,4-Butanediol, 2,3-bis(I-methylethylidene)-; 1,4-Butanedioi, 2-(3-methyl-2-butenyl)-3-methylene-; 2-Butene-1,4-diol, 2-(1,1-dimethylpropyl)-; 2-Butene-1,4-diol, 2-(I-methylpropyl)-; 2-Butene-1,4-diol, 2-butyl-; 1,3-Pentanediol, 2-ethenyl-3-ethyl-; 1,3-Pentanediol, 2-ethenyl-4,4-dimethyl-; 1,4-Pentanediol, 3-methyl-2-(2-propenyl)-; I,5-Pentanediol, 2-(I-propenyl)-; I,5-Pentanediol, 2-(2-propenyl)-; I,5-Pentanediol, 2-ethylidene-3-methyl-;
I,S-Pentanediol, 2-propylidene-; 2,4-Pentanediol, 3-ethylidene-2,4-dimethyl-;
4-Pentene-1,3-diol, 2-(1,1-dimethylethyl)-; 4-Pentene-1,3-diol, 2-ethyl-2,3-dimethyl-;
1,4-Hexanediol, 4-ethyl-2-methylene-; 1,5-Hexadiene-3,4-diol, 2,3,5-trimethyl-;
1,5-Hexadiene-3,4-diol, S-ethyl-3-methyl-; 1,5-Hexanediol, 2-(1-methylethenyl)-;
1,6-Hexanediol, 2-ethenyl-; I-Rexene-3,4-diol, 5,5-dimethyl-; 1-Rexene-3,4-diol, 5,5-dimethyl-;' 2-Rexene-I,5-diol, 4-ethenyl-2,5-dimethyl-; 3-Rexene-1,6-diol, 2-ethenyl-2,5-dimethyl-; 3-Rexene-1,6-diol, 2-ethyl-; 3-Rexene-1,6-diol, 3,4-dimethyl-;
4-Hexene-2,3-diol, 2,5-dimethyl-; 4-Rexene-2,3-diol, 3,4-dimethyl-; 5-Rexene-1,3-diol, 3-(2-propenyl)-; 5-Rexene-2,3-diol, 2,3-dimethyl-; 5-Rexene-2,3-diol, 3,4-dimethyl-; 5-Hexene-2,3-diol, 3,5-dimethyl-; 5-Rexene-2,4-diol, 3-ethenyl-2,5-dimethyl-;
1,4-Heptanediol, 6-methyl-5-methylene-; 1,5-Heptadiene-3,4-diol, 2,3-dimethyl-;
1,5-Heptadiene-3,4-diol, 2,5-dimethyl-; 1,5-Heptadiene-3,4-diol, _3,5-dimethyl-;
1,7-Heptanediol, 2,6-bis(methylene)-; 1,7-Heptanediol, 4-methylene-; I-Heptene-3,5-diol, 2,4-dimethyl-; I-Heptene-3,5-diol, '',6-dimethyl-; I-Heptene-3,5-diol, 3-ethenyl-5-methyl; I-Heptene-3,5-diol, 6,6-dimethyl-; 2,4-Heptadiene-2,6-diol, 4,6-dimethyl-; 2,5-Heptadiene-1,7-diol, 4,4-dimethyl-; ~,6-Heptadiene-1,4-diol, 2,5,5-trimethyl-;

Heptene-1,4-diol, 5,6-dimethyl-; 2-Heptene-1,5-diol, 5-ethyl-; 2-Heptene-i,7-diol, 2-methyl-; 3-Heptene-1,5-diol, 4,6-dimethyl-; 3-Heptene-1,7-diol, 3-methyl-6-methylene-3-Heptene-2,5-diol, 2,4-dimethyl-; 3-Heptene-2.5-diol, 2,5-dimethyl-; 3-Heptene-2,6-diol, 2,6-dimethyl-; 3-Heptene-2,6-diol, 4,6-dimethyl-; 5-Heptene-1,3-diol, 2,4-dimethyl-5-Heptene-1,3-diol, 3,6-dimethyl-; 5-Heptene-l,4-diol, 2,6-dimethyl-; 5-Heptene-1,4 diol, 3,6-dimethyl-; 5-Heptene-2,4-diol, 2,3-dimethyl-; 6- Heptene-1,3-diol, 2,2-dimethyl 6-Heptene-1,4-diol. 4-(2-propenyl)-; 6-Heptene-1,4-diol. 5,6-dimethyl-; 6-Heptene-1,5 diol, 2.4-dimethyl-; 6-Heptene-1,5-diol. 2-ethylidene-6-methyl-; 6-Heptene-2,4-diol, 4-(2-propenyl)-; 6-Heptene-2,4-diol. 5.5-dimethyl-; 6-Heptene-2,5-diol, 4.6-dimethyl-; 6-Heptene-2,5-diol, 5-ethenyl-4-methyl-; I ,3-Octanediol, 2-methylene-; 1,6-Octadiene-3,5-dioi, 2,6-dimethyl-; 1,6-Octadiene-3,5-diol. 3,7-dimethyl-; 1,7-Octadiene-3,6-diol, 2,b-dimethyl-; 1,7-Octadiene-3,6-diol, 2.7-dimethyl-; 1,7-Octadiene-3,6-diol, 3,6-dimethyl-;
I-Octene-3,6-diol, 3-ethenyl-; 2,4,6-Octatriene-1,8-diol, 2,7-dimethyl-; 2,4-Octadiene-1,7-diol, 3,7-dimethyl-; 2.5-Octadiene-1,7-diol, 2,6-dimethyl-; 2,5-Octadiene-1,7-diol, 3,7-dimethyl-; 2,6-Octadiene-1.4-diol, 3,7-dimethyl- (Rosiridol); 2,6-Octadiene-1,8-diol, 2-methyl-; 2,7-Octadiene-1,4-diol, 3,7-dimethyl-; 2,7-Octadiene-1,5-diol, 2,6-dimethyl-;
2,7-Octadiene-1,6-diol, 2,6-dimethyl- (8-Hydroxylinalool); 2,7-Octadiene-1,6-diol, 2,7-dimethyl-; 2-Octene-1,4-diol; 2-Octene-1,7-diol; 2-Octene-1,7-diol, ''-methyl-methylene-; 3,5-Octadiene-1,7-diol. 3.7-dimethyl-; 3,5-Octadiene-2,7-diol, 2,7-dimethyl-3,5-Octanediol, 4-methylene-; 3,7-Octadiene-1,6-diol, 2,6-dimethyl-; 3,7-Octadiene-2,5-diol, 2,7-dimethyl-; 3,7-Octadiene-2,6-diol, 2,6-dimethyi-; 3-Octene-1,5-diol, 4-methyl-; 3-Octene-1,5-diol, 5-methyl-; 4,6-Octadiene-1,3-diol, 2,2-dimethyl-;
4,7-Octadiene-2,3-diol, 2,6-dimethyl-; 4,7-Octadiene-2,6-diol, 2,6-dimethyl-; 4-Octene-1,6-diol, 7-methyl-; 2,7-bis(methylene)-; 2-methylene-; 5,?-Octadiene-1,4-diol, 2,7-dimethyl-; 5,7-Octadiene-1,4-diol, 7-methyl-; 5-Octene-1,3-diol; 6-Octene-1,3-diol, 7-methyl-; 62~ctene-1,4-diol, 7-methyl-; 6-Octene-I,5-diol; 6-Octene-1,5-diol, 7-methyl-;
6-Octene-3,5-diol, 2-methyl-; 6-Octene-3,5-diol, 4-methyl-; 7-Octene-1,3-diol, 2-methyl-7-Octene-1,3-diol, 4-methyl-; 7-Octene-1,3-diol, 7-methyl-; 7-Octene-I,5-diol;

Octene-1,6-diol; 7-Octene-1,6-diol, 5-methyl-; 7-Octene-2,4-diol, 2-methyl-6-methylene 7-Octene-2,5-diol, 7-methyl-; 7-Octene-3,5-diol, 2-methyl-; I-Nonene-3,5-diol;
i Nonene-3,7-diol; 3-Nonene-2,5-diol; 4,6-Nonadiene-1,3-diol, 8-methyl-; 4-Nonene-2,8-diol; 6,8-Nonadiene-1,5-diol; 7-Nonene-2,4-diol; 8-Nonene-2,4-diol; 8-Nonene-2,5-diol;
1,9-Decadiene-3,8-diol; and/or 1,9-Decadiene-4,6-diol; and XI. mixtures thereof;
The clear fabric softening compositions described herein can optionally, but preferably, contain:
( 1 ) an effective amount, sufficient to improve clarity, of low molecular weight water soluble solvents like ethanol, isopropanol, propylene glycol, 1,3-propanediol, propylene carbonate, etc., said water soluble solvents being at a level that will not form clear compositions by themselves;
(2) optionally, but preferably, fiom 0% to about 1 S%, preferably from about 0.1% to about 8%, and more preferably from about 0.2% to about 5%, of perfume;
(3) optionally, from 0% to about 2%, preferably from about 0.01% to about 0.2%, and more preferably from about 0.035% to about 0.1 %, of stabilizer; and (4) optionally, an effective amount to improve clarity, of water soluble calcium and/or magnesium salt, preferably chloride.
The balance of the composition is typically water.
Preferably, the fabric softening compositions herein are aqueous, translucent or clear, preferably clear, compositions containing from about 3% to about 95%, preferably from about 10% to about 80%, more preferably from about 30% to about 70%, and even more preferably from about 40% to about 60%, water and from about 5% to about 40%, preferably from about 7% to about 35%, more preferably from about 10% to about 25%, and even more preferably from about 12% to about 18%, of the above principal alcohol solvent. These preferred products (compositions) are not translucent or clear without the principal solvent. The amount of principal solvent used to make the compositions translucent or clear is preferably more than 50%, more preferably more than about 60%, and even more preferably more than about 75%, of the total organic solvent present.
The principal solvents are desirably kept to the lowest levels that provide acceptable stability/clarity in the present fabric softening compositions. The presence of water exerts an important effect on the need for the principal solvents to achieve clarity of these compositions. The higher the water content, the higher the principal solvent level (relative to the softener active level) is needed to attain product clarity. Inversely, the less the water content, the less principal solvent (relative to the softener active) is needed. Thus, at low water levels of from about 3% to about 15%, the softener active-to-principal solvent weight ratio is preferably from about 55:45 to about 85:15, more preferably from about 60:40 to about 80:20. At water levels of from about 15%
to about 70%, the softener active-to-principal solvent weight ratio is preferably from about 45:55 to about 70:30, more preferably from about 55:45 to about 70:30. But at high water levels of from about 70% to about 80%, the softener active-to-principal solvent weight ratio is preferably from about 30:70 to about 55:4, more preferably from about 35:65 to about 45:55. At higher water levels, the softener active to principal solvent ratios should be even higher.

B. Fabric Softenin~ Active An essential component in the fabric softening compositions described herein is, from about 15% to about 50%, preferably from about 16% to about 35%, more preferably from about 17% to about 30%, by weight of the composition, of a biodegradable fabric softener active selected from the compounds identified hereinafter, and mixtures thereof. The fabric softener active used can be highly unsaturated and/or branched and is preferably biodegradable. The unsaturated compounds should have at least about 3%, e.g., from about 3% to about 30%, of softener active containing polyunsaturated groups. Normally, one would not want polyunsaturated groups in actives, since they tend to be much more unstable than even monounsaturated groups.
The presence of these highly unsaturated materials makes it highly desirable, and for the higher levels of polyunsaturation, essential, that the highly unsaturated and/or branched fabric softening actives and/or compositions herein contain antibacterial agents, antioxidants, and/or reducing materials, to protect the actives from degradation. The long chain hydrocabon groups can also comprise branched chains, e.g., from isostearic acid, for at least part of the groups. The total of active represented by the branched chain groups, when they are present, is typically from about 1 % to about I 00%, preferably from about 10% to about 70%, more preferably from about 20% to about 50%.
Diester Ouaternary Ammonium Fabric Softeni~ Active Compound (DEOA~
( 1 ) The first type of DEQA preferably comprises, as the principal active, compounds of the formula ~R)4-m - NC+) - WH2)n - Y- R elm X{-) (1) wherein each R substituent is a short chain C1-C6, preferably CI-C3 alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl or mixtures thereof; each m is 2 or 3; each n is from I to about 4; each Y is -O-(O)C-, -C(O)-O-, -(R)N-(O)C, or -C(O)-N(R)-; the sum of carbons in each R1, plus one when Y is -O-{O)C- or -(R)N-(O)C-, is C I 2-C22, preferably C 14-C20, with each R 1 being a hydrocarbyl, or substituted hydrocarbyl group, including straight and branched chain alkyls. Preferably, the softener active contains alkyl, monounsaturated alkylene, and polyunsaturated alkylene groups, with the softener active containing polyunsaturated alkylene groups being at least about 3%, e.g., from about 3% to about 30%, by weight of the total softener active present. (As used herein, the "percent of softener active"

containing a given R1 group is based upon taking a percentage of the total active based upon the percentage that the given R1 group is, of the total R1 groups present.) The Iodine Value (hereinafter referred to as IV) of the parent fatty acids of these R1 group is preferably from about 60 to about 140, more preferably from about 70 to about 130; and even more preferably from about 7~ to about 115, on the average. It is believed that the actives which comprise unsaturated R1 groups are preferably from about 50% to about 100%, more preferably from about 55% to about 95°ra, and even more preferably from about 60% to about 90%, by weight of the total active present. The actives containing polyunsaturated R1 groups are at least about 3%, preferably at least about ~%, and more preferably at least about 10%, and yet more preferably at least about 15%, by weight, of the total actives present. These polyunsaturated groups are necessary to provide optimum viscosity stability, especially after freezing and thawing.
The higher the level of polyunsaturated R1 groups in the actives, the lower the level of actives which comprise unsaturated R1 groups can be.
The counterion, X(-~ above, can be any softener-compatible anion, preferably the anion of a strong acid, for example, chloride, bromide, methylsulfate, sulfate, nitrate and the like. and more preferably chloride.
These biodegradable quaternary ammonium fabric softening compounds preferably contain the group C(O)R1 which is derived, primarily from unsaturated fatty acids, e.g., oleic acid, the preferred polyunsaturated fatty acids, and/or saturated fatty acids, and/or partially hydrogenated fatty acids from natural sources, e.g., derived from animal fats, vegetable oils and/or partially hydrogenated vegetable oils, such as, canola oil, safflower oil, peanut oil, sunflower oil, corn oil, soybean oil, tall oil, rice bran oil, etc. In other preferred embodiments, the fatty acids have the following approximate distributions:
Fatty Acyl Group DE A1 DEOA~ DEOA3 DE A4 DEQA~
C 12 trace trace 0 0 0 C16 ~ 4 4 5 5 5 C18 0 0 ~ 6 6 C14:1 3 3 0 0 0 C16:1 11 7 0 0 3 C 18:1 74 73 71 68 67 C18:2 4 8 8 11 11 C18:3 0 1 1 2 2 C20:1 0 0 2 2 2 C20 and 0 0 2 0 up Unknowns 0 0 6 6 7 Total 99 99 100 100 102 cis/trans (C 18:1 ) 20-30 20-30 4 S 5 Nonlimiting examples of DEQA's are as follows:
Fatty Acyl DEOA 10 DEOA 11 Group C14:1 0 0 C16:1 1 0 C18:1 27 45 C18:2 50 6 C18:3 7 0 Unknowns 0 3 Total 100 100 cis/trans Not 7 (C 18:1 ) Available DEQA10 is prepared from a soy bean fatty acid, and DEQA11 is prepared from a slightly hydrogenated tallow fatty acid.
It is preferred that at least a majority of the fatty acyl groups are unsaturated, e.g., from about 50% to 100%, preferably from about 55% to about 95%, more preferably from about 60% to about 90%, and that the total level of active containing polyunsaturated fatty acyl groups (TPU) be from about 3% to about 30%, preferably from about 5% to about 25%, more preferably from about 10% to about 18%. The cis/trans r4tio for the unsaturated fatty acyl groups is important, with a cis/trans ratio of from 1:1 to about 50:1, the minimum being 1:1, preferably at least 3:1, and more preferably from about 4:1 to about 20:1.
The unsaturated, including the preferred polyunsaturated, fatty acyl groups surprisingly provide effective softening, but also provide better rewetting characteristics, good antistatic characteristics, and superior recovery after freezing and thawing.
The highly unsaturated materials are also easier to formulate into concentrated premixes that maintain their low viscosity and are therefore easier to process; e.g., pump, mixing, etc. These highly unsaturated materials with only a low amount of solvent that normally is associated with such materials, i.e., from about 5% to about 20%, preferably from about 8% to about 25%, more preferably from about 10% to about 20%, weight of the total softener/solvent mixture, are also easier to formulate into concentrated, stable dispersion compositions of the present invention, even at ambient temperatures. This ability to process the actives at low temperatures is especially important for the polyunsaturated groups, since it mimimizes degradation. Additional protection against degradation can be provided when the compounds and softener compositions contain effective antioxidants and/or reducing agents, as disclosed hereinafter.
It will be understood that substituents R and R1 can optionally be substituted with various groups such as alkoxyl or hydroxyl groups, so long as the R1 groups maintain their basically hydrophobic character. The preferred compounds can be considered to be biodegradable diester variations of ditallow dimethyl ammonium chloride ( hereinafter referred to as "DTDMAC"), which is a widely used fabric softener. A preferred long chain DEQA is the DEQA prepared from sources containing high levels of polyunsaturation, i.e., N,N-di(acyl-oxyethyl)-N,N-dimethyl ammonium chloride, where the acyl is derived from fatty acids containing sufficient polyunsaturation.
As used herein, when the diester is specified, it can include the monoester that is present. Preferably, at least about 80% of the DEQA is in the diester form, and from 0%
to about 20% can be DEQA monoester (e.g., in formula (1), m is 2 and one YR1 group is either "H" or "-C-(O)-OH"). For softening, under no/low detergent carry-over laundry conditions the percentage of monoester should be as low as possible, preferably no more than about 5%. 1-Iowever, under high, anionic detergent surfactant or detergent builder carry-over conditions, some monoester or monoamide can be preferred. The overall ratios of diester to monoester, or diamide to monoamide, are from about 100:1 to about 2:1, preferably from about 50:1 to about 5:1, more preferably from about I 3:1 to about 8: i . Under high detergent carry-over conditions, the di/monoester ratio i5 preferably about 11:1. The level of monoester, or monoamide, present can be controlled in manufacturing the DEQA.
The above compounds, used as the biodegradable quaternized ester-amine, or amido-amine, softening material in the practice of this invention, can be prepared using standard reaction chemistry. In one synthesis of a di-ester variation of DTDMAC, an amine of the formula RN(CH2CH20H)2 is esterified at both hydroxyl groups with an acid chloride of the formula R1C(O)C1, then quaternized with an alkyl halide, RX, to yield the desired reaction product (wherein R and R1 are as defined hereinbefore).
However, it will be appreciated by those skilled in the chemical arts that this reaction sequence allows a broad selection of agents to be prepared.

Yet another DEQA softener active that is suitable for the formulation of the concentrated, liquid fabric softener compositions of the present invention, has the above formula ( 1 ) wherein one R group is a C 1 _4 hydroxy alkyl group, or polyalkoxy group, preferably one wherein one R group is a hydroxyethyi group. An example of such a hydroxyethyl ester active is di(acyloxyethyl)(2-hydroxyethyl)methyl ammonium methyl sulfate, where the acyl is derived from the fatty acids described hereinbefore. Another example of this type of DEQA is derived from the same fatty acid as that of DEQAl, and is denoted hereinafter as DEQAB.
(2) A second type of DEQA active has the general formula:
R 1-Y C HZ ~ + (-) CHCH2N( )R3 X

R -Y~
(2) wherein each Y, R, Rl, and X(-) have the same meanings as before. Such compounds include those having the formula:
[CH3]3 N(+)[CH2CH(CH20C[O]Rl)OC(O)Rl] C1(') where each R is a methyl or ethyl group and preferably each R 1 is in the range of C 15 to C 1 g. As used herein, when the diester is specified, it can include the monoester that is present. The amount of monoester that can be present is the same as in DEQA ( 1 ).
These types of agents and general methods of making them are disclosed in U.S.
Pat. No. 4,137,180, Naik et al., issued Jan. 30, 1979, which is incorporated herein by reference. An example of a preferred DEQA of formula (2) is the "propyl" ester quaternary ammonium fabric softener active having the formula 1,2-di(acyloxy)-trimethylammoniopropane chloride, where the acyl is the same as that of DEQAS, and is a denoted hereinafter as DEQA9.
(3) a third type of DEQA softener active has the general formula:
[RC(O)OC2H4]nN+(Rl)m X_ wherein each R in a compound is a C6-C22 hydrocarbyl group, preferably having an IV
from about 70 to about 140 based upon the IV of the equivalent fatty acid with the cis/trans ratio preferably being as described hereinafter, n is a number from 1 to three on the weight average in any mixture of compounds, each R1 in a compound is a C 1 _3 alkyl or hydroxy alkyl group, the total of n and the number of RI groups that are hydroxyethyl groups equaling 3, n+m equaling 4, and X is a softener compatible anion, preferably methyl sulfate. Preferably the cisarans isomer ratio of the fatty acid (of the C 18: I
component) is at least about 1:1, preferably about 2:1, more preferably 3:1, and even more preferably about 4: I , or higher.
Preferred biodegradable fabric softener compounds of the third type of DIJQA
softener active described hereinbefore comprise quaternary ammonium salt, the quaternized ammonium salt being a quaternized product of condensation between:
a)-a fraction of saturated or unsaturated, linear or branched fatty acids, or of derivatives of said acids, said fatty acids or derivatives each possessing a hydrocarbon chain in which the number of atoms is between ~ and 21. and b)-triethanolamine, characterized in that said condensation product has an acid value, measured by titration of the condensation product with a standard KOH solution against a phenolphthalein indicator, of less than about 6.5.
The acid value is preferably less than or equal to about 5, more preferably less than about 3. Indeed, the lower the AV, the better softness softness performance is obtained.
The acid value is determined by titration of the condensation product with a standard KOH solution against a phenolphthalein indicator according to ISO#t53402. The AV is expressed as mg KOI-I/g of the condensation product.
For optimum softness benefit. it is preferred that the reactants are present in a molar ratio of fatty acid fraction to triethanolamine of from about I :1 to about 2.5:1.
It has also been found that the optimum softness performance is also affected by the detergent carry-over laundry conditions, and more especially by the presence of the anionic surfactant in the solution in which the softening composition is used.
Indeed, the presence of anionic surfactant that is usually carried over from the wash will interact with the softener compound, thereby reducing its performance. Thus, depending on usage r conditions, the mole ratio of fatty acid/ triethanolamine can be critical.
Accordingly, where no rinse occurs between the wash cycle and the rinse cycle containing the softening compound, a high amount of anionic surfactant will be carried over in the rinse cycle containing the softening compound. In this instance, it has been found that a fatty acid fraction/triethanolamine mole ratio of about 1.4:1 to about 1.8:1 is preferred. By high amount of anionic surfactant, it is meant that the presence of anionic in the rinse cycle at a level such that the molar ratio anionic surfactant/cationic softener compound of the invention is at least about 1/10.

Thus, according to another aspect of the invention, there is provided a method of treating fabrics which comprises the step of contacting the fabrics in an aqueous medium containing the softener compound of the invention or softening composition thereof wherein the fatty acid /triethanolamine mole ratio in the softener compound is from about 1.4:1 to about 1.8:1, preferably about 1.5:1 and the aqueous medium comprises a molar ratio of anionic surfactant to said softener compound of the invention of at least about 1:10.
Where, on the other hand, an intermediate rinse cycle occurs between the wash and the later rinse cycle, less anionic surfactant, i.e. less than about 1:10 of a molar ratio anionic surfactant to cationic compound of the invention, will then be carried over.
Accordingly, it has been found that a fatty acid / triethanolamine mole ratio of about 1.8:1 to about 2.2:1 is then preferred. Accordingly, in another aspect of the invention, there is provided a method of treating fabrics which comprises the step of contacting the fabrics in an aqueous medium containing the softener compound of the invention or softening composition thereof wherein the fatty acid/triethanolamine mole ratio in the softener compound is from about 1.8:1 to about 2:1, preferably about 2.0:1 and the aqueous medium comprises a molar ratio of anionic surfactant to said softener compound of the invention of less than about 1:10.
In a preferred embodiment of the invention, the fatty acid fraction and the triethanolamine are present in a molar ratio of from about 1:1 to about 2.5:1.
The DEQA actives described hereinabove can contain a low level of the fatty acids which can be unreacted starting material and/or by-product of any partial degradation, e.g., hydrolysis, of the softener actives in the finished compositions. It is preferred that the level of free fatty acid be low, preferably below about 10%, more preferably below about S%, by weight of the softener active.
Other, less biodegradable fabric softeners that can also be used herein, at least in part, are disclosed, at least generically, for the basic structures, in U.S.
Pat. Nos.
3,861,870, Edwards and Diehl; 4,308,151, Cambre; 3,886,075, Bernardino;
4,233,164, r Davis; 4,401,578, Verbruggen; 3,974,076, Wiersema and Rieke; and 4,237,016, Rudkin, Clint, and Young, all of said patents being incorporated herein by reference.
Other fabric softening agents are further disclosed in U.S. Pat. No.
4,661,269, issued April 28, 1987, to Toan Trinh, Errol H. Wahl, Donald M. Swartley and Ronald L.
Hemingway, said patent being incorporated herein by reference.
Other primary fabric softener actives that can be used in the fabric softening compositions described herein are those that are highly unsaturated versions of the traditional softener actives, i.e., di-long chain alkyl nitrogen derivatives, normally cationic materials, such as dialkyldimethylammonium chloride and imidazolinium compounds as described hereinafter. As discussed in more detail hereinbefore and hereinafter, more biodegradable fabric softener compounds can be present.
Examples of such fabric softeners can be found in U.S. Pat. Nos. 3,408,361, Mannheimer, issued Oct. 29, 1968; 4,709,045. Kubo et al., issued Nov. 24, 1987; 4,233.451, Pracht et al., issued Nov. 11, 1980; 4,127,489, Pracht et al., issued Nov. 28, 1979;
3,689,424, Berg et al., issued Sept. 5, 1972; 4,128,485, Baumann et al., issued Dec. ~, 1978;
4,161,604, Elster et al., issued July 17, 1979; 4,189,593, Wechsler et al., issued Feb. I

9, 1980; and 4,339,391, Hoffman et al., issued July 13, 1982, said patents being incorporated herein by reference.
Accordingly, the fabric softener actives used in the present invention can also comprise a majority of compounds as follows:
(4) softener active having the formula:
R4_m - Ny) - R 1 m A-wherein each m is 2 or 3, each R1 is a C6-C22, preferably C14-C20, but no more than one being less than about C 12 and then the other is at least about 16, hydrocarbyl, or substituted hydrocarbyl substituent, preferably C 10-C20 alkyl or alkenyl (unsaturated alkyl, including polyunsaturated alkyl, also referred to sometimes as "alkylene"), most preferably C 12-C 1 g alkyl or alkenyl, and where the Iodine Value of a fatty acid containing this Rl group is from about 70 to about 140, more preferably from about 80 to about 130; and most preferably from about 90 to about 115 with a cis/trans ratio of from about 1:1 to about 50:1, the minimum being 1:1, preferably from about 2:1 to about 40:1, more preferably from about 3:1 to about 30:1, and even more preferably from about 4:1 to about 20:1; each R1 can also preferably be a branched chain C14-C22 alkyl group, preferably a branched chain C 16-C 1 g group; each R is H or a short chain C 1-C6, preferably C1-C3 alkyl or hydroxyalkyl group, e.g., methyl (most preferred), ethyl, propyl, hydroxyethyl, and the like, benzyl, or (R2 O)2-4I-I; and A- is a softener compatible anion, preferably, chloride, bromide, methylsulfate, ethylsulfate, sulfate, and nitrate, more preferably chloride and methyl sulfate;
(5) softener active having the formula:

R1 C I A _ O
1 ~ N+ CH2 R C G R2~ \
R
wherein each R, R1, and A' have the definitions given above; each R2 is a C1_6 alkylene group, preferably an ethylene group; and G is an oxygen atom or an -NR- group, (6) softener active having the formula:
R'-C N-CH2 O N-CHz Rt-C-G_ Rz~
wherein R 1, R2 and G are defined as above;
(7) reaction products of substantially unsaturated and/or branched chain higher fatty acids with dialkylenetriamines in, e.g., a molecular ratio of about 2:1, said reaction products containing compounds of the formula:
R1~(O~-NH-RZ-NH-R3 NH--C(O}-R1 wherein R l , R2 are defined as above, and each R3 is a C 1 _6 alkylene group, preferably an ethylene group;
(8) softener active having the formula:
[R1--C(O~NR-R' N(R)2-R3-NR-C:(U)--Rl]+ A-wherein R, R 1, R2, R3 and A- are defined as above;
(9) the reaction product of substantially unsaturated and/or branched chain higher fatty acid with hydroxyalkylalkylenediamines in a molecular ratio of about 2:1, said reaction products containing compounds of the formula:
Rl-C(O)-NH-R2-N(R30H)-C(O)-R1 wherein R1, R2 and R3 are defined as above;
( 10) softener active having the formula:
R R
N-R~-N
N ~N ~AO
Ri R~
wherein R, R1, R2, and A- are defined as above; and { 11 ) mixtures thereof.
Examples of Compound (4) are dialkylenedimethylammonium salts such as dicanoladimethylammonium chloride, dicanoladimethylammonium methylsulfate, di(partially hydrogenated soybean, cis/trans ratio of about 4:1)dimethylammonium chloride, dioleyldimethylammonium chloride. Dioleyldimethylammonium chloride and di(canola)dimethylammonium chloride are preferred. An example of commercially available dialkylenedimethylammonium salts usable in the present invention is dioleyldimethylammonium chloride available from Witco Corporation .under the trade name Adogen~ 472.
An example of Compound (5) is 1-methyl-1-oleylamidoethyl-2-oleylimidazolinium methylsulfate wherein R1 is an acyclic aliphatic C 15-C 17 hydrocarbon group, R2 is an ethylene group, G is a NH group, RS is a methyl group and A- is a methyl sulfate anion, available commercially from the Witco Corporation under the trade name Varisoft~ 3690.

An example of Compound (6) is 1-oleylamidoethyl-2-oleylimidazoline wherein R1 is an acyclic aliphatic C 15-C 17 hydrocarbon group, R2 is an ethylene group, and G is a NH group.
An example of Compound {7) is reaction products of oleic acids with diethylenetriamine in a molecular ratio of about 2:1, said reaction product mixture containing N,N"-dioleoyldiethylenetriamine with the formula:
R 1-C(O)-NH-Cl-12CH2-Nl-1-CH2CH2-NH-C(O)-R 1 wherein R1-C(O) is oleoyl group of a commercially available oleic acid derived from a vegetable or animal source, such as Emersol~ 223LL or Emersol~ 7021, available from Henkel Corporation. and R2 and R3 are divalent ethylene groups.
An example of Compound (8) is a difatty amidoamine based softener having the formula:
[R1-C(O)-NH-CH2CH2-N(CH3)(CH2CH20H)-CH2CH2-NH-C(O)-R1]+ CH3S04-wherein R1-C(O) is oleoyl group, available commercially from the Witco Corporation under the trade name Varisoft~ 222LT.
An example of Compound (9) is reaction products of oleic acids with N-2-hydroxyethylethylenediamine in a molecular ratio of about 2:1, said reaction product mixture containing a compound of the formula:
R1-C(O)-NH-CH2CH2-N(CH2CH20H)-C(O)-R1 wherein R1-C(O) is oleoyl group of a commercially available oleic acid derived from a vegetable or animal source, such as Emersoln 223LL or Emersol~ 7021, available from Henkel Corporation.
An example of Compound ( 10) is the diquaternary compound having the formula:
CH3 CH3~

N~ ~N
Rt R1 wherein R1 is derived from oleic acid, and the compound is available from Witco Company.
The above individual fabric softener actives can be used individually or as mixtures.

One type of optional but highly desirable cationic compound which can be used in combination with the above softener actives are compounds containing one long chain acyclic Cg-C~~ hydrocarbon group, selected from the group consisting of:
( 12) acyclic quaternary ammonium salts having the formula:
~Rl N(RS)~_R61+ A_ wherein R~ and R~' are C 1-C4 alkyl or hydroxyalkyl groups, and Rl and A- are defined as herein above, ( 13) substituted imidazolinium salts having the formula:
O
N-CH~
Rl-Cv I AO
N-CHI
R~~ ~ H
wherein R~ is hydrogen or a Cl-C4 saturated alkyl or hydroxyalkyl group. and Rl and A- are defined as herein above;
( 14) substituted imidazolinium salts having the formula:
O
Rt-CN-CH2 Ao N-CI-h HO-R'- ~ ~ Rs wherein R~ is a Cl-C4 alkyl or hydroxyalkyl group, and Rl, R~, and A' are as defined above;
(15) alkylpyridinium salts having the formula:
O

wherein R4 is an acyclic aliphatic Cg-C2~ hydrocarbon group and A- is an anion; and ( 16) alkanamide alkylene pyridinium salts having the formula:
O O
R~-C-NH-R'--N O AO
wherein R l , R2 and A- are defined as herein above; and mixtures thereof.
Examples of Compound (12) are the monoalkenyltrimethylammonium salts such as monooleyltrimethylammonium chloride, monocanolatrimethylammonium chloride, and soyatrimethylammonium chloride. Monooleyltrimethylammonium chloride and monocanolatrimethylammonium chloride are preferred. Other examples of Compound (12) are soyatrimethylammonium chloride available from Witco Corporation under the trade name Adogen~ 415, erucyltrimethylammonium chloride wherein R1 is a C22 hydrocarbyl group derived from a natural source; soyadimethylethylammonium ethylsulfate wherein R 1 is a C 16-C 1 g hydrocarbon group, RS is a methyl group, R6 is an ethyl group, and A' is an ethylsulfate anion; and methyl bis(2-hydroxyethyl)oleylammonium chloride wherein R I is a C 1 g hydrocarbyl group, RS is a 2-hydroxyethyl group and R6 is a methyl group.
An example of Compound (14) is 1-ethyl-1-(2-hydroxyethyl)-2-isoheptadecylimidazolinium ethylsulfate wherein R1 is a C1~ hydrocarbyl group, R2 is an ethylene group, RS is an ethyl group, and A- is an ethylsulfate anion.
[In preferred quaternary ammonium fabric softening compounds, and especially DEQAs, -(O)CR1 is derived from unsaturated fatty acid, e.g., oleic acid, and/or fatty acids and/or partially hydrogenated fatty acids, derived from animal fats, vegetable oils and/or partially hydrogenated vegetable oils, such as: canola oil; safflower oil; peanut oil;
sunflower oil; soybean oil; corn oil; tall oil; rice bran oil; etc.] [As used herein, biodegradable fabric softener actives containing ester linkages are referred to as "DEQA", which includes both diester, triester, and monoester compounds containing r from one to three, preferably two, long chain hydrophobic groups. The corresponding amide softener actives and the mixed ester-amide softener actives can also contain from one to three, preferably two, long chain hydrophobic groups. These fabric softener actives have the characteristic that they can be processed by conventional mixing means at ambient temperature, at least in the presence of about 15% of solvent C. as disclosed herein.]
Anion A

In the cationic nitrogenous salts herein, the anion A- , which is any softener compatible anion, provides electrical neutrality. Most often, the anion used to provide electrical neutrality in these salts is from a strong acid, especially a halide, such as chloride, bromide, or iodide. However, other anions can be used, such as methylsulfate, ethylsulfate, acetate, formate. sulfate, carbonate, and the Like. Chloride and methylsulfate are preferred herein as anion A.
C. Optional Ingredients 1. Perfume The fabric softening compositions of the present invention can contain any softener compatible perfume. Preferred perfumes are disclosed in U.S. Pat.
5,500,138, Bacon et al., issued March 19. 1996, said patent being incorporated herein by reference.
Perfume is optionally present at a level of from about 0% to about 10%, preferably from about 0.1% to about 5%, more preferably from about 0.2% to about 3%, by weight of the finished composition. It is an advantage of the use of this invention, that the perfume preferably can be added in the premix to simplify the preparation of the finished dispersion compositions and to improve fabric deposition of said perfume. The premix can be added to water containing the requisite amount of acid, preferably mineral acid, more preferably HC1. to create the finished composition as discussed hereinafter.
~. Stabilizers Stabilizers are highly desirable. and even essential, in the fabric softening compositions, and, optionally, the raw materials, of the present invention.
The term "stabilizer," as used herein, includes antioxidants and reductive agents.
These agents are present at a level of fiom 0% to about 2%, preferably from about 0.01 % to about 0.2%, more preferably from about 0.035% to about 0.1% for antioxidants, and more preferably from about 0.01% to about 0.2% for reductive agents, in the final composition.
For the premix, the levels are adjusted, depending on the concentrations of the softener active in the premix and the finished composition. These assure good odor stability under long term storage conditions. Antioxidants and reductive agent stabilizers are especially critical for unscented or low scent products (no or low perfume).
Examples of antioxidants that can be added to the fabric softening compositions of this invention include a mixture of ascorbic acid, ascorbic palmitate, propyl gallate, available from Eastman Chemical Products, Inc., under the trade names TenoxO
PG and Tenox~ S-1; a mixture of BHT (butylated hydroxytoluene), BHA (butylated hydroxyanisole), propyl gallate, and citric acid, available from Eastman Chemical Products, Inc., .under the trade name Tenox~-6; butylated hydroxytoluene, available from UOP Process Division under the trade name Sustane~ BHT; tertiary butylhydroquinone, Eastman Chemical Products, Inc., as Tenox~ TBHQ; natural tocopherols, Eastman Chemical Products, Inc., as Tenox~ GT-1/GT-2; and butylated hydroxyanisole, Eastman Chemical Products, Inc., as BHA; long chain esters (Cg-C22) of gallic acid, e.g., dodecyl gallate; IrganoxC~ 1010; Irganox~ 1035; Irganox~
B 1171;
Irganox0 1425; Irganox~ 3114; Irganoxc~ 3125; and mixtures thereof; preferably Irganox~ 3125, Irganox~ 1425, Irganox~ 3114, and mixtures thereof; more preferably Irganox~ 3125 alone or mixed with citric acid and/or other chelators such as isopropyl citrate, Dequest0 2010, available from Monsanto with a chemical name of 1-hydroxyethylidene-1, 1-diphosphonic acid (etidronic acid), and TironU, available from Kodak with a chemical name of 4,5-dihydroxy-m-benzene-sulfonic acid/sodium salt, and DTPA~, available from Aldrich with a chemical name of diethylenetriaminepentaacetic acid.
3. Brighteners The fabric softening compositions herein can also optionally contain from about 0.005% to 5% by weight of certain types of hydrophilic optical brighteners which also provide a dye transfer inhibition action. If used, the fabric softening compositions herein will preferably comprise from about 0.001 % to 1 % by weight of such optical brighteners.
The hydrophilic optical brighteners useful in the present invention are those having the structural formula:
R~~ R2 ~N H H NO
NOON O ~ ~ O N OO N
ON H H NO
R2 S03M S~3M R~
wherein R1 is selected from anilino, N-2-bis-hydroxyethyl and NH-2-hydroxyethyl; R2 is selected from N-2-bis-hydroxyethyl, N-2-hydroxyethyl-N-methylamino, morphilino, chloro and amino; and M is a salt-forming cation such as sodium or potassium.
When in the above formula, R1 is anilino, R2 is N-2-bis-hydroxyethyl and M is a r cation such as sodium, the brightener is 4,4',-bis[(4-anilino-6-(N-2-bis-hydroxyethyl)-s-triazine-2-yl)amino]-2,2'-stilbenedisulfonic acid and disodium salt. This particular brightener species is commercially marketed under the tradename Tinopal-LTNPA-GX~
by Ciba-Geigy Corporation. Tinopal-UNPA-GX is the preferred hydrophilic optical brightener useful in the fabric softening compositions herein.
When in the above formula, R1 is anilino, R2 is N-2-hydroxyethyl-N-2-methylamino and M is a cation such as sodium, the brightener is 4,4'-bis[(4-anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazine-2-yl)amino]2,2'-stilbenedisulfonic acid disodium salt. This particular brightener species is commercially marketed under the tradename Tinopal SBM-GX~J by Ciba-Geigy Corporation.
When in the above formula, RI is anilino, R2 is morphilino and M is a canon such as sodium, the brightener is 4,4'-bis[(4-anilino-6-morphilino-s-triazine-yl)amino]2,2'-stilbenedisulfonic acid. sodium salt. This particular brightener species is commercially marketed under the tradename Tinopal AMS-GX~ by Ciba Geigy Corporation.

4. Dispersibilit Aids The fabric softening compositions of the present invention can optionally contain dispersibility aids, e.g., those selected from the group consisting of mono-long chain alkyl cationic quaternary ammonium compounds, mono-long chain alkyl amine oxides, and mixtures thereof, to assist in the formation of the finished fabric softening compositions. When said dispersibility aid is present , it is typically present at a total level of from about 2% to about 25%, preferably from about 3% to about 17%, more preferably from about 4% to about 15%, and even more preferably from 5% to about 13% by weight of the composition. These materials can either be added as part of the active softener raw material, (I), or added as a separate component. The total level of dispersibility aid includes any amount that may be present as part of component (I).
a. Mono-Alkyl Cationic Quaternary Ammonium Compound When the mono-alkyl cationic quaternary ammonium compound is present, it is typically present at a level of from about 2% to about 25%, preferably from about 3% to about 17%, more preferably from about 4% to about 15%, and even more preferably from S% to about 13% by weight of the composition, the total mono-alkyl cationic quaternary ammonium compound being at least at an effective level.
Such mono-alkyl cationic quaternary ammonium compounds useful in the present invention are, preferably, quaternary ammonium salts of the general formula:
~R4N+(R5)3~ X_ wherein R4 is Cg-C22 alkyl or alkenyl group, preferably C 10-C 1 g alkyl or alkenyl group; more preferably C 10-C 14 or C 16-C 1 g alkyl or alkenyl group;
each RS is a C 1-C6 alkyl or substituted alkyl group (e.g., hydroxy alkyl), preferably C 1-C3 alkyl group, e.g., methyl (most preferred), ethyl, propyl, and the like, a benzyl group, hydrogen, a polyethoxylated chain with from about 2 to about 20 oxyethylene units, preferably from about 2.5 to about 13 oxyethylene units, more preferably from about 3 to about 10 oXyethylene units, and mixtures thereof; and X- is as defined hereinbefore for (Formula (I)).
Especially preferred dispersibility aids are monolauryl trimethyl ammonium chloride and monotallow trimethyl ammonium chloride available from Witco under the trade name Varisoft~ 471 and monooleyl trimethyl ammonium chloride available from Witco under the tradename Varisoft~ 417.
The R4 group can also be attached to the cationic nitrogen atom through a group containing one, or more, ester, amide, ether, amine, etc., linking groups which can be desirable for increased concentratability of component (I), etc. Such linking groups are preferably within from about one to about three carbon atoms of the nitrogen atom.
Mono-alkyl cationic quaternary ammonium compounds also include Cg-C2~
alkyl choline esters. The preferred dispersibility aids of this type have the formula:
R1C(O)-O-CH~CH~N+(R)3 X-wherein R 1, R and X- are as defined previously.
Highly preferred dispersibility aids include C 1 ~-C 14 coco choline ester and C 1 g tallow choline ester.
Suitable biodegradable single-long-chain alkyl dispersibility aids containing an ester linkage in the long chains are described in U.S. Pat. No. 4.840,738, Hardy and Walley, issued June 20, 1989, said patent being incorporated herein by reference.
When the dispersibility aid comprises alkyl choline esters, preferably the dispersion compositions also contain a small amount, preferably from about 2%
to about 5% by weight of the composition, of organic acid. Organic acids are described in European Patent Application No. 404,471, Machin et al., published on Dec. ?7, 1990, supra, which is herein incorporated by reference. Preferably the organic acid is selected from the group consisting of glycolic acid. acetic acid, citric acid, and mixtures thereof.
Ethoxylated quaternary ammonium compounds which can serve as the dispersibility aid include ethylbis(polyethoxy ethanol)alkylammonium ethyl-sulfate with 17 moles of ethylene oxide, available under the trade name Variquat~ 66 from Sherex Chemical Company: polyethylene glycol ( 15) oleammonium chloride, available under the trade name Ethoquad'~ 0/25 from Akzo; and polyethylene glycol (15) cocomonium chloride, available under the trade name Ethoquad~ C/25 from Akzo.
Although the main function of the dispersibility aid is to increase the dispersibility of the ester softener, preferably the dispersibility aids of the present invention also have some softening properties to boost softening performance of the composition. Therefore, preferably the fabric softening compositions of the present invention are essentially free of non-nitrogenous ethoxylated nonionic dispersibility aids which will decrease the overall softening performance of the fabric softening compositions.
Also, quaternary compounds having only a single long alkyl chain, can protect the cationic softener from interacting with anionic surfactants and/or detergent builders that are earned over into the rinse from the wash solution.
b. Amine Oxides Suitable amine oxides include those with one alkyl or hydroxyalkyl moiety of about 8 to about 22 carbon atoms, preferably from about 1 U to about 18 carbon atoms, more preferably from about 8 to about I4 carbon atoms, and two alkyl moieties selected tiom the group consisting of alkyl groups and hydroxyalkyl groups with about 1 to about 3 carbon atoms.
Examples include dimethyloctylamine oxide, diethyldecylamine oxide, bis-(2-hydroxyethyl)dodecyl-amine oxide, dimethyldodecylamine oxide, dipropyl-tetradecylamine oxide, methylethylhexadecylamine oxide, dimethyl-2-hydroxyoctadecylamine oxide, and coconut fatty alkyl dimethylamine oxide.
5. Soil Release Agent In the present invention, an optional soil release agent can be added, especially to the finished fabric softening compositions. The addition of the soil release agent can occur in combination with a premix, in combination with the acid/water seat, before or after electrolyte addition, or after the final composition is made. The finished softening composition prepared by the process of the present invention herein can contain from 0%
to about 10%, preferably from 0.2% to about S%, of a soil release agent. The concentration in the premix is adjusted to provide the desired end concentration.
Preferably, such a soil release agent is a polymer. Polymeric soil release agents useful in the present invention include copolymeric blocks of terephthalate and polyethylene oxide or polypropylene oxide, and the like.
A preferred soil release agent is a copolymer having blocks of terephthalate and polyethylene oxide. More specifically, these polymers are comprised of repeating units of ethylene terephthalate and polyethylene oxide terephthalate at a molar ratio of ethylene terephthalate units to polyethylene oxide terephthalate units of from 25:75 to about 35:65, said polyethylene oxide terephthalate containing polyethylene oxide blocks having molecuiar weights of from about 300 to about 2000. The molecular weight of this polymeric soil release agent is in the range of from about 5,000 to about 55,000.
Another preferred polymeric soil release agent is a crystallizable polyester with repeat units of ethylene terephthalate units containing from about 10% to about 15% by weight of ethylene terephthaiate units together with from about 10% to about 50% by weight of polyoxyethylene terephthalate units, derived from a polyoxyethylene glycol of average molecular weight of from about 300 to about 6,000, and the molar ratio of ethylene terephthalate units to polyoxyethylene terephthalate units in the crystallizable polymeric compound is between 2:1 and 6:1. Examples of this polymer include the commercially available materials ZeIcon 4780~ (from Dupont) and Milease T~
(from ICI).

Highly preferred soil release agents are polymers of the generic formula:
O
14 II 15 I 14_ II -X
X-{OCH2CH2)p(O-C-R C -OR )u(O-~-R OC-O)(CH2CH20-)n in which each X can be a suitable capping group, with each X typically being selected from the group consisting of I-I, and alkyl or acyl groups containing from about 1 to about 4 carbon atoms. p is selected for water solubility and generally is from about 6 to about I 13, preferably from about 20 to about 50. a is critical to formulation in a liquid composition having a relatively high ionic strength. There should be very little material in which a is greater than 10. Furthermore, there should be at least 20%, preferably at least 40%. of material in which a ranges from about 3 to about S.
The RI4 moieties are essentially 1,4-phenylene moieties. As used herein, the term "the RI4 moieties are essentially 1,4-phenylene moieties" refers to compounds where the R14 moieties consist entirely of 1,4-phenylene moieties, or are partially substituted with other arylene or alkarylene moieties, alkylene moieties, alkenylene moieties, or mixtures thereof. Arylene and alkarylene moieties which can be partially substituted for 1,4-phenylene include 1,3-phenylene, 1,2-phenylene, 1,8-naphthylene, I,4-naphthylene, 2,2-biphenylene, 4,4-biphenylene, and mixtures thereof.
Alkylene and alkenylene moieties which can be partially substituted include 1,2-propylene, 1,4-butylene, 1,5-pentylene, 1,6-hexamethylene, 1,7-heptamethylene, 1,8-octamethylene, 1,4-cyclohexylene, and mixtures thereof.
For the R14 moieties, the degree of partial substitution with moieties other than 1,4-phenylene should be such that the soil release properties of the compound are not adversely affected to any great extent. Generally the degree of partial substitution which can be tolerated will depend upon the backbone length of the compound, i.e., longer backbones can have greater partial substitution for 1,4-phenylene moieties.
Usually, compounds where the R14 comprise from about 50% to about 100% 1,4-phenylene moieties (from 0% to about SO% moieties other than 1,4-phenylene) have adequate soil release activity. For example, polyesters made according to the present invention with a 40:60 mole ratio of isophthalic (1,3-phenylene) to terephthalic (1,4-phenylene} acid have adequate soil release activity. However, because most polyesters used in fiber making comprise ethylene terephthalate units, it is usually desirable to minimize the degree of partial substitution with moieties other than 1,4-phenylene for best soil release activity.
Preferably, the RI4 moieties consist entirely of (i.e., comprise 100%) I ,4-phenylene moieties, i.e., each RI4 moiety is 1,4-phenylene.

For the R15 moieties, suitable ethylene or substituted ethylene moieties include ethylene, 1,2-propylene, 1,2-butylene, 1,2-hexylene, 3-methoxy-1,2-propylene, and mixtures thereof. Preferably, the R15 moieties are essentially ethylene moieties, 1,2-propylene moieties, or mixtures thereof. Inclusion of a greater percentage of ethylene moieties tends to improve the soil release activity of compounds.
Surprisingly, inclusion of a greater percentage of 1,2-propylene moieties tends to improve the water solubility of compounds.
Therefore, the use of 1,2-propylene moieties or a similar branched equivalent is desirable for incorporation of any substantial part of the soil release component in the liquid fabric softener compositions. Preferably, from about 75% to about 100%, are 1,2-propylene moieties.
The value for each p is at least about 6, and preferably is at least about 10.
The value for each n usually ranges from about 12 to about 113. Typically the value for each p is in the range of from about 12 to about 43.
A more complete disclosure of soil release agents is contained in U.S. Pat.
Nos.:
4,661,267, Decker, Konig, Straathof, and Gosselink, issued Apr. 28, 1987;
4,711,730, Gosselink and Diehl, issued Dec. 8, 1987; 4,749,596, Evans, Huntington, Stewart, Wolf, and Zimmerer, issued June 7, 1988; 4,818,569, Trinh, Gosselink, and Rattinger, issued April 4, 1989; 4,877,896, Maldonado, Trinh, and Gosselink, issued Oct. 31, 1989;
4,956,447, Gosselink et al., issued Sept. 11, 1990; and 4,976,879, Maldonado, Trinh, and Gosselink, issued Dec. 11, 1990, all of said patents being incorporated herein by reference.
These soil release agents can also act as scum dispersants.
6. Scum Dispersant In the present invention, the fabric softening compositions can also contain an optional scum dispersant, other than the soil release agent, and heated to a temperature at or above the melting points) of the components. Scum dispersants are desirable components of the finished fabric softening compositions herein.
The' preferred scum dispersants herein are formed by highly ethoxylating hydrophobic materials. The hydrophobic material can be a fatty alcohol, fatty acid, fatty amine, fatty acid amide, amine oxide, quaternary ammonium compound, or the hydrophobic moieties used to form soil release polymers. The preferred scum dispersants are highly ethoxyiated, e.g., more than about 17, preferably more than about 25, more preferably more than about 40, moles of ethylene oxide per molecule on the average, with the polyethylene oxide portion being from about 76% to about 97%, preferably from about 81 % to about 94%, of the total molecular weight.

The Ieve1 of scum dispersant is sufficient to keep the scum at an acceptable, preferably unnoticeable to the consumer, level under the conditions of use, but not enough to adversely affect softening. For some purposes it is desirable that the scum is nonexistent. Depending on the amount of anionic or nonionic detergent, etc., used in the wash cycle of a typical laundering process, the efficiency of the rinsing steps prior to the introduction of the dispersion compositions herein, and the water hardness, the amount of anionic or nonionic detergent surfactant and detergency builder (especially phosphates and zeolites) entrapped in the fabric (laundry) will vary. Normally, the minimum amount of scum dispersant should be used to avoid adversely affecting softening properties.
Typically scum dispersion requires at least about 2%, preferably at least about 4% (at least 6% and preferably at least 10% for maximum scum avoidance) based upon the level of softener active. However, at levels of about 10% (relative to the softener material) or more, one risks loss of softening efficacy of the product especially when the fabrics contain high proportions of nonionic surfactant which has been absorbed during the washing operation.
Preferred scum dispersants are: Brij 700~' Varonic U-250~; Genapol T-500~, Genapol T-800~; Plurafac A-79~; and Neodol 2S-SO~.
7. Bactericides Examples of bactericides used in the fabric softening compositions of this invention include glutaraldehyde, formaldehyde, ?-bromo-2-nitro-propane-1,3-diol sold by Inolex Chemicals. located in Philadelphia, Pennsylvania, under the trade name Bronopol~. and a mixture of S-chloro-2-methyl-4-isothiazoline-3-one and 2-methyl-4-isothiazoline-3-one sold by Rohm and Haas Company under the trade name Kathon CG/ICP~. Typical levels of bactericides used in the present dispersion compositions arc from about 1 to about 1,000 ppm by weight of the agent.
8. Chelatin~ Agents The finished dispersion compositions and processes herein can optionally employ one or more copper and/or nickel chelating agents ("cheiators"). Such water-soluble chelating agents can be selected from the group consisting of amino carboxylates, amino phosphonates, polyfunctionally-substituted aromatic chelating agents and mixtures thereof, all as hereinafter defined. The whiteness and/or brightness of fabrics are substantially improved or restored by such chelating agents and the stability of the materials in the dispersion compositions are improved.
Amino carboxylates useful as chelating agents herein include ethylenediaminetetraacetates (EDTA), N-hydroxyethylethylenediaminetriacetates, nitrilotriacetates (NTA), ethylenediamine tetraproprionates, ethylenediamine-N,N'-wo 9sis~m pcTnB9sioosss diglutamates, 2-hyroxypropylenediamine-N,N'-disuccinates, triethylenetetraaminehexacetates, diethylenetriaminepentaacetates (DETPA), and ethanoldiglycines, including their water-soluble salts such as the alkali metal, ammonium, and substituted ammonium salts thereof and mixtures thereof.
Amino phosphonates are also suitable for use as chelating agents in the dispersion compositions of the invention when at least low levels of total phosphorus are permitted in detergent dispersion compositions, and include ethylenediaminetetrakis (methylenephosphonates), diethylenetriamine-N,N,N',N",N"-pentakis(methane phosphonate) (DETMP) and 1-hydroxyethane-1.1-diphosphonate (HEDP). Preferably, these amino phosphonates to not contain alkyl or alkenyl groups with more than about 6 carbon atoms.
The chelating agents are typically used in the present rinse process at levels from about 2 ppm to about 25 ppm, for periods fiom i minute up to several hours' soaking.
The preferred EDDS chelator used herein (also known as ethylenediamine-N,N'-disuccinate) is the material described in U.S. Patent 4,704,233, cited hereinabove, and has the formula (shown in free acid form):
H-N -C H~-C H2-N -H

COOH COOH COOH COOH
As disclosed in the patent, EDDS can be prepared using malefic anhydride and ethylenediamine. The preferred biodegradable [S,S] isomer of EDDS can be prepared by reacting L-aspartic acid with 1.2-dibromoethane. The EDDS has advantages over other chelators in that it is effective for chelating both copper and nickel rations, is available in a biodegradable form, and does not contain phosphorus. The EDDS employed herein as a chelator is typically in its salt form, i.e., wherein one or more of the four acidic hydrogens are replaced by a water-soluble ration M, such as sodium, potassium, ammonium, triethanolammonium, and the like. As noted before, the EDDS chelator is also typically used in the present rinse process at levels from about .2 ppm to about 25 ppm for periods from 1 minute up to several hours' soaking. At certain pH's the EDDS is preferably used in combination with zinc rations.
As can be seen from the foregoing, a wide variety of chelators can be used herein.
Indeed, simple polycarboxylates such as citrate, oxydisuccinate, and the like, can also be used, although such chelators are not as effective as the amino carboxylates and phosphonates, on a weight basis. Accordingly, usage levels may be adjusted to take into account differing degrees of chelating effectiveness. The chelators herein will preferably have a stability constant (of the fully ionized chelator) for copper ions of at least about 5, preferably at least about 7. Typically, the chelators will comprise from about 0.5% to about 10%, more preferably from about 0.75% to about 5%, by weight of the dispersion compositions herein. Preferred chelators include DETMP, DETPA, NTA, EDDS and mixtures thereof.
9 Optional Viscosity/Dispersibility Modifiers Relatively concentrated fabric softening compositions containing the unsaturated diester quaternary ammonium compounds herein can be prepared that are stable without the addition of concentration aids. However, the fabric softening compositions of the present invention may require organic and/or inorganic concentration aids to go to even higher concentrations and/or to meet higher stability standards depending on the other ingredients. These concentration aids which typically can be viscosity modifiers may be needed, or preferred, for ensuring stability under extreme conditions when particular softener active levels are used. The surfactant concentration aids are typically selected from the group consisting of (1) single long chain alkyl cationic surfactants;
{2) nonionic surfactants; (3) amine oxides; (4) fatty acids; and (5) mixtures thereof.
These aids are described in P&G Copending Application Serial No. 081461,207, filed June 5, 1995, Wahl et al., specifically on page 14, line 12 to page 20, line 12, which is herein incorporated by reference.

10. Chlorine Scaven~~l.,ers Chlorine is used in many parts of the world to sanitize water. To ensure that the water is safe, a small residual amount, typically about 1 to 2 parts per million (ppm), of chlorine is left in the water. At least about 10% of U.S. households has about 2 ppm or more of chlorine in its tap water at some time. It has been found that this small amount of chlorine in the tap water can also contribute to fading or color changes of some fabric dyes. Thus, chlorine-induced fading of fabric colors over time can result from the presence of residual chlorine in the rinse water. Accordingly, in addition to the chelator, the present invention preferably also employs a chlorine scavenger. Moreover, the use of such chlorine scavengers provides a secondary benefit due to their ability to eliminate or reduce the chlorine odor on fabrics.
Chlorine scavengers are materials that react with chlorine, or with chlorine-generating materials, such as hypochlorite, to eliminate or reduce the bleaching activity of the chlorine materials. For color fidelity purposes, it is generally suitable to incorporate enough chlorine scavenger to neutralize about l-10 ppm chlorine in rinse water, typically to neutralize at least about 1 ppm in rinse water. For the additional elimination or reduction of fabric chlorine odor resulting from the use of a chlorine bleach in the wash, the compositions should contain enough chlorine scavenger to neutralize at least about 10 ppm in rinse water.
Such compositions according to the present invention provide about 0.1 ppm to about 40 ppm, preferably from about 0.2 ppm to about 20 ppm, and more preferably from about 0.3 ppm to about 10 ppm of chlorine scavenger to an average rinse bath.
Suitable levels of chlorine scavengers in the compositions of the present invention range from about 0.01% to about 10%, preferably from about 0.02% to about 5%, most preferably from about 0.03% to about 4%, by weight of total composition. If both the cation and the anion of the scavenger react with chlorine, which is desirable, the level may be adjusted to react with an equivalent amount of available chlorine.
Non-limiting examples of chlorine scavengers include primary and secondary amines, including primary and secondary fatty amines; ammonium salts, e.g., chloride, sulfate; amine-functional polymers; amino acid homopolymers with amino groups and their salts, such as polyarginine, polylysine, polyhistidine; amino acid copolymers with amino groups and their salts; amino acids and their salts, preferably those having more than one amino group per molecule, such as arginine, histidine, not including lysine reducing anions such as sulfite, bisulfate, thiosulfate, nitrite; antioxidants such as ascorbate, carbamate, phenols; and mixtures thereof. Ammonium chloride is a preferred inexpensive chlorine scavenger for use herein.
Other useful chlorine scavengers include water-soluble, low molecular weight primary and secondary amines of low volatility, e.g., monoethanolamine, diethanolamine, tris(hydroxymethyl)aminomethane, hexamethylenetetramine.
Suitable amine-functional chlorine scavenger polymers include: water-soluble polyethyleneimines, polyamines, polyvinylamines, polyamineamides and poiyacrylamides. The preferred polymers are polyethyleneimines, the polyamines, and polyamineamides. Preferred poiyethyleneimines have a molecular weight of less than about 2000, more preferably from about 200 to about 1500.

11. Dye Transfer Inhibitors The compositions of the present invention may also include one or more materials effective for inhibiting the transfer of dyes from one fabric to another during the rinsing process. Generally, such dye transfer inhibiting agents include polyvinyl pyrrolidone polymers, polyamine N-oxide polymers, copolymers of N-vinylpyrroiidone and N-vinylimidazole, manganese phthalocyanine, peroxidases, and mixtures thereof.
If used, these agents typically comprise from about 0.01% to about 10% by weight of the composition, preferably from about 0.01 % to about 5%, and more preferably from about 0.05% to about 2%.
More specifically, the polyamine N-oxide polymers preferred for use herein contain units having the following structural formula: R-Ax-Z; wherein Z is a polymerizable unit to which an N-O group can be attached or the N-O group can form part of the polymerizable unit or the N-O group can be attached to both units;
A is one of the following structures: -NC(O)-, -C(O)O-, -S-, -O-, -N=; x is 0 or 1; and R
is aliphatic, ethoxylated aliphatics, aromatics, heterocyclic or alicyclic groups or any combination thereof to which the nitrogen of the N-O group can be attached or the N-O
group is part of these groups. Preferred polyamine N-oxides are those wherein R is a heterocyclic group such as pyridine, pyrrole, imidazole, pyrrolidine, piperidine and derivatives thereo f.
The N-O group can be represented by the following general structures:
O O
I I
~R~)x- i WR2)y; =NWRt)x ~R3)z wherein R1, R~, R3 are aliphatic, aromatic, heterocyclic or alicyclic groups or combinations thereof; x, y and z are 0 or 1; and the nitrogen of the N-O group can be attached or form part of any of the aforementioned groups. The amine oxide unit of the polyamine N-oxides has a pKa <10, preferably pKa <7, more preferred pKa <6.
Any polymer backbone can be used as long as the amine oxide polymer formed is water-soluble and has dye transfer inhibiting properties. Examples of suitable polymeric backbones are polyvinyls, polyalkylenes, polyesters, polyethers, polyamide.
polyimides, polyacrylates and mixtures thereof. These polymers include random or block copolymers where one monomer type is an amine N-oxide and the other monomer type is an N-oxide.
The amine N-oxide polymers typically have a ratio of amine to the amine N-oxide of 10:1 to 1:1,000,000. However, the number of amine oxide groups present in the polyamine oxide polymer can be varied by appropriate copolymerization or by an appropriate degree of N-oxidation. The polyamine oxides can be obtained in almost any degree of polymerization. Typically, the average molecular weight is within the range of 500 to 1,000,000; more preferred 1,000 to 500,000; most preferred 5,000 to 100,000.
This preferred class of materials can be referred to as "PVNO".
The most preferred polyamine N-oxide useful in the rinse added compositions and processes herein is poly(4-vinylpyridine-N-oxide) which as an average molecular weight of about 50,000 and an amine to amine N-oxide ratio of about 1:4.
Copolymers of N-vinylpyrrolidone and N-vinylimidazole polymers (referred to as a class as "PVPVI") are also preferred for use herein. Preferably the PVPVI
has an average molecular weight range from 5,000 to 1,000,000, more preferably from 5,000 to 200,000, and most preferably from 10,000 to 20,000. (The average molecular weight range is determined by light scattering as described in Barth, ei al., Chemical Analysis, Vol 113. "Modern Methods of Polymer Characterization", the disclosures of which are incorporated herein by reference.) The PVPVI copolymers typically have a molar ratio of N-vinylimidazole to N-vinylpyrrolidone from 1:1 to 0.2:1, more preferably from 0.8:1 to 0.3:1, most preferably from 0.6:1 to 0.4:1. These copolymers can be either linear or branched.
The present compositions also may employ a polyvinylpyrrolidone ("PVP") having an average molecular weight of from about 5,000 to about 400,000, preferably from about 5,000 to about 200,000, and more preferably from about 5,000 to about 50,000. PVP's are known to persons skilled in the detergent field; see, for example, EP-A-262,897 and EP-A-256,696, incorporated herein by reference. Compositions containing PVP can also contain polyethylene glycol ("PEG") having an average molecular weight from about 500 to about 100,000, preferably from about 1,000 to about 10,000. Preferably, the ratio of PEG to PVP on a ppm basis delivered in wash solutions is from about 2:1 to about 50:1, and more preferably from about 3:1 to about 10:1.
The compositions herein may also optionally contain from about 0.005% to 5%
by weight of certain types of hydrophilic optical brighteners which also provide a dye transfer inhibition action. If used, the compositions herein will preferably comprise from about 0.001 % to 1 % by weight of such optical brighteners.
The hydrophilic optical brighteners useful in the present invention are those having the structural formula:

R~ Rz ~N H H . N
N ~~--N ~ C C ~ N--~O N
~N H H N
R., S03M S03M R~
wherein R1 is selected from anilino, N-2-bis-hydroxyethyl and NI-I-2-hydroxyethyl; R2 is selected from N-2-bis-hydroxyethyl, N-2-hydroxyethyl-N-methylamino, morphilino, chloro and amino; and M is a salt-forming canon such as sodium or potassium.
When in the above formula, Rl is anilino, R~ is N-2-bis-hydroxyethyl and M is a cation such as sodium, the brightener is 4.4',-bis[(4-anilino-6-(N-2-bis-hydroxyethyl)-s-triazine-2-yl)amino]-2 2'-stilbenedisulfonic acid and disodium salt. This particular brightener species is commercially marketed under the tradename Tinopal-LJNPA-GX by Ciba-Geigy Corporation. Tinopal-UNPA-GX is the preferred hydrophilic optical brightener useful in the rinse added compositions herein.
When in the above formula, RI is anilino, R2 is N-2-hydroxyethyl-N-2-methylamino and M is a cation such as sodium, the brightener is 4,4'-bis[(4-anilino-6-(N-2-hydroxyethyl-N-methylamino)-s-triazine-2-yl)amino]2,?'-stilbenedisulfonic acid disodium salt. This particular brightener species is commercially marketed under the tradename Tinopal SBM-GX by Ciba-Geigy Corporation.
When in the above formula, R1 is anilino, R~ is morphilino and M is a cation such as sodium, the brightener is 4,4'-bis[(4-anilino-6-morphilino-s-triazine-yl)amino]2,2'-stilbenedisulfonic acid, sodium salt. This particular brightener species is commercially marketed under the tradename Tinopal AMS-GX by Ciba Geigy Corporation.
The specific optical brightener species selected for use in the present invention provide especially effective dye transfer inhibition performance benefits when used in combination with the selected polymeric dye transfer inhibiting agents hereinbefore described. The combination of such selected polymeric materials (e.g., PVNO
and/or PVPVI) with such selected optical brighteners (e.g., Tinopal L1NPA-GX, Tinopal SBM-GX and/or Tinopal AMS-GX) provides significantly better dye transfer inhibition in aqueous solutions than does either of these two components when used alone.
Without being bound by theory, it is believed that such brighteners work this way because they have high affinity for fabrics in the aqueous solution and therefore deposit relatively quick on fabrics. The extent to which brighteners deposit on fabrics in solution can be defined by a parameter called the "exhaustion coefficient". The exhaustion coefficient is in general as the ratio of a) the brightener material deposited on fabric to b) the initial brightener concentration in the wash liquor. Brighteners with relatively high exhaustion coefficients are the most suitable for inhibiting dye transfer in the context of the present invention.
Of course, it will be appreciated that other, conventional optical brightener types of compounds can optionally also be used in the present compositions to provide conventional fabric "brightness" benefits, rather than a true dye transfer inhibiting effect.

12. Other Optional Ingredients The finished dispersion compositions of the present invention can include optional components conventionally used in textile treatment dispersion compositions, for example: colorants; preservatives; surfactants; anti-shrinkage agents;
fabric crisping agents; spotting agents; germicides; fungicides; anti-oxidants such as butylated hydroxy toluene, anti-corrosion agents. and the like.
Particularly preferred ingredients include water soluble calcium and/or magnesium compounds, which provide additional stability. The chloride salts are preferred, but acetate, nitrate, etc. salts can be used. The level of said calcium and/or magnesium salts is from 0% to about 2%, preferably from about 0.05% to about 0.5%, more preferably from about 0.1 % to about 0.25%. These materials are desirably added to the water and/or acid (water seat) used to prepare the finished dispersion compositions to help adjust the finished viscosity.
The present invention can also include other compatible ingredients, including those as disclosed in copending applications Serial Nos.: 08/372,068, filed January 12, 1995, Rusche, et al.; 08/372,490, filed January 12, 1995, Shaw, et al.; and 08/277,558, filed July 19, 1994, Hartman, et al., incorporated herein by reference.
The following examples illustrate the processes and resulting compositions of the present invention, but are not intended to be limiting thereof. All parts, percentages, proportions, and ratios herein are by weight unless otherwise specified and all numerical values are approximations based upon normal confidence limits.

About 25 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are placed in a 100 mL beaker set up on a hot plate with a magnetic stirrer. The 2,2,4-trimethyl-1,3-pentanediol is heated to about 65°C and, once it becomes liquid, it is stirred using a magnetic stir bar. About 0.25 g of sodium borohydride powder is then gradually added to the beaker over an approximate 10 minute period. The sodium borohydride dissolves within about 5 minutes. Stirring is continued for an additional hour before allowing the treated 2,2,4-trimethyl-1,3-pentanediol to cool to room temperature. The resulting 2,2,4-trimethyl-1,3-pentanediol has a low, unobjectionable odor.

About 150 grams of melted (liquid) commercially available 2,2,4-trimethyl-1,3-pentanediol are placed in a 300 mL Parr autoclave fitted with a mechanical stirrer, external electric heater, thermocouple, pressure gauge and hydrogen supply line. About 0.75 grams of 10% palladium-on-carbon catalyst is added to the liquid 2,2,4-trimethyl-1,3-pentanediol. The autoclave is sealed and stirring is initiated. The autoclave is then thoroughly purged with hydrogen. About 200 psig hydrogen pressure is then applied to the autoclave. The contents of the autoclave are then heated to about 65°C. The hydrogen pressure is then adjusted and held at about 300 prig for six hours.
After approximately six hours, the autoclave is cooled and vented. The palladium-on-carbon catalyst is then immediately filtered from the liquid 2,2,4-trimethyl-1,3-pentanediol. The resulting 2,2,4-trimethyl-I.3-pentanediol has low, unoffensive odor.

About 150 grams of melted (liquid) commercially available 2,2,4-trimethyl-1,3-pentanediol is placed in a 300 mL Pan autoclave fitted with a mechanical stirrer, external electric heater, thermocouple, pressure gauge and hydrogen supply line. About 0.08 grams of Raney nickel catalyst is added to the liquid 2,2,4-trimethyl-1,3-pentanediol.
The autoclave is sealed and stirring is initiated. The autoclave is then thoroughly purged with hydrogen. About 200 psig hydrogen pressure is then applied to the autoclave. The contents of the autoclave are then heated to about 65°C. The hydrogen pressure is then adjusted and held at about 300 psig for six hours. After approximately six hours, the autoclave is cooled and vented. The Raney nickel catalyst is then immediately filtered from the liquid 2,2,4-trimethyl-1,3-pentanediol. The resulting 2,2,4-trimethyl-1,3-pentanediol has low, unoffensive odor.

About 41.25 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are placed in a 400 mL beaker. About 100 mL of water are added to the beaker, and the contents of the beaker are heated on a steam bath until the 2,2,4-trimethyl-1,3-pentanedio'I is dissolved and a solution is formed. The solution is stirred vigorously to form a cloudy solution, which eventually separates into 2 layers, the top layer being 2,2,4-trimethyl-1,3-pentanediol and the bottom Layer being water. The top layer is decanted into about 50 mL of hexane to form a new solution. About 23 grams of activated charcoal are added to the new solution while the solution is still hot. The solution is then filtered while still hot using Whatman 40 paper. The filtered solution is then allowed to cool to room temperature. The filtered solution is then further cooled to a few degrees below room temperature by placing it in a refrigerator.
Approximately 20 minutes after large crystals are formed, the hexane is decanted off the crystals into a second 400 mL beaker. The crystals are then rinsed with a few mLs of hexane and added to the second beaker. After approximately 20 minutes, more crystals are formed in the second beaker. The hexane is decanted off those crystals into a third beaker.
The crystals in the first two beakers are then dissolved in about 50 mL of hexane by heating, and allowed to cool to room temperature to form crystals. The hexane is decanted from the resulting crystals. The residual hexane is then removed by freeze drying.
The resulting 2,2,4-trimethyl-1,3-pentanediol has low, unobjectionable odor.

About 2500 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are placed in a 5 liter, 3-neck flask fitted with a heating mantle, thermometer, 5 sieve tray distillation column and hot water condenser. A few boiling stones are added to the flask.
A vacuum is then applied to reduce the pressure in the flask to about 0.5 mmHg. The contents of the flask are then heated using the heating mantle. The first condensate is observed when the pot temperature reaches approximately 102°C, with a vapor temperature of about 81 °C. Approximately 450 grams of distillate are initially collected, which is referred to as the light fraction. Collection of a middle fraction is initiated when the pot temperature is approximately 120°C, with a vapor temperature of about 104°C
and a pressure of about 2.4 mmHg. The collection of the middle fraction is terminated after collecting about 1560 grams of distillate. The flask is then cooled and the remaining heavy fraction is decanted. The 2,2,4-trimethyl-1,3-pentanediol middle fraction has a low, unobjectionable odor, while the odor of the light and heavy fractions are pungent.

About 200 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol is placed in a 500 mL 3-neck flask fitted with a heating mantle, reflux condenser and thermometer. The 2,2,4-trimethyl-1,3-pentanediol is then heated to approximately 90°C
to melt (liquify) the 2,2,4-trimethyl-1,3-pentanediol. A few boiling stones are added, along withrabout 3.4 grams of a 25% sodium methoxide (in methanol) solution and about 20 grams of methanol. The mixture is then heated to ~80°C in order to reflux the methanol. After an hour at reflux temperature, hydrochloric acid is added gradually to adjust the pH of the mixture to approximately 7. The neutralized mixture is then fractionally distilled according to Example 5. The distillation yields a middle fraction and a heavy fraction of 2,2,4-trimethyl-1,3-pentanediol that have low, unobjectionable odor, and a light fraction of 2,2,4-trimethyl-1,3-pentanediol that has an intense, offensive odor.

About 2500 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are fractionally distilled according to Example 5. About 20 grams of the middle distillation fraction are treated with about 0.20 grams of sodium borohydride according to Example I . The odor of the middle distillate fraction from Example 5 is further improved.

About 2500 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are fractionally distilled according to Example 5. About 150 grams of the middle distillation fraction are then catalytically hydrogenated in a 300 mL Parr autoclave according to Example 2 or 3. The odor of the middle distillate fraction from Example 5 is further improved.

About 25 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are treated with sodium borohydride according to Example I. Using a separatory funnel, a portion of the borohydride treated 2,2,4-trimethyl-1,3-pentanediol is extracted twice with an equal volume of a hot (~80°C) 0.1 N hydrochloric acid solution, then once with an equal volume of hot {~80°C) deionized water. The resulting 2,2,4-trimethyl-1,3-pentanediol contains about 11 % moisture and has improved odor versus the borohydride treated 2.2,4-trimethyl-1,3-pentanediol of Example 1.

About 2500 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol are fractionally distilled according to Example 5. About 25 grams of the middle distillation fraction are then reduced by treating it with sodium borohydride according to Example 1.
The odor of the middle distillate fraction from Example 5 is further improved.

About I50 grams of commercially available 2,2,4-trimethyl-1,3-pentanediol is hydrogenated according to Example 2 or 3. Using a separatory funnel, a portion of the hydrogenated 2,2,4-trimethyl-I,3-pentanediol is extracted 3 successive times with an equal volume of hot (~80°C) deionized water, using fresh water each time. The resulting 2,2,4-trimethyl-1,3-pentanediol contains about ll% moisture and has improved odor versus the hydrogenated 2,2,4-trimethyl-1,3-pentanediol of Example 2 or 3.

About 150 grams of melted (liquid) commercially available 2,2,4-trimethyl-1,3-pentanediol is catalytically hydrogenated according to Example 2 or 3. Using a separatory funnel, a portion of the catalytically hydrogenated 2,2,4-trimethyl-1,3-pentanediol is extracted 3 successive times with an equal volume of hot (~80°C) deionized water, using fresh water each time. The resulting 2,2,4-trimethyl-1,3-pentanediol contains about 11% moisture and has improved odor versus the catalytically hydrogenated 2,2,4-trimethyl-1,3-pentanediol of Example 2 or 3.
The following non-limiting Examples A, B, C, D and E show clear, or translucent, liquid fabric softening products with acceptable viscosity, containing the commercially available 2,2,4-trimethyl-1,3-pentanediol having improved odor according to the present invention.
EXAMPLES A. B, C, D and E
In the following fabric softening compositions, the abbreviated component identifications have the following meanings:
FSA1 : N,N-di(acyl-oxyethyl)-N,N-dimethylammonium (Fabric Softening Active) chloride, wherein the fatty acyl group is derived from canola oil FSA2 : N,N-di(acyl-oxyethyl)-N,N-(Fabric Softening Active) methylhydroxyethylammonium methyl sulfate, wherein the fatty acyl group is derived from canola oil TMPD : Commercial 2,2,4-trimethyl-1,3-pentanediol having improved odor according to the present invention CHDM : 1,4 cyclohexanedimethanol The compositions in Examples A, B, C, D and E below are made by first preparing an oil seat of fabric softener active at ambient temperature. The fabric softener active can be heated, if necessary, to melting if the softener active is not fluid at room temperature. The fabric softener active is mixed using an IKA RW 25~ mixer for about 2 to about 5 minutes at about I50 rpm. Separately, an acid/water seat is prepared by mixing the HC1 with deionized (DI) water at ambient temperature. If the fabric softener active andfor the principal solvents) are not fluid at room temperature and need to be heated, the acid/water seat should also be heated to a suitable temperature, e.g., about 100°F (about 38°C) and maintaining said temperature with a water bath. The principal solvents) (melted at suitable temperatures if their melting points are above room temperature) are added to the fabric softener premix and said premix is mixed for about 5 minutes. The acid/water seat is then added to the fabric softener premix and mixed for about 20 to about 30 minutes or until the composition is clear and homogeneous. The composition is allowed to air cool to ambient temperature.

A B C D E

FSAI 30 - - 26 34.7 Ethanol 2.6 2.2 2.5 2.3 3.1 Hexylene glycol - 2.2 2.5 2.3 3.1 1,2 Hexanediol - 12 5 - -HCl 0.02 0.02 0.02 0.02 0.03 Perfume 2.0 1.5 2.0 2.0 2.5 Dye 5 ppm 20 ppm 5 ppm 5 ppm 5 ppm Demineralized Balance Balance BalanceBalance Balance water For commercial purposes, the above compositions in Examples A, B, C, D and E
are introduced into containers, specifically bottles, and more specifically clear bottles (although translucent bottles can be used), made from polypropylene (although glass, oriented polyethylene, etc., can be substituted), the bottle having a light blue tint to compensate for any yellow color that is present, or that may develop during storage (although, for short times, and perfectly clear products, clear containers with no tint, or other tints, can be used), and having an ultraviolet light absorber in the bottle to minimize the effects of ultraviolet light on the materials inside, especially the highly unsaturated actives (the absorbers can also be on the surface). The overall effect of the clarity and the container being to demonstrate the clarity of the compositions, thus assuring the consumer of the quality of the product. The clarity and odor of the fabric softener are critical to acceptance, especially when higher levels of the fabric softener are present.
r

Claims (11)

What is claimed is:

1. A process of improving the odor of a material consisting essentially of 2,2,4-trimethyl-1,3-pentanediol and a minor amount of at least one odorant material selected from the group consisting of isobutyl aldehyde, isobutyric acid, 2,2,4-trimethyl-3-keto-pentanol, 2,2,4-trimethyl-3-keto-pentanol isobutyrate, diisopropyl ketone, 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate, and mixtures thereof, comprising treating said 2,2,4-trimethyl-1,3-pentanediol by a method selected from the group consisting of reduction, optionally with sodium borohydride; hydrogenation;
recrystallization; ion exchange treatment; fractional distillation; base treatment; aqueous extraction; vacuum stripping; nitrogen sparging; and combinations thereof, to reduce the gas phase concentration of at least one of said odorant materials to improve the odor of said material.

2. A process according to Claim 1, wherein said method further comprises one or more aqueous extraction steps and/or nitrogen sparging step and/or vacuum stripping step.

3. A process according to any of Claims 1-2, wherein said method comprises hydrogenating said material by treating said material with hydrogen and a hydrogenation catalyst selected from the group consisting of palladium, nickel, copper, platinum, copper chromite, and mixtures thereof.

4. A process according to any of Claims 1-3, wherein said method comprises:
(a) adding an organic solvent, optionally comprising hexane, to said material, which contains isobutyric acid, to form a liquid solution;
(b) treating said liquid solution with an ion exchange resin;
(c) crystallizing said material;
(d) extracting said material with an aqueous solution to remove said isobutyric acid;
(e) drying said material; and (f) evaporating said organic solvent.

5. A process according to any of Claims 1-4, wherein said method comprises fractionally distilling said material to form a light fraction, a middle fraction and a heavy fraction, wherein said middle fraction is optionally hydrogenated by treating said middle fraction with hydrogen and a hydrogenation catalyst selected from the group consisting of palladium, nickel, copper, platinum, copper chromite, and mixtures thereof;
and/or said middle fraction is reduced by treating said middle fraction with sodium borohydride;
and/or said middle fraction is treated by one or more aqueous extraction steps, and/or nitrogen sparging step and/or vacuum stripping step, said middle fraction having improved odor.

6. A process according to any of Claims 1-3, wherein said method comprises:
(a) adding a solution containing a base, optionally sodium methoxide and/or sodium hydroxide, and/or sodium carbonate, and a solvent, optionally methanol and/or water, to said material to form an alkaline liquid mixture;
(b) heating said alkaline liquid mixture to reflux said solvent;
(c) adding an acid, optionally hydrochloric acid, to said alkaline liquid mixture to adjust the pH of said alkaline liquid mixture to create a neutral liquid mixture;
and (d) fractionally distilling said neutral liquid mixture to form a light fraction, a middle fraction, and a heavy fraction, wherein said middle fraction and said heavy fraction have improved odor.

7. A process according to Claim 6, wherein said middle fraction is optionally hydrogenated by treating said middle fraction with hydrogen and a hydrogenation catalyst selected from the group consisting of palladium, nickel, copper, platinum, copper chromite, and mixtures thereof; and/or said middle fraction is reduced by treating said middle fraction with sodium borohydride; and/or said middle fraction is treated by one or more aqueous extraction steps, and/or nitrogen sparging step and/or vacuum stripping step, said middle fraction having improved odor.

8. A composition consisting essentially of 2,2,4-trimethyl-1,3-pentanediol, said composition containing very low, non-objectionable levels, at the conditions of use, of odorant material selected from the group consisting of isobutyl aldehyde, isobutyric acid, and mixtures thereof, optionally wherein said isobutyl aldehyde, is optionally at a gas phase concentration of less than about 15, or, optionally, less than about 8, or, optionally, less than about 1, micrograms per liter; and said isobutyric acid, is optionally at a gas phase concentration of less than about 7, optionally, less than about 1, micrograms per liter; said composition also optionally containing one, or more of: 22,4-trimethyl-3-keto-pentanol;
2,2,4-trimethyl-3-keto-pentanol isobutyrate; di-isopropyl ketone; 2,2,4-trimethyl-1,3-pentanediol mono-isobutyrate; and mixtures thereof, said composition optionally being obtained in accordance with any of the processes of Claims 1-7.

9. A composition according to Claim 8, wherein the gas phase concentration of each of the following odorant materials is as follows: isobutyl aldehyde should be less than about 15, optionally 11, 8, or 1, micrograms per liter; isobutyric acid should be less than about 7, optionally 4 or 1, micrograms per titer; 2,2,4-trimethyl-3-keto-pentanol should be less than about 19, optionally 9 or 1, micrograms per Liter; 2,2,4-trimethyl-3-keto-pentanol isobutyrate should be less than about 2, optionally 1.5 orl, micrograms per liter;
diisopropyl ketone should be less than about 3, optionally 2 or 1, micrograms per liter;
and/or 2,2,4-trimethyl-1,3-pentanediol monoisobutyrate should be less than about 3, optionally 2 orl, micrograms per liter.

10. Clear concentrated fabric softening compositions comprising:
(a) from about 2% to about 40%, optionally from about 5% to about 40%, or from about 7% to about 35%, or from about 10% to about 25%, by weight of the fabric softening composition, of the composition of Claim 8 or 9;
(b) from about 2% to about 75%, optionally from about 8% to about 70%, or from about 13% to about 65%, or from about 18% to about 40%, by weight of the fabric softening composition, of fabric softening active; and (c) water, optionally from about 3% to about 95%, or from about 10% to about 80%, or from about 30% to about 70%, by weight of the fabric softening composition.

11. The composition of Claim 10, further comprising:
(a) an effective amount, sufficient to improve clarity, of auxiliary solvent selected from the group consisting of 1,4-cyclohexanedimethanol, 2-ethyl-1,3-hexanediol, low molecular weight water soluble solvent, and mixtures thereof, said auxiliary solvent being at a level that will not form clear compositions when used alone;
(b) optionally from about 0.1 % to about 8% of a perfume;
(c) optionally from about 0.01 % to about 0.2% of stabilizer; and (d) optionally an effective amount to improve clarity, of water soluble calcium and/or magnesium salt.