GB2260997A

GB2260997A - Fabric softener

Info

Publication number: GB2260997A
Application number: GB9222697A
Authority: GB
Inventors: Peter J Frank; Dale F Shumway; David E Whittlinger
Original assignee: Sherex Chemical Co Inc
Current assignee: Witco Corp
Priority date: 1991-11-01
Filing date: 1992-10-29
Publication date: 1993-05-05
Also published as: JPH05263365A; DE4236770A1; GB9222697D0; AU2745592A; SE9203211D0; SE9203211L

Abstract

A fabric softener composition comprises a mixture of a quaternary ammonium compound, fatty acid, tertiary amine salt and nonionic release aid which is easy to handle and does not form a skin or thick foam at the softener-air interface. It is used as a dryer additive softener when coated onto suitable substrates such as polyester, rayon or foam.

Description

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1 FABRIC SOFTENER WITH FATTY ACID AND RELEASE AGENT The present invention relates to a method for providing multicomponent high solid fabric dryer softeners which are easy to handle and do not form a skin or thick foam at the softener-air interface. A preferred aspect of the 5present invention relates to the quaternization of tertiary amines in the presence of a fatty acid and a non-acid release aid to produce multicomponent fabric softeners with improved handling and coating properties for use in laundry dryers.

It is well known in the art to treat textile 10fabrics, particularly after washing, with fabric softening agents in order to remove the stiffness and static charges of the material. The use of softening agents generally improves the feel of the fabrics and, in case of clothes, improves the comfort in wear. In addition, laundered textile fabrics tend 15to retain wrinkles and attract both dirt and dust. These undesirable consequences of laundering have been overcome by employing quaternary ammonium compounds, which are used to impart softness and pliability to the fabrics and to diminish static charges. These quaternary ammonium compounds can be 20incorporating as components of the laundry detergent, added separately to the wash, or dispersed in the dryer.

Normally, softening agents are applied from an aqueous liquid which is prepared by adding a small volume of a fabric softening composition to a large volume of water, 25e.g. during the final rinse cycle. The softening composition is usually an aqueous liquid product containing from about 3% to about 10% by weight of the quaternary ammonium compound. Such compositions are generally prepared by dispersing in water a cationic material, which contains short chain 30alkenols as a solvent. Flammable solvents like isopropyl 1 alcohol (IPA) are generally used however mixtures of IPA and water and water alone can also be employed. These solvents have to be removed in many applications since the desired end product is often used in a solventless or solid form. For a 5number of reasons, including transportation and packing cost, the use of adding an aqueous dispersion of softening agents to textile fabrics during the rinse cycle is undesirable.

The problems associated with bulky liquid fabric softening compositions may be overcome by incorporating the loquaternary ammonium compounds, either as a solution or dispersion, onto a substrate such as a non-woven fabric, sponge, absorbing paper, or a polymeric foam such as polyurethane foam. Thus, a dry substrate impregnated with the fabric softening agent can be directly added to the 151aundry dryer while the fabric or clothes are still damp. The quaternary ammonium compound is formulated usually with a fatty acid ester which promotes the transfer of the softening agent from the non- woven or porous polymeric substrate to the fabric or clothes. However, this process requires that the 20fatty acid ester be separately blended into the quaternary ammonium compound. This blend usually consists of about 70% of dihydrogenated tallow dimethyl dmmonium and about 30% of a fatty acid ester. This process involves the extra manufacturing steps of transportation, handling and blending.

If these steps could be eliminated, a cost savings could be realized.

Finally, quaternary ammonium compounds are now directly added to both solid and liquid laundry detergent compositions. The advantage of this application is that the quaternary ammonium compound can be incorporated as a fabric softener during the entire wash cycle of the materials. The lmost widely used and successful quaternary ammonium compounds used in this application are the dimethyl (dihydrogenated tallow) ammonium chlorides or methyl sulfates.

Quaternary ammonium compounds are also used to 5manufacture organomodified clays which may be added to drilling muds utilized in drilling oil wells, the organomodified clay providing improved lubrication and rheological properties of the drilling muds. These organoclays are also employed as thixotropic agents in loplastisols, organosols, paints and other protective coatings, grease additives, foundry additives, cosmetics, resins and printing inks. The most common quaternary ammonium compounds employed in this regard are methyldi(hydrogenated tallow) benzylammonium chloride, dimethyldi(hydrogenated tallow) l5ammonium chloride and dimethyl(hydrogenated tallow) benzylammonium chloride.

Quaternary ammonium compounds are also employed as bactericides the most common of which is the quaternary ammonium compound of benzy1chloride and a dimethylalkylamine, 20the alkyl group having from about 12 to about 16 carbon atoms as well as trimethyl alkyl ammonium chlorides where the alkyl group is a long chain alkyl such as an octadecyl group. Additionally, dimethyldicoconut- oil fatty ammonium chlorides are also effective disinfectants, e.g. bactericides or 25bacteristats especially against anaerobic bacteria which are sulfate reducers that are found in oil wells, these bacteria causing severe corrosion problems and plugging of formations which this type of quaternary ammonium compound can minimize or eliminate. Additionally, these quaternary ammonium compounds effective against anaerobic bacteria are also effective in removing oil from sandstone formations in oil 1wells and provide a two-fold effect of functioning not only as a bactericide but also in promoting so-called secondary recovery of oil.

An additional use of quaternary compounds is in 5hair treatment because of the antistatic effects obtained with such compounds, as well as the increased wetting which promotes improvements in both wet and dry combing or brusfiing and improves luster and feel. The most commonly used quaternary ammonium compounds in this respect are 10trimethylalkylammonium chloride, pentaethoxystearylammonium chloride, dimethylstearylbenzylammonium chloride and dimethy1dialkylammonium chlorides.

The present invention utilizes a fatty acid in combination with fatty esters, fatty alcohols, fatty 15ethoxylated or propoxylated alcohols or fatty triglycerides to produce a laundry dryer softener which does not form a skin or foamy layer at the softener-air interface. More specifically, the present invention relates to the quaternization of tertiary amines in the presence of a fatty 20acid and a nonionic release acid to produce a multicomponent softening agent.

The present invention eliminates problems which are usually associated with prior art dryer softeners including: excessive foaming in formation and shipment of the product, and foamy conditions exhibited when coating the softener onto fabric substrate such as rayon, polyesters, or foam sheets. The present process also allows for faster coating conditions and less waste due to foam build up on the rollers. The present invention also produces softeners which have lower viscosities, and can be formulated and applied to substrates at lower temperatures, compared to prior art softeners containing quaternary ammonium and PEG esters.

Another advantage of the present invention is that it reduces the operating cost since lower energy requirements are needed for storage and coating than prior art dryer softeners.

The present invention relates to a composition of matter comprising a mixture of (a) a quaternary ammonium compound having the formula:

(I) (II) R 1 R7 R - Ne Ae 1 R2 or N Ae R!' 0 R' R' - NH - C - R -5 where R, R-'. and R2 are (1) linear or branched chain aliphatic saturated or unsaturated hydrocarbon -groups having up to 22 carbon atoms; or amino group; (2) a hydroxy lower alkyl or amino lower alkyl (3) an alkyl amido alkylene group of the formula, 0 11 R 3 - C - NH - R' where R4 is lower alkylene and R3 is any of R, W- or R2; (4) a lower alkoxy group; (5) a poly(oxyloweralkylene) group; so that at least one of R, RL or R 2 is one of said hydrocarbon groups or one of said hydroxy lower alkyl groups where R5 is a linear or branched chain aliphatic saturated or unsaturated hydrocarbon group having up to 22 carbon atoms and R6 is a lower alkylene group, where R7 is a lower alkyl g:Foup or cyclo lower alkyl group such as benzyl, cyclohexylmethyl, tolyl, xylyl, naphthylmethyl, '- where A- is an anion; (b) a linear or branched chain saturated or unsaturated fatty acid having from about 12 to about 22 carbon atoms; (c) a tertiary amine salt having formula (I) or (II) where R7 is hydrogen; and (d) a nonionic component selected from the group consisting of (i) fatty acid esters having the formula:

0 11 RS - C 0 - R where R"' is a linear or branched chain, aliphatic saturated or unsaturated group having from about 11 to about 21 carbon atoms; where R" is C:,. to C., alkyl, -(CH2CH20),,H, or (C:3H,sO).H where n is 1 to 10; (ii) fatty alcohols containing 12 to 22 carbon atoms; (iii) ethoxylated or propoxylated fatty alcohols of the formula R"k-O-(C, H40),I-H or R'K-O-(C3H.0).-H t 1wherein R". is an alkyl or alkenyl group having 12 to 22 carbon atoms and n is 1 to 10; (iv) fatty triglycerides; and mixtures of any of the foregoing.

As noted, the present invention concerns a method for producing a multicomponent high solid fabric softener composition comprising a quaternary ammonium compound, a fatty acid, a tertiary amine salt and a nonionic release aid agent.

In its broadest aspect, the invention is directed to a method of producing a fabric softener composition containing a quaternary ammonium compound, a fatty acid, a tertiary amine salt and a nonionic release aid by reacting a tertiary amine, a quaternizing agent, a fatty acid and one of 15the nonionic compounds, in amount so that said mixture will contain at least a quaternary ammonium component, a fatty acid, a tertiary amine salt and a nonionic agent.

The tertiary amine used in this invention has the following formula:

Rn- 1 R - N 1 R 2 wherein R, R', R' can be any one of the following combinations:

(1) a linear or branched chaill aliphatic saturated or unsaturated hydrocarbon group containing C-L-C22 atoms; (2) a lower hydroxy alkyl or amino lower alkyl or amino group; tl.

1 (3) an alkyl amido alkylene group of the formula:

0 11 R' - C - NH - R' wherein R 4 is lower alkylene and R3 is any 2 of R, R ' or R; (4) a lower alkoxy group; (5) a poly(oxyloweralkylene) group; so that at least one of R, R' or R 2 is one of said 101inear or branched chain aliphatic saturated hydrocarbon groups or one of said hydroxy lower alkyl groups; or said tertiary amine is an imidazoline of the formula:

N R' - N- 0 1 11 R' - NH - C -R' where R5 is a linear or branched chain, aliphatic saturated or unsaturated hydrocarbon group having from C,.-C,., atoms and R' is a lower alkylene group; said quaternizing agent being known in the art and which will produce a quaternary ammonium compound having an 25anion A-. Generally these quaternizing agents are those having the formula.R7(,,-,,)X; where R 7 is a lower alkyl group or cyclo lower alkyl group such as benzyl, cyclohexylmethyl,, tolyl, xylyl, naphthylmethyl, and X may be a chlorine, iodine, bromine, 30sulfate, methyl sulfate, carbonate, phosphate, borate, formate, acetate, propionate, adipate, benzoate group and the like where (a) is equal to the valence of X and (b) is from 1 to the valence of X; A 1 said fatty acid is a linear or branched chain, aliphatic saturated or unsaturated fatty acid containing from about 12 to about 22 atoms, preferably based on coconut oils, vegetable oils, seed oils, animal fats or fish oils; said nonionic release aid is selected from the group consisting of fatty esters, fatty alcohols ethoxylated or propoxylated fatty alcohols and fatty triglycerides; where said fatty ester is a linear or branched chain, aliphatic saturated or unsaturated fatty acid locontaining from about 12 to about 22 atoms esterified with a C, to C,, alkyl group, or with -(CH,,CH2Q).H or -(C3H.0),H where n is 1 to 10. Some examples of fatty esters which can be used in this invention include: methyl stearate, methyl tallowate, PEG-200 monostearate, methyl palmitate, and methyl laurate or any mixtures thereof; where said fatty alcohol is a linear or branched long chain, aliphatic saturated or unsaturated fatty alcohol containing from about 12 to about 22 atoms. Various fatty alcohols employed in this regard include: stearyl alcohol, tallow alcohol, palmityl alcohol, lauryl alcohol, and coconut alcohol or any mixtures thereof; where said ethoxylated or propoxylated fatty alcohol is an ethoxylated or propoxylated derivative of a linear or branched long chain, aliphatic saturated or unsaturated fatty alcohol containing from about 12 to about 22 atoms. The ethoxylated compound has the following formula:

R aL - 0 - [C2H4OL,-H 30and the propoxylated compound has the following formula:

R^ - 0 - IC:,H,,,01,,-H wherein the R"' group is derived from an alcohol such as: stearyl alcohol, tallow alcohol, hydrogenated tallow alcohol, and lauryl alcohol; and 1 n is from 1 to 10;_ where said fatty triglyceride is a linear or branched long chain,, alipha ' tic saturgLted or unsaturated triglyceride (CH20C(O)R)-( - CHOC(O)R)-CH,OC(O)R) where R contains from about 11 -to about 21 atoms.

Various triglycerides which can be used in this regard include: hydrogenated tallow, tallow, cocinin palm oil, and hydrogenated rapeseed oil or any mixtures thereof.

Various tertiary amines that can be employed in this regard include:

- dimethylamino propyl amine, amino ethanolamin distearyl methyl amine, dihydrogenated tallow methyl amine, ditallow methyl amine, dimethyl hydrogenated tallow amine, dimethyl coco amine, distearyl ethoxyethyl amine, stearyl bis-hydroxyethyl amine, stearyl bis (polyethoxy ethanol) amine, bis (tallowamidoethyl) 2-hydroxyethyl amine, bis (tallowamidoethyl) 2-hydroxylpropyl amine, 1-hydrogenated tallow amido ethyl -2-hydrogenated tallow imidazoline tallow amido propyl-dimethyl amine hydrogenated tallow hydroxyethyl imidazoline The prior art also discloses other amines that may be used such as those described in the United States Patents to Marschner, U.S. 4,859,456; Caswell et al., U.S. 4,857,213; Demangeon, U.S. 4,851,141 and Mermelstein et al., U.S. 4,844,824 all of which are incorporated by reference (also referred to hereafter as "the prior art cited herein.")

Imidazoline compounds that may be used are also described in Demangeon (supra), whereas the quaternizing agents include; dimethyl sulfate, diethyl sulfate, methyl chloride, methyl bromide and benzyl chloride as well as those art cited herein.

c ted in the prior The quaternary ammonium compound thus obtained has the formula:

(I) (II) R 1 R - Ne - R 1 X2 or N W5 -// Ae \N- 0 --' 1. 11 R 7 R' - NH C R' where R, R2-, R2, R 3 P R4, Rs, R6 and R' have been defined above; where A- is an anion based on R7 (.,)X or equivalent anions known in the quaternary ammonium compound art.

The tertiary amine salt obtained has the formula:

(V) (VI) R' 1 R - K(D - H 1 M2 or Ae NAe R' Nfi - 0 H R' - NH - C - R In another embodiment, the tertiary amine, quaternizing agent, fatty acid, and nonionic release aid are reacted with one another each in an amount so that the multicomponent fabric softener obtained contains from about 10 to about 80 weight percent and preferably from about 35 to about 70 weight percent of said quaternary ammonium compound, about 1 to about 70 weight percent and preferably from about 5 to about 35 weight percent of said fatty acid and from about 1 to about 70 weight percent and preferably about 5 to 1 about 25 weight percent of one of the said nonionic release aid, and from about 1 to about 30 weight percent of said salt. The weight ratio of said quaternary ammonium compound to said nonionic agent is preferably from about 5:1 to about 51:3. The weight ratio of said fatty acid to said nonionic is at least 1:2, typically 1:1; however, it is preferred that the weight ratio of fatty acid to nonionic agent be about 2:1 or higher. If the multicomponent. fabric softener compositions contains too low a concentration of fatty acid lothen the nonionic agent will foam too much resulting in a material which is extremely difficult to handle. Additionally, a skin or crust will form at the softener-air interface which increases the viscosity of the material. However, if a proper balance between fatty acid and nonionic is achieved, a reduction in viscosity and little or no foaming will be observed. Thus, the multicomponent. fabric softener described in this invention results in the reduction in the difficulties of handling, transporting, and coating of the substrate, by providing lower viscosities and non-foaming 20properties exhibited by this fabric softener composition.

The present invention also relates to a mixture of the various quaternary ammonium compounds as described previously in combination with the various fatty acids and nonionic release agents also as described above and in the amounts and ratios as previously described.

The invention also relates to a fabric softening article comprising a fabric softening amount of any of the compounds previously described herein operatively associated with a substrate that will release said multicomponent fabric softener to a material or fabric under softening conditions usually encountered in automatic laundry dryers and includes the use of any of the aforesaid mixtures in a fabric softening relationship with a nonwoven or woven fiber of any form of polymeric foam substrates, such composition being prepared in a manner well taught in the art. The - 15 multicomponent fabric softener is employed in an amount of from about 0.1 to about 10 grams and especially 1 to about 4 grams per 9-inch by 11-inch (22.9 cm by 27.9 cm) dryer sheet.

The multicomponent softening agent can be used as a dryer added softener when coated onto a suitable substrate such as polyester, rayon or foam.

The presence of fatty acid need not be present during the quaternizing reaction howeverit is essential that the final composition contain said fatty acids to obtain the desired properties mentioned herein.

The composition of the invention may further be used in preparing a fabric cleaning composition, for example one that contains a detergent.

The following example is illustrative. The method of the invention as well as the mixture obtained by this method is illustrated by the following components in the indicative amounts.

1 EXAMPLE 1 ..............

.................

........

---- - -------- - .............

.....................

..................

.............

.................

.......

..............

.........

........

.................

Dihydrogenated Tallow-Methyl Amine Hydrogenated Tallow Stearic Acid Dimethyl Sulfate molecular weight = 520 56.52 15.00 15.00 1 13.48 1 The dihydrogenated tallow amine, stearic acid and hydrogenated tallow were pha:iZged to a clean, dry reactor which was heated to 140F (60 0 C). A slight nitrogen purge was employed over this mixture to prevent the amine from 5interacting with air. Dimethyl sulfate was then added in small quantities in order to control the temperature of the quter7ization reaction mixture between 150-175F (65.6-7_9.4(C). he reaction is exothermic and the end point of the reaction is indicated to some degree when an exotherm is no longer loobtained. If necessary, the % free amine of the reaction mixture can be adjusted by further addition of dimethyl sulfate until it is between 1.0- 1.5%. After completion of the reaction, the mixture was allowed to cool to ambient. Optionally, about 0.5 to 33 weight % of active NaHS03/H.0 l5solution may be added either prior to or after the quaternization reaction to help reduce and stabilize the color of the mixture.

- 18

Claims

A composition of matter comprising a mixture of (a) a quaternary ammonium compound having the f ormula:

(I) (II) R' 1 R ' Ne R 7 Ae 1 ' 1k2 or W5 Ae -\ N 1 0 1/ 1 e 11 R' R' - NH - C - R!' where R. R1 and R2 are (1) linear or branched chain aliphatic saturated or unsaturated hydrocarbon group having up to 22 carbon atoms; (2) a hydroxy lower alkyl or amino lower alkyl or amino group; (3) an alkyl amido alkylene group of the formula, 0 R3 - C - NH - R4 where R4 is lower alkylene and R3 is any of R, Rl or R2; (4) a lower alkoxy group; (5) a poly(oxyloweralkylene) group; so that at least one of R, Rl or R2 is one of said hydrocarbon groups or one of said hydroxy lower alkyl groups where R5 is a linear or branched chain aliphatic saturated or unsaturated hydrocarbon group having up to 22 carbon atoms and R6 is a lower alkylene group, where R7 is a lower alkyl group or cyclo lower alkyl group such as benzyl, cyclohexylmethyl, tolyl, xylyl, naphthylmethyl, where A- is an anion; (b) a linear or branched chain saturated or unsaturated fatty acid having from about 12 to about 22 carbon atoms; (c) a tertiary amine salt having formula (I) or (II) where R7 is hydrogen; and (d) a nonionic component selected from the group consisting of (i) fatty acid esters having the formula: 0 R8 - C - 0 - Re where R8 is a linear or branched chain, aliphatic saturated or unsaturated group having from about 11 to about 21 carbon atoms; where Re is C 1 to C12 alkyl, -(C22CH20)nH, or -(C3H60)nH where n is 1 to 10; (ii) fatty alcohols containing 12 to 22 carbon atoms; (iii) ethoxylated or propoxylated fatty alcohols of the formula Ra_O_ (C2H40)n-H or Ra-O_ (C3H60)n-H where Ra is an alkyl or alkenyl group having 12 to 22 carbon atoms and n is 1 to 10; (iv) fatty triglycerides; and mixtures of any of the foregoing.
2. The composition of claim 1 comprising 10 wt. % to about 80 wt. % of said quaternary ammonium compound, about 1 wt. % to about 30 wt. % of said salt, about 1 wt. % to about wt. % of said nonionic component, about 1 wt. % to about wt. % of said fatty acid wherein the weight ratio of said fatty acid to said nonionic component is at least about 1:2.
3. The composition of claim 1 or 2 comprising about 35 wt. % to about 70 wt. % of said quaternary ammonium compound, about 1 wt. % to about 30 wt. % of said salt, about 5 wt. % to about 25 wt. % of said nonionic component, and about 5 wt. % to about 35 wt. % of said fatty acid.
4. The mixture of any one of claims 1 to 3 wherein said quaternary ammonium compound is (I) and wherein at least one of said R, R1 and R2 groups is a branched chain or linear, aliphatic saturated or unsaturated hydrocarbon group having from about 12 to about 22 carbon atoms and the balance, if any, of said R. Rl and R2 groups is a lower alkyl group.
5. The mixture of any one of claims I to 4 wherein Ais a lower alkyl sulfate group and where R, Rl and R2 is said hydrocarbon group, and is saturated.
6. A composition of matter according to claim 1 substantially as herein described.
7. A composition of matter according to claim 1 substantially as herein described-with particular reference to Example 1.
8. A fabric softening article of manufacture comprising a fabric softening amount of the mixture of any one of claims 1 to 7, operatively associated with a substrate that will release said mixture to a fabric under fabric softening conditions.
9. The article of claim 8 where said substrate is a fabric or a porous polymeric material.
10. The composition of matter of any of claims 1 to 7 for use in preparing a fabric cleaning composition.
11. The composition of claim 10 wherein the fabr cleaning composition contains a detergent.

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