US3283005A - p-xylylene bis quaternary ammonium compounds - Google Patents

p-xylylene bis quaternary ammonium compounds Download PDF

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US3283005A
US3283005A US276157A US27615763A US3283005A US 3283005 A US3283005 A US 3283005A US 276157 A US276157 A US 276157A US 27615763 A US27615763 A US 27615763A US 3283005 A US3283005 A US 3283005A
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compounds
quaternary ammonium
chloride
xylylene bis
xylylene
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US276157A
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Phillip G Abend
Jungermann Eric
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Armour and Co
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Armour and Co
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Priority to US276157A priority Critical patent/US3283005A/en
Priority to FR8042A priority patent/FR1392948A/en
Priority to GB17532/64A priority patent/GB1018443A/en
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    • D—TEXTILES; PAPER
    • D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06M—TREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with compounds containing nitrogen
    • D06M13/46—Compounds containing quaternary nitrogen atoms
    • D06M13/467—Compounds containing quaternary nitrogen atoms derived from polyamines

Definitions

  • This invention relates to novel p-xylylene bis quaternary -ammonium compounds.
  • the compounds of this invention have particular utility as cationic fabric softena ers in industrial and household applications.
  • This invention is therefore also concerned with a method of softening fabrics wherein the compounds of this invention are applied to the fabrics.
  • Certain symmetrical diquaternary ammonium compounds have heretofore been disclosed, such as those described in United States Patent 2,933,529, issued April 19, 1960. As far as is known, however, no one heretofore has described or prepared any compounds which can be classed as p-xylylene bis quaternary ammonium compounds. This invention is therefore based in part on the discovery of such compounds, which have been found to be highly effective cationic fabric softeners.
  • cationic fabric softeners such as dimethyl di-tallow ammonium chloride
  • the fabric may be rendered anti-static, lint-free, and soft after application of the cationic agent, the fabric may tend to resist the absorption of water.
  • water absorbency is an important property, such as with diapers
  • the tendency of the cationic fabric softener to produce a water-proofing effect, and to interfere with rewetting of the fabric can be a serious problem. This problem tends to become more acute with repeated applications of the fabric softener.
  • the quantity of the softener on the fabric will tend to buildaip with each application even though there are intervening washings of the fabric, and the rewet property of the fabric can be drastically curtailed.
  • the bis quaternary ammonium compounds of this invention can be represented by the following structural formula:
  • R is an aliphatic hydrocarbon group of from 14 to 22 carbon atoms, R; and R are members of the class consisting of methyl, ethyl, hydroxyethyl and hydroxypropyl, and X is an ammonium salt anion.
  • R is a saturated alkyl group of from 16 to 18 carbon atoms, such as an octadecyl group.
  • R can be derived from a mixed fatty acid source, the mixed alkyl and 'alkylene groups of the fatty acids of tallow are particularly desirable.
  • the tallow hydrocarbon groups can be partially or completely hydrogenated to reduce the content of oleyl groups, thereby providing saturated hydrocarbon chains of from 16 to 18 carbon atoms, and predominately saturated C chains.
  • Patented Nov. 1, 1966 pounds of this invention manifest good rewet properties when employed as cationic fabric softeners. However, the rewet properties tend to be even further improved where the R and R groups are hydro-xyethyl or hydroxypropyl groups. A classof compounds wherein R and R are hydnoxyethyl groups is particularly preferred. However, superior rewet properties are also obtained when R is a methyl group.
  • the quaternary ammonium compounds of this invention are in their salt form, that is, they are associated with an ammonium salt anion.
  • an ammonium salt anion For use as cationic fabric softeners, it is desirable to have the compounds readly dissolvable or dispersible in water, and the salt form tends to accomplish this result.
  • any of the known ammonium salt anions can be used, it is preferred to employ anions which are known to promote the water solubiltiy or water dispersibility of the compounds.
  • X can be a halogen anion such as chloride, bromide, or iodine anions.
  • anions can be substituted for various purposes, such as sulfate, methylsulfate, phoshate, acetate, citrate, tartrate, and the like.
  • the compounds can be conveniently prepared, as will subsequently be described from reagents which result in X being choride or other halide anion.
  • the chloride or halide anion can be exchanged for other anions, such as :those already listed. Procedures for accomplishing such an exchange are well-known in the art, such as metathesis with the halide form or by the use of anionexchange resins.
  • p-xylylene bis dimethyloctadecylarnmonium chloride
  • p-xylylene ibis bishydroxyethyloctadecylammonium chloride
  • p-xylylene bis bishydroxyethylhexadecylammonium chloride
  • p-xylylene bis bishydroxyethyl tallow ammonium chloride
  • the compounds of this invention can be readily prepared by reacting a xylene halide, such as p-xylylene chloride or a'u'-dichloro-p-Xylene, with a tertiary amine.
  • a xylene halide such as p-xylylene chloride or a'u'-dichloro-p-Xylene
  • This reaction can be readily carried out with the reactants dissolved in an inert organic solvent such as isopropanol, ethyl or butyl acetate, dimethyl formamide, etc.
  • Two moles of the tertiary amine are reacted with each mole of the xylene halide to produce the his quaternary ammonium compound.
  • the reaction is preferably EXAMPLE 1
  • a mixture consisting of p-xylylene chloride (0.25 mole, 43.8 g.), cctadecyldimethyl amine (0.55 mole, 169 g.), 380ml. of n-propyl alcohol and 20 ml. of water was refluxed for four hours.
  • the solvent was removed by
  • the residue was crystallized from a 4:1 mixture of ethyl acetate and isopropyl alcohol.
  • the crystals were Washed with petroleum ether and air-dried. Yield of p-xylylene bis (dimethyloctadecylammonium chloride) was 196 g., 99.5% active by titration, 99% of theory.
  • EXAMPLE 2 A solution of p-xylylene chloride (0.1 mole, 17.5 g.), and octadecylbishydroxyethyl amine (0.23 mole,, 80.0 g.) in 200 ml. of N,N-dirnethyl formamide was maintained at l10l20 for three and one-half hours, cooled to room temperature and then poured into 600 ml. of acetone. The white precipitate was filtered, Washed with petroleum 3 ether and air-dried. Yield of p-xylylene bis (bishydroxyethyloctadecylammonium chloride) was 42 g., 94.5% active by titration, 46.5% of theory.
  • EXAMPLE 3 A solution of hexadecylbishydroxyethyl amine (0.4 mole, 131 g.), a'a'-dichloro-p-xylene (0.2 mole, 35.0)
  • the compounds of this invention as cationic fabric softeners, it is preferred to, incorporate them in rinse water following the washing of the fabric.
  • the softener compound can be used at a level ranging from .03 to .3% based on the weight of the fabric being treated (O.W.F). For most purposes, however, the compounds will be applied at the rate of from .065 to 0.1% (O.W.F.).
  • the cationic softeners are particularly effective with cellulosic fabrics such as cotton fabrics.
  • the softeners can be used to treat cotton diapers, cotton sheets and pillowcases, etc. Since the compounds are highly substantive to cellulosic fabrics, the treatment of such fabrics will usually remove substantially all of the softener compound from the water solution.
  • the compounds described in the foregoing examples were tested for softening activity on cotton fabrics at levels ranging from .075 to .1% (O.W.F.). They were found to be highly effective softeners. For example, p-xylylene bis (bishydroxyethyloctadecylammonium chloride) was found to be equal in softening activity at a level of 075% to Arquad 2HT at a level of 0.1% (O.W.F.).
  • Arquad 2HT is a commercial cationic softener manufactured by Armour and Company which has become accepted as one of the most effective softeners previously known. The trade name Arquad 2HT designates that the compound is di(hydrogenated tallow) dimethyl ammonium chloride.

Description

United States Patent 'ice This invention relates to novel p-xylylene bis quaternary -ammonium compounds. The compounds of this invention have particular utility as cationic fabric softena ers in industrial and household applications. This invention is therefore also concerned with a method of softening fabrics wherein the compounds of this invention are applied to the fabrics.
Certain symmetrical diquaternary ammonium compounds have heretofore been disclosed, such as those described in United States Patent 2,933,529, issued April 19, 1960. As far as is known, however, no one heretofore has described or prepared any compounds which can be classed as p-xylylene bis quaternary ammonium compounds. This invention is therefore based in part on the discovery of such compounds, which have been found to be highly effective cationic fabric softeners.
In the use of cationic fabric softeners, such as dimethyl di-tallow ammonium chloride, an undesirable side effect is frequently obtained. While the fabric may be rendered anti-static, lint-free, and soft after application of the cationic agent, the fabric may tend to resist the absorption of water. Where water absorbency is an important property, such as with diapers, the tendency of the cationic fabric softener to produce a water-proofing effect, and to interfere with rewetting of the fabric, can be a serious problem. This problem tends to become more acute with repeated applications of the fabric softener. The quantity of the softener on the fabric will tend to buildaip with each application even though there are intervening washings of the fabric, and the rewet property of the fabric can be drastically curtailed.
The discovery that fabric softeners coming within the novel class of compounds of this invention have better rewet properties than previously known cationic fabric softeners is therefore of considerable importance. This invention is therefore particularly concerned with novel p-xylylene bis quaternary ammonium compounds which can be employed as fabric softeners while obtaining superior rewet properties. It will be understood of course that the novel chemical compounds of this invention can be used for other purposes.
The bis quaternary ammonium compounds of this invention can be represented by the following structural formula:
1'2: 1'1: H may-om-Qom-wen. 2x-
In the above formula, R is an aliphatic hydrocarbon group of from 14 to 22 carbon atoms, R; and R are members of the class consisting of methyl, ethyl, hydroxyethyl and hydroxypropyl, and X is an ammonium salt anion. Preferably, R is a saturated alkyl group of from 16 to 18 carbon atoms, such as an octadecyl group. R can be derived from a mixed fatty acid source, the mixed alkyl and 'alkylene groups of the fatty acids of tallow are particularly desirable. The tallow hydrocarbon groups can be partially or completely hydrogenated to reduce the content of oleyl groups, thereby providing saturated hydrocarbon chains of from 16 to 18 carbon atoms, and predominately saturated C chains.
Notwithstanding the presence of the large phenyl or xylylene group in the center of the molecule, the comevaporation under reduced pressure.
Patented Nov. 1, 1966 pounds of this invention manifest good rewet properties when employed as cationic fabric softeners. However, the rewet properties tend to be even further improved where the R and R groups are hydro-xyethyl or hydroxypropyl groups. A classof compounds wherein R and R are hydnoxyethyl groups is particularly preferred. However, superior rewet properties are also obtained when R is a methyl group.
As indicated, the quaternary ammonium compounds of this invention are in their salt form, that is, they are associated with an ammonium salt anion. For use as cationic fabric softeners, it is desirable to have the compounds readly dissolvable or dispersible in water, and the salt form tends to accomplish this result. While any of the known ammonium salt anions can be used, it is preferred to employ anions which are known to promote the water solubiltiy or water dispersibility of the compounds. For example, X can be a halogen anion such as chloride, bromide, or iodine anions. Other anions can be substituted for various purposes, such as sulfate, methylsulfate, phoshate, acetate, citrate, tartrate, and the like. The compounds can be conveniently prepared, as will subsequently be described from reagents which result in X being choride or other halide anion. However, after formation, the chloride or halide anion can be exchanged for other anions, such as :those already listed. Procedures for accomplishing such an exchange are well-known in the art, such as metathesis with the halide form or by the use of anionexchange resins.
Among the specific compounds coming within the scope of the present invention are the following: p-xylylene bis (dimethyloctadecylarnmonium chloride), p-xylylene "bis (bishydroxyethyloctadecylammonium chloride), pxylylene ibis (bishydroxyethyloctadecylammonium chloride), p-xylylene bis (bishydroxyethylhexadecylammonium chloride), p-xylylene bis (bishydroxyethyl tallow ammonium chloride), etc.
The compounds of this invention can be readily prepared by reacting a xylene halide, such as p-xylylene chloride or a'u'-dichloro-p-Xylene, with a tertiary amine. This reaction can be readily carried out with the reactants dissolved in an inert organic solvent such as isopropanol, ethyl or butyl acetate, dimethyl formamide, etc. Two moles of the tertiary amine are reacted with each mole of the xylene halide to produce the his quaternary ammonium compound. The reaction is preferably EXAMPLE 1 A mixture consisting of p-xylylene chloride (0.25 mole, 43.8 g.), cctadecyldimethyl amine (0.55 mole, 169 g.), 380ml. of n-propyl alcohol and 20 ml. of water was refluxed for four hours. The solvent was removed by The residue was crystallized from a 4:1 mixture of ethyl acetate and isopropyl alcohol. The crystals were Washed with petroleum ether and air-dried. Yield of p-xylylene bis (dimethyloctadecylammonium chloride) was 196 g., 99.5% active by titration, 99% of theory.
EXAMPLE 2 A solution of p-xylylene chloride (0.1 mole, 17.5 g.), and octadecylbishydroxyethyl amine (0.23 mole,, 80.0 g.) in 200 ml. of N,N-dirnethyl formamide was maintained at l10l20 for three and one-half hours, cooled to room temperature and then poured into 600 ml. of acetone. The white precipitate was filtered, Washed with petroleum 3 ether and air-dried. Yield of p-xylylene bis (bishydroxyethyloctadecylammonium chloride) was 42 g., 94.5% active by titration, 46.5% of theory.
EXAMPLE 3 EXAMPLE 4 A solution of hexadecylbishydroxyethyl amine (0.4 mole, 131 g.), a'a'-dichloro-p-xylene (0.2 mole, 35.0)
and sodium iodide (3.0 g.) in 400 ml. of n-butyl acetate EXAMPLE A solution of tallow bishydroxyethyl amine (0.4 mole, 140 g., I.V.=31.6) a'u-dichloro-p-xylene (0.2 mole, 35.0 g.), and sodium iodide (3.0 g.) in 400 ml. of n-butyl acetate was brought from 50 to 130 (reflux temperature) in 15 minutes and maintained there for 1 hour. The mixture was cooled down to 40 and poured into 1 liter of acetone. The white solid was filtered and dried by exposure to air over the weekend. Yield of p-xylylene bis (bishydroxyethyl tallow ammonium chloride) was 105 g., 100% active by titration, 60% of theory.
In employing the compounds of this invention as cationic fabric softeners, it is preferred to, incorporate them in rinse water following the washing of the fabric. The softener compound can be used at a level ranging from .03 to .3% based on the weight of the fabric being treated (O.W.F). For most purposes, however, the compounds will be applied at the rate of from .065 to 0.1% (O.W.F.). The cationic softeners are particularly effective with cellulosic fabrics such as cotton fabrics. For example, the softeners can be used to treat cotton diapers, cotton sheets and pillowcases, etc. Since the compounds are highly substantive to cellulosic fabrics, the treatment of such fabrics will usually remove substantially all of the softener compound from the water solution.
The compounds described in the foregoing examples were tested for softening activity on cotton fabrics at levels ranging from .075 to .1% (O.W.F.). They were found to be highly effective softeners. For example, p-xylylene bis (bishydroxyethyloctadecylammonium chloride) was found to be equal in softening activity at a level of 075% to Arquad 2HT at a level of 0.1% (O.W.F.). Arquad 2HT is a commercial cationic softener manufactured by Armour and Company which has become accepted as one of the most effective softeners previously known. The trade name Arquad 2HT designates that the compound is di(hydrogenated tallow) dimethyl ammonium chloride.
The compounds of Examples 1 and 2 were compared in re-wet characteristics With Arquad 2HT at levels of 0.1% (O.W.F.). Family-type wash bundles were used composed principally of cotton fabrics. The softener compounds were applied in the last rinse following washing with a standard commercial alkyl aryl sulfonate detergent. The test' was carried on through four successive applications, and the re-wet time in seconds was measured in terms of average sinking time after each 5 application. The results are set forth below in TableA:
Table A Average Sinking Time (Seconds) N o. of Applications Ex. I Ex. II Arquad It can be seen from the foregoing data that the compounds of Examples I and II provide excellent re-Wet properties even after four applications, and that they are manifestly superior in this respect to Arquad 2HT.
While inthe foregoing specification this invention has been described in considerable detail with reference to specific embodiments thereof, it will be apparent to those skilled in the art that the invention is suspectible to. addi tional embodiments and that certain of the details described herein can be varied considerably Without departing from the principles of the invention. a
We claim:
.1. As a composition of matter the compound repre sented by the formula References Cited by the Examiner 50 UNITED STATES PATENTS 2,340,881 2/ 1944 Kelley et a1 2588.8 2,520,275 8/1950 Du Bois et al. 260567.6 2,597,947 5/1952 Oxley et a1 2528.8 XR 2,933,529 4/1960 Hwa 260-567.6 2,955,108 10/ 1960 Omietanski 2528.8 XR 3,003,954 10/1961 Brown 2528.8 3,079,436 2/1963 HWa 260567.6 3,095,373 6/1963 Blomfield 2528.8
CHARLES B. PARKER, Primary Examiner.
JULIUS GREENWALD, Examiner.
MAYER WEINBLATT, FLOYD. D. HIGEL,
Assistant Examiners.

Claims (1)

1. AS A COMPOSITION OF MATTER THE COMPOUND REPRESENTED BY THE FORMULA 1,4-DI(R1-N(+)(-R2)(-R3)-CH2-)BENZENE 2X(-) WHEREIN R1 IS AN ALIPHATIC HYDROCARBON GROUP HAVING FROM 14 TO 22 CARBON ATOMS, R2 AND R3 ARE MEMBERS OF THE CLASS CONSISTING OF HYDROXYETHYL AND HYDROXYPROPYL, AND X IS AN AMMONIUM SALT ANION.
US276157A 1963-04-29 1963-04-29 p-xylylene bis quaternary ammonium compounds Expired - Lifetime US3283005A (en)

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FR8042A FR1392948A (en) 1963-04-29 1964-04-24 New quaternary p-xylylene-bis-ammonium compounds
GB17532/64A GB1018443A (en) 1963-04-29 1964-04-28 ú­-xylylene bis quaternary ammonium compounds and their use as cationic fabric softeners

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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3467708A (en) * 1965-10-21 1969-09-16 Armour Ind Chem Co Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds
US3974220A (en) * 1972-08-08 1976-08-10 Hoechst Aktiengesellschaft Quaternary ammonium corrosion inhibitor and petroleum demulsifier
US4009193A (en) * 1973-12-22 1977-02-22 Basf Aktiengesellschaft Bisstyrylaryl compounds
US11866666B1 (en) 2023-01-20 2024-01-09 Saudi Arabian Oil Company Methods for corrosion reduction in petroleum transportation and storage

Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2340881A (en) * 1939-08-22 1944-02-08 Nat Oil Prod Co Composition for lubricating and softening textile fibers
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US2597947A (en) * 1946-01-25 1952-05-27 Celanese Corp Textile treating compositions
US2933529A (en) * 1956-01-09 1960-04-19 Rohm & Haas Symmetrical diquaternary ammonium compounds
US2955108A (en) * 1957-01-07 1960-10-04 Univ Ohio State Res Found Process for 1,1,1-trisubstituted hydrazinium chlorides
US3003954A (en) * 1957-07-19 1961-10-10 Staley Mfg Co A E Methods and compositions of matter for softening textile fibers, yarns, and fabrics
US3079436A (en) * 1955-11-25 1963-02-26 Rohm & Haas Bis-quaternary ammonium compounds
US3095373A (en) * 1959-01-30 1963-06-25 Wyandotte Chemicals Corp Fabric softeners

Patent Citations (8)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2340881A (en) * 1939-08-22 1944-02-08 Nat Oil Prod Co Composition for lubricating and softening textile fibers
US2597947A (en) * 1946-01-25 1952-05-27 Celanese Corp Textile treating compositions
US2520275A (en) * 1946-12-28 1950-08-29 Onyx Oil & Chemical Company Aromatic diquaternary ammonium compounds
US3079436A (en) * 1955-11-25 1963-02-26 Rohm & Haas Bis-quaternary ammonium compounds
US2933529A (en) * 1956-01-09 1960-04-19 Rohm & Haas Symmetrical diquaternary ammonium compounds
US2955108A (en) * 1957-01-07 1960-10-04 Univ Ohio State Res Found Process for 1,1,1-trisubstituted hydrazinium chlorides
US3003954A (en) * 1957-07-19 1961-10-10 Staley Mfg Co A E Methods and compositions of matter for softening textile fibers, yarns, and fabrics
US3095373A (en) * 1959-01-30 1963-06-25 Wyandotte Chemicals Corp Fabric softeners

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3467708A (en) * 1965-10-21 1969-09-16 Armour Ind Chem Co Aryl-substituted aliphatic benzyl and naphthyl-methylene quaternary ammonium compounds
US3974220A (en) * 1972-08-08 1976-08-10 Hoechst Aktiengesellschaft Quaternary ammonium corrosion inhibitor and petroleum demulsifier
US4009193A (en) * 1973-12-22 1977-02-22 Basf Aktiengesellschaft Bisstyrylaryl compounds
US11866666B1 (en) 2023-01-20 2024-01-09 Saudi Arabian Oil Company Methods for corrosion reduction in petroleum transportation and storage

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FR1392948A (en) 1965-03-19

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