US3578592A - Imidazoline quaternary salts as soil retardants - Google Patents

Imidazoline quaternary salts as soil retardants Download PDF

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Publication number
US3578592A
US3578592A US672461A US3578592DA US3578592A US 3578592 A US3578592 A US 3578592A US 672461 A US672461 A US 672461A US 3578592D A US3578592D A US 3578592DA US 3578592 A US3578592 A US 3578592A
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United States
Prior art keywords
soil
pile
carpets
carpet
retardants
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Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.)
Expired - Lifetime
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US672461A
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English (en)
Inventor
Joseph John Pontelandolfo
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Wyeth Holdings LLC
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American Cyanamid Co
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Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D233/00—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings
    • C07D233/04—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member
    • C07D233/06—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms
    • C07D233/08—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms
    • C07D233/12—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, not condensed with other rings having one double bond between ring members or between a ring member and a non-ring member with only hydrogen atoms or radicals containing only hydrogen and carbon atoms, directly attached to ring carbon atoms with alkyl radicals, containing more than four carbon atoms, directly attached to ring carbon atoms with substituted hydrocarbon radicals attached to ring nitrogen atoms
    • C07D233/16—Radicals substituted by nitrogen atoms
    • 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
    • D06M13/35—Heterocyclic compounds
    • 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
    • D06M13/47—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds
    • D06M13/473—Compounds containing quaternary nitrogen atoms derived from heterocyclic compounds having five-membered heterocyclic rings

Definitions

  • R represents an alkyl group of from 15 to 21 carbon atoms and the X is a halide ion of the group consisting of chloride, bromide and iodide.
  • Soil retardants heretofore used or suggested include colloidal dispersions of inorganic oxides, such as silica, alumina, titania, and the like. These inorganic colloids are useful to some degree but have short service life, especially when carpets treated therewith are vacuumed. The inorganic colloids also cause discoloration or whitening of the treated carpets so that an undesirable change in shade occurs even before the carpet is put into service use.
  • soil retardants of organic nature have been employed. This type also suffers from deficiencies including one or more of the following, depending on the specific organic variety: (1) not universally effective on carpets of all fiber types; (2) impart stiffness or rigidity to the carpet pile resulting in undesirable hand or lie of such pile and embrittlement thereof; (3) cause discoloration or whitening of the carpet leading to an "ice undesirable change in shade even before service use; (4) lack reasonable durability to service use and cleaning, particularly when vacuuming; (5) require uneconomical usage levels for effectiveness.
  • soil retardants which are effective on carpets of all fiber types and which overcome the deficiencies of the prior art soil retardants.
  • An object of the invention is to provide compositions of matter useful for imparting durable soil resistance or retardance to textile materials, particularly fiat or pile of all types, without causing discoloration or rigidity.
  • Another object of the invention is to provide a method for imparting durable soil retardance to textile materials such as fiat or pile carpets.
  • a further object of the invention is to provide soil retardant textiles, particularly carpets of all fiber types and color, which also substantially retain their original coloration and hand, even after repeated vacuumings.
  • imidazolinium halides of Formulas I and II can be used as durable soil retardants for non-cellulosic fibrous textile materials, and particularly for pile type fabrics such as rugs and carpets. It has also been discovered that concentrated, stable aqueous dispersions of the quaternary salts can be made by incorporating therein a formaldehyde-bisulfite stabilizing agent.
  • the imida'zolines from which the imidazolinium salts of Formulas I and II are prepared, can be formed by reacting a fatty acid of from 12 to 22 carbon atoms with diethylenetriamine according to published procedures.
  • the preferred starting imidazoline is 1-(2-stearoylaminoethyl)-2-heptadecylimidazoline, prepared from two moles of stearic acid and one mole of diethylenetriamine.
  • the imidazolinium halides of Formulas I and II are obtained by reacting the corresponding imidazoline with an alkylating agent that will provide the 2,3-dihydroxypropyl group and the halide anion X-.
  • alkylating agents include the halohydrins, i.e., halo-propanediols, such as S-chloro-1,2-propanediol, 3-bron1o-1,2-propanediol, and 3-iodo-l,2-propanediol, and the epihalohydrins, such as epichlorohydrin, epibromohydrin and epiiodohydrin.
  • the reaction between the imidazolines and the alkylating agent is conveniently carried out in water at a temperature of -95 C. Although theoretically a minimum of one mole of alkylating agent is required per mole of imidazoline for imidazolinium halides of Formula I and two moles for imidazolinium halides of Formula II, it is advantageous to use an excess (up to three moles) to obtain maximum fluidity of product.
  • the preferred quaternary salts are l-(2-stearoylaminoethyl) 2 heptadecyl l- (2,3-dihydroxyprop yl)imidazolinium chloride and 1 (2-stearoylaminoethyl)-2-heptadecyl 1,3 bis(2,3-dihydroxypropyl)imidazolinium dichloride, and mixtures thereof.
  • the imidazolinium salts (Formulas I and II) are conveniently applied to the textile materials as aqueous dispersions.
  • the physical properties, including stability, homogeneity and fluidity, are improved by incorporating therein a formaldehyde-bisulfite addition product.
  • a formaldehyde-bisulfite addition product Between 0.7% and 7.0%, preferably between 1.7% and 3.5%, based on the weight of the imidazoline, of the formaldehyde-bisul-fite addition product should be employed.
  • Addition of the formaldehyde-bisulfite stabilizer to an equeous dispersion containing about by weight of the imidazolinium halides changes the composition from a paste to a fluid.
  • the stabilized aqueous compositions containing the imidazolinium halides of Formulas I and II are applied to fibrous textile materials, either to the finished goods or during manufacture thereof, by any suitable means such as dipping, padding, spraying, coating, and the like.
  • spraying is the preferred technique, although mechanical applicators may be used on previously installed carpeting.
  • the amount of solids of the composition applied to the fibrous material is not critical and may vary from about 0.1 to about 10.0%, based on the weight of fibrous material.
  • the amount of solids applied to carpet pile will be between 0.5 and 5.0% based on the weight of the pile.
  • the treating composition should contain sufiicient solids to deposit the required amount on the fibrous material by the particular application method employed.
  • the fibrous material is allowed to dry so as to remove the water. Drying may be accomplished at ambient conditions or, where possible, at elevated temperatures.
  • the use of an oven circulating hot air at about 140 F. has been found particularly advantageous. The time required for drying in such ovens will depend on the temperature of the oven and the amount of water in the carpet pile.
  • compositions of this invention are effective on noncellulosic fibers of all types, natural and synthetic, singly or in blends.
  • synthetic fibers such as nylon, acrylics, polyesters, and the like.
  • the fibers are in the form of a carpet with loop or cut pile.
  • carpets may contain a backing material, for example, burlap, and the backing material may be treated with resins or rubber, etc.
  • EXAMPLE 1 This example shows the preparation of an imidazoline of the following formula:
  • a solution of 1,704 parts (6.0 moles) of stearic acid in about 1,050 parts of xylene was prepared by melting the stearic acid and adding the xylene.
  • 310 parts (3.0 moles) of diethylenetriamine was added slowly while keeping the temperature below 90 C.
  • the mixture was then heated at 110-115 C. under sufiiicent vacuum to cause azeotropic distillation of the water of reaction.
  • the last amount of water was removed at a temperature of about 120 C.
  • the xylene was then distilled and the residue was dried.
  • the product was the desired 1-(Z-stearoylaminoethyl) 2 heptadecylimidazoline, shown above.
  • EXAMPLE 3 An aqueous dispersion containing 2.8% of solids was prepared by mixing 13.3 parts of the product of Example 2 with sufiicient water to make 100 parts. The dispersion *was applied by spraying to a 12" x 12" carpet sample consisting of cut nylon pile and 50% burlap backing. Spraying was confined to the pile and the carpet sample increased 50% in weight. Since the carpet increased in Weight by 50% and contained 50% pile to which the spray was directed, it may be concluded that the pile actually increased in weight by 100% and thus the pile contained solids equal to the concentration of the application hath, that is, 2.8%. The treated carpet was dried in an oven circulating hot air at C. After drying, the carpet was vacuumed to remove loose pile and incidental dirt.
  • soil index below 1.00 indicate retardancy and the lower the said value, the more favorable is the soil retardancy.
  • the untreated control in a soiling test is arbitrarily defined as having a soil index of 1.00 and performance of other samples is calculated on this basis.
  • Good soil retarders generally have a value below about 0.70.
  • EXAMPLE 5 A concentrated aqueous dispersion of the product of Example 1 was prepared by vigorously mixing 300 parts of the product of Example 1 into 1200 parts of Water containing 60 parts of a cationic surface active agent obtained by reacting a long-chain alkyl amine with ethylene oxide.
  • EXAMPLE 6 Three aqueous dispersions containing 2% of active solids were prepared from the products of Examples 4a, 4b and 5. The dispersions were applied to nylon carpet by the procedure described in Example 3. The results are shown in Table III.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
US672461A 1967-09-15 1967-10-03 Imidazoline quaternary salts as soil retardants Expired - Lifetime US3578592A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
US66817867A 1967-09-15 1967-09-15
US67246167A 1967-10-03 1967-10-03

Publications (1)

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US3578592A true US3578592A (en) 1971-05-11

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US (1) US3578592A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
BE (1) BE720818A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
FR (1) FR1582293A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)
NL (1) NL6813141A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html)

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862045A (en) * 1971-11-15 1975-01-21 Kao Corp Antistatic softening composition
US3920563A (en) * 1972-10-31 1975-11-18 Colgate Palmolive Co Soap-cationic combinations as rinse cycle softeners
GB2253855A (en) * 1990-09-28 1992-09-23 Sandoz Ltd Carpet backing compositions
WO2009076258A1 (en) * 2007-12-07 2009-06-18 Nalco Company Environmentally friendly bis-quaternary compounds for inhibiting corrosion and removing hydrocarbonaceous deposits in oil and gas applications

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
FR2509302A1 (fr) * 1981-03-04 1983-01-14 Vyzk Ustav Zuslechtovaci Composes d'ammonium quaternaire, procede pour leur fabrication et utilisation de ces produits dans les apprets de finissage des tissus
DE3722186A1 (de) * 1987-07-04 1989-01-12 Cassella Ag Verfahren zur herstellung von in 2-stellung substituierten 1-(acylaminoalkyl)-2-imidazolinen
DE3807246A1 (de) * 1988-03-05 1989-09-14 Cassella Ag Verfahren zur herstellung von in 2-stellung substituierten 1-(acylaminoalkyl)-2-imidazolinen

Cited By (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US3862045A (en) * 1971-11-15 1975-01-21 Kao Corp Antistatic softening composition
US3920563A (en) * 1972-10-31 1975-11-18 Colgate Palmolive Co Soap-cationic combinations as rinse cycle softeners
GB2253855A (en) * 1990-09-28 1992-09-23 Sandoz Ltd Carpet backing compositions
WO2009076258A1 (en) * 2007-12-07 2009-06-18 Nalco Company Environmentally friendly bis-quaternary compounds for inhibiting corrosion and removing hydrocarbonaceous deposits in oil and gas applications
US7951754B2 (en) 2007-12-07 2011-05-31 Nalco Company Environmentally friendly bis-quaternary compounds for inhibiting corrosion and removing hydrocarbonaceous deposits in oil and gas applications

Also Published As

Publication number Publication date
NL6813141A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1969-03-18
BE720818A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1969-03-13
FR1582293A (GUID-C5D7CC26-194C-43D0-91A1-9AE8C70A9BFF.html) 1969-09-26

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