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US2596985A - Fatty acid polyglycol-aliphatic amine combinations useful as textile softeners and process for producing the same - Google Patents

Fatty acid polyglycol-aliphatic amine combinations useful as textile softeners and process for producing the same Download PDF

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US2596985A
US2596985A US134149A US13414949A US2596985A US 2596985 A US2596985 A US 2596985A US 134149 A US134149 A US 134149A US 13414949 A US13414949 A US 13414949A US 2596985 A US2596985 A US 2596985A
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fatty acid
water soluble
aliphatic amine
acid
textile
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US134149A
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Alton A Cook
Sapers Ira
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Arkansas Co Inc
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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
    • D06M13/325—Amines
    • D06M13/332—Di- or polyamines

Definitions

  • the present invention relates to textile processing chemicals and methods of making the same, and it particularly relates to fatty acidpolyethylene glycol-aliphatic amine combinations having particular utility as textile softening and finishing agents and having cationic characteristics.
  • the first step is preferably carried out at a temperature of 100 C. to 140 C., and desirably at 110 C. to 125 C., for 1 to 4 hours, while the second step is carried out at a temperature of 25 C. to 50 C. or higher, as for example at 140 C. to 180 C., and desirably 150 C. to 165 C., for about one to three hours.
  • 1 mol of fatty acid is combined with the polyethylene glycol in an amount ranging from to /2 of a mol, depending upon the molecular weight of the glycol which may range from 400 to about 1500 or over, in the presence of an acid catalyst, such as an alkylated naphthalene sulfonic acid.
  • an acid catalyst such as an alkylated naphthalene sulfonic acid.
  • the polyethylene glycol has become practically completely esterified to form a di-ester with the fatty acid.
  • the amine preferably a primary or secondary water-soluble alkanolamine
  • the second step of the reaction is normally carried out at the preferred range of temperature until the acid number of the mixture ranges from 5 to 20.
  • the final products are highly complex mixtures 2 and include esters, amides and amino-esters. They are usually soluble or dispersible in water and are alkaline in reaction, a l solution having a pH of 8 to 9.
  • these products may be neutralized or acidified with organic acids, such as acetic, formic or lactic acids, for the purpose of producing finishes having definite substantivity to textile fibers.
  • organic acids such as acetic, formic or lactic acids
  • They may also be alkylated with dimethyl or diethyl sulfate preferably in alkaline media at about C. to produce more soluble compounds which also act as substantive finishes for textile fibers.
  • the ingredients used in this invention fall into three classes of compound and at least one compound of each of the following classes is necessary to the manufacturer of the products described herein.
  • Class 1 Water-soluble aliphatic saturated polyalcohol having at least four carbon atoms and at least 2 hydroxyl groups and a melting point preferably under 100 C.
  • EmampZes. Polyethylene glycols ofvarious average molecular weights from 200 to 1500 and polypropylene glycols having molecular weights from 400 to 1200.
  • Alkoxy derivatives such as methoxyor ethoxypolyethylene glycols having molecular weights of 350 to 750 or over may be employed.
  • Class 2.Mono-carboxylic fatty acids having from 16 to 26 carbon atoms.
  • the saturated fatty acids C16 to C20 are preferred. This includes mixed fatty acids obtained from splitting natural fats and waxes.
  • Example-Palmitic and stearic acids are preferred. Eruci'c, montanic, arachidic, beh'enic, lignoceric and cerotic and mixed fatty acids from tallow, Japan wax and hydrogenated oils (averaging about 20 carbon atoms per molecule) may also be used.
  • Class 3. Water-soluble aliphatic saturated amines with two or more amino groups or one amino group and one or more hydroxyl groups, excluding tertiary amines.
  • polyalkylene polyamines such as ethylene diamine; diethylene triamine; tri- 5 ethylene tetramine; tetraethylene pentamme.
  • Example I As the first step, 284 parts of stearic acid and 150 parts of polyethylene glycol having a molecular weight of about 600 are heated in the pres ence of 1 part of butyl naphthalene sulfonic acid at 110 C. to 120 C. for 2 hours or until the polyethylene glycol is completely used up to form a di-ester.
  • Hydrogenated fatty acid (average molecular Weight 310) 20 carbon atoms 310 1 Polyethylene glycol having a molecular weight of about 1000 200 g Monobutyl naphthalene sulionic acid 2. 5 Second Step:
  • Palmitic acid 256 l Polyethylene glycol having a molecular weight of about 400 100 Sulfuric acid 0.2 Second Step:
  • Stearic Acid 284 l Polyethylene glycol having a molecular weight of about 1500 -1 30 Mixed alkane sulionic acids 2. 5 Second Step:
  • Diethylene trimnine 75 l The products made by the processes of Examples I to V are usually soft solids of a Waxy consistency and are diluted with Water either as produced or after acidification for actual use as textile finishes. In consistency these (11- luted products are soft to stiff pastes which disperse readily in water at any pH adjustment between 4.0 and 10.0. In concentration these preparations may vary from 10% up to 50% or more active ingredients.
  • these compounds When used as softeners or finishing agents on woolen, rayon or cotton goods, these compounds in their diluted or acidified form as set forth in Examples .VI and VII are employed in amounts of from 1% to 10% on the weight of the material being processed and in aqueous concentrations of from- 0.1% up to about 2%. At a pH range of from 4.0 to 6.0 these finishes are markedly substantive and exhaust from the finishing bath like dyestufi's, While at higher pH ranges they are not as highly substantive, but donot have as adverse effects on the light fastness of the dyestufis as the acidified products.
  • Example VI 33 parts of the product of Example I are heated to molten condition and poured with continual stirring into 65 parts of water containing 2 parts of formic acid. The stirring is continued until it forms a thick whitish paste, which is readily soluble in warm water.
  • Emample VII 23 parts of the product of Example III in molten condition are mixed thoroughly with 75 parts of W te Co t i of acetic acid. The stirring is continued until a paste is formed which is readily dispersible in hot water.
  • a process of preparing textile softeners which comprises heating a high molecular weight saturated fatty acid, said fatty acid having 16 to 26 carbon atoms, with a polyalkylene glycol at C. to C. for about 1 to 4 hours, and then heating the reaction mixture with a Water soluble aliphatic amine at 140 C. to C. for 1 to 3 hours, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
  • a process of preparing textile softeners which comprises heating a high molecular weight saturated fatty acid, said fatty acid having 16 to 26 carbon atoms, with a polyalkylene glycol at 100 C. to 140 C. until the polyalkylen glycol has been completely esterified to form a di-ester and then heating the reaction mixture with a water soluble aliphatic amine at 140 C. to 180 C. until the acid number is 5 to 10, said amine being selected from the group consisting of the Water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
  • a process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms, with about ,40 to /2 mol of a polyalkylene glycol at 100 C. to 140 C. for about 1 to 4 hours and until the polyalkylene glycol has been completely esterified to form a di-ester in the presence of an acid catalyst, and then heating the reaction mixture with A,, to 1%, mols of a water soluble aliphatic amine at 140 C. to 180 C. for 1 to 3 hours and until the acid number is 5 to 10, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
  • a process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms with about V to 5 2 mol of a polyethylene glycol 400 to 1600 at 110 C. to 125 C. for about 1 to 4 hours to form a di-ester in the presence of an acid catalyst, and then heating the reaction mixture with A to 1% mols of a water soluble alkanolamine at 150 C. to 165 C. for 1 to 3 hours until the acid number is 5 to 10, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
  • a process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms, with about & to /2 mol of a polyethylene glycol 400 to 1600 at 110 C. to 125 C. for about 1 to 4 hours to form a di-ester in the presence of an acid catalyst, and
  • reaction mixture then heating the reaction mixture with A to 1% mols of a water soluble alkanolamine at C. to C. for 1 to 3 hours until the acid number is 5 to 10 and then acidifying with a water soluble organic acid, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the Water soluble polyalkylene polyamines.
  • a textile softener comprising high molecular weight fatty acid-polyalkylene glycol-water soluble aliphatic amine combination produced according to claim 1.
  • a textile softener comprising the acidified aqueous dispersion of high molecular weight fatty acid-polyalkylene glycol-water soluble aliphatic amine combination produced according to claim 1.

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  • Engineering & Computer Science (AREA)
  • Textile Engineering (AREA)
  • Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)

Description

Patented May 20, 1952 UNITED STATES PTNT OFFICE Alton A. Cook, Glen Ridge, and Ira Sapers, Newark, N. J assignors to Arkansas Company, Inc., Newark, N. J a corporation of New York No Drawing. Application December 20, 1949, Serial No. 134,149
9 Claims.
The present invention relates to textile processing chemicals and methods of making the same, and it particularly relates to fatty acidpolyethylene glycol-aliphatic amine combinations having particular utility as textile softening and finishing agents and having cationic characteristics. I
It is among the objects of the present invention to provide novel fatty acid-polyethylene glycolaliphatic amine combinations useful as finishing and softening agents for textile fabrics.
Still further objects and advantages will appear in the more detailed description set forth below, it being understood, however, that this more detailed description is given by way of illustration and explanation only and not by way of limitation, since various changes may be made therein by those skilled in the art without departing from the scope and spirit of the present invention.
The first step is preferably carried out at a temperature of 100 C. to 140 C., and desirably at 110 C. to 125 C., for 1 to 4 hours, while the second step is carried out at a temperature of 25 C. to 50 C. or higher, as for example at 140 C. to 180 C., and desirably 150 C. to 165 C., for about one to three hours.
In the first step, 1 mol of fatty acid is combined with the polyethylene glycol in an amount ranging from to /2 of a mol, depending upon the molecular weight of the glycol which may range from 400 to about 1500 or over, in the presence of an acid catalyst, such as an alkylated naphthalene sulfonic acid.
At the end of this step, the polyethylene glycol has become practically completely esterified to form a di-ester with the fatty acid.
In the second step, the amine, preferably a primary or secondary water-soluble alkanolamine, should be present in an amount ranging from A2 of a mol to 1 mols and desirably from of a mol to 1% mols for each mol of fatty acid. The second step of the reaction is normally carried out at the preferred range of temperature until the acid number of the mixture ranges from 5 to 20.
The final products are highly complex mixtures 2 and include esters, amides and amino-esters. They are usually soluble or dispersible in water and are alkaline in reaction, a l solution having a pH of 8 to 9.
If desired, these products may be neutralized or acidified with organic acids, such as acetic, formic or lactic acids, for the purpose of producing finishes having definite substantivity to textile fibers.
They may also be alkylated with dimethyl or diethyl sulfate preferably in alkaline media at about C. to produce more soluble compounds which also act as substantive finishes for textile fibers.
It has been found in the present invention that where these two types of reactions are carried out by a definite succession of steps, as described above, by first combining the fatty acid and polyethylene glycol and then the aliphatic amine, products are obtained which have properties which would not be expected from a physical mixture of an amino fatty acid condensation product and a polyethylene glycol-fatty acid ester as is ordinarily known.
The ingredients used in this invention fall into three classes of compound and at least one compound of each of the following classes is necessary to the manufacturer of the products described herein.
Class 1.Water-soluble aliphatic saturated polyalcohol having at least four carbon atoms and at least 2 hydroxyl groups and a melting point preferably under 100 C.
EmampZes.--Polyethylene glycols ofvarious average molecular weights from 200 to 1500 and polypropylene glycols having molecular weights from 400 to 1200. Alkoxy derivatives, such as methoxyor ethoxypolyethylene glycols having molecular weights of 350 to 750 or over may be employed.
Class 2.Mono-carboxylic fatty acids having from 16 to 26 carbon atoms. The saturated fatty acids C16 to C20 are preferred. This includes mixed fatty acids obtained from splitting natural fats and waxes.
Example-Palmitic and stearic acids are preferred. Eruci'c, montanic, arachidic, beh'enic, lignoceric and cerotic and mixed fatty acids from tallow, Japan wax and hydrogenated oils (averaging about 20 carbon atoms per molecule) may also be used.
Class 3.- -Water-soluble aliphatic saturated amines with two or more amino groups or one amino group and one or more hydroxyl groups, excluding tertiary amines.
ErampZes.Monoand di-ethanolamines;
3 monoand di-propanolamines; butyl-monoand di-ethanolamine; Z-methyl, 2 amino, l-propanol; and aminoethylethanolamine. Less preferred are polyalkylene polyamines such as ethylene diamine; diethylene triamine; tri- 5 ethylene tetramine; tetraethylene pentamme.
The following examples illustrate the procedure of preparing the two-step complex condensation products:
Example I As the first step, 284 parts of stearic acid and 150 parts of polyethylene glycol having a molecular weight of about 600 are heated in the pres ence of 1 part of butyl naphthalene sulfonic acid at 110 C. to 120 C. for 2 hours or until the polyethylene glycol is completely used up to form a di-ester.
Then in the second step 130 parts by weight of diethanolamine is added and the mixture is heated up to 160 C. for 2 hours until an acid number of about 10 has been achieved.
Example II Parts Mols First Step:
Hydrogenated fatty acid (average molecular Weight 310) 20 carbon atoms 310 1 Polyethylene glycol having a molecular weight of about 1000 200 g Monobutyl naphthalene sulionic acid 2. 5 Second Step:
Diethanolaminc H5 1. 1
Exam le III Parts Mols First Stop:
Palmitic acid 256 l Polyethylene glycol having a molecular weight of about 400 100 Sulfuric acid 0.2 Second Step:
Diethanolamine 53 Monocthanolamino 1 30 3 Example IV Parts Mols First Step:
Stearic Acid 284 l Polyethylene glycol having a molecular weight of about 1500 -1 30 Mixed alkane sulionic acids 2. 5 Second Step:
Aminoethylethanolamine 105 1 Eazample V Parts 7 Mols First Step:
Fatty acids from Japan wax 265 l Methoxypolyethylene glycol having a molecular weight of about 550 375 .2 Second Step:
Diethylene trimnine 75 l The products made by the processes of Examples I to V are usually soft solids of a Waxy consistency and are diluted with Water either as produced or after acidification for actual use as textile finishes. In consistency these (11- luted products are soft to stiff pastes which disperse readily in water at any pH adjustment between 4.0 and 10.0. In concentration these preparations may vary from 10% up to 50% or more active ingredients.
When used as softeners or finishing agents on woolen, rayon or cotton goods, these compounds in their diluted or acidified form as set forth in Examples .VI and VII are employed in amounts of from 1% to 10% on the weight of the material being processed and in aqueous concentrations of from- 0.1% up to about 2%. At a pH range of from 4.0 to 6.0 these finishes are markedly substantive and exhaust from the finishing bath like dyestufi's, While at higher pH ranges they are not as highly substantive, but donot have as adverse effects on the light fastness of the dyestufis as the acidified products.
The following are examples of preparation of the actual finishing compounds from some condensationproducts of Examples I to V:
Example VI 33 parts of the product of Example I are heated to molten condition and poured with continual stirring into 65 parts of water containing 2 parts of formic acid. The stirring is continued until it forms a thick whitish paste, which is readily soluble in warm water.
Emample VII 23 parts of the product of Example III in molten condition are mixed thoroughly with 75 parts of W te Co t i of acetic acid. The stirring is continued until a paste is formed which is readily dispersible in hot water.
The present application is a continuation in part of application Serial No. 747,598 filed May 12, 1947, Patent No. 2,491,478 dated December 20, 1949.
As many changes could be made in the above fatty acid-polyglycol-aliphatic amine combinations useful as textile softeners and process for producing the same, and many widely different embodiments of this invention could be made Without departing from the scope of the claims, it is intended that all matter contained in the above description shall be interpreted as illustrative and not in a limiting sense.
Having now particularly described and ascertained the nature of the invention, and in what manner the same is to be performed, what is claimed is:
l. A process of preparing textile softeners which comprises heating a high molecular weight saturated fatty acid, said fatty acid having 16 to 26 carbon atoms, with a polyalkylene glycol at C. to C. for about 1 to 4 hours, and then heating the reaction mixture with a Water soluble aliphatic amine at 140 C. to C. for 1 to 3 hours, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
2. A process of preparing textile softeners which comprises heating a high molecular weight saturated fatty acid, said fatty acid having 16 to 26 carbon atoms, with a polyalkylene glycol at 100 C. to 140 C. until the polyalkylen glycol has been completely esterified to form a di-ester and then heating the reaction mixture with a water soluble aliphatic amine at 140 C. to 180 C. until the acid number is 5 to 10, said amine being selected from the group consisting of the Water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
3. A process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms, with about ,40 to /2 mol of a polyalkylene glycol at 100 C. to 140 C. for about 1 to 4 hours and until the polyalkylene glycol has been completely esterified to form a di-ester in the presence of an acid catalyst, and then heating the reaction mixture with A,, to 1%, mols of a water soluble aliphatic amine at 140 C. to 180 C. for 1 to 3 hours and until the acid number is 5 to 10, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
4. A process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms with about V to 5 2 mol of a polyethylene glycol 400 to 1600 at 110 C. to 125 C. for about 1 to 4 hours to form a di-ester in the presence of an acid catalyst, and then heating the reaction mixture with A to 1% mols of a water soluble alkanolamine at 150 C. to 165 C. for 1 to 3 hours until the acid number is 5 to 10, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the water soluble polyalkylene polyamines.
5. A process of preparing textile softeners which comprises heating about 1 mol of a high molecular weight saturated fatty acid, said fatty acid having 16 to 20 carbon atoms, with about & to /2 mol of a polyethylene glycol 400 to 1600 at 110 C. to 125 C. for about 1 to 4 hours to form a di-ester in the presence of an acid catalyst, and
then heating the reaction mixture with A to 1% mols of a water soluble alkanolamine at C. to C. for 1 to 3 hours until the acid number is 5 to 10 and then acidifying with a water soluble organic acid, said amine being selected from the group consisting of the water soluble primary and secondary alkanolamines and the Water soluble polyalkylene polyamines.
6. A textile softener comprising high molecular weight fatty acid-polyalkylene glycol-water soluble aliphatic amine combination produced according to claim 1.
7. A textile softener comprising the acidified aqueous dispersion of high molecular weight fatty acid-polyalkylene glycol-water soluble aliphatic amine combination produced according to claim 1.
8. A textile softener prepared specifically according to the process of claim 4.
9. A textile softener produced specifically according to the process of claim 5.
ALTON A. COOK.
IRA SAPERS.
REFERENCES CITED The following references are of record in the file of this patent:
UNITED STATES PATENTS Number Name Date 2,390,942 Katzman et a1. Dec. 11, 1945 2,405,784 Geltner Aug. 13, 1946 2,491,478 Cook et a1 Dec. 20, 1949

Claims (1)

1. A PROCESS OF PREPARING TEXTILE SOFTENERS WHICH COMPRISES HEATING A HIGH MOLECULAR WEIGHT SATURATED FATTY ACID, SAID FATTY ACID HAVING 16 TO 26 CARBON ATOMS, WTH A POLYALKYLENE GLYCOL AT 100* C. TO 140* C. FOR ABOUT 1 TO 4 HOURS, AND THEN HEATING THE REACTION MIXTURE WITH A WATER SOLUBLE ALIPHATIC AMINE AT 140* C. TO 180* C. FOR 1 TO 3 HOURS, SAID AMINE BEING SELECTED FROM THE GROUP CONSISTING OF THE WATER SOLUBLE PRIMARY AND SECONDARY ALKANOLAMINES AND THE WATER SOLUBLE POLYALKYLENE POLYAMINES.
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Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2806804A (en) * 1952-12-29 1957-09-17 Drew & Co Inc E F Method of treating wool
US2821316A (en) * 1955-05-27 1958-01-28 Canadian Mobile Co Ltd Roll clamp for lift truck
US2828229A (en) * 1953-12-18 1958-03-25 Spinnfaser Ag Cellulose fibres coated with cotton wax
US2985543A (en) * 1958-04-04 1961-05-23 Atlantic Refining Co Anti-static treatment and products resulting therefrom
US3038820A (en) * 1955-07-15 1962-06-12 Ciba Ltd Process for imparting a soft feel to textile fibers
US3116162A (en) * 1960-01-28 1963-12-31 Ici Ltd Textile treatment
US3230183A (en) * 1961-07-07 1966-01-18 Onyx Chemical Corp Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
US3257233A (en) * 1963-04-08 1966-06-21 Gen Mills Inc Textile fabric treated with ditertiary amine obtained from a secondary amine and polyoxyethylene glycol and the quaternary obtained therefrom
US3305392A (en) * 1965-05-27 1967-02-21 Scott Paper Co Modified fibrous web and process of manufacture
US3327502A (en) * 1966-11-23 1967-06-27 American Can Co Knitted paper fabric
US3936480A (en) * 1971-07-08 1976-02-03 Rhone-Progil Additives for improving the dispersing properties of lubricating oil
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
US4326966A (en) * 1979-06-20 1982-04-27 Ceskoslovenska Akademie Ved Agent for textile livening with an antistatic effect and favorable dermatologic properties
US4515723A (en) * 1981-07-10 1985-05-07 Hoechst Aktiengesellschaft Quaternary N-alkyl-N,N',N'-polyoxyalkyl-α,ω-diamino-alkylene fatty acid esters, and their use
US4634450A (en) * 1983-07-06 1987-01-06 Bergvik Kemi Ab Coal-water dispersion

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2390942A (en) * 1941-10-13 1945-12-11 Emulsol Corp Ethers of alcohol amines
US2405784A (en) * 1946-08-13 Derivatives of chlormethyl ethers
US2491478A (en) * 1947-05-12 1949-12-20 Arkansas Company Inc Polyalcohol-fatty acid-aliphatic amine combinations useful as textile assistants andprocess of producing the same

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2405784A (en) * 1946-08-13 Derivatives of chlormethyl ethers
US2390942A (en) * 1941-10-13 1945-12-11 Emulsol Corp Ethers of alcohol amines
US2491478A (en) * 1947-05-12 1949-12-20 Arkansas Company Inc Polyalcohol-fatty acid-aliphatic amine combinations useful as textile assistants andprocess of producing the same

Cited By (15)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US2806804A (en) * 1952-12-29 1957-09-17 Drew & Co Inc E F Method of treating wool
US2828229A (en) * 1953-12-18 1958-03-25 Spinnfaser Ag Cellulose fibres coated with cotton wax
US2821316A (en) * 1955-05-27 1958-01-28 Canadian Mobile Co Ltd Roll clamp for lift truck
US3038820A (en) * 1955-07-15 1962-06-12 Ciba Ltd Process for imparting a soft feel to textile fibers
US2985543A (en) * 1958-04-04 1961-05-23 Atlantic Refining Co Anti-static treatment and products resulting therefrom
US3116162A (en) * 1960-01-28 1963-12-31 Ici Ltd Textile treatment
US3230183A (en) * 1961-07-07 1966-01-18 Onyx Chemical Corp Addition products of polyamines with polyalkoxy compounds and textiles treated therewith
US3257233A (en) * 1963-04-08 1966-06-21 Gen Mills Inc Textile fabric treated with ditertiary amine obtained from a secondary amine and polyoxyethylene glycol and the quaternary obtained therefrom
US3305392A (en) * 1965-05-27 1967-02-21 Scott Paper Co Modified fibrous web and process of manufacture
US3327502A (en) * 1966-11-23 1967-06-27 American Can Co Knitted paper fabric
US3936480A (en) * 1971-07-08 1976-02-03 Rhone-Progil Additives for improving the dispersing properties of lubricating oil
US4129506A (en) * 1975-09-04 1978-12-12 Hoechst Aktiengesellschaft Fabric softeners
US4326966A (en) * 1979-06-20 1982-04-27 Ceskoslovenska Akademie Ved Agent for textile livening with an antistatic effect and favorable dermatologic properties
US4515723A (en) * 1981-07-10 1985-05-07 Hoechst Aktiengesellschaft Quaternary N-alkyl-N,N',N'-polyoxyalkyl-α,ω-diamino-alkylene fatty acid esters, and their use
US4634450A (en) * 1983-07-06 1987-01-06 Bergvik Kemi Ab Coal-water dispersion

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