US2047066A - Softening agent - Google Patents

Softening agent Download PDF

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Publication number
US2047066A
US2047066A US54246731A US2047066A US 2047066 A US2047066 A US 2047066A US 54246731 A US54246731 A US 54246731A US 2047066 A US2047066 A US 2047066A
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US
United States
Prior art keywords
sarcosine
stearyl
softening agent
stands
alkali metal
Prior art date
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
Application number
Inventor
Glietenberg Eugen
Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)
General Aniline Works Inc
Original Assignee
General Aniline Works Inc
Priority date (The priority date 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 date listed.)
Filing date
Publication date
Application filed by General Aniline Works Inc filed Critical General Aniline Works Inc
Application granted granted Critical
Publication of US2047066A publication Critical patent/US2047066A/en
Anticipated expiration legal-status Critical
Expired - Lifetime legal-status Critical Current

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Classifications

    • BPERFORMING OPERATIONS; TRANSPORTING
    • B60VEHICLES IN GENERAL
    • B60SSERVICING, CLEANING, REPAIRING, SUPPORTING, LIFTING, OR MANOEUVRING OF VEHICLES, NOT OTHERWISE PROVIDED FOR
    • B60S11/00Vehicle modifications for receiving separate lifting, supporting, or manoeuvring devices
    • DTEXTILES; PAPER
    • D06TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
    • D06MTREATMENT, NOT PROVIDED FOR ELSEWHERE IN CLASS D06, OF FIBRES, THREADS, YARNS, FABRICS, FEATHERS OR FIBROUS GOODS MADE FROM SUCH MATERIALS
    • D06M13/00Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment
    • D06M13/322Treating 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
    • D06M13/325Amines
    • D06M13/342Amino-carboxylic acids; Betaines; Aminosulfonic acids; Sulfo-betaines
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10STECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10S516/00Colloid systems and wetting agents; subcombinations thereof; processes of
    • Y10S516/01Wetting, emulsifying, dispersing, or stabilizing agents
    • Y10S516/06Protein or carboxylic compound containing
    • YGENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y10TECHNICAL SUBJECTS COVERED BY FORMER USPC
    • Y10TTECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
    • Y10T442/00Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
    • Y10T442/20Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
    • Y10T442/2352Coating or impregnation functions to soften the feel of or improve the "hand" of the fabric

Definitions

  • fatty acids of a high molecular weight I mean fatty acids containing at least 8 carbon .atoms in the molecule.
  • the softening agents cor respond to the probable general formula:
  • R stand for an aliphatic hydrocarbon radical which contains at least 7 carbon atoms and may be unsaturated
  • R1 means an aliphatic hydrocarbon radical such as an alkyl or a cycloalkyl group, for instance, CH: or CzHs
  • R2 represents a methylene group which may be substituted
  • X stands for hydrogen, ammonium (NH4) or a metallic equivalent.
  • condensation products are obtainable in the usual manner by causing a saturated or unsaturated higher fatty acid of the kind referred to above or a derivative thereof to react upon an aliphatic amino-monocarboxylic acid containing a primary or secondary aminogroup or a salt thereof...
  • the process itself can also be carried out with the halides, anhydrides or esters of the above mentioned fatty acids in the ,most varied In Germany July 18, 1930 8 Claims. (01. 252 1) manners. If, in the condensation, a. mixture of different saturated or unsaturated fatty acids of a high molecular weight is employed, valuable mixtures of condensation products are obtained.
  • the softening agents represent, in the form of 5 their alkali metal salts, colorless or weakly colored soap-like substances being soluble in water with a great frothing capacity. Contrary to the usual soaps of higher fatty acids the new courpounds show a better solubility in waterand a 10 greater stability to acid reagents. They are particularly distinguished by the fact that their alkali metal salts show a good softening effect on ⁇ artificial silk. j
  • Example 1 Viscose is dyed in a bath heated to 80 C. with 1% of Benzoblue 2B (Colour Index,
  • Ezample 2.Vis cose is dyed in a bath heated to 80-85" C. with 1% of Benzo fast red GL (Schultz 1923, 2nd volume, page 18)'.- 20% of sodium sulfate and 2% of the condensation product from so stearyl chloride and the sodium salt of butylfamine-acetic acid of the formula:
  • Example 3.A'qu ite similar effect is produced 40 by replacing the stearyl-sarcosine of Example .1
  • R stands for an aliphatic hydrocarbon radicalwhich contains at least ,7 carbon atoms and may be unsaturated
  • R1 means an alkyl or cycloalkyl radical
  • R2 represents a methylene radical which may be substituted
  • X stands for hydrogen, ammoniumor a metallic equivalent.
  • R stands for an aliphatic hydrocarbon radical containing at least 7 carbon atoms/R1 means a cycloalkyl group
  • X stands for an alkali metal
  • R stands for an aliphatic hydrocarbon radical containing at least? carbon atoms
  • X represents an alkali metal
  • A- viscose artificial silk material impregnated with a stearyl sarcosine alkali metal salt 8.

Description

Patented July 7, 1936 UNITED STATES PATENT OFFICE 2,047,066 SOFTENING AGENT Eugen Glietenberg, Leverkusen, near Cologne-onthe-Rhine,
Germany, assignor, by mesne as-,.
signments, to General Aniline Works, Inc., New
York, N. Y.
No Drawing. Application June 5, 1931, Serial N0.
The present invention relates to softening of cellulosic fibers, that is artificial silk and cotton, with the aid of water-soluble salts of aliphatic primary or secondary aminomonocarboxylic acids containing higher saturated or unsaturated fatty acid radicals as substituents attached to the nitrogen atom.
By fatty acids of a high molecular weight I mean fatty acids containing at least 8 carbon .atoms in the molecule. The softening agents cor respond to the probable general formula:
IE1 RCO-N-Rz-COOX wherein R stand for an aliphatic hydrocarbon radical which contains at least 7 carbon atoms and may be unsaturated, R1 means an aliphatic hydrocarbon radical such as an alkyl or a cycloalkyl group, for instance, CH: or CzHs, R2 represents a methylene group which may be substituted, and X stands for hydrogen, ammonium (NH4) or a metallic equivalent.
' Such products are, for instance, stearyl-sar-.
cosine of the formula:
and oleyl-sarcosine of the which, in the form of its sodium salt, is a soap-- like colorless substance soluble in water.
These condensation products are obtainable in the usual manner by causing a saturated or unsaturated higher fatty acid of the kind referred to above or a derivative thereof to react upon an aliphatic amino-monocarboxylic acid containing a primary or secondary aminogroup or a salt thereof... The process itself can also be carried out with the halides, anhydrides or esters of the above mentioned fatty acids in the ,most varied In Germany July 18, 1930 8 Claims. (01. 252 1) manners. If, in the condensation, a. mixture of different saturated or unsaturated fatty acids of a high molecular weight is employed, valuable mixtures of condensation products are obtained. \1 The softening agents represent, in the form of 5 their alkali metal salts, colorless or weakly colored soap-like substances being soluble in water with a great frothing capacity. Contrary to the usual soaps of higher fatty acids the new courpounds show a better solubility in waterand a 10 greater stability to acid reagents. They are particularly distinguished by the fact that their alkali metal salts show a good softening effect on {artificial silk. j
The following examples will illustrate the present invention but without limiting it thereto; the
parts are by weight.
Example 1.Viscose is dyed in a bath heated to 80 C. with 1% of Benzoblue 2B (Colour Index,
first edition Jan. 1924; page 104, No. 406) 10% of sodium'sulfate and 0.25 grams per liter of stearyl sarcosine (sodium salt). The addition of stearyl-sarcosine gives a soft touch to the silk. Likewise, the softening agent can be' added to the last rinsing.bath instead of being added to the dyeing bath. p
Ezample 2.Vis cose is dyed in a bath heated to 80-85" C. with 1% of Benzo fast red GL (Schultz 1923, 2nd volume, page 18)'.- 20% of sodium sulfate and 2% of the condensation product from so stearyl chloride and the sodium salt of butylfamine-acetic acid of the formula:
CHz-OHi-QHrOHi The addition of this stearic acid derivative imparts a soft touch to the-viscose.
Example 3.A'qu ite similar effect is produced 40 by replacing the stearyl-sarcosine of Example .1
by palmityl-sarcosine.
I claim:
' 1. The process which comprises acting on eellulosic fibers with condensation products of the probable general formula;
.R-C o rt-nr-o o ox' wherein R stands for an aliphatic hydrocarbon radicalwhich contains at least ,7 carbon atoms and may be unsaturated, R1 means an alkyl or cycloalkyl radical, R2 represents a methylene radical which may be substituted, and X stands for hydrogen, ammoniumor a metallic equivalent.
2. The process which comprises acting on cellulosic fibers with condensation products of the probable general formula:
wherein R stands for an aliphatic hydrocarbon radical containing at least 7 carbon atoms/R1 means a cycloalkyl group, and X stands for an alkali metal.
3. The process which comprises acting on artificial 'silk' and cotton fibers with condensation products of the probable general formula:
wherein R stands for an aliphatic hydrocarbon radical containing at least? carbon atoms, and X represents an alkali metal. I
4. The process which comprises acting on artificial silk and cotton fibersiwith the sodium salt of stearyl-sarcosine 5. A cellulosic textile material impregnated with a stearyl sarcosine alkali metal salt.
8. A- viscose artificial silk material impregnated with a stearyl sarcosine alkali metal salt.
EUGEN GLIE'I'ENBERG.
US54246731 1930-07-19 1931-06-05 Softening agent Expired - Lifetime US2047066A (en)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE1930I0011130 DE550905C (en) 1930-07-19 1930-07-19 Softener for rayon
GB2344630A GB360892A (en) 1930-07-19 1930-08-05 Improvements in or relating to means for connecting lifting jacks to vehicles

Publications (1)

Publication Number Publication Date
US2047066A true US2047066A (en) 1936-07-07

Family

ID=34465889

Family Applications (1)

Application Number Title Priority Date Filing Date
US54246731 Expired - Lifetime US2047066A (en) 1930-07-19 1931-06-05 Softening agent

Country Status (6)

Country Link
US (1) US2047066A (en)
BE (1) BE381313A (en)
DE (1) DE550905C (en)
FR (1) FR720278A (en)
GB (1) GB360892A (en)
NL (1) NL30115C (en)

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE741891C (en) * 1938-09-10 1943-11-18 Zschimmer & Schwarz Chem Fab D Process for the preparation of water-soluble nitrogen-containing condensation products
US2471039A (en) * 1940-02-21 1949-05-24 Orthner Ludwig Manufacture of improved fibrous materials and the materials thus obtained
DE752675C (en) * 1940-02-03 1952-08-28 Ig Farbenindustrie Ag Softeners for textiles
US2746897A (en) * 1953-01-19 1956-05-22 American Enka Corp Method for the manufacture of cellulose-reinforced rubber articles
US2767200A (en) * 1953-09-14 1956-10-16 Gustav W Rapp Reaction product of copper gluconate and alkali metal salt of n-lauroyl sarcosin
US2778773A (en) * 1953-06-01 1957-01-22 Colgate Palmolive Co Guanidine salts of nu-higher aliphatic amino carboxylic acids and compositions thereof
US2877178A (en) * 1955-12-20 1959-03-10 Gen Aniline & Film Corp Ampholytic compositions in wet treatments
US2919197A (en) * 1954-02-26 1959-12-29 Lever Brothers Ltd Method of preparing oil-in-water emulsions
US2964425A (en) * 1958-04-29 1960-12-13 Socony Mobil Oil Co Inc Waterproofing of leathers
US3074980A (en) * 1958-12-18 1963-01-22 Procter & Gamble Process for making acyl amides of amino acid salts
US3170877A (en) * 1961-12-21 1965-02-23 Gen Aniline & Film Corp Antistatic treating solution for polyacrylonitrile fibers and method
US3244624A (en) * 1961-09-04 1966-04-05 Bayer Ag Treatment of synthetic filaments and composition therefor
USH1513H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Oleoyl sarcosinate with polyhydroxy fatty acid amides in cleaning products
USH1514H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Detergent compositions with oleoyl sarcosinate and polymeric dispersing agent

Cited By (14)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE741891C (en) * 1938-09-10 1943-11-18 Zschimmer & Schwarz Chem Fab D Process for the preparation of water-soluble nitrogen-containing condensation products
DE752675C (en) * 1940-02-03 1952-08-28 Ig Farbenindustrie Ag Softeners for textiles
US2471039A (en) * 1940-02-21 1949-05-24 Orthner Ludwig Manufacture of improved fibrous materials and the materials thus obtained
US2746897A (en) * 1953-01-19 1956-05-22 American Enka Corp Method for the manufacture of cellulose-reinforced rubber articles
US2778773A (en) * 1953-06-01 1957-01-22 Colgate Palmolive Co Guanidine salts of nu-higher aliphatic amino carboxylic acids and compositions thereof
US2767200A (en) * 1953-09-14 1956-10-16 Gustav W Rapp Reaction product of copper gluconate and alkali metal salt of n-lauroyl sarcosin
US2919197A (en) * 1954-02-26 1959-12-29 Lever Brothers Ltd Method of preparing oil-in-water emulsions
US2877178A (en) * 1955-12-20 1959-03-10 Gen Aniline & Film Corp Ampholytic compositions in wet treatments
US2964425A (en) * 1958-04-29 1960-12-13 Socony Mobil Oil Co Inc Waterproofing of leathers
US3074980A (en) * 1958-12-18 1963-01-22 Procter & Gamble Process for making acyl amides of amino acid salts
US3244624A (en) * 1961-09-04 1966-04-05 Bayer Ag Treatment of synthetic filaments and composition therefor
US3170877A (en) * 1961-12-21 1965-02-23 Gen Aniline & Film Corp Antistatic treating solution for polyacrylonitrile fibers and method
USH1513H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Oleoyl sarcosinate with polyhydroxy fatty acid amides in cleaning products
USH1514H (en) * 1994-06-01 1996-01-02 The Procter & Gamble Company Detergent compositions with oleoyl sarcosinate and polymeric dispersing agent

Also Published As

Publication number Publication date
FR720278A (en) 1932-02-20
DE550905C (en) 1932-05-24
BE381313A (en) 1931-08-31
GB360892A (en) 1931-11-05
NL30115C (en) 1933-06-15

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