US2576896A - Compositions of matter for producing a softening effect on textiles - Google Patents
Compositions of matter for producing a softening effect on textiles Download PDFInfo
- Publication number
- US2576896A US2576896A US755709A US75570947A US2576896A US 2576896 A US2576896 A US 2576896A US 755709 A US755709 A US 755709A US 75570947 A US75570947 A US 75570947A US 2576896 A US2576896 A US 2576896A
- Authority
- US
- United States
- Prior art keywords
- acid
- parts
- water
- textiles
- weight
- 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
Links
- 239000000203 mixture Substances 0.000 title claims description 10
- 239000004753 textile Substances 0.000 title claims description 8
- 230000000694 effects Effects 0.000 title claims description 6
- 239000006185 dispersion Substances 0.000 claims description 23
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 claims description 17
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 17
- 239000000194 fatty acid Substances 0.000 claims description 17
- 229930195729 fatty acid Natural products 0.000 claims description 17
- 150000004665 fatty acids Chemical class 0.000 claims description 17
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 claims description 7
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 claims description 6
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 claims description 2
- -1 acyl radical Chemical class 0.000 description 17
- 150000003839 salts Chemical class 0.000 description 17
- 125000004432 carbon atom Chemical group C* 0.000 description 14
- 150000002148 esters Chemical class 0.000 description 13
- 235000021355 Stearic acid Nutrition 0.000 description 12
- 150000001732 carboxylic acid derivatives Chemical class 0.000 description 12
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 12
- OQCDKBAXFALNLD-UHFFFAOYSA-N octadecanoic acid Natural products CCCCCCCC(C)CCCCCCCCC(O)=O OQCDKBAXFALNLD-UHFFFAOYSA-N 0.000 description 12
- 239000008117 stearic acid Substances 0.000 description 12
- 239000002253 acid Substances 0.000 description 10
- 150000001556 benzimidazoles Chemical class 0.000 description 9
- 239000007859 condensation product Substances 0.000 description 7
- XMYQHJDBLRZMLW-UHFFFAOYSA-N methanolamine Chemical compound NCO XMYQHJDBLRZMLW-UHFFFAOYSA-N 0.000 description 7
- 210000002268 wool Anatomy 0.000 description 7
- 229910052799 carbon Inorganic materials 0.000 description 6
- 238000009833 condensation Methods 0.000 description 6
- 230000005494 condensation Effects 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 238000003756 stirring Methods 0.000 description 6
- CWERGRDVMFNCDR-UHFFFAOYSA-N thioglycolic acid Chemical compound OC(=O)CS CWERGRDVMFNCDR-UHFFFAOYSA-N 0.000 description 6
- QXNVGIXVLWOKEQ-UHFFFAOYSA-N Disodium Chemical class [Na][Na] QXNVGIXVLWOKEQ-UHFFFAOYSA-N 0.000 description 5
- 229920001522 polyglycol ester Polymers 0.000 description 5
- 239000000047 product Substances 0.000 description 5
- 239000004615 ingredient Substances 0.000 description 4
- 159000000000 sodium salts Chemical class 0.000 description 4
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
- WRIDQFICGBMAFQ-UHFFFAOYSA-N (E)-8-Octadecenoic acid Natural products CCCCCCCCCC=CCCCCCCC(O)=O WRIDQFICGBMAFQ-UHFFFAOYSA-N 0.000 description 3
- HYZJCKYKOHLVJF-UHFFFAOYSA-N 1H-benzimidazole Chemical compound C1=CC=C2NC=NC2=C1 HYZJCKYKOHLVJF-UHFFFAOYSA-N 0.000 description 3
- PWVUXRBUUYZMKM-UHFFFAOYSA-N 2-(2-hydroxyethoxy)ethyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCCOCCO PWVUXRBUUYZMKM-UHFFFAOYSA-N 0.000 description 3
- LQJBNNIYVWPHFW-UHFFFAOYSA-N 20:1omega9c fatty acid Natural products CCCCCCCCCCC=CCCCCCCCC(O)=O LQJBNNIYVWPHFW-UHFFFAOYSA-N 0.000 description 3
- QSBYPNXLFMSGKH-UHFFFAOYSA-N 9-Heptadecensaeure Natural products CCCCCCCC=CCCCCCCCC(O)=O QSBYPNXLFMSGKH-UHFFFAOYSA-N 0.000 description 3
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 3
- 239000005642 Oleic acid Substances 0.000 description 3
- ZQPPMHVWECSIRJ-UHFFFAOYSA-N Oleic acid Natural products CCCCCCCCC=CCCCCCCCC(O)=O ZQPPMHVWECSIRJ-UHFFFAOYSA-N 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 125000002883 imidazolyl group Chemical group 0.000 description 3
- QXJSBBXBKPUZAA-UHFFFAOYSA-N isooleic acid Natural products CCCCCCCC=CCCCCCCCCC(O)=O QXJSBBXBKPUZAA-UHFFFAOYSA-N 0.000 description 3
- JHOKTNSTUVKGJC-UHFFFAOYSA-N n-(hydroxymethyl)octadecanamide Chemical compound CCCCCCCCCCCCCCCCCC(=O)NCO JHOKTNSTUVKGJC-UHFFFAOYSA-N 0.000 description 3
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 3
- 235000008733 Citrus aurantifolia Nutrition 0.000 description 2
- 235000011941 Tilia x europaea Nutrition 0.000 description 2
- 150000007513 acids Chemical class 0.000 description 2
- 125000003277 amino group Chemical group 0.000 description 2
- 150000001721 carbon Chemical group 0.000 description 2
- HDFRDWFLWVCOGP-UHFFFAOYSA-N carbonothioic O,S-acid Chemical compound OC(S)=O HDFRDWFLWVCOGP-UHFFFAOYSA-N 0.000 description 2
- 239000002270 dispersing agent Substances 0.000 description 2
- 239000002657 fibrous material Substances 0.000 description 2
- 150000002334 glycols Chemical class 0.000 description 2
- 239000004571 lime Substances 0.000 description 2
- 238000000034 method Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 239000004627 regenerated cellulose Substances 0.000 description 2
- 238000006277 sulfonation reaction Methods 0.000 description 2
- OGNVQLDIPUXYDH-ZPKKHLQPSA-N (2R,3R,4S)-3-(2-methylpropanoylamino)-4-(4-phenyltriazol-1-yl)-2-[(1R,2R)-1,2,3-trihydroxypropyl]-3,4-dihydro-2H-pyran-6-carboxylic acid Chemical compound CC(C)C(=O)N[C@H]1[C@H]([C@H](O)[C@H](O)CO)OC(C(O)=O)=C[C@@H]1N1N=NC(C=2C=CC=CC=2)=C1 OGNVQLDIPUXYDH-ZPKKHLQPSA-N 0.000 description 1
- HDCGBWBATVAIRI-UHFFFAOYSA-N 5-heptadecyl-1h-benzimidazole-2,4-disulfonic acid Chemical compound CCCCCCCCCCCCCCCCCC1=CC=C2N=C(S(O)(=O)=O)NC2=C1S(O)(=O)=O HDCGBWBATVAIRI-UHFFFAOYSA-N 0.000 description 1
- QTBSBXVTEAMEQO-UHFFFAOYSA-M Acetate Chemical compound CC([O-])=O QTBSBXVTEAMEQO-UHFFFAOYSA-M 0.000 description 1
- 229920002955 Art silk Polymers 0.000 description 1
- 239000004215 Carbon black (E152) Substances 0.000 description 1
- 229920000742 Cotton Polymers 0.000 description 1
- HJEINPVZRDJRBY-UHFFFAOYSA-N Disul Chemical compound OS(=O)(=O)OCCOC1=CC=C(Cl)C=C1Cl HJEINPVZRDJRBY-UHFFFAOYSA-N 0.000 description 1
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 1
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 1
- 239000004952 Polyamide Substances 0.000 description 1
- VMHLLURERBWHNL-UHFFFAOYSA-M Sodium acetate Chemical compound [Na+].CC([O-])=O VMHLLURERBWHNL-UHFFFAOYSA-M 0.000 description 1
- 125000002252 acyl group Chemical group 0.000 description 1
- 125000002947 alkylene group Chemical group 0.000 description 1
- 229920002678 cellulose Polymers 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 230000000875 corresponding effect Effects 0.000 description 1
- 238000001035 drying Methods 0.000 description 1
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 1
- 229930195733 hydrocarbon Natural products 0.000 description 1
- 229910052739 hydrogen Inorganic materials 0.000 description 1
- 239000001257 hydrogen Substances 0.000 description 1
- 239000010985 leather Substances 0.000 description 1
- 238000002844 melting Methods 0.000 description 1
- 230000008018 melting Effects 0.000 description 1
- 229920002647 polyamide Polymers 0.000 description 1
- 229920000151 polyglycol Polymers 0.000 description 1
- 239000010695 polyglycol Substances 0.000 description 1
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 1
- 229910052708 sodium Inorganic materials 0.000 description 1
- 239000011734 sodium Substances 0.000 description 1
- 235000017281 sodium acetate Nutrition 0.000 description 1
- 239000001632 sodium acetate Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003460 sulfonic acids Chemical class 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
Classifications
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/256—Sulfonated compounds esters thereof, e.g. sultones
-
- 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
- D06M13/02—Treating fibres, threads, yarns, fabrics or fibrous goods made from such materials, with non-macromolecular organic compounds; Such treatment combined with mechanical treatment with hydrocarbons
-
- 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
- D06M13/10—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 oxygen
- D06M13/224—Esters of carboxylic acids; Esters of carbonic acid
-
- 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
- D06M13/244—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 sulfur or phosphorus
- D06M13/248—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 sulfur or phosphorus with compounds containing sulfur
- D06M13/252—Mercaptans, thiophenols, sulfides or polysulfides, e.g. mercapto acetic acid; Sulfonium compounds
Definitions
- a dispersing agent 5 H a water-soluble salt of a condensation product of an N-methylolamide of a higher fatty acid I with a mercapto-carboxylic acid and, if desired, N H a lime-resistant sulfonation product of a, benzimidazole having attached to the a carbon atom a side-chain of at least 12
- esters R of ethylene glycol, diethylene glycol, triethylene 15 glycol or even higher polyglycols with fatty acids is the acyl radical of the fatty acid employed in of high molecular weight, especially fatty acids the condensation. Products of these const tutions containing at least 12 carbon atoms. Polyare described in U. S. Patent No. 2,337,220.
- glycols as mentioned above correspond to the These examples demonstrate that an acylated formula amino group corresponds to the formula HO (CH2-CH2O) r-CHz-CHPOH %0 wherein a: is at least one.
- condensation products of N-methylolamides of higher fatty acids with mercapto-carboxylic l acids there may be used, for example, condensation products of the formula wherein z CHr-S R c is an acyl radical of a carboxylic acid and R1 is w e 1 is a amino D acylated With a f y hydrogen or a hydrocarbon radical, for instance, acid with at least 16 carbon atoms and R is an alkyl radical which may be substituted; R1 alkylene.
- condensation products of may be, for inst nce, methyl, ethyl or a methyl this kind are, for instance, the condensation prodradical substituted by an acylated amino group.
- the dispersions used in the invention may conin which tain, for example, the following products: Sulfonic acids of benzimidazoles having attached to the -carbon atom a side chain of at least 12 carbon atoms, which benzimidazoles may, if desired, be aralkylated, for example, the sodium is the acyl residue of the fatty acid used.
- Ex- Salt of 1-,L-heptadecyl-benzimida l 1- amples of condensation products with the aforeulfoni acid.
- the partial esters of higher fatty 0 acids and a glycol may be introduced, advantageously in the molten state in the case of comy pounds which are solid at room temperature, into concentrated solutions or pastes of the above or ⁇ mentioned dispersing agents while rapidly stiract aces ring, advantageously at a temperature above the melting point of the substance to be dispersed.
- compositions of matter producing a softening eiiect on textiles which compositions of matter comprise an aqueous dispersion of a partial ester of a higher fatty acid and a glycol, said dispersion containing a water-soluble salt of a condensation product of an N-methylolamide of a higher fatty acid with a mercapto-carboxylic acid.
- the softening process of the invention may be carried out by impregnating the material at room temperature or a moderately raised temperature with an aqueous liquor containing a small quantity of a dispersion of the kind described above, for example, i to grams per liter, and then Squeezing or centrifuging the material and drying it.
- Example 1 Chlorinated wool is softened in the following manner:
- a bath which contains, per liter, 1 gram of a mixture of 25 parts of diethylene glycol monostearate. 14 parts of the sodium salt of a. carboxylic acid obtainable by the condensation of stearic acid-N-methylolamide with thioglycollic acid and also 11 parts of the disodium salt of N benzvl- -hepta decyl-benzimid azole disul onic acid.
- the wool is worked in the bath at a liquor ratio of 1:10 for /4 hour at room temperature and centrifuged and dried. The wool so obtained is distinctly softer than the untreated material.
- the dispersion used above is prepared in the following manner:
- T68 parts of the sodium salt of the carboxylic acid obtainable by condensing stearic acid-N- methylolamide with thioglycollic acid, and '72 parts of the disodium salt of N-benzyl- -heotadecyl-benzimidazole disulfonic acid are added in portions while stirring to 100 parts by volume of water at 95 C. Then a further 60 parts of the disodium salt of N-benzylr-heotadecvl-benzimidazole disulfonic acid are introduced while stirring, advantageously with the introduction of steam heated to 100 C. In the course of about 30 minutes 300 parts of diethylene-glycol monostearate heated at 90 C.
- the condensation product of stearic acid-N- methylolamide and thioglycollic acid as used above corresponds to the formula ZCHzS-CHz-C and is obtained by condensing one molecular proportion of the methylolamide of commercial stearic acid with A9, molecular proportion of thioglycolllc acid.
- a similar efiect can be obtained by using, instead of diethylene glycol monostearate, the cor responding oleic acid ester and in other respects working exactly in the manner described above.
- the wool is worked in the bath at a liquor ratio of 1:10 for /4 hour at room temperature and centrifuged and dried. The wool so obtained is distinctly softer than the untreated material.
- the stearic acid polyglycol ester used above can be obtained by forcing 247.5 parts of ethylene oxide under a, pressure of 6 to 10 atmospheres at l50-l55 C. into 400 parts of commercial stearic acid and 15.1 parts of finely ground sodium acetate.
- the dispersion used above may be prepared as follows: 525 parts of the sodium salt of the carboxylic acid obtainable by the condensation of stearlc acid N-methylolamide with thio-glycollic acid and 225 parts of the disodium salt of N- benzyl ,u heptadecyl benzimidazole disulfonic acid are heated at the boil with 3'75 parts of water, while stirring. In this manner a homogeneous paste is obtained. 750 parts of the above described stearic acid polyglycol ester heated to C. are then introduced in small portions in the course of 30 minutes while rapidly stirring. The resulting homogeneous paste is stirred cold and made up to a weight of 3000 parts by the addition of water.
- composition of matter producing a softening efiect on textiles consisting of an aqueous dispersion of a partial ester of a fatty acid with at least 12 carbonatoms and a glycol, said dispersion containing a water-soluble salt of a carboxylic acid of the formula wherein R'CO is the acyl radical of a fatty acid with at least 16 carbon atoms, said dispersion containing'also a water-soluble salt of a sulfonated benzimidazole in which the ,u-carbon atom of the imidazole ring is bound to an alkyl radical of at least 12 carbon atoms, the relative proportions of the ingredients being about 50 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the carboxylic acid and 15-22 parts by weight of the water-soluble salt oikthe sulfonated benzimidazole; 1
- composition of matter producing a softening effect on textiles consisting of an aqueous dispersion of a partial ester of a fatty acid with at least 12 carbon atoms and a glycol ether of the formula wherein m is at least one, said dispersion containing a water-soluble salt of a carboxylic acid of the formula wherein R'-CO- is the acyl radical of a fatty acid with at least 16 carbon atoms, said dispersion containing also a water-soluble salt of a sulfonated benzimidazole in which the -carbon atom of the imidazole ring is bound to an alkyl radical of at least 12 carbon atoms, the relative proportions of the ingredients being about 60 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the-carboxylic acid and 15-22 parts by weight of the watersoluble salt of the sulfonated benzimidazole.
- composition of matter producing a softening effect on textiles consistin of an aqueous dispersion of an ester of the formula wherein R-CO- is the acyl radical of commercial stearic acid, said dispersion containing a water-soluble salt of the carboxylic acid of the formula wherein R'C0- is the acyl radical of commercial stearic acid, this carboxylic acid being obtained by condensing 1 molecular proportion of the methylol amide of commercial stearic acid with molecular proportion of thioglycollic acid, said dispersion containing also a water-soluble salt of a disulfonic acid of the benzimidazole of the formula wherein R is the alkyl radical contained in commercial stearic acid of the formula the relative proportions of the ingredients being about 50 parts by weight of the ester to 28-35 parts by weight of the water-soluble salt of the carboxylic acid and 15-22 parts by weight of the water-soluble salt of the sulfonated benzimidazo
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| CH653674X | 1946-06-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2576896A true US2576896A (en) | 1951-11-27 |
Family
ID=4526320
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US755709A Expired - Lifetime US2576896A (en) | 1946-06-28 | 1947-06-19 | Compositions of matter for producing a softening effect on textiles |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US2576896A (en, 2012) |
| BE (1) | BE474161A (en, 2012) |
| CH (2) | CH268510A (en, 2012) |
| FR (1) | FR948595A (en, 2012) |
| GB (2) | GB653732A (en, 2012) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322802A (en) * | 1963-05-27 | 1967-05-30 | Vanderbilt Co R T | Metal salts of organodithiocarbamateorganothiocarbamoyl sulfinates and the preparation thereof |
| CN113089309A (zh) * | 2021-03-27 | 2021-07-09 | 安徽省伊贝雅纺织有限公司 | 一种毛巾的处理工艺 |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1058968B (de) * | 1954-03-10 | 1959-06-11 | Stockhausen & Cie Chem Fab | Verfahren zum Avivieren bzw. Weichmachen von vollsynthetischen Garnen, Spinnfasern, Folien und textilen Flaechengebilden |
| DE1056576B (de) * | 1954-03-12 | 1959-05-06 | Glanzstoff Ag | Verfahren zum Avivieren bzw. Weichmachen von vollsynthetischen Garnen, Spinnfasern, Folien und textilen Flaechengebilden |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US1985687A (en) * | 1929-11-18 | 1934-12-25 | Ig Farbenindustrie Ag | Oiling and dressing fibers |
| US2036525A (en) * | 1932-04-27 | 1936-04-07 | Soc Of Chemical Ind | Imidazole sulphonic acids useful as textile assisting agents and process of making same |
| US2043164A (en) * | 1936-06-02 | Basic imedazole compounds which are | ||
| US2245412A (en) * | 1937-09-30 | 1941-06-10 | Eastman Kodak Co | Yarn treating composition and process |
| US2337220A (en) * | 1938-08-11 | 1943-12-21 | Chem Ind Basel | Condensation products and process of preparing same |
| US2345632A (en) * | 1939-05-20 | 1944-04-04 | Nat Oil Prod Co | Polyamides |
-
0
- BE BE474161D patent/BE474161A/xx unknown
-
1946
- 1946-06-28 CH CH268510D patent/CH268510A/de unknown
-
1947
- 1947-05-07 CH CH272747D patent/CH272747A/de unknown
- 1947-06-19 US US755709A patent/US2576896A/en not_active Expired - Lifetime
- 1947-06-20 GB GB26185/50A patent/GB653732A/en not_active Expired
- 1947-06-20 GB GB16348/47A patent/GB653674A/en not_active Expired
- 1947-06-27 FR FR948595D patent/FR948595A/fr not_active Expired
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2043164A (en) * | 1936-06-02 | Basic imedazole compounds which are | ||
| US1985687A (en) * | 1929-11-18 | 1934-12-25 | Ig Farbenindustrie Ag | Oiling and dressing fibers |
| US2036525A (en) * | 1932-04-27 | 1936-04-07 | Soc Of Chemical Ind | Imidazole sulphonic acids useful as textile assisting agents and process of making same |
| US2245412A (en) * | 1937-09-30 | 1941-06-10 | Eastman Kodak Co | Yarn treating composition and process |
| US2337220A (en) * | 1938-08-11 | 1943-12-21 | Chem Ind Basel | Condensation products and process of preparing same |
| US2345632A (en) * | 1939-05-20 | 1944-04-04 | Nat Oil Prod Co | Polyamides |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3322802A (en) * | 1963-05-27 | 1967-05-30 | Vanderbilt Co R T | Metal salts of organodithiocarbamateorganothiocarbamoyl sulfinates and the preparation thereof |
| CN113089309A (zh) * | 2021-03-27 | 2021-07-09 | 安徽省伊贝雅纺织有限公司 | 一种毛巾的处理工艺 |
Also Published As
| Publication number | Publication date |
|---|---|
| BE474161A (en, 2012) | |
| GB653674A (en) | 1951-05-23 |
| GB653732A (en) | 1951-05-23 |
| CH268510A (de) | 1950-05-31 |
| FR948595A (fr) | 1949-08-04 |
| CH272747A (de) | 1950-12-31 |
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