US2213360A - Chemical process and composition - Google Patents
Chemical process and composition Download PDFInfo
- Publication number
- US2213360A US2213360A US2213360DA US2213360A US 2213360 A US2213360 A US 2213360A US 2213360D A US2213360D A US 2213360DA US 2213360 A US2213360 A US 2213360A
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- United States
- Prior art keywords
- gaseous
- chlorine
- sulfur dioxide
- textile
- hydrolyzing
- Prior art date
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- 239000000203 mixture Substances 0.000 title description 18
- 238000001311 chemical methods and process Methods 0.000 title 2
- RAHZWNYVWXNFOC-UHFFFAOYSA-N sulphur dioxide Chemical compound O=S=O RAHZWNYVWXNFOC-UHFFFAOYSA-N 0.000 description 76
- 239000004753 textile Substances 0.000 description 48
- 239000000047 product Substances 0.000 description 42
- 235000017168 chlorine Nutrition 0.000 description 36
- 239000004215 Carbon black (E152) Substances 0.000 description 34
- 239000000460 chlorine Substances 0.000 description 34
- 229910052801 chlorine Inorganic materials 0.000 description 34
- ZAMOUSCENKQFHK-UHFFFAOYSA-N chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 description 34
- 150000002430 hydrocarbons Chemical class 0.000 description 32
- 230000003301 hydrolyzing Effects 0.000 description 30
- 239000000243 solution Substances 0.000 description 30
- 239000000463 material Substances 0.000 description 26
- 238000000034 method Methods 0.000 description 26
- 150000001412 amines Chemical class 0.000 description 24
- 239000000835 fiber Substances 0.000 description 24
- 239000001993 wax Substances 0.000 description 24
- 239000011780 sodium chloride Substances 0.000 description 20
- -1 amine salts Chemical class 0.000 description 18
- 239000007864 aqueous solution Substances 0.000 description 18
- 239000004744 fabric Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 14
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 14
- 239000012188 paraffin wax Substances 0.000 description 14
- 239000000344 soap Substances 0.000 description 14
- 150000003973 alkyl amines Chemical class 0.000 description 12
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 12
- 238000006243 chemical reaction Methods 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 230000005591 charge neutralization Effects 0.000 description 8
- 238000006460 hydrolysis reaction Methods 0.000 description 8
- 230000001264 neutralization Effects 0.000 description 8
- 238000006386 neutralization reaction Methods 0.000 description 8
- 235000019271 petrolatum Nutrition 0.000 description 8
- 150000003839 salts Chemical class 0.000 description 8
- 239000004264 Petrolatum Substances 0.000 description 6
- 229940066842 Petrolatum Drugs 0.000 description 6
- 238000002360 preparation method Methods 0.000 description 6
- PAFZNILMFXTMIY-UHFFFAOYSA-N Cyclohexylamine Chemical compound NC1CCCCC1 PAFZNILMFXTMIY-UHFFFAOYSA-N 0.000 description 4
- DIOQZVSQGTUSAI-UHFFFAOYSA-N Decane Chemical compound CCCCCCCCCC DIOQZVSQGTUSAI-UHFFFAOYSA-N 0.000 description 4
- SNRUBQQJIBEYMU-UHFFFAOYSA-N Dodecane Chemical compound CCCCCCCCCCCC SNRUBQQJIBEYMU-UHFFFAOYSA-N 0.000 description 4
- BKIMMITUMNQMOS-UHFFFAOYSA-N Nonane Chemical compound CCCCCCCCC BKIMMITUMNQMOS-UHFFFAOYSA-N 0.000 description 4
- RZJRJXONCZWCBN-UHFFFAOYSA-N Octadecane Chemical compound CCCCCCCCCCCCCCCCCC RZJRJXONCZWCBN-UHFFFAOYSA-N 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- 239000004902 Softening Agent Substances 0.000 description 4
- 229920002472 Starch Polymers 0.000 description 4
- POOSGDOYLQNASK-UHFFFAOYSA-N Tetracosane Chemical compound CCCCCCCCCCCCCCCCCCCCCCCC POOSGDOYLQNASK-UHFFFAOYSA-N 0.000 description 4
- 125000001931 aliphatic group Chemical group 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 239000007795 chemical reaction product Substances 0.000 description 4
- OSVXSBDYLRYLIG-UHFFFAOYSA-N chlorine dioxide Inorganic materials O=Cl=O OSVXSBDYLRYLIG-UHFFFAOYSA-N 0.000 description 4
- ROSDSFDQCJNGOL-UHFFFAOYSA-N dimethylamine Chemical compound CNC ROSDSFDQCJNGOL-UHFFFAOYSA-N 0.000 description 4
- 239000007789 gas Substances 0.000 description 4
- 239000008246 gaseous mixture Substances 0.000 description 4
- 230000001771 impaired Effects 0.000 description 4
- 230000001050 lubricating Effects 0.000 description 4
- 239000003960 organic solvent Substances 0.000 description 4
- 235000019698 starch Nutrition 0.000 description 4
- 229910052717 sulfur Inorganic materials 0.000 description 4
- LZDKZFUFMNSQCJ-UHFFFAOYSA-N 1,2-diethoxyethane Chemical compound CCOCCOCC LZDKZFUFMNSQCJ-UHFFFAOYSA-N 0.000 description 2
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- NJBCRXCAPCODGX-UHFFFAOYSA-N 2-methyl-N-(2-methylpropyl)propan-1-amine Chemical compound CC(C)CNCC(C)C NJBCRXCAPCODGX-UHFFFAOYSA-N 0.000 description 2
- 229920003043 Cellulose fiber Polymers 0.000 description 2
- 229920001353 Dextrin Polymers 0.000 description 2
- 239000004375 Dextrin Substances 0.000 description 2
- JQVDAXLFBXTEQA-UHFFFAOYSA-N Dibutylamine Chemical compound CCCCNCCCC JQVDAXLFBXTEQA-UHFFFAOYSA-N 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N Diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- UAOMVDZJSHZZME-UHFFFAOYSA-N Diisopropylamine Chemical compound CC(C)NC(C)C UAOMVDZJSHZZME-UHFFFAOYSA-N 0.000 description 2
- 102000004190 Enzymes Human genes 0.000 description 2
- 108090000790 Enzymes Proteins 0.000 description 2
- 108010010803 Gelatin Proteins 0.000 description 2
- 229940093912 Gynecological Sulfonamides Drugs 0.000 description 2
- 229920002456 HOTAIR Polymers 0.000 description 2
- HQABUPZFAYXKJW-UHFFFAOYSA-N N-Butylamine Chemical compound CCCCN HQABUPZFAYXKJW-UHFFFAOYSA-N 0.000 description 2
- TVMXDCGIABBOFY-UHFFFAOYSA-N Octane Chemical compound CCCCCCCC TVMXDCGIABBOFY-UHFFFAOYSA-N 0.000 description 2
- DPBLXKKOBLCELK-UHFFFAOYSA-N Pentylamine Chemical compound CCCCCN DPBLXKKOBLCELK-UHFFFAOYSA-N 0.000 description 2
- YBBRCQOCSYXUOC-UHFFFAOYSA-N Sulfuryl chloride Chemical class ClS(Cl)(=O)=O YBBRCQOCSYXUOC-UHFFFAOYSA-N 0.000 description 2
- GETQZCLCWQTVFV-UHFFFAOYSA-N Trimethylamine Chemical compound CN(C)C GETQZCLCWQTVFV-UHFFFAOYSA-N 0.000 description 2
- 241000282485 Vulpes vulpes Species 0.000 description 2
- 239000002253 acid Substances 0.000 description 2
- 150000001298 alcohols Chemical class 0.000 description 2
- 238000010640 amide synthesis reaction Methods 0.000 description 2
- 125000004429 atoms Chemical group 0.000 description 2
- 238000007664 blowing Methods 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 230000005587 bubbling Effects 0.000 description 2
- 229910052799 carbon Inorganic materials 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000004432 carbon atoms Chemical group C* 0.000 description 2
- 235000019398 chlorine dioxide Nutrition 0.000 description 2
- 125000001309 chloro group Chemical group Cl* 0.000 description 2
- 239000004927 clay Substances 0.000 description 2
- 229910052570 clay Inorganic materials 0.000 description 2
- 239000007859 condensation product Substances 0.000 description 2
- 235000019425 dextrin Nutrition 0.000 description 2
- 239000003085 diluting agent Substances 0.000 description 2
- XTHFKEDIFFGKHM-UHFFFAOYSA-N dimethoxyethane Chemical class COCCOC XTHFKEDIFFGKHM-UHFFFAOYSA-N 0.000 description 2
- 238000002845 discoloration Methods 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 150000002148 esters Chemical class 0.000 description 2
- 150000002169 ethanolamines Chemical class 0.000 description 2
- 150000002170 ethers Chemical class 0.000 description 2
- 125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
- 150000003947 ethylamines Chemical group 0.000 description 2
- 238000009963 fulling Methods 0.000 description 2
- 229920000159 gelatin Polymers 0.000 description 2
- 239000008273 gelatin Substances 0.000 description 2
- 235000019322 gelatine Nutrition 0.000 description 2
- 235000011852 gelatine desserts Nutrition 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 125000000623 heterocyclic group Chemical group 0.000 description 2
- 150000002440 hydroxy compounds Chemical class 0.000 description 2
- 229940079867 intestinal antiinfectives Sulfonamides Drugs 0.000 description 2
- 239000007788 liquid Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002844 melting Methods 0.000 description 2
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 2
- 230000003472 neutralizing Effects 0.000 description 2
- QJGQUHMNIGDVPM-UHFFFAOYSA-N nitrogen group Chemical group [N] QJGQUHMNIGDVPM-UHFFFAOYSA-N 0.000 description 2
- 229940038384 octadecane Drugs 0.000 description 2
- 229940005938 ophthalmologic antiinfectives Sulfonamides Drugs 0.000 description 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 description 2
- NQRYJNQNLNOLGT-UHFFFAOYSA-N piperidine Chemical compound C1CCNCC1 NQRYJNQNLNOLGT-UHFFFAOYSA-N 0.000 description 2
- 125000001436 propyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])[H] 0.000 description 2
- 239000012429 reaction media Substances 0.000 description 2
- 238000004513 sizing Methods 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 238000009987 spinning Methods 0.000 description 2
- 239000008107 starch Substances 0.000 description 2
- 230000003068 static Effects 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- 150000003456 sulfonamides Chemical class 0.000 description 2
- LSNNMFCWUKXFEE-UHFFFAOYSA-N sulfonic acid Chemical compound OS(O)=O LSNNMFCWUKXFEE-UHFFFAOYSA-N 0.000 description 2
- NINIDFKCEFEMDL-UHFFFAOYSA-N sulfur Chemical compound [S] NINIDFKCEFEMDL-UHFFFAOYSA-N 0.000 description 2
- 239000011593 sulfur Substances 0.000 description 2
- 229920002994 synthetic fiber Polymers 0.000 description 2
- 239000012209 synthetic fiber Substances 0.000 description 2
- 239000006188 syrup Substances 0.000 description 2
- 235000020357 syrup Nutrition 0.000 description 2
- 239000000454 talc Substances 0.000 description 2
- 229910052623 talc Inorganic materials 0.000 description 2
- 235000012222 talc Nutrition 0.000 description 2
- 229940026752 topical Sulfonamides Drugs 0.000 description 2
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
- D06M13/10—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
Definitions
- This invention relates to the preparation of textile treating agents and to processes for the treatment of textiles. More particularly, it relates to the finishing of textile materials includ- 6 ing filaments, fibers, threads, skeins, 'yarns and fabrics; Still more particularly, it relates to the finishing and softening of textile fibers,'threads and fabrics.
- the invention also relates to treating solutions. 10
- This invention has for an object to improve the art of finishing and softening textile materials.
- a further object is to produce new and effective textile treating agents.
- a further object is to treat natural and synthetic fibers, particularly cellulosic fibers, including thechemically modified cellulose fibers so that they will be soft and smooth to the touch.
- a still further object is to prepare soft, smooth, cellulosic fibers and fabrics which are free from objec- 2 tionable odor and. do not become rancid.
- a still further object is to soften and finishcellulosic fibers in such a manner that their strength will not be impaired.
- a still further object is to soften and finish synthetic and natural textile fibers and fabrics in such a manner that their solubility. characteristics are not increased. Other objects will appear hereinafter.
- An important embodiment of the invention resides in an efficient method of making amine salts, which are new compounds and compositions.
- This method comprises dissolving the initial reaction product resulting from treat- .ment with sulfur dioxide and chlorine which is a complex mixture containing hydrocarbon sulfonyl chlorides, chlorhydrocarbon sulfonyl chlorides, hydrocarbon polysulfonyl chlorides, and chlorhydrocarbon polysulfonyl chlorides in a water-soluble organic solvent, especially an ali-. phatic monohydric or polyhydric alcohol and u bubbling a gaseous or readily volatile. amine,
- amine salts represent 5 the preferred embodiment of this invention.
- -fabrics, etc., either synthetic or cellulosic are treated with aqueous solutions containing small amounts of the above compounds, they become 20 soft and smooth to the touch, free from odor and color and their strength is not impaired.
- the resulting fibers are softened to a marked degree. They are not only smooth andsoft, but are fuller, more pliable 25 and in general more pleasing to the touch.
- the compounds are usually employed in the form .of a treating solution which is preferably They may be employed over a wide range of concentration.- From 0.001% to 5.0% 30 byweight of the solution represents a practical range.
- the amine salts even when used in con- .centrations on, the order of 0.001% to 0.5% by weight of the aqueous liquid give excellent softening and finishing results. 35-
- the weight of the above dimethylamine salt of Asiatic wax sulfonic acid and dried in hot air It has a very smooth surface and is more pliable than before the treatment.
- Other cottonfabrics such as muslins, sheetings, percales, twills, drills, etc., may be processed in a similar manner with baths containing from 0.1 to 0.5% of the softening agent to give them an enhanced feel when handled.
- the product may be used in containing stiffening and weighting china clay, etc., for sizing textile fabrics, wherein the product serves to lubricate and soften the effect of the stiffening and weighting agent's giving the fabric a more desirable finish.
- the product may also be applied to textile fibers in the staple form before spinning to improvetheir processing characteristics and to yarns of staple and. continuous filament fibers to lubricate them andimprove their processing characteristics.
- Example II Five hundred grams of parafiin wax (commercial "parawax) was melted and. a gaseous mixture of chlorine and sulfur dioxide in equimolecular proportions was passed in. at 85 to 100 with an incandescent light under-the flask. After 7 hours the gain inweight was 409 g. and on blowing with air, 4 g. of dissolved gases was blown out. The total chlorine passed through the reaction mass was 911 g. and the total sulfur dioxide was 1483 g. One hundred grams of the resulting product containing 23.03% C1 and 11.19% S was suspended in. 200 cc. (95%) alcohol and trimethylamine. passed in.
- amines disclosed in the I preceding examples may be substituted any aliphatic, aromatic, heterocyclic, aryl substituted aliphatic or mixed amines.
- suitable amines mention is made of Z-methyl piperidine, l-ethyl piperidine, l-n-butyl piperidine, n-butylamine, di-n-butylamine, cyclohexylamine, n-amylamine, di-isobutylamine, di-isopropylamine, piperidine, etc.
- any non-gaseous hydrocarbon preferably saturated hydrocarbon, e. g. pentane, octane, nonane, decane, dodecane, octadecane,.tetracosane, parai'fin wax, scale wax, petrolatum wax, etc.
- the neutralized products or salts having a short chain length are particularly useful as printing, mercerizing, etc., assistants.
- the products which have a chain length of 12 to 18 carbon 'atoms are particularly useful in conjunction with enzymes for starch removal, whereas those of longer chains such as the products obtained from wax distillates, match wax, paraffin wax, scale wax, petrolatum, petrolatum wax, etc., are particularly useful as textile softening, lubricating, fulling, etc. agents.
- the temperatures are preferably kept below the boiling point of the .reaction medium. High temperatures may be used, however, but they tend to promote amide formation.
- Water-miscible organic solvents may be used during the hydrolysis or neutralization step to promote contact between the reaction mass and the hydrolyzing agents.
- solvents or diluents may be mentioned ethyl, propyl, methyl, etc., alcohols, dioxane, glycol, and its ethers and esters, e. g. ethylene glycol diethyl ether, ethylene glycol dimethyl ethers, etc.
- the hydroxy compounds mentioned are particularly useful when amines are used as the hydrolyzing and neutralizing agents.
- This invention possesses the advantage that fibers, etc. which are so treated are more acceptable to the trade. They are softer than untreated fibers and smooth to the touch and fuller. When white orbleached fabrics are so treated no discoloration obtains. The shade and light fastness of dyed materials is unchanged, which is surprising. The treatment also reduces static charges. This is more apparent at higher concentrations of the condensation product, but is noticeable with lesser amounts. These advantages are especially noticeable with viscose rayon both of the lustrous and delustered type.
- a process which comprises treating a'textile material with a solution of paraffin derivative soap obtained by reacting a non-gaseous paraifin hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting product with an organic nitrogenous base.
- a process which comprises finishing andp softening a textile material with a solution of a parafiln derivative soap obtained by reacting a non-gaseous paraffin hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting product with an organic amine base.
- a process which comprises treating a cellulosic material with an aqueous'solution of a parafiln derivative soap obtained by reacting a nongas'eous parafiin hydrocarbon with gaseous sulfur dioxide andchlorine, and hydrolyzing the resulting product with a lower alkyl-amine base.
- a process which comprises treating a textile material with a solution of a paraflin derivative soap obtainable by reacting a non-gaseous paraifln hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting prodnot with a concentrated aqueous solution of a lower alkyl amine base.
- a textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraffin derivative soapobtained by reacting a non-- gaseous paraflin hydrocarbon with gaseous sulfur dioxide and chlorine and hydrolyzing the resulting product with an organic amine base.
- a textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a parafiin derivative soap obtained by reacting a non-gaseous paraffin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of a lower alkyl amine.
- a textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraflin derivative soap obtained by reacting a non-gaseous paraifin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of an organic amine.
- a textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraffin derivative soap obtained by reacting a non gaseous parafiin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of a lower alkyl amine.
Landscapes
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Sept. 3, 1940 PATENT OFFICE,
cnnmcar. rnoosss AND COMPOSITION William S. Calcott and Arthur L; Fox, Woodstown, N. J., assignors to E. I. du Pont deiNemours & Company, Wilmington, Del, a corporation of Delaware No- Drawing.
-21 Claims.
This invention relates to the preparation of textile treating agents and to processes for the treatment of textiles. More particularly, it relates to the finishing of textile materials includ- 6 ing filaments, fibers, threads, skeins, 'yarns and fabrics; Still more particularly, it relates to the finishing and softening of textile fibers,'threads and fabrics. The invention also relates to treating solutions. 10 This invention has for an object to improve the art of finishing and softening textile materials. A further objectis to produce new and effective textile treating agents. A further object is to treat natural and synthetic fibers, particularly cellulosic fibers, including thechemically modified cellulose fibers so that they will be soft and smooth to the touch. A still further object is to prepare soft, smooth, cellulosic fibers and fabrics which are free from objec- 2 tionable odor and. do not become rancid. A still further object is to soften and finishcellulosic fibers in such a manner that their strength will not be impaired. A still further object is to soften and finish synthetic and natural textile fibers and fabrics in such a manner that their solubility. characteristics are not increased. Other objects will appear hereinafter.
The above and other objects are accomplished by" the preparation and use of certain salts of the products prepared by reacting a non-gaseous saturated hydrocarbon with gaseous 'sulfur dioxide and' chlorine and. hydrolyzing the-resulting products. The hydrolysis is preferably carried out under such conditions that neutralization of the-acidic groups is eifected. While the compositions and compounds having free acid groups have surface active properties and are useful in textile treating operations, the water soluble amine 40 salts are much more superior in such relations and in some instances give new and unexpected results. 1
An important embodiment of the invention resides in an efficient method of making amine salts, which are new compounds and compositions. This method comprises dissolving the initial reaction product resulting from treat- .ment with sulfur dioxide and chlorine which is a complex mixture containing hydrocarbon sulfonyl chlorides, chlorhydrocarbon sulfonyl chlorides, hydrocarbon polysulfonyl chlorides, and chlorhydrocarbon polysulfonyl chlorides in a water-soluble organic solvent, especially an ali-. phatic monohydric or polyhydric alcohol and u bubbling a gaseous or readily volatile. amine,
. aqueous.
Application January 11, 1939; Serial No. 250,454
e. g. mono-, diand trimethyl, ethyl and ethanol amines therethrough at a temperature below C. The reaction is continued until the hydrolysis and neutralization has gone to.completion or amines have greatly enhanced finishingand softening properties. The amine salts represent 5 the preferred embodiment of this invention.
It has been found that when fibers, yarns,
-fabrics, etc., ,either synthetic or cellulosic are treated with aqueous solutions containing small amounts of the above compounds, they become 20 soft and smooth to the touch, free from odor and color and their strength is not impaired. In the case of the amine salts the resulting fibers are softened to a marked degree. They are not only smooth andsoft, but are fuller, more pliable 25 and in general more pleasing to the touch.
The compounds are usually employed in the form .of a treating solution which is preferably They may be employed over a wide range of concentration.- From 0.001% to 5.0% 30 byweight of the solution represents a practical range. The amine salts even when used in con- .centrations on, the order of 0.001% to 0.5% by weight of the aqueous liquid give excellent softening and finishing results. 35-
The invention will be further illustrated, but is not intended to be limited by the following examples, in which the parts stated are parts by Five hundred grams Asiatic wax melting point 58-60 C. was placed in a three liter flask and 'a mixture of sulfur dioxide and chlorine passed in under the influence of'light and with stirring. The initial temperature was 128" due to heating the wax to melt it. The temperature gradually dropped to C. where it stayed due to the heat of reaction. After seven hours, the gain in weight was 450 g. The product is a very thick water- 5 white syrup, containing 25.8% .chlorines and 11.11% sulfur.
- One hundred grams of the above reaction product was mixed-with 200 cc. (95%) alcohol and dimethylamine gas was passed in keeping the 'baths agents, such as starches, dextrins, gelatin, talc,
weight of the above dimethylamine salt of Asiatic wax sulfonic acid and dried in hot air. It has a very smooth surface and is more pliable than before the treatment. Other cottonfabrics such as muslins, sheetings, percales, twills, drills, etc., may be processed in a similar manner with baths containing from 0.1 to 0.5% of the softening agent to give them an enhanced feel when handled. Similarly, the product may be used in containing stiffening and weighting china clay, etc., for sizing textile fabrics, wherein the product serves to lubricate and soften the effect of the stiffening and weighting agent's giving the fabric a more desirable finish. The product may also be applied to textile fibers in the staple form before spinning to improvetheir processing characteristics and to yarns of staple and. continuous filament fibers to lubricate them andimprove their processing characteristics.
Example II Five hundred grams of parafiin wax (commercial "parawax) was melted and. a gaseous mixture of chlorine and sulfur dioxide in equimolecular proportions was passed in. at 85 to 100 with an incandescent light under-the flask. After 7 hours the gain inweight was 409 g. and on blowing with air, 4 g. of dissolved gases was blown out. The total chlorine passed through the reaction mass was 911 g. and the total sulfur dioxide was 1483 g. One hundred grams of the resulting product containing 23.03% C1 and 11.19% S was suspended in. 200 cc. (95%) alcohol and trimethylamine. passed in. When complete solution had occurred, the mass was allowed to stand for 1 hour and then the alcohol evaporated under vacuum on a steam bath. The yield was 140 g. when evaluated as a'softening agent in a bath containing from 0.1 to 0.5% of the same, on viscose yarn, it showed softening surface lubricating properties.
In place of the specific amines disclosed in the I preceding examples may be substituted any aliphatic, aromatic, heterocyclic, aryl substituted aliphatic or mixed amines. As further examples of suitable amines, mention is made of Z-methyl piperidine, l-ethyl piperidine, l-n-butyl piperidine, n-butylamine, di-n-butylamine, cyclohexylamine, n-amylamine, di-isobutylamine, di-isopropylamine, piperidine, etc.
The initial commands or compositions set forth in the above examples are only representativeof many other compounds or compositions which could be used. Thus, the hydrolysis and neutralization products obtained by using a gaseous mixture of sulfur dioxide and chlorine according to the aforedescribed process with any non-gaseous hydrocarbon, preferably saturated hydrocarbon, e. g. pentane, octane, nonane, decane, dodecane, octadecane,.tetracosane, parai'fin wax, scale wax, petrolatum wax, etc., can be resorted to.
The neutralized products or salts having a short chain length, e. g. 5 to 10 carbon atoms, are particularly useful as printing, mercerizing, etc., assistants. The products which have a chain length of 12 to 18 carbon 'atoms are particularly useful in conjunction with enzymes for starch removal, whereas those of longer chains such as the products obtained from wax distillates, match wax, paraffin wax, scale wax, petrolatum, petrolatum wax, etc., are particularly useful as textile softening, lubricating, fulling, etc. agents.
In order to insure against the preparation of sulfonamides, some water must be present in' the reaction zone. This may be accomplished by the use of ordinary alcohol containing 4% or more of water. Even traces of water cause some salt to be formed.
The temperatures are preferably kept below the boiling point of the .reaction medium. High temperatures may be used, however, but they tend to promote amide formation.
Water-miscible organic solvents may be used during the hydrolysis or neutralization step to promote contact between the reaction mass and the hydrolyzing agents. As examples-of such solvents or diluents may be mentioned ethyl, propyl, methyl, etc., alcohols, dioxane, glycol, and its ethers and esters, e. g. ethylene glycol diethyl ether, ethylene glycol dimethyl ethers, etc. The hydroxy compounds mentioned are particularly useful when amines are used as the hydrolyzing and neutralizing agents.
This invention possesses the advantage that fibers, etc. which are so treated are more acceptable to the trade. They are softer than untreated fibers and smooth to the touch and fuller. When white orbleached fabrics are so treated no discoloration obtains. The shade and light fastness of dyed materials is unchanged, which is surprising. The treatment also reduces static charges. This is more apparent at higher concentrations of the condensation product, but is noticeable with lesser amounts. These advantages are especially noticeable with viscose rayon both of the lustrous and delustered type.
.As many apparently widely different embodiments of this invention may be made without departing from the spirit and scope thereof, it is to be understood that we do not limit ourselves to the specific embodiments thereof except as defined in the following claims.
We claim:
1. A process which comprises treating a'textile material with a solution of paraffin derivative soap obtained by reacting a non-gaseous paraifin hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting product with an organic nitrogenous base.
2. A process which comprises finishing andp softening a textile material with a solution of a parafiln derivative soap obtained by reacting a non-gaseous paraffin hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting product with an organic amine base.
3. A process which comprises treating a cellulosic material with an aqueous'solution of a parafiln derivative soap obtained by reacting a nongas'eous parafiin hydrocarbon with gaseous sulfur dioxide andchlorine, and hydrolyzing the resulting product with a lower alkyl-amine base.
4. A process which comprises treating a textile material with a solution of a paraflin derivative soap obtainable by reacting a non-gaseous paraifln hydrocarbon with gaseous sulfur dioxide and chlorine, and hydrolyzing the resulting prodnot with a concentrated aqueous solution of a lower alkyl amine base.
5. The process of treating a textile material which comprises padding the same with a solution containing an organic amine salt obtained by reacting a non-gaseous paraflin hydrocarbon with gaseous sulfur dioxide and gaseous chlorine and hydrolyzing the resulting product with an organic amine; and removing the excess solution.
6. A process as set forth in claim 5 wherein' the non-gaseous paraflin hydrocarbon is paraflin wax.
'7. The process of treating a textile material which comprises padding the same with a solu- -tion containing a lower alkyl amine salt obtained by reacting a non-gaseous paraffin hydrocarbon with gaseous sulfur dioxide and gase-.
ous chlorine and hydrolyzing the resulting prodnot with a lower alkylamine in the presence of water and a lower alcohol; and removing the' 10.- A textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraffin derivative soapobtained by reacting a non-- gaseous paraflin hydrocarbon with gaseous sulfur dioxide and chlorine and hydrolyzing the resulting product with an organic amine base.
11. A textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a parafiin derivative soap obtained by reacting a non-gaseous paraffin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of a lower alkyl amine.
12. A textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraflin derivative soap obtained by reacting a non-gaseous paraifin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of an organic amine.
13. A textile treating solution for the softening and finishing of textile materials comprising an aqueous solution containing a paraffin derivative soap obtained by reacting a non gaseous parafiin with sulfur dioxide and chlorine and hydrolyzing the resulting product with a concentrated aqueous solution of a lower alkyl amine.
14.' The process which comprises reacting a non-gaseous hydrocarbon with gaseous sulfur dioxide and chlorine and hydrolyzing the resulting product in the presence of an organic amine.
15. The process which comprises reacting a non-gaseous hydrocarbon with gaseous sulfur dioxide and chlorine and hydrolyzing the resulting product in the presence of a lower alkyl amine.
16. The process which comprises reacting a non-gaseous saturated hydrocarbon with gaseous sulfur dioxide and chlorine, adding a water soluble saturatedaliphatic alcohol and passing into the mixture a readily volatile aliphatic amine at a temperature below C.
17. The process which comprises reacting a. 3
non-gaseous saturated hydrocarbon with gaseous WILLIAM S. CALCO'I'I. ARTHUR L. FOX.
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2213360A true US2213360A (en) | 1940-09-03 |
Family
ID=3431446
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US2213360D Expired - Lifetime US2213360A (en) | Chemical process and composition |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2213360A (en) |
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471039A (en) * | 1940-02-21 | 1949-05-24 | Orthner Ludwig | Manufacture of improved fibrous materials and the materials thus obtained |
| DE836983C (en) * | 1949-07-14 | 1952-04-17 | Bayer Ag | laundry detergent |
| DE1014067B (en) * | 1953-07-29 | 1957-08-22 | Basf Ag | Wetting agent for mercerising and caustic baths |
| DE1058968B (en) * | 1954-03-10 | 1959-06-11 | Stockhausen & Cie Chem Fab | Process for the finishing or softening of fully synthetic yarns, staple fibers, foils and textile surfaces |
| US2956949A (en) * | 1955-10-19 | 1960-10-18 | Eastman Kodak Co | Fiber treating compositions |
| DE1151346B (en) * | 1958-03-27 | 1963-07-11 | Hoechst Ag | Waterproofing and fatliquoring agents for leather |
| US3217035A (en) * | 1961-09-07 | 1965-11-09 | Minnesota Mining & Mfg | Fluorinated polyols |
| US3321445A (en) * | 1961-09-07 | 1967-05-23 | Minnesota Mining & Mfg | Polymers of fluorine-containing sulfonamido polyols |
| US3979454A (en) * | 1974-03-29 | 1976-09-07 | Bayer Aktiengesellschaft | Process for the production of alkyl sulphonic acid hydroxy alkyl amides |
| WO2013070347A1 (en) | 2011-11-11 | 2013-05-16 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
| WO2013074155A1 (en) | 2011-11-15 | 2013-05-23 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
| US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
-
0
- US US2213360D patent/US2213360A/en not_active Expired - Lifetime
Cited By (14)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2471039A (en) * | 1940-02-21 | 1949-05-24 | Orthner Ludwig | Manufacture of improved fibrous materials and the materials thus obtained |
| DE836983C (en) * | 1949-07-14 | 1952-04-17 | Bayer Ag | laundry detergent |
| DE1014067B (en) * | 1953-07-29 | 1957-08-22 | Basf Ag | Wetting agent for mercerising and caustic baths |
| DE1058968B (en) * | 1954-03-10 | 1959-06-11 | Stockhausen & Cie Chem Fab | Process for the finishing or softening of fully synthetic yarns, staple fibers, foils and textile surfaces |
| US2956949A (en) * | 1955-10-19 | 1960-10-18 | Eastman Kodak Co | Fiber treating compositions |
| DE1151346B (en) * | 1958-03-27 | 1963-07-11 | Hoechst Ag | Waterproofing and fatliquoring agents for leather |
| US3217035A (en) * | 1961-09-07 | 1965-11-09 | Minnesota Mining & Mfg | Fluorinated polyols |
| US3321445A (en) * | 1961-09-07 | 1967-05-23 | Minnesota Mining & Mfg | Polymers of fluorine-containing sulfonamido polyols |
| US3979454A (en) * | 1974-03-29 | 1976-09-07 | Bayer Aktiengesellschaft | Process for the production of alkyl sulphonic acid hydroxy alkyl amides |
| US8969273B2 (en) | 2009-02-18 | 2015-03-03 | Chevron Oronite Company Llc | Lubricating oil compositions |
| US8841243B2 (en) | 2010-03-31 | 2014-09-23 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| US8796192B2 (en) | 2010-10-29 | 2014-08-05 | Chevron Oronite Company Llc | Natural gas engine lubricating oil compositions |
| WO2013070347A1 (en) | 2011-11-11 | 2013-05-16 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
| WO2013074155A1 (en) | 2011-11-15 | 2013-05-23 | Chevron Oronite Company Llc | Glycerol-containing functional fluid |
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