US2270658A - Treatment of textile materials - Google Patents
Treatment of textile materials Download PDFInfo
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- US2270658A US2270658A US240573A US24057338A US2270658A US 2270658 A US2270658 A US 2270658A US 240573 A US240573 A US 240573A US 24057338 A US24057338 A US 24057338A US 2270658 A US2270658 A US 2270658A
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- US
- United States
- Prior art keywords
- water
- emulsion
- treatment
- textile materials
- active
- 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
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- 239000000463 material Substances 0.000 title description 18
- 239000004753 textile Substances 0.000 title description 13
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 29
- 239000000839 emulsion Substances 0.000 description 16
- 239000003795 chemical substances by application Substances 0.000 description 12
- -1 pyridinium halides Chemical class 0.000 description 9
- 150000001875 compounds Chemical class 0.000 description 8
- 238000000034 method Methods 0.000 description 8
- 230000032050 esterification Effects 0.000 description 6
- 238000005886 esterification reaction Methods 0.000 description 6
- 239000005871 repellent Substances 0.000 description 6
- 150000008064 anhydrides Chemical class 0.000 description 5
- 239000000835 fiber Substances 0.000 description 5
- 238000010438 heat treatment Methods 0.000 description 5
- 230000002940 repellent Effects 0.000 description 5
- 238000007127 saponification reaction Methods 0.000 description 5
- 125000004432 carbon atom Chemical group C* 0.000 description 4
- 229920002678 cellulose Polymers 0.000 description 4
- 239000001913 cellulose Substances 0.000 description 4
- 239000004744 fabric Substances 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 238000009877 rendering Methods 0.000 description 4
- HYGPQBXMCSSRFZ-UHFFFAOYSA-N 2-octadecylpyridine;hydrochloride Chemical compound Cl.CCCCCCCCCCCCCCCCCCC1=CC=CC=N1 HYGPQBXMCSSRFZ-UHFFFAOYSA-N 0.000 description 3
- OBFSQMXGZIYMMN-UHFFFAOYSA-N 3-chloro-2-hexadecylpyridine Chemical compound CCCCCCCCCCCCCCCCC1=NC=CC=C1Cl OBFSQMXGZIYMMN-UHFFFAOYSA-N 0.000 description 3
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 3
- 150000008065 acid anhydrides Chemical class 0.000 description 3
- 235000014113 dietary fatty acids Nutrition 0.000 description 3
- 239000000194 fatty acid Substances 0.000 description 3
- 229930195729 fatty acid Natural products 0.000 description 3
- 150000004665 fatty acids Chemical class 0.000 description 3
- 239000010698 whale oil Substances 0.000 description 3
- 229920002955 Art silk Polymers 0.000 description 2
- 229920000742 Cotton Polymers 0.000 description 2
- CDBYLPFSWZWCQE-UHFFFAOYSA-L Sodium Carbonate Chemical compound [Na+].[Na+].[O-]C([O-])=O CDBYLPFSWZWCQE-UHFFFAOYSA-L 0.000 description 2
- 150000001408 amides Chemical class 0.000 description 2
- 239000005018 casein Substances 0.000 description 2
- BECPQYXYKAMYBN-UHFFFAOYSA-N casein, tech. Chemical compound NCCCCC(C(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(CC(C)C)N=C(O)C(CCC(O)=O)N=C(O)C(CC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(C(C)O)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=N)N=C(O)C(CCC(O)=O)N=C(O)C(CCC(O)=O)N=C(O)C(COP(O)(O)=O)N=C(O)C(CCC(O)=N)N=C(O)C(N)CC1=CC=CC=C1 BECPQYXYKAMYBN-UHFFFAOYSA-N 0.000 description 2
- 235000021240 caseins Nutrition 0.000 description 2
- 239000003153 chemical reaction reagent Substances 0.000 description 2
- 238000001035 drying Methods 0.000 description 2
- 239000003995 emulsifying agent Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 230000004048 modification Effects 0.000 description 2
- 238000012986 modification Methods 0.000 description 2
- 150000003856 quaternary ammonium compounds Chemical class 0.000 description 2
- 210000002268 wool Anatomy 0.000 description 2
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- GKQHIYSTBXDYNQ-UHFFFAOYSA-M 1-dodecylpyridin-1-ium;chloride Chemical compound [Cl-].CCCCCCCCCCCC[N+]1=CC=CC=C1 GKQHIYSTBXDYNQ-UHFFFAOYSA-M 0.000 description 1
- VBICKXHEKHSIBG-UHFFFAOYSA-N 1-monostearoylglycerol Chemical compound CCCCCCCCCCCCCCCCCC(=O)OCC(O)CO VBICKXHEKHSIBG-UHFFFAOYSA-N 0.000 description 1
- JSMRDVDHYKKNFC-UHFFFAOYSA-N 2-octadecylpyridine;hydrobromide Chemical compound Br.CCCCCCCCCCCCCCCCCCC1=CC=CC=N1 JSMRDVDHYKKNFC-UHFFFAOYSA-N 0.000 description 1
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 1
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
- DCXXMTOCNZCJGO-UHFFFAOYSA-N Glycerol trioctadecanoate Natural products CCCCCCCCCCCCCCCCCC(=O)OCC(OC(=O)CCCCCCCCCCCCCCCCC)COC(=O)CCCCCCCCCCCCCCCCC DCXXMTOCNZCJGO-UHFFFAOYSA-N 0.000 description 1
- 101100270435 Mus musculus Arhgef12 gene Proteins 0.000 description 1
- 229920000297 Rayon Polymers 0.000 description 1
- 150000001299 aldehydes Chemical class 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 238000009835 boiling Methods 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 150000001768 cations Chemical class 0.000 description 1
- DVBJBNKEBPCGSY-UHFFFAOYSA-M cetylpyridinium bromide Chemical compound [Br-].CCCCCCCCCCCCCCCC[N+]1=CC=CC=C1 DVBJBNKEBPCGSY-UHFFFAOYSA-M 0.000 description 1
- 238000006243 chemical reaction Methods 0.000 description 1
- 150000001805 chlorine compounds Chemical class 0.000 description 1
- 230000000694 effects Effects 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 210000004209 hair Anatomy 0.000 description 1
- 150000004820 halides Chemical class 0.000 description 1
- 229910052736 halogen Inorganic materials 0.000 description 1
- 150000004678 hydrides Chemical class 0.000 description 1
- 150000002430 hydrocarbons Chemical group 0.000 description 1
- XMBWDFGMSWQBCA-UHFFFAOYSA-N hydrogen iodide Chemical compound I XMBWDFGMSWQBCA-UHFFFAOYSA-N 0.000 description 1
- ATADHKWKHYVBTJ-UHFFFAOYSA-N hydron;4-[1-hydroxy-2-(methylamino)ethyl]benzene-1,2-diol;chloride Chemical compound Cl.CNCC(O)C1=CC=C(O)C(O)=C1 ATADHKWKHYVBTJ-UHFFFAOYSA-N 0.000 description 1
- 229910017464 nitrogen compound Inorganic materials 0.000 description 1
- 150000002830 nitrogen compounds Chemical group 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 239000011368 organic material Substances 0.000 description 1
- 238000002360 preparation method Methods 0.000 description 1
- JUJWROOIHBZHMG-UHFFFAOYSA-N pyridine Substances C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 description 1
- 239000002964 rayon Substances 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 229910000029 sodium carbonate Inorganic materials 0.000 description 1
- 239000002904 solvent Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 229920002994 synthetic fiber Polymers 0.000 description 1
- 235000020681 well water Nutrition 0.000 description 1
- 239000002349 well water Substances 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
- D06M13/10—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
- D06M13/184—Carboxylic acids; Anhydrides, halides or salts thereof
- D06M13/188—Monocarboxylic acids; Anhydrides, halides or salts thereof
Definitions
- One object of my present invention is to pro- By reason of this there is also danger that, when vide a process of the type described in which the 10 water and heat are employed, a further portion use of abnormally low temperatures, and the subof the reagent employed becomes'saponified and sequent increase in cost of production is eliminattherefore valueless from an industrial standpoint. ed in this type of yarn and fabric treatment. Therefore, it has become common in the in- Another object of my present invention is to dustry to dry the impregnated product through provide a new and novel treating means which the use of low temperatures over a considerable gives more advantageous results than have hith-. period of time, thus materially increasing proerto been considered possible. duction costs. Despite precautions of this type,
- a series of fatty comappropriate emulsifying agents which are, for pounds, for example, esterifying agents, such as example, f th anhydrides, amides, aldehydes and the like, emulsified in water, may also be used.
- esterifying agents such as example, f th anhydrides, amides, aldehydes and the like, emulsified in water
- R i iCl type I g It has been found that when water has been used in theprior art as a medium certain esteriand m which R represents the Pamflin Cham, and f i agents, such as anhydrides become inei; where other halides'may be substituted for chlofective because they saponify prematurely.
- Example I 5 kg. of a mixture of cetyl-pyridinechloride and a stearyl-pyridine chloride, such as are obtained from stearin, are dissolved in 500 liters of softened water and heated to 70 G. Then 20 kg. of acid anhydrides derived from train oil (blubber) are melted and introduced with stirring, in a thin jet, into the aqueous solution. Subsequently the entire mass is diluted with another 500 liters of cold water, stirred and then further cooled. The fine emulsion is now ready for use and 40 kg. of staple fibres are added to the emulsion and the fibre mass is well soaked therein.
- the staple fibres are thoroughly hydro-extracted in a centrifuge and placed in loose layers on a belt drier and dried at a temperature not exceeding 50 C. As soon as the water is extracted, the drying temperature is increased to approximately 100 C. and maintained there until the water-repellent efiect becomes fast enough so that it will resist boiling. This usually requires approximately one hour.
- Example II The same procedure as outlined in Example I is followed, with the exception that a mixture of cetyl pyridine bromide and stearyl pyridine bromide is used. This mixture is known in the industry under the trade name Fixanol.”
- Example III The same procedure as outlined in Example I is followed, with the exception that lauryl pyridinium chloride is used as emulsifying agent, together with ordinary well water and that the drying is carried out at 70 C.
- staple fibres instead of staple fibres, other textile materials, such as artificial silk, cotton, fiax, wool, casein fibres, also in the form of fabrics and woven material, as well as artificial horse hair and films may be treated in a similar way.
- other textile materials such as artificial silk, cotton, fiax, wool, casein fibres, also in the form of fabrics and woven material, as well as artificial horse hair and films may be treated in a similar way.
- water-soluble cation-active compounds includes cation-active compounds which are 'sufliciently water-soluble to furnish surface-active cations therein
- textile material embraces filaments, fibres, threads, etc., as well as fabrics, knitted or woven cloths, films etc., of natural or synthetic fibres.
- the steps which comprise treating a textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active pyridinium compound having an aliphatic radical of at least 10 carbon atoms and water, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in 'said emulsion acting to substantially reduce saponification of said esterifying agent in said water.
- the steps which comprise treating a cellulosic textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active quaternary ammonium compound and water, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in said emulsion acting to substantially reduce saponiflcation of said esterifying agent in said water.
Description
Patented Jan. 20, 1942 v I TREATMENT OF TEXTILE MATERIALS Wolfgang Linnhofl', Berlin-Lankwitz, Germany, assignor to North American Rayon Corporation, New York, N. Y., a corporation of Delaware No Drawing. Application November 15, 1938, eial No. 240,573. In Germany November 15,
6 Claims. (Cl..8120) My present invention has to do with a new and occur during and shortly after the production of novel process for use in the treatment of artifithe emulsion even when there was a strict temcial silk, wool, cotton, casein and the like, and perature control maintained. Inlarge scale proof woven and knitted fabrics made therefrom, and duction it has oftentimes been impossible to imhas to do more specifically with th chemical mediately use the prepared compounds and as a treatment of such fibers and the goods made result extensive saponification continuously octherefrom in order to make them more watercurs. It is necessary to dry and harden fibres epe en which have been treated with this preparation.
One object of my present invention is to pro- By reason of this there is also danger that, when vide a process of the type described in which the 10 water and heat are employed, a further portion use of abnormally low temperatures, and the subof the reagent employed becomes'saponified and sequent increase in cost of production is eliminattherefore valueless from an industrial standpoint. ed in this type of yarn and fabric treatment. Therefore, it has become common in the in- Another object of my present invention is to dustry to dry the impregnated product through provide a new and novel treating means which the use of low temperatures over a considerable gives more advantageous results than have hith-. period of time, thus materially increasing proerto been considered possible. duction costs. Despite precautions of this type,
These and other objects of my invention will in however, it has been found that a larg portion p be ppa nt and in part pointed out by a of the anhydride becomes saponified and thus careful consideration of the following specificalost, Thi means that a large percentage of the tion and claims. reagent is unable to perform its normal function The p r art d s ri s pr sses w r y prodin the reaction and, as a result, the water-reucts made from cellulose and cellulose derivatives, pellent effect on the fibre either does not occur or, such as artificial silk, staple fibres, artificial if it does, occurs only to a limited extent. o s -ha and films, and also natural fi s. I have now found, and this is the basis of my s as o o a and even W001 y be superpresent invention, that it is possible to produce ficially esterified It s also Well known, intreatemulsions from fatty acid anhydrides and the menfis Of this type, that o a n iphatic like which are much less subject to saponificampoun s y be mployed n rd r to give tion and which at the same time exert no dewelier-lepellent p operties to the treated goods. structive influence upon the products treated, for Hitherto, use has been made of chlorides, anexample, fibres. Tests have shown that certain hydrides d amides of fatty acids d long organic materials in the form of quaternary niehe n e ydes and isocyanatesn p oc trogen compounds can produce emulsions of fatty Of t s Class i s necessary that during the esteriacid anhydride, for example, of the class of stearic fi e e long chain e s. e. o o e perefa acid anhydride, or anhydrides such as are obfins become an h r d on and n t cellulose tained from hardened train oil (blubber), etc., in fiber With'the id of appr priate reactive groupswater. In the emulsions thus obtained, only-a This p ss, n the light of present knowledge, very small saponification takes place in the aquemay be a c p s p d n p the means .ous medium as well as on the fibre. Water-soluof esterification, through the use of an organic 40 b quaternary nitrogen compounds of parafilns non-solvent of cellulose, such as benzene, carbon with at least; 10 carbon atoms have proved to be tetrachloride and the like. A series of fatty comappropriate emulsifying agents which are, for pounds, for example, esterifying agents, such as example, f th anhydrides, amides, aldehydes and the like, emulsified in water, may also be used. R i iCl type I g It has been found that when water has been used in theprior art as a medium certain esteriand m which R represents the Pamflin Cham, and f i agents, such as anhydrides become inei; where other halides'may be substituted for chlofective because they saponify prematurely. In I practice it has been found that many inconven- I have l n a among Others, e fy iences arise because of this saponification. Hithp i in hloride, cetyl-pyridine chloride, cetyli erto this emulsion has been made, for example, py i e bromida-cet l-pyridine iodide as well from fatty acid anhydrides using the common stearyl-pyridine chloride are valuable as eiri s1 admixtures of soap and sodium carbonate. A fyin agents.
considerable saponification has been found to The use of acid anhydrides of hardened train within the scope of the appended claims.
oil (blubber) and a mixture of cetyl-pyridine chloride and stearyl-pyridine chloride, such as may be obtained from technical steal-in, has also produced very favorable results. High molecular pyridinium halides, obtained from hardened train oil (blubber), may also be used.
In order to more definitely indicate the manner in which my present invention may be used in the industry, I shall give three examples which will serve to clearly point out several possible uses.
Example I 5 kg. of a mixture of cetyl-pyridinechloride and a stearyl-pyridine chloride, such as are obtained from stearin, are dissolved in 500 liters of softened water and heated to 70 G. Then 20 kg. of acid anhydrides derived from train oil (blubber) are melted and introduced with stirring, in a thin jet, into the aqueous solution. Subsequently the entire mass is diluted with another 500 liters of cold water, stirred and then further cooled. The fine emulsion is now ready for use and 40 kg. of staple fibres are added to the emulsion and the fibre mass is well soaked therein. After treatment in the emulsion, the staple fibres are thoroughly hydro-extracted in a centrifuge and placed in loose layers on a belt drier and dried at a temperature not exceeding 50 C. As soon as the water is extracted, the drying temperature is increased to approximately 100 C. and maintained there until the water-repellent efiect becomes fast enough so that it will resist boiling. This usually requires approximately one hour.
Example II The same procedure as outlined in Example I is followed, with the exception that a mixture of cetyl pyridine bromide and stearyl pyridine bromide is used. This mixture is known in the industry under the trade name Fixanol."
Example III The same procedure as outlined in Example I is followed, with the exception that lauryl pyridinium chloride is used as emulsifying agent, together with ordinary well water and that the drying is carried out at 70 C.
Instead of staple fibres, other textile materials, such as artificial silk, cotton, fiax, wool, casein fibres, also in the form of fabrics and woven material, as well as artificial horse hair and films may be treated in a similar way.
Modifications of my invention will readily be recognized by those skilled in the art, and I desire to include all such modifications coming In these claims the term water-soluble cation-active compounds includes cation-active compounds which are 'sufliciently water-soluble to furnish surface-active cations therein, and the term textile material" embraces filaments, fibres, threads, etc., as well as fabrics, knitted or woven cloths, films etc., of natural or synthetic fibres.
I claim:
1. In the process of rendering textile materials water repellent, the steps which comfiise treating a textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active quaternary ammonium compound having an aliphatic radical of at least carbon atoms, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in said emulsion acting to substantially reduce saponiflcation of said esterifying agent in said water.
2. In the process of rendering textile materials water repellent, the steps which comprise treating a textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active pyridinium compound having an aliphatic radical of at least 10 carbon atoms and water, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in 'said emulsion acting to substantially reduce saponification of said esterifying agent in said water.
3. In the process of rendering textile materials water repellent, the steps which comprise treating a textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, water and a water soluble cation-active pyridinium halide having the structure R-N-halogen in which R represents a hydrocarbon chain having at least 10 carbon atoms derived from hardened blubber, and subsequently heating said treated material to cause esterification thereof,
water repellent, the steps which comprise treating a cellulosic textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active quaternary ammonium compound and water, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in said emulsion acting to substantially reduce saponiflcation of said esterifying agent in said water.
6. In the process of rendering textile materals water repellent, the steps which comprise treating acellulosic textile material with an emulsion comprising a substantially water insoluble, long chain, aliphatic anhydride esterifying agent, a water soluble cation-active pyridinium compound and water, and subsequently heating said treated material to cause esterification thereof, said cation-active compound present in said emulsion acting to substantially reduce saponiflcation of said esterifying agent in said water.
WOLFGANG LINNHOFF.
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2270658X | 1937-11-15 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2270658A true US2270658A (en) | 1942-01-20 |
Family
ID=7993199
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US240573A Expired - Lifetime US2270658A (en) | 1937-11-15 | 1938-11-15 | Treatment of textile materials |
Country Status (1)
Country | Link |
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US (1) | US2270658A (en) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2420499A (en) * | 1942-01-14 | 1947-05-13 | Chem Ind Basel | Process of esterifying cellulose fibers |
US3887427A (en) * | 1971-07-15 | 1975-06-03 | Kema Nord Ab | Process for sizing cellulose fibers |
-
1938
- 1938-11-15 US US240573A patent/US2270658A/en not_active Expired - Lifetime
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2420499A (en) * | 1942-01-14 | 1947-05-13 | Chem Ind Basel | Process of esterifying cellulose fibers |
US3887427A (en) * | 1971-07-15 | 1975-06-03 | Kema Nord Ab | Process for sizing cellulose fibers |
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