US2608494A - Treatment of textile fabrics for imparting antishrink properties thereto - Google Patents
Treatment of textile fabrics for imparting antishrink properties thereto Download PDFInfo
- Publication number
- US2608494A US2608494A US111971A US11197149A US2608494A US 2608494 A US2608494 A US 2608494A US 111971 A US111971 A US 111971A US 11197149 A US11197149 A US 11197149A US 2608494 A US2608494 A US 2608494A
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- United States
- Prior art keywords
- fabric
- impregnated
- temperature
- group
- dried
- 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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- 239000004744 fabric Substances 0.000 title claims description 47
- 239000004753 textile Substances 0.000 title claims description 7
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 claims description 28
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 claims description 20
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 18
- 238000000034 method Methods 0.000 claims description 11
- 229910021529 ammonia Inorganic materials 0.000 claims description 10
- UMGDCJDMYOKAJW-UHFFFAOYSA-N thiourea Chemical compound NC(N)=S UMGDCJDMYOKAJW-UHFFFAOYSA-N 0.000 claims description 8
- 239000004202 carbamide Substances 0.000 claims description 7
- 238000001035 drying Methods 0.000 claims description 7
- 239000004627 regenerated cellulose Substances 0.000 claims description 7
- 229920000877 Melamine resin Polymers 0.000 claims description 6
- POULHZVOKOAJMA-UHFFFAOYSA-N dodecanoic acid Chemical compound CCCCCCCCCCCC(O)=O POULHZVOKOAJMA-UHFFFAOYSA-N 0.000 claims description 6
- FUZZWVXGSFPDMH-UHFFFAOYSA-N hexanoic acid Chemical compound CCCCCC(O)=O FUZZWVXGSFPDMH-UHFFFAOYSA-N 0.000 claims description 6
- 150000007524 organic acids Chemical class 0.000 claims description 6
- JVTAAEKCZFNVCJ-UHFFFAOYSA-N lactic acid Chemical compound CC(O)C(O)=O JVTAAEKCZFNVCJ-UHFFFAOYSA-N 0.000 claims description 4
- JDSHMPZPIAZGSV-UHFFFAOYSA-N melamine Chemical compound NC1=NC(N)=NC(N)=N1 JDSHMPZPIAZGSV-UHFFFAOYSA-N 0.000 claims description 4
- CBCKQZAAMUWICA-UHFFFAOYSA-N 1,4-phenylenediamine Chemical compound NC1=CC=C(N)C=C1 CBCKQZAAMUWICA-UHFFFAOYSA-N 0.000 claims description 3
- AVXURJPOCDRRFD-UHFFFAOYSA-N Hydroxylamine Chemical compound ON AVXURJPOCDRRFD-UHFFFAOYSA-N 0.000 claims description 3
- 239000005639 Lauric acid Substances 0.000 claims description 3
- FEWJPZIEWOKRBE-UHFFFAOYSA-N Tartaric acid Natural products [H+].[H+].[O-]C(=O)C(O)C(O)C([O-])=O FEWJPZIEWOKRBE-UHFFFAOYSA-N 0.000 claims description 3
- 150000001462 antimony Chemical class 0.000 claims description 3
- HFACYLZERDEVSX-UHFFFAOYSA-N benzidine Chemical compound C1=CC(N)=CC=C1C1=CC=C(N)C=C1 HFACYLZERDEVSX-UHFFFAOYSA-N 0.000 claims description 3
- 239000011975 tartaric acid Substances 0.000 claims description 3
- 235000002906 tartaric acid Nutrition 0.000 claims description 3
- 239000004310 lactic acid Substances 0.000 claims description 2
- 235000014655 lactic acid Nutrition 0.000 claims description 2
- 238000004329 water eliminated fourier transform Methods 0.000 claims 1
- 150000001412 amines Chemical class 0.000 description 6
- 238000005470 impregnation Methods 0.000 description 5
- 239000002253 acid Substances 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 229920001807 Urea-formaldehyde Polymers 0.000 description 3
- ODGAOXROABLFNM-UHFFFAOYSA-N polynoxylin Chemical compound O=C.NC(N)=O ODGAOXROABLFNM-UHFFFAOYSA-N 0.000 description 3
- 229960003656 ricinoleic acid Drugs 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 2
- 229920000297 Rayon Polymers 0.000 description 2
- 229920002301 cellulose acetate Polymers 0.000 description 2
- LEQAOMBKQFMDFZ-UHFFFAOYSA-N glyoxal Chemical compound O=CC=O LEQAOMBKQFMDFZ-UHFFFAOYSA-N 0.000 description 2
- WBHHMMIMDMUBKC-XLNAKTSKSA-N ricinelaidic acid Chemical compound CCCCCC[C@@H](O)C\C=C\CCCCCCCC(O)=O WBHHMMIMDMUBKC-XLNAKTSKSA-N 0.000 description 2
- FEUQNCSVHBHROZ-UHFFFAOYSA-N ricinoleic acid Natural products CCCCCCC(O[Si](C)(C)C)CC=CCCCCCCCC(=O)OC FEUQNCSVHBHROZ-UHFFFAOYSA-N 0.000 description 2
- 230000008961 swelling Effects 0.000 description 2
- -1 0.3% to 0.6% Chemical compound 0.000 description 1
- 229920003043 Cellulose fiber Polymers 0.000 description 1
- FEWJPZIEWOKRBE-JCYAYHJZSA-N Dextrotartaric acid Chemical compound OC(=O)[C@H](O)[C@@H](O)C(O)=O FEWJPZIEWOKRBE-JCYAYHJZSA-N 0.000 description 1
- 206010013786 Dry skin Diseases 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000003377 acid catalyst Substances 0.000 description 1
- 229910052787 antimony Inorganic materials 0.000 description 1
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 description 1
- SZXAQBAUDGBVLT-UHFFFAOYSA-H antimony(3+);2,3-dihydroxybutanedioate Chemical compound [Sb+3].[Sb+3].[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O.[O-]C(=O)C(O)C(O)C([O-])=O SZXAQBAUDGBVLT-UHFFFAOYSA-H 0.000 description 1
- XCSAHPBBCIBIQD-UHFFFAOYSA-K bis(2-hydroxypropanoyloxy)stibanyl 2-hydroxypropanoate Chemical compound [Sb+3].CC(O)C([O-])=O.CC(O)C([O-])=O.CC(O)C([O-])=O XCSAHPBBCIBIQD-UHFFFAOYSA-K 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 239000008098 formaldehyde solution Substances 0.000 description 1
- IVJISJACKSSFGE-UHFFFAOYSA-N formaldehyde;1,3,5-triazine-2,4,6-triamine Chemical compound O=C.NC1=NC(N)=NC(N)=N1 IVJISJACKSSFGE-UHFFFAOYSA-N 0.000 description 1
- 229940015043 glyoxal Drugs 0.000 description 1
- 229960000448 lactic acid Drugs 0.000 description 1
- 150000007974 melamines Chemical class 0.000 description 1
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 1
- 230000007935 neutral effect Effects 0.000 description 1
- ZQPPMHVWECSIRJ-KTKRTIGZSA-N oleic acid group Chemical group C(CCCCCCC\C=C/CCCCCCCC)(=O)O ZQPPMHVWECSIRJ-KTKRTIGZSA-N 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000000344 soap Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 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
- D06M15/00—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment
- D06M15/19—Treating fibres, threads, yarns, fabrics, or fibrous goods made from such materials, with macromolecular compounds; Such treatment combined with mechanical treatment with synthetic macromolecular compounds
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/39—Aldehyde resins; Ketone resins; Polyacetals
- D06M15/423—Amino-aldehyde resins
Definitions
- a further proposal has been to use acetone ferinaldehyde condensation products and 1 it has i also been suggested to use glyoxal alone orwith otherbompounds such as the pm-condensates of'urea-formaldehyde or of melamine formaldehyde in thepresence of polyvinyl alcohol.
- Thejprimary object of the present invention is to provide a novel process for imparting anti- "mma roperues to'textile fabrics containing regenerated cellulose which is carriedout in two separate stages ⁇ whereby improvedfanti shrink properties are-irnparted tcf such fabrics, the swelling capacity of such fabrics is reduced, and the fastnss of such fabrics to light is increased.
- the process according to the present invention uses two separatebaths, the first bath containingeither: v. i i
- Example 2 A black morrocain cloth of 36" width having a warp of 100% cellulose acetate and a-weft of 50% cellulose acetate and 50% viscose is impregnated at normal temperature in a bath in which the ratio of cloth to liquidis-about 1:4 contain:
- ricinoleic, caproic and lauric acid ammonia and an organic amine base selected from the group consisting of urea, thiourea, melamine, hydroxylamine, benzidine and para-phenylendiamine, runtil completely impregnated therewith, drying the thus impregnated fabric, treating the dried impregnated fabric: in a second bath; containing formaldehyde having a substantially 20% to 10%; concentration, and the antimony salt of an organic, acid selected from the group consisting oflactic-acidand tartaric acid, drying the impregnated. fabric, and baking the dried impregnated fabric.
- an organic amine base selected from the group consisting of urea, thiourea, melamine, hydroxylamine, benzidine and para-phenylendiamine
- a processlfo'r imparting anti-shrink properties'to textile fabrics composed mainly at least of regenerated cellulose, which comprises impregnating such a fabric at normal temperature in a sisting of lacticacid and tartaric acid until the fabric is completely impregnated therewith, drying the impregnated fabric while under an over stretch of 2% to 3% inthe Weft and an overfeed in the warp, baking thedriedimpregnated fabric at a temperature ofabout C. for about fi t0 8. minutes, and finally giving the baked fabric a soaping treatment-J with the addition of an amount of ammonia sufficient to remove any free formaldehyde remaining in the fabric.
- a -process for imparting anti-shrink propr ertiesto textile fabrics composed mainly at least of regenerated cellulose, which comprises impregnating such a fabric at normal temperature in a bath-of liquidcontaining from 0.3% to 0.6%
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Description
Patented Aug. 26, 1952 V TREATMENTOF TEXTItE FABRICSFOR HWPARTING ANTISH Hugh vom Hove; Newport, England; assighor of; one-half to Walkden Makin & (lo/Limited,
Openshaw Manchester, England t No Drawing. Application August 23, 1949; Serial NK PRQPERTIES No.'11 1,971. In Great Britain August 28, 1948 This invention relates to improvements in processes for imparting anti-shrink properties to textile fabrics composed of or containing regen- "erated cellulose fibres and-is particularly applicable for the treatment of'crepe fabrics. f "Pr'ocesses for such purpose are known in which the fabricis impregnatedwith the pre-condensates of urea-formaldehyde resinsand which; formaldehyde alone is employed to alter the hydr'ophilic properties, thetreatment being carried .out in 'the presence of a strong acid catalyst.
A further proposal has been to use acetone ferinaldehyde condensation products and 1 it has i also been suggested to use glyoxal alone orwith otherbompounds such as the pm-condensates of'urea-formaldehyde or of melamine formaldehyde in thepresence of polyvinyl alcohol.
: Furthermore, it has been suggested; when employing the" pre -condensates of urea formaldehyde in order to prevent theformationof substances of high molecular structure, to carry out the process in two baths, the first batheontain- "ing urea, preferably withcertainmetals salts, at a concentration of about 20% and the second -bath-being-a strong formaldehyde-solution of from20%to 40%. I Thejprimary object of the present invention is to provide a novel process for imparting anti- "mma roperues to'textile fabrics containing regenerated cellulose which is carriedout in two separate stages} whereby improvedfanti shrink properties are-irnparted tcf such fabrics, the swelling capacity of such fabrics is reduced, and the fastnss of such fabrics to light is increased.
The process according to the present invention uses two separatebaths, the first bath containingeither: v. i i
(a) A weak organic acid'which isnearly in soluble in water and having one or more alcohol-hydroxylgroups and ammonia, or v (bl A similar weak organic acid, together with ammonia, an organic amine base such as urea,
1 :fiClaims. (01.117 7) After complete impregnation in the first bath the fabric is dried (with or without dimensional control) at a temperature of between 60 (Land 120 C, Aftertreatment in the second bath the fabricis dried within the same range of temperature under dimensional control such as on awstentengiving an over stretch of 2% to 3% -in-the weft and overfed in the warp; "Ihefabric is then baked at a temperature of about 150 C for about'6 to 8 minutes and the process is' completedby a short'soaping treatment with the additidns of a small amountof ammonia to remove any free formaldehyde remaining in the fabric. The'followingexamples in which the quantities are by weight are given as illustrative of the inveritionv Exa'm'plei w A green dyedcrepe of 36 inch width containing100% regenerated cellulose (viscose) in both warp and weft is impregnated at normal tein perature in a bath in which-the ratio of clothto liquidis 'about lz4'containing from 1.5% tb'2i3% of pure-ricinoleic acid, 0.35% to 0.6% concen- :trated ammonia and about 0.5 of a {suitable known softener, the pH value of thebath b'eing about 8. l a "After complete impregnation of theiabric it is squeezedin a pad mangle at a' pressurepf about 200 to 250 lbs. per square inch so that it contains about 80% of the liquid; and dried'ofi 'adr'um dryer at a'temperature of from 60 C.
v The dried fabric is then impregnated again at normal temperaturein a second bath'contain ing between 2.5% and 5% antimony lactate and 5% to 7% of formaldehyde, squeezedin a pad mangle until it contains about 80% of the'liquid,
dried on a stenter with about 2% stretch {in-the thiourea; melamine,-hydroxylamine, benz'idine or para-phenylendiamines and the second bath containing formaldehyde" of medium concentration and antimony lactateor antimony tartrate, when the first bath contains no ,organic amine base the amount of the organic acid shouldbe berinsed and dried V weft at'a temperature of from C.to C and, when dry, baked for about 6 to 8 minutes ata temperature of about C. c- After baking thefabric is washed in a bath containing about 0.5% of a neutral soap and about0.5% concentrated ammbrliaiit isthen well The following table gives a comparisonof ui fabric before and after treatment in the dry Sat i a T n Shrinkfstge percent ens e 8 er 7 Stretch strength ingrammes pement lstwash 2nd 3rd Untreated fabric e 194 24.7 19.5 20 Treatedfabric 199 24.4 1.4 1.4 1.4
Moreover theswelling capacity is reduced from 78% in"? the; untreated fabric to 36% in the treated fabric:
Example 2 A black morrocain cloth of 36" width having a warp of 100% cellulose acetate and a-weft of 50% cellulose acetate and 50% viscose is impregnated at normal temperature in a bath in which the ratio of cloth to liquidis-about 1:4 contain:
ing 7.5% to 10. urea, 0.3% to 0.6% ,ricinoleic acid or beta oxynaphthic acid and about 0.2% concentrated ammonia. l
After impregnation the fabric is dried, treated lna second bath and baked as described in Example 1.
The following table gives a comparison of the fabric in the dry state before and after treatj swelling capacity is reduced from 83% in the untreated fabric to 33% in the treated-fabric.
It. is found in many cases that the treatment of or containing regenerated cellulose not only imparts anti-shrink properties to the fabric but also increases fastness of the fabric to light.
Iclaim: r
. 1.' A process for, imparting anti-shrink proper;
ties to textile fabrics containing at leasta sub- ,stantial amount of regenerated cellulose, consisting .-in treating such a fabric. at normal tem- .peraturein'a bath containing a weak organic bath containing a weak organic selected from the-group consisting of ioleicg ricinoleic,
caproic and lauric acid, ammonia, and an organic amine base selected from the group consisting of urea, thiourea, melamine, hydroxylamine, benzidine and para-phenylendiamine, until completely. impregnated therewith, drying the impregnated fabric at a temperature between 60 ,C. and 120 (3., impregnating the dried fabric at normal temperature in a second bath containing formaldehyde having a substantially to concentration, and the antimony salt of a weak organic acid selected from the group conaccording to the invention of afabric composed acid selected from the group consisting of oleic, 1
ricinoleic, caproic and lauric acid, ammonia and an organic amine base selected from the group consisting of urea, thiourea, melamine, hydroxylamine, benzidine and para-phenylendiamine, runtil completely impregnated therewith, drying the thus impregnated fabric, treating the dried impregnated fabric: in a second bath; containing formaldehyde having a substantially 20% to 10%; concentration, and the antimony salt of an organic, acid selected from the group consisting oflactic-acidand tartaric acid, drying the impregnated. fabric, and baking the dried impregnated fabric.
2. A process as defined in claim 1, wherein the organic [acid employed in the first bathis-ricinoleic acid.
3. A process as definedin claim 1, wherein the organic amine base employed in the first bath is urea. v
' lofsubsta 'ntially from 605C. to
1 4. process asdefined in claim 1,;wherein the organic amine base employed in the first bathis melamine. ,7
1,5. A processlfo'r imparting anti-shrink properties'to textile fabrics composed mainly at least of regenerated cellulose, which comprises impregnating such a fabric at normal temperature in a sisting of lacticacid and tartaric acid until the fabric is completely impregnated therewith, drying the impregnated fabric while under an over stretch of 2% to 3% inthe Weft and an overfeed in the warp, baking thedriedimpregnated fabric at a temperature ofabout C. for about fi t0 8. minutes, and finally giving the baked fabric a soaping treatment-J with the addition of an amount of ammonia sufficient to remove any free formaldehyde remaining in the fabric. I
A -process for imparting anti-shrink propr ertiesto textile fabrics composed mainly at least of regenerated cellulose, which comprises impregnating such a fabric at normal temperature in a bath-of liquidcontaining from 0.3% to 0.6%
0.2%ic'oncentratedammonia, and which bath the ratio-of fabric to liquid is; substantially 1:4,
until impregnation of the fabric, with ;the-;1iquid bath is complete,v dry-ing the thus-.impregnated r fabric at a temperature of substantiallyqfiw, C. to 12 Off (2., subsequently impregnating such T d ried impregnated fabric at normal temperature; ina secondbath of liquid containing substantially between 2.5% and 5% ;of the antimonysalt pf an organic acidselected from the group consisting of formaldehyde having a concentration of -substantially between 20% and 40%, until impregnation of the fabric with the liquid-.in-the second ba i'si'com lete ryi the.im i sna ea rabuc from. the second bath whileunder substantially 2% to' 3% stretch in the weft at a temperature 7 I r r r g 20? 0;, and bak ingthedried impregnated-fabric for-from S te 8 minutes t a empe at re s b ta tial y; 3C.
Claims (1)
- 5. A PROCESS FOR IMPARTING ANTI-SHRINK PROPERTIES TO TEXTILE FABRICS COMPOSED MAINLY AT LEAST OF REGENERATED CELLULOSE, WHICH COMPRISES IMPREGNATING SUCH A FABRIC AT NORMAL TEMPERATURE IN A BATH CONTAINING A WEAK ORGANIC ACID SELECTED FROM THE GROUP CONSISTING OF OLEIC, RICHINOLEIC, CAPROIC AND LAURIC ACID, AMMONIA, AND AN ORGANIC AMINE BASE SELECTED FROM THE GROUP CONSISTING OF UREA, THIOUREA, MELAMINE, HYDROXYLAMINE, BENZIDINE AND PARA-PHENYLENDIAMINE, UNTIL COMPLETELY IMPREGNATED THEREWITH, DRYING THE IMPREGNATED FABRIC AT A TEMPERATURE BETWEEN 60* C. AND 120* C., IMPREGNATING THE DRIED FABRIC AT NORMAL TEMPERATURE IN A SECOND BATH CONTAINING FORMALDEHYDE HAVING A SUBSTANTIALLY 20% TO 40% CONCENTRATION, AND THE ANTIMONY SALT OF A WEAK ORGANIC ACID SELECTED FROM THE GROUP CONSISTING OF LACTIC ACID AND TARTARIC ACID UNTIL THE FABRIC IS COMPLETELY IMPREGNATED THEREWITH, DRYING THE IMPREGNATED FABRIC WHILE UNDER AN OVER STRETCH OF 2% TO 3% IN THE WEFT AND AN OVERFEED IN THE WARP, BAKING THE DRIED IMPREGNATED FABRIC AT A TEMPERATURE OF ABOUT 150* C. FOR ABOUT 6 TO 8 MINUTES, AND FINALLY GIVING THE BAKED FABRIC A SOAPING TREATMENT WITH THE ADDITION OF AN AMOUNT OF AMMONIA SUFFICIENT TO REMOVE ANY FREE FORMALDEHYDE REMAINING IN THE FABRIC.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB2608494X | 1948-08-28 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| US2608494A true US2608494A (en) | 1952-08-26 |
Family
ID=10911506
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| US111971A Expired - Lifetime US2608494A (en) | 1948-08-28 | 1949-08-23 | Treatment of textile fabrics for imparting antishrink properties thereto |
Country Status (1)
| Country | Link |
|---|---|
| US (1) | US2608494A (en) |
Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| GB495714A (en) * | 1937-04-23 | 1938-11-14 | Ig Farbenindustrie Ag | Improvements in treating textile materials |
| GB501288A (en) * | 1937-08-23 | 1939-02-23 | John Gwynant Evans | Process of treating cellulosic textile materials |
| US2165265A (en) * | 1935-05-12 | 1939-07-11 | Ig Farbenindustrie Ag | Process of imparting hydrophobic properties to cellulose fibers |
| US2175183A (en) * | 1935-01-21 | 1939-10-10 | Celanese Corp | Treatment of textile materials |
| US2191362A (en) * | 1936-06-27 | 1940-02-20 | Ciba Products Corp | Treatment of textile materials |
| US2242565A (en) * | 1937-03-15 | 1941-05-20 | Heberlein Patent Corp | Chemicals for water repellence |
-
1949
- 1949-08-23 US US111971A patent/US2608494A/en not_active Expired - Lifetime
Patent Citations (6)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2175183A (en) * | 1935-01-21 | 1939-10-10 | Celanese Corp | Treatment of textile materials |
| US2165265A (en) * | 1935-05-12 | 1939-07-11 | Ig Farbenindustrie Ag | Process of imparting hydrophobic properties to cellulose fibers |
| US2191362A (en) * | 1936-06-27 | 1940-02-20 | Ciba Products Corp | Treatment of textile materials |
| US2242565A (en) * | 1937-03-15 | 1941-05-20 | Heberlein Patent Corp | Chemicals for water repellence |
| GB495714A (en) * | 1937-04-23 | 1938-11-14 | Ig Farbenindustrie Ag | Improvements in treating textile materials |
| GB501288A (en) * | 1937-08-23 | 1939-02-23 | John Gwynant Evans | Process of treating cellulosic textile materials |
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