US2160375A - Water-repellent textile material and process of manufacturing it - Google Patents
Water-repellent textile material and process of manufacturing it Download PDFInfo
- Publication number
- US2160375A US2160375A US11867836A US2160375A US 2160375 A US2160375 A US 2160375A US 11867836 A US11867836 A US 11867836A US 2160375 A US2160375 A US 2160375A
- Authority
- US
- United States
- Prior art keywords
- mixed
- water
- impregnated
- vinyl
- textile materials
- 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
- 239000000463 material Substances 0.000 title description 30
- 239000004753 textile Substances 0.000 title description 23
- 238000000034 method Methods 0.000 title description 13
- 239000005871 repellent Substances 0.000 title description 12
- 238000004519 manufacturing process Methods 0.000 title description 5
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 12
- 239000000243 solution Substances 0.000 description 12
- OFOBLEOULBTSOW-UHFFFAOYSA-N Propanedioic acid Natural products OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- VZCYOOQTPOCHFL-UPHRSURJSA-N maleic acid Chemical compound OC(=O)\C=C/C(O)=O VZCYOOQTPOCHFL-UPHRSURJSA-N 0.000 description 11
- 239000011976 maleic acid Substances 0.000 description 11
- VZCYOOQTPOCHFL-UHFFFAOYSA-N trans-butenedioic acid Natural products OC(=O)C=CC(O)=O VZCYOOQTPOCHFL-UHFFFAOYSA-N 0.000 description 11
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 11
- 125000004432 carbon atom Chemical group C* 0.000 description 10
- 150000001875 compounds Chemical class 0.000 description 10
- 229920000742 Cotton Polymers 0.000 description 9
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 9
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 description 8
- 239000000835 fiber Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- 229920002955 Art silk Polymers 0.000 description 6
- 230000000694 effects Effects 0.000 description 6
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 5
- 229920000297 Rayon Polymers 0.000 description 5
- 239000002253 acid Substances 0.000 description 5
- 238000004078 waterproofing Methods 0.000 description 5
- 239000000839 emulsion Substances 0.000 description 4
- 235000019441 ethanol Nutrition 0.000 description 4
- AFSIMBWBBOJPJG-UHFFFAOYSA-N ethenyl octadecanoate Chemical compound CCCCCCCCCCCCCCCCCC(=O)OC=C AFSIMBWBBOJPJG-UHFFFAOYSA-N 0.000 description 4
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 4
- 239000000203 mixture Substances 0.000 description 4
- 230000002940 repellent Effects 0.000 description 4
- 210000002268 wool Anatomy 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- QYKIQEUNHZKYBP-UHFFFAOYSA-N Vinyl ether Chemical compound C=COC=C QYKIQEUNHZKYBP-UHFFFAOYSA-N 0.000 description 3
- 238000001035 drying Methods 0.000 description 3
- ORTFAQDWJHRMNX-UHFFFAOYSA-N hydroxidooxidocarbon(.) Chemical compound O[C]=O ORTFAQDWJHRMNX-UHFFFAOYSA-N 0.000 description 3
- 239000002964 rayon Substances 0.000 description 3
- 239000000344 soap Substances 0.000 description 3
- 229920001567 vinyl ester resin Polymers 0.000 description 3
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 3
- UKDKWYQGLUUPBF-UHFFFAOYSA-N 1-ethenoxyhexadecane Chemical compound CCCCCCCCCCCCCCCCOC=C UKDKWYQGLUUPBF-UHFFFAOYSA-N 0.000 description 2
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 2
- OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical group [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 2
- 125000000217 alkyl group Chemical group 0.000 description 2
- 150000008064 anhydrides Chemical class 0.000 description 2
- 239000007864 aqueous solution Substances 0.000 description 2
- 238000009835 boiling Methods 0.000 description 2
- 125000006297 carbonyl amino group Chemical group [H]N([*:2])C([*:1])=O 0.000 description 2
- 235000014113 dietary fatty acids Nutrition 0.000 description 2
- 229930195729 fatty acid Natural products 0.000 description 2
- 239000000194 fatty acid Substances 0.000 description 2
- 150000004665 fatty acids Chemical class 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- 229920002554 vinyl polymer Polymers 0.000 description 2
- DNIAPMSPPWPWGF-GSVOUGTGSA-N (R)-(-)-Propylene glycol Chemical compound C[C@@H](O)CO DNIAPMSPPWPWGF-GSVOUGTGSA-N 0.000 description 1
- WSLDOOZREJYCGB-UHFFFAOYSA-N 1,2-Dichloroethane Chemical compound ClCCCl WSLDOOZREJYCGB-UHFFFAOYSA-N 0.000 description 1
- KPZGRMZPZLOPBS-UHFFFAOYSA-N 1,3-dichloro-2,2-bis(chloromethyl)propane Chemical compound ClCC(CCl)(CCl)CCl KPZGRMZPZLOPBS-UHFFFAOYSA-N 0.000 description 1
- LAYAKLSFVAPMEL-UHFFFAOYSA-N 1-ethenoxydodecane Chemical compound CCCCCCCCCCCCOC=C LAYAKLSFVAPMEL-UHFFFAOYSA-N 0.000 description 1
- ROMNEYAQUBNRLR-UHFFFAOYSA-N 2-(4-hydroxybiphenyl-3-yl)-4-methyl-1h-isoindole-1,3(2h)-dione Chemical compound O=C1C=2C(C)=CC=CC=2C(=O)N1C(C(=CC=1)O)=CC=1C1=CC=CC=C1 ROMNEYAQUBNRLR-UHFFFAOYSA-N 0.000 description 1
- MJWPFSQVORELDX-UHFFFAOYSA-K aluminium formate Chemical compound [Al+3].[O-]C=O.[O-]C=O.[O-]C=O MJWPFSQVORELDX-UHFFFAOYSA-K 0.000 description 1
- 229910021529 ammonia Inorganic materials 0.000 description 1
- 229910052799 carbon Inorganic materials 0.000 description 1
- 235000019864 coconut oil Nutrition 0.000 description 1
- 239000003240 coconut oil Substances 0.000 description 1
- LDCRTTXIJACKKU-ARJAWSKDSA-N dimethyl maleate Chemical compound COC(=O)\C=C/C(=O)OC LDCRTTXIJACKKU-ARJAWSKDSA-N 0.000 description 1
- 229960004756 ethanol Drugs 0.000 description 1
- UJRIYYLGNDXVTA-UHFFFAOYSA-N ethenyl hexadecanoate Chemical compound CCCCCCCCCCCCCCCC(=O)OC=C UJRIYYLGNDXVTA-UHFFFAOYSA-N 0.000 description 1
- 238000009963 fulling Methods 0.000 description 1
- NKHAVTQWNUWKEO-UHFFFAOYSA-N fumaric acid monomethyl ester Natural products COC(=O)C=CC(O)=O NKHAVTQWNUWKEO-UHFFFAOYSA-N 0.000 description 1
- 150000002688 maleic acid derivatives Chemical class 0.000 description 1
- NKHAVTQWNUWKEO-IHWYPQMZSA-N methyl hydrogen fumarate Chemical compound COC(=O)\C=C/C(O)=O NKHAVTQWNUWKEO-IHWYPQMZSA-N 0.000 description 1
- 125000000896 monocarboxylic acid group Chemical group 0.000 description 1
- GQEZCXVZFLOKMC-UHFFFAOYSA-N n-alpha-hexadecene Natural products CCCCCCCCCCCCCCC=C GQEZCXVZFLOKMC-UHFFFAOYSA-N 0.000 description 1
- QIQXTHQIDYTFRH-UHFFFAOYSA-N octadecanoic acid Chemical compound CCCCCCCCCCCCCCCCCC(O)=O QIQXTHQIDYTFRH-UHFFFAOYSA-N 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 150000003222 pyridines Chemical class 0.000 description 1
- 238000009877 rendering Methods 0.000 description 1
- 235000013311 vegetables Nutrition 0.000 description 1
- 230000003612 virological effect Effects 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
- D06M15/267—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof of unsaturated carboxylic esters having amino or quaternary ammonium groups
-
- 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
- D06M15/21—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/263—Macromolecular compounds obtained by reactions only involving carbon-to-carbon unsaturated bonds of unsaturated carboxylic acids; Salts or esters thereof
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10T—TECHNICAL SUBJECTS COVERED BY FORMER US CLASSIFICATION
- Y10T442/00—Fabric [woven, knitted, or nonwoven textile or cloth, etc.]
- Y10T442/20—Coated or impregnated woven, knit, or nonwoven fabric which is not [a] associated with another preformed layer or fiber layer or, [b] with respect to woven and knit, characterized, respectively, by a particular or differential weave or knit, wherein the coating or impregnation is neither a foamed material nor a free metal or alloy layer
- Y10T442/2221—Coating or impregnation is specified as water proof
Definitions
- This invention relates to water-repellent textile material and to a process of manuiacturing the material and is a continuation in part of our application Ser. No. 94,482, flied August 5, 1936 l and entitled Water-repellent material and a process of manufacturing the material.
- textile materials can be made water-repellent in an advantageous manner by treating them with solutions or emulsions of 10.
- mixed polymerlzates which are prepared from maleic anhydride the free acid ora functional derivative thereoi and vinyl-esters of higher fatty acids (having at least 12 carbon atoms), Ior instance, according to the process described in U. s. Patent 2,047,398 for manufacturing mixed polymerisation products from maleic acid anhydrides and vinyl esters (see Example 4 oi the U. 8. Patent 2,047,398).
- These mixed polymerizates yield stable solutions or emulsions which,
- the mixed polymerisate from maleic anhydride and the vinyl ether of an aliphatic alcohol 80 of high molecular weight with at least 12 carbon atoms in the molecule as tree acid or a functional derivative thereof.
- These mixed polymerisates which as previously stated are obtainable according to the process described in U. 8. Patent 85 2,047,398 (see Example 6 for the manufacture of mixed polymers from maleic acid anhydride and vinyl others) or which may be obtained by mutual polymerisation of a functional derivative of maleic acid and 01 a vinyl ester or vinyl ether of high 40 molecular weight are composed of compounds of the formula:
- R1 and R2 stand for a member or the group consisting of COOH, C00, alkyl, CN, CONHz.
- X stands for R, OR or 0.0CR, R representing an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- the reaction upon the textile materials is executed in the following way:
- the textile material is introduced into the solution or emulsion of the mixed polymerisate and, after drying in the air, dried for a short time at a higher temperature (at about 100 C.)
- the above described process is distinguished by the fact that the fiber is not only made waterproof when treated in this manner but that it retains its waterprootness even after repeated washing to an extent which could hitherto not be attained by any process, that is to say, the mixed polymerizates above characterized are so intimately combined with the fiber that similar to fast-dyestuffs, they irreversibly adhere to the fiber.
- a web of cotton or artificial silk is impregnated with a solution of 0.5 per cent strength of the mixed polymerisate from vinyl-octodecylether and maleic-acid-dimethylester in carbon tetrachloride or a mixture thereof with alcohol, and is dried at ordinary temperature.
- the web thus treated has a very good water-repellent effect and does not lose this property even when repeatedly washed or boiled with water.
- Loose wool is impregnated as indicated in Example 1 with a solution of the mixed polymerisate from vinyl-octodecyl-ether and maleic acid in a mixture consisting of methylene chloride and ethyl-alcohol. After drying, the wool thus treated shows an enhanced water-repelling effect which it does not lose by washing.
- a web of cotton or artificial silk is impregnated with a solution in methylene chloride of the mixed polymerisate from vinyl-stearate and the semi-ester oi maieic acid with methyl alcohol, and is dried at ordinary temperature.
- the fabric thus treated has a very good waterrepellent effect and does not lose this property even after repeated washing or boiling with water.
- a web of viscose artificial silk is treated with a solution of 0.5% strength in alcohol and carbon tetrachloride of the mixed polymerisate from maleic acid and vinyloctodecyl-ether obtained by treating with steam the anhydride mixed polymerisate and dried for a short time.
- the fabric thus treated has a very good waterrepellent effect and does not lose this property even by washing or boiling.
- Loose spun rayon is impregnated with a solution of 2% strength in carbon tetrachloride of the mixed polymerisate from vinyl-stearate and maleic acid monomethyl ester, squeezed and dried.
- the spun rayon thus treated is very hydrophobe and does not lose this property by subsequent fulling.
- Piece goods consisting of a mixture of wool and spun rayon are impregnated with an aqueous solution of 1% strength of the pyridine salt of a mixed polymerisate from maleic acid and vinylhexadecyl ether and subjected for a short time to a heat treatment at 90 C.-l C.
- the material thus treated has a very good water-repellent effect and does not lose this property even by washing.
- a cotton fabric is impregnated by passage through a solution of a mixed polymerizate from viral stearate and maleic anhydride in methylene chloride, dried by exposure to air and heated for half-an-hour to about 100 C.
- the fabric thus treated is highly repellent to water and does not lose the property even after repeated washing with water and soap.
- a cotton or artificial silk fabric is impregnated with an aqueous emulsion of a mixed polymerizate from vinyl palmitate and maleic anhydride and worked up as indicated in Example 8. If desired the heat-treatment may be followed by a further treatment with aluminium formate, whereby the water-repelling effect is further increased. .This fabric also retains its water-repellent property after repeated washing.
- Loose wool is immersed into a solution of per cent strength of a mixed polymerizate from vinyl stearate and maleic anhydride, pressed and dried at 90-100 C.
- the material thus treated has an increased resistance to water.
- a fabric of cotton or artificial silk is impregnated with a solution of a mixed polymerizate from vinyl octo-decyl ether and maleic anhydride in ethylene chloride, dried and then heated for a short time at about 100 0., whereby the mixed polymerizate is intimately combined with the fibre.
- the fabric thus treated is highly repellent to water and does not lose this property even when washed with water and soap.
- the mixed polymerizate from maleic anhydride and the vinyl ether of the alcohol mixture obtainable by reduction of the coconut oil fatty acid and which contaim chiefly carbon chains with 12 to 14 carbon atoms, maybe applied in a similar manner for rendering the textile fiber highly waterproof.
- a cotton fabric is impregnated with a solution of 0.5% strength of a mixed polymerizate of maleic anhydride and vinyl dodecyl ether in carbon tetrachloride and dried subsequently, finally for a short time at a temperature of 100 C.
- the fabric treated in this manner is highly repellent to water and does not lose this property even when washed with water and soap.
- a fabric of viscose artificial silk is imof maleic anhydride and hexa-decylene in carbon.
- the material thus treated shows after drying which is finally performed for a short time at a temperature of 100 C., an excellent water-repellent eifect and a great stability to water.
- a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of compounds of the formula:
- R1 and R2 standing for a member of the group consisting of (2001-1, C00, alkyl, CN and CONI-Iz and R1 and R2 together stand for and compounds of the formula:
- X stands for a member of the group consisting of R, OR. 0.0C.R, R. standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
- X stands for a member of the group consisting of R, OR, 0.0C.R, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
- a process for waterproofing textile materials which comprises treating the textile materials with baths containing mixed polymerisates being composed of maleic acid of the formula:
- R1 and R standing for a member of the group consisting of coon, coo, alkrl. on, and com and R1 and R2 together stand for and compounds of the formula:
- X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- HzC CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- X stands for a member of the group consisting of R, OR, 0.00.3, R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
- HzC CHX wherein X stands for a member 01' the group consisting of R, OR, 0.003., R standing for an aliphatic hydrocarbon radical with at least 12 carbon atoms.
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)
Applications Claiming Priority (2)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
DE2160375X | 1936-01-04 | ||
GB464237A GB472613A (en) | 1936-03-27 | 1936-03-27 | Process for waterproofing textile materials |
Publications (1)
Publication Number | Publication Date |
---|---|
US2160375A true US2160375A (en) | 1939-05-30 |
Family
ID=32070914
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US11867836 Expired - Lifetime US2160375A (en) | 1936-01-04 | 1936-12-31 | Water-repellent textile material and process of manufacturing it |
Country Status (5)
Country | Link |
---|---|
US (1) | US2160375A (forum.php) |
BE (1) | BE416900A (forum.php) |
FR (1) | FR809289A (forum.php) |
GB (1) | GB464860A (forum.php) |
NL (1) | NL44643C (forum.php) |
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2439081A (en) * | 1944-05-05 | 1948-04-06 | Eastman Kodak Co | Polymers of cyanoacrylic acid derivatives |
US2499653A (en) * | 1946-10-17 | 1950-03-07 | American Cyanamid Co | Treatment of protein-containing textile materials and products thereof |
US2524022A (en) * | 1948-03-04 | 1950-09-26 | Montclair Res Corp | Water repellent fabrics and composition and process for making same |
US2746837A (en) * | 1951-12-28 | 1956-05-22 | Gen Aniline & Film Corp | Manufacture of leather using a modified vinyl ether-maleic anhydride copolymer, and resulting product |
US2780567A (en) * | 1954-03-22 | 1957-02-05 | Rohm & Haas | Stabilization of protein-containing textiles |
US2876895A (en) * | 1953-02-26 | 1959-03-10 | William S Port | Release agents for pressure-sensitive adhesives |
US2998326A (en) * | 1956-04-04 | 1961-08-29 | Nat Starch Products Inc | Cleaning and sizing of fabrics |
US3410720A (en) * | 1965-07-12 | 1968-11-12 | Monsanto Co | Modified textile material resistant to penetration by aqueous media |
-
0
- BE BE416900D patent/BE416900A/xx unknown
- NL NL44643D patent/NL44643C/xx active
-
1935
- 1935-09-17 GB GB2580835A patent/GB464860A/en not_active Expired
-
1936
- 1936-08-07 FR FR809289D patent/FR809289A/fr not_active Expired
- 1936-12-31 US US11867836 patent/US2160375A/en not_active Expired - Lifetime
Cited By (8)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2439081A (en) * | 1944-05-05 | 1948-04-06 | Eastman Kodak Co | Polymers of cyanoacrylic acid derivatives |
US2499653A (en) * | 1946-10-17 | 1950-03-07 | American Cyanamid Co | Treatment of protein-containing textile materials and products thereof |
US2524022A (en) * | 1948-03-04 | 1950-09-26 | Montclair Res Corp | Water repellent fabrics and composition and process for making same |
US2746837A (en) * | 1951-12-28 | 1956-05-22 | Gen Aniline & Film Corp | Manufacture of leather using a modified vinyl ether-maleic anhydride copolymer, and resulting product |
US2876895A (en) * | 1953-02-26 | 1959-03-10 | William S Port | Release agents for pressure-sensitive adhesives |
US2780567A (en) * | 1954-03-22 | 1957-02-05 | Rohm & Haas | Stabilization of protein-containing textiles |
US2998326A (en) * | 1956-04-04 | 1961-08-29 | Nat Starch Products Inc | Cleaning and sizing of fabrics |
US3410720A (en) * | 1965-07-12 | 1968-11-12 | Monsanto Co | Modified textile material resistant to penetration by aqueous media |
Also Published As
Publication number | Publication date |
---|---|
GB464860A (en) | 1937-04-19 |
BE416900A (forum.php) | 1900-01-01 |
FR809289A (fr) | 1937-02-27 |
NL44643C (forum.php) | 1900-01-01 |
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