US2610927A - Treatment of fibrous materials with polyamides - Google Patents
Treatment of fibrous materials with polyamides Download PDFInfo
- Publication number
- US2610927A US2610927A US764575A US76457547A US2610927A US 2610927 A US2610927 A US 2610927A US 764575 A US764575 A US 764575A US 76457547 A US76457547 A US 76457547A US 2610927 A US2610927 A US 2610927A
- Authority
- US
- United States
- Prior art keywords
- acid
- polyamide
- weight
- parts
- water
- 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
- 239000004952 Polyamide Substances 0.000 title claims description 33
- 229920002647 polyamide Polymers 0.000 title claims description 32
- 239000002657 fibrous material Substances 0.000 title claims description 14
- 238000011282 treatment Methods 0.000 title description 6
- 239000002253 acid Substances 0.000 claims description 20
- QAOWNCQODCNURD-UHFFFAOYSA-N Sulfuric acid Chemical compound OS(O)(=O)=O QAOWNCQODCNURD-UHFFFAOYSA-N 0.000 claims description 15
- 239000001117 sulphuric acid Substances 0.000 claims description 15
- 235000011149 sulphuric acid Nutrition 0.000 claims description 15
- 239000000463 material Substances 0.000 claims description 10
- 238000000034 method Methods 0.000 claims description 7
- 230000003472 neutralizing effect Effects 0.000 claims description 3
- XLYOFNOQVPJJNP-PWCQTSIFSA-N Tritiated water Chemical compound [3H]O[3H] XLYOFNOQVPJJNP-PWCQTSIFSA-N 0.000 claims 1
- 230000005494 condensation Effects 0.000 claims 1
- 238000009833 condensation Methods 0.000 claims 1
- 229920000768 polyamine Polymers 0.000 claims 1
- 239000000243 solution Substances 0.000 description 21
- 239000004744 fabric Substances 0.000 description 17
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 13
- GVNWZKBFMFUVNX-UHFFFAOYSA-N Adipamide Chemical compound NC(=O)CCCCC(N)=O GVNWZKBFMFUVNX-UHFFFAOYSA-N 0.000 description 9
- 230000008018 melting Effects 0.000 description 8
- 238000002844 melting Methods 0.000 description 8
- 239000004753 textile Substances 0.000 description 7
- 238000004519 manufacturing process Methods 0.000 description 5
- 229920000742 Cotton Polymers 0.000 description 4
- 229920000297 Rayon Polymers 0.000 description 4
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 150000007513 acids Chemical class 0.000 description 3
- 239000000835 fiber Substances 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- VEXZGXHMUGYJMC-UHFFFAOYSA-N hydrochloric acid Substances Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 3
- 238000011065 in-situ storage Methods 0.000 description 3
- 230000001376 precipitating effect Effects 0.000 description 3
- GRYLNZFGIOXLOG-UHFFFAOYSA-N Nitric acid Chemical compound O[N+]([O-])=O GRYLNZFGIOXLOG-UHFFFAOYSA-N 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- PMZURENOXWZQFD-UHFFFAOYSA-L Sodium Sulfate Chemical compound [Na+].[Na+].[O-]S([O-])(=O)=O PMZURENOXWZQFD-UHFFFAOYSA-L 0.000 description 2
- FAPWRFPIFSIZLT-UHFFFAOYSA-M Sodium chloride Chemical compound [Na+].[Cl-] FAPWRFPIFSIZLT-UHFFFAOYSA-M 0.000 description 2
- VHRGRCVQAFMJIZ-UHFFFAOYSA-N cadaverine Chemical compound NCCCCCN VHRGRCVQAFMJIZ-UHFFFAOYSA-N 0.000 description 2
- 229920002678 cellulose Polymers 0.000 description 2
- 239000003795 chemical substances by application Substances 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- BDAGIHXWWSANSR-UHFFFAOYSA-N methanoic acid Natural products OC=O BDAGIHXWWSANSR-UHFFFAOYSA-N 0.000 description 2
- 229940074355 nitric acid Drugs 0.000 description 2
- 229910017604 nitric acid Inorganic materials 0.000 description 2
- 229920001778 nylon Polymers 0.000 description 2
- 239000000049 pigment Substances 0.000 description 2
- 229920000642 polymer Polymers 0.000 description 2
- 239000000047 product Substances 0.000 description 2
- 229940116351 sebacate Drugs 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-L sebacate(2-) Chemical compound [O-]C(=O)CCCCCCCCC([O-])=O CXMXRPHRNRROMY-UHFFFAOYSA-L 0.000 description 2
- 239000002904 solvent Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 238000005406 washing Methods 0.000 description 2
- JIAARYAFYJHUJI-UHFFFAOYSA-L zinc dichloride Chemical compound [Cl-].[Cl-].[Zn+2] JIAARYAFYJHUJI-UHFFFAOYSA-L 0.000 description 2
- OHVLMTFVQDZYHP-UHFFFAOYSA-N 1-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-2-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical compound N1N=NC=2CN(CCC=21)C(CN1CCN(CC1)C=1C=NC(=NC=1)NCC1=CC(=CC=C1)OC(F)(F)F)=O OHVLMTFVQDZYHP-UHFFFAOYSA-N 0.000 description 1
- LDXJRKWFNNFDSA-UHFFFAOYSA-N 2-(2,4,6,7-tetrahydrotriazolo[4,5-c]pyridin-5-yl)-1-[4-[2-[[3-(trifluoromethoxy)phenyl]methylamino]pyrimidin-5-yl]piperazin-1-yl]ethanone Chemical group C1CN(CC2=NNN=C21)CC(=O)N3CCN(CC3)C4=CN=C(N=C4)NCC5=CC(=CC=C5)OC(F)(F)F LDXJRKWFNNFDSA-UHFFFAOYSA-N 0.000 description 1
- XRKBQVGBWJWJJJ-UHFFFAOYSA-N 2-aminooctadecanoic acid Chemical compound CCCCCCCCCCCCCCCCC(N)C(O)=O XRKBQVGBWJWJJJ-UHFFFAOYSA-N 0.000 description 1
- OSWFIVFLDKOXQC-UHFFFAOYSA-N 4-(3-methoxyphenyl)aniline Chemical compound COC1=CC=CC(C=2C=CC(N)=CC=2)=C1 OSWFIVFLDKOXQC-UHFFFAOYSA-N 0.000 description 1
- UFFRSDWQMJYQNE-UHFFFAOYSA-N 6-azaniumylhexylazanium;hexanedioate Chemical compound [NH3+]CCCCCC[NH3+].[O-]C(=O)CCCCC([O-])=O UFFRSDWQMJYQNE-UHFFFAOYSA-N 0.000 description 1
- 229910002651 NO3 Inorganic materials 0.000 description 1
- NHNBFGGVMKEFGY-UHFFFAOYSA-N Nitrate Chemical compound [O-][N+]([O-])=O NHNBFGGVMKEFGY-UHFFFAOYSA-N 0.000 description 1
- 230000001464 adherent effect Effects 0.000 description 1
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical class OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 1
- 125000001931 aliphatic group Chemical group 0.000 description 1
- 239000003513 alkali Substances 0.000 description 1
- 125000005263 alkylenediamine group Chemical group 0.000 description 1
- 150000001408 amides Chemical class 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
- 239000012736 aqueous medium Substances 0.000 description 1
- 239000007864 aqueous solution Substances 0.000 description 1
- 239000001913 cellulose Substances 0.000 description 1
- 229920002301 cellulose acetate Polymers 0.000 description 1
- 239000003153 chemical reaction reagent Substances 0.000 description 1
- 238000000975 co-precipitation Methods 0.000 description 1
- 238000010622 cold drawing Methods 0.000 description 1
- 239000002131 composite material Substances 0.000 description 1
- 150000001875 compounds Chemical class 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- TTWTTWXDBDZRCV-UHFFFAOYSA-N decane-1,10-diamine;decanedioic acid Chemical compound NCCCCCCCCCCN.OC(=O)CCCCCCCCC(O)=O TTWTTWXDBDZRCV-UHFFFAOYSA-N 0.000 description 1
- 230000001627 detrimental effect Effects 0.000 description 1
- 238000001704 evaporation Methods 0.000 description 1
- 230000008020 evaporation Effects 0.000 description 1
- 238000009950 felting Methods 0.000 description 1
- 238000007730 finishing process Methods 0.000 description 1
- 235000019253 formic acid Nutrition 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 238000004900 laundering Methods 0.000 description 1
- 239000000203 mixture Substances 0.000 description 1
- 150000003839 salts Chemical class 0.000 description 1
- 239000011780 sodium chloride Substances 0.000 description 1
- 235000011121 sodium hydroxide Nutrition 0.000 description 1
- 229910052938 sodium sulfate Inorganic materials 0.000 description 1
- 235000011152 sodium sulphate Nutrition 0.000 description 1
- 230000008961 swelling Effects 0.000 description 1
- DXNCZXXFRKPEPY-UHFFFAOYSA-N tridecanedioic acid Chemical compound OC(=O)CCCCCCCCCCCC(O)=O DXNCZXXFRKPEPY-UHFFFAOYSA-N 0.000 description 1
- 239000012463 white pigment Substances 0.000 description 1
- 239000002023 wood Substances 0.000 description 1
- 210000002268 wool Anatomy 0.000 description 1
- 235000005074 zinc chloride Nutrition 0.000 description 1
- 239000011592 zinc chloride Substances 0.000 description 1
Classifications
-
- D—TEXTILES; PAPER
- D21—PAPER-MAKING; PRODUCTION OF CELLULOSE
- D21H—PULP COMPOSITIONS; PREPARATION THEREOF NOT COVERED BY SUBCLASSES D21C OR D21D; IMPREGNATING OR COATING OF PAPER; TREATMENT OF FINISHED PAPER NOT COVERED BY CLASS B31 OR SUBCLASS D21G; PAPER NOT OTHERWISE PROVIDED FOR
- D21H17/00—Non-fibrous material added to the pulp, characterised by its constitution; Paper-impregnating material characterised by its constitution
- D21H17/20—Macromolecular organic compounds
- D21H17/33—Synthetic macromolecular compounds
- D21H17/46—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D21H17/54—Synthetic macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds obtained by reactions forming in the main chain of the macromolecule a linkage containing nitrogen
- D21H17/55—Polyamides; Polyaminoamides; Polyester-amides
-
- D—TEXTILES; PAPER
- D06—TREATMENT OF TEXTILES OR THE LIKE; LAUNDERING; FLEXIBLE MATERIALS NOT OTHERWISE PROVIDED FOR
- D06N—WALL, FLOOR, OR LIKE COVERING MATERIALS, e.g. LINOLEUM, OILCLOTH, ARTIFICIAL LEATHER, ROOFING FELT, CONSISTING OF A FIBROUS WEB COATED WITH A LAYER OF MACROMOLECULAR MATERIAL; FLEXIBLE SHEET MATERIAL NOT OTHERWISE PROVIDED FOR
- D06N3/00—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof
- D06N3/12—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins
- D06N3/125—Artificial leather, oilcloth or other material obtained by covering fibrous webs with macromolecular material, e.g. resins, rubber or derivatives thereof with macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds, e.g. gelatine proteins with polyamides
-
- 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
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S8/00—Bleaching and dyeing; fluid treatment and chemical modification of textiles and fibers
- Y10S8/21—Nylon
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31739—Nylon type
-
- 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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/31504—Composite [nonstructural laminate]
- Y10T428/31725—Of polyamide
- Y10T428/31779—Next to cellulosic
-
- 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
- Y10T442/2033—Coating or impregnation formed in situ [e.g., by interfacial condensation, coagulation, precipitation, etc.]
Definitions
- j ⁇ the term "nylon" is not customarily applied to synthetic polyamid'es which are water-soluble.
- present invention is concerned with XVHtGY-iHS OI-J uble, high molecular weight or fibre-forming polyamides soluble in "strong acid such as are described in United States patent specification No. 2,071,250, Wallace H. Car-others, patented” February 16 ,'193'7;"United' States patent specification No. 2,071,253, Wallace H. Carother's, pat,- tented February 16, '1937 and United States pat ent specification No. 2,130,948, Wallace H. Carothers, patented September 20, 1938. I,
- the principal object oi the 'presentinvention is to deposit a waterdnsoluble' synthetic linear polyamide on divided, adherent particles- "wate -i solubl syntheticlinear polyamides will dissolve incom I paratively istron'g'acid and may be precipitated therefrom by the action-of an aqueous mediumand this .fact-is utilised in the present invention 'to precipitate the polyamide on cellulos'ic or non-cellulosic fibrous material's.
- the polyamid'e adheres firmly to the fibres producing a white, opaque effect which is 'fast to laundering and does not render the fibrous material hard or harsh,
- the material on which the water insoluble linear polyam-ide hasfbeen precipitated can -b'e passed with or without tension over heated rollers to fuse the polyamide.
- This is particularly applicable to synthetic linear polyamides of low melting point. It will .be apparent from the aforementioned patent specifications that there is a wide range of water-insoluble synthetic linear polyamides of various melting points. Any of theseeither singly or mixed, soluble in strong acid, may beeuse in carrying out the present invention.
- the fibrous materials which the treated are cotton, linen, wool-naturalj silk; viscose yarn, cellulose acetate or mixtures of any of these with one'another-or with synthetic linear polyamide fibresbut the reagent should be'chosen' so as not to damage the m'ater ial treated.
- the 'fi'brous' materiah may be in the for m of fabrics, woven *or knitted, o'i-fin any other form, eg as yarn, fibre or sheet; Co,n tinuoussheet materialsuchas paper or wood may also be treated with water-insoluble syn- 'thetic'linear polyamide's by this method.
- Fabric which is treated in accordance with the present invention- may be rendered crease: resistant by means or resinous condensation products and, if required; after-treated with swelling agents, or. the "treated fabric may be subjected to other finishing processes.
- treated 1 with gwateri-n'soluble synthetic -l'inear polyamides in accordance with. the pr'e'sent invention resists shrinking "and' felting after' mill- Among the;strong acidsiwhieh may beu'sed are sulphuric.
- any otheri'strong acids known-to Wool centrated is the acid, the more readily will the polyamide be dissolved but on the other hand the more concentrated acids; hydrolyse poly- The cn centration of the acid used must be sufficient to enable the polyamide to dissolve. The more conamides more readily and this must be taken into consideration in the treatment of textile materials with such solutions. Moreover, the concentration of acid which can be used obviously depends upon the strength of the acid. In the case of formic acid, for example, this may be.
- Example-3 2 parts by weight of polytetramethylenediamine adipamide of melting point 278 C.
- cotton or viscose fabric is run through this solution and nipped, off, after which it is washed off in water and neutralised.
- the so-treated fabric is then run through 140 Tw. sulphuric acid for '5 seconds after which it is washed off again in used anhydrous whereas the form of sulphuric acid commercially known as concentrated sul phuric acid cannot safely be used.
- 'A co'nvenient way of treating a textile fabric is to pass it through a solution of the polyamide in sulphuric acid, squeeze it an'dthen'run it into water, whereupon the polyamide is deposited on the fabric as a white pigment.
- the squeezing will generally be such as to leave 100% by weight of solution calculated on the dryweight of the fabric on the textile;
- Other pigments which will dissolve in the acid and will be precipitated therefrom by the addition of water (or substances soluble in the acid from which pigments are formed and precipitated by water) may be added to the solution so that co-precipitation takes place.
- a resist may be printed on the fabric before impregnation with the acid solution.
- An example of such resists which are preferably insoluble in strong acid, is cellulose'nitrate.
- Other resists insoluble in strong acid are well known.
- Fabrics which have been treated in accordance with the present invention may be given other known treatments such as parchmentising, for example with sulphuric acid or zinc chloride, or other known parchmentising agents, or'may be waterproofed, for example'with one of the known, pyridiniurn compounds.
- Example 1 2 parts by weight of polyhexamethylenediamine adipamide having a melting point of 278- C. are dissolved in 27 parts .by. weight of 70 Tw. sulphuric acid. A cotton or viscose fabric-is run through thissolution and nipped 01f, after which it is washed off in water-and neutralised.
- a -fine-cambric is'run through a solution of '1 part by weight of"polyethylenediamine"sebacate of melting point 254 C.' the manufacture of which is described in United States patent spe'ci fication 'No. 2,130;948 *'in 25 partsby 'w'eight' of commercial --hydrochloric acid containing 3 by weightof antimony rtrich'lorid'e, passed through water and neutralised. This treatment gives a stifi parchmentised eflect.
- Example 4 2 'parts by weight of 'an interpolyamide prepared by heating equimolecular proportions of hexamethylenediamine adipamide and decamethylene diammonium sebacate having a softeningpoint of 112 C., the manufacture of whichis'described in British patent specification No. 559,514, are dissolved in 27 parts by weight of 70 Tw. sulphuric acid. A cotton or viscose fabric is run through this solution and nipped off, after which it is washed off in water and neutralised.- The fabric is then run over a hot roller, with or without stretching, at a temperature high enough to melt the polyamide.
- Paper is impregnated with'a solution, in 25 parts by weight of 70- Tw. sulphuric acid, of 1 part by weight of a polymerprepared by heating hexamethylene diammonium adipate and aminostearic acid and having a melting point of 130 C. and an intrinsic viscosity of 0.98, the manufacture of which is described in British patent specificationNo. 559,514;
- the paper is then im-' mersed in water to precipitate the polyamide thereon. Sheets of paper thus treated can be banded together by heating an assembly of them toa suflicient temperature to bond the polyamide.
- Example 6 1 to.2 parts-by weight of the polyamide prepared from pentamethylenediamine and brassilic acid having a melting point of 176 C., the man-' ufacture of which is described in United States patent specification No. 2,130,948, are dissolved or dispersed in 25 parts'by weight of sulphuric acid of Tw. To the solution is added loose fibre of any description after which the polyamide is precipitated with' water, washed and neutralisedp The mass of-polyamide covered fibres is then heated above the melting point ofthe-polyamide and pressedso that a composite mass of polyamide and fibres is obtained.
- the mass can be rolled into any required thickness and then heated to melt the the-precipitant"for the polyamide wemay use any a ueous Iiquorin' which the polyamide is sub-' stantially insoluble and with which the solution of polyamide is miscible and which does not have any detrimental effect upon the fibrous material treated such as dilute aqueous alkali, e. g. caustic soda or aqueous solutions containing inert salts such as sodium chloride or sodium sulphate.
- a ueous Iiquorin' which the polyamide is sub-' stantially insoluble and with which the solution of polyamide is miscible and which does not have any detrimental effect upon the fibrous material treated such as dilute aqueous alkali, e. g. caustic soda or aqueous solutions containing inert salts such as sodium chloride or sodium sulphate.
- Process of treating fibrous material which consists in applying to it a solution of a polyalkylenediamine adipamide in sulphuric acid, removing excess solution and then passing the material into water and thereby precipitating in situ the said polyalkylenediamine adipamide in fine particular form, and neutralising the fibrous material.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Life Sciences & Earth Sciences (AREA)
- Proteomics, Peptides & Aminoacids (AREA)
- Dispersion Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Chemical Or Physical Treatment Of Fibers (AREA)
- Paper (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
GB244849X | 1943-03-08 |
Publications (1)
Publication Number | Publication Date |
---|---|
US2610927A true US2610927A (en) | 1952-09-16 |
Family
ID=10212410
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US764575A Expired - Lifetime US2610927A (en) | 1943-03-08 | 1947-07-29 | Treatment of fibrous materials with polyamides |
Country Status (6)
Country | Link |
---|---|
US (1) | US2610927A (enrdf_load_stackoverflow) |
CH (1) | CH244849A (enrdf_load_stackoverflow) |
DE (1) | DE807395C (enrdf_load_stackoverflow) |
FR (1) | FR931236A (enrdf_load_stackoverflow) |
GB (1) | GB567043A (enrdf_load_stackoverflow) |
NL (1) | NL61278C (enrdf_load_stackoverflow) |
Cited By (19)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734001A (en) * | 1956-02-07 | Setting and stiffening fabrics | ||
US2859135A (en) * | 1949-12-01 | 1958-11-04 | Monsanto Chemicals | Treatment of textile fibers |
US2864151A (en) * | 1952-01-01 | 1958-12-16 | Bihaly Lajos | Fused fabric assemblies |
US2890136A (en) * | 1955-10-28 | 1959-06-09 | Canadian Hanson And Van Winkle | Sisal buff resin impregnation method |
US2890137A (en) * | 1955-10-28 | 1959-06-09 | Canadian Hanson | Sisal buff oil impregnation method |
US2917891A (en) * | 1953-09-01 | 1959-12-22 | Columbian Rope Co | Synthetic rope structure and method of making same |
DE1092877B (de) * | 1956-01-21 | 1960-11-17 | Inventa A G Fuer Forschung & P | Verfahren zur Erhoehung der Schiebefestigkeit von fadenfoermigen Gebilden aus synthetischen linearen Polyamiden |
US2993826A (en) * | 1956-03-08 | 1961-07-25 | Yardney International Corp | Surface conditioners for nylon |
US3011915A (en) * | 1958-03-17 | 1961-12-05 | Capskar Inc | Method of coating cloth with a nylon solution |
US3077423A (en) * | 1960-02-19 | 1963-02-12 | Chicopee Mfg Corp | Wiping materials and methods of making the same |
US3322824A (en) * | 1964-07-02 | 1967-05-30 | Celanese Corp | Compositions containing a polytereph-thalamide and a hydrocarbon-substituted sulfonicacid, and process utilizing the same in making shaped articles |
US3393111A (en) * | 1963-10-04 | 1968-07-16 | Hofmann Erwin | Process of uniting strands of a plaited polyamide article |
US3447308A (en) * | 1965-10-06 | 1969-06-03 | American Enka Corp | Multifilament yarns for reinforcing elastic articles |
US3449287A (en) * | 1965-04-07 | 1969-06-10 | Bonded Fibre Fab | Polyamide plasticized with urea for use in fusible compositions |
US3537880A (en) * | 1967-01-31 | 1970-11-03 | Fmc Corp | Heat-bondable fibers |
US3944700A (en) * | 1973-06-22 | 1976-03-16 | L. Mombers B.V. | Method of manufacturing polyamide coated textile material and to the textile material made according to the method |
US4350006A (en) * | 1966-01-07 | 1982-09-21 | Toray Industries, Inc. | Synthetic filaments and the like |
US4714736A (en) * | 1986-05-29 | 1987-12-22 | The Dow Chemical Company | Stable polyamide solutions |
US5626969A (en) * | 1992-02-21 | 1997-05-06 | General Binding Corporation | Method of manufacturing film for lamination |
Families Citing this family (1)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3164194A (en) * | 1963-06-28 | 1965-01-05 | Inter American Transp Equipmen | Sugar cane cart wheel |
Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US1640596A (en) * | 1921-07-18 | 1927-08-30 | Celanese Corp | Treatment of fabrics, paper, and other materials |
US2188332A (en) * | 1937-02-15 | 1940-01-30 | Du Pont | Flexible coated article |
US2302332A (en) * | 1940-04-09 | 1942-11-17 | Du Pont | Coating process |
US2342387A (en) * | 1939-10-24 | 1944-02-22 | Du Pont | Process for preparing coating compositions |
US2359878A (en) * | 1941-08-09 | 1944-10-10 | Du Pont | Polymeric compositions |
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0
- NL NL61278D patent/NL61278C/xx active
-
1943
- 1943-03-08 GB GB3704/43A patent/GB567043A/en not_active Expired
-
1944
- 1944-03-17 CH CH244849D patent/CH244849A/de unknown
-
1946
- 1946-07-24 FR FR931236D patent/FR931236A/fr not_active Expired
-
1947
- 1947-07-29 US US764575A patent/US2610927A/en not_active Expired - Lifetime
-
1948
- 1948-12-11 DE DEP24392D patent/DE807395C/de not_active Expired
Patent Citations (5)
Publication number | Priority date | Publication date | Assignee | Title |
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US1640596A (en) * | 1921-07-18 | 1927-08-30 | Celanese Corp | Treatment of fabrics, paper, and other materials |
US2188332A (en) * | 1937-02-15 | 1940-01-30 | Du Pont | Flexible coated article |
US2342387A (en) * | 1939-10-24 | 1944-02-22 | Du Pont | Process for preparing coating compositions |
US2302332A (en) * | 1940-04-09 | 1942-11-17 | Du Pont | Coating process |
US2359878A (en) * | 1941-08-09 | 1944-10-10 | Du Pont | Polymeric compositions |
Cited By (20)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2734001A (en) * | 1956-02-07 | Setting and stiffening fabrics | ||
US2859135A (en) * | 1949-12-01 | 1958-11-04 | Monsanto Chemicals | Treatment of textile fibers |
US2864151A (en) * | 1952-01-01 | 1958-12-16 | Bihaly Lajos | Fused fabric assemblies |
US2917891A (en) * | 1953-09-01 | 1959-12-22 | Columbian Rope Co | Synthetic rope structure and method of making same |
US2890136A (en) * | 1955-10-28 | 1959-06-09 | Canadian Hanson And Van Winkle | Sisal buff resin impregnation method |
US2890137A (en) * | 1955-10-28 | 1959-06-09 | Canadian Hanson | Sisal buff oil impregnation method |
DE1092877B (de) * | 1956-01-21 | 1960-11-17 | Inventa A G Fuer Forschung & P | Verfahren zur Erhoehung der Schiebefestigkeit von fadenfoermigen Gebilden aus synthetischen linearen Polyamiden |
US2993826A (en) * | 1956-03-08 | 1961-07-25 | Yardney International Corp | Surface conditioners for nylon |
US3011915A (en) * | 1958-03-17 | 1961-12-05 | Capskar Inc | Method of coating cloth with a nylon solution |
US3077423A (en) * | 1960-02-19 | 1963-02-12 | Chicopee Mfg Corp | Wiping materials and methods of making the same |
US3393111A (en) * | 1963-10-04 | 1968-07-16 | Hofmann Erwin | Process of uniting strands of a plaited polyamide article |
US3322824A (en) * | 1964-07-02 | 1967-05-30 | Celanese Corp | Compositions containing a polytereph-thalamide and a hydrocarbon-substituted sulfonicacid, and process utilizing the same in making shaped articles |
US3449287A (en) * | 1965-04-07 | 1969-06-10 | Bonded Fibre Fab | Polyamide plasticized with urea for use in fusible compositions |
US3447308A (en) * | 1965-10-06 | 1969-06-03 | American Enka Corp | Multifilament yarns for reinforcing elastic articles |
USRE29382E (en) * | 1965-10-06 | 1977-09-06 | Akzona Incorporated | Multifilament yarns for reinforcing articles |
US4350006A (en) * | 1966-01-07 | 1982-09-21 | Toray Industries, Inc. | Synthetic filaments and the like |
US3537880A (en) * | 1967-01-31 | 1970-11-03 | Fmc Corp | Heat-bondable fibers |
US3944700A (en) * | 1973-06-22 | 1976-03-16 | L. Mombers B.V. | Method of manufacturing polyamide coated textile material and to the textile material made according to the method |
US4714736A (en) * | 1986-05-29 | 1987-12-22 | The Dow Chemical Company | Stable polyamide solutions |
US5626969A (en) * | 1992-02-21 | 1997-05-06 | General Binding Corporation | Method of manufacturing film for lamination |
Also Published As
Publication number | Publication date |
---|---|
CH244849A (de) | 1946-10-15 |
GB567043A (en) | 1945-01-25 |
NL61278C (enrdf_load_stackoverflow) | 1900-01-01 |
DE807395C (de) | 1951-06-28 |
FR931236A (fr) | 1948-02-17 |
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