US3751290A - Nonwoven fabrics - Google Patents
Nonwoven fabrics Download PDFInfo
- Publication number
- US3751290A US3751290A US00154685A US3751290DA US3751290A US 3751290 A US3751290 A US 3751290A US 00154685 A US00154685 A US 00154685A US 3751290D A US3751290D A US 3751290DA US 3751290 A US3751290 A US 3751290A
- Authority
- US
- United States
- Prior art keywords
- percent
- integer
- methylolated
- group
- polyureaurethane
- 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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- 239000004745 nonwoven fabric Substances 0.000 title claims description 39
- 229920000642 polymer Polymers 0.000 claims abstract description 59
- 229920000162 poly(ureaurethane) Polymers 0.000 claims abstract description 36
- 229920002396 Polyurea Polymers 0.000 claims abstract description 26
- 239000011230 binding agent Substances 0.000 claims description 31
- 239000000835 fiber Substances 0.000 claims description 25
- 229920005989 resin Polymers 0.000 claims description 13
- 239000011347 resin Substances 0.000 claims description 13
- 229920000728 polyester Polymers 0.000 claims description 6
- 229920001778 nylon Polymers 0.000 claims description 5
- 229920003043 Cellulose fiber Polymers 0.000 claims description 2
- 239000004753 textile Substances 0.000 abstract description 34
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical group O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract description 27
- 229910052739 hydrogen Inorganic materials 0.000 abstract description 16
- 239000001257 hydrogen Substances 0.000 abstract description 13
- 238000000034 method Methods 0.000 abstract description 12
- UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 abstract description 10
- 125000002947 alkylene group Chemical group 0.000 abstract description 9
- 125000004432 carbon atom Chemical group C* 0.000 abstract description 8
- 239000007788 liquid Substances 0.000 abstract description 7
- 125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 abstract description 7
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract description 4
- CBOIHMRHGLHBPB-UHFFFAOYSA-N hydroxymethyl Chemical compound O[CH2] CBOIHMRHGLHBPB-UHFFFAOYSA-N 0.000 abstract 7
- 235000019256 formaldehyde Nutrition 0.000 abstract 1
- MYWUZJCMWCOHBA-VIFPVBQESA-N methamphetamine Chemical compound CN[C@@H](C)CC1=CC=CC=C1 MYWUZJCMWCOHBA-VIFPVBQESA-N 0.000 abstract 1
- 239000000243 solution Substances 0.000 description 37
- 239000000463 material Substances 0.000 description 20
- MTHSVFCYNBDYFN-UHFFFAOYSA-N diethylene glycol Chemical compound OCCOCCO MTHSVFCYNBDYFN-UHFFFAOYSA-N 0.000 description 15
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 15
- ONDPHDOFVYQSGI-UHFFFAOYSA-N zinc nitrate Chemical compound [Zn+2].[O-][N+]([O-])=O.[O-][N+]([O-])=O ONDPHDOFVYQSGI-UHFFFAOYSA-N 0.000 description 14
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 description 13
- 239000004202 carbamide Substances 0.000 description 13
- 239000000203 mixture Substances 0.000 description 13
- 150000001414 amino alcohols Chemical class 0.000 description 12
- 150000004985 diamines Chemical class 0.000 description 11
- 239000004744 fabric Substances 0.000 description 11
- 239000000047 product Substances 0.000 description 11
- 229920000297 Rayon Polymers 0.000 description 10
- 238000002360 preparation method Methods 0.000 description 10
- IJGRMHOSHXDMSA-UHFFFAOYSA-N Atomic nitrogen Chemical compound N#N IJGRMHOSHXDMSA-UHFFFAOYSA-N 0.000 description 8
- -1 decaethylene glycol diamine Chemical class 0.000 description 8
- 239000002964 rayon Substances 0.000 description 8
- 239000007787 solid Substances 0.000 description 8
- 239000007864 aqueous solution Substances 0.000 description 7
- 238000005406 washing Methods 0.000 description 7
- GIAFURWZWWWBQT-UHFFFAOYSA-N 2-(2-aminoethoxy)ethanol Chemical compound NCCOCCO GIAFURWZWWWBQT-UHFFFAOYSA-N 0.000 description 6
- 238000006243 chemical reaction Methods 0.000 description 6
- 239000003795 chemical substances by application Substances 0.000 description 5
- 238000002845 discoloration Methods 0.000 description 5
- 229910052757 nitrogen Inorganic materials 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- 229920000742 Cotton Polymers 0.000 description 4
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical group OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 4
- 239000000853 adhesive Substances 0.000 description 4
- QSHDDOUJBYECFT-UHFFFAOYSA-N mercury Chemical compound [Hg] QSHDDOUJBYECFT-UHFFFAOYSA-N 0.000 description 4
- 229910052753 mercury Inorganic materials 0.000 description 4
- WGYKZJWCGVVSQN-UHFFFAOYSA-N propylamine Chemical compound CCCN WGYKZJWCGVVSQN-UHFFFAOYSA-N 0.000 description 4
- 238000010992 reflux Methods 0.000 description 4
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 3
- HEMHJVSKTPXQMS-UHFFFAOYSA-M Sodium hydroxide Chemical compound [OH-].[Na+] HEMHJVSKTPXQMS-UHFFFAOYSA-M 0.000 description 3
- 239000003377 acid catalyst Substances 0.000 description 3
- 230000001070 adhesive effect Effects 0.000 description 3
- 239000003054 catalyst Substances 0.000 description 3
- 239000007795 chemical reaction product Substances 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 238000005108 dry cleaning Methods 0.000 description 3
- 239000003995 emulsifying agent Substances 0.000 description 3
- 239000000839 emulsion Substances 0.000 description 3
- 239000011541 reaction mixture Substances 0.000 description 3
- 229920002994 synthetic fiber Polymers 0.000 description 3
- 239000012209 synthetic fiber Substances 0.000 description 3
- ASDQMECUMYIVBG-UHFFFAOYSA-N 2-[2-(2-aminoethoxy)ethoxy]ethanol Chemical compound NCCOCCOCCO ASDQMECUMYIVBG-UHFFFAOYSA-N 0.000 description 2
- NLXLAEXVIDQMFP-UHFFFAOYSA-N Ammonia chloride Chemical compound [NH4+].[Cl-] NLXLAEXVIDQMFP-UHFFFAOYSA-N 0.000 description 2
- CURLTUGMZLYLDI-UHFFFAOYSA-N Carbon dioxide Chemical compound O=C=O CURLTUGMZLYLDI-UHFFFAOYSA-N 0.000 description 2
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 2
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 2
- TWRXJAOTZQYOKJ-UHFFFAOYSA-L Magnesium chloride Chemical compound [Mg+2].[Cl-].[Cl-] TWRXJAOTZQYOKJ-UHFFFAOYSA-L 0.000 description 2
- CSNNHWWHGAXBCP-UHFFFAOYSA-L Magnesium sulfate Chemical compound [Mg+2].[O-][S+2]([O-])([O-])[O-] CSNNHWWHGAXBCP-UHFFFAOYSA-L 0.000 description 2
- 239000004677 Nylon Substances 0.000 description 2
- 229920005822 acrylic binder Polymers 0.000 description 2
- 150000001412 amines Chemical class 0.000 description 2
- 229910021529 ammonia Inorganic materials 0.000 description 2
- 230000015572 biosynthetic process Effects 0.000 description 2
- 235000011089 carbon dioxide Nutrition 0.000 description 2
- 150000001875 compounds Chemical class 0.000 description 2
- 239000003599 detergent Substances 0.000 description 2
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 description 2
- 230000000694 effects Effects 0.000 description 2
- 239000008098 formaldehyde solution Substances 0.000 description 2
- 238000010438 heat treatment Methods 0.000 description 2
- NAQMVNRVTILPCV-UHFFFAOYSA-N hexane-1,6-diamine Chemical compound NCCCCCCN NAQMVNRVTILPCV-UHFFFAOYSA-N 0.000 description 2
- WSFSSNUMVMOOMR-NJFSPNSNSA-N methanone Chemical compound O=[14CH2] WSFSSNUMVMOOMR-NJFSPNSNSA-N 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- 229920001451 polypropylene glycol Polymers 0.000 description 2
- 239000000376 reactant Substances 0.000 description 2
- 238000003756 stirring Methods 0.000 description 2
- XIOUDVJTOYVRTB-UHFFFAOYSA-N 1-(1-adamantyl)-3-aminothiourea Chemical compound C1C(C2)CC3CC2CC1(NC(=S)NN)C3 XIOUDVJTOYVRTB-UHFFFAOYSA-N 0.000 description 1
- NSOAQRMLVFRWIT-UHFFFAOYSA-N 1-ethenoxydecane Chemical group CCCCCCCCCCOC=C NSOAQRMLVFRWIT-UHFFFAOYSA-N 0.000 description 1
- IOSXLUZXMXORMX-UHFFFAOYSA-N 1-ethenoxypentane Chemical group CCCCCOC=C IOSXLUZXMXORMX-UHFFFAOYSA-N 0.000 description 1
- LCZVSXRMYJUNFX-UHFFFAOYSA-N 2-[2-(2-hydroxypropoxy)propoxy]propan-1-ol Chemical compound CC(O)COC(C)COC(C)CO LCZVSXRMYJUNFX-UHFFFAOYSA-N 0.000 description 1
- KRPRVQWGKLEFKN-UHFFFAOYSA-N 3-(3-aminopropoxy)propan-1-amine Chemical compound NCCCOCCCN KRPRVQWGKLEFKN-UHFFFAOYSA-N 0.000 description 1
- GJMPSRSMBJLKKB-UHFFFAOYSA-N 3-methylphenylacetic acid Chemical compound CC1=CC=CC(CC(O)=O)=C1 GJMPSRSMBJLKKB-UHFFFAOYSA-N 0.000 description 1
- 239000009261 D 400 Substances 0.000 description 1
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-N Hydrochloric acid Chemical compound Cl VEXZGXHMUGYJMC-UHFFFAOYSA-N 0.000 description 1
- 229920000459 Nitrile rubber Polymers 0.000 description 1
- IGFHQQFPSIBGKE-UHFFFAOYSA-N Nonylphenol Natural products CCCCCCCCCC1=CC=C(O)C=C1 IGFHQQFPSIBGKE-UHFFFAOYSA-N 0.000 description 1
- 229930040373 Paraformaldehyde Natural products 0.000 description 1
- 229920003171 Poly (ethylene oxide) Polymers 0.000 description 1
- 239000004698 Polyethylene Substances 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 239000004372 Polyvinyl alcohol Substances 0.000 description 1
- 239000004902 Softening Agent Substances 0.000 description 1
- 239000002253 acid Substances 0.000 description 1
- 239000000654 additive Substances 0.000 description 1
- DIZPMCHEQGEION-UHFFFAOYSA-H aluminium sulfate (anhydrous) Chemical compound [Al+3].[Al+3].[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O.[O-]S([O-])(=O)=O DIZPMCHEQGEION-UHFFFAOYSA-H 0.000 description 1
- 235000019270 ammonium chloride Nutrition 0.000 description 1
- SOIFLUNRINLCBN-UHFFFAOYSA-N ammonium thiocyanate Chemical compound [NH4+].[S-]C#N SOIFLUNRINLCBN-UHFFFAOYSA-N 0.000 description 1
- 238000005915 ammonolysis reaction Methods 0.000 description 1
- NTXGQCSETZTARF-UHFFFAOYSA-N buta-1,3-diene;prop-2-enenitrile Chemical compound C=CC=C.C=CC#N NTXGQCSETZTARF-UHFFFAOYSA-N 0.000 description 1
- 235000013351 cheese Nutrition 0.000 description 1
- 230000001427 coherent effect Effects 0.000 description 1
- 239000007859 condensation product Substances 0.000 description 1
- 229920001577 copolymer Polymers 0.000 description 1
- 230000003247 decreasing effect Effects 0.000 description 1
- 230000008021 deposition Effects 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-M dihydrogenphosphate Chemical compound OP(O)([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-M 0.000 description 1
- 238000007598 dipping method Methods 0.000 description 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 1
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 1
- 239000004615 ingredient Substances 0.000 description 1
- 238000010409 ironing Methods 0.000 description 1
- 239000006193 liquid solution Substances 0.000 description 1
- RLSSMJSEOOYNOY-UHFFFAOYSA-N m-cresol Chemical compound CC1=CC=CC(O)=C1 RLSSMJSEOOYNOY-UHFFFAOYSA-N 0.000 description 1
- 229910001629 magnesium chloride Inorganic materials 0.000 description 1
- 229910052943 magnesium sulfate Inorganic materials 0.000 description 1
- 235000019341 magnesium sulphate Nutrition 0.000 description 1
- 229940100630 metacresol Drugs 0.000 description 1
- VIJMMQUAJQEELS-UHFFFAOYSA-N n,n-bis(ethenyl)ethenamine Chemical compound C=CN(C=C)C=C VIJMMQUAJQEELS-UHFFFAOYSA-N 0.000 description 1
- SNQQPOLDUKLAAF-UHFFFAOYSA-N nonylphenol Chemical compound CCCCCCCCCC1=CC=CC=C1O SNQQPOLDUKLAAF-UHFFFAOYSA-N 0.000 description 1
- 125000002347 octyl group Chemical group [H]C([*])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])C([H])([H])[H] 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 229920002866 paraformaldehyde Polymers 0.000 description 1
- 229920000058 polyacrylate Polymers 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000573 polyethylene Polymers 0.000 description 1
- 229920005596 polymer binder Polymers 0.000 description 1
- 239000002491 polymer binding agent Substances 0.000 description 1
- 229920000098 polyolefin Polymers 0.000 description 1
- 229920002689 polyvinyl acetate Polymers 0.000 description 1
- 239000011118 polyvinyl acetate Substances 0.000 description 1
- 229920002451 polyvinyl alcohol Polymers 0.000 description 1
- 239000004800 polyvinyl chloride Substances 0.000 description 1
- 229920000915 polyvinyl chloride Polymers 0.000 description 1
- 238000003825 pressing Methods 0.000 description 1
- 238000007639 printing Methods 0.000 description 1
- 238000007493 shaping process Methods 0.000 description 1
- 239000004334 sorbic acid Substances 0.000 description 1
- 238000005507 spraying Methods 0.000 description 1
- 229920001187 thermosetting polymer Polymers 0.000 description 1
- 229940117957 triethanolamine hydrochloride Drugs 0.000 description 1
- ZIBGPFATKBEMQZ-UHFFFAOYSA-N triethylene glycol Chemical class OCCOCCOCCO ZIBGPFATKBEMQZ-UHFFFAOYSA-N 0.000 description 1
- 238000009941 weaving Methods 0.000 description 1
- 210000002268 wool Anatomy 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
- D06M15/568—Reaction products of isocyanates with polyethers
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/587—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives characterised by the bonding agents used
-
- D—TEXTILES; PAPER
- D04—BRAIDING; LACE-MAKING; KNITTING; TRIMMINGS; NON-WOVEN FABRICS
- D04H—MAKING TEXTILE FABRICS, e.g. FROM FIBRES OR FILAMENTARY MATERIAL; FABRICS MADE BY SUCH PROCESSES OR APPARATUS, e.g. FELTS, NON-WOVEN FABRICS; COTTON-WOOL; WADDING ; NON-WOVEN FABRICS FROM STAPLE FIBRES, FILAMENTS OR YARNS, BONDED WITH AT LEAST ONE WEB-LIKE MATERIAL DURING THEIR CONSOLIDATION
- D04H1/00—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres
- D04H1/40—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties
- D04H1/58—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives
- D04H1/64—Non-woven fabrics formed wholly or mainly of staple fibres or like relatively short fibres from fleeces or layers composed of fibres without existing or potential cohesive properties by applying, incorporating or activating chemical or thermoplastic bonding agents, e.g. adhesives the bonding agent being applied in wet state, e.g. chemical agents in dispersions or solutions
-
- 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
-
- 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
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2965—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
- Y10T428/00—Stock material or miscellaneous articles
- Y10T428/29—Coated or structually defined flake, particle, cell, strand, strand portion, rod, filament, macroscopic fiber or mass thereof
- Y10T428/2913—Rod, strand, filament or fiber
- Y10T428/2933—Coated or with bond, impregnation or core
- Y10T428/2964—Artificial fiber or filament
- Y10T428/2967—Synthetic resin or polymer
- Y10T428/2969—Polyamide, polyimide or polyester
-
- 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.]
- Y10T442/60—Nonwoven fabric [i.e., nonwoven strand or fiber material]
Definitions
- ABSTRACT A process for binding nonwoven textiles by impregnating a nonwoven textile with a liquid application medium containing a polymer selected from the group consisting of 1.
- a polyurea polymer characterized by the 51 Aug. 7, 1973 generalized formula wherein m is 0 or 1, q is an integer from 1 to 13, p is an integer from 3 to 100, R is an alkylene group containing from 3 to 5 carbon atoms, each R" is independently hydrogen or methyl and each R is independently selected from the group consisting of H and CH OH, with the proviso that at least one R is CH OH and 2.
- polyureaurethane polymers characterized by the generalized formula (A), wherein x is an integer from 2 to 100 and each A is independently selected from the group consisting of and and at least one A is 1 It "-I I n'0 and with the further proviso that at least one R is a CH OH group.
- This invention relates to nonwoven fabrics and to processes for binding nonwoven textiles. More particularly, this invention relates to the use of improved binder resins for nonwoven fabrics.
- Nonwoven fabrics are structures comprising random or oriented fibers held together by adhesives.
- Nonwovcn fabrics have achieved considerable success in the textile industry since they can be produced more rapidly and more economically than woven fibers.
- the preparation of nonwoven textile fabrics differs from the preparation of conventional textile fabrics in that no weaving is required.
- the nonwoven material is prepared by forming the textile fibers into a coherent sheet or web and then binding the fibers together to give the finished fabric. In order to impart adequate strength to the fabric, the fabric is impregnated with a liquid solution or emulsion containing a binding or adhesive agent.
- the adhesives or binders which have been employed for the preparation of nonwoven fabrics include polyvinyl alcohol, polyvinyl acetate, polyvinyl chloride, acrylic polymers and butadiene-acrylonitrile copolymers and butadiene-styrene copolymers.
- lt is an object of this invention to provide a process for binding nonwoven textiles for the preparation of nonwoven fabrics having improved softness and drapeability without sacrificing properties such as tensile strength, color fastness, and resistance to washing and dry cleaning.
- the foregoing art objects and still furtherobjects are accomplished in-accordance with the present invention by providing improved adhesives or binders for the preparation of nonwoven fabrics having improved properties.
- the binders are methylolated polyurea polymers and methylolated polyureaurethane vpolymers.
- the methylolated polyurea polymers may be characterized by the generalized formula R t i 1 wherein m is or I, q is an integer from 1 to l3, p is an integer from 3 to 100, R is an alkylene group condependently selected from the group consisting of wherein m is 0 or 1, n is an integer from 2 to 14, q is an integer from I to 13, R' is an alkylene group having from 3 to 5 carbon atoms, each R" is independently hydrogen or methyl and each R is independently selected from the group consisting of hydrogen and CH OH, with the proviso that at least one A is and at least one A is O R H l with the proviso that at least one R is CH OH.
- the preferred compounds are those wherein substantially all of the R groups are CH OH.
- the resulting polymer is a polyurea polymer whereas if the reaction mixture contains some amino alcohol, the resulting polymer is a polyureaurethane polymer.
- the meth ylol groups may be introduced into the polymers by reacting the aforesaid reaction products with formaldehyde, paraformaldehyde, or other convenient sources of formaldehyde.
- the reaction conditions used are those conventionally used in the art for methylolating active'hydrogen containing compounds.
- the polyureapolymers may be prepared by reacting about equal molar amounts of urea and a diamineata temperaturefrom about to about 220 C.
- the diamine used may be any compound-characterized bythe generalized formula "H,N (RO),,,(CH,CHR'O), CHCHR"-'NH,
- n is an integer from 2'to 13
- R is
- the polyureaurethane polymers which are methylolated to prepare a binder in accordance with this invention may be prepared by reacting urea with substantially equal molar amounts of a mixture of an amino alcohol and a diamine at a temperature from 150 C. to about 220C.
- the diamine used may be any of those described above.
- the amino alcohol used may be any amino alcohol characterized by the generalized formula H N (RO),,,(CH CHR"O),,H wherein m is or 1, n is an integer from 2 to 14, R is an alkylene group having from 3 to 5 carbon atoms, and each R" is independently hydrogen or methyl.
- these amino alcohols include triethylene glycol monoamine, diethylene glycol monoamine, tripropylene glycol monoamine, diethylene glycol monoamine, dipropylene glycol monoamine, pentaoxyethylene monoamine, pentaoxypropylene monoamine, polyoxyethylene (14) monoamine, polyoxypropylene (5) monoamine, dipropylene glycol propyl amine, diethylene glycol propyl amine, and decaoxyethylene pe'ntyl amine.
- the mixture of diamine and amino alcohol may contain from to 100 percent by weight of diamine and from 90 to 0 percent by weight of the amino alcohol.
- the mixture of diamine and amino alcohol used may be the crude reaction product resulting from the ammonolysis of a glycol or by mixing together separately prepared diamine and amino alcohol.
- methylolated polyurea polymers and methylolated polyureaurethane polymers which may be used as binders for the preparation of non-woven fabrics in accordance with the present invention. Additional'polymers may be prepared by substituting other monoamines and diamines for those used in the illustrativeexample's.
- EXAMPLE A Into a 300 ml. flask equipped with stirrer, thermometer, and receiver system, are added 37.6 grams of urea and 200 grams of a crude aminated triethylene glycol containing substantially equal molar proportions of triethylene glycol diamine and triethylene glycol monoamine. The mixture is then heated between 9 7 159f C. for 3 hours, between 159181 C. for 1 hour, and then between 181 190 C. for 8 hours. The reaction product is terminally vacuum stripped at -20 mm mercury absolute. The resulting polyureaurethane polymer is a dark, viscous liquid having a molecular weight of about 1,500 and a Gardner Holt viscosity in meta-cresol of N(25 percent solution in 25 C.).
- EXAMPLE B 74.5 grams (1.24 mols) of urea, 142.9 grams (0.62 mols) of Jeffamine D-231 (bis-Z-aminopropyl ether of diethylene glycol) and 65.3 grains(0.62 mols) (diethylene glycol monoamine) are charged to a 3-necked, round-bottom flask provided with stirrer, thermometer, and reflux condenser vented through a dry ice trap. The mixture is then heated for 6 hours between 104-175 C., 16 hours at C., 4 hours at C. and then terminally vacuum stripped for 2 hours at 195 C. at 15-20 mm mercury absolute. The product is a yellow oil containing 11.2 percent nitrogen.
- EXAMPLE C A mixture of 357 grams of bis-Z-aminopropyl ether of diethylene glycol, 163.2 grams of diethylene glycol monoamine and 186.3 grams of urea is heated at 1 l7-200 C. for several hours to form a polyureaurethane polymer. The reaction mixture is then vacuum stripped at 195 C. and 0.3 mm mercury absolute. The resulting polyureaurethane is a clear amber solid. 1,247 grams of a 33 percent aqueous solutionof the polyureaurethane and 369 grams of a 37 percent aqueous formaldehyde solution are mixed together and the pH adjIistEdtHR STTBe solution is then heated at 50 C. for 15 hours to form the methylolated polyureaurethane polymer. The concentration of the resulting aqueous solution is adjusted to 34 percent solids content.
- EXAMPLE D 250 grams of a 33 percent solution of the polyureaurethane prepared in Example C is contacted with 54.7 grams of 37 percent aqueous formaldehyde solution. The pH of the solution is adjusted to 8.5, and the solution is heated at 50 C. for 15 hours. The concentration of the resulting solution is adjusted to have 36.6 percent by weight of the methylolated polyureaurethane polymer.
- EXAMPLE G 90 grams (L5 mols) of urea and 222 grams (1.5 mols) of triethylene glycol diamine are charged to a three-necked, round-bottom flask provided with a stirrer, thermometer, and reflux condenser vented through a dry ice trap. The reactants are heated, pnderanatrnosphere of nitrogen, for 18 hours at l20 165 C. The temperature is then slowly raised so as to allow an orderly collection of ammonia. 'T he reaction is terminated when the calculated amount of ammonia has been formed. The product is then vacuum s trippgd fg a short period of time to a final temperature of 185 C.
- the resulting polyurea polymer upon cooling is an opaque, light brown solid.
- a molecular weight determination using an osmometer gave a number average molecular weight of about 7,000.
- the polyurea polymer is soluble in water and contains l5.9 percent nitrogen and 0.09 percent amino nitrogen.
- a 25 percent solution of the polyurea at 22 C. in mcta-cresol has a Gardner Holt viscosity of W.
- Thepolyurea polymer is then methylolated by heating a mixture of 5 grams of the polyurea polymer, 6 grams of 36.7 percent aqueous formaldehyde, and 69 grams of water at 51 C. for hours.
- EXAMPLE H 12 grams of urea and 200 grams of polyoxypropylene diamine (polyether Ll000 from Union Carbide) are charged to the reaction flask described in Example G. The reactants are heated for hours at 130-l40 C. and then vacuum stripped for a short period of time. The resulting polyurea polymer upon cooling is a dark amber viscous liquid. The polymer contains 2.76 percent nitrogen and 0.02 percent amino nitrogen. The polyurea is then methylolated by reacting 25 grams of the product with 25 grams of formaldehyde (55 percent solution of formaldehyde and methanol), adjust ing the pH to 8.5 and refluxing the solution for 3 /2 hours.
- polyoxypropylene diamine polyether Ll000 from Union Carbide
- the nonwoven fabrics of the present invention comprise random or oriented fibers held together by one or more of the methylolated polyurea polymers or methylolated polyureaurethane polymers described above.
- the nonwoven fabrics of this invention may be prepared by a process which comprises impregnating a non-woven textile material with a liquid application medium having dipersed therein one or more of the above-described methylolated polyurea polymers or methylolated polyureaurethane polymers.
- the polymers used in the process of the present invention may be applied from any available form of liquid application medium such as from an aqueous emulpolymer is adsion or a solution in a suitable organic solvent.
- the binder polymer may be applied in any manner suitable for impregnating textiles with liquid textile treating medium, such as by dipping, padding, spraying, printing or immersing the textile in or with the treating medium.
- an emulsifying agent should be included.
- Emulsifying agents are well known in this art and any suitable agent can be employed. Examples of such suitable emulsifying agents include condensation products of octyl and nonyl phenol with from 8 to l7 mols of ethylene oxide.
- the concentration of the binder polymer in the application medium is not a critical feature of the present invention.
- the application medium applied to the textile contains from about 1 to about 25 percent of polymer.
- the amount of binder polymer solids (dry basis) applied to the nonwoven textile may vary over a wide range and will depend among other things on the particular textile material and on the type and use intended for the final fabric. It is, essential, of course, that the amount be sufficient to bind the textile fibers. Although other amounts of binder polymer may be used if desired, the amount of polymeric binder present on the nonwoven fabric is typically from about 2 percent to about percent by weight, and preferably from about 5 percent to about 50 percent by weight, based on the total weight of the nonwoven fabric.
- the treated textile is dried and then cured at elevated temperatures.
- the temperature used to effect curing of the treated fabric will vary and will depend onsuch factors as the specific textile material being treated and the particular equipment employed. Of course, curing temperatures which cause discoloration or burning of the textile materials should be avoided. Typically, a temperature in the range of from about 200 F. to about 350 F. is employed.
- the time used for curing may also vary, generally in inverse proportions to the temperature used. For example, when a temperature of 200 F. is employed, longer curing times are required then when a temperature of 300 F. is employed.
- the process of the present invention is applicable to nonwoven textile materials of all types made from natural and synthetic fibers and blends thereof.
- illustrative examples of such materials include cotton fibers, blends of cotton and rayon, rayon, blends of cotton or rayon with synthetic fibers, wool, silk, polyesters, nylon, viscose rayon, acetate rayon, polyolefins, and other natural and synthetic fibers.
- any fiber or textile material may be used for the preparation of nonwoven fabrics of this invention, cellulosic fibers are preferred because of their low cost.
- the textile materials used to prepare the nonwoven fabrics of the present invention may be fibers or fibrous structures, including webs containing a random arrangement of fibers, webs containing oriented fibers, laminated structures consisting of two or more webs having any desired degree of fiber orientation, webs reinforced with yarn, filaments, or scrims, and the like.
- the application medium may contain such additives as thermosetting agents, curing catalysts, softening agents, shrink-proofing agents, flame-proofing agents, and so forth. Materials in these groups-are well known to those skilled in the art and would be applied to obtain the special effect indicated by the function of the agent. Alternatively, such material may be applied to the textile material either before or after application of the binder composition of the present invention.
- the binder resins may be applied to the textile material in accordance with this invention along with an acid catalyst. It is believed that the acid catalyst promotes reaction of the binder polymer with the active hydrogens present in the textile material.
- the acid catalyst and the binder polymer may be applied to the textile material simultaneously or in separate steps as is conventional in the art.
- Illustrative examples of curing catalysts include zinc nitrate, ammonium chloride, am-
- the amount of acid actalyst used is the amount conventionally used in the art for curing methylolated polymers onto textile materials. In general, satisfactory reuslts are obtained by using from about 1 percent to about 35 percent of catalyst based on the weight of methylolated polymer used.
- EXAMPLE 1 A solution was prepared containing 20 percent of the product of Example B (a 35 percent active water solution of methylolated polyureaurethane polymer), 2 percent zinc nitrate, and 78 percent water. Strands of drawn sliver, prepared from 2 inch, 3 dpf, rayon staple, placed between two layers of cheese cloth for support, are immersed in the solution and then passed between the squeezed rolls of a laboratory padder. A wet pick up of 100 percent is obtained, resulting in the deposi-' tion of approximately 7 percent resin solids based on the weight of the fiber. The treated sliver is dried for minutes at 225 F. and cured for 5 minutes at 325 F.
- Tests showed the tensile strength of the treated sliver to be 9.6 kilograms per strand and to have good softness.
- the tensile strength decreased to 6.9 kilograms after a minute wash in 0.1 percent TIDE solution at 140 F. There was no change in the strength after a 15 minute wash in perchloroethylene at room temperature.
- the ensile strength before washing is approximately 3 times that obtained with an equal amount (solid basis) of a commercially available selfcrosslinking acrylic binder (Rhoplex HA-8), and the softness is approximately equal. After washing the tensile strength is still about 1.8 times greater than that of the washed sample containing Rhoplex HA-8 acrylic binder.
- Table 1 The results are shown in Table 1.
- EXAMPLE 2 A solution containing percent of the aqueous solution of Example B, 2 percent zinc nitrate, 4 percent Mykon SF (a percent active polyethylene emulsion), and 74 percent water. This solution was used to treat strands of drawn sliver as described in Example 1. Properties of the treated sliver are shown in Table 1.
- EXAMPLE 3 The methylolated polyureaurethane of Example A is applied to rayon sliver as in Example 1 except that the treated sliver is dried for 8 miriiftes at 225 F. and cured for 5 minutes at 325 F. The properties of the treated sliver are shown in Table I)
- EXAMPLE 4 A rayon sliver, prepared from 1.5 denier, rayon staple is padded with a solution containing 20 percent of the aqueous solution of Example A, 2 percent zinc nitrate, and 78 percent water as provided in Example 1.
- the treated sliver is dried for 8 minutes at 225 F.
- Example 4 is repeated except that the binder resin used is the methylolated polyureaurethane polymer of Example E. Tests results on the treated sliver are shown in Table 1.
- Example 4 is repeated using the methylolated polyureaurethane polymer binder of Example F.
- Example 4 is repeated except that the binder resin used is the methylolated polyureaurethane polymer of Example C.
- the test results are shown in Table 1.
- Example 4 is repeated except that the binder resin used is the methylolated polyureaurethane polymer prepared in Example D. The test results are shown in Table 1.
- a solution is prepared containing 28.6 percent of the product of Example A (a 34.3 percent active water solution of methylolated polyureaurethane polymer), 2.86 percent zinc nitrate hexahydrate, and 68.54 percent water. The solution is used to pad sliver prepared from 1% inch and 1.5 denier nylon fiber and to pad sliver prepared from 1% inch and 1.5 denier polyester fiber.
- cstcr Average of ten single-end breaks Washed by shaking in 0.1% aqueous solution of TIDE detergent for 15 minutes at 140F.
- EXAMPLE A solution is prepared containing 20 percent of the methylotated polyurea of Example G, 2 percent zinc nitrate, and 78 percent water. The solution is used to pad a nonwoven fleece prepared of cotton fibers at 100 percent wet pickup. The padded products are dried for 10 minutes at 200 F. and cured for 5 minutes at 300 F. The cured product exhibited excellent tensile strength and softness and negligible discoloration.
- EXAMPLE 11 A nonwoven polyester fleece is sprayed with a solution containing percent of the methylolated polyurea of Example H, 3 percent zinc nitrate, and 82 percent water. The treated polyester is dried for 8 minutes at 225 F. and then cured for 5 minutes at 330 F. The resulting nonwoven fabric has high tensile strength, a high degree of softness, and negligible discoloration.
- EXAMPLE 12 An aqueous textile bath was prepared by mixing 10 parts of the methylolated polyurea of Example .1 with 2 parts of zinc nitrate and 88 parts of water. Nonwoven webs of rayon fleece are impregnated with this textile bath at 100 percent wet pickup, dried in air at 250 F. for 10 minutes, and then heated an additional 5 minutes at 300 F. The nonwoven fabrics exhibit excellent softness and drapeability, high tensile strength, and good color fastness.
- Example 12 is repeated except that the polymer used is the methylolated polyureaurethane polymer of Example A.
- the treated nonwoven fabric has excellent tensile strength, color fastness, softness, and drapeability.
- the nonwoven fabrics of the present invention are particularly useful as interfacings, linings, and shaping materials in the garment, shoe and luggage trade and in disposable items of wearing apparel such as hospital garments, underwear, dresses, shirts and so forth which may be worn once or several times before being discarded, and in sheets and needlepunched blankets.
- a nonwoven fabric comprising fibers held together by from 2 percent to 80 percent of a binder resin, based on the total weight of fabric, wherein the binder resin comprises a methylolated polyurea characterized by the generalized formula wherein m is 0 or 1, q is an integer from 1 to 13 p.
- R is an integer from 3 to 100
- R is an alkylene group containing from 3 to 5 carbon atoms
- each R" is independently hydrogen or methyl
- each R is independently selected from the group consisting of hydrogen and CH Ol-l with the proviso that at least one R is CH OH or a methylolated polyureaurethane characterized by the generalized formula (A) wherein x is an integer from 2 to 100 and each A is independently selected from the group consisting of and and at least one is with the proviso that at least on R is CH,O11.
- a nonwoven fabric of claim 1 wherein the fiber comprises cellulosic fibers.
- a nonwoven fabric of claim 1 comprising cellulose fibers held together by a methylolated polyureaurethane.
- a nonwoven fabric of claim 1 wherein the fiber comprises nylon fibers.
- a nonwoven fabric of claim 1 wherein the fiber comprises polyester fibers.
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Dispersion Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Adhesives Or Adhesive Processes (AREA)
- Nonwoven Fabrics (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
- Phenolic Resins Or Amino Resins (AREA)
- Polyurethanes Or Polyureas (AREA)
Applications Claiming Priority (1)
Application Number | Priority Date | Filing Date | Title |
---|---|---|---|
US15468571A | 1971-06-18 | 1971-06-18 |
Publications (1)
Publication Number | Publication Date |
---|---|
US3751290A true US3751290A (en) | 1973-08-07 |
Family
ID=22552325
Family Applications (1)
Application Number | Title | Priority Date | Filing Date |
---|---|---|---|
US00154685A Expired - Lifetime US3751290A (en) | 1971-06-18 | 1971-06-18 | Nonwoven fabrics |
Country Status (3)
Country | Link |
---|---|
US (1) | US3751290A (enrdf_load_stackoverflow) |
JP (2) | JPS5140188B1 (enrdf_load_stackoverflow) |
GB (1) | GB1343553A (enrdf_load_stackoverflow) |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3900688A (en) * | 1972-10-25 | 1975-08-19 | Bayer Ag | Textile substrate having coatings of polycarbonate-polyurea elastomer |
EP0852271A3 (en) * | 1997-01-07 | 1999-06-23 | Plastilab S.p.A. | Method for manufacturing textile products and textile product thus manufactured |
Families Citing this family (3)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
JPS6058130U (ja) * | 1983-09-27 | 1985-04-23 | 日東電工株式会社 | ギブス包帯 |
JPS61110531U (enrdf_load_stackoverflow) * | 1984-12-26 | 1986-07-12 | ||
CN108660749B (zh) * | 2018-06-05 | 2021-06-11 | 曲周县新兆源纺织有限公司 | 良好吸湿、透气的聚氨酯合成革用水刺无纺布的制备方法 |
Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2696504A (en) * | 1952-07-12 | 1954-12-07 | Rohm & Haas | Polyaminopolyureas |
US2699435A (en) * | 1952-07-22 | 1955-01-11 | Rohm & Haas | Polyurea resins |
US2709694A (en) * | 1952-10-07 | 1955-05-31 | Du Pont | Reaction of polyureas and formaldehyde and hydrolysis, and the products |
US2774687A (en) * | 1952-09-03 | 1956-12-18 | Nottebohm Carl Ludwig | Process for the manufacture of porous flexible sheet material |
US2955095A (en) * | 1958-01-08 | 1960-10-04 | Du Pont | Composition comprising chain extended polyurethane dissolved in dialkyl sulfoxide and a ketone and process of coating therewith |
US3000757A (en) * | 1957-01-28 | 1961-09-19 | Du Pont | Process for coating substrates with a vapor permeable polymeric coating |
US3021307A (en) * | 1958-06-30 | 1962-02-13 | Du Pont | Polyurethane elastomers cured with paraformaldehyde |
US3054777A (en) * | 1958-05-16 | 1962-09-18 | Toyo Koatsu Ind Inc | Linear polyureas |
US3133897A (en) * | 1959-03-30 | 1964-05-19 | Toyo Koatsu Ind Inc | Production of polyurea copolymers from an alkylene diamine, a heteromembered alkylene diamine and a urea |
US3359243A (en) * | 1964-12-15 | 1967-12-19 | Monsanto Co | Linear polyurea elastomers |
US3412072A (en) * | 1964-12-30 | 1968-11-19 | Exxon Research Engineering Co | Polyureas |
-
1971
- 1971-06-18 US US00154685A patent/US3751290A/en not_active Expired - Lifetime
-
1972
- 1972-06-02 JP JP47055023A patent/JPS5140188B1/ja active Pending
- 1972-06-16 GB GB2830372A patent/GB1343553A/en not_active Expired
-
1976
- 1976-04-12 JP JP51041181A patent/JPS51127275A/ja active Granted
Patent Citations (11)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US2696504A (en) * | 1952-07-12 | 1954-12-07 | Rohm & Haas | Polyaminopolyureas |
US2699435A (en) * | 1952-07-22 | 1955-01-11 | Rohm & Haas | Polyurea resins |
US2774687A (en) * | 1952-09-03 | 1956-12-18 | Nottebohm Carl Ludwig | Process for the manufacture of porous flexible sheet material |
US2709694A (en) * | 1952-10-07 | 1955-05-31 | Du Pont | Reaction of polyureas and formaldehyde and hydrolysis, and the products |
US3000757A (en) * | 1957-01-28 | 1961-09-19 | Du Pont | Process for coating substrates with a vapor permeable polymeric coating |
US2955095A (en) * | 1958-01-08 | 1960-10-04 | Du Pont | Composition comprising chain extended polyurethane dissolved in dialkyl sulfoxide and a ketone and process of coating therewith |
US3054777A (en) * | 1958-05-16 | 1962-09-18 | Toyo Koatsu Ind Inc | Linear polyureas |
US3021307A (en) * | 1958-06-30 | 1962-02-13 | Du Pont | Polyurethane elastomers cured with paraformaldehyde |
US3133897A (en) * | 1959-03-30 | 1964-05-19 | Toyo Koatsu Ind Inc | Production of polyurea copolymers from an alkylene diamine, a heteromembered alkylene diamine and a urea |
US3359243A (en) * | 1964-12-15 | 1967-12-19 | Monsanto Co | Linear polyurea elastomers |
US3412072A (en) * | 1964-12-30 | 1968-11-19 | Exxon Research Engineering Co | Polyureas |
Cited By (2)
Publication number | Priority date | Publication date | Assignee | Title |
---|---|---|---|---|
US3900688A (en) * | 1972-10-25 | 1975-08-19 | Bayer Ag | Textile substrate having coatings of polycarbonate-polyurea elastomer |
EP0852271A3 (en) * | 1997-01-07 | 1999-06-23 | Plastilab S.p.A. | Method for manufacturing textile products and textile product thus manufactured |
Also Published As
Publication number | Publication date |
---|---|
JPS5140188B1 (enrdf_load_stackoverflow) | 1976-11-01 |
JPS51127275A (en) | 1976-11-05 |
GB1343553A (en) | 1974-01-10 |
JPS5314663B2 (enrdf_load_stackoverflow) | 1978-05-19 |
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