CA1053867A - Microporous sheets and a process for making them - Google Patents
Microporous sheets and a process for making themInfo
- Publication number
- CA1053867A CA1053867A CA207,232A CA207232A CA1053867A CA 1053867 A CA1053867 A CA 1053867A CA 207232 A CA207232 A CA 207232A CA 1053867 A CA1053867 A CA 1053867A
- Authority
- CA
- Canada
- Prior art keywords
- polyurethane
- weight
- acid
- water
- solution
- 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
Links
- 238000000034 method Methods 0.000 title claims abstract description 79
- 230000008569 process Effects 0.000 title claims abstract description 57
- 239000004814 polyurethane Substances 0.000 claims abstract description 130
- 229920002635 polyurethane Polymers 0.000 claims abstract description 121
- 239000002904 solvent Substances 0.000 claims abstract description 48
- 125000002091 cationic group Chemical group 0.000 claims abstract description 37
- 125000000129 anionic group Chemical group 0.000 claims abstract description 29
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Chemical compound O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 claims description 74
- 239000000725 suspension Substances 0.000 claims description 32
- 238000005345 coagulation Methods 0.000 claims description 27
- 230000015271 coagulation Effects 0.000 claims description 27
- 229920003226 polyurethane urea Polymers 0.000 claims description 25
- 239000002798 polar solvent Substances 0.000 claims description 9
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical compound [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 claims description 7
- 230000001112 coagulating effect Effects 0.000 claims description 6
- 238000002156 mixing Methods 0.000 claims description 6
- XSQUKJJJFZCRTK-UHFFFAOYSA-N Urea Chemical compound NC(N)=O XSQUKJJJFZCRTK-UHFFFAOYSA-N 0.000 claims description 5
- 239000004202 carbamide Substances 0.000 claims description 4
- 239000000203 mixture Substances 0.000 abstract description 37
- 239000006185 dispersion Substances 0.000 abstract description 25
- ZMXDDKWLCZADIW-UHFFFAOYSA-N N,N-Dimethylformamide Chemical compound CN(C)C=O ZMXDDKWLCZADIW-UHFFFAOYSA-N 0.000 description 121
- 239000000243 solution Substances 0.000 description 71
- 150000001875 compounds Chemical class 0.000 description 28
- 229920000728 polyester Polymers 0.000 description 27
- 239000003795 chemical substances by application Substances 0.000 description 26
- LYCAIKOWRPUZTN-UHFFFAOYSA-N Ethylene glycol Chemical compound OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 25
- 238000006243 chemical reaction Methods 0.000 description 25
- 229920001971 elastomer Polymers 0.000 description 25
- 239000000806 elastomer Substances 0.000 description 25
- 239000000047 product Substances 0.000 description 24
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 19
- -1 diol compounds Chemical class 0.000 description 19
- 238000002360 preparation method Methods 0.000 description 16
- 229920000642 polymer Polymers 0.000 description 15
- 239000002245 particle Substances 0.000 description 14
- 239000007787 solid Substances 0.000 description 14
- 238000007792 addition Methods 0.000 description 13
- 229920001296 polysiloxane Polymers 0.000 description 13
- 238000003756 stirring Methods 0.000 description 13
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 12
- WERYXYBDKMZEQL-UHFFFAOYSA-N butane-1,4-diol Chemical compound OCCCCO WERYXYBDKMZEQL-UHFFFAOYSA-N 0.000 description 12
- 238000000576 coating method Methods 0.000 description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 12
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 description 11
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical class OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 11
- 150000002009 diols Chemical class 0.000 description 11
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 description 11
- 239000012948 isocyanate Substances 0.000 description 11
- 229920000570 polyether Polymers 0.000 description 11
- 239000002253 acid Substances 0.000 description 10
- 150000004985 diamines Chemical class 0.000 description 10
- 125000005442 diisocyanate group Chemical group 0.000 description 10
- 238000004519 manufacturing process Methods 0.000 description 10
- 150000002513 isocyanates Chemical class 0.000 description 9
- 239000011541 reaction mixture Substances 0.000 description 9
- 230000001588 bifunctional effect Effects 0.000 description 8
- 239000007795 chemical reaction product Substances 0.000 description 8
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 8
- 125000004433 nitrogen atom Chemical group N* 0.000 description 8
- 239000000758 substrate Substances 0.000 description 8
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 description 7
- WYURNTSHIVDZCO-UHFFFAOYSA-N Tetrahydrofuran Chemical compound C1CCOC1 WYURNTSHIVDZCO-UHFFFAOYSA-N 0.000 description 7
- 239000007864 aqueous solution Substances 0.000 description 7
- 239000012298 atmosphere Substances 0.000 description 7
- 230000008901 benefit Effects 0.000 description 7
- 230000015572 biosynthetic process Effects 0.000 description 7
- 238000004132 cross linking Methods 0.000 description 7
- 230000035699 permeability Effects 0.000 description 7
- 150000003839 salts Chemical class 0.000 description 7
- 239000005057 Hexamethylene diisocyanate Substances 0.000 description 6
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 6
- 235000011037 adipic acid Nutrition 0.000 description 6
- 239000011888 foil Substances 0.000 description 6
- 150000002334 glycols Chemical class 0.000 description 6
- 239000003960 organic solvent Substances 0.000 description 6
- UPMLOUAZCHDJJD-UHFFFAOYSA-N 4,4'-Diphenylmethane Diisocyanate Chemical compound C1=CC(N=C=O)=CC=C1CC1=CC=C(N=C=O)C=C1 UPMLOUAZCHDJJD-UHFFFAOYSA-N 0.000 description 5
- RPNUMPOLZDHAAY-UHFFFAOYSA-N Diethylenetriamine Chemical compound NCCNCCN RPNUMPOLZDHAAY-UHFFFAOYSA-N 0.000 description 5
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 description 5
- 125000001931 aliphatic group Chemical group 0.000 description 5
- 150000001412 amines Chemical class 0.000 description 5
- 238000009835 boiling Methods 0.000 description 5
- 239000011248 coating agent Substances 0.000 description 5
- 150000002148 esters Chemical class 0.000 description 5
- 239000000499 gel Substances 0.000 description 5
- 230000007062 hydrolysis Effects 0.000 description 5
- 238000006460 hydrolysis reaction Methods 0.000 description 5
- 229920003009 polyurethane dispersion Polymers 0.000 description 5
- 229910052708 sodium Inorganic materials 0.000 description 5
- 239000011734 sodium Substances 0.000 description 5
- 238000011282 treatment Methods 0.000 description 5
- QGZKDVFQNNGYKY-UHFFFAOYSA-N Ammonia Chemical compound N QGZKDVFQNNGYKY-UHFFFAOYSA-N 0.000 description 4
- UHOVQNZJYSORNB-UHFFFAOYSA-N Benzene Chemical compound C1=CC=CC=C1 UHOVQNZJYSORNB-UHFFFAOYSA-N 0.000 description 4
- OAKJQQAXSVQMHS-UHFFFAOYSA-N Hydrazine Chemical compound NN OAKJQQAXSVQMHS-UHFFFAOYSA-N 0.000 description 4
- DGAQECJNVWCQMB-PUAWFVPOSA-M Ilexoside XXIX Chemical compound C[C@@H]1CC[C@@]2(CC[C@@]3(C(=CC[C@H]4[C@]3(CC[C@@H]5[C@@]4(CC[C@@H](C5(C)C)OS(=O)(=O)[O-])C)C)[C@@H]2[C@]1(C)O)C)C(=O)O[C@H]6[C@@H]([C@H]([C@@H]([C@H](O6)CO)O)O)O.[Na+] DGAQECJNVWCQMB-PUAWFVPOSA-M 0.000 description 4
- 239000002168 alkylating agent Substances 0.000 description 4
- 229940100198 alkylating agent Drugs 0.000 description 4
- 125000003118 aryl group Chemical group 0.000 description 4
- 235000013877 carbamide Nutrition 0.000 description 4
- XEVRDFDBXJMZFG-UHFFFAOYSA-N carbonyl dihydrazine Chemical compound NNC(=O)NN XEVRDFDBXJMZFG-UHFFFAOYSA-N 0.000 description 4
- VAYGXNSJCAHWJZ-UHFFFAOYSA-N dimethyl sulfate Chemical compound COS(=O)(=O)OC VAYGXNSJCAHWJZ-UHFFFAOYSA-N 0.000 description 4
- 238000009472 formulation Methods 0.000 description 4
- 125000005843 halogen group Chemical group 0.000 description 4
- 238000010438 heat treatment Methods 0.000 description 4
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 description 4
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 4
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 description 4
- 239000007788 liquid Substances 0.000 description 4
- 239000002609 medium Substances 0.000 description 4
- 239000000178 monomer Substances 0.000 description 4
- 239000012071 phase Substances 0.000 description 4
- 229920001568 phenolic resin Polymers 0.000 description 4
- 235000011007 phosphoric acid Nutrition 0.000 description 4
- XNGIFLGASWRNHJ-UHFFFAOYSA-N phthalic acid Chemical compound OC(=O)C1=CC=CC=C1C(O)=O XNGIFLGASWRNHJ-UHFFFAOYSA-N 0.000 description 4
- 239000005056 polyisocyanate Substances 0.000 description 4
- 125000005373 siloxane group Chemical group [SiH2](O*)* 0.000 description 4
- 239000007858 starting material Substances 0.000 description 4
- 229920001567 vinyl ester resin Polymers 0.000 description 4
- QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 description 3
- JOYRKODLDBILNP-UHFFFAOYSA-N Ethyl urethane Chemical compound CCOC(N)=O JOYRKODLDBILNP-UHFFFAOYSA-N 0.000 description 3
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 description 3
- MUBZPKHOEPUJKR-UHFFFAOYSA-N Oxalic acid Chemical compound OC(=O)C(O)=O MUBZPKHOEPUJKR-UHFFFAOYSA-N 0.000 description 3
- 239000004721 Polyphenylene oxide Substances 0.000 description 3
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 description 3
- 229910000831 Steel Inorganic materials 0.000 description 3
- 239000000654 additive Substances 0.000 description 3
- 125000000217 alkyl group Chemical group 0.000 description 3
- 229910000147 aluminium phosphate Inorganic materials 0.000 description 3
- 125000003277 amino group Chemical group 0.000 description 3
- 125000004432 carbon atom Chemical group C* 0.000 description 3
- 150000001768 cations Chemical class 0.000 description 3
- KRKNYBCHXYNGOX-UHFFFAOYSA-N citric acid Chemical compound OC(=O)CC(O)(C(O)=O)CC(O)=O KRKNYBCHXYNGOX-UHFFFAOYSA-N 0.000 description 3
- 239000000701 coagulant Substances 0.000 description 3
- 238000004821 distillation Methods 0.000 description 3
- 229960004279 formaldehyde Drugs 0.000 description 3
- 235000019256 formaldehyde Nutrition 0.000 description 3
- SLGWESQGEUXWJQ-UHFFFAOYSA-N formaldehyde;phenol Chemical compound O=C.OC1=CC=CC=C1 SLGWESQGEUXWJQ-UHFFFAOYSA-N 0.000 description 3
- 239000011521 glass Substances 0.000 description 3
- 229920000578 graft copolymer Polymers 0.000 description 3
- 125000004435 hydrogen atom Chemical group [H]* 0.000 description 3
- 238000002844 melting Methods 0.000 description 3
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- 229920001228 polyisocyanate Polymers 0.000 description 3
- 229920003225 polyurethane elastomer Polymers 0.000 description 3
- 239000000843 powder Substances 0.000 description 3
- 125000002924 primary amino group Chemical group [H]N([H])* 0.000 description 3
- 239000010959 steel Substances 0.000 description 3
- 238000012360 testing method Methods 0.000 description 3
- YLQBMQCUIZJEEH-UHFFFAOYSA-N tetrahydrofuran Natural products C=1C=COC=1 YLQBMQCUIZJEEH-UHFFFAOYSA-N 0.000 description 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical compound CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 description 3
- 150000003672 ureas Chemical class 0.000 description 3
- RYHBNJHYFVUHQT-UHFFFAOYSA-N 1,4-Dioxane Chemical compound C1COCCO1 RYHBNJHYFVUHQT-UHFFFAOYSA-N 0.000 description 2
- ZZHIDJWUJRKHGX-UHFFFAOYSA-N 1,4-bis(chloromethyl)benzene Chemical compound ClCC1=CC=C(CCl)C=C1 ZZHIDJWUJRKHGX-UHFFFAOYSA-N 0.000 description 2
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- ALRHLSYJTWAHJZ-UHFFFAOYSA-N 3-hydroxypropionic acid Chemical compound OCCC(O)=O ALRHLSYJTWAHJZ-UHFFFAOYSA-N 0.000 description 2
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 description 2
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 description 2
- IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
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- WTEOIRVLGSZEPR-UHFFFAOYSA-N boron trifluoride Chemical compound FB(F)F WTEOIRVLGSZEPR-UHFFFAOYSA-N 0.000 description 2
- 125000003178 carboxy group Chemical group [H]OC(*)=O 0.000 description 2
- FDJUMMKAFUMWBI-UHFFFAOYSA-N chloro carbonochloridate Chemical class ClOC(Cl)=O FDJUMMKAFUMWBI-UHFFFAOYSA-N 0.000 description 2
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- WOZVHXUHUFLZGK-UHFFFAOYSA-N dimethyl terephthalate Chemical compound COC(=O)C1=CC=C(C(=O)OC)C=C1 WOZVHXUHUFLZGK-UHFFFAOYSA-N 0.000 description 2
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- OHLKMGYGBHFODF-UHFFFAOYSA-N 1,4-bis(isocyanatomethyl)benzene Chemical compound O=C=NCC1=CC=C(CN=C=O)C=C1 OHLKMGYGBHFODF-UHFFFAOYSA-N 0.000 description 1
- ALQLPWJFHRMHIU-UHFFFAOYSA-N 1,4-diisocyanatobenzene Chemical compound O=C=NC1=CC=C(N=C=O)C=C1 ALQLPWJFHRMHIU-UHFFFAOYSA-N 0.000 description 1
- CDMDQYCEEKCBGR-UHFFFAOYSA-N 1,4-diisocyanatocyclohexane Chemical compound O=C=NC1CCC(N=C=O)CC1 CDMDQYCEEKCBGR-UHFFFAOYSA-N 0.000 description 1
- IURPGYHEBMCDGZ-UHFFFAOYSA-N 1,5-dichloro-2,3,4-trimethylbenzene Chemical compound CC1=C(C)C(Cl)=CC(Cl)=C1C IURPGYHEBMCDGZ-UHFFFAOYSA-N 0.000 description 1
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Classifications
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J9/00—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof
- C08J9/28—Working-up of macromolecular substances to porous or cellular articles or materials; After-treatment thereof by elimination of a liquid phase from a macromolecular composition or article, e.g. drying of coagulum
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L75/00—Compositions of polyureas or polyurethanes; Compositions of derivatives of such polymers
-
- 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
-
- 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
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/6436—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain containing amino 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
- D06M15/37—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds
- D06M15/643—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain
- D06M15/653—Macromolecular compounds obtained otherwise than by reactions only involving carbon-to-carbon unsaturated bonds containing silicon in the main chain modified by isocyanate compounds
-
- 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
- D06N3/14—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 polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08J—WORKING-UP; GENERAL PROCESSES OF COMPOUNDING; AFTER-TREATMENT NOT COVERED BY SUBCLASSES C08B, C08C, C08F, C08G or C08H
- C08J2375/00—Characterised by the use of polyureas or polyurethanes; Derivatives of such polymers
Landscapes
- Chemical & Material Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Engineering & Computer Science (AREA)
- Textile Engineering (AREA)
- Health & Medical Sciences (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Materials Engineering (AREA)
- Dispersion Chemistry (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
- Polyurethanes Or Polyureas (AREA)
- Compositions Of Macromolecular Compounds (AREA)
- Synthetic Leather, Interior Materials Or Flexible Sheet Materials (AREA)
- Manufacture Of Macromolecular Shaped Articles (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DE19732345256 DE2345256A1 (de) | 1973-09-07 | 1973-09-07 | Verfahren zur herstellung von mikroporoesen flaechengebilden |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| CA1053867A true CA1053867A (en) | 1979-05-08 |
Family
ID=5891993
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| CA207,232A Expired CA1053867A (en) | 1973-09-07 | 1974-08-16 | Microporous sheets and a process for making them |
Country Status (16)
| Country | Link |
|---|---|
| US (1) | US4086193A (enExample) |
| JP (2) | JPS5321703B2 (enExample) |
| BE (1) | BE819588A (enExample) |
| CA (1) | CA1053867A (enExample) |
| CS (1) | CS177187B2 (enExample) |
| DD (1) | DD114963A5 (enExample) |
| DE (1) | DE2345256A1 (enExample) |
| DK (1) | DK472274A (enExample) |
| ES (1) | ES429816A1 (enExample) |
| FR (1) | FR2243223B1 (enExample) |
| GB (1) | GB1485441A (enExample) |
| IT (1) | IT1019193B (enExample) |
| LU (1) | LU70859A1 (enExample) |
| NL (1) | NL7411749A (enExample) |
| PL (1) | PL98030B1 (enExample) |
| RO (1) | RO69545A (enExample) |
Families Citing this family (21)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2721985A1 (de) * | 1977-05-14 | 1978-11-16 | Bayer Ag | Verfahren zur herstellung von urethan- und/oder harnstoffgruppen aufweisenden polyisocyanat polyadditionsprodukten |
| JPS54130699A (en) * | 1978-03-31 | 1979-10-11 | Sanyo Chem Ind Ltd | Preparation of polyurethane resin and sheet material |
| DE3414978A1 (de) * | 1984-04-19 | 1985-10-31 | Industrie-Entwicklungen Krüpper, 8059 Wartenberg | Griffbaender auf der basis von mit kunststoff beschichteten traegermaterialien |
| DE3438563A1 (de) * | 1984-10-20 | 1986-04-24 | Bayer Ag, 5090 Leverkusen | Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier |
| JPS61146802A (ja) * | 1984-12-21 | 1986-07-04 | ダイヤゴム株式会社 | 透湿性且つ耐油性作業用手袋およびその製造方法 |
| DE3523856A1 (de) * | 1985-07-04 | 1987-01-08 | Bayer Ag | Waessrige loesungen oder dispersionen von polyisocyanat-additionsprodukten, ein verfahren zu ihrer herstellung, sowie ihre verwendung als beschichtungsmittel oder als leimungsmittel fuer papier |
| DE3603996A1 (de) * | 1986-02-08 | 1987-08-13 | Bayer Ag | Verfahren zur kontinuierlichen herstellung von waessrigen polyurethandispersionen und ihre verwendung als beschichtungsmittel oder als klebstoff |
| JPH0639750B2 (ja) * | 1986-03-04 | 1994-05-25 | 大日精化工業株式会社 | 擬 革 |
| US4746684A (en) * | 1986-05-21 | 1988-05-24 | Dainichiseika Color & Chemicals Mfg. Co., Ltd. | Polyurethane dispersion and emulsion, sheet-like porous material and production process thereof |
| DE3633874A1 (de) * | 1986-10-04 | 1988-04-14 | Stockhausen Chem Fab Gmbh | Verfahren zur herstellung mit polyurethan beschichteter textiler flaechengebilde, mit polyurethan beschichtete textile flaechengebilde und ihre verwendung zur herstellung atmungsaktiver und wasserabweisender ausruestungen |
| JPH0637754B2 (ja) * | 1987-08-10 | 1994-05-18 | 大日精化工業株式会社 | 多孔性シ−ト材料及びその製造方法 |
| DE3727252A1 (de) * | 1987-08-15 | 1989-02-23 | Bayer Ag | Verfahren zur herstellung von waessrigen polyurethandispersionen |
| DE3827378A1 (de) | 1988-08-12 | 1990-02-22 | Henkel Kgaa | Haushaltsalleskleber auf polyurethanbasis |
| JP3305358B2 (ja) | 1992-06-17 | 2002-07-22 | 大日本インキ化学工業株式会社 | 多孔質性シート材料の製造方法及びシート |
| DE4445200A1 (de) * | 1994-12-17 | 1996-06-20 | Herberts Gmbh | Wäßrige Überzugsmittel und deren Verwendung bei Verfahren zur Einschicht- und Mehrschichtlackierung |
| US5698613A (en) * | 1995-02-21 | 1997-12-16 | Mancuso Chemicals Limited | Chemical binder |
| DE19943933A1 (de) * | 1999-07-30 | 2001-02-01 | Bayer Ag | Lichtechte Beschichtungsmittel |
| DE102004013259A1 (de) * | 2004-03-18 | 2005-09-29 | Bayer Materialscience Ag | Wässrige PUR-Dispersionen mit verbesserter Haftung |
| DE102006016638A1 (de) * | 2006-04-08 | 2007-10-11 | Bayer Materialscience Ag | Mikroporöse Beschichtung auf Basis von Polyurethan-Polyharnstoff |
| DE102006020745A1 (de) * | 2006-05-04 | 2007-11-08 | Bayer Materialscience Ag | Mikroporöse Beschichtung auf Basis von Polyurethan-Polyharnstoff |
| CA2736127A1 (en) * | 2008-09-05 | 2010-03-11 | Arrowstar, Llc | Compositions and methods for imparting water and oil repellency to fibers and articles thereof |
Family Cites Families (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1190176B (de) * | 1961-04-25 | 1965-04-01 | Bayer Ag | Verwendung von Carbodiimiden gemeinsam mit siliciumorganischen Verbindungen als stabilisierende Mittel in estergruppenhaltigen Polyurethanen |
| US3763054A (en) * | 1970-12-07 | 1973-10-02 | Bayer Ag | Process for the production of microporous polyurethane (urea) sheet structures permeable to water vapor |
-
1973
- 1973-09-07 DE DE19732345256 patent/DE2345256A1/de active Pending
-
1974
- 1974-08-16 CA CA207,232A patent/CA1053867A/en not_active Expired
- 1974-08-29 US US05/501,575 patent/US4086193A/en not_active Expired - Lifetime
- 1974-08-31 RO RO7479887A patent/RO69545A/ro unknown
- 1974-09-03 CS CS6065A patent/CS177187B2/cs unknown
- 1974-09-04 NL NL7411749A patent/NL7411749A/xx unknown
- 1974-09-04 GB GB38649/74A patent/GB1485441A/en not_active Expired
- 1974-09-05 BE BE148244A patent/BE819588A/xx unknown
- 1974-09-05 IT IT52883/74A patent/IT1019193B/it active
- 1974-09-05 DD DD180937A patent/DD114963A5/xx unknown
- 1974-09-05 LU LU70859A patent/LU70859A1/xx unknown
- 1974-09-06 JP JP10215974A patent/JPS5321703B2/ja not_active Expired
- 1974-09-06 FR FR7430304A patent/FR2243223B1/fr not_active Expired
- 1974-09-06 PL PL1974173910A patent/PL98030B1/pl unknown
- 1974-09-06 DK DK472274A patent/DK472274A/da unknown
- 1974-09-06 ES ES429816A patent/ES429816A1/es not_active Expired
-
1979
- 1979-06-06 JP JP7001679A patent/JPS5527381A/ja active Granted
Also Published As
| Publication number | Publication date |
|---|---|
| JPS5051569A (enExample) | 1975-05-08 |
| ES429816A1 (es) | 1976-09-01 |
| PL98030B1 (pl) | 1978-04-29 |
| DD114963A5 (enExample) | 1975-09-05 |
| RO69545A (ro) | 1981-06-30 |
| DK472274A (enExample) | 1975-05-05 |
| FR2243223A1 (enExample) | 1975-04-04 |
| IT1019193B (it) | 1977-11-10 |
| BE819588A (fr) | 1975-03-05 |
| NL7411749A (nl) | 1975-03-11 |
| JPS5321703B2 (enExample) | 1978-07-04 |
| US4086193A (en) | 1978-04-25 |
| JPS5527381A (en) | 1980-02-27 |
| DE2345256A1 (de) | 1975-03-20 |
| GB1485441A (en) | 1977-09-14 |
| JPS5539573B2 (enExample) | 1980-10-13 |
| FR2243223B1 (enExample) | 1978-02-17 |
| LU70859A1 (enExample) | 1975-05-28 |
| CS177187B2 (enExample) | 1977-07-29 |
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