DE1621910A1 - Verfahren zum Beschichten mit Polyurethanen - Google Patents
Verfahren zum Beschichten mit PolyurethanenInfo
- Publication number
- DE1621910A1 DE1621910A1 DE19671621910 DE1621910A DE1621910A1 DE 1621910 A1 DE1621910 A1 DE 1621910A1 DE 19671621910 DE19671621910 DE 19671621910 DE 1621910 A DE1621910 A DE 1621910A DE 1621910 A1 DE1621910 A1 DE 1621910A1
- Authority
- DE
- Germany
- Prior art keywords
- reaction product
- blocked
- coating
- ketoximes
- parts
- 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.)
- Pending
Links
- 238000000576 coating method Methods 0.000 title claims description 25
- 239000011248 coating agent Substances 0.000 title claims description 21
- 238000000034 method Methods 0.000 title claims description 12
- 239000004814 polyurethane Substances 0.000 title description 2
- 229920002635 polyurethane Polymers 0.000 title description 2
- 239000007795 chemical reaction product Substances 0.000 claims description 12
- 150000001875 compounds Chemical class 0.000 claims description 12
- 125000002887 hydroxy group Chemical group [H]O* 0.000 claims description 11
- 229920000728 polyester Polymers 0.000 claims description 9
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 claims description 8
- 239000005056 polyisocyanate Substances 0.000 claims description 8
- 229920001228 polyisocyanate Polymers 0.000 claims description 8
- 239000012876 carrier material Substances 0.000 claims description 7
- 239000000203 mixture Substances 0.000 claims description 6
- FZWBABZIGXEXES-UHFFFAOYSA-N ethane-1,2-diol;hexanedioic acid Chemical compound OCCO.OC(=O)CCCCC(O)=O FZWBABZIGXEXES-UHFFFAOYSA-N 0.000 claims description 5
- 125000001302 tertiary amino group Chemical group 0.000 claims description 4
- 230000035939 shock Effects 0.000 claims description 3
- 229940008841 1,6-hexamethylene diisocyanate Drugs 0.000 claims description 2
- JXCHMDATRWUOAP-UHFFFAOYSA-N diisocyanatomethylbenzene Chemical compound O=C=NC(N=C=O)C1=CC=CC=C1 JXCHMDATRWUOAP-UHFFFAOYSA-N 0.000 claims description 2
- RRAMGCGOFNQTLD-UHFFFAOYSA-N hexamethylene diisocyanate Chemical compound O=C=NCCCCCCN=C=O RRAMGCGOFNQTLD-UHFFFAOYSA-N 0.000 claims description 2
- 238000006243 chemical reaction Methods 0.000 claims 1
- 239000000047 product Substances 0.000 claims 1
- XEKOWRVHYACXOJ-UHFFFAOYSA-N Ethyl acetate Chemical compound CCOC(C)=O XEKOWRVHYACXOJ-UHFFFAOYSA-N 0.000 description 15
- 239000004744 fabric Substances 0.000 description 6
- 239000000463 material Substances 0.000 description 6
- 150000001412 amines Chemical class 0.000 description 4
- 238000001035 drying Methods 0.000 description 4
- ZWEHNKRNPOVVGH-UHFFFAOYSA-N 2-Butanone Chemical compound CCC(C)=O ZWEHNKRNPOVVGH-UHFFFAOYSA-N 0.000 description 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 description 3
- YXFVVABEGXRONW-UHFFFAOYSA-N Toluene Chemical compound CC1=CC=CC=C1 YXFVVABEGXRONW-UHFFFAOYSA-N 0.000 description 3
- 238000004132 cross linking Methods 0.000 description 3
- 238000010438 heat treatment Methods 0.000 description 3
- 239000000123 paper Substances 0.000 description 3
- 239000002904 solvent Substances 0.000 description 3
- 239000004753 textile Substances 0.000 description 3
- XLLIQLLCWZCATF-UHFFFAOYSA-N 2-methoxyethyl acetate Chemical compound COCCOC(C)=O XLLIQLLCWZCATF-UHFFFAOYSA-N 0.000 description 2
- ISWSIDIOOBJBQZ-UHFFFAOYSA-N Phenol Chemical compound OC1=CC=CC=C1 ISWSIDIOOBJBQZ-UHFFFAOYSA-N 0.000 description 2
- 229920001577 copolymer Polymers 0.000 description 2
- 125000005442 diisocyanate group Chemical group 0.000 description 2
- 229920001971 elastomer Polymers 0.000 description 2
- 239000012442 inert solvent Substances 0.000 description 2
- 238000003475 lamination Methods 0.000 description 2
- 239000002649 leather substitute Substances 0.000 description 2
- 238000004519 manufacturing process Methods 0.000 description 2
- 238000002156 mixing Methods 0.000 description 2
- WHIVNJATOVLWBW-UHFFFAOYSA-N n-butan-2-ylidenehydroxylamine Chemical compound CCC(C)=NO WHIVNJATOVLWBW-UHFFFAOYSA-N 0.000 description 2
- 230000006855 networking Effects 0.000 description 2
- 239000005060 rubber Substances 0.000 description 2
- 229920002050 silicone resin Polymers 0.000 description 2
- 238000003860 storage Methods 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- 238000004383 yellowing Methods 0.000 description 2
- JMFLYAQVWMIMKC-UHFFFAOYSA-N 3-(2-aminoethylamino)propane-1,1,1,3-tetrol Chemical compound NCCNC(O)CC(O)(O)O JMFLYAQVWMIMKC-UHFFFAOYSA-N 0.000 description 1
- ORAJHYSVXOYBCP-UHFFFAOYSA-N 3-[2-[bis(3-hydroxypropyl)amino]ethyl-(3-hydroxypropyl)amino]propan-1-ol Chemical compound OCCCN(CCCO)CCN(CCCO)CCCO ORAJHYSVXOYBCP-UHFFFAOYSA-N 0.000 description 1
- 239000004971 Cross linker Substances 0.000 description 1
- VGGSQFUCUMXWEO-UHFFFAOYSA-N Ethene Chemical compound C=C VGGSQFUCUMXWEO-UHFFFAOYSA-N 0.000 description 1
- 239000005977 Ethylene Substances 0.000 description 1
- 239000004677 Nylon Substances 0.000 description 1
- 229920002292 Nylon 6 Polymers 0.000 description 1
- CYTYCFOTNPOANT-UHFFFAOYSA-N Perchloroethylene Chemical group ClC(Cl)=C(Cl)Cl CYTYCFOTNPOANT-UHFFFAOYSA-N 0.000 description 1
- 229920005830 Polyurethane Foam Polymers 0.000 description 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 description 1
- SLINHMUFWFWBMU-UHFFFAOYSA-N Triisopropanolamine Chemical compound CC(O)CN(CC(C)O)CC(C)O SLINHMUFWFWBMU-UHFFFAOYSA-N 0.000 description 1
- ZJCCRDAZUWHFQH-UHFFFAOYSA-N Trimethylolpropane Chemical compound CCC(CO)(CO)CO ZJCCRDAZUWHFQH-UHFFFAOYSA-N 0.000 description 1
- XTXRWKRVRITETP-UHFFFAOYSA-N Vinyl acetate Chemical compound CC(=O)OC=C XTXRWKRVRITETP-UHFFFAOYSA-N 0.000 description 1
- PXAJQJMDEXJWFB-UHFFFAOYSA-N acetone oxime Chemical compound CC(C)=NO PXAJQJMDEXJWFB-UHFFFAOYSA-N 0.000 description 1
- 230000002411 adverse Effects 0.000 description 1
- 150000001336 alkenes Chemical class 0.000 description 1
- 150000001414 amino alcohols Chemical class 0.000 description 1
- 150000004982 aromatic amines Chemical class 0.000 description 1
- 230000009286 beneficial effect Effects 0.000 description 1
- 239000002981 blocking agent Substances 0.000 description 1
- 230000001680 brushing effect Effects 0.000 description 1
- 238000003490 calendering Methods 0.000 description 1
- 239000011111 cardboard Substances 0.000 description 1
- 239000003054 catalyst Substances 0.000 description 1
- 238000001816 cooling Methods 0.000 description 1
- 238000007334 copolymerization reaction Methods 0.000 description 1
- 239000000839 emulsion Substances 0.000 description 1
- 230000002349 favourable effect Effects 0.000 description 1
- 239000011888 foil Substances 0.000 description 1
- 230000007062 hydrolysis Effects 0.000 description 1
- 238000006460 hydrolysis reaction Methods 0.000 description 1
- 238000005470 impregnation Methods 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- 238000004898 kneading Methods 0.000 description 1
- 150000002736 metal compounds Chemical class 0.000 description 1
- CRVGTESFCCXCTH-UHFFFAOYSA-N methyl diethanolamine Chemical compound OCCN(C)CCO CRVGTESFCCXCTH-UHFFFAOYSA-N 0.000 description 1
- DNYZBFWKVMKMRM-UHFFFAOYSA-N n-benzhydrylidenehydroxylamine Chemical compound C=1C=CC=CC=1C(=NO)C1=CC=CC=C1 DNYZBFWKVMKMRM-UHFFFAOYSA-N 0.000 description 1
- 229920001778 nylon Polymers 0.000 description 1
- 238000010915 one-step procedure Methods 0.000 description 1
- 239000003960 organic solvent Substances 0.000 description 1
- 150000002923 oximes Chemical class 0.000 description 1
- 230000001766 physiological effect Effects 0.000 description 1
- 229920000515 polycarbonate Polymers 0.000 description 1
- 239000004417 polycarbonate Substances 0.000 description 1
- 229920006324 polyoxymethylene Polymers 0.000 description 1
- 239000011496 polyurethane foam Substances 0.000 description 1
- QQONPFPTGQHPMA-UHFFFAOYSA-N propylene Natural products CC=C QQONPFPTGQHPMA-UHFFFAOYSA-N 0.000 description 1
- 125000004805 propylene group Chemical group [H]C([H])([H])C([H])([*:1])C([H])([H])[*:2] 0.000 description 1
- 238000007127 saponification reaction Methods 0.000 description 1
- 150000005619 secondary aliphatic amines Chemical class 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 239000000126 substance Substances 0.000 description 1
- 150000003509 tertiary alcohols Chemical class 0.000 description 1
- 150000003510 tertiary aliphatic amines Chemical class 0.000 description 1
- 150000003512 tertiary amines Chemical class 0.000 description 1
- 229950011008 tetrachloroethylene Drugs 0.000 description 1
- 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 1
- PJANXHGTPQOBST-VAWYXSNFSA-N trans-stilbene Chemical group C=1C=CC=CC=1/C=C/C1=CC=CC=C1 PJANXHGTPQOBST-VAWYXSNFSA-N 0.000 description 1
Classifications
-
- 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
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/08—Processes
- C08G18/10—Prepolymer processes involving reaction of isocyanates or isothiocyanates with compounds having active hydrogen in a first reaction step
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G18/00—Polymeric products of isocyanates or isothiocyanates
- C08G18/06—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen
- C08G18/70—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the isocyanates or isothiocyanates used
- C08G18/72—Polyisocyanates or polyisothiocyanates
- C08G18/77—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur
- C08G18/78—Nitrogen
- C08G18/79—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates
- C08G18/791—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing isocyanurate 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
- D06M15/564—Polyureas, polyurethanes or other polymers having ureide or urethane links; Precondensation products forming them
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)
- Dispersion Chemistry (AREA)
- Paints Or Removers (AREA)
- Polyurethanes Or Polyureas (AREA)
- Treatments For Attaching Organic Compounds To Fibrous Goods (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| DEF0053427 | 1967-09-06 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1621910A1 true DE1621910A1 (de) | 1971-06-24 |
Family
ID=7106298
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19671621910 Pending DE1621910A1 (de) | 1967-09-06 | 1967-09-06 | Verfahren zum Beschichten mit Polyurethanen |
Country Status (5)
| Country | Link |
|---|---|
| US (1) | US3583943A (https=) |
| BE (1) | BE720516A (https=) |
| DE (1) | DE1621910A1 (https=) |
| FR (1) | FR1599761A (https=) |
| GB (1) | GB1186649A (https=) |
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2251889A1 (de) * | 1971-10-25 | 1973-05-03 | Shell Int Research | Verfahren zur herstellung von verschaeumten polyurethanen |
| DE3004327A1 (de) * | 1980-02-06 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Umkehrverfahren zur herstellung von veloursleder-imitaten |
Families Citing this family (26)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3694389A (en) * | 1970-08-06 | 1972-09-26 | Rohm & Haas | Thermosetting coatings based on oxime-blocked isocyanates |
| US4203889A (en) * | 1973-06-20 | 1980-05-20 | American Cyanamid Company | Polyurethane compositions stabilized with ketoximes |
| DE2732775A1 (de) * | 1977-07-20 | 1979-02-08 | Veba Chemie Ag | Verfahren zur herstellung duroplastischer einkomponentiger polyurethane |
| DE2806731A1 (de) * | 1978-02-17 | 1979-08-23 | Bayer Ag | Verfahren zur herstellung von isocyanuratgruppen aufweisenden polyisocyanaten |
| CA1112243A (en) * | 1978-09-08 | 1981-11-10 | Manfred Bock | Process for the preparation of polyisocyanates containing isocyanurate groups and the use thereof |
| US4530859A (en) * | 1981-12-23 | 1985-07-23 | Minnesota Mining And Manufacturing Company | Method of preparing a polymeric coating composition from a blocked isocyanate-functional polymeric compound and a crosslinking agent which is insoluble in aprotic solvents |
| FR2544322B1 (fr) * | 1983-04-13 | 1986-07-25 | Stevens Genin | Tissus de verre et analogues preimpregnes par un polyurethanne-uree, melanges reactifs stables correspondants, procede de fabrication et application |
| US4722969A (en) * | 1986-09-18 | 1988-02-02 | W. R. Grace & Co. | Storage stable, low temperature, solventless, curable urethane composition |
| US4767836A (en) * | 1987-05-18 | 1988-08-30 | Texaco Inc. | Storage stable polyurethane coating |
| US5049249A (en) * | 1988-11-23 | 1991-09-17 | E. I. Du Pont De Nemours And Company | Low cure cathodic electrodeposition coatings |
| US4900415A (en) * | 1988-11-23 | 1990-02-13 | E. I. Du Pont De Nemours & Company | Low cure cathodic electrodeposition coatings |
| US4976833A (en) * | 1989-10-04 | 1990-12-11 | E. I. Du Pont De Nemours And Company | Electrodeposition coatings containing blocked tetramethylxylene diisocyanate crosslinker |
| US5185065A (en) * | 1991-08-01 | 1993-02-09 | E. I. Du Pont De Nemours And Company | Low temperature coring cathodic electrocoating composition |
| JP2925736B2 (ja) * | 1991-08-07 | 1999-07-28 | ピーピージー インダストリーズ インコーポレーテッド | 独立して架橋しうるポリウレタンを有する含浸された繊維の束 |
| ES2104162T3 (es) * | 1992-08-06 | 1997-10-01 | Alcantara Spa | Tejido de ante microfibroso sin tejer y procedimiento para su preparacion. |
| FR2787446B1 (fr) | 1998-12-22 | 2001-02-02 | Rhone Poulenc Fibres | Procede d'hydrocyanation de composes organiques a insaturations ethyleniques |
| CA2353005A1 (en) * | 2000-08-01 | 2002-02-01 | Dai-Ichi Kogyo Seiyaku Co., Ltd. | Blocked urethane prepolymers as paper wet strength agent |
| JP2003138497A (ja) * | 2001-10-31 | 2003-05-14 | Dai Ichi Kogyo Seiyaku Co Ltd | 湿潤紙力増強剤 |
| FR2849027B1 (fr) * | 2002-12-23 | 2005-01-21 | Rhodia Polyamide Intermediates | Procede de synthese de composes comprenant des fonctions nitriles a partir de composes a insaturations ethyleniques |
| US7226983B2 (en) * | 2004-04-08 | 2007-06-05 | Acushnet Company | Golf ball compositions with improved temperature performance, heat resistance, and resiliency |
| US7163994B2 (en) * | 2004-04-08 | 2007-01-16 | Acushnet Company | Golf ball composition with improved temperature performance, heat resistance and resiliency |
| US20080051526A1 (en) * | 2004-10-14 | 2008-02-28 | Akzo Nobel Coatings International B.V. | Coating composition |
| JP2008101088A (ja) * | 2006-10-18 | 2008-05-01 | Sumika Bayer Urethane Kk | 脂肪族ポリイソシアネート組成物およびそれを用いたポリウレタン樹脂塗料組成物 |
| FR2943061B1 (fr) | 2009-03-13 | 2011-02-25 | Rhodia Operations | Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation ou d'hydroformylation utilisant ces systemes catalytiques |
| FR2950349B1 (fr) | 2009-09-18 | 2011-08-26 | Rhodia Operations | Composes organophosphores, systemes catalytiques comprenant ces composes et procede d'hydrocyanation utilisant ces systemes catalytiques |
| FR2980792B1 (fr) | 2011-09-30 | 2013-09-06 | Rhodia Operations | Procede de fabrication de composes nitriles a partir de composes a insaturation ethylenique |
-
1967
- 1967-09-06 DE DE19671621910 patent/DE1621910A1/de active Pending
-
1968
- 1968-09-04 US US757453A patent/US3583943A/en not_active Expired - Lifetime
- 1968-09-06 BE BE720516A patent/BE720516A/xx unknown
- 1968-09-06 GB GB42495/68A patent/GB1186649A/en not_active Expired
- 1968-09-06 FR FR1599761D patent/FR1599761A/fr not_active Expired
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE2251889A1 (de) * | 1971-10-25 | 1973-05-03 | Shell Int Research | Verfahren zur herstellung von verschaeumten polyurethanen |
| DE3004327A1 (de) * | 1980-02-06 | 1981-08-13 | Bayer Ag, 5090 Leverkusen | Umkehrverfahren zur herstellung von veloursleder-imitaten |
| EP0034272A3 (en) * | 1980-02-06 | 1981-09-09 | Bayer Ag | Process for producing velvet leather imitations by the reversal process |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1186649A (en) | 1970-04-02 |
| US3583943A (en) | 1971-06-08 |
| FR1599761A (https=) | 1970-07-20 |
| BE720516A (https=) | 1969-02-17 |
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