DE1910224A1 - Verfahren zur Herstellung von Polyurethanschaumstoffen - Google Patents
Verfahren zur Herstellung von PolyurethanschaumstoffenInfo
- Publication number
- DE1910224A1 DE1910224A1 DE19691910224 DE1910224A DE1910224A1 DE 1910224 A1 DE1910224 A1 DE 1910224A1 DE 19691910224 DE19691910224 DE 19691910224 DE 1910224 A DE1910224 A DE 1910224A DE 1910224 A1 DE1910224 A1 DE 1910224A1
- Authority
- DE
- Germany
- Prior art keywords
- polyol
- component
- reaction
- parts
- acid
- 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
- 238000000034 method Methods 0.000 title claims description 16
- 238000004519 manufacturing process Methods 0.000 title claims description 12
- 229920005830 Polyurethane Foam Polymers 0.000 title description 5
- 239000011496 polyurethane foam Substances 0.000 title description 5
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 claims description 31
- 239000002253 acid Substances 0.000 claims description 23
- 229920005862 polyol Polymers 0.000 claims description 16
- 150000003077 polyols Chemical class 0.000 claims description 15
- 238000006243 chemical reaction Methods 0.000 claims description 14
- 235000011187 glycerol Nutrition 0.000 claims description 14
- 239000000203 mixture Substances 0.000 claims description 12
- 150000007513 acids Chemical class 0.000 claims description 9
- 235000014113 dietary fatty acids Nutrition 0.000 claims description 8
- 229930195729 fatty acid Natural products 0.000 claims description 8
- 239000000194 fatty acid Substances 0.000 claims description 8
- 150000004665 fatty acids Chemical class 0.000 claims description 8
- 150000005846 sugar alcohols Polymers 0.000 claims description 8
- 150000004670 unsaturated fatty acids Chemical class 0.000 claims description 7
- 235000021122 unsaturated fatty acids Nutrition 0.000 claims description 7
- 239000007795 chemical reaction product Substances 0.000 claims description 6
- 239000011347 resin Substances 0.000 claims description 6
- 229920005989 resin Polymers 0.000 claims description 6
- 150000002148 esters Chemical class 0.000 claims description 5
- 229920001228 polyisocyanate Polymers 0.000 claims description 4
- 239000005056 polyisocyanate Substances 0.000 claims description 4
- 239000004814 polyurethane Substances 0.000 claims description 4
- 229920002635 polyurethane Polymers 0.000 claims description 4
- 239000013543 active substance Substances 0.000 claims description 3
- 150000008064 anhydrides Chemical class 0.000 claims description 3
- 239000003063 flame retardant Substances 0.000 claims description 3
- 239000004604 Blowing Agent Substances 0.000 claims description 2
- OFOBLEOULBTSOW-UHFFFAOYSA-N Malonic acid Chemical compound OC(=O)CC(O)=O OFOBLEOULBTSOW-UHFFFAOYSA-N 0.000 claims description 2
- 239000003054 catalyst Substances 0.000 claims description 2
- 239000000463 material Substances 0.000 claims description 2
- 150000007519 polyprotic acids Polymers 0.000 claims description 2
- 241000953561 Toia Species 0.000 claims 1
- 230000015572 biosynthetic process Effects 0.000 claims 1
- 239000002131 composite material Substances 0.000 claims 1
- 239000000047 product Substances 0.000 description 11
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 description 10
- 125000002887 hydroxy group Chemical group [H]O* 0.000 description 8
- FPYJFEHAWHCUMM-UHFFFAOYSA-N maleic anhydride Chemical compound O=C1OC(=O)C=C1 FPYJFEHAWHCUMM-UHFFFAOYSA-N 0.000 description 8
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 description 6
- 239000001361 adipic acid Substances 0.000 description 5
- 235000011037 adipic acid Nutrition 0.000 description 5
- LFQSCWFLJHTTHZ-UHFFFAOYSA-N Ethanol Chemical compound CCO LFQSCWFLJHTTHZ-UHFFFAOYSA-N 0.000 description 4
- 230000032050 esterification Effects 0.000 description 4
- 238000005886 esterification reaction Methods 0.000 description 4
- LYCAIKOWRPUZTN-UHFFFAOYSA-N ethylene glycol Natural products OCCO LYCAIKOWRPUZTN-UHFFFAOYSA-N 0.000 description 4
- RTBFRGCFXZNCOE-UHFFFAOYSA-N 1-methylsulfonylpiperidin-4-one Chemical compound CS(=O)(=O)N1CCC(=O)CC1 RTBFRGCFXZNCOE-UHFFFAOYSA-N 0.000 description 3
- OKKJLVBELUTLKV-UHFFFAOYSA-N Methanol Chemical compound OC OKKJLVBELUTLKV-UHFFFAOYSA-N 0.000 description 3
- LGRFSURHDFAFJT-UHFFFAOYSA-N Phthalic anhydride Natural products C1=CC=C2C(=O)OC(=O)C2=C1 LGRFSURHDFAFJT-UHFFFAOYSA-N 0.000 description 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 description 3
- 238000007792 addition Methods 0.000 description 3
- JFCQEDHGNNZCLN-UHFFFAOYSA-N anhydrous glutaric acid Natural products OC(=O)CCCC(O)=O JFCQEDHGNNZCLN-UHFFFAOYSA-N 0.000 description 3
- JHIWVOJDXOSYLW-UHFFFAOYSA-N butyl 2,2-difluorocyclopropane-1-carboxylate Chemical compound CCCCOC(=O)C1CC1(F)F JHIWVOJDXOSYLW-UHFFFAOYSA-N 0.000 description 3
- 150000001875 compounds Chemical class 0.000 description 3
- 238000001816 cooling Methods 0.000 description 3
- 239000006260 foam Substances 0.000 description 3
- WGCNASOHLSPBMP-UHFFFAOYSA-N hydroxyacetaldehyde Natural products OCC=O WGCNASOHLSPBMP-UHFFFAOYSA-N 0.000 description 3
- 239000001384 succinic acid Substances 0.000 description 3
- 239000003784 tall oil Substances 0.000 description 3
- HZAXFHJVJLSVMW-UHFFFAOYSA-N 2-Aminoethan-1-ol Chemical compound NCCO HZAXFHJVJLSVMW-UHFFFAOYSA-N 0.000 description 2
- 229920013701 VORANOL™ Polymers 0.000 description 2
- ZBCBWPMODOFKDW-UHFFFAOYSA-N diethanolamine Chemical compound OCCNCCO ZBCBWPMODOFKDW-UHFFFAOYSA-N 0.000 description 2
- 238000004821 distillation Methods 0.000 description 2
- -1 glycol ester Chemical class 0.000 description 2
- 229920000728 polyester Polymers 0.000 description 2
- 229920001296 polysiloxane Polymers 0.000 description 2
- CXMXRPHRNRROMY-UHFFFAOYSA-N sebacic acid Chemical compound OC(=O)CCCCCCCCC(O)=O CXMXRPHRNRROMY-UHFFFAOYSA-N 0.000 description 2
- 239000000243 solution Substances 0.000 description 2
- 239000000126 substance Substances 0.000 description 2
- 239000003760 tallow Substances 0.000 description 2
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 2
- ZXHZWRZAWJVPIC-UHFFFAOYSA-N 1,2-diisocyanatonaphthalene Chemical compound C1=CC=CC2=C(N=C=O)C(N=C=O)=CC=C21 ZXHZWRZAWJVPIC-UHFFFAOYSA-N 0.000 description 1
- LDVVTQMJQSCDMK-UHFFFAOYSA-N 1,3-dihydroxypropan-2-yl formate Chemical compound OCC(CO)OC=O LDVVTQMJQSCDMK-UHFFFAOYSA-N 0.000 description 1
- JAHNSTQSQJOJLO-UHFFFAOYSA-N 2-(3-fluorophenyl)-1h-imidazole Chemical compound FC1=CC=CC(C=2NC=CN=2)=C1 JAHNSTQSQJOJLO-UHFFFAOYSA-N 0.000 description 1
- VEXZGXHMUGYJMC-UHFFFAOYSA-M Chloride anion Chemical compound [Cl-] VEXZGXHMUGYJMC-UHFFFAOYSA-M 0.000 description 1
- VOPWNXZWBYDODV-UHFFFAOYSA-N Chlorodifluoromethane Chemical compound FC(F)Cl VOPWNXZWBYDODV-UHFFFAOYSA-N 0.000 description 1
- 240000004093 Mitragyna parvifolia Species 0.000 description 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 description 1
- 229910019142 PO4 Inorganic materials 0.000 description 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 description 1
- 239000004721 Polyphenylene oxide Substances 0.000 description 1
- 241001417495 Serranidae Species 0.000 description 1
- 235000019486 Sunflower oil Nutrition 0.000 description 1
- GSEJCLTVZPLZKY-UHFFFAOYSA-N Triethanolamine Chemical compound OCCN(CCO)CCO GSEJCLTVZPLZKY-UHFFFAOYSA-N 0.000 description 1
- 239000007983 Tris buffer Substances 0.000 description 1
- 150000001298 alcohols Chemical class 0.000 description 1
- 150000001412 amines Chemical class 0.000 description 1
- 239000006227 byproduct Substances 0.000 description 1
- 241001233037 catfish Species 0.000 description 1
- 239000003795 chemical substances by application Substances 0.000 description 1
- 239000013256 coordination polymer Substances 0.000 description 1
- 239000006071 cream Substances 0.000 description 1
- 239000012043 crude product Substances 0.000 description 1
- XLJMAIOERFSOGZ-UHFFFAOYSA-M cyanate Chemical compound [O-]C#N XLJMAIOERFSOGZ-UHFFFAOYSA-M 0.000 description 1
- 150000001991 dicarboxylic acids Chemical class 0.000 description 1
- 125000005442 diisocyanate group Chemical group 0.000 description 1
- 125000000118 dimethyl group Chemical group [H]C([H])([H])* 0.000 description 1
- 239000012972 dimethylethanolamine Substances 0.000 description 1
- 239000000975 dye Substances 0.000 description 1
- 239000003925 fat Substances 0.000 description 1
- 239000010685 fatty oil Substances 0.000 description 1
- 239000012467 final product Substances 0.000 description 1
- 244000144980 herd Species 0.000 description 1
- 235000015243 ice cream Nutrition 0.000 description 1
- 239000012948 isocyanate Substances 0.000 description 1
- 150000002513 isocyanates Chemical class 0.000 description 1
- HTUMBQDCCIXGCV-UHFFFAOYSA-N lead oxide Chemical compound [O-2].[Pb+2] HTUMBQDCCIXGCV-UHFFFAOYSA-N 0.000 description 1
- YEXPOXQUZXUXJW-UHFFFAOYSA-N lead(II) oxide Inorganic materials [Pb]=O YEXPOXQUZXUXJW-UHFFFAOYSA-N 0.000 description 1
- 150000004702 methyl esters Chemical class 0.000 description 1
- LVHBHZANLOWSRM-UHFFFAOYSA-N methylenebutanedioic acid Natural products OC(=O)CC(=C)C(O)=O LVHBHZANLOWSRM-UHFFFAOYSA-N 0.000 description 1
- 239000003921 oil Substances 0.000 description 1
- 235000019198 oils Nutrition 0.000 description 1
- NBIIXXVUZAFLBC-UHFFFAOYSA-K phosphate Chemical compound [O-]P([O-])([O-])=O NBIIXXVUZAFLBC-UHFFFAOYSA-K 0.000 description 1
- 239000010452 phosphate Substances 0.000 description 1
- 229910052698 phosphorus Inorganic materials 0.000 description 1
- 239000011574 phosphorus Substances 0.000 description 1
- 229920000570 polyether Polymers 0.000 description 1
- 229920000642 polymer Polymers 0.000 description 1
- 239000011541 reaction mixture Substances 0.000 description 1
- 230000035484 reaction time Effects 0.000 description 1
- 239000002453 shampoo Substances 0.000 description 1
- 239000007787 solid Substances 0.000 description 1
- 238000003756 stirring Methods 0.000 description 1
- 239000002600 sunflower oil Substances 0.000 description 1
- 239000004094 surface-active agent Substances 0.000 description 1
- 150000003606 tin compounds Chemical class 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
- UFTFJSFQGQCHQW-UHFFFAOYSA-N triformin Chemical compound O=COCC(OC=O)COC=O UFTFJSFQGQCHQW-UHFFFAOYSA-N 0.000 description 1
- 239000000080 wetting agent Substances 0.000 description 1
Classifications
-
- 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
- C08G18/28—Polymeric products of isocyanates or isothiocyanates with compounds having active hydrogen characterised by the compounds used containing active hydrogen
- C08G18/67—Unsaturated compounds having active hydrogen
- C08G18/68—Unsaturated polyesters
- C08G18/683—Unsaturated polyesters containing cyclic groups
- C08G18/686—Unsaturated polyesters containing cyclic groups containing cycloaliphatic groups
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
- Manufacture Of Porous Articles, And Recovery And Treatment Of Waste Products (AREA)
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB01324/68A GB1222426A (en) | 1968-03-08 | 1968-03-08 | Improvements in or relating to the production of polyurethane foam materials |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| DE1910224A1 true DE1910224A1 (de) | 1969-10-02 |
Family
ID=9984175
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| DE19691910224 Pending DE1910224A1 (de) | 1968-03-08 | 1969-02-28 | Verfahren zur Herstellung von Polyurethanschaumstoffen |
Country Status (6)
| Country | Link |
|---|---|
| US (1) | US3644237A (https=) |
| DE (1) | DE1910224A1 (https=) |
| DK (1) | DK125801B (https=) |
| ES (1) | ES364454A1 (https=) |
| FR (1) | FR2003473A1 (https=) |
| GB (1) | GB1222426A (https=) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0473399A3 (en) * | 1990-08-31 | 1993-01-13 | Cape Industries | Polyester polyols from tall oil fatty acid maleic anhydride, and aromatic polyester polyols |
Families Citing this family (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3988268A (en) * | 1972-02-17 | 1976-10-26 | Bayer Aktiengesellschaft | Polyurethane foam plastics which contain ionic groups |
| FR2988723B1 (fr) * | 2012-03-30 | 2014-04-25 | Arkema France | Dispersions aqueuses de resines polyurethanes a base de colophane |
| FR2989975B1 (fr) * | 2012-04-25 | 2016-05-27 | Arkema France | Polyurethane pour revetements non aqueux a base de polyester gras hydroxyle biosource, modifie a la colophane |
| FR3117857B1 (fr) * | 2020-12-21 | 2023-12-01 | Oreal | Polymères alkyde biosourcé – polyuréthane en cosmétique |
Family Cites Families (8)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US2602783A (en) * | 1949-01-14 | 1952-07-08 | Lockheed Aircraft Corp | Cellular foamed alkyd-diisocyanate resins |
| US2591884A (en) * | 1949-02-17 | 1952-04-08 | Lockheed Aircraft Corp | Alkyd resin-diisocyanate cellular foamed plastics |
| US2698838A (en) * | 1950-09-23 | 1955-01-04 | Lockheed Aircraft Corp | Heat resistant oxalate-alkyd-isocyanate cellular plastics |
| US2811493A (en) * | 1953-05-11 | 1957-10-29 | Lockheed Aircraft Corp | Elastomeric cellular products obtained from alkyd resin-diisocyanate mixture |
| US3068254A (en) * | 1958-02-20 | 1962-12-11 | Pittsburgh Plate Glass Co | Low viscosity polymerized fatty acids polyester resins and method of making same |
| DE1143019B (de) * | 1961-04-29 | 1963-01-31 | Bayer Ag | Verfahren zur Herstellung von Urethangruppen aufweisenden Schaumstoffen |
| DE1178585B (de) * | 1962-05-30 | 1964-09-24 | Bayer Ag | Verfahren zur Herstellung von Urethangruppen aufweisenden Schaumstoffen |
| GB1032365A (en) * | 1963-04-02 | 1966-06-08 | Bibby & Sons Ltd J | Improvements in or relating to glycol esters of tribasic organic compounds and to polyurethanes obtainable therefrom |
-
1968
- 1968-03-08 GB GB01324/68A patent/GB1222426A/en not_active Expired
-
1969
- 1969-02-26 US US802656*A patent/US3644237A/en not_active Expired - Lifetime
- 1969-02-28 DE DE19691910224 patent/DE1910224A1/de active Pending
- 1969-03-05 FR FR6906043A patent/FR2003473A1/fr not_active Withdrawn
- 1969-03-06 ES ES364454A patent/ES364454A1/es not_active Expired
- 1969-03-07 DK DK127869AA patent/DK125801B/da unknown
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0473399A3 (en) * | 1990-08-31 | 1993-01-13 | Cape Industries | Polyester polyols from tall oil fatty acid maleic anhydride, and aromatic polyester polyols |
Also Published As
| Publication number | Publication date |
|---|---|
| US3644237A (en) | 1972-02-22 |
| GB1222426A (en) | 1971-02-10 |
| FR2003473A1 (https=) | 1969-11-07 |
| ES364454A1 (es) | 1971-02-01 |
| DK125801B (da) | 1973-05-07 |
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Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| SH | Request for examination between 03.10.1968 and 22.04.1971 |