GB1073664A - Polyurethanes - Google Patents
PolyurethanesInfo
- Publication number
- GB1073664A GB1073664A GB5367566A GB5367566A GB1073664A GB 1073664 A GB1073664 A GB 1073664A GB 5367566 A GB5367566 A GB 5367566A GB 5367566 A GB5367566 A GB 5367566A GB 1073664 A GB1073664 A GB 1073664A
- Authority
- GB
- United Kingdom
- Prior art keywords
- prepared
- formaldehyde
- aniline
- reaction
- foams
- 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
- 239000004814 polyurethane Substances 0.000 title abstract 2
- 229920002635 polyurethane Polymers 0.000 title abstract 2
- -1 aliphatic aldehydes Chemical class 0.000 abstract 5
- RTZKZFJDLAIYFH-UHFFFAOYSA-N Diethyl ether Chemical compound CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 3
- WSFSSNUMVMOOMR-UHFFFAOYSA-N Formaldehyde Chemical compound O=C WSFSSNUMVMOOMR-UHFFFAOYSA-N 0.000 abstract 3
- PEDCQBHIVMGVHV-UHFFFAOYSA-N Glycerine Chemical compound OCC(O)CO PEDCQBHIVMGVHV-UHFFFAOYSA-N 0.000 abstract 3
- SJRJJKPEHAURKC-UHFFFAOYSA-N N-Methylmorpholine Chemical compound CN1CCOCC1 SJRJJKPEHAURKC-UHFFFAOYSA-N 0.000 abstract 3
- ZMANZCXQSJIPKH-UHFFFAOYSA-N Triethylamine Chemical compound CCN(CC)CC ZMANZCXQSJIPKH-UHFFFAOYSA-N 0.000 abstract 3
- 239000006260 foam Substances 0.000 abstract 3
- DYDNPESBYVVLBO-UHFFFAOYSA-N formanilide Chemical compound O=CNC1=CC=CC=C1 DYDNPESBYVVLBO-UHFFFAOYSA-N 0.000 abstract 3
- VLKZOEOYAKHREP-UHFFFAOYSA-N n-Hexane Chemical compound CCCCCC VLKZOEOYAKHREP-UHFFFAOYSA-N 0.000 abstract 3
- 239000005056 polyisocyanate Substances 0.000 abstract 3
- 229920001228 polyisocyanate Polymers 0.000 abstract 3
- DVKJHBMWWAPEIU-UHFFFAOYSA-N toluene 2,4-diisocyanate Chemical class CC1=CC=C(N=C=O)C=C1N=C=O DVKJHBMWWAPEIU-UHFFFAOYSA-N 0.000 abstract 3
- PAYRUJLWNCNPSJ-UHFFFAOYSA-N Aniline Chemical compound NC1=CC=CC=C1 PAYRUJLWNCNPSJ-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- YMWUJEATGCHHMB-UHFFFAOYSA-N Dichloromethane Chemical compound ClCCl YMWUJEATGCHHMB-UHFFFAOYSA-N 0.000 abstract 2
- IMNFDUFMRHMDMM-UHFFFAOYSA-N N-Heptane Chemical compound CCCCCCC IMNFDUFMRHMDMM-UHFFFAOYSA-N 0.000 abstract 2
- OFBQJSOFQDEBGM-UHFFFAOYSA-N Pentane Chemical compound CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 2
- JUJWROOIHBZHMG-UHFFFAOYSA-N Pyridine Chemical compound C1=CC=NC=C1 JUJWROOIHBZHMG-UHFFFAOYSA-N 0.000 abstract 2
- 150000004982 aromatic amines Chemical class 0.000 abstract 2
- 125000003118 aryl group Chemical group 0.000 abstract 2
- 238000005187 foaming Methods 0.000 abstract 2
- 125000002485 formyl group Chemical class [H]C(*)=O 0.000 abstract 2
- KDYFGRWQOYBRFD-UHFFFAOYSA-N succinic acid Chemical compound OC(=O)CCC(O)=O KDYFGRWQOYBRFD-UHFFFAOYSA-N 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 125000001989 1,3-phenylene group Chemical group [H]C1=C([H])C([*:1])=C([H])C([*:2])=C1[H] 0.000 abstract 1
- 125000001140 1,4-phenylene group Chemical group [H]C1=C([H])C([*:2])=C([H])C([H])=C1[*:1] 0.000 abstract 1
- PAMIQIKDUOTOBW-UHFFFAOYSA-N 1-methylpiperidine Chemical compound CN1CCCCC1 PAMIQIKDUOTOBW-UHFFFAOYSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-FSIIMWSLSA-N D-Glucitol Natural products OC[C@H](O)[C@H](O)[C@@H](O)[C@H](O)CO FBPFZTCFMRRESA-FSIIMWSLSA-N 0.000 abstract 1
- FBPFZTCFMRRESA-JGWLITMVSA-N D-glucitol Chemical compound OC[C@H](O)[C@@H](O)[C@H](O)[C@H](O)CO FBPFZTCFMRRESA-JGWLITMVSA-N 0.000 abstract 1
- JNCMHMUGTWEVOZ-UHFFFAOYSA-N F[CH]F Chemical compound F[CH]F JNCMHMUGTWEVOZ-UHFFFAOYSA-N 0.000 abstract 1
- 108010081348 HRT1 protein Hairy Proteins 0.000 abstract 1
- 102100021881 Hairy/enhancer-of-split related with YRPW motif protein 1 Human genes 0.000 abstract 1
- UEEJHVSXFDXPFK-UHFFFAOYSA-N N-dimethylaminoethanol Chemical compound CN(C)CCO UEEJHVSXFDXPFK-UHFFFAOYSA-N 0.000 abstract 1
- QORUGOXNWQUALA-UHFFFAOYSA-N N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 Chemical compound N=C=O.N=C=O.N=C=O.C1=CC=C(C(C2=CC=CC=C2)C2=CC=CC=C2)C=C1 QORUGOXNWQUALA-UHFFFAOYSA-N 0.000 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 239000002253 acid Substances 0.000 abstract 1
- 150000001298 alcohols Chemical class 0.000 abstract 1
- 229920005628 alkoxylated polyol Polymers 0.000 abstract 1
- 150000001412 amines Chemical class 0.000 abstract 1
- 239000004305 biphenyl Substances 0.000 abstract 1
- 235000010290 biphenyl Nutrition 0.000 abstract 1
- 125000002529 biphenylenyl group Chemical group C1(=CC=CC=2C3=CC=CC=C3C12)* 0.000 abstract 1
- 229920001400 block copolymer Polymers 0.000 abstract 1
- JLCRXCPXQLBSEM-UHFFFAOYSA-N calcium diisocyanate Chemical compound [Ca++].[N-]=C=O.[N-]=C=O JLCRXCPXQLBSEM-UHFFFAOYSA-N 0.000 abstract 1
- 239000003054 catalyst Substances 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- HRYZWHHZPQKTII-UHFFFAOYSA-N chloroethane Chemical compound CCCl HRYZWHHZPQKTII-UHFFFAOYSA-N 0.000 abstract 1
- 229960002887 deanol Drugs 0.000 abstract 1
- AZSZCFSOHXEJQE-UHFFFAOYSA-N dibromodifluoromethane Chemical compound FC(F)(Br)Br AZSZCFSOHXEJQE-UHFFFAOYSA-N 0.000 abstract 1
- UMNKXPULIDJLSU-UHFFFAOYSA-N dichlorofluoromethane Chemical compound FC(Cl)Cl UMNKXPULIDJLSU-UHFFFAOYSA-N 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- 239000012972 dimethylethanolamine Substances 0.000 abstract 1
- KPUWHANPEXNPJT-UHFFFAOYSA-N disiloxane Chemical class [SiH3]O[SiH3] KPUWHANPEXNPJT-UHFFFAOYSA-N 0.000 abstract 1
- 239000000975 dye Substances 0.000 abstract 1
- 239000000945 filler Substances 0.000 abstract 1
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 1
- 239000012948 isocyanate Substances 0.000 abstract 1
- 150000002513 isocyanates Chemical class 0.000 abstract 1
- 238000000034 method Methods 0.000 abstract 1
- 125000000325 methylidene group Chemical group [H]C([H])=* 0.000 abstract 1
- MXHTZQSKTCCMFG-UHFFFAOYSA-N n,n-dibenzyl-1-phenylmethanamine Chemical compound C=1C=CC=CC=1CN(CC=1C=CC=CC=1)CC1=CC=CC=C1 MXHTZQSKTCCMFG-UHFFFAOYSA-N 0.000 abstract 1
- WXZMFSXDPGVJKK-UHFFFAOYSA-N pentaerythritol Chemical compound OCC(CO)(CO)CO WXZMFSXDPGVJKK-UHFFFAOYSA-N 0.000 abstract 1
- ZUOUZKKEUPVFJK-UHFFFAOYSA-N phenylbenzene Natural products C1=CC=CC=C1C1=CC=CC=C1 ZUOUZKKEUPVFJK-UHFFFAOYSA-N 0.000 abstract 1
- 239000004014 plasticizer Substances 0.000 abstract 1
- 229920005862 polyol Polymers 0.000 abstract 1
- 150000003077 polyols Chemical class 0.000 abstract 1
- 239000000047 product Substances 0.000 abstract 1
- UMJSCPRVCHMLSP-UHFFFAOYSA-N pyridine Natural products COC1=CC=CN=C1 UMJSCPRVCHMLSP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000600 sorbitol Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- 239000001384 succinic acid Substances 0.000 abstract 1
- 235000000346 sugar Nutrition 0.000 abstract 1
- 150000008163 sugars Chemical class 0.000 abstract 1
- 239000004094 surface-active agent Substances 0.000 abstract 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract 1
- ZBZJXHCVGLJWFG-UHFFFAOYSA-N trichloromethyl(.) Chemical compound Cl[C](Cl)Cl ZBZJXHCVGLJWFG-UHFFFAOYSA-N 0.000 abstract 1
- XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 abstract 1
- 239000000080 wetting agent Substances 0.000 abstract 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
- C08G12/00—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen
- C08G12/02—Condensation polymers of aldehydes or ketones with only compounds containing hydrogen attached to nitrogen of aldehydes
- C08G12/40—Chemically modified polycondensates
- C08G12/42—Chemically modified polycondensates by etherifying
- C08G12/421—Chemically modified polycondensates by etherifying of polycondensates based on acyclic or carbocyclic compounds
-
- 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
- C08G18/40—High-molecular-weight compounds
- C08G18/54—Polycondensates of aldehydes
- C08G18/546—Oxyalkylated polycondensates of aldehydes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- General Chemical & Material Sciences (AREA)
- Polyurethanes Or Polyureas (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
- Phenolic Resins Or Amino Resins (AREA)
Abstract
A polyurethane is prepared by reacting a polyisocyanate with a polyarylaminopolyether which is obtained by reacting an organic cylic oxide with the reaction product of an arylamine and an aldehyde and which has the general formula <FORM:1073664/C3/1> wherein Ar is the residue of the arylamine, R1 of the aldehyde and R of the organic oxide, n being 1-20 and X being a whole number (see Specification 1,073,663). The preferred polyarylaminopolyethers are prepared from aniline, formaldehyde and propylene oxide, but many other suitable amines, aromatic and aliphatic aldehydes, and aromatic and aliphatic cyclic oxides are listed. The toluene diisocyanates and 3:31-bitolylene-4:41-diisocyanate are the preferred polyisocyanates; others suitable are ethylene, tetramethylene, hexamethylene, cyclohexene-1:2, m- and p-phenylene, 1:5-naphthalene, p,p1-methylene diphenyl, 3:31-dichloro - 4:41 biphenylene, 4 - chloro - 1:3-phenylene, and thiodipropyl diisocyanates and triphenylmethane triisocyanate, and calcium diisocyanate. An excess of 15-35% of isocyanate over hydroxy groups is preferably used, giving a "prepolymer". In the preparation of foams a siloxane surfactant, e.g. a siloxaneoxyalkylene block copolymer, may be used, e.g. in amounts of 0.25-2 wt. per cent of the total. Foaming may be achieved by physical means, e.g. using CHFCl2, CHCl3, CFCl3, CCl4, CH2Cl2, CHFCl, CH3.CH2.CHF2, CH3.CF2.CH3, CCl3.CF2.CH3, C2Cl4Br2, CF2Br2, C2F4Cl2, C2F3Cl3, C2H5Cl, pentane, hexane, heptane, cylohexene, and diethyl ether, amounting, e.g. to 10-60% of the total weight, or by chemical means e.g. using water or a dibasic acid e.g. succinic acid. A basic foaming catalyst is usually employed e.g. 0.5-3 wt. per cent of methyl piperidine, tribenzylamine, pyridine, N:N:N1:N1 - tetramethylbutanediamine, triethylamine, N-methylmorpholine, dimethylethanolamine and N:N1-bis(2-hydroxypropyl)-2-methylpiperazine. Suitable polyols for reaction with the prepolymer include alkoxylated polyols including glycerol, pentaerythritol and a list of sugars and similar alcohols. Conventional dyes, fillers, softeners, plasticizers, wetting agents etc. may be added. In examples propoxylated aniline-formaldehyde products are converted into prepolymers with toluene diisocyanate, and foams are prepared by a two-stage reaction of these with futher polyarylaminopolyethers. In Examples IV and V foams are prepared by reaction of the propoxylated aniline-formaldehyde with a prepolymer from sorbitol and toluene diisocyanate or with a polyisocyanate from phosgene and an aniline-formaldehyde product-the latter a "one-shot" process.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US32392363A | 1963-11-15 | 1963-11-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1073664A true GB1073664A (en) | 1967-06-28 |
Family
ID=23261296
Family Applications (2)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB5367566A Expired GB1073664A (en) | 1963-11-15 | 1964-06-01 | Polyurethanes |
| GB2252564A Expired GB1073663A (en) | 1963-11-15 | 1964-06-01 | Polyarylaminopolyethers |
Family Applications After (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB2252564A Expired GB1073663A (en) | 1963-11-15 | 1964-06-01 | Polyarylaminopolyethers |
Country Status (1)
| Country | Link |
|---|---|
| GB (2) | GB1073664A (en) |
Cited By (3)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5872292A (en) * | 1997-01-24 | 1999-02-16 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| US6004482A (en) * | 1997-12-24 | 1999-12-21 | Bayer Corporation | Stable aromatic amine composition, and a process for preparing color stable aromatic amines |
| US6031137A (en) * | 1998-05-29 | 2000-02-29 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
-
1964
- 1964-06-01 GB GB5367566A patent/GB1073664A/en not_active Expired
- 1964-06-01 GB GB2252564A patent/GB1073663A/en not_active Expired
Cited By (4)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US5872292A (en) * | 1997-01-24 | 1999-02-16 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| US6004482A (en) * | 1997-12-24 | 1999-12-21 | Bayer Corporation | Stable aromatic amine composition, and a process for preparing color stable aromatic amines |
| US6031137A (en) * | 1998-05-29 | 2000-02-29 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
| US6353137B2 (en) | 1998-05-29 | 2002-03-05 | Bayer Corporation | Stable aromatic amine composition, a process for preparing color stable aromatic amines, and the production of light colored aromatic amine-based polyether polyols |
Also Published As
| Publication number | Publication date |
|---|---|
| GB1073663A (en) | 1967-06-28 |
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