GB1528045A - Polyisocyanates - Google Patents
PolyisocyanatesInfo
- Publication number
- GB1528045A GB1528045A GB3285275A GB3285275A GB1528045A GB 1528045 A GB1528045 A GB 1528045A GB 3285275 A GB3285275 A GB 3285275A GB 3285275 A GB3285275 A GB 3285275A GB 1528045 A GB1528045 A GB 1528045A
- Authority
- GB
- United Kingdom
- Prior art keywords
- diisocyanate
- tri
- diphenylmethane
- diphenylmethane diisocyanate
- glycol
- 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
- 239000005056 polyisocyanate Substances 0.000 title abstract 3
- 229920001228 polyisocyanate Polymers 0.000 title abstract 3
- 239000000203 mixture Substances 0.000 abstract 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 abstract 5
- KKEYFWRCBNTPAC-UHFFFAOYSA-N Terephthalic acid Chemical compound OC(=O)C1=CC=C(C(O)=O)C=C1 KKEYFWRCBNTPAC-UHFFFAOYSA-N 0.000 abstract 4
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical compound CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 3
- 150000002009 diols Chemical class 0.000 abstract 3
- SZXQTJUDPRGNJN-UHFFFAOYSA-N dipropylene glycol Chemical compound OCCCOCCCO SZXQTJUDPRGNJN-UHFFFAOYSA-N 0.000 abstract 3
- PUPZLCDOIYMWBV-UHFFFAOYSA-N (+/-)-1,3-Butanediol Chemical compound CC(O)CCO PUPZLCDOIYMWBV-UHFFFAOYSA-N 0.000 abstract 2
- NBIIXXVUZAFLBC-UHFFFAOYSA-N Phosphoric acid Chemical compound OP(O)(O)=O NBIIXXVUZAFLBC-UHFFFAOYSA-N 0.000 abstract 2
- WNLRTRBMVRJNCN-UHFFFAOYSA-N adipic acid Chemical compound OC(=O)CCCCC(O)=O WNLRTRBMVRJNCN-UHFFFAOYSA-N 0.000 abstract 2
- PASDCCFISLVPSO-UHFFFAOYSA-N benzoyl chloride Chemical compound ClC(=O)C1=CC=CC=C1 PASDCCFISLVPSO-UHFFFAOYSA-N 0.000 abstract 2
- HIFVAOIJYDXIJG-UHFFFAOYSA-N benzylbenzene;isocyanic acid Chemical class N=C=O.N=C=O.C=1C=CC=CC=1CC1=CC=CC=C1 HIFVAOIJYDXIJG-UHFFFAOYSA-N 0.000 abstract 2
- 125000001183 hydrocarbyl group Chemical group 0.000 abstract 2
- 239000007788 liquid Substances 0.000 abstract 2
- 229920001451 polypropylene glycol Polymers 0.000 abstract 2
- FYSNRJHAOHDILO-UHFFFAOYSA-N thionyl chloride Chemical compound ClS(Cl)=O FYSNRJHAOHDILO-UHFFFAOYSA-N 0.000 abstract 2
- 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 abstract 1
- YGYAWVDWMABLBF-UHFFFAOYSA-N Phosgene Chemical compound ClC(Cl)=O YGYAWVDWMABLBF-UHFFFAOYSA-N 0.000 abstract 1
- 239000002202 Polyethylene glycol Substances 0.000 abstract 1
- 229920005830 Polyurethane Foam Polymers 0.000 abstract 1
- XSTXAVWGXDQKEL-UHFFFAOYSA-N Trichloroethylene Chemical compound ClC=C(Cl)Cl XSTXAVWGXDQKEL-UHFFFAOYSA-N 0.000 abstract 1
- BWVAOONFBYYRHY-UHFFFAOYSA-N [4-(hydroxymethyl)phenyl]methanol Chemical compound OCC1=CC=C(CO)C=C1 BWVAOONFBYYRHY-UHFFFAOYSA-N 0.000 abstract 1
- 239000001361 adipic acid Substances 0.000 abstract 1
- 235000011037 adipic acid Nutrition 0.000 abstract 1
- 229910000147 aluminium phosphate Inorganic materials 0.000 abstract 1
- 239000003963 antioxidant agent Substances 0.000 abstract 1
- 235000006708 antioxidants Nutrition 0.000 abstract 1
- 235000019437 butane-1,3-diol Nutrition 0.000 abstract 1
- VPKDCDLSJZCGKE-UHFFFAOYSA-N carbodiimide group Chemical group N=C=N VPKDCDLSJZCGKE-UHFFFAOYSA-N 0.000 abstract 1
- KXDHJXZQYSOELW-UHFFFAOYSA-N carbonic acid monoamide Natural products NC(O)=O KXDHJXZQYSOELW-UHFFFAOYSA-N 0.000 abstract 1
- 239000007795 chemical reaction product Substances 0.000 abstract 1
- 125000004218 chloromethyl group Chemical group [H]C([H])(Cl)* 0.000 abstract 1
- 125000005442 diisocyanate group Chemical group 0.000 abstract 1
- XXMIOPMDWAUFGU-UHFFFAOYSA-N hexane-1,6-diol Chemical compound OCCCCCCO XXMIOPMDWAUFGU-UHFFFAOYSA-N 0.000 abstract 1
- 229910052739 hydrogen Inorganic materials 0.000 abstract 1
- 239000001257 hydrogen Substances 0.000 abstract 1
- 125000004435 hydrogen atom Chemical group [H]* 0.000 abstract 1
- 150000002440 hydroxy compounds Chemical class 0.000 abstract 1
- IQPQWNKOIGAROB-UHFFFAOYSA-N isocyanate group Chemical group [N-]=C=O IQPQWNKOIGAROB-UHFFFAOYSA-N 0.000 abstract 1
- 238000004519 manufacturing process Methods 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 235000011007 phosphoric acid Nutrition 0.000 abstract 1
- 229920001223 polyethylene glycol Polymers 0.000 abstract 1
- 239000004814 polyurethane Substances 0.000 abstract 1
- 229920002635 polyurethane Polymers 0.000 abstract 1
- 239000011496 polyurethane foam Substances 0.000 abstract 1
- 229930195734 saturated hydrocarbon Chemical group 0.000 abstract 1
- 239000003381 stabilizer Substances 0.000 abstract 1
- 239000000126 substance Substances 0.000 abstract 1
- KJAMZCVTJDTESW-UHFFFAOYSA-N tiracizine Chemical compound C1CC2=CC=CC=C2N(C(=O)CN(C)C)C2=CC(NC(=O)OCC)=CC=C21 KJAMZCVTJDTESW-UHFFFAOYSA-N 0.000 abstract 1
- 150000003627 tricarboxylic acid derivatives Chemical class 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
- 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
- C08G18/797—Nitrogen characterised by the polyisocyanates used, these having groups formed by oligomerisation of isocyanates or isothiocyanates containing carbodiimide and/or uretone-imine groups
-
- 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
- C08G18/80—Masked polyisocyanates
- C08G18/8003—Masked polyisocyanates masked with compounds having at least two groups containing active hydrogen
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
Abstract
1528045 Diphenylmethane diisocyanate composition IMPERIAL CHEMICAL INDUSTRIES Ltd 28 June 1976 [6 Aug 1975] 32852/75 Heading C3R A diphenylmethane diisocyanate composition comprises diphenylmethane diisocyanate or uretonimine modified diphenylmethane diisocyanate, in which from 3À5-35% of the isocyanate groups have been reacted with either (1) a di- or tri-hydroxy compound of the formula wherein R and R<SP>1</SP> are hydrogen, phenyl or saturated hydrocarbon groups or one of R and R<SP>1</SP> but not both may be chloromethyl, n is zero or an integer from 1-6, p is 1-10, m is 2 or 3 and X is C=O, S=O, SO 2 , #P=O, O=P(R<SP>11</SP>)=, wherein R<SP>11</SP> is hydrocarbyl, or X is the residue of a di- or tricarboxylic or carbamic acid, or (2) a mixture of di- or tri-hydroxy compounds containing at least 50% wt. of a di- or tri-hydroxy compound of the above formula, the remainder being a further diol or triol. The diphenyl-methane diisocyanate may be the 4,4<SP>1</SP> and/or the 2,4<SP>1</SP> isomer(s). The uretonimine modified diphenylmethane diisocyanate is preferably one in which from 3À5 to 35% of the NCO groups were first converted to carbodiimide groups followed by uretonimine -formation. Examples of di- or tri-hydroxy compounds of the above formula are bis-2-hydroxypropyloxalate, -succinate, -glutarate, -adipate, or -carbonate and analogues based on dipropylene glycol or polypropylene glycols. Examples of further diols are those of the formula where R, R<SP>1</SP>, n and p are as defined above. Suitable such diols are polyethylene glycol, di- or tri-propylene glycol, polypropylene glycol, 1,3-butane-diol, 1,6-hexanediol and 1,4-bishydroxymethylbenzene. Stabilizers, e.g. benzoyl chloride, thionyl chloride, adipic acid, phosphoric acid or anti-oxidants may be added before, during or after the reaction of the diisocyanate and the hydroxy compound(s). The liquid polyisocyanate compositions can be used in the manufacture of polyurethanes, particularly microcellular polyurethane foams. In the Examples liquid polyisocyanate compositions are prepared (1) by reacting diphenylmethane- 4,4<SP>1</SP>-diisocyanate with either a dipropylene glycol/terephthalic acid oligomer or a propylene glycol/terephthalic acid oligomer; or (2) by reacting a dipropylene glycol/phosgene reaction product with diphenylmethane-4,4<SP>1</SP>-diisocyanate, or a uretonimine modified diphenylmethane-4,4<SP>1</SP>-diisocyanate in the presence of benzoyl chloride, or a mixture of the 4,4<SP>1</SP>- and 2,4<SP>1</SP>- (81 : 18) isomers of diphenylmethane diisocyanate.
Priority Applications (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3285275A GB1528045A (en) | 1976-06-28 | 1976-06-28 | Polyisocyanates |
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| GB3285275A GB1528045A (en) | 1976-06-28 | 1976-06-28 | Polyisocyanates |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1528045A true GB1528045A (en) | 1978-10-11 |
Family
ID=10344978
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB3285275A Expired GB1528045A (en) | 1976-06-28 | 1976-06-28 | Polyisocyanates |
Country Status (1)
| Country | Link |
|---|---|
| GB (1) | GB1528045A (en) |
Cited By (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013487A1 (en) * | 1978-12-11 | 1980-07-23 | Imperial Chemical Industries Plc | Modified diisocyanate compositions and polyurethanes thereof |
-
1976
- 1976-06-28 GB GB3285275A patent/GB1528045A/en not_active Expired
Cited By (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| EP0013487A1 (en) * | 1978-12-11 | 1980-07-23 | Imperial Chemical Industries Plc | Modified diisocyanate compositions and polyurethanes thereof |
| US4448938A (en) * | 1978-12-11 | 1984-05-15 | Imperial Chemical Industries Plc | Modified isocyanate compositions, their production and uses for polyurethane manufacture |
Similar Documents
| Publication | Publication Date | Title |
|---|---|---|
| US4448938A (en) | Modified isocyanate compositions, their production and uses for polyurethane manufacture | |
| US3766148A (en) | Polyurethane elastomers prepared from 4,4 - methylene-bis(cyclohexyl isocyanate),polyol and methylene dianiline | |
| US3405077A (en) | Process for making soft polyurethane foams and product | |
| GB1572781A (en) | Low-temperature storage stable liquid diphenylmethyne diisocyanates | |
| CA1165500A (en) | Process for the preparation of flexible polyurethane foams with improved resistance to hydrolysis and good die cuttability | |
| GB1444192A (en) | Polyisocyanate compositions | |
| US3793268A (en) | Process for the production of polyurethane foam resins | |
| EP0422811B1 (en) | Process for producing a flexible polyurethane foam | |
| GB1448179A (en) | Method of manufacturing moulded polyurethane products | |
| US4087412A (en) | Organotin catalyst system for isocyanate reactions | |
| GB1311095A (en) | Alkylene oxide orthotolylene diamine compositions | |
| GB1241080A (en) | Polyurethane compositions | |
| GB1450523A (en) | Process for the production of polyisocyanates 2,4,6-tri | |
| GB1376863A (en) | Fireretardant polyurethanes and polyureas | |
| EP0398304B1 (en) | Flexible polyurethane foams and process for preparing them | |
| CA2044526C (en) | Process for the production of substantially closed-cell rigid foams containing urethane, urea and buiret groups showing excellent adhesion to solid surfaces and their use | |
| EP0130089A2 (en) | Low temperature, storage stable mixtures of polyester prepolymers and flow modifiers | |
| GB1528045A (en) | Polyisocyanates | |
| EP2360197A1 (en) | Flame-retardant material containing polyisocyanate prepolymers stable in storage | |
| EP0480090A1 (en) | Polyisocyanate compositions and their use in the preparation of flexible polyurethane foams | |
| US5350780A (en) | Process for the preparation of substantially closed-cell rigid foams containing urethane, urea, biuret, and isocyanurate groups and a method of use thereof | |
| US3681288A (en) | Storage-stable polyurethane prepolymers containing malonitrile | |
| GB1535783A (en) | Preparation of urethane polymers | |
| EP0155585A1 (en) | Activating plasticizer for urethane prepolymers and complex of alkali metal salt with 4,4'-methylenedianiline | |
| CA2325034A1 (en) | Stabilisation of organic polyisocyanates |
Legal Events
| Date | Code | Title | Description |
|---|---|---|---|
| PS | Patent sealed | ||
| PCNP | Patent ceased through non-payment of renewal fee |