GB1012653A - Polyurethane foams and processes for their preparation - Google Patents
Polyurethane foams and processes for their preparationInfo
- Publication number
- GB1012653A GB1012653A GB51204/63A GB5120463A GB1012653A GB 1012653 A GB1012653 A GB 1012653A GB 51204/63 A GB51204/63 A GB 51204/63A GB 5120463 A GB5120463 A GB 5120463A GB 1012653 A GB1012653 A GB 1012653A
- Authority
- GB
- United Kingdom
- Prior art keywords
- polyol
- diisocyanate
- weight
- antimony
- preferred
- 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
- 229920005830 Polyurethane Foam Polymers 0.000 title abstract 3
- 239000011496 polyurethane foam Substances 0.000 title abstract 3
- 125000005442 diisocyanate group Chemical group 0.000 abstract 7
- 229920005862 polyol Polymers 0.000 abstract 7
- RTZKZFJDLAIYFH-UHFFFAOYSA-N ether Substances CCOCC RTZKZFJDLAIYFH-UHFFFAOYSA-N 0.000 abstract 6
- 150000003077 polyols Chemical class 0.000 abstract 5
- 229910052787 antimony Inorganic materials 0.000 abstract 4
- WATWJIUSRGPENY-UHFFFAOYSA-N antimony atom Chemical compound [Sb] WATWJIUSRGPENY-UHFFFAOYSA-N 0.000 abstract 4
- -1 aromatic diisocyanate compound Chemical class 0.000 abstract 4
- 229910052736 halogen Inorganic materials 0.000 abstract 4
- 150000002367 halogens Chemical class 0.000 abstract 3
- 239000000203 mixture Substances 0.000 abstract 3
- OFBQJSOFQDEBGM-UHFFFAOYSA-N n-pentane Natural products CCCCC OFBQJSOFQDEBGM-UHFFFAOYSA-N 0.000 abstract 3
- CSCPPACGZOOCGX-UHFFFAOYSA-N Acetone Chemical compound CC(C)=O CSCPPACGZOOCGX-UHFFFAOYSA-N 0.000 abstract 2
- ZAMOUSCENKQFHK-UHFFFAOYSA-N Chlorine atom Chemical compound [Cl] ZAMOUSCENKQFHK-UHFFFAOYSA-N 0.000 abstract 2
- HEDRZPFGACZZDS-UHFFFAOYSA-N Chloroform Chemical compound ClC(Cl)Cl HEDRZPFGACZZDS-UHFFFAOYSA-N 0.000 abstract 2
- ADCOVFLJGNWWNZ-UHFFFAOYSA-N antimony trioxide Chemical compound O=[Sb]O[Sb]=O ADCOVFLJGNWWNZ-UHFFFAOYSA-N 0.000 abstract 2
- GDTBXPJZTBHREO-UHFFFAOYSA-N bromine Substances BrBr GDTBXPJZTBHREO-UHFFFAOYSA-N 0.000 abstract 2
- 229910052794 bromium Inorganic materials 0.000 abstract 2
- 239000003054 catalyst Substances 0.000 abstract 2
- 239000003795 chemical substances by application Substances 0.000 abstract 2
- 229910052801 chlorine Inorganic materials 0.000 abstract 2
- 239000000460 chlorine Substances 0.000 abstract 2
- 230000007062 hydrolysis Effects 0.000 abstract 2
- 238000006460 hydrolysis reaction Methods 0.000 abstract 2
- 125000002887 hydroxy group Chemical group [H]O* 0.000 abstract 2
- 229920001281 polyalkylene Polymers 0.000 abstract 2
- OUULRIDHGPHMNQ-UHFFFAOYSA-N stibane Chemical compound [SbH3] OUULRIDHGPHMNQ-UHFFFAOYSA-N 0.000 abstract 2
- 239000004094 surface-active agent Substances 0.000 abstract 2
- VZGDMQKNWNREIO-UHFFFAOYSA-N tetrachloromethane Chemical compound ClC(Cl)(Cl)Cl VZGDMQKNWNREIO-UHFFFAOYSA-N 0.000 abstract 2
- 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 2
- IMNIMPAHZVJRPE-UHFFFAOYSA-N triethylenediamine Chemical compound C1CN2CCN1CC2 IMNIMPAHZVJRPE-UHFFFAOYSA-N 0.000 abstract 2
- WKBOTKDWSSQWDR-UHFFFAOYSA-N Bromine atom Chemical compound [Br] WKBOTKDWSSQWDR-UHFFFAOYSA-N 0.000 abstract 1
- IAYPIBMASNFSPL-UHFFFAOYSA-N Ethylene oxide Chemical compound C1CO1 IAYPIBMASNFSPL-UHFFFAOYSA-N 0.000 abstract 1
- PIICEJLVQHRZGT-UHFFFAOYSA-N Ethylenediamine Chemical compound NCCN PIICEJLVQHRZGT-UHFFFAOYSA-N 0.000 abstract 1
- OAICVXFJPJFONN-UHFFFAOYSA-N Phosphorus Chemical compound [P] OAICVXFJPJFONN-UHFFFAOYSA-N 0.000 abstract 1
- DNIAPMSPPWPWGF-UHFFFAOYSA-N Propylene glycol Chemical class CC(O)CO DNIAPMSPPWPWGF-UHFFFAOYSA-N 0.000 abstract 1
- GOOHAUXETOMSMM-UHFFFAOYSA-N Propylene oxide Chemical compound CC1CO1 GOOHAUXETOMSMM-UHFFFAOYSA-N 0.000 abstract 1
- 229910000074 antimony hydride Inorganic materials 0.000 abstract 1
- 125000003118 aryl group Chemical group 0.000 abstract 1
- 230000015572 biosynthetic process Effects 0.000 abstract 1
- 229920001400 block copolymer Polymers 0.000 abstract 1
- 239000001273 butane Substances 0.000 abstract 1
- 238000006243 chemical reaction Methods 0.000 abstract 1
- 150000001875 compounds Chemical class 0.000 abstract 1
- 239000006260 foam Substances 0.000 abstract 1
- 230000008014 freezing Effects 0.000 abstract 1
- 238000007710 freezing Methods 0.000 abstract 1
- 229930195733 hydrocarbon Natural products 0.000 abstract 1
- 150000002430 hydrocarbons Chemical class 0.000 abstract 1
- 239000000463 material Substances 0.000 abstract 1
- IJDNQMDRQITEOD-UHFFFAOYSA-N n-butane Chemical compound CCCC IJDNQMDRQITEOD-UHFFFAOYSA-N 0.000 abstract 1
- 125000003854 p-chlorophenyl group Chemical group [H]C1=C([H])C(*)=C([H])C([H])=C1Cl 0.000 abstract 1
- 125000001037 p-tolyl group Chemical group [H]C1=C([H])C(=C([H])C([H])=C1*)C([H])([H])[H] 0.000 abstract 1
- 125000001997 phenyl group Chemical group [H]C1=C([H])C([H])=C(*)C([H])=C1[H] 0.000 abstract 1
- 229910052698 phosphorus Inorganic materials 0.000 abstract 1
- 239000011574 phosphorus Substances 0.000 abstract 1
- 229920005906 polyester polyol Polymers 0.000 abstract 1
- 235000013772 propylene glycol Nutrition 0.000 abstract 1
- 229940094938 stannous 2-ethylhexanoate Drugs 0.000 abstract 1
- 125000001424 substituent group Chemical group 0.000 abstract 1
- 150000003512 tertiary amines Chemical class 0.000 abstract 1
- KSBAEPSJVUENNK-UHFFFAOYSA-L tin(ii) 2-ethylhexanoate Chemical compound [Sn+2].CCCCC(CC)C([O-])=O.CCCCC(CC)C([O-])=O KSBAEPSJVUENNK-UHFFFAOYSA-L 0.000 abstract 1
- CYRMSUTZVYGINF-UHFFFAOYSA-N trichlorofluoromethane Chemical compound FC(Cl)(Cl)Cl CYRMSUTZVYGINF-UHFFFAOYSA-N 0.000 abstract 1
- 229940029284 trichlorofluoromethane Drugs 0.000 abstract 1
Classifications
-
- 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
- C08J9/0066—Use of inorganic compounding ingredients
-
- 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
- C08G18/773—Polyisocyanates or polyisothiocyanates having heteroatoms in addition to the isocyanate or isothiocyanate nitrogen and oxygen or sulfur halogens
-
- 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
- C08J9/0014—Use of organic additives
- C08J9/0057—Use of organic additives containing antimony, arsenic, or bismuth
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08K—Use of inorganic or non-macromolecular organic substances as compounding ingredients
- C08K5/00—Use of organic ingredients
- C08K5/59—Arsenic- or antimony-containing compounds
-
- 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
- C08L75/04—Polyurethanes
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
- C08L83/00—Compositions of macromolecular compounds obtained by reactions forming in the main chain of the macromolecule a linkage containing silicon with or without sulfur, nitrogen, oxygen or carbon only; Compositions of derivatives of such polymers
- C08L83/10—Block- or graft-copolymers containing polysiloxane sequences
- C08L83/12—Block- or graft-copolymers containing polysiloxane sequences containing polyether sequences
-
- 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
- C08J2375/04—Polyurethanes
Landscapes
- Chemical & Material Sciences (AREA)
- Health & Medical Sciences (AREA)
- Chemical Kinetics & Catalysis (AREA)
- Medicinal Chemistry (AREA)
- Polymers & Plastics (AREA)
- Organic Chemistry (AREA)
- Engineering & Computer Science (AREA)
- Materials Engineering (AREA)
- Inorganic Chemistry (AREA)
- Polyurethanes Or Polyureas (AREA)
Abstract
Polyurethane foam material is prepared by reacting an aromatic diisocyanate compound with a polymeric polyol having at least three hydroxyl groups per molecule and a hydroxyl number between 350 and 650 in contact with an expanding agent having a boiling-point between - 20 DEG C. and 80 DEG C., a catalyst for the isocyanate-polyol reaction, a surfactant which stabilizes polyurethane foam during foam formation and up to 6% by weight of antimony based on the combined weight of polyol and diisocyanate, the aromatic diisocyanate component comprising a mixture of aromatic diisocyanates having a freezing point of less than 26 DEG C., at least one diisocyanate having chlorine or bromine halogen as a ring substituent, the halogen being present in an amount of at least 2.5% by weight of polyol and diisocyanate component, and the antimony being present as antimony trioxide or a triaryl stibine or a mixture thereof, provided that when the weight per cent of halogen is less than 7% the amount of antimony is not less than that given by the formula: weight per cent antimony based on combined weight of polyol and diisocyanate component <FORM:1012653/C3/1> - 2 where X is the weight per cent of halogen based on the combined weight of polyol and diisocyanate component. The preferred diisocyanates are toluene diisocyanates and halogenated toluene diisocyanates, an additional preferred non-halogenated diisocyanate being 4,41-diisocyanatophenylmethane. Both polyalkylene ether polyols and polyester polyols may be used and may contain chlorine, bromine or phosphorus to impart increased flame resistance. Suitable expanding agents are butane, pentane, chloroform, acetone, carbon tetrachloride and diethyl ether whilst those preferred are fluorinated hydrocarbons especially trichlorofluoromethane The preferred triaryl stibines are those wherein the aryl group is phenyl, p-tolyl or p-chlorophenyl. Tertiary amines or organo tin compounds may be used as the catalyst, a mixture of triethylene diamine with stannous-2-ethylhexanoate being preferred. Useful surfactants are (a) those prepared by the sequential addition of propylene oxide and ethylene oxide to compounds such as ethylene diamine and propylene glycols, and (b) polydimethyl siloxane-polyalkylene ether block copolymers which are subject to slow hydrolysis or have been modified to be resistant to hydrolysis.
Applications Claiming Priority (1)
| Application Number | Priority Date | Filing Date | Title |
|---|---|---|---|
| US25150163A | 1963-01-15 | 1963-01-15 |
Publications (1)
| Publication Number | Publication Date |
|---|---|
| GB1012653A true GB1012653A (en) | 1965-12-08 |
Family
ID=22952250
Family Applications (1)
| Application Number | Title | Priority Date | Filing Date |
|---|---|---|---|
| GB51204/63A Expired GB1012653A (en) | 1963-01-15 | 1963-12-30 | Polyurethane foams and processes for their preparation |
Country Status (5)
| Country | Link |
|---|---|
| BE (1) | BE642478A (en) |
| DE (1) | DE1219672B (en) |
| FR (1) | FR1379500A (en) |
| GB (1) | GB1012653A (en) |
| NL (1) | NL302917A (en) |
Cited By (7)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547842A (en) * | 1969-08-05 | 1970-12-15 | American Cyanamid Co | Flame-retardant polyurethanes |
| DE102009033710A1 (en) | 2009-07-18 | 2011-01-20 | Evonik Goldschmidt Gmbh | Use of metal salts of a carboxylic acid in the production of polyurethane systems |
| DE102010003672A1 (en) | 2010-04-07 | 2011-10-13 | Evonik Goldschmidt Gmbh | Preparation and Use of Metal Salts of Alkyl Oxide and / or Aryl Alkoxylate Oligomers and Acid Terminated Polymers in the Preparation of Polyurethane Systems |
| EP2557101A1 (en) | 2011-08-11 | 2013-02-13 | Evonik Goldschmidt GmbH | Formula containing tin and/or zinc salts of ricinoleic acid, urea, polyethylene glycol and sugar alcohol and use of the formula in the production of polyurethane systems |
| EP2557100A1 (en) | 2011-08-11 | 2013-02-13 | Evonik Goldschmidt GmbH | Compound containing tin and/or zinc salts of ricinoleic acid, urea and at least one other tin carboxylate and use of the compound in the production of polyurethane systems |
| EP2752243A1 (en) | 2013-01-04 | 2014-07-09 | Evonik Industries AG | Use of tin salts of neodecanoic acid in the production of polyurethane systems |
| EP2762509A1 (en) | 2013-02-05 | 2014-08-06 | Evonik Industries AG | Composition for use in the production of polyurethane systems |
Families Citing this family (2)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3479304A (en) * | 1966-03-31 | 1969-11-18 | Du Pont | Preparation of flame-resistant flexible foams from halogenated tolylene diisocyanate |
| CN116278518B (en) * | 2023-03-20 | 2023-08-29 | 安徽誉林新材料科技有限公司 | Puncture-proof and explosion-proof polyurethane tire and preparation method thereof |
Family Cites Families (1)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| DE1112285B (en) * | 1959-01-17 | 1961-08-03 | Bayer Ag | Process for the production of foams containing urethane groups |
-
1963
- 1963-12-30 GB GB51204/63A patent/GB1012653A/en not_active Expired
- 1963-12-31 NL NL302917A patent/NL302917A/en unknown
-
1964
- 1964-01-10 DE DEP33346A patent/DE1219672B/en active Pending
- 1964-01-14 BE BE642478A patent/BE642478A/en unknown
- 1964-01-15 FR FR960336A patent/FR1379500A/en not_active Expired
Cited By (15)
| Publication number | Priority date | Publication date | Assignee | Title |
|---|---|---|---|---|
| US3547842A (en) * | 1969-08-05 | 1970-12-15 | American Cyanamid Co | Flame-retardant polyurethanes |
| EP2770001A1 (en) | 2009-07-18 | 2014-08-27 | Evonik Degussa GmbH | Use of tin salts of a carboxylic acid in the production of polyurethane systems |
| DE102009033710A1 (en) | 2009-07-18 | 2011-01-20 | Evonik Goldschmidt Gmbh | Use of metal salts of a carboxylic acid in the production of polyurethane systems |
| EP2289960A1 (en) | 2009-07-18 | 2011-03-02 | Evonik Goldschmidt GmbH | Use of metallic salts of a carboxylic acid in the production of polyurethane systems |
| DE102010003672A1 (en) | 2010-04-07 | 2011-10-13 | Evonik Goldschmidt Gmbh | Preparation and Use of Metal Salts of Alkyl Oxide and / or Aryl Alkoxylate Oligomers and Acid Terminated Polymers in the Preparation of Polyurethane Systems |
| WO2011124432A1 (en) | 2010-04-07 | 2011-10-13 | Evonik Goldschmidt Gmbh | Production and use of metal salts of alkyl oxide and/or aryl alkyl oxide oligomers and polymers with acid end groups in the production of polyurethane systems |
| US9096706B2 (en) | 2010-04-07 | 2015-08-04 | Evonik Degussa Gmbh | Production and use of metal salts of alkyl oxide and/or aryl alkyl oxide oligomers and polymers with acid end groups in the production of polyurethane systems |
| EP2557100A1 (en) | 2011-08-11 | 2013-02-13 | Evonik Goldschmidt GmbH | Compound containing tin and/or zinc salts of ricinoleic acid, urea and at least one other tin carboxylate and use of the compound in the production of polyurethane systems |
| DE102011110020A1 (en) | 2011-08-11 | 2013-02-14 | Evonik Goldschmidt Gmbh | Formulation containing tin and / or zinc salts of ricinoleic acid, urea, polyethylene glycol and sugar alcohol and use of the formulation in the preparation of polyurethane systems |
| DE102011110016A1 (en) | 2011-08-11 | 2013-02-14 | Evonik Goldschmidt Gmbh | Composition comprising tin and / or zinc salts of ricinoleic acid and at least one further tin carboxylate and use of the composition in the production of polyurethane systems |
| EP2557101A1 (en) | 2011-08-11 | 2013-02-13 | Evonik Goldschmidt GmbH | Formula containing tin and/or zinc salts of ricinoleic acid, urea, polyethylene glycol and sugar alcohol and use of the formula in the production of polyurethane systems |
| EP2752243A1 (en) | 2013-01-04 | 2014-07-09 | Evonik Industries AG | Use of tin salts of neodecanoic acid in the production of polyurethane systems |
| WO2014106642A1 (en) | 2013-01-04 | 2014-07-10 | Evonik Industries Ag | Use of tin salts of neodecanoic acid in the production of polyurethane systems |
| EP2762509A1 (en) | 2013-02-05 | 2014-08-06 | Evonik Industries AG | Composition for use in the production of polyurethane systems |
| DE102013201825A1 (en) | 2013-02-05 | 2014-08-07 | Evonik Industries Ag | Composition for use in the manufacture of polyurethane systems |
Also Published As
| Publication number | Publication date |
|---|---|
| NL302917A (en) | 1965-10-25 |
| DE1219672B (en) | 1966-06-23 |
| FR1379500A (en) | 1964-11-20 |
| BE642478A (en) | 1964-07-14 |
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