USRE30676E - Flame resistant polyurethane foam and process for producing the same - Google Patents

Flame resistant polyurethane foam and process for producing the same Download PDF

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Publication number
USRE30676E
USRE30676E US06/110,501 US11050180A USRE30676E US RE30676 E USRE30676 E US RE30676E US 11050180 A US11050180 A US 11050180A US RE30676 E USRE30676 E US RE30676E
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group
hydrogen atom
organic group
groups
divalent
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US06/110,501
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Shigeo Mori
Takeshi Fujita
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DKS Co Ltd
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Dai Ichi Kogyo Seiyaku Co Ltd
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Priority claimed from JP48072463A external-priority patent/JPS5215118B2/ja
Priority claimed from JP48110799A external-priority patent/JPS5215119B2/ja
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    • 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
    • C08G18/16—Catalysts
    • C08G18/18—Catalysts containing secondary or tertiary amines or salts thereof
    • 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
    • C08G18/30—Low-molecular-weight compounds
    • C08G18/38—Low-molecular-weight compounds having heteroatoms other than oxygen
    • C08G18/3819—Low-molecular-weight compounds having heteroatoms other than oxygen having nitrogen
    • 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
    • C08G18/65—Low-molecular-weight compounds having active hydrogen with high-molecular-weight compounds having active hydrogen
    • C08G18/66—Compounds of groups C08G18/42, C08G18/48, or C08G18/52
    • 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
    • C08G18/675—Low-molecular-weight compounds

Definitions

  • the present invention relates to a process of producing a rigid polyurethane foam having flame resistance and more particularly, it relates to a process for producing a rigid polyurethane foam having a high flame resistance and unaccompanied by a reduction in the properties of the polyurethane foam or by the formation of scorching.
  • the invention further relates to a flame resistant rigid polyurethane produced by such a process.
  • the term "rigid polyurethane foam” used herein refers to a foam which loses its original rigidity when the foam is compressed to a compression ratio more than 50% due to the rupture of cells.
  • the rigidity of a given foam is generally indicated by a rigidity at a 10% compression ratio.
  • Polyurethane foams have hitherto been used in a large number of fields due to their specific properties but have a serious disadvantage in that polyurethane foams are easily flammable.
  • Japanese Pat. Publn Nos. 1750/'63; 9197/'70; etc. disclose the use of phosphorus-containing compounds or halogen-containing compounds as flame retarders for polyurethane foams but, in such known techniques the phosphorus-containing compound must be added to such an extent that the content of phosphorus in the foam is higher than 1% or the flame retarder must be blended so that the content thereof is 5 to 30% by weight of the polyurethane foam.
  • the properties of the polyurethane foam are degraded, for example, the hardness is reduced, the strength is reduced, etc.
  • the extent of the reduction of the amount of retarder depends upon the extent of flame resistance required in the polyurethane foam and the properties of the flame retarder used, but it is preferred that the amount be as small as possible and further it is most preferred that a flame retarder not be used at all.
  • rigid polyurethane foam having excellent flame resistance with less reduction in the desired properties thereof can be produced using a greatly reduced amount of a flame retarder or without using any flame retarder by blending the raw materials for producing the polyurethane with a specific amine compound.
  • a process of producing a flame resistant rigid polyurethane foam comprises reacting a mixture of a polyetherpolyol and/or a polyesterpolyol having an active hydrogen atom, a polyisocyanate, water and/or a volatile foaming agent as a foaming agent, and an emulsifying agent and containing in the reaction system at least one amine compound represented by any one of the following general formulae (I), (II), (III), (IV), (V), (VI), and (VII): ##STR1## wherein A 1 , A 2 , A 3 , A 4 , and A 5 each represents a hydrogen atom or a monovalent organic group, wherein at least one of A 1 to A 5 being a hydrogen atom or an organic group which contains a hydrogen atom active to an isocyanate group; R 1 is a divalent organic group, a trivalent organic group or a tetravalent organic group; R 2 represents a divalent organic group; m
  • a flame resistant rigid polyurethane foam produced by the aforesaid process is provided.
  • the process of this invention it becomes possible to produce a rigid polyurethane foam having high flame-resisting properties unaccompanied by the occurrence of scorching due to decreasing the amount of flame retarder to such an extent that has been considered to be impossible to provide flame resisting properties using conventional techniques.
  • a feature common to the amine compounds represented by aforesaid general formulae (I)-(VII) is that they contain a hydrogen atom active to an isocyanate group.
  • a feature of the present invention lies in the discovery that by adding the aforesaid amine compound to the reaction system used in the production of polyurethane foam, the amine compound is introduced in the molecular structure of the polyurethane foam and in this case by properly controlling the reaction of the active hydrogen atom in the amine compound with the isocyanate group, the polymer chain of the foam has excellent flame-resisting properties.
  • control of the reaction between such an active hydrogen atom and an isocyanate group in this invention can be attained by permitting nitrogen atoms to exist in the same molecule relative to the active hydrogen atom. That is, it is believed that the reaction is controlled favorably by a catalytic activity of the lone electron pair (the electron pair which does not contribute to the covalent bond) of the nitrogen atom present in the same molecule.
  • Examples of monovalent groups represented by A 1 to A 5 include saturated or unsaturated alkyl groups, aryl groups, alicyclic groups and substituted alkyl, aryl and alicyclic groups.
  • the number of carbon atoms of the alkyl group can range from 1 to 22 and the number of carbon atoms forming the ring of the alicyclic group can range from about 3 to 6.
  • suitable substituents are an amino group, a hydroxyl group, a cyano group, a halogen atom, a mercapto group and the like.
  • organic groups represented by A 1 to A 5 are organic groups including ##STR8## groupings in their structure. Suitable such groups are, for example, ##STR9## wherein R represents a saturated or unsaturated lower alkyl group or an aryl group and R' represents a saturated or unsaturated lower alkylene group having, preferably, 1 to 22 carbon atoms.
  • Suitable examples of the organic groups of A 1 to A 5 are ##STR10## and the like.
  • Examples of the divalent organic group represented by R 1 and R 2 in the general formula (I) are a saturated or unsaturated alkylene group, an arylene group, a divalent alicyclic group, and substituted groups of these groups, the alkylene group having about 1 to 22 carbon atoms and the number of carbon atoms forming the ring of the alicyclic group being about 3 to 6.
  • Specific examples of suitable divalent organic groups are as follows: ##STR11## wherein R 9 and R 10 each represents a hydrogen atom or a lower alkyl group having, preferably, 1 to 8 carbon atoms, and R 11 represents an alkylene group having, preferably, 1 to 22 carbon atoms.
  • the above illustrated groups may also be partially or fully hydrogenated.
  • Suitable examples of R 9 and R 10 are a hydrogen atom and a methyl group, and suitable examples of R 11 are --CH 2 -- or --C 4 H 8 --.
  • specific examples of the divalent organic groups are organic groups having at least one of --O--, ##STR12## and --S-- in the groups. For example, there are ##STR13##
  • Examples of the trivalent and tetravelent organic groups represented by R 1 in general formula (I) are a saturated or unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group, an alicyclic hydrocarbon group and a heterocyclic group.
  • examples of the divalent organic groups represented by R 3 , R 4 and R 5 are a saturated or unsaturated alkylene group, an arylene group, or a divalent alicyclic group.
  • the alkylene group has about 1 to 22 carbon atoms and the number of carbons forming the ring of the alicyclic group is about 3 to 6.
  • specific examples of these organic group are divalent organic groups containing ##STR75## groupings in the groups.
  • Examples of monovalent organic groups represented by A 6 , A 7 , and A 8 are the same as the monovalent organic group represented by A 1 to A 5 and described for the general formula (I).
  • the monovalent organic groups represented by A 9 , A 10 , A 11 and A 12 are the same as the monovalent organic groups represented by A 1 to A 5 and described for general formula (I).
  • the monovalent organic groups represented by A 13 and A 14 are the same as the monovalent organic groups represented by A 1 to A 5 and described for the general formula (I).
  • Examples of the divalent organic groups represented by R 6 and R 7 in the general formula (IV) are a saturated or unsaturated alkylene group, an arylene group, or a divalent alicyclic group.
  • the alkylene group has about 1 to 22 carbon atoms and the number of carbons forming the ring of the alicyclic group is about 3 to 6.
  • specific examples of these organic groups are divalent organic groups containing ##STR78## groupings in the groups.
  • Examples of monovalent organic groups represented by A 20 to A 22 in the general formula (VI) are the same as the monovalent organic groups represented by A 1 to A 5 and described for the formula (I).
  • Examples of monovalent organic groups represented by A 23 and A 24 in the general formula (VII) are the same as the monovalent organic groups represented by A 1 to A 5 and described for the formula (I).
  • Examples of organic groups represented by R 8 in the general formula (VII) are a monovalent, divalent, or trivalent saturated or unsaturated aliphatic hydrocarbon group, an aromatic hydrocarbon group, an alicyclic group, hydroxyl-substituted groups of these aliphatic, aromatic and alicyclic groups, and the aforesaid groups each substituted by a saturated or unsaturated alkyl group having about 1 to 10 carbon atoms or an aryl group.
  • the number of carbon atoms of the aliphatic hydrocarbon group ranges from about 1 to 22 and the number of carbons forming the ring of the alicyclic group ranges from about 3 to 6.
  • R 8 are ##STR82## wherein A 29 , A 30 , A 31 , A 32 , and A 33 each represents the same monovalent organic groups, represented by A 1 to A 5 and described for the formula (I) or a hydrogen atom.
  • R 8 , A 23 , and A 24 be a hydrogen atom or a group having a hydrogen atom active to an isocyanate group and examples of groups having an active hydrogen atom are a hydroxy-substituted alkyl group and an alkyl group substituted with an --SH group.
  • amine compound represented by general formula (I), (II), (III), (IV), (V), (VI) or (VII), individually in the production of polyurethane foam it is possible to render the polyurethane foam flame resistant, but more excellent flame-resisting effects can be obtained by using a combination of two kinds of any amine compounds.
  • a combination of an amine compound wherein at least one member of the monovalent groups A 1 to A 24 is a hydrogen atom and an amine compound wherein all the monovalent organic groups A 1 to A 24 are hydroxyl-containing groups or those having hydroxyl-containing groups and organic groups having no active hydrogen atom is especially preferred.
  • the polyurethane foam obtained using the aforesaid amine compounds without using a flame retarder is self-extinguishing with a burning distance of 14 to 22 mm as tested in accordance with ASTM D 1692-68.
  • the polyurethane foams thus prepared show self-extinguishing properties with a burning distance of 0 to 4 mm using the ASTM D 1692-68 test.
  • a flame retarder can be used in combination with the aforesaid amine compound or compounds although as is apparent from the above set forth results, the flame-resisting effects can be obtained without using such flame retarder.
  • Suitable flame retarders which can be used in this invention in such a case are phosphorus-containing compounds. Examples of these phosphorus-containing compounds are those compounds containing phosphorus only and which do not contain any halogen such as, for example, triphenyl phosphate, tricresyl phosphate, diethyl-N,N-bis(2-hydroxyethyl)aminomethyl phosphonate.
  • Vercol 82 (trade name, the structure of which is believed to be ##STR84## produced by Mobil Oil Co.), ammonium polyphosphate, bis(dipropylene glycol)dipropylene glycol phosphonate, tri(dipropylene glycol)phosphite, heptaquisdipropylene glycol triphosphite, trimethyl phosphate, triethyl phosphate, tributyl phosphate and trioctyl phosphate.
  • Compounds containing phosphorus and halogen can be also used as the flame retarder where desired and examples of such compounds are tri-2,3-dibromopropyl phosphate, trischloroethyl phosphate, trisdichloropropyl phosphate.
  • Phosgard 2XC-20 (trade name of Monsanto Chemical Co., for a product having the formula ##STR85## and monodichloropropylbis(dibromopropyl)phosphate.
  • Compounds containing phosphorus and halogen provide superior flame-resisting effects to the effects obtained with a compound containing phosphorus only and this is believed to be based on the synergistic effect of the phosphorus and halogen.
  • the above-described compounds can be used individually or in combination.
  • the aforesaid phosphorus-containing compound can be used together with an organo halogen compound such as tetrabromophthalic anhydride, tetrabromobisphenol A, tetrabromobutane, hexabromobenzene, dichloropropanol, and dibromopropanol.
  • the amount of the phosphorus-containing compound used in this invention can be much smaller than the amount employed using conventional technique and can be less than about 0.5% by weight to the weight of polyurethane foam.
  • the polyetherpolyol or the polyesterpolyol used in this invention can be free by selected to achieve the desired polyurethane foam. That is, as the polyetherpolyol or polyesterpolyol for rigid polyurethane foam, polyols having a hydroxyl value of about 150 to 900 mg KOH/g can be used individually or as a mixture thereof.
  • the polyetherpolyol used in this invention can be prepared by the addition polymerization reaction of an organic compound having at least two active hydrogen atoms and an alkylene oxide.
  • organic compounds having at least two hydrogen atoms which can be used as the raw material for producing the polyetherpolyol suitable for this invention are an alkylene glycol such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butane-2,3-diol, butane-1,3-diol, hexane-2,5-diol, octadecanediol, octadecenediol, cyclohexane-1,4-dimethanol, glycerine, trimethylolethane, trimethylolpropane, pentaerythritol, mannitol, sorbitol, and sucrose.
  • alkylene glycol such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butane-2,3-dio
  • alkylene oxides which can be used for the addition polymerization reaction are ethylene oxide, propylene oxide, butylene oxide, epichlorohydrin, and the like.
  • polyetherpolyol prepared by addition polymerizing the alkylene oxide and a mixture of two or more of the abovedescribed raw materials having at least two active hydrogen atoms and further it is also possible to use the polyetherpolyol prepared by random- or block-copolymerizing two or more alkylene oxides.
  • the polyesterpolyol used in this invention can be prepared by the polymerization reaction of a polyol having at least two active hydroxyl groups and a polybasic acid.
  • polyols examples are, as in the case of polyetherpolyols, an alkylene glycol such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butane-2,3-diol, butane-1,3-diol, hexane-2,5-diol, octadecanediol, octadecenediol, cyclohexane-1,4-dimethanol, glycerine, trimethylolethane, trimethylolpropane, pentaerythritol, mannitol, sorbitol, sucrose, etc.
  • alkylene glycol such as ethylene glycol, diethylene glycol, triethylene glycol, propylene glycol, dipropylene glycol, tripropylene glycol, butane-2,3-diol, butane-1,3-di
  • Suitable polybasic acids are adipic acid, succinic acid, suberic acid, sebacic acid, oxalic acid, methyladipic acid, glutaric acid, pimelic acid, azelaic acid, phthalic acid, terephthalic acid, isophthalic acid, 1,2,4-benzenetricarboxylic acid, thiodiglycolic acid, thiodipropionic acid, maleic acid, fumaric acid, citraconic acid, itaconic acid, trimellitic acid, a dimerized or trimerized fatty acid, tartaric acid, etc.
  • the polyisocyanate used in the present invention is a material conventionally used for producing polyurethane foams in the art and can be appropriately represented by the general formula
  • R 26 represents an aliphatic group, an aromatic group, a substituted aliphatic group, or a substituted aromatic group and n 3 has a mean value of 1.5 to 3.0.
  • R 26 represents an aliphatic group, an aromatic group, a substituted aliphatic group, or a substituted aromatic group and n 3 has a mean value of 1.5 to 3.0. Examples of the group R 26 are ##STR86##
  • Typical examples of the above-described polyisocyanate are ethylene diisocyanate, ethylidene diisocyanate, propylene diisocyanate, butylene diisocyanate, cyclopentylene-1,3-diisocyanate, cyclohexylene-1,4-diisocyanate, cyclohexylene-1,2-diisocyanate, 2,4-tolylene diisocyanate, 2,6-tolylene diisocyanate, 4,4'-diphenylmethane diisocyanate, 2,2-diphenylpropane-4,4'-diisocyanate, p-phenylene diisocyanate, m-phenylene diisocyanate, xylene diisocyanate, 1,4-naphthylene diisocyanate, xylene diisocyanate, 1,4-naphthylene diisocyanate, 1,5-naphthylene di
  • polyisocyanates Of the above-described polyisocyanates, the most widely used polyisocyanates are tolylene diisocyanate, crude polymethylenepolyphenylene isocyanate, crude tolylene diisocyanate, etc., and mixtures thereof.
  • the above isocyanate or a mixture of isocyanates can be used in an amount of from 0.5 to 3 equivalents, preferably from 1.0 to 2.0 equivalents, per 1 equivalent of the polyetherpolyol and/or polyesterpolyol.
  • catalysts can be used in this invention.
  • examples of catalysts are amine catalysts such as triethylamine, triethylenediamine, tetramethylethylenediamine, dimethylethanolamine, and the like and metal carboxylates as stannous octoate, dibutyltin dilaurate, lead octylate, and the like. That is, any catalysts which have been used conventionally for the production of polyurethane foams can be used in this invention.
  • a suitable amount of the catalyst is less than about 5% by weight, preferably 2 to 3% by weight, of the polyetherpolyol and/or polyesterpolyol. The lesser the amount of the catalyst, the better the results can be obtained.
  • foaming agents conventionally employed as the foaming agents for polyurethane foams can be used in this invention.
  • foaming agents are well-known and a few specific examples of these agents are monofluorotrichloromethane, methylene chloride, water, etc.
  • the amount of the foaming agent is suitably less than about 5% by weight, preferably less than 2% by weight, based on the total weight of the starting materials when water is employed as the foaming agent, and is less than about 70% by weight, preferably 10 to 60% by weight, when a volatile foaming agent is employed.
  • a silicone oil such as F-220, F-230, F-260, F-305 and F-307 (trademark of silicone oil, made by Shinetsu Chemical Industry Co.); L-520, L-5340 and L-5420 (trademark of silicone oil, made by Union Carbide Corp.); DC-190, DC-192, DC-193 and DC-195 (trademark of silicone oil, made by Dow Corning Co.); etc.
  • Such an emulsifying agent can be used in an amount less than about 2%, preferably less than 1.2% by weight based on the total weight of the starting materials for the polyurethane foams.
  • polyurethane foam can be prepared according to any of the above-described methods of can be prepared using other methods to achieve the objects of this invention.
  • the polyetherpolyols for rigid polyurethane foams as shown in Table 1 were prepared by addition-polymerizing propylene oxide to the starting materials shown in the same table.
  • the polyesterpolyol for rigid polyurethane foams as shown in Table 1 was prepared by condensation reaction of glycerine, adipic acid and ethylene glycol.
  • Rigid polyurethane foams were prepared using the amine compounds, the flame retarders, and the polyetherpolyols prepared as previously described.
  • the compositions for forming polyurethane foams, the foaming techniques, and the method of testing the flame resistance employed in this example were as follows:
  • the polyisocyanate the temperature of which had been adjusted to 20° C. was poured into the mixture and then the mixture was mixed for 10 seconds using a mixer at 4000 r.p.m.
  • the product thus obtained was poured into a plasticlined steel box.
  • foaming was completed in 150 seconds.
  • the foamed product was allowed to stand for 24 hours at room temperature (about 20° C. to 30° C.) and cut into pieces for measuring the various properties thereof. The results showed that all foams prepared had good appearance and were enclosed cellular type elastic foams.
  • the flame test was conducted according to the methods of American Standard of Testing Method D1692-68 (ASTM D1692-68) and the result was evaluated by the burning distance (mm) in each case.
  • the distance between the first marked line and the second marked line of the sample piece was 100 mm.
  • Rigid polyurethane foams were prepared using the amine compounds, the polyetherpolyols, and silicone oils previously described.
  • the compositions of the foaming materials, the foaming procedure, and the flame test employed in this example were as follows:
  • test results obtained are shown in TAble 4.
  • the amine compounds of this invention make it possible to provide a good flame-resisting property to the polyurethane foam without causing any deterioration of physical properties of the foam.
  • Rigid polyurethane foams were prepared using the combination of two kinds of the amine compounds and the polyetherpolyols previously described.
  • the composition of the foaming mixtures, the foaming procedures, and the flame resistance test employed in this example were as follows:
  • Rigid polyurethane foams were prepared using the polyetherpolyols, the silicone oils, and the combination of two kinds of the amine compounds, and the phosphorus-containing compounds as previously described.
  • the compositions of the foaming mixtures, the foaming procedure, and the flame test results were as follows:

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  • 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)
US06/110,501 1973-06-26 1980-01-08 Flame resistant polyurethane foam and process for producing the same Expired - Lifetime USRE30676E (en)

Applications Claiming Priority (4)

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JP48-72463 1973-06-26
JP48072463A JPS5215118B2 (it) 1973-06-26 1973-06-26
JP48-110799 1973-10-01
JP48110799A JPS5215119B2 (it) 1973-10-01 1973-10-01

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US48333974A Continuation 1973-06-26 1974-06-26
US05/645,172 Reissue US4088614A (en) 1973-06-26 1975-12-29 Flame resistant polyurethane foam and process for producing the same

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DE (1) DE2430589A1 (it)
FR (1) FR2235146B1 (it)
GB (1) GB1480392A (it)
IT (1) IT1016145B (it)
NL (1) NL7408510A (it)
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Cited By (3)

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US4722942A (en) 1986-05-30 1988-02-02 The Dow Chemical Company Flexible polyurethane foams which exhibit excellent flame resistance
US5336696A (en) * 1993-12-10 1994-08-09 Nisshinbo Industries, Inc. Halogen-free blowing agents that include cycloaliphatic hydrocarbons and are suitable for isocyanate-based polymeric foams
US5776992A (en) * 1995-11-03 1998-07-07 Hoechst Aktiengesellschaft Halogen-free, flame retardant rigid polyurethane foam

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US3948825A (en) * 1974-07-05 1976-04-06 Basf Wyandotte Corporation Curing agent for use in making cellular polyurethane compositions
DE2523633C2 (de) * 1975-05-28 1982-12-16 Bayer Ag, 5090 Leverkusen Verfahren zur Herstellung von Polyurethanschaumstoffen und Katalysatoren zur Durchführung des Verfahrens
CN115537171A (zh) * 2022-09-27 2022-12-30 江苏华大新材料有限公司 一种耐低温聚氨酯复合胶及其制备方法
CN116120199B (zh) * 2023-01-03 2025-05-27 华润水泥技术研发（广西）有限公司 一种多官能团的改性醇胺

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Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4722942A (en) 1986-05-30 1988-02-02 The Dow Chemical Company Flexible polyurethane foams which exhibit excellent flame resistance
US5336696A (en) * 1993-12-10 1994-08-09 Nisshinbo Industries, Inc. Halogen-free blowing agents that include cycloaliphatic hydrocarbons and are suitable for isocyanate-based polymeric foams
US5776992A (en) * 1995-11-03 1998-07-07 Hoechst Aktiengesellschaft Halogen-free, flame retardant rigid polyurethane foam

Also Published As

Publication number Publication date
GB1480392A (en) 1977-07-20
IT1016145B (it) 1977-05-30
FR2235146B1 (it) 1982-02-19
FR2235146A1 (it) 1975-01-24
NL7408510A (it) 1974-12-30
PH14717A (en) 1981-11-13
DE2430589A1 (de) 1975-01-16
AU7051274A (en) 1976-01-15

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