Patent GB-892173-A (GB)
Title: Hydroxypolyalkyleneoxyphenyl alkanes
IPC: C08G18/48
Filed: 1959-11-19
Abstract: Polyurethane foams are prepared by reacting poly-isocyanates with tris and tetrakis (hydroxyalkyleneoxyphenyl) alkanes of the general formula <FORM:0892173/IV (a)/1> in which R1 is a divalent saturated aliphatic hydrocarbon radical containing 1 to 10 carbon atoms, which may have a hydroxyl, nitro, chloro or bromo substituent, X is 0 or 1, R2 is a hydrogen atom or a hydroxy (polyalkleneoxy) phenyl radical, R3 is a hydrogen atom or a lower alkyl radical, R4 is an ethylene or propylene radical or a mixture thereof, n is a number having a value of at least one and may be equal to 100 or more, R6 is a hydrogen atom or an alkoxy, alkyl or cycloalkyl radical, and y is 1, 2 or 3. A wide variety of rigid, semi-rigid and flexible foams can be prepared in this manner; and these have good low-temperature properties compared with foams produced by isocyanate modification of dicarboxylic acid-triol polyesters.  For the preparation of the tris and tetrakis (hydroxypolyalkyleneoxyphenyl) alkanes by the reaction of ethylene oxide and/or propylene oxide with the appropriate tri- or tetra-phenylol-(see Group IV(b)).ALSO:Tris and tetrakis(hydroxyalkyleneoxyphenyl) alkanes of the general formula <FORM:0892173/IV (b)/1> in which R1 is a divalent saturated aliphatichydrocarbon radical containing 1 to 10 carbon atoms, which may have a hydroxyl, nitro, chloro or bromo substituent, X is 0 or 1, R2 is a hydrogen atom or a hydroxy (polyalkyleneoxy) phenyl radical, R3 is a hydrogen atom, or lower alkyl radical, R4 is an ethylene or propylene radical or a mixture thereof, n is a number having a value of at least one, R6 is a hydrogen atom or an alkoxy, alkyl or cycloalkyl radical, and Y is 1, 2 or 3, are prepared by the action of ethylene oxide and/or propylene oxide on the appropriate triphenylol or tetraphenylol in the presence of an alkaline catalyst.  In Example 1, three 1,1,3-tris (hydroxypolypropyleneoxyphenyl) propanes are prepared by reacting 1,1,3-tris (hydroxyphenyl) propane with propylene oxide so that 1, 3 and 4 moles of the latter, respectively, react with each mol of phenolic hydroxyl.  The reaction is carried out in the presence of sodium hydroxide, and at a temperature of 160 DEG C.-170 DEG C.  Example 3 describes the preparation of 1,1,2,2-tetrakis (hydroxypolyethyleneoxyphenyl) ethanes, containing an average of 3 ethyleneoxy groups per chain, by the action of ethylene oxide on 1,1,2,2-tetrakis (hydroxyphenyl) ethane.  Example 6 describes the preparation of 1,1,6,6-tetrakis (hydroxypolyethyleneoxyphenyl)-2-hydroxyhexanes, containing an average of 3.5 ethyleneoxy groups per chain, by reacting ethylene oxide with 1,1,6,6-tetrakis (hydroxyphenyl)-2-hydroxyhexane.  The starting materials for Examples 1, 3 and 6 are prepared by reacting phenol with acrolein, glyoxal and 2-hydroxyadipaldehyde, respectively, using concentrated hydrochloric acid as catalyst. Starting materials having hydroxyl and alkyl substituents in the benzene rings are specified; and it is stated that tris and tetrakis (hydroxyphenyl)-2-chloropropane, -2-nitropropane, and 2,3-dibromobutane may also be used as starting-materials.  The compounds of the invention have use in the preparation of polyurethane foams (see Group IV(a)).ALSO:Polyurethane foams are prepared by reacting polyisocyanates with tris-and tetrakis-(hydroxyalkyleneoxyphenyl) alkanes of the general formula:- <FORM:0892173/V/1> in which R1 is a divalent saturated aliphatic hydrocarbon radical containing 1 to 10 carbon atoms, which may have a hydroxyl, nitro, chloro or bromo substituent; x is 0 or 1; y is 1,2 or 3; n is a number having a value of at least one and may be 100 or more; R2 is a hydrogen atom or a hydroxy (polyalkyleneoxy) phenyl radical; R3 is a hydrogen atom or a lower alkyl radical; R4 is an ethylene or propylene radical or a mixture thereof; R6 is a hydrogen atom or an alkoxy, alkyl or cycloalkyl radical.  The preparation of the (hydroxyalkyeneoxy phenyl) alkanes is described.  (see Group IV(b)).