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US3957922A Expired / Lapsed US ⏱️ 0.0 years remaining

Process for preparing an oxyalkylated product and reaction product thereof

Assignee: BASF Corp
•
Filing: 1973-12-17
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Granted: 1976-05-18
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Expires: 1993-12-17
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Abstract

Abstract An oxyalkylated product useful for making polyurethane foams is prepared by reacting an alkylene oxide with a heated mixture of a phenol and a non-phenolic active hydrogen compound, at least one of which can be halogenated, in the presence of a catalyst complex of a phenol and an iron or aluminum substance. The mixture can also include a neutral phosphorus compound and/or acid anhydrides to enhance flame retardant properties. Optionally, also, the oxyalkylation reaction can be terminated by adding a tri (lower alkyl) amine and alkylene oxide to react with residual phenolic hydrogen in the mixture.

Inventors

  • 👤 Arthur L. Austin
  • 👤 William W. Levis, Jr.
  • 👤 Louis C. Pizzini
  • 👤 Robert J. Hartman

Bibliographic Details

Application Number —
Jurisdiction US
Data Source google_patents
Last Synchronized 2026-11-07 12:14
CPC Classifications
C; C07; C07F; C07F9/00; C07F9/02; C07F9/06; C07F9/08; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/40; C08G18/48; C08G18/50; C08G65/00; C08G65/02; C08G65/26; C08G65/2603; C08G65/2606; C08G65/2612; C08G65/2639

Claims Analysis

Total Claims: 23
Claim 1
Independent Claim 135 words
Process for preparing an oxyalkylated product which comprises 1. providing a reaction mixture containing a. a phenol, at least in an amount sufficient to form a complex with aluminum or iron substances in the mixture, b. a non-phenolic active hydrogen compound having from 1 to 8 active hydrogens per molecule and having an average molecular weight below about 10,000, and c. aluminum or iron in a form which will complex with the phenol a), in an amount sufficient to form a complex with the phenol a), d. a trivalent phosphorus neutral ester flame retardant, 2. heating the mixture to a temperature in the range of about 80°C. to about 250°C., and 3. oxyalkylating the heated mixture by adding thereto sufficient alkylene oxide having from 2 to 12 carbon atoms to form an oxyalkylated polyol product.
Claim 2
Dependent Claim 135 words
Process for preparing an oxyalkylated product which comprises 1. providing a reaction mixture containing a. a phenol, at least in an amount sufficient to form a complex with aluminum or iron substances in the mixture, b. a non-phenolic active hydrogen compound having from 1 to 8 active hydrogens per molecule and having an average molecular weight below about 10,000, and c. aluminum or iron in a form which will complex with the phenol a), in an amount sufficient to form a complex with the phenol a), d. a trivalent phosphorus neutral ester flame retardant, 2. heating the mixture to a temperature in the range of about 80°C. to about 250°C., and 3. oxyalkylating the heated mixture by adding thereto sufficient alkylene oxide having from 2 to 12 carbon atoms to form an oxyalkylated polyol product.
Claim 3
Dependent Claim 19 words
Process of claim 1 wherein at least one of the compounds (a) and (b) in the mixture is halogenated.
Claim 4
Dependent Claim 27 words
Process of claim 1 wherein the aluminum or iron (c) is present in the mixture in a concentration of from about 50 to 20,000 parts per million.
Claim 5
Dependent Claim 33 words
Process of claim 1 wherein the phenol (a) to active hydrogen compound (b) reactive equivalent ratio in the mixture is from about 4:1 to about 0.1 to 1 of phenolic hydrogen: active hydrogen.
Claim 6
Dependent Claim 19 words
Process of claim 1 wherein the aluminum or iron (c) is a mixture of aluminum chloride and iron chloride.
Claim 7
Dependent Claim 19 words
Process of claim 1 wherein the oxyalkylation is carried out in an inert atmosphere and at an elevated pressure.
Claim 8
Dependent Claim 84 words
Process of claim 1 which further includes the step of terminating the oxyalkylation of the mixture by adding to the mixture a tri (lower alkyl) amine having from 1 to 4 carbon atoms in each alkyl group in an amount which is at most approximately equivalent to the original phenol content of the mixture but which is sufficient in amount to promote oxyalkylation of any un-oxyalkylated phenol in the mixture, and additional alkylene oxide until no more alkylene oxide will react in the mixture.
Claim 9
Dependent Claim 172 words
Process of claim 1 which comprises 1. providing a mixture containing a. a phenol, b. an active hydrogen compound selected from the group consisting of polyhydroxy compounds containing from 2 to 8 active hydrogens per molecule, and mixtures thereof, in a reactive equivalent ratio of phenolic hydrogen to active hydrogen of from about 4:1 to about 0.1:1 at least one of said phenolic compound (a) and said active hydrogen compound (b) being halogenated, and c. a compound selected from the group consisting of aluminum and iron chlorides and mixtures thereof, said compound of aluminum or iron or mixture thereof being present in the mixture in a concentration of from 250 to about 2500 parts per million, and d. phosphorus ester flame retardant; 2. heating the mixture to a temperature in the range of from about 125°C. to about 175°C., and 3. oxyalkylating the heated mixture by adding an alkylene oxide selected from the group consisting of ethylene oxide, propylene oxide, epichlorohydrin and mixtures thereof to the mixture, to form an oxyalkylated polyol.
Claim 10
Dependent Claim 113 words
Process of claim 8 wherein (d) is a trivalent phosphorus ester having a formula selected from the group consisting of ##EQU6## wherein each of R 1 , R 2 and R 3 is a hydrocarbon radical free of aliphatic unsaturation containing from 1 to 8 carbon atoms, or such a hydrocarbon radical containing halogen substitution therein, and ##EQU7## wherein each of R 4 and R 5 is a hydrocarbon radical free of aliphatic unsaturation and containing from 1 to 8 carbon atoms or such a hydrocarbon radical containing halogen substitution, in an amount of said phosphorus ester to provide from about 1 to 5 percent by weight of phosphorus in the oxyalkylated product.
Claim 11
Dependent Claim 45 words
Process of claim 1 wherein a heated mixture containing (a) pentachlorophenol, (b) pentaerythritol, (c) a compound selected from the group consisting of an aluminum compound, an iron compound, and mixtures thereof, and (d) phosphorus ester is treated with propylene oxide to form an oxyalkylation product.
Claim 12
Dependent Claim 51 words
A process of claim 10 wherein (d) is a phosphorus ester compound of the formula ##EQU8## wherein each of R 1 , R 2 and R 3 is a hydrocarbon radical free of aliphatic unsaturation containing from 1 to 8 carbon atoms, or such a hydrocarbon radical containing halogen substitution therein.
Claim 13
Dependent Claim 13 words
A process of claim 11 wherein the phosphorus ester compound (d) is triphenylphosphite.
Claim 14
Dependent Claim 70 words
Process of claim 1 wherein a heated mixture containing (a) a phenol (b) an active hydrogen compound and (e) an organic acid anhydride, at least one of which components (a), (b) and (e) is halogenated, and (c) a compound selected from the group consisting of an aluminum compound, an iron compound and mixtures thereof, and (d) phosphorus ester flame retardant, is treated with propylene oxide to form an oxyalkylation product.
Claim 15
Dependent Claim 36 words
Process of claim 13 wherein each of the phenol (a) and the active hydrogen compound (b) and the organic acid anhydride (e) is halogenated, and wherein the (e) is the anhydride of an organic polycarboxylic acid.
Claim 16
Dependent Claim 64 words
Process of claim 1 wherein a heated mixture containing (a) a phenol (b) a polyhydric alcohol having from 3 to about 8 hydroxyl groups and a molecular weight below about 350 and (c) a compound selected from the group consisting of aluminum chloride, ferric chloride and mixtures thereof, and (d) phosphorus ester flame retardant is treated with propylene oxide to form an oxyalkylation product.
Claim 17
Dependent Claim 52 words
Process of claim 15 wherein the mixture which is treated with propylene oxide comprises a halogenated phenol containing between about 250 and 800 parts per million of a mixture of an aluminum chloride or an iron chloride, and a polyhydric alcohol selected from the group consisting of glycerine, pentaerythritol, sucrose and sorbitol.
Claim 18
Dependent Claim 84 words
Process of claim 8 which further includes the step of terminating the oxyalkylation of the mixture by adding to the mixture a tri (lower alkyl) amine having from 1 to 4 carbon atoms in each alkyl group in an amount which is at most approximately equivalent to the original phenol content of the mixture but which is sufficient in amount to promote oxyalkylation of any un-oxyalkylated phenol in the mixture, and additional alkylene oxide until no more alkylene oxide will react in the mixture.
Claim 19
Dependent Claim 84 words
Process of claim 10 which further includes the step of terminating the oxyalkylation of the mixture by adding to the mixture a tri (lower alkyl) amine having from 1 to 4 carbon atoms in each alkyl group in an amount which is at most approximately equivalent to the original phenol content of the mixture but which is sufficient in amount to promote oxyalkylation of any un-oxyalkylated phenol in the mixture, and additional alkylene oxide until no more alkylene oxide will react in the mixture.
Claim 20
Dependent Claim 84 words
Process of claim 18 which further includes the step of terminating the oxyalkylation of the mixture by adding to the mixture a tri (lower alkyl) amine having from 1 to 4 carbon atoms in each alkyl group on an amount which is at most approximately equivalent to the original phenol content of the mixture but which is sufficient in amount to promote oxyalkylation of any un-oxyalkylated phenol in the mixture, and additional alkylene oxide until no more alkylene oxide will react in the mixture.
Claim 21
Dependent Claim 136 words
An oxyalkylation polyol product prepared by the process of 1. providing a reaction mixture containing a. a phenol, at least in an amount sufficient to form a complex with aluminum or iron substances in the mixture, b. a non-phenolic active hydrogen compound having from 1 to 8 active hydrogens per molecule and having an average molecular weight below about 10,000, and c. aluminum or iron in a form which will complex with the phenol (a), in an amount sufficient to form a complex with the phenol (a), d. a trivalent phosphorus neutral ester flame retardant, 2. heating the mixture to a temperature in the range of about 80°C. to about 250°C., and 3. oxyalkylating the heated mixture by adding thereto sufficient alkylene oxide having from 2 to 12 carbon atoms to form an oxyalkylated polyol product.
Claim 22
Dependent Claim 136 words
An oxyalkylation polyol product prepared by the process of 1. providing a reaction mixture containing a. a phenol, at least in an amount sufficient to form a complex with aluminum or iron substances in the mixture, b. a non-phenolic active hydrogen compound having from 1 to 8 active hydrogens per molecule and having an average molecular weight below about 10,000, and c. aluminum or iron in a form which will complex with the phenol (a), in an amount sufficient to form a complex with the phenol (a), d. a trivalent phosphorus neutral ester flame retardant, 2. heating the mixture to a temperature in the range of about 80°C. to about 250°C., and 3. oxyalkylating the heated mixture by adding thereto sufficient alkylene oxide having from 2 to 12 carbon atoms to form an oxyalkylated polyol product.
Claim 23
Dependent Claim 23 words
An oxyalkylation polyol product of claim 20 wherein at least one of the compounds (a) and (b) in the reaction mixture is halogenated.

References Cited (Backward Citations)

US3472919A Cited
US3758646A Cited

USPTO Annuity & Maintenance Windows

Annuity Stage Window Opens Payment Deadline Surcharge Period Until Estimated Fee Status
3.5 Years (Year 4) 1979-05-18 1979-11-17 1980-05-18 $2000.00 Window Closed / Lapsed
7.5 Years (Year 8) 1983-05-18 1983-11-17 1984-05-18 $3760.00 Window Closed / Lapsed
11.5 Years (Year 12) 1987-05-18 1987-11-17 1988-05-18 $7700.00 Window Closed / Lapsed

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