US4621104A
Expired / Lapsed
US
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Process for the production of liquid bromine-containing alkoxylation products
Assignee: Bayer AG
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Filing: 1985-10-09
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Granted: 1986-11-04
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Expires: 2005-10-09
Abstract
Abstract Liquid bromine-containing alkoxylation products of butyne-(1,4)-diol which are storage stable are produced. More specifically, 1.5 to 2.5 mols alkylene oxide are reacted with each mol of butyne-(1,4)-diol present at elevated temperature in the presence of a catalyst. The catalyst is selected from (1) thioethers having a molecular weight of up to 5000 obtained by adding a mercaptan and/or mercaptoalcohol to an unsaturated hydrocarbon and/or (2) thioethers other than those of (1) having a molecular weight of from 500 to 5000 and/or (3) alkali metal chlorides. This alkoxylation product is then reacted with bromine at -10° to 80° C. The bromide is reoxidized with aqueous hydrogen peroxide solution, stabilized with a relatively non-volatile epoxide and dehydrated. The product thus obtained is particularly useful in the production of flame resistant isocyanate addition products such as polyurethane foams.
Inventors
- 👤 Manfred Dietrich
- 👤 Manfred Schmidt
- 👤 Rolf Wiedermann
- 👤 Klaus Konig
Bibliographic Details
Application Number
—
Jurisdiction
US
Data Source
google_patents
Last Synchronized
2026-10-23 15:07
CPC Classifications
C; C07; C07C; C07C41/00; C07C41/01; C07C41/02; C07C41/03; C07C41/18; C07C41/22; C08; C08G; C08G18/00; C08G18/06; C08G18/28; C08G18/30; C08G18/38; C08G18/3802; C08G18/3804; C08G18/3806; C08G18/381; C08G18/67; C08G18/675; C08G18/677; C08G18/6775; C08G2115/00; C08G2115/02
Claims Analysis
Total Claims: 19
Claim 1
Independent Claim
155 words
A process for the production of liquid bromine-containing alkoxylation products of butyne-(1,4)-diol which are storage stable comprising: (a) reacting each mol of butyne-(1,4)-diol with from 1.5 to 2.5 mols alkylene oxide at elevated temperature in the presence of a catalyst selected from (1) thioethers having a molecular weight of up to 5000 obtained by adding a mercaptan and/or mercaptoalcohol to an unsaturated hydrocarbon and/or (2) thioethers other than those of (1) having a molecular weight of from 500 to 5,000 and/or (3) alkali metal chlorides to form an alkoxylation product, (b) reacting the alkoxylation product of (a) with 0.6 to 1.9 mols of bromine for each mol of butyne-(1,4)-diol used in (a) at a temperature of from -10° to 80° C. to form a bromide, (c) reoxidizing the bromide of (b) with aqueous hydrogen peroxide solution, (d) stabilizing the bromide with from 0.3 to 3 wt. % relatively non-volatile epoxide and (e) dehydrating the bromide.
Claim 2
Dependent Claim
155 words
A process for the production of liquid bromine-containing alkoxylation products of butyne-(1,4)-diol which are storage stable comprising: (a) reacting each mol of butyne-(1,4)-diol with from 1.5 to 2.5 mols alkylene oxide at elevated temperature in the presence of a catalyst selected from (1) thioethers having a molecular weight of up to 5000 obtained by adding a mercaptan and/or mercaptoalcohol to an unsaturated hydrocarbon and/or (2) thioethers other than those of (1) having a molecular weight of from 500 to 5,000 and/or (3) alkali metal chlorides to form an alkoxylation product, (b) reacting the alkoxylation product of (a) with 0.6 to 1.9 mols of bromine for each mol of butyne-(1,4)-diol used in (a) at a temperature of from -10° to 80° C. to form a bromide, (c) reoxidizing the bromide of (b) with aqueous hydrogen peroxide solution, (d) stabilizing the bromide with from 0.3 to 3 wt. % relatively non-volatile epoxide and (e) dehydrating the bromide.
Claim 3
Dependent Claim
17 words
The process of claim 1 in which the thioether (2) is the acidic condensation product of thiodiglycol.
Claim 4
Dependent Claim
22 words
The process of claim 1 in which the reaction (b) is carried out at a temperature of from 0° to 40° C.
Claim 5
Dependent Claim
28 words
The process of claim 1 in which from 0.98 to 1.02 mols of bromine are used in reaction (b) for each mol of butyne-(1,4)-diol used in reaction (a).
Claim 6
Dependent Claim
22 words
The process of claim 1 in which the dehydration (e) is carried out after reoxidation (c) and before the stabilization of (d).
Claim 7
Dependent Claim
18 words
The process of claim 1 in which the dehydration (e) is carried out after the stabilization of (d).
Claim 8
Dependent Claim
19 words
The process of claim 1 in which the thioether of (a)(1) is the addition product of mercaptoethanol and limonene.
Claim 9
Dependent Claim
21 words
The process of claim 1 in which the thioether of (a)(2) is the condensation product of concentrated phosphoric acid and thiodiglycol.
Claim 10
Dependent Claim
27 words
The process of claim 1 in which from 1.98 to 2.05 mols of ethylene oxide and/or propylene oxide are reacted with each mol of butyne-(1,4)-diol in (a).
Claim 11
Dependent Claim
24 words
The process of claim 1 in which the reoxidation (c) is carried out using an equivalent amount or a slight excess of hydrogen peroxide.
Claim 12
Dependent Claim
22 words
The process of claim 1 in which the reoxidation (c) is carried out at a temperature of from 0° to 40° C.
Claim 13
Dependent Claim
21 words
The process of claim 1 in which the epoxide used in the stabilization (d) has a molecular weight greater than 174.
Claim 14
Dependent Claim
53 words
A process for the production of polyisocyanate-based flame-resistant plastics comprising reacting (a) an organic polyisocyanate with (b) a relatively high molecular weight compound having isocyanate-reactive hydrogen atoms in which from 1 to 60 wt. % of the isocyanate-reactive compound (b) is a liquid bromine-containing alkoxylation product produced by the process of claim 1.
Claim 15
Dependent Claim
23 words
The process of claim 13 in which from 40 to 99 wt. % of the isocyanate reactive compound (b) is a polyhydroxyl compound.
Claim 16
Dependent Claim
31 words
The process of claim 13 in which from 3 to 50 wt. % of the isocyanate-reactive compound (b) is a liquid bromine-containing alkoxylation product produced by the process of claim 1.
Claim 17
Dependent Claim
26 words
The process of claim 15 in which the reactants are employed in quantities such that an NCO characteristic number of from 100 to 135 is obtained.
Claim 18
Dependent Claim
26 words
The process of claim 15 in which the reactants are employed in quantities such that an NCO characteristic number of from 135 to 500 is obtained.
Claim 19
Dependent Claim
23 words
The process of claim 13 in which the reaction mixture further includes from 3 to 25 wt. % phosphorus- and/or halogen-containing flame-proofing agent.
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USPTO Annuity & Maintenance Windows
| Annuity Stage | Window Opens | Payment Deadline | Surcharge Period Until | Estimated Fee | Status |
|---|---|---|---|---|---|
| 3.5 Years (Year 4) | 1989-11-03 | 1990-05-05 | 1990-11-04 | $2000.00 | Window Closed / Lapsed |
| 7.5 Years (Year 8) | 1993-11-03 | 1994-05-05 | 1994-11-04 | $3760.00 | Window Closed / Lapsed |
| 11.5 Years (Year 12) | 1997-11-03 | 1998-05-05 | 1998-11-04 | $7700.00 | Window Closed / Lapsed |