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EP0214722A1
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Brominated hydroxyaromatic compounds
Assignee: Dow Chemical Co
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Filing: 1986-07-07
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Granted: —
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Expires: 2006-07-07
Abstract
Abstract Novel ring-brominated derivatives of tetraalkyl dihydroxy diaromatic compounds, e.g. 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethyl-phenol) are prepared by contacting a tetraalkyl dihydroxydiaromatic compounds with a brominating agent in the presence of a reaction medium.Novel ring-brominated derivatives of the diepoxides of tetraalkyl dihydroxydiaromatic compounds, e.g., the diglycidyl ether of 3,5-dibromo-4-(2-(2-bromo-4-hydroxy-3,5-dimethylphenyl)-ethyl)-2,6-dimethylphenol are also prepared by contacting the aforementioned ring-brominated derivatives of tetraalkyl dihydroxydiaromatic compounds with haloalkylene oxide under reaction conditions.
Inventors
- 👤 Abel Mendoza
- 👤 Harry Craig Silvis
Bibliographic Details
Application Number
—
Jurisdiction
EP
Data Source
google_patents
Last Synchronized
2026-11-09 03:52
CPC Classifications
C; C07; C07C; C07C39/00; C07C39/12; C07C39/15; C07C39/16; C07C39/24; C07C39/367; C07D; C07D303/00; C07D303/02; C07D303/12; C07D303/18; C07D303/20; C07D303/24; C08; C08G; C08G59/00; C08G59/02; C08G59/04; C08G59/06; C08G59/063; C08G59/18; C08G59/20; C08G59/22; C08G59/30
Claims Analysis
Total Claims: 23
Claim 1
Independent Claim
82 words
A compound of the formula: characterized in that n is zero or a positive integer, each X independently is Br or H with proviso that when Y is hydrogen at least one X is H; Y is H or Z; each Z independently is a moiety having a terminal epoxide moiety, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms.
Claim 2
Dependent Claim
82 words
A compound of the formula: characterized in that n is zero or a positive integer, each X independently is Br or H with proviso that when Y is hydrogen at least one X is H; Y is H or Z; each Z independently is a moiety having a terminal epoxide moiety, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms.
Claim 3
Dependent Claim
67 words
A compound as claimed in Claim 1 of the formula: characterized in that n is zero or a positive integer, each X independently is Br or H with proviso that at least one X is H, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms.
Claim 4
Dependent Claim
69 words
A compound as claimed in Claim 1 of the formula: characterized in that n is zero or a positive integer, each X independently is bromine or hydrogen, each R a independently is hydrogen or alkyl of up to 12 carbon atoms, each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms, and each Z independently is a moiety having a terminal epoxide moiety.
Claim 5
Dependent Claim
46 words
A compound as claimed in Claim 3, wherein each R has up to 3 carbon atoms, and wherein each Z independently is a moiety of the formula: wherein each R b is hydrogen or an aliphatic or inertly-substituted aliphatic moiety of up to 25 carbon atoms.
Claim 6
Dependent Claim
13 words
A compound as claimed in Claim 4, wherein each R b is hydrogen.
Claim 7
Dependent Claim
20 words
A compound as claimed in any one of the preceding claims, wherein each R has up to 3 carbon atoms.
Claim 8
Dependent Claim
12 words
A compound as claimed in Claim 6, wherein each R is methyl.
Claim 9
Dependent Claim
15 words
A compound as claimed in any one of the preceding claims, wherein n is zero.
Claim 10
Dependent Claim
19 words
A compound as claimed in any one of the preceding claims, wherein at least one X moiety is Br.
Claim 11
Dependent Claim
21 words
A compound as claimed in any one of the preceding claims, wherein each R a has up to 6 carbon atoms.
Claim 12
Dependent Claim
14 words
A compound as claimed in Claim 1, selected from 4,4'-(1,2-ethanediyl)bis(3-bromo-2,6-dimethylphenol); 4,4'-(1,2-ethanediyl)bis(3,5-dibromo-2,6-dimethylphenol), and 3,5-dibromo-4-(2-(2-bromo-4-hydroxy-3,5-dimethylphenyl) ethyl)-2,6-dimethylphenol.
Claim 13
Dependent Claim
4 words
Diglycidyl ether of 3,5-dibromo-4-(2-(2-bromo-4-hydroxy-3,5-dimethylphenyl)ethyl)-2,6-dimethylphenol.
Claim 14
Dependent Claim
4 words
Diglycidyl ether of 3,5-dibromo-4-(2-(2-bromo-4-hydroxy-3,5-dimethylphenyl)ethyl)-2,6-dimethylphenol.
Claim 15
Dependent Claim
135 words
A process for the preparation of a compound as claimed in any one of the preceding claims, or an analogous compound of the Formula A of Claim 1 in which each X is bromine when Y is H, characterized in that a tetra-alkyl dihydroxydiaromatic polymethylene-bridged compound of the formula wherein n is zero or a positive integer, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms, or a partly ring brominated derivative thereof is contacted with a bromination agent to yield a compound of Formula A in which Y is H and, when a compound of Formula A in which Y is Z is required, reacting said brominated bisphenol with a haloalkylene oxide.
Claim 16
Dependent Claim
160 words
A process for the preparation of a compound of the formula wherein n is zero or a positive integer, each X independently is Br or H, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms, characterized in that (a) a tetraalkyl dihydroxydiaromatic polymethylene-bridged compound of the formula wherein n is zero or a positive integer, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms is contacted with a bromination agent in the presence of a reaction medium and, optionally, a brominated catalyst to form a reaction mixture; (b) the temperature of the reaction mixture is then raised to an elevated temperature until the reaction is completed; and (c) the resulting compound of Formula I is recovered.
Claim 17
Dependent Claim
160 words
A process for the preparation of a compound of the formula wherein n is zero or a positive integer, each X independently is Br or H, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms, characterized in that (a) a tetraalkyl dihydroxydiaromatic polymethylene-bridged compound of the formula wherein n is zero or a positive integer, each R a independently is H or alkyl of up to 12 carbon atoms, and each R independently is a primary or secondary alkyl moiety of up to 6 carbon atoms is contacted with a bromination agent in the presence of a reaction medium and, optionally, a brominated catalyst to form a reaction mixture; (b) the temperature of the reaction mixture is then raised to an elevated temperature until the reaction is completed; and (c) the resulting compound of Formula I is recovered.
Claim 18
Dependent Claim
16 words
A process as claimed in Claim 13 or Claim 14, wherein the brominating agent is bromine.
Claim 19
Dependent Claim
27 words
A process as claimed in any one of Claims 13 to 15, wherein the bromination is carried out using a halogenated lower alkane as a reaction medium.
Claim 20
Dependent Claim
32 words
A process as claimed in any one of Claims 13 to 16, wherein the bromination is carried out in the reaction medium at a temperature at which the reaction medium is liquid.
Claim 21
Dependent Claim
22 words
A process as claimed in any one of Claims 13 to 17, wherein the bromination reaction mixture is heated to reflux temperature.
Claim 22
Dependent Claim
32 words
A process as claimed in any one of Claims 13 to 18, wherein said compound of Formula III is 4,4'-(1,2-ethanediyl)bis(2,6-dimethylphenol), and the bromination is carried out in carbon tetrachloride or methylene chloride.
Claim 23
Dependent Claim
36 words
A composition comprising an adduct of: (a) an epoxy compound as claimed in any one of Claims 1, 3 to 10 or 12; (b) a curing agent for epoxy resins; and optionally, (c) a curing catalyst.
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