Modified arylhydroxy compounds for the production of polyurethane or polyisocyanurate
Esterified arylhydroxy compounds for the production of polyurethane or polyisocyanurate. In order to provide aromatic polyols for the production of polyurethanes or polyisocyanurates which are process-technically suitable in terms of their viscosity and at the same time give the end product good physical properties and a good reaction to fire, esterified arylhydroxy compounds are proposed as polyols.
1. A process for producing an esterified-alkoxylated-arylhydroxy-aldehyde-resin, comprising:
producing an arylhydroxy-aldehyde resin by reacting a reaction mixture of at least one arylhydroxy compound and at least one aldehyde in a molar ratio of from 1:0.25 to 1:0.85 in the presence of an acid, under reflux conditions having a temperature of 100° C. or more;
removing any free acid, water and residual monomer to a desired level;
charging a base catalyst to the reaction mixture at temperatures between 100° C. to 200° C.;
charging an alkoxylating agent to the reaction mixture wherein a ratio of phenolic hydroxyl groups to alkoxylating agent is 1:0.1 to 1:30 at temperatures of 100° C. to 200° C.;
neutralizing the cooled reaction mixture with inorganic or organic acid;
reacting the neutralized reaction mixture with a monocarboxylic or dicarboxylic acid or their anhydrides or carboxylic acid halides and holding the reaction at around 80° C. to 200° C. until the esterification reaction is complete; and
discharging the esterified-alkoxylated-arylhydroxy-aldehyde-resin.
2. The process of claim 1 wherein the arylhydroxy-aldehyde resin formation, its reaction with the alkoxylating agent and the subsequent esterification are carried out in the same reaction vessel or multiple reaction vessels.
3. The process of claim 1 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde-resin has a hydroxyl functionality ranging from 1 to 10.
4. The process of claim 1 , wherein a degree of alkoxylation of the arylhydroxy-aldehyde resin is from 30 to 100%.
5. The process of claim 1 , wherein the alkoxylating agent is ethylene oxide, propylene oxide, ethylene carbonate, propylene carbonate, butylene oxide, butylene carbonate or combinations thereof.
6. The process of claim 4 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde resin is an ethoxylated and/or propoxylated and/or a mixture of ethoxylated and propoxylated arylhydroxy-aldehyde resin.
7. The process of claim 1 , wherein the arylhydroxy compound is a phenol-formaldehyde resin.
8. The process of claim 1 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde-resin has a molar mass of from Mn 270 to 4000 g/mol.
9. The process of claim 1 , wherein the monocarboxylic acid is formic acid, acetic acid, benzoic acid, propionic acid, caprylic acid or mixtures thereof.
10. The process of claim 1 , wherein the dicarboxylic acid is selected from the group consisting of: adipic acid, succinic acid, maleic acid, fumaric acid, phthalic acid, isophthalic acid, terephthalic acid, and mixtures thereof.
11. The process of claim 1 , wherein the anhydride is selected from the group consisting of: acetic anhydride, succinic anhydride, phthalic anhydride, isophthalic anhydride, maleic anhydride, tetrahydrophthalic anhydride and mixtures thereof.
12. The process of claim 3 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde-resin has a hydroxyl functionality ranging from 1.5 to 2.5.
13. A process for producing an esterified-alkoxylated-arylhydroxy-aldehyde-resin, comprising:
reacting at least one arylhydroxy compound and at least one aldehyde in a molar ratio of from 1:0.25 to 1:0.85 in the presence of an acid, under reflux conditions;
removing any free acid, water and residual monomer to provide a first reaction product;
reacting the first reaction product with a base catalyst to provide a second reaction product;
adding at least one alkoxylating agent to the second reaction product to provide a third reaction product, wherein a ratio of phenolic hydroxyl groups to alkoxylating agent in the third reaction product is 1:0.1 to 1:30;
adding at least one inorganic or organic acid to neutralize the third reaction product; and
reacting the neutralized reaction product with a monocarboxylic or dicarboxylic acid or their anhydrides and/or one or more carboxylic acid halides to provide an esterified-alkoxylated-arylhydroxy-aldehyde-resin having a hydroxyl functionality of from 1 to 10.
14. The process of claim 13 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde-resin has a hydroxyl functionality of from 1.5 to 2.5.
15. The process of claim 13 wherein the arylhydroxy-aldehyde resin formation, its reaction with the alkoxylating agent and the subsequent esterification are carried out in the same reaction vessel.
16. The process of claim 13 , wherein the esterified-alkoxylated-arylhydroxy-aldehyde-resin has a molar mass of from Mn 270 to 4000 g/mol.