Flame-retardant phosphorus-functional polyether carbonate polyol and method for production thereof

Patent metadata

Field	Value
Publication number	US-11098154-B2
Application number	US-201816486029-A
Country	US
Kind code	B2
Filing date	Apr 3, 2018
Priority date	Apr 5, 2017
Publication date	Aug 24, 2021
Grant date	Aug 24, 2021

Abstract

A process for preparing a phosphorus-functional polyethercarbonate polyol, comprising reacting a polyethercarbonate polyol having unsaturated groups with a phosphorus-functional compound of formula (Ia):wherein X=O or S; and wherein R1 and R2 are selected from the group consisting of C1-C22 alkyl, C1-C22 alkoxy, C1-C22 alkylsulfanyl, C6-C70 aryl, C6-C70 aryloxy, C6-C70 arylsulfanyl, C7-C70 aralkyl, C7-C70 aralkyloxy, C7-C70 aralkylsulfanyl, C7-C70 alkylaryl, C7-C70 alkylaryloxy, C7-C70 alkylarylsulfanyl, or wherein R1 and R2 are bridged to one another directly and/or via heteroatoms and are selected from the group consisting of C1-C22 alkylene, oxygen, sulfur, and NR5, wherein R5 is hydrogen, C1-C22 alkyl, C1-C22 acyl, C7-C22 aralkyl, or C6-C70 aryl radical. A process for preparing a phosphorus-functional polyurethane polymer is disclosed. Phosphorus-functional polyethercarbonate polyol, phosphorus-functional polyurethane polymer, flame-retardant adhesion promoter, filler-activator, flame retardant, flame-retardant coating, foam, sealing compound, thermoplastic, thermoset, rubber, and a moulded body are disclosed.

First claim

What is claimed is:

1. A process for preparing a phosphorus-functional polyethercarbonate polyol, comprising reacting a polyethercarbonate polyol having unsaturated groups with a phosphorus-functional compound of formula (Ia):

wherein X=O or S;
and wherein R 1 and R 2 are selected from the group consisting of C1-C22 alkyl, C1-C22 alkoxy, C1-C22 alkylsulfanyl, C6-C70 aryl, C6-C70 aryloxy, C6-C70 arylsulfanyl, C7-C70 aralkyl, C7-C70 aralkyloxy, C7-C70 aralkylsulfanyl, C7-C70 alkylaryl, C7-C70 alkylaryloxy, C7-C70 alkylarylsulfanyl, or
wherein R 1 and R 2 are bridged to one another directly and/or via heteroatoms and are selected from the group consisting of C1-C22 alkylene, oxygen, sulfur, and NR 5 ,
wherein R 5 is hydrogen, C1-C22 alkyl, C1-C22 acyl, C7-C22 aralkyl, or C6-C70 aryl radical.

2. The process as claimed in claim 1 , wherein the phosphorus-functional compound of the formula (Ia) is a compound of the formula (Ib)

wherein A, and C are independently selected from the group consisting of a chemical bond, O, NH, N—(C1-C10 alkyl), and N—(C6-C14 aryl),
wherein R 3 and R 4 are independently selected from the group consisting of C1-C10 alkyl, C1-C10 alkoxy, C6-C14 aryl, C6-C14 aryloxy, and C9-C17 aralkyl, and
wherein n and m are independently 0, 1, 2, 3 or 4.

3. The process as claimed in claim 2 ,
wherein R 3 and R 4 are selected from the group consisting of C1-C8 alkyl and C1-C8 alkoxy, and
wherein n and m are independently 0 or 1.

4. The process as claimed in claim 1 , wherein the phosphorus-functional compound is 9,10-dihydro-9-oxa-10-phosphaphenanthrene 10-oxide and/or butyl P-methylphosphinate.

5. The process as claimed in claim 1 , wherein the polyethercarbonate polyol having unsaturated groups is selected from polyethercarbonate polyols having unsaturated groups or polyetherestercarbonate polyols having unsaturated groups.

6. The process as claimed in claim 1 , wherein the polyethercarbonate polyol having unsaturated groups has been obtained by reacting a starter compound with one or more alkylene oxides, carbon dioxide, and one or more further monomers selected from the group of the alkylene oxides, the cyclic anhydrides of dicarboxylic acids, the lactones, lactides, and cyclic 6-membered carbonates, with the proviso that at least one of the further monomers used contains one or more C—C double or triple bonds.

7. The process as claimed in claim 1 , wherein a phosphorus content of the phosphorus-functional polyethercarbonate polyols is between 0.5% and 15% by weight.

8. The process as claimed in claim 1 , wherein the polyethercarbonate polyol having unsaturated groups has been prepared by a process comprising the following steps:
(α) initially charging an H-functional starter compound and a DMC catalyst,
(β) optionally metering in an epoxide,
(γ) metering in
(γ1) at least one epoxide, and
(γ2) at least one epoxide, a cyclic anhydride of a dicarboxylic acid, a lactone, a lactide and/or a cyclic 6-membered carbonate having a double bond, and
(γ3) carbon dioxide.

9. The process as claimed in claim 1 , wherein the polyethercarbonate polyol having unsaturated groups is reacted with the phosphorus-functional compound of formula (Ia) at a temperature of not less than 100° C. and not more than 220° C.

10. The process as claimed in claim 1 , wherein the polyethercarbonate polyol having unsaturated groups is reacted with the phosphorus-functional compound of formula (Ia) at a temperature of not less than 0° C. and not more than 100° C. and, in the reaction,
a compound selected from the group of the basic catalysts or
a compound selected from the group of the photoinitiators, peroxides, azo compounds, metal-activated peroxides and/or redox initiators is added.

11. A phosphorus-functional polyethercarbonate polyol obtainable by the process as claimed in claim 1 .

12. A process for preparing a phosphorus-functional polyurethane polymer, wherein at least one phosphorus-functional polyethercarbonate polyol as claimed in claim 11 is reacted with one or more di- or polyisocyanates.

13. A phosphorus-functional polyurethane polymer obtainable by a process as claimed in claim 12 .

14. A product comprising the phosphorus-functional polyethercarbonate polyol as claimed in claim 11 , the product selected from the group consisting of a flame-retardant adhesion promoter, a filler-activator, a flame retardant, flame-retardant coating, a foam, a sealing compound, a thermoplastic, a thermoset, or a rubber.

15. A moulded body having a flame-retardant layer comprising a phosphorus-functional polyurethane polymer as claimed in claim 13 .

16. A product comprising the phosphorus-functional polyurethane polymer as claimed in claim 13 , the product selected from the group consisting of a flame-retardant adhesion promoter, a filler-activator, a flame retardant, a flame-retardant coating, a foam, a sealing compound, a thermoplastic, a thermoset, or a rubber.

Assignees

• Covestro Ag
• Covestro Deutschland Ag

Inventors

• Mueller Thomas Ernst
• Guertler Christoph
• Laemmerhold Kai
• Subhani Muhammad Afzal
• Koehler Burkhard
• Leitner Walter

Classifications

• C08G64/42

  Chemical after-treatment · CPC title

• C08G64/34

  and cyclic ethers · CPC title

• C09J175/08

  from polyethers · CPC title

• C09D5/18

  Fireproof paints {including high temperature resistant paints} · CPC title

• C08G18/4684

  containing phosphorus · CPC title