Divalent phosphazenium salt and polyalkylene oxide composition containing the same, as well as polyurethane-forming composition containing the polyalkylene oxide composition

Patent metadata

Field	Value
Publication number	US-12110304-B2
Application number	US-201916977734-A
Country	US
Kind code	B2
Filing date	Mar 5, 2019
Priority date	Mar 7, 2018
Publication date	Oct 8, 2024
Grant date	Oct 8, 2024

Abstract

Provided are a divalent phosphazenium salt which is neutral and is excellent in thermal stability and aldehyde scavenging ability, and a method for producing the same. Also provided are a polyalkylene oxide composition having a volatile aldehyde amount reduced, having generation of odor and turbidity suppressed and being excellent in urethanization reactivity, and a method for producing such a polyalkylene oxide composition, as well as a polyurethane-forming composition containing the polyalkylene oxide composition. A divalent phosphazenium salt having a specific structure. Also, a polyalkylene oxide composition comprising a divalent phosphazenium salt having a specific structure and a polyalkylene oxide, a method for producing the same, and a polyurethane-forming composition containing the same.

First claim

The invention claimed is:

1. A divalent phosphazenium salt represented by the formula (1):

in the formula (1),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, a ring structure in which R 1 and R 2 are bonded to each other, or a ring structure in which a plurality of R 1 or R 2 are bonded to each other;
A n− represents a deprotonated form of an organic sulfonic acid or organic disulfonic acid;
either one of n and m is 1, and the other is 2; and
a is 2 when Y is a carbon atom and 3 when Y is a phosphorus atom.

2. A divalent phosphazenium salt represented by the formula (2):

in the formula (2),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, a ring structure in which R 1 and R 2 are bonded to each other, or a ring structure in which a plurality of R 1 or R 2 are bonded to each other; and
A − represents a deprotonated form of an organic sulfonic acid.

3. A divalent phosphazenium salt represented by the formula (3):

in the formula (3),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, or a ring structure in which R 1 and R 2 are bonded to each other;
A n− represents a deprotonated form of an organic sulfonic acid or organic disulfonic acid;

and
either one of n and m is 1, and the other is 2.

4. The divalent phosphazenium salt according to claim 1 , characterized in that R 1 and R 2 are methyl groups, and A n− or A − is a deprotonated form of dodecylbenzenesulfonic acid, a linear alkylbenzenesulfonic acid (soft type), or a branched chain alkylbenzenesulfonic acid (hard type).

5. The divalent phosphazenium salt according to claim 1 , characterized in that the pH of a 0.01 mol/L aqueous solution of the divalent phosphazenium salt is at least 5 and at most 8.

6. An aldehyde scavenger containing the divalent phosphazenium salt as defined in claim 1 .

7. A method for producing the divalent phosphazenium salt as defined in claim 1 , characterized by reacting at least 2 mol of an organic sulfonic acid to 1 mol of the phosphazenium salt represented by the formula (4):

in the formula (4),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, a ring structure in which R 1 and R 2 are bonded to each other, or a ring structure in which a plurality of R 1 or R 2 are bonded each other;
X − represents a hydroxy anion, a C 1-4 alkoxy anion, a carboxy anion, a C 2-5 alkylcarboxy anion, or a hydrogen carbonate anion; and
a is 2 when Y is a carbon atom and 3 when Y is a phosphorus atom.

8. A method for producing the divalent phosphazenium salt as defined in claim 2 , characterized by reacting at least 2 mol of an organic sulfonic acid to 1 mol of the phosphazenium salt represented by the formula (5):

in the formula (5),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, a ring structure in which R 1 and R 2 are bonded to each other, or a ring structure in which a plurality of R 1 or R 2 are bonded to each other; and
X − is a hydroxy anion, a C 1-4 alkoxy anion, a carboxy anion, a C 2-5 alkylcarboxy anion, or a hydrogen carbonate anion.

9. The method for producing the divalent phosphazenium salt as defined in claim 3 , characterized by reacting at least 2 mol of an organic sulfonic acid to 1 mol of the phosphazenium salt represented by the formula (6):

in the formula (6),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, or a ring structure in which R 1 and R 2 are bonded to each other;
X − represents a hydroxy anion, a C 1-4 alkoxy anion, a carboxy anion, a C 2-5 alkylcarboxy anion, or a hydrogen carbonate anion.

10. A polyalkylene oxide composition characterized by comprising the divalent phosphazenium salt as defined in claim 1 and a polyalkylene oxide.

11. The polyalkylene oxide composition according to claim 10 , characterized in that when measured by the following measurement method, the amount of volatilized acetaldehyde is at most 0.9 ppm, and the amount of volatilized propionaldehyde is at most 3.0 ppm:
[Measurement method]
(I): 10 g of the sample is put in a container having an internal volume of 30 ml,
(II): after (I), nitrogen bubbling is conducted at 0.5 L/min under heating at 65° C. for 2 hours to measure the amounts of volatilization.

12. The polyalkylene oxide composition according to claim 10 , characterized in that the pH of the polyalkylene oxide composition measured in accordance with the method described in JIS K-1557-5 is at least 5 and at most 8.

13. A polyalkylene oxide composition characterized by comprising the divalent phosphazenium salt as defined in claim 2 and a polyalkylene oxide.

14. A polyurethane-forming composition comprising
(A) the polyalkylene oxide composition as defined in claim 10 and
(B) an isocyanate compound.

15. A method for producing the polyalkylene oxide composition as defined in claim 13 , characterized in that a polymerization reaction of an alkylene oxide is conducted in the presence of the phosphazenium salt represented by the formula (5) and an active hydrogen-containing compound to produce a polyalkylene oxide, and then, at least 2 mol of an organic sulfonic acid is added to 1 mol of the phosphazenium salt:

in the formula (5),
R 1 and R 2 represent each independently a hydrogen atom, a C 1-20 hydrocarbon group, a ring structure in which R 1 and R 2 are bonded to each other, or a ring structure in which a plurality of R 1 or R 2 are bonded to each other; and
X − represents a hydroxy anion, a C 1-4 alkoxy anion, a carboxy anion, a C 2-5 alkylcarboxy anion, or a hydrogen carbonate anion.

Assignees

• Tosoh Corp

Inventors

• Inoue Yoshiaki
• Yamamoto Toshihide
• Mori Katsuaki

Classifications

• C08L71/02

  Polyalkylene oxides · CPC title

• C08K5/5399

  Phosphorus bound to nitrogen · CPC title

• C07C309/31

  by alkyl groups containing at least three carbon atoms · CPC title

• C07F9/062

  Organo-phosphoranes without P-C bonds · CPC title

• C07F9/24 Primary

  Esteramides · CPC title