IP Library › Granted Patent US 12,129,329
Granted Patent B2
US 12,129,329 · App. 17/214,998 · Granted Oct 29, 2024

Production of polyurethane systems

Inventors: Eva Emmrich-Smolczyk (Essen, DE); Mladen Vidakovic (Duisburg, DE); Kai-Oliver Feldmann (Essen, DE); Annegret Terheiden (Alpen, DE)
Assignee: Evonik Operations GmbH
C08G18/3203C08G18/0871C08G18/1808C08G18/1825C08G18/185C08G18/2027C08G18/2036C08G18/3268C08G18/3275C08G18/4816C08G18/4829C08G18/6688C08G18/7671C08K5/17C08K9/12C08G2110/0008C08G2110/0016C08G2110/0025C08G2110/0083C08K5/31
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Quick Facts
Patent No.
US 12,129,329
App. No.
17/214,998
Granted
Oct 29, 2024
Kind
B2
Abstract

The invention provides a process for production of polyurethane systems by reacting at least one polyol component with at least one isocyanate component in the presence of one or more catalysts for the isocyanate-polyol and/or isocyanate-water reactions and/or the trimerization of isocyanate, wherein said reacting is carried out in the presence of carrier material and polyamine P.

Claims (61)

1. A process for production of polyurethane systems, comprising;

reacting a reaction mixture comprising 25-75 wt. % of a polyol component comprising a polyetherol, and optionally water; an isocyanate component;

one or more catalysts for reaction of the isocyanate component and the polyetherol, for reaction of the isocyanate component and water, and/or

trimerization of the isocyanate component,

a carrier material; and

a polyamine P

wherein wt. % is based on a weight of said reaction mixture and

said reacting is carried out in the presence of a mass fraction of in total from 0.01 to 10 parts by weight of said carrier material and said polyamine P based on 100 parts by weight of the polyol component and wherein a relative amount of carrier material based on an amount of polyamine P is 0.1 to 10 wt. %, wherein the polyamine P results from the reaction of a guanidine salt with a polyamine of formula (I)

H 2 N—CH 2 —CH 2 —NH—(CH 2 —CH 2 —NH) x —CH 2 —CH 2 —NH 2   (I)

where x=1, and

wherein said carrier material used is a hydrophobized

silica.

2. The process according to claim 1 ,

wherein said reaction of the guanidine salt with the polyamine of formula (I) is carried out with a molar ratio of guanidine salt to the polyamine of formula (I), which is in the range from 5:1 to 1:5.

3. The process according to claim 1 , wherein the

polyamine P used is a compound of formula (II)

H[—(HN—CH 2 —CH 2 ) a —NH—C(═NHR + X − )] c —NH—(CH 2 —CH 2 —NH—) b H  (II)

which is obtained by reacting a guanidine salt with a compound of formula (I),

H 2 N—CH 2 —CH 2 —NH—(CH 2 —CH 2 —NH) x —CH 2 —CH 2 —NH 2   (I)

wherein x=1,

wherein in formula (II)

a=independently 0 to 6,

b=3,

c=independently 1 to 4,

R═H or (CH 2 —CH 2 —NH—) d H,

d=independently 0 to 6,

a may be 0 when d>0 and R is not H, or d may be 0 when a>0, or d and a

may each be 0,

X − =anion, and

wherein said reaction of the guanidine salt with the polyamine of formula (I) is carried out with a molar ratio of guanidine salt to the polyamine of formula (I), which is in the range from 2:3 to 1:3.

4. The process according to claim 1 , wherein the polyamine P and the carrier material are added separately from one another to the reaction mixture which serves to produce the polyurethane systems, the carrier material having been dispersed in a liquid, and wherein the polyurethane systems produced comprise from 0.1 to 3 wt % of a total amount of a carrier material and polyamine P.

5. The process according to claim 1 , wherein the polyurethane systems produced are polyurethane foams, and the polyamine P and the carrier material are mixed with one another and then added to the reaction mixture which serves to produce the polyurethane systems.

6. A polyurethane foam system, obtained by the process according to claim 1 .

7. The polyurethane foam system according to claim 6 , wherein the polyurethane foam system includes from 0.001 to 10 wt %, of carrier material and polyamine P.

8. The polyurethane foam system according to claim 6 , wherein the polyurethane foam system is a flexible polyurethane foam, a viscoelastic PU foam, an HR polyurethane foam, a semi-rigid polyurethane foam, a thermoformable polyurethane foam or an integral PU foam.

9. An article, selected from the group consisting of refrigerator insulation, an insulation panel, a sandwich element, pipe insulation, spray foam, 1-component can foam, 1.5-component can foam, a wood imitation article, modelling foam, packaging foam, a mattress, furniture cushioning, automotive seat cushioning, a headrest, a dashboard, an automotive interior, an automotive roof liner, a sound absorption material, a steering wheel, a shoe sole, carpet backing foam, filter foam, a sealing foam, an adhesive, and a coating comprising the polyurethane foam system according to claim 6 .

10. A process for reducing aldehyde emission from polyurethane systems, comprising admixing to the polyurethane systems or precursors thereof a carrier material and a polyamine P wherein the polyamine P is a reaction product wherein the polyamine P results from the reaction of a guanidine salt with a polyamine of formula (I)

H 2 N—CH 2 —CH 2 —NH—(CH 2 —CH 2 —NH) x —CH 2 —CH 2 —NH 2   (I)

where x=1,

in an amount of from 0.001 to 10 wt %, based on the overall weight of the polyurethane systems and wherein a relative amount of carrier material based on an amount of polyamine P is 0.1 to 10 wt. %, wherein the admixing takes place before and/or during the production of the polyurethane systems,

wherein the carrier material used is a hydrophobized silica.

11. The process for production of polyurethane systems according to claim 1 , wherein the polyurethane system produced have lower aldehyde emissions than otherwise equivalent polyurethane systems produced in the absence of polyamine P.

12. The process according to claim 1 , wherein the

polyamine P used is a compound of formula (II)

H[—(HN—CH 2 —CH 2 ) a —NH—C(═NHR + X − )] c —NH—(CH 2 —CH 2 —NH—) b H  (II)

which is obtained by reacting a guanidine salt with a compound of formula (I),

H 2 N—CH 2 —CH 2 —NH—(CH 2 —CH 2 —NH) x —CH 2 —CH 2 —NH 2   (I)

wherein x=1,

wherein in formula (II)

a=independently 3 to 5,

b=3,

c=independently 1 or 2,

R═H,

d=independently 3 to 5,

X − =chloride, and

wherein said reaction of the guanidine salt with the polyamine of formula (I) is carried out with a molar ratio of guanidine salt to the polyamine of formula (I), which is in the range from 5:1 to 1:5.

13. The process according to claim 12 , wherein a=b in the compound of formula (II).

14. A process for reducing aldehyde emission comprising formaldehyde, acetaldehyde, acrolein and benzaldehyde, from polyurethane foam systems, comprising admixing to the polyurethane foam systems or precursors thereof a carrier material and a polyamine P wherein the polyamine P results from the reaction of a guanidine salt with a polyamine of formula (I)

H 2 N—CH 2 —CH 2 —NH—(CH 2 —CH 2 —NH) x —CH 2 —CH 2 —NH 2   (I)

where x=1, in an amount of from 0.01 to 5 wt %, based on the overall weight of the polyurethane foam systems, wherein the admixing may take place before and/or during the production of the polyurethane foam systems, and

wherein the carrier material used is a hydrophobized silica and a relative amount of carrier material based on an amount of polyamine P is 0.1 to 10 wt. %.

Priority Claims (1)
EP 17192836 · Sep 25, 2017 · regional
Continuity (2)
Division 16127663 · Sep 11, 2018
Related Publication 20210214488A1 · Jul 15, 2021