Polyurethane, process for producing the same, and process for producing polyurethane foam

• US 5,223,547 A
• Filed: 11/25/1991
• Issued: 06/29/1993
• Est. Priority Date: 11/27/1990
• Status: Expired due to Fees

• Current Assignee: KAO Corporation
• Original Assignee: KAO Corporation
• Inventors: Abe, Hiroshi, Fukushima, Tetsuaki, Harada, Shoichiro, Kitagawa, Hiroshi, Morii, Masayoshi, Isayama, Yasutoshi
• Primary Examiner(s): WELSH JR, MAURICE
• Application Number:
  US07/797,350
• Time in Patent Office: 582 Days
• Field of Search: 521/78, 521/131, 521/164, 521/167, 528/49, 528/78, 528/85
• US Class Current: 521/78
• CPC Class Codes: C08G 18/1825 having hydroxy or primary amino groups
• CPC Class Codes: C08G 18/2875 Monohydroxy compounds containing tertiary amino groups
• CPC Class Codes: C08G 18/3271 Hydroxyamines
• CPC Class Codes: C08G 18/3275 containing two hydroxy groups
• CPC Class Codes: C08G 18/5021 having nitrogen
• CPC Class Codes: C08G 18/6688 with compounds of group C08G18/3271
• CPC Class Codes: C08G 2110/0008 flexible
• CPC Class Codes: C08G 2110/0025 rigid
• CPC Class Codes: C08G 2110/005 < 50kg/m3
• CPC Class Codes: C08G 2110/0083 prepared using water as the sole blowing agent

Abstract

Processes for producing a polyurethane, a rigid polyurethane foam, a flexible polyurethane foam and a spray type rigid polyurethane foam are disclosed.

In these processes, a specified tertiary aminoalcohol is used as a polyol component and a catalyst.

Claims

1. A process for producing a polyurethane, comprising the step of reacting a polyisocyanate component with a polyol component, wherein said polyol component comprises, as all or part thereof, a tertiary aminoalcohol having the formula (I):

##STR10## wherein each R₁ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₂ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, and an aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein n is a positive number of 2 to 50.

2. The process according to claim 1, wherein each R₁ is straight or branched alkylene having 6 to 9 carbon atoms, each R₂ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

3. The process according to claim 1, wherein said polyol component comprises 1 to 50% by weight of said tertiary aminoalcohol having the formula (I).

4. The process according to claim 1, wherein said reacting of said polyisocyanate component with said polyol component is carried out in the presence of a third component comprising a tertiary aminoalcohol having the formula (II):

##STR11## wherein each R₃ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₄ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, and aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein m is a positive number of 2 to 50.

5. The process according to claim 4, wherein the amount of said third component having formula (II) is 30% or less by weight, based on the total amount of said tertiary aminoalcohol having formula (I) and said tertiary aminoalcohol having formula (II).

6. The process according to claim 4, wherein each R₃ is straight or branched alkylene having 6 to 9 carbon atoms, each R₄ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

7. A polyurethane produced by the process of claim 1 or 4.

31. The process according to claim 1, wherein said polyol component comprises 1 to 50% by weight of said tertiary aminoalcohol having formula (I).

32. The process according to claim 1, wherein each R₁ is --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero to 15, and q is 1 to 15.

33. The process according to claim 4, wherein each R₃ is --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero to 15, and q is 1 to 15.

34. The polyurethane according to claim 7, wherein each R₁ is straight or branched alkylene having 6 to 9 carbon atoms, each R₂ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

35. The polyurethane according to claim 7, wherein said polyol component comprises 1 to 50% by weight of said tertiary aminoalcohol having the formula (I).

36. A polyurethane produced by the process of claim 4, wherein the amount of said third component having formula (II) is 30% or less by weight, based on the total amount of said tertiary aminoalcohol having formula (I) and said tertiary aminoalcohol having formula (II).

37. The polyurethane according to claim 36, wherein each R₃ is straight or branched alkylene having 6 to 9 carbon atoms, each R₄ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

8. A process for producing a polyurethane foam, comprising the step of reacting a polyisocyanate component with a polyol component in the presence of a foaming agent, wherein said polyol component comprises, as all or part thereof, a tertiary aminoalcohol having the formula (I):

##STR12## wherein each R₁ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₂ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms and aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein n is a positive number of 2 to 50.

9. The process according to claim 8, wherein each R₁ is straight or branched alkylene having 6 to 9 carbon atoms, each R₂ is straight or branched alkyl having 2 to 4 carbon atoms, and n is a positive number of 1 to 30.

10. The process according to claim 8, wherein said polyol component comprises 1 to 50% by weight of said tertiary aminoalcohol having the formula (I).

11. The process according to claim 8, wherein said reacting of said polyisocyanate component with said polyol component is carried out in the presence of a third component comprising a tertiary aminoalcohol having the formula (II):

##STR13## wherein each R₃ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₄ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, and aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein m is a positive number of 2 to 50.

12. The process according to claim 11, wherein the amount of said third component having formula (II) is 30% or less by weight, based on the total amount of said tertiary aminoalcohol having formula (I) and said tertiary aminoalcohol having formula (II).

13. The process according to claim 11, wherein each R₃ is straight or branched alkylene having 6 to 9 carbon atoms, each R₄ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

14. The process according to claim 8 or 11, wherein said reacting of said polyisocyanate component with said polyol component is carried out in the presence of a compound selected from the group consisting of aliphatic amines and aromatic amines.

15. The process according to claim 14, wherein the amount of said compound selected from the group consisting of aliphatic amines and aromatic amines is 1 to 30 parts by weight, based on 100 parts by weight of the total amount of said polyol component.

16. The process according to claim 8 or 11, wherein said reacting of said polyisocyanate component with said polyol component is carried out in the presence of one or more compounds selected from the group consisting of triethanolamine, tolylenediamine and a diamine compound represented by formula (III):

space="preserve" listing-type="equation">H.sub.2 N--R.sub.5 --NH.sub.2 (III)

wherein R₅ is straight or branched alkylene having 2 to 8 carbon atoms.

17. The process according to claim 8 or 11, wherein said foaming agent is selected from the group consisting of H₂ O, 1,1-dichloro-2,2,2-trifluoroethane, and 2-dichloro-2-trifluoroethane.

18. The process according to claim 8 or 11, wherein said polyurethane foam is a rigid polyurethane foam.

19. The process according to claim 18, wherein said polyol component further comprises a polyol having an OH value of 1000 or above.

20. The process according to claim 18, wherein said polyol component further comprises ethyleneglycol, glycerol, or mixtures thereof.

21. The process according to claim 18, wherein the average OH value of said polyol component is 300 or above.

22. The process according to claim 8 or 11, wherein said polyurethane foam is a flexible polyurethane foam.

23. The process according to claim 22, wherein the average OH value of said polyol component is 200 or below.

24. The process according to claim 22, wherein said foaming agent is H₂ O, and wherein said foaming agent is used in an amount of 2 to 8 parts by weight, based on 100 parts by weight of the total amount of said polyol component.

38. The process according to claim 8, wherein each R₁ is --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero to 15, and q is 1 to 15.

39. The process according to claim 11, wherein each R₃ is --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero to 15, and q is 1 to 15.

25. A process for producing a polyurethane foam by the spray method, comprising the step of spraying a mixture containing reacting raw materials and a foaming agent and the step of reacting a polyisocyanate component with a polyol component in the presence of a foaming agent, wherein said polyol component comprises as, all or part thereof, a tertiary aminoalcohol having formula (I):

##STR14## wherein each R₁ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₂ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms, and aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein n is a positive number of 2 to 50; and

wherein said foaming agent comprises H₂ O in an amount of 2 to 8 parts by weight, based on 100 parts by weight of the total amount of said polyol component.

26. The process according to claim 25, wherein each R₁ is straight or branched alkylene having 6 to 9 carbon atoms, each R₂ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

27. The process according to claim 25, wherein said polyol component comprises 1 to 50% by weight of said tertiary aminoalcohol having the formula (I).

28. The process according to claim 25, wherein said reacting of said polyisocyanate component with said polyol component is carried out in the presence of a third component comprising a tertiary aminoalcohol having formula (II):

##STR15## wherein each R₃ is selected from the group consisting of straight or branched alkylene having 2 to 24 carbon atoms, cycloalkylene having 3 to 24 carbon atoms, alicyclic alkylene having 4 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, arylene having 6 to 24 carbon atoms, aralkylene having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene position, and --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero or a positive number, and q is a positive number, each R₄ is selected from the group consisting of straight or branched alkyl having 1 to 24 carbon atoms, aryl having 6 to 24 carbon atoms and aralkyl having 7 to 24 carbon atoms and having 1 to 6 carbon atoms in the alkylene portion, and wherein m is a positive number of 2 to 50.

29. The process according to claim 28, wherein the amount of said third component having formula (II) is 30% or less by weight, based on the total amount of said tertiary aminoalcohol having formula (I) and said tertiary aminoalcohol having formula (II).

30. The process according to claim 28, wherein each R₃ is straight or branched alkylene having 6 to 9 carbon atoms, each R₄ is straight or branched alkyl having 1 to 4 carbon atoms, and n is a positive number of 2 to 30.

40. The process according to claim 25, wherein each R₁ is --(CH₂ CH₂ O)_p --(CH₂ CH₂)_q --, wherein p is zero to 15, and q is 1 to 15.