Impact resistant polyureaurethane and method of preparation

• US 20030096935A1
• Filed: 11/05/2002
• Published: 05/22/2003
• Est. Priority Date: 11/16/2001
• Status: Abandoned Application

• Current Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Original Assignee: PPG Industries Ohio Incorporated (Nouryon BV)
• Inventors: Smith, Robert A., McDonald, William H., Nagpal, Vidhu J.
• Application Number:
  US10/287,880
• Publication Number:
  US 20030096935A1
• Time in Patent Office: Days
• US Class Current: 528/44
• CPC Class Codes: C08G 18/12 using two or more compounds having active hydrogen in the first polymerisation step
• CPC Class Codes: C08G 18/3206 aliphatic
• CPC Class Codes: C08G 18/3225 Polyamines
• CPC Class Codes: C08G 18/3243 containing two or more aromatic rings
• CPC Class Codes: C08G 18/3814 Polyamines
• CPC Class Codes: C08G 18/4018 Mixtures of compounds of group C08G18/42 with compounds of group C08G18/48
• CPC Class Codes: C08G 18/4277 Caprolactone and/or substituted caprolactone
• CPC Class Codes: C08G 18/6611 having at least three hydroxy groups
• CPC Class Codes: C08G 18/6644 having at least three hydroxy groups
• CPC Class Codes: C08G 18/6677 having at least three hydroxy groups
• CPC Class Codes: C08G 18/758 containing two or more cycloaliphatic rings
• CPC Class Codes: C08L 75/04 Polyurethanes
• CPC Class Codes: G02B 1/041 Lenses

Abstract

The present invention relates to a polyether-containing polyureaurethane. The polyureaurethane can include a prepolymer comprising a polyisocyanate and a polyether-containing polyol material. The prepolymer can be reacted with an amine-containing curing agent to produce the polyureaurethane of the present invention. In an embodiment, the polyether-containing polyureaurethane when at least partially cured and when tested as a lens with a hard coating on both surfaces having a maximum center thickness of 2.2 mm in a plano configuration, can have an impact resistance of at least 148 feet per second as defined by The High Impact Test.

Claims

1. A polyether-containing polyureaurethane, said polyureaurethane when at least partially cured and when tested as a lens with a hard coating on both surfaces having a maximum center thickness of 2.2 mm in a plano configuration, has an impact resistance of at least 148 feet per second as defined by The High Impact Test.

2. The polyether-containing polyureaurethane of claim 1 comprising block moieties derived from a polyether polyol.

3. The polyether-containing polyureaurethane of claim 2 wherein said polyether polyol comprises the following formula:

H—

(O—

CRRCRR—

Y_n)_a—

(CRRCRR—

Y_n—

O)_b—

(CRRCRR—

Y_n—

O)_c—

H

wherein R can represent hydrogen or C₁-C₆ alkyl;

Y can represent CH₂;

n can be an integer from 0 to 6;

a, b, and c can each be an integer from 0 to 300, wherein a, b and c are chosen such that the weight average molecular weight of the polyol does not exceed 32,000.

4. The polyether-containing polyureaurethane of claim 1 having a viscosity of less than 2,000 cPs at 73°

C.

5. The polyether-containing polyureaurethane of claim 1 comprising a prepolymer and an amine-containing curing agent.

6. The polyether-containing polyureaurethane of claim 5 wherein said prepolymer comprises a polyisocyanate and at least one polyether-containing polyol material.

7. The polyether polyureaurethane of claim 6 wherein said polyisocyanate is chosen from aliphatic polyisocyanates, cycloaliphatic polyisocyanates, aromatic polyisocyanates, and mixtures thereof.

8. The polyether polyureaurethane of claim 7 wherein said polyisocyanate is chosen from aliphatic diisocyanates, cycloaliphatic diisocyanates, and mixtures thereof.

9. The polyether polyureaurethane of claim 7 wherein said polyisocyanate is chosen from cyclohexylmethane and isomeric mixtures thereof.

10. The polyether-containing polyureaurethane of claim 7 wherein said polyisocyanate is chosen from trans-trans isomer of 4,4′

-methylenebis(cyclohexyl isocyanate).

11. The polyether-containing polyureaurethane of claim 7 wherein said polyisocyanate is chosen from 3-isocyanator-methyl-3,5,5-trimethyl cyclohexyl-isoxyanate;

meta-tetramethylxylene diisocyanate (1,3-bis(1-isocyanato-1-methylethyl)-benzene) and mixtures thereof.

12. The polyether-containing polyureaurethane of claim 5 wherein said prepolymer has an NCO/OH equivalent ratio of from 2.0 to less than 4.5.

13. The polyether-containing polyureaurethane of claim 5 wherein said polyether-containing polyol material is chosen from polyether polyols and mixtures thereof.

14. The polyether-containing polyureaurethane of claim 6 wherein said polyether-containing polyol material has a weight average molecular weight of from 200 to 32,000.

15. The polyether-containing polyureaurethane of claim 14 wherein said polyether-containing polyol material has a number average molecular weight of from 2,000 to 15,000.

16. The polyether-containing polyureaurethane of claim 5 wherein said amine-containing curing agent is chosen from materials having the following chemical formula and mixtures thereof:

17. The polyether-containing polyureaurethane of claim 5 wherein said amine-containing curing agent is 4,4′

-methylenebis(3-chloro-2,6-diethylaniline).

18. The polyether-containing polyureaurethane of claim 5 wherein said amine-containing curing agent is chosen from 2,4-diamino-3,5-diethyl-toluene;

2,6-diamino-3,5-diethyl-toluene and mixtures thereof.

19. The polyether-containing polyureaurethane of claim 5 wherein said amine-containing curing agent has a NCO/NH₂ equivalent ratio of from 1.0 NCO/0.60 NH₂ to 1.0 NCO/1.20 NH₂.

20. A polyether-containing polyureaurethane comprising the reaction product of:

(a) a prepolymer comprising a polyisocyanate and at least one polyether-containing polyol; and

(b) an amine-containing curing agent,

wherein said prepolymer has a NCO/OH equivalent ratio of from 2.0 to less than 4.5.

21. The polyether-containing polyureaurethane of claim 20 having a NCO/OH equivalent ratio of from 2.1 to 4.0.

22. The polyether-containing polyureaurethane of claim 20 comprising block moieties derived from a polyether polyol.

23. The polyether-containing polyureaurethane of claim 22 wherein said polyether polyol comprises the following formula:

H—

(O—

CRRCRR—

Y_n)_a—

(CRRCRR—

Y_n—

O)_b—

(CRRCRR—

Y_n—

O)_c—

H

wherein R can represent hydrogen or C₁-C₆ alkyl;

Y can represent CH₂;

n can be an integer from 0 to 6;

a, b, and c can each be an integer from 0 to 300, wherein a, b and c are chosen such that the weight average molecular weight of the polyol does not exceed 32,000.

24. The polyether-containing polyureaurethane of claim 20 having a viscosity of less than 2,000 cPs at 73°

C.

25. The polyether-containing polyureaurethane of claim 20 wherein said polyether-containing polyureaurethane comprises a prepolymer and an amine-containing curing agent.

26. The polyether-containing polyureaurethane of claim 25 wherein said prepolymer comprises a polyisocyanate and at least one polyether-containing polyol material.

27. The polyether-containing polyureaurethane of claim 26 wherein said polyisocyanate is chosen from aliphatic polyisocyanates, cycloaliphatic polyisocyanates, aromatic polyisocyanates, and mixtures thereof.

28. The polyether polyureaurethane of claim 27 wherein said polyisocyanate is chosen from aliphatic diisocyanates, cycloaliphatic diisocyanates, and mixtures thereof.

29. The polyether-containing polyureaurethane of claim 26 wherein said polyisocyanate is chosen from cyclohexylmethane and isomeric mixtures thereof.

30. The polyether-containing polyureaurethane of claim 26 wherein said polyisocyanate is chosen from trans, trans isomer of 4,4′

-methylenebis(cyclohexyl isocyanate).

31. The polyether-containing polyureaurethane of claim 26 wherein said polyisocyanate is chosen from 3-isocyanator-methyl-3,5,5-trimethyl cyclohexyl-isoxyanate;

meta-tetramethylxylene diisocyanate (1,3-bis(1-isocyanato-1-methylethyl)-benzene) and mixtures thereof.

32. The polyether-containing polyureaurethane of claim 25 wherein said prepolymer has an NCO/OH equivalent ratio of from 2.0 to less than 4.5.

33. The polyether-containing polyureaurethane of claim 26 wherein said polyether-containing polyol material is chosen from polyether polyols and mixtures thereof.

34. The polyether-containing polyureaurethane of claim 26 wherein said polyether-containing polyol material has a weight average molecular weight of from 200 to 32,000.

35. The polyether-containing polyureaurethane of claim 29 wherein said polyether-containing polyol material has a number average molecular weight of from 2,000 to 15,000.

36. The polyether-containing polyureaurethane of claim 25 wherein said amine-containing curing agent is chosen from materials having the following chemical formula and mixtures thereof:

37. The polyether-containing polyureaurethane of claim 25 wherein said amine-containing curing agent is 4,4′

-methylenebis(3-chloro-2,6-diethylaniline).

38. The polyether-containing polyureaurethane of claim 25 wherein said amine-containing curing agent is chosen from 2,4-diamino-3,5-diethyl-toluene;

2,6-diamino-3,5-diethyl-toluene and mixtures thereof.

39. The polyether-containing polyureaurethane of claim 25 wherein said amine-containing curing agent has a NCO/NH₂ equivalent ratio of from 1.0 NCO/0.60 NH₂ to 1.0 NCO/1.20 NH₂.

40. A method of preparing a polyether-containing polyureaurethane comprising the steps of:

(a) reacting a polyisocyanate with at least one polyether-containing polyol to form a polyether-containing polyurea prepolymer; and

(b) reacting said prepolymer with an amine-containing curing agent,

wherein said prepolymer has a NCO/OH equivalent ratio of from 2.0 to less than 4.5.

41. The polyether-containing polyureaurethane of claim 40 having a viscosity of less than 2,000 cPs.

42. The polyether-containing polyureaurethane of claim 40 wherein said polyether-containing polyureaurethane comprises a prepolymer and an amine-containing curing agent.

43. The polyether-containing polyureaurethane of claim 42 wherein said prepolymer comprises a polyisocyanate and at least one polyether-containing polyol material.

44. The polyether-containing polyureaurethane of claim 43 wherein said polyisocyanate is chosen from aliphatic polyisocyanates, cycloaliphatic polyisocyanates, aromatic polyisocyanates, and mixtures thereof.

45. The polyether-containing polyureaurethane of claim 44 wherein said polyisocyanate is chosen from aliphatic diisocyanates, cycloaliphatic diisocyanates, and mixtures thereof.

46. The polyether-containing polyureaurethane of claim 43 wherein said polyisocyanate is chosen from cyclohexylmethane and isomeric mixtures thereof.

47. The polyether-containing polyureaurethane of claim 43 wherein said polyisocyanate is chosen from trans- trans isomer of 4,4′

-methylenebis(cyclohexyl isocyanate).

48. The polyether-containing polyureaurethane of claim 43 wherein said polyisocyanate is chosen from 3-isocyanator-methyl-3,5,5-trimethyl cyclohexyl-isoxyanate;

meta-tetramethylxylene diisocyanate (1,3-bis(1-isocyanato-1-methylethyl)-benzene) and mixtures thereof.

49. The polyether-containing polyureaurethane of claim 42 wherein said prepolymer has an NCO/OH equivalent ratio of from 2.1 to less than 4.0.

50. The polyether-containing polyureaurethane of claim 43 wherein said polyether-containing polyol material is chosen from polyether polyols and mixtures thereof.

51. The polyether-containing polyureaurethane of claim 43 wherein said polyether-containing polyol material has a number average molecular weight of from 200 to 32,000.

52. The polyether-containing polyureaurethane of claim 46 wherein said polyether-containing polyol material has a number average molecular weight of from 2,000 to 15,000.

53. The polyether-containing polyureaurethane of claim 43 comprising block moieties derived from a polyether polyol.

54. The polyether-containing polyureaurethane of claim 43 wherein said polyether polyol comprises the following formula:

H—

(O—

CRRCRR—

Y_n)_a—

(CRRCRR—

Y_n—

O)_b—

(CRRCRR—

Y_n—

O)_c—

H

56. The polyether-containing polyureaurethane of claim 42 wherein said amine-containing curing agent is chosen from materials having the following chemical formula and mixtures thereof:

57. The polyether-containing polyureaurethane of claim 42 wherein said amine-containing curing agent is 4,4′

-methylenebis(3-chloro-2,6-diethylaniline).

58. The polyether-containing polyureaurethane of claim 42 wherein said amine-containing curing agent is chosen from 2,4-diamino-3,5-diethyl-toluene;

2,6-diamino-3,5-diethyl-toluene and mixtures thereof.

59. The polyether-containing polyureaurethane of claim 42 wherein said amine-containing curing agent has a NCO/NH₂ equivalent ratio of from 1.0 NCO/0.60 NH₂ to 1.0 NCO/1.20 NH₂.

55. wherein R can represent hydrogen or C₁-C₆ alkyl;

Y can represent CH₂;

n can be an integer from 0 to 6;

a, b, and c can each be an integer from 0 to 300, wherein a, b and c are chosen such that the weight average molecular weight of the polyol does not exceed 32,000.

60. An optical article comprising a polyether-containing polyureaurethane, said polyether-containing polyureaurethane when at least partially cured and when tested as a lens with a hard coating on both surfaces having a maximum center thickness of 2.2 mm in a piano configuration, has an impact resistance of at least 148 feet per second as defined by The High Impact Test.

61. An optical article comprising a polyether-containing polyureaurethane comprising the reaction product of:

(a) a prepolymer comprising an polyisocyanate and at least one polyether-containing polyol; and

(b) an amine-containing curing agent, wherein said prepolymer has a NCO/OH equivalent ratio of from 2.0 to 4.5.

62. A photochromic article comprising a polyether-containing polyureaurethane, said polyether-containing polyureaurethane when at least partially cured and when tested as a lens with a hard coating on both surfaces having a maximum center thickness of 2.2 mm in a piano configuration, has an impact resistance of at least 148 feet per second as defined by The High Impact Test.

63. A photochromic article comprising a polyether-containing polyureaurethane comprising the reaction product of:

(a) a prepolymer comprising an polyisocyanate and at least one polyether-containing polyol; and

(b) an amine-containing curing agent, wherein said prepolymer has a NCO/OH equivalent ratio of from 2.0 to 4.5.