IP Library Granted Patent US 10,344,136
Granted Patent B2
US 10,344,136 · App. 15/651,848 · Granted Jul 9, 2019

Mixtures containing 1,1,1,3,3,3-hexafluorobutene and 1-chloro-3,3,3-trifluoropropene

Inventors: Mary C. Bogdan (Buffalo, NY); Clifford P. Gittere (Amherst, NY); James M. Bowman (Geneva, IL); Yiu Keung Ling (Amherst, NY); David J. Williams (East Amherst, NY)
Assignee: Honeywell International Inc.
C08J9/144C08G18/14C08G18/3206C08G18/4208C08G18/48C08G18/7671C08J9/146C08J9/149C08J2203/142C08J2203/162C08J2203/182C08J2203/202C08J2371/10C08J2375/04C08J2375/08
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Quick Facts
Patent No.
US 10,344,136
App. No.
15/651,848
Granted
Jul 9, 2019
Kind
B2
Abstract

The present invention relates to mixtures of 1,1,1,4,4,4-hexafluorobutene (1336mzzm) and 1-chloro-3,3,3-trifluoropropene (1233zd). The blends are useful as blowing agents for polymer foam, solvents, aerosol propellants and heat transfer media.

Claims (22)

1. A method of forming a foam of improved thermal thermal insulating properties comprising:

(a) adding to a foamable or foaming composition a blowing agent composition comprising: from about 30 mole % to about 70 mole % of 1,1,1,4,4,4-hexafluorobutene (1336mzzm) and from about 30 mole % to about 70 mole % of 1-chloro-3,3,3-trifluoropropene (1233zd); and optionally at least one adjuvant selected from the group consisting of co-blowing agent(s), polyol(s), surfactant(s), polymer modifier(s), colorant(s), dye(s), solubility enhancer(s), flammability suppressant(s), flame retardants(s), antibacterial agent(s), viscosity reduction modifier(s), filler(s), vapor pressure modifier(s), nucleating agent(s), catalyst(s) and combination of any two or more of these; and

(b) forming from said foamable or foaming composition a foam having an initial k-factor (BTU in/hr ft2° F.) at 40° F. of not greater than about 0.14.

2. The method of claim 1 wherein said 1-chloro-3,3,3-trifluoropropene (1233zd) comprises trans-1-chloro-3,3,3-trifluoropropene.

3. The method of claim 1 wherein said 1-chloro-3,3,3-trifluoropropene (1233zd) comprises from about 90 weight percent to about 100 weight percent trans-1-chloro-3,3,3-trifluoropropene and from about 0 weight percent to about 10 weight percent cis-1-chloro-3,3,3-trifluoropropene.

4. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises cis-1,1,1,4,4,4-hexafluorobutene.

5. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 50 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and from about 0 weight percent to about 50 weight percent trans-1,1,1,4,4,4-hexafluorobutene.

6. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 75 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and from about 0 weight percent to about 25 weight percent trans-1,1,1,4,4,4-hexafluorobutene.

7. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 90 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and from about 0 weight percent to about 10 weight percent trans-1,1,1,3,3,3-hexafluorobutene.

8. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene is provided in said blowing agent in an amount from about 40 to about 60 mole percent and said 1-chloro-3,3,3-trifluoropropene is provided in said blowing agent in an amount from about 40 to about 60 mole percent.

9. The method of claim 1 wherein said 1,1,1,4,4,4-hexafluorobutene is provided in said blowing agent in an amount of about 50 mole percent and said 1-chloro-3,3,3-trifluoropropene is provided in said blowing agent in an amount of about 50 mole percent.

10. The method of claim 1 wherein said adjuvant comprises at least one co-blowing agent selected from the group consisting of water, CO2, CFCs, HCCs, HCFCs, C1-C5 alcohols, C1-C4 aldehydes, C1-C4 ketones, C1-C4 ethers and diethers, organic acids, and combinations of two or more of these.

11. The method of claim 1 wherein said adjuvant comprises water as at least one co-blowing agent.

12. A method of forming a spray foam of improved thermal insulating properties comprising:

(a) adding to a foamable or foaming composition a blowing agent composition comprising: from about 30 mole % to about 70 mole % of 1,1,1,4,4,4-hexafluorobutene (1336mzzm); from about 30 mole % to about 70 mole %_1-chloro-3,3,3-trifluoropropene (1233zd); and optionally at least one adjuvant selected from the group consisting of co-blowing agent(s), polyol(s), surfactant(s), polymer modifier(s), colorant(s), dye(s), solubility enhancer(s), flammability suppressant(s), flame retardants(s), antibacterial agent(s), viscosity reduction modifier(s), filler(s), vapor pressure modifier(s), nucleating agent(s), catalyst(s) and combination of any two or more of these, wherein said 1336mzzm and said 1233zd are not azeotropic; and

(b) spray applying said foam to produce a foam having an initial k-factor (BTU in/hr ft2° F.) at 40° F. of not greater than about 0.14.

13. The method of claim 12 wherein said 1-chloro-3,3,3-trifluoropropene (1233zd) comprises trans-1-chloro-3,3,3-trifluoropropene.

14. The method of claim 12 wherein said 1-chloro-3,3,3-trifluoropropene (1233zd) comprises from about 90 weight percent to about 100 weight percent trans-1-chloro-3,3,3-trifluoropropene and up to about 10 weight percent cis-1-chloro-3,3,3-trifluoropropene.

15. The method of claim 12 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises cis-1,1,1,4,4,4-hexafluorobutene.

16. The method of claim 12 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 50 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and up to about 50 weight percent trans-1,1,1,4,4,4-hexafluorobutene.

17. The method of claim 12 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 75 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and up to about 25 weight percent trans-1,1,1,4,4,4-hexafluorobutene.

18. The method of claim 12 wherein said 1,1,1,4,4,4-hexafluorobutene (1336mzzm) comprises from about 90 weight percent to about 100 weight percent cis-1,1,1,4,4,4-hexafluorobutene and from about 0 weight percent to about 10 weight percent trans-1,1,1,3,3,3-hexafluorobutene.

Assignments (3)
NUNC PRO TUNC ASSIGNMENT Recorded Apr 12, 2026
From: HONEYWELL INTERNATIONAL INC.
To: SOLSTICE ADVANCED MATERIALS US, INC.
Reel/Frame 074344/0092 →
SECURITY INTEREST Recorded Jan 12, 2026
From: SOLSTICE ADVANCED MATERIALS US, INC.
To: JPMORGAN CHASE BANK, N.A., AS ADMINISTRATIVE AGENT
Reel/Frame 074569/0260 →
ASSIGNMENT OF ASSIGNOR'S INTEREST Recorded Mar 6, 2025
From: BOGDAN, MARY C.; GITTERE, CLIFFORD P.; BOWMAN, JAMES M.; LING, YIU KEUNG; WILLIAMS, DAVID J.
To: HONEYWELL INTERNATIONAL INC.
Reel/Frame 070426/0387 →
Continuity (4)
Division 14868222 · Sep 28, 2015
Division 13276369 · Oct 19, 2011
Provisional Application 61407708 · Oct 28, 2010
Related Publication 20170313841A1 · Nov 2, 2017
Cited By (1)
US 12,415,108