WO1998006815A1

WO1998006815A1 - Alkylsiloxane compositions

Info

Publication number: WO1998006815A1
Application number: PCT/US1997/014213
Authority: WO
Inventors: Abid Nazarali Merchant; Barbara Haviland Minor; Shoeb Akberali Moiyadi
Original assignee: EI Du Pont de Nemours and Co
Current assignee: EIDP Inc
Priority date: 1996-08-13
Filing date: 1997-08-13
Publication date: 1998-02-19
Anticipated expiration: 1999-02-13
Also published as: AU3914797A

Abstract

Compositions containing alkylsiloxane and at least one compound selected from the group consisting of 1,1,1,2,3,4,4,5,5,5-decafluoropentane, nonafluoromethoxybutane, nonafluoroethoxybutane, dichloropentafluoropropane, 2,2-dichloro-1,1,1-trifluoroethane and isopropanol are described. These compositions are useful as cleaning agents, heat transfer media, and carrier fluids.

Description

ALKYLS1L0XANE COMPOSITIONS

CROSS-REFERENCE TO RELATED APPLICATION This application claims the benefit of U.S. Provisional Application No. 60/024,799 filed August 13, 1996.

FIELD OF THE INVENTION This invention relates to compositions containing alkylsiloxanes. These compositions include alkylsiloxane and at least one compound selected from the group consisting of 1,1, 1,2,3,4,4,5,5,5-decafluoropentane, nonafluoromethoxybutane, nonafiuoroethoxybutane, dichloropentafluoropropane, 2,2-dichloro-l, 1, 1-trifiuoroethane and isopropanol. These compositions are useful as cleaning agents, heat transfer media, and carrier fluids.

BACKGROUND OF THE INVENTION

Fluorinated hydrocarbons have many uses such as cleaning agents, drying agents or carrier fluids. Such compounds include 1, l,2-trichloro-l,2,2-trifluoroethane (CFC-113). In recent years it has been pointed out that certain kinds of fluorinated hydrocarbons released into the atmosphere may adversely affect the stratospheric ozone layer. Although this proposition has not yet been completely established, there is a movement toward the control of the use and production of certain chlorofluorocarbons (CFCs) and hydrochlorofluorocarbons (HCFCs) under an international agreement. There is a parallel concern about the contribution perfluorinated compounds make to global warming, therefore, it is desirable to find compounds that are partially fluorinated to reduce potential for global warming.

Accordingly there is a demand for the development of new compounds that have lower ozone depletion potential and lower global warming contribution than existing compounds while still achieving acceptable cleaning performance. ll is desirable to find partially fluorinated compounds for use as a cleaning agent to clean for example, silicone off medical instruments and tubing. Partially fluorinated compounds may also be useful as a carrier fluid, for example, to place a thin layer of silicone or another compound on a surface. To clean a surface containing silicone or to place silicone on a surface, it is desirable to add compounds to the partially fluorinated solvent to enhance solubility of silicone. It is particularly desirable that these compounds be non-flammable. These enhanced solvents may also be useful as heat transfer fluids, particularly in secondary loop systems. Enhanced solvents can also act as carriers for other compounds such as adhesion promoter accelerators, initiators and catalysts. Accordingly, it has been found that adding specific agents to partially fluorinated compounds can enhance solubility of residues, for example, silicone, enhance cleaning performance, act as carrier fluids and heat transfer fluids.

SUMMARY OF THE INVENTION The present invention relates to the following compositions: a first component, alkylsiloxane of the formula

where R is an alkyl group having from 1 to 10 carbon atoms and t is an integer from 1 to 5, and a second component, wherein the second component is selected from the group consisting of 1, 1, 1,2,3,4,4,5, 5, 5-decafluoropentane, nonafluoromethoxybutane, nonafiuoroethoxybutane and dichloropentafluoropropane and optionally, a third component, wherein the third component is selected from the group consisting of isopropanol and 2,2-dichloro-l,l,l-trifluoroethane. ^■ '- These compositions may be useful as cleaning agents, heat transfer media, silicone removal agents, and as carrier fluids for silicone, adhesion promoters or other compounds.

DETAILED DESCRIPTION 0 The present invention relates to the discovery of mixtures of alkylsiloxane and at least one of 1,1, 1,2,3,4,4,5,5, 5-decafluoropentane. nonafluoromethoxybutane, nonafiuoroethoxybutane, dichloropentafluoropropane, isopropanol and 2,2-dichloro-l. l, l- trifluoroethane.

1-99% of each of the above components can be used as cleaning agents, 5 heat transfer media, silicone removal agents, and as carrier fluids for compounds such as silicone, adhesion promoters or other compounds.

Nonafluoromethoxybutane (C4F₉OCH₃) isomers of the present invention include 1,1, l,2,2,3,3,4,4,-nonafluoro-4-methoxy-butane (C^OCF_JCF_TCF.CF-,),

1, 1, 1,2,3,3, -hexafluoro-2-(trifluoromethyl)-3-methoxy-propane (CH3OCF₂CF(CF₃)₂), 0 l. l, l,3,3,3-hexafluoro-2-methoxy-2-(trifluoromethyl)-propane (CH3OC(CF₃)3), and

1, 1, 1, 2,3, 3,4,4,4-nonafluoro-2-methoxy-butane (CH₃OCF(CF₃)CF₂CF₃), approximate isomer boiling point = 60°C;

Nonafiuoroethoxybutane (C F₉OC₂H₅) isomers of the present invention include l_>l,l,2,2,3,3,4,4-nonafluoro-4-ethoxybutane (CH3CH₂OCF₂CF-2CF₂CF3)_J 5 1, 1, l,2,3,3-hexafluoro-2-(trifluoromethyl)-3-ethoxyρropane (CH₃CH₂OCF₂CF(CF₃)₂).

1, 1, l,3,3,3-hexafluoro-2-ethoxy-2-(trifluoromethyl)-propane (CH₃CH₂OC(CF₃)3). and

1,1, l,2,3,3,4,4,4-nonafluoro-2-ethoxybutane (CH₃CH₂OCF(CF₃)CF2CF₃) with approximate isomer boiling points of 73°C;

Dichloropentafluoropropane isomers include l, l-dichloro-2,2,3,3,3- 0 pentafluoropropane (CHC1_CF₂CF₃, HCFC-225ca), boiling point = 50°C, and l,3-dichloro-l,l,2,2,3-pentafluoropropane (CHC1FCF₂CCIF₂, HCFC-225cb), boiling point

= 56°C. 2,2-dichloro-l, l, l-trifluoroethane (HCFC-123 or CHC1₂CF₃) has a boiling point of 27°C. Isopropanol (CH₃)₂CH0H has a boiling point of 82.2°C. Effective amounts o tlic.se compositions can contain from 10 to 60 weight percent alkylsiloxane and 40 to 90 weight percent of at least one of HFC-43-10mee, C4F₉OCH₃₎ CΛOQ∑HJ, HCFC-225ca, or HCFC-225cb. Effective amounts can also contain 1-30 weight percent alkylsiloxane, 9-50 weight percent HCFC-123, and 25-90 weight percent of at least one of HFC-43-10mee, C₄F₉OCH₃, C₄F₉OC₂H5, HCFC-225ca, or HCFC-225cb. Compositions may also contain effective amounts of 10-59 weight percent alkylsiloxane, 1-20 weight percent isopropanol, and 40-89 weight percent of at least one of HFC-43-10mee, C4F9OCH₃, CJ- _SOC-JHS, HCFC-225ca, or HCFC-225cb.

Specific examples illustrating the invention are given below. Unless otherwise stated therein, all percentages are by weight. It is to be understood that these examples are merely illustrative and in no way are to be interpreted as limiting the scope of the invention.

EXAMPLE 1 Flammabilitv Test A Penski-Martin Closed Cup flash point tester was filled with mixtures shown in Table 1. OS-10 is hexamethylsisiloxane and OS-20 is octamethyltrisiioxane. Flash points were determined in a temperature range from about -20C to 38C. No flash points were observed at any temperature for any mixture tested. Flammability was also tested by attempting to ignite mixtures in a pan with a spark and a flame. No ignitions resulted in mixtures tested.

TABLE 1

Flammability Data

Mixture Wt% Flash Point Ignition in Pan

HFC-43-10mee/OS-10

80/20 None 70/30 None

60/40 None

50/50 None

HFC-43 - 1 Omee/HCFC- 123/OS- 10

50/30/20 None None 60/20/20 None

55/25/20 None

60/25/15 None

45/35/20 None None

45/30/25 None None HFC-43- 1 Omee/OS-20 Isopropanol

50/40/10 None

60/30/10 None

70/20/10 None

EXAMPLE 2

A suitable container was filled with mixtures shown in Table 2 and mixed thoroughly at room temperature. Trans- 1,2-DCE is trans- 1,2-dichloroethylene (CC1=CC1). Dow Coming 360, Dow Corning 550, or Dow Corning 1107 medical grade silicone oil was then slowly added to each mixture until the blend would no longer dissolve the oil.

TΛI3LE 2

Mixture Weight Percent Wt. % Silicone Dissolved

DC-360 DC-550 DC-1 107

CFC-113 100 16.0

Hexane 100 16.0

43-10mee 65/15/20 0.5 cyclopentane/ trans- 1 ,2-dichloroethylene

43-10mee/ 85/5/10 0.5 cyclohexane trans- 1 ,2-dichloroethylene

43-10mee OS-10 60/40 10.02

50/50 23.0

43-10mee/123/OS-10 50/30/20 5.12 14.0 25.0

60/25/15 <1.0 1.68 9.0

60/20/10 <1.0 3.01 9.0

47.5/35/17.5 5.0 12.0 24.0

45/30/25 18.2

50/35/15 5.5

45/35/20 12.85

43-10mee/OS-20/ 50/40/10 3.5 isopropanol

Results show that the addition of hexamethyldisiloxane to HFC-43-10mee significantly improves silicone solubility. Alkysyloxane-containing blends can also act as silicone carrier fluids due to their ability to dissolve silicone. These blends also have the advantage of being non-flammable and non-toxic.

EXAMPLE 3 A suitable container was filled with the mixtures shown in Table 3. Pre- weighed tubing made of polyurethane was immersed in each mixture at a specified temperature for three minutes. Parts were then dried, weighed and observed for swelling. ΓΛI.LE

Weigh it Gain and Enlarcement

Pre-Test Post-Test % Wt Change in

Solvent Wt (kg) Wt (kg) BPf°C> Increase Dimension

CFC-113 0.1917 0.213 47 11.1 Enlarged

HFC-

43-10mee/ 0.174 0.2209 37 27.0 Enlarged and cyclopentane softened trans- 1,2-DCE

(65/15/20 wt%)

Hexane 0.1669 0.2112 68 26.5 Enlarged

HFC-43-10mee/ 0.1481 0.1481 55.5 0.0 No effect

123/OS-10

(85/15 wt%)

Results show the blends containing : alkylsiloxanes demonstrated significantly reduced weight gain and swelling versus the other compositions tested.

EXAMPLE 4

Polyurethane, nylon and ABS tubing were coated with silicone and then cleaned with a solution containing 85 weight percent HFC-43-10mee and 15 weight percent hexamethyldisiloxane. Results are shown in Table 4 below.

TABLE 4

Cleanabilitv

Tubing Tvpe Degree of Cleaning

Polyurethane Visually Clean

ABS Visually Clean

Nylon Visually Clean

Tubing also felt clean with no evidence of silicone remaining on the tubes EXAMPLE 5 Lengths of Polysilicone tubing (Boston Scientific) were cut with tube weight and diameter recorded. A suitable container was filled with solvent compositions as shown in Table 5. Each composition was heated to the vapor temperatures shown and tubing was immersed in the solvent for several minutes. Tubing was removed and allowed to dry for 30 seconds. Tubing was then reweighed and the diameter remeasured. The change in weight and diameter were calculated.

TABLE 5

Change in Change in Vapor

Wt% Weight (g) Diameter(in) T(°C)

3 minute immersion:

HCFC-225 100 +0.123 +0.016 53.5

CFC-113 100 +0.1738 +0.024 47.5

HFC-43-10mee/OS-10 50/50 +0.0778 +0.023 57.0

HFC-43-10mee/OS-20 50/50 +0.0942 +0.031 57.0

HCFC-225 100 +0.1182 +0.016 21.0

CFC-113 100 +0.0874 +0.020

HFC-43-10mee/OS-10 50/50 +0.0713 +0.018

HFC-43-10mee/OS-20 50/50 +0.0611 +0.023

15 minute immersion:

CFC-113 100 +0.3710 +0.038 21.0

HFC-43-10/123/OS-10 50/30/20 +0.1595 +0.026

HFC-43-10/OS-20 IPA 50/40/10 +0.1235 +0.023

HFC-43-10/OS-20/IPA 60/20/10 +0.1031 +0.021 ^M

HFC-43-10/OS-20/IPA 70/20/10 +0.0871 +0.019

For connecting polysilicone tubing using a solvent, it is desirable to have a significant increase in tube diameter without a large increase in tube weight. The samples containing alkysiloxanes generally showed adequate change in tube diameter and the smallest increase in tube weight. ADD1TIONAL COMPOUNDS Other components, such as aliphatic hydrocarbons having a boiling point of 0-100°C, hydrofluorocarbonalkanes having a boiling point of 0- 100°C, hydrofluoropropanes having a boiling point of between 0-100°C, hydrocarbon esters having a boiling point between 0-100°C, hydrochlorofluorocarbons having a boiling point between 0-100°C, hydrofluorocarbons having a boiling point of 0-100°C, hydrochlorocarbons having a boiling point between 0-100°C, chlorocarbons and perfluorinated compounds, can be added to the azeotropic or azeotrope-like compositions described above without substantially changing the properties thereof, including the constant boiling behavior, of the compositions. Examples of such components, which typically do not exceed about 10 weight percent of the total composition, include the following:

COMPOUND FORMULA boiline point. °C

HCFC-123 CHCljCFj 27

HCFC-141b CFC1₂CH₃ 32

HCFC-225aa CHF₂CC1₂CF₃ 53

HCFC-225da CC1F₂CHC1CF₃ 50

HFC-HFC-43-10mf CF₃CH₂CF₂CF₂CF3 52

HFC-HFC-43-10mcf CF₃CF₂CH₂CF₂CF₃ 52

FC-C-51-12 cyclo-C₄F₆(CF₃)₂ 45

CH₃OCF₂CHFCF₃ 52

HFC-C-354 cyclo-CF₂CF₂CH₂CH₂ 50

MEK CH₃C(O)C₂H_J 80

THF cyclo-OC<H₈ 66 methyl formate HC(O)OCH₃ 32 ethyl formate HC(O)OC₂HJ 54 methyl acetate CH₃C(O)OCH₃ 56 ethyl acetate CH₃C(O)OC₂H_$ 77

1,2-dichloroethane 84 acetonitrile 82 methylene chloride 40 heptane CH₃(CH₂)₅CH₃ 98 Λdditives such as lubricants, corrosion inhibitors, stabilizers, surfactants dyes and other appropriate materials may be added to the novel compositions of the invention for a variety of purposes provided they do not have an adverse influence on the composition, for their intended applications. Examples of stabilizers include nitromethane and nitroethane.

Claims

• ] 1 -CLA1MSWhat is claimed is:

1. A composition comprising effective amounts of alkylsiloxane and at least one compound selected from the group consisting of 1, 1, 1,2,3,4,4,5,5, 5- decafluoropentane, nonafluoromethoxybutane, nonafiuoroethoxybutane, dichloropentafluoropropane, 2,2-dichloro-l,l, l-trifluoroethane and isopropanol.

2. The composition of claim 1 comprising 10-60 weight percent alkylsiloxane and 40-90 weight percent 1,1, 1,2,3,4,4,5,5, 5-decafluoropentane; 10-60 weight percent alkylsiloxane and 40-90 weight percent nonafluoromethoxybutane; 10-60 weight percent alkylsiloxane and 40-90 weight percent nonafiuoroethoxybutane; 10-60 weight percent alkylsiloxane and 40-90 weight percent l,l-dichloro-2,2,3,3,3- pentafluoropropane; 10-60 weight percent alkylsiloxane and 40-90 weight percent 1,3- dichloro-l,l,2,2,3-pentafluoropropane; 10-60 weight percent alkylsiloxane, 1-89 weight percent l,l-dichloro-2,2,3,3,3-pentafluoropropane and 1-89 weight percent 1,3-dichloro- 1, 1,2,2,3-pentafluoropropane.

3. The composition of Claim 1 comprising 1-30 weight percent alkylsiloxane, 9-50 weight percent 2,2-dichloro-l,l. l-trifluoroethane, and 25-90 weight percent of at least one compound selected from the group consisting of 1,1, 1,2,3,4,4,5, 5, 5-decafluoropentane, nonafluoromethoxybutane, nonafiuoroethoxybutane, l,l-dichloro-2,2,3,3,3-pentafluoropropane and 1,3-dichloro- 1, 1,2,2,3-pentafluoropropane.

4. The composition of Claim 1 comprising 10-59 weight percent alkylsiloxane, 1-20 weight percent isopropanol, and 40-89 weight percent of at least one compound selected from the group consisting of 1, 1, 1,2,3, 4, 4,5,5, 5-decafluoropentane, b nυiiafluoioincllioxybutanc, nonaπuorocthoxybulanc, I , l -dichloro-2,2,3,3,3- pentafluoropropane and l,3-dichloro- l, l ,2,2,3-pentafluoropropane.

5. A composition comprising 1-30 weight percent hexamethyldisiloxane, 25-90 weight percent 1, 1, 1,2,3,4,4,5, 5, 5-decafluoropentane and 9-50 weight percent 2,2- 0 dichloro- 1, 1, 1-trifluoroethane; and 10-59 weight percent octamethyltrisiloxane, 40-89 weight percent 1,1, 1,2,3,4,4,5,5, 5-decafluoropentane and 1-20 weight percent isopropanol.

5 6. A process for cleaning a solid surface which comprises cleaning said surface with a composition of claim 1 or 5.

7. A process for carrying an active ingredient in a solvent in which the solvent comprises a composition of claim 1 or 5. 0

8. A process for transferring heat from a heat source to a heat sink using a composition of claim 1 or 5.

9. A fluid for carrying silicone comprising a composition of claim 1 or 5. 5

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